Cam-eo Performance: "In Search of a Better Way” is a sequel to "A Cam-eo Performance" posted three years ago on 11/16/2018. (Main characters name is now John/Britney... NOT Wiley/Wanda).

My wife, Peggy, had been out of town at a three day conference halfway across the US. I let my inner Britney come out to play. I, Britney, spent three erotic days roaming the house in full femme 24/7. I tried on my girly clothing and lingerie and makeup. I also enthusiastically and loudly pleasured myself often with the aid of Peggy’s vibrator.

Unfortunately I forgot about all our tiny hidden security cameras that were located throughout our house. All my ‘fashion shows’ and love sessions were sent to Peggy’s laptop and cell phone. Her revenge is mean. And embarrassing. She promises to email my 'performances' to my entire email address book. Mom & Dad are first on her list.

Previously:

My wife, Peggy, had been out of town at a three day conference halfway across the US. I let my inner Britney come out to play. I, Britney, spent three erotic days roaming the house in full femme 24/7. I tried on my girly clothing and lingerie and makeup. I also enthusiastically and loudly pleasured myself often with the aid of Peggy’s vibrator.

Unfortunately I forgot about all our tiny hidden security cameras that were located throughout our house. All my ‘fashion shows’ and love sessions were sent to Peggy’s laptop and cell phone.

“My friends think your red Basque is particularly sexy. They all want to meet Britney and will be over for drinks and snacks next weekend; it will be your coming out party.”

“Remember Jerry and ‘Flaming Frank’ from my work? Your frequent sex workouts gave them lumps in their pants. “Frank, or Frannie as he likes to be called, was impressed with your creativity with the vibrator. We know he shares your cross dressing hobby and we know he likes boys.”

“At Frannie’s urging we all chipped in and bought a French maid uniform for Britney. Frankie says it closely matches his. He is very excited about you both wearing them at your party. He’s offered to help you serve if he can come dressed like you.”

“Let’s get something straight. You were the one that got caught doing wrong, not me. You are the pervert, not me. You took a risk and lost. I caught you and there will be consequences! Look up the word ‘atonement’ Britney. Accept your fate and become that girl you obviously want to be; your life will get much better if you do. Do you understand?”

I nodded my head. “I understand.”

Peggy handed me a one page piece of paper with writing. A quick glanced confirmed it was my entire email address book. Peggy had taken the time to list my parents, in bold, at the top of the list. Her implications were clear: obey or else.

“By the way, from today forward, while at home I want to see pretty Britney or maid Britney and not plain John: Bras, panties, garter belts and stockings starting today. Is that clear, Princess? Even at work.”

It was soon time for bed and Peggy mandated that I get fully dressed in Britney’s sleepwear before going to bed. I gladly did as instructed. Being blackmailed to dress up had an upside.

Peggy had just arrived home today and events were already unfolding quickly. Today was Friday. I had to go to work on Monday. What possible harm could my wife do in just two days?

It’s a new day - We resume the story

Breakfast Saturday

Peggy and I were sitting at the breakfast table finishing our morning coffee. I was, at Peggy’s ‘request’, still in my evening sleepwear. Without being told I put on a pair of shear black thigh high stockings over my cleanly shaven legs to humor her. Besides I have always loved the feeling that stockings gave me when I walk or rub my legs together.

“We’re going shopping today Princess. I want you fully femmed up and ready to leave at 12 noon. Do not have any outer clothing on and do not wear your wig. Get rid of your thigh high’s and into your red bra and garter belt set like I told you last night.”

“And there are these.” Peggy slid me a pack of artificial press-on fingernails from ULTA. “These are ¾ inch long. Make sure you are wearing them and that they are painted.” Peg handed me a bottle of “Vibrant Red” nail polish which would match my bra and garter belt.

I began shaking the bottle vigorously. “Where are we going, darling?” I asked.

Needed: pierced ears, a new shade of lipstick and new dildo

“We need supplies for your coming out party next Saturday and we’ll be making several stops. Shave close because we’re going to the cosmetic counter at Macy’s today. I’ll give you more orders later.”

The “no wig” mandate had me perplexed. Why this request?

“Is that all? I quipped. Peggy broke into a sly looking grin and said, “No, Britney there’s one more thing. It’s from Frannie.” Peggy handed me a small white box that seemed heavy for its size. I lifted the lid and looked inside. Frannie had gifted me a chrome butt plug that was a huge pink gemstone!

“It’s called a ‘Princess Plug’” Peggy said. “You damn well better be wearing it before we leave.”

I was sitting very gingerly at the table by 11:50 AM in my bra, panties, garter belt, stockings and makeup. My red toe nails looked rather nice through the nude toe of the stocking. I adjusted a loose garter strap. I was enthralled with my long and shaped red fingernails. I was getting used to my ‘Princess Plug’.

“”You did well, Princess but we need to get you some eye shadow and eye liner. Here’s your clothing for the day.”

“Standup and show me your Princess Plug, Princess” she ordered.

I stood and faced my backside to Peggy so she could see Pinky. “While you’re back there please adjust my rear garters.” I requested.

Peggy took the slack out of my garters and snapped one to check strap tension. After that was done, and to my surprise and delight Peggy grabbed Pinky and twisted it back and forth as if she was twisting a door knob. She evidently hit a nerve as I squealed in delight. ‘Another upside to Peggy’s feminization discipline’ I thought.

“You really like having something in your butt, don’t you Britney?” I said nothing but wiggled my butt to indicate that I had heard her.

Peggy: “Let’s get you dressed Precious.”

Peggy handed me one of my regular men’s Hawaiian shirts. I put it on over my bra and buttoned it up. My tits made the shirt tent out. I wanted my wig.

“Here are your shoes for today.” Peggy tossed a pair of women’s shoes in my direction. They were opened toed with 1 ¾ inch block heel. My nylons helped them slide smoothly onto my feet; my red toe nails made a statement of femininity that didn’t match my man’s haircut or voice.

For pants I was given a thin pair of ankle-length, high waist, pleated, khaki summer slacks. There were no front pockets; the short ankle length brought attention to my open toed shoes.

“Since you have no pockets you’ll need to carry a purse. The shoes match the bag. You, my little Sissy, will always carry my MK clutch purse.”

When I was fully dressed I looked like the stereotype of a North Hollywood male hair dresser and/or Las Vegas gay street hustler. No offense intended for either group. I really was missing my wig.

Peggy opened my purse and tossed in my driver’s license, a credit card and cash. She also made sure I had two tubes of lipstick, mascara, small hair brush and a couple tampons “for effect.”

“We are going shopping to replace my vibrator that you defiled and we’re finally getting Britney’s ears pierced. You’ll be happy that you did. There’s a mall I know of that will do your ears. The question becomes two holes or four?”

“To show you how reasonable I am we’re driving out of our area to a truck stop in Fontana that has plenty of sex shops. You will go into the store alone and select a new dildo. Be sure to ask an employee for help.”

Peggy handed me my purse and the car keys. “You drive Sweetie. You’ll get used to the heels in no time.” I followed Peggy’s directions.

We arrived at the Macy’s that Peggy wanted to visit. I grabbed my purse, exited the car walked immediately to the earring counter. Pointing to a bar stool Peggy told me “Sit down, cross your legs like a good girl, make a choice and don’t cause any problems so we can have some girly fun at the cosmetic counter.”

Peggy motioned for assistance and a lady immediately offered to help us. “What can I help you… ladies (?) with?” she asked. Her demeanor bordered between surprise and amusement.

“My Britney wants to have her ears pierced; next Saturday is her coming out party. We know she wants at least two inch gold hoops.”

Still talking to Peg the clerk began asking her questions. Peggy waved her off and said, “Direct all your questions to Britney; she’s a big girl now. She’ll also take care of the payment. I’ll be back in 15 minutes.” Peg smiled and walked away.

Fifteen minutes later Peg was back and I was sporting pretty gold hoops and zirconium ‘diamond’ stud earrings. I was holding a small plastic bag that contained four starter sleeping studs and a pamphlet that described caring for newly pierced ears.

“Four holes! Very brave my little Sissy; very pretty too.” I was subconsciously toying with my new jewelry.

“Let’s go Precious, it’s lipstick time.”

We were soon standing at the cosmetics counter. A young cosmetic consultant immediately offered to help. Speaking to me Peggy said, “Tell the nice lady what you want Sweetie. After all it’s your special coming out party next week.”

“I want a lipstick that matches my complexion.” I stammered. The woman did well in hiding her surprise at my voice and my image. The woman looked me over and said, “Someone did a nice job of applying your makeup. But your eyes and eyebrows need a little help.”

“I just want a lipstick that matches my complexion” I repeated. “I been doing my own makeup for a couple years.”

Peggy told the girl, “Show Britney what eye shadow and eyeliner can do for a young lady. Find her a subtle fragrance too. I’ll be back in 15 minutes.”

Pausing for a moment to check me out Peggy slipped the cosmetic consultant a $20 bill and whispered, “Make sure you use the longest lasting cosmetics that you have. Work your magic; I’ll be back in a half hour.” The cosmetologist smiled knowingly and nodded.

When Peggy came to retrieve me I had two bags of ‘supplies’ and a few samples. The cosmetologist motioned her over and said, “I tinted Britney’s eyelashes and eyebrows and did her eyeliner. The tint lasts four to eight weeks. Come back when I’m on duty and I’ll redo it all for 50% off.” Peg smiled and gave the girl a ‘thumbs up’. The cosmetologist continued, “I think Britney’s face looks very attractive and kissable.” Peggy scrutinized me.

Peggy: “I totally agree; what a beauty. Very kissable. Thank you!”

Peggy stared intently. “It looks as if your eye lashes are longer and your eyebrows look much better; your eye shadow is subtle but nice. We certainly wouldn’t want to draw any attention to your pretty Sissy self, would we? The makeup lady said you looked kissable! Frannie will be impressed.” Peggy laughed. “He will want to know if you’re suckable.”

I replied, “Stephanie did a quick touchup on me. She had me close my eyes while she worked on my lashes. The eyeliner felt cool as she was applying it. She said she used a special shade of lipstick. I hope it isn’t too red. She says I’m so pretty that she wants me to meet her brother.”

Before leaving I stared into a mirror. “Wow!” I looked much prettier than when I came in. My face looked like a fashion model’s face. Except for my short man’s haircut my face was show girl perfect. I slipped the cosmetologist’s business card into my purse.

Now that you’re looking and smelling feminine we are going to the Adult Sex shop.

Adult bookstore near a truck stop in Fontana

“You are not to go in and quickly grab the first dildo you see; you are to take time to become familiar with all their dildos, not a quick grab and go with the first one you see. As always you are to carry my MK clutch purse.”

I pulled into a gravel parking lot and found a parking place under a shade tree facing the front door. There was only one other car in the lot which most likely belonged to the clerk on duty. As I exited the car Peggy said, “Be sure to get us a dildo that we can share. See what other products they have; we may want to come back for other things. Don’t rush the purchase Sweetie.” She turned on the car radio and reclined her seat. She noted the time.

I adjusted my bra and steeled myself for what I was about to do by taking a deep breath and exhaling deeply. I tightly gripped my purse and entered through a door that said “Welcome”. Peggy could hear the door buzzer.

About five songs into her wait Peggy glanced up and watched as someone hung a “Sorry, we’ll be back in 30 minutes” sign in the store window. That’s odd she thought.

Over the next half hour three cars and a large truck came into the parking lot. Seeing the sign they all turned around and left.

Forty five minutes later the buzzer of the door opening jarred Peggy from a shallow sleep.

I almost ran into a man who was entering the store as I was leaving. His single cubic zirconium ear stud caught my attention. He held the door open for me; “Where have you been all my life, sweetheart? Let me hold the door for you.” He smiled at me in a flirting way as I walked past him. “A pretty girl like you should let her hair grow a bit longer.”

The crunching of gravel under my short heels seemed noisy. I was coming her way and carrying two bags. I was walking funny; my gait was different.

With bags in hand I slid gingerly into the driver’s seat. Placing the bags on the floor between my legs I leaned back and sighed. My eyes were closed and it was obvious that I was trying to relax. Peggy gave me time to compose myself.

“What did you get us Brit?” asked Peggy. I passed her the larger of the two bags. Peggy peered inside. Reaching into the bag she pulled out what looked like a harness. “You got us a strap on?” Her other hand was holding two realistic silicon dicks; one was longer than the other.

“Yes, Peg it’s a convertible strap-on. It’s very versatile. I had to flirt with the cashier a bit but I negotiated a large discount.” In an attempt to get comfortable I shifted my butt several times.

I fastened my seatbelt, started the car and sat there, with the car idling and my eyes closed.

“What’s wrong Brit? Did the clerk try to get fresh with you?” Peggy asked.

Britney explains

“No, the clerk didn’t try to get fresh. I did.”

Peg’s eyes got wider. “You got fresh?”

“You want me to be girly, right? At first the clerk was not going to help me until I walked to the register and he saw my pretty face. He took note that I was obviously wearing a bra. I told him I needed a dildo. Suddenly he became Mr. Helpful. He walked me over to a display case and made several suggestions. He had me hold each dildo in my hand and feel its girth and texture. He said that it looked like I knew how to properly hold a cock; he was flirting with me and it made me feel feminine!”

I paused a bit to collect my thoughts and then continued.

“Mr. Helpful had his hand on my back as he guided me to the dildo display. I thought nothing of it. After a few minutes he snapped my bra strap and asked what color my bra was. I told him it was red. Immediately after telling him the color of my bra he steered me to the strap-on section. He suggested a strap-on because it comes with two dicks; a shorty and a not so shorty. Both can be attached to the harness or used without a belt. You can control penetration. The short dick aligns perfect with my prostrate.”

Peggy: “How do you know that it aligns with your prostate?” she queried.

“Mr. Helpful insisted in showing me a few features of his product. While I held the shorty dildo he used the longer one to poke my butt from behind. Instead of hearing no sound when he poked me he heard a ‘clunk’; Mr. Helpful had hit Frannie’s pink jewel butt plug! He found resistance where there should not have been any. So I had to explain. And then I had to show him and then he saw my red garter belt…gently tugged on one strap. It was unexpected but strangely exciting. I fantasized that I was a girl.” I paused a moment and continued. “Because the dildo was used I could got 50% off. He sanitized it before putting it in the bag.”

Peggy was in shock.

“Because I’m now a store VIP he gave me a free item. Check my purse.”

Peggy opened my purse and retrieved my pink ‘Princess Plug’. A VIP card for the porn shop with “Ms. Britney” emblazoned on it was also in my purse. She quickly dropped both items back into my purse.

“I now have a blue ‘Princess Plug’; the gemstone is shaped like a heart, it fits better than Pinky and it’s cute.”

“You name your ‘Princess Plugs’?” Peg asked.

“When he was done Mr. Helpful sanitized Pinky and gave it back to me. He warned me that ‘Princess Plugs’ set off metal detectors at the airport.”

“So where’s the blue one now?”

I smiled wryly and said, “Blue Boy is where it’s supposed to be.” I carefully wiggled my butt for emphasis.

Taking a closer look at me Peg said, “Britney, why are you wearing a different shade of lipstick than when you entered the store and why are you walking and sitting funny?”

I turned off the car, leaned back in the seat and closed my eyes.

“It seems that VIP stands for Very Important Pussy. Having been in the store for awhile and after looking at so many sexy items I was already becoming aroused when Mr. Helpful found Pinky. He grabbed it through my thin pants and began wiggling it around like you did this morning; that made me more aroused. That’s when he hung the ‘we’re closed’ sign. He led me willingly to a VIP room in the back of the store.”

“A VIP room?”

“Yes. It’s a private lounge in the back of the store that looks like a bedroom.”

“And…?”

“When Mr. Helpful saw that I was wearing a red garter belt and black stockings he became very aroused. It wasn’t very long until Pinky was lying on a side table, my pants and panties were around my ankles and I was bent over the arm of a couch. Wearing the garter belt made it easier for him to get at me.”

“And…?”

“And the short dildo was buried deep inside me… and I liked it. He was holding onto my bra band like a rodeo rider and I was pushing back on it and moaning like a wanton Sissy slut. And then it happened.” I squirmed again in an effort to get Blue Boy more comfortable inside me.

“My gosh, Brit, WHAT on earth happened?”

“Mr. Helpful pulled out of me, discarded the strap-on, and then began fucking me with the real thing. I was still bent over when he ‘pegged’ me! Even though he managed to get a condom on it felt different. I felt him cum! I was so excited and I couldn’t help it; I came too. I soiled his couch.”

“All this still doesn’t explain the change in lipstick, does it, Precious?”

“After Mr. Helpful pulled out we were both still very excited. I was feeling very womanly just like you want so I sucked him off! And I took my own sweet time in making him cum; it was like it was meant to be. Afterwards I knew my lipstick was gone so I reached into my purse and this is the first lipstick I grabbed.” A tear ran down my cheek. I briefly worried if my mascara was running. ‘Where did that concern come from?’ I wondered.

“My god, you’ve been ‘bred’! Frannie will be so disappointed.”

Peggy suggested that her ‘poor little girl’ had had a rough day and that she should drive us home. I agreed. We switched seats so I could recover. She started the car and we headed home.

“My Sissy sure has had a very busy day, haven’t you? You had your ears pierced, lost your virginity and became a cocksucker all on the same day!” Peggy cheerfully offered.

I fingered my new earrings and shook my head in disbelief.

“Tell me what you’ve become Sissy. What are you?”

“I’m a cocksucker.”

“You’re not just a cocksucker you’re a special cocksucker, you’re a Sissy cocksucker.”

“Yes, I am a Sissy cocksucker.” I held up my right hand and stared at my middle finger; the missing nail was obvious. I continued, “The worst part of my day is that I broke off a fingernail when Mr. Helpful came; he clenched.” I softly chuckled.

“What’s so funny?” Peg asked.

“The nail is still inside him” I lamented.

Peggy began driving faster.

“What’s the rush, Peg? Is our house on fire?”

Gripping the steering wheel and staring intently at the road Peggy tersely said, “After listening to your adventures in the dildo shop my pussy is on fire; your description has made me moist and horny. I wish I could have seen you sucking his cock. I want to get us home so I can jump your bone.”

I was beginning to believe there were some real benefits to being Britney. Perhaps I should just let Peggy have her way. From out of the blue a random thought popped out of my mouth, “I wonder if Frannie is circumcised?”

Peg glanced at me for a moment and increased her speed.

I was wondering if I could turn the tables on Peggy and photograph HER in a compromising position. Maybe Frannie would help this happen. Take a photo of Peg making love to a woman…or sucking off a She-Male… maybe that ‘woman’ would be Frannie? There had to be a way to make my ordeal come to an end before I became permanently imprinted as Blowjob Britney. I began to mentally replay what I had done. I smiled and let my mind wander; my cock began to harden.

I need time to think this through. Would my pretty makeup last until my coming out party next week? Do I care? Oddly, I do.

A Cam-eo Performance: "Saved By a Sissy”

(The third and final Cameo story of being ‘Caught With Consequences’)

Previously: John reflects

Black mailed. I had spent the weekend being physically and psychologically feminized by my wife, Peggy, because I had been a bad ‘girl’ while she was away on a business trip. My wife wanted retribution done in a very special and prolonged way; and I need to find a way to put an end to her vindictiveness.

My ‘crime’: Being discovered and outed by my wife cross-dressing and pleasuring myself. I had been electronically caught enthusiastically and loudly pleasuring myself with my wife’s vibrator. Peggy told me I deserved punishment for defiling her vibrator.

Unknown to me the explicit sex videos of my cross-dressing and masturbation sessions had been sent to my wife’s laptop while she was away at a conference. Our home security video system gave irrefutable proof of my multiple, but very pleasurable, ‘transgressions’. I was being black mailed by my vengeful wife. Not good. Peggy threatens to send my ‘performances’ to everyone in my entire email address book unless I do exactly as she says.

Caught with consequences for me involved blackmail and ‘forced’ feminization dick-tated by my wife; cock sucking was a fringe benefit.

In fact Peggy is planning a ‘Cumming Out’ party for this weekend that several of her co-workers had been invited to. One of the attendees is gay and lonely for a ‘companion’: Frannie. Peggy had promised me to him; I need to find a way out of my predicament very soon.

In addition to being dressed in full femme in public, her ‘penalty’ resulted in me having my ears pierced, my eyebrows shaped, artificial nails and having long lasting makeup applied. My own shoulder length shag hairstyle added to my feminine appearance. Peg found ways to make it look more girly.

It had been a very full weekend. I wound up being on the receiving end of a strap-on dildo and a penis; I lost my anal virginity and I had become a cocksucker. I had also lost an artificial fingernail inside of the owner of an adult Fontana bookstore. Peg replaced my broken nail shortly after we got home from the Adult Bookstore; all 10 nails were once again shaped and pretty. A neutral color was allowed for work.

It’s now Monday morning and I, John, had to report for work today. Unfortunately for me my face still looked very obviously made-up like a Britney and not like a John.

Start of my work week - My face still looked kissable

Peggy’s revenge mandated that I remain in full femme mode on weekends and while at home. Mid-week ‘at work’ revenge was slightly less onerous. On Sunday evening my best attempts to rid myself of Britney’s long lasting make-up were in vain. It was now Monday and time to go to work. Unfortunately I was as pretty today as when the Macy’s cosmetologist had finished making me pretty on Friday. My face still looked very feminine. I think it was my dyed eyelashes and shaped eyebrows that brought attention to my womanly appearing face.

I worked as a bookkeeper for a large national company. I was required to wear a shirt, tie and sport coat. No problem. My wife’s punishment required a few additional items of clothing under my boy clothes; panties, garter belt, stockings, bra, camisole and ‘Blue Boy’ which is my newest ‘Princess Plug’. Her ‘no socks’ mandate combined with the shorter inseam of my ladies slacks exposed my black nylons to detection.

Peggy decreed that my ‘go to work’ bra, worn under my shirt, would be a low profile, cup size ‘A’ sleeping bra and a camisole to lessen the chance of bra detection. For outer wear my top was a colorful tropical print shirt that looked more like a blouse than a man’s shirt; it looked very chic with the skinny belt and khaki Lands End Woman’s Slim Leg slacks I wore.

A femme looking Navy Blue blazer with a LGBTQ Hummingbird-Rainbow lapel pin completed my ensemble. Although very stylish I talked Peggy out of sending me to work in Britney’s 3 inch black kitten heel pumps. Peggy allowed me to swap my four hoop earrings for the tiny gold ‘sleeper’ studs that came with my piercings; I needed to remain employed. Peg’s always been a humanitarian.

Her humanitarianism really came through when she sewed the pockets of my blazer and my slacks closed. This mean spirited action necessitated me having to carry my wife’s medium sized Michael Kors black leather cross body purse to hold my wallet, car keys, lipstick, mascara, etc. A smaller, less obtrusive, clutch purse was out of the question. The gold colored MK logo and shoulder chain definitely stood out. Peg made sure that my cosmetics, two tampons, nail polish and a hair brush were inside. Shaped artificial nails, ear piercings and shag hairstyle completed me. To a casual observer I looked like a woman.

Inwardly I was pleased at my image. I regretted having to go to work and miss out on wearing Britney’s high heels.

Peggy laughed at my predicament. ‘Accept your fate and become the girly tramp cocksucker you obviously want to be; your life will get much better if you do’ is what she had told me when she first returned home from her trip on Friday.

It was now Monday. As I left for work Peggy spritzed me with ‘Cashmere Mist’ perfume and held up her list of my email contacts as a reminder of her threats. “Just one ‘universal send’ will seal your fate, Britney” she said.

As I drove to work I vowed to find a way to make my nightmare and Peggy’s blackmail stop.

Britney Arrives at Work

I reported to work at 8 AM on Monday morning hoping to get lost in the anonymity of a sea of desks. I had hoped to blend in and go un-noticed. Unfortunately I immediately generated a LOT of attention. Perhaps I shouldn’t have worn the gold chain shoulder strap of my purse as I entered the building. I quickly made my way to my desk. My perfume wafted ahead of me.

I put my purse in the lower drawer of my desk as I had seen my female co-workers do for years but not before receiving several comments about how nice or pretty it was. The MK gold logo badge and gold chain shoulder strap (and my Cashmere Mist) seemed to be a homing beacon to the ladies… and to Mel from the mail room.

I nervously squirmed in my chair as I still hadn’t become fully accustomed to my Princess Plug; I think I had found a way to massage my prostate by squirming around or rocking back and forth. Crossing and re-crossing my legs a certain way also created odd but interesting sensations; so did clenching. I sensed that if I rocked and squirmed correctly that I could achieve an anal orgasm; or perhaps a few minutes in a bathroom toilet stall could do the trick. It was something to consider and it was something to experiment with; it’s nice to have options.

Employees from other departments made a point of walking by my desk, looking and sniffing; the click of cell phone cameras sounded like crickets. Co-workers asked me to pose with them or they would blow me a kiss. My very feminine eyebrows, long dark and curled eye lashes were the subject of much finger pointing and gossip; I was being called ‘Kissy Face’. I received comments on my ear piercings and pretty hair. Peg would be damned gleeful about the discomfort I was experiencing.

Many of my female co-workers and a couple of the men asked what make-up products I used or made a comment about my MK purse and perfume. Our mail boy Mel (many of us referred to him as Melody) insisted on taking selfies with me. He was enthralled with Britney’s pretty face, eyebrows and tinted lips. After his 4th or 5th selfie, with his hand on my back, he whispered in my ear, ‘Oh, Sweetie, I can feel your bra!’ He emphasized his find by discretely snapping my bra strap.

“It’s a long story” I said. I had thought my white camisole would have prevented my bra from being seen; being felt was not in my plan.

During the day two of my male co-workers separately confessed to their own cross-dressing and complemented me on looking so femme and being brave enough to wear makeup and present as a woman at work. “It’s easy to be brave when you have no other options” I told them.

Jerry from my bowling team bent over my desk and inhaled my womanly scent. Pretending to be asking me a question he clandestinely showed me his bra strap! This was not that surprising because he and I had cautiously talked about cross dressing several times before. It takes one to know one. “Meet me in the men’s room after lunch; I want to show you something” he quietly said. Jeri winked and blew me a kiss before saying, “See you at the bowling alley on Thursday, Sweetie.” I rolled my eyes in forlorn acceptance of how my day was going.

My response to all the attention was: “It’s all a big mistake; it’s a dare that went wrong; I lost a bet; it was a prank that happened when I was asleep.” All of my explanations drew laughs and skepticism. These excuses sounded better than saying ‘My wife is blackmailing me’ or confessing that I REALLY like cross-dressing, wearing makeup, painted nails and all things feminine.

Lunch

Lunch in the company break room was hectic. I had put my sport coat on because I didn’t want my bra to be discovered in the same manner that Mel had found it. I carried my purse rather than hang it from my shoulder. I found myself worrying about my ‘cumming out’ party on the weekend. I must confess that the mental image of me in a French Maid outfit was very intriguing. Would mine be sexier than Frannie’s? I also worried about how to end my ‘caught with consequences’ ordeal.

After finishing my lunch I went to the rest room to take care of business and wash my hands. A reflexive impulse to freshen my lip color crossed my mind. I did take several paper towels with me into a toilet stall. I removed ‘Blue Boy’ so I could have a proper ‘rest’ break. When I was done I used a disposable wet nap towelette to clean it thoroughly prior to re-inserting it.

I exited the stall and was washing my hands when Jeri entered the washroom and locked the door behind him. He had a huge smile on his face.

“Johnny, your courage is amazing. So is your pretty face.” As he quickly unbuttoned his shirt he confided, “I knew you’d like to see the pretty matching camisole I’m wearing.” Indeed it was the same color as his bra strap; a fine matching outfit. “That’s very pretty, Jeri. I’m sure it makes you feel dreamy.”

Out of an ill conceived case of competiveness I said, “Check this.” I loosened my belt and let my trousers drop. Jeri stared open mouth and took in the beauty of my red garter belt, black stockings and black panties. I doubt that he even noticed my cami since his eyes were fixated on my crotch. His eyes had the same lustful look as Mr. Helpful’s eyes at the dildo store.

Jeri tentatively reached over and gently checked the tension of my garter strap. “Wow” is all he could say. I pulled my pants up, buckled them and left Jeri in the men’s room with his camisole on full display.

To Pretty John in bookkeeping

As I exited the restroom the department office manager, Wanda, found me and announced, “You had a gift delivery while you were at lunch. It seems you have a secret admirer. We had a little trouble in getting it to the right person. There wasn’t a complete name on the delivery.”

I smiled broadly. “Oh, really?”

Wanda made a point of sniffing me and thoroughly checking me out from head to toe before continuing. “It was simply addressed to ‘Pretty John in bookkeeping’. Considering your appearance and girly scent we made a wild guess and put it on your desk.” She laughed at her little joke; there is only one John in our department. “What’s the name of your perfume, Missy?” Wanda didn’t stick around for my reply.

When I got back to my desk a small wrapped gift and a single long stem red rose was waiting for me in the center of my desk. A gift card hanging from a red metallic lips shaped helium balloon read, “For Pretty Johnny”. The gift card was unsigned. Upon opening the gift I found a gold colored tube of lipstick. I extended the lipstick, sniffed it and smiled. Looking around to see if anyone was watching I put a small blotch of the color on my wrist to check the color against my skin tone. Coral Rose. The shade was perfect.

Looking around again I noticed a half dozen co-workers watching me; I couldn’t tell who my ‘Secret Santa’ was. I suspected that Jeri was my benefactor; or maybe the mail boy-girl; or maybe Peggy. Thankfully the card was not signed, ‘Frannie’.
I stood the lipstick upright like a beacon on my desk. I wondered if it would draw in more gossip ‘moths’.

I needed to find a way to stop Peg’s ‘caught with consequences’ punishment and the upcoming ‘party’ with Frannie.

I tried to get some work done but I found it difficult to concentrate with so many distractions. I felt like I was entering wrong numbers in wrong places… shuffling the same pages of data that needed to be entered into my computer. Coworkers walked by to look and sniff me; more photos were taken.

Last Break

I went for my last break of the day and sat at an outside table to try and relax. I closed my eyes, took deep breaths and freed my brain from the stress of the outside world. It helped a lot. I didn’t even stress on how to get out from under Peggy’s revenge. Fifteen minutes later I was feeling much better.

Called to Human Resources: Diversity and Inclusion

45 minutes before the end of my work day Office Manager Wanda came back to my desk and said I was to report to Human Resources. “John, Senior management has concerns about the loss in productivity in our department; your feminine appearance today has caused a lot of distraction. If you are transitioning to being a female you need to let us know. You’ll be meeting with Matt Hager, Vice President of Human Resources, Diversity and Inclusion.”

I looked up in disbelief. “Am I being fired?” I asked.

“You are not in any trouble just yet and Mr. Hager’s here to make sure things remain that way. I hope a reasonable solution can be reached. I’d hate to lose you as an employee. Grab your coat and personal items and come with me.” She pointed at my gifts. “Don’t forget your purse, Sweetie,” she mockingly advised.

Leaving the balloon and rose on my desk I put my new lipstick and the card in my purse and followed Wanda. I didn’t know what H.R. Diversity and Inclusion was.

Wanda walked me to Mr. Hager’s office on the top floor of our building. It was a very large corner office with an ornate executive desk and dark brown leather chair, two large chairs faced the desk, a circular table in the corner with three chairs, a leather sofa with matching end and coffee tables. It looked like a living room set up for business and entertaining. An executive bath room, wet bar, a modest balcony, book cases, a floor to ceiling mirror and an audio visual center for corporate presentations completed the room.

Large floor to ceiling windows were beautiful; they made a very nice office even nicer. They were ‘one way’… no one could see in.

Alone with Human Resources

Mr. Hager remained seated behind his desk as I stood. After a brief introduction Wanda left. Something about the man seemed familiar. Before he spoke Mr. Hager took a long time in checking me out. My purse hung from my shoulder. I saw my personnel file on Mr. Hager’s desk.

Reaching over to shake my hand he smiled and said, “I’m glad to meet you again.” I recognized his voice. I recognized his smile. Had we met before? His solo ‘diamond’ ear stud and Rolex watch confirmed my suspicions; Matt was the man that had bumped into me as I was leaving the Fontana Adult Bookstore! He held my hand a little too long.

We were about the same size and build; he appeared to be several years younger than me. I wondered how a ‘youngster’ could have attained such a powerful position in the company.

Motioning to a chair Mr. Hager said, “Have a seat John or do you prefer to be called Britney? You may call me Matt.” I hung my purse on the chair and sat as instructed: I crossed my legs in a manly way and waited while Hager flipped through my file; the cuffs of my slacks pulled up my leg.

After what seemed like an interminable amount of time Hager closed my file and looked up. Gesturing towards my ankles he smiled and said, “It looks like you forgot to wear socks today Britney; your nylons are showing.”

I rolled my eyes and audibly gasped as I noticed there was a five inch gap between the cuff of my pants and the top of my loafer; my black nylons were clearly on display. I immediately tried pulling my cuffs down to hide my stockings to no avail so I put both of my feet on the richly carpeted floor; they still showed. Matt was enjoying my awkward moment. He was smirking.

Matt continued to toy with me. “Your makeup and feminine appearance has created a huge distraction and is interfering with our work production. You have eyebrows, lashes and lips that are much too pretty for a man. You even smell like a woman.” he said with a stern corporate voice.

I pursed my lips, assumed a Lauren Bacall/Sharon Stone attitude and asked, “Do you think my lips look ugly, Matt?” I facetiously asked in an oddly sultry feminine tone.

Matt’s reply conveyed a lot. His voice became softly wistful; “No your lips are the same pretty shape and color that I remember. I thought so on Saturday and you confirm it again today” he said. I sensed a repressed longing in his voice that I hoped I could use to my advantage.

Out of reflex I diverted my eyes and demurely replied, “Thank you” before realizing I should have said nothing.

Going on the Offensive

In an effort to take control of the situation I shot back with, “And you’re the guy that held the door open for me at the Fontana Adult Bookstore, called me sweetheart and then asked, ‘Where had I been all your life’, right? I see you don’t have a wedding band. Do you cruise Adult Bookstores looking to pick-up men Mr. Hager? Did your book store boyfriend breakup with you, Matt?”

Matt looked startled. I sensed I had struck a very sensitive nerve so I pressed on.

“You’re quite the player, aren’t you Matt; asking a man where he’s been all your life? Is that a good thing for a Human Resources executive to be asking, Matt? And then you had the gall to tell me that a ‘pretty girl’ like me should let my hair grow, right? What else should a ‘girl’ like me think; you were trying to pick me up, right?”

Mr. Hager blurted out, “The store owner is just a long term friend!”

“You just told me I have very pretty lips. Do you have a fondness for pretty men, Matt?”

Matt squirmed and looked very uncomfortable. “We’re here to talk about your future with the company.”

I smiled and replied, “I’m here alone with you because your bookstore boyfriend told you what had transpired between him and I.”

Matt shuffled papers on his desk but didn’t make eye contact and there was no denial. I had hit an unintended bull’s eye! As I suspected Mattie at the very least was bisexual and had a boyfriend. I suspected Mattie was a submissive sissy and I would use this suspicion as leverage if I could.

Bull’s eye!

“Let me ask you again, Matt; do you have a fondness for men… a fondness for pretty men, Matt?” I scooted my chair back, spread my legs and laid my hand on my crotch. “Would you like to see my pretty panties, garter belt and stockings, Mattie?”

Matt’s eyes looked vacant like he was at a loss for words. I think he was rubbing his boner out of sight and under his desk while weighing his response.

I decided to go for broke as I was sure I was going to be fired anyway.

“Well, Precious, wouldn’t you like to have the same fun that your Fontana boyfriend described to you? I’m willing if you’re willing. Perhaps we can reach a mutually agreeable solution to our problem. Why don’t we sit on the couch and discuss things. Besides I have a few things that I think you would love to see. Let me show you.” I grabbed my purse and moved to the couch.

Matt takes the bait!

Matt used his intercom to tell his secretary to hold all calls and that he did not want to be disturbed. The work day was almost over and the building would soon be empty. I removed my jacket, laid down my purse on the couch and waited.

Matt locked the office door and turned around and stared at me; he was in deep thought. I waited a minute to let him ponder his options. “Would you like to see something pretty, Mattie? I asked. As he watched I stood up, unbuckled my belt and let my pants drop to my ankles. I gave Matt the same visual treat that I had given Jeri in the men’s room; my red garter belt, black stockings and black panties. I easily kicked out of my loafers and shed my camisole to reveal my lace bra. Matt shook his head in disbelief and continued to stare. I snapped one garter to entice my quarry.

I’m not sure what pushed Mattie over the brink; maybe it was my white lace bra or the sight of my cock protruding above my garter belt. Matt was on a mission. He unbuckled his pants and after making sure that I saw that he was wearing pink panties Mattie stripped down to his socks leaving his clothes and panties in a crumpled heap on the floor. Lust can do that to a person.

As he stood naked and sporting a fine erection I said, “Miss Hager, I see you shaved your legs and pubes just for me.”

“I shaved them because Ronnie told me to.” He paused and took a deep breath before continuing; “Now I shave them because I want to and because it makes me look and feel…”

I finished his sentence, “Shaved legs make you look less manly and feel more girly, right, Princess?”

Mattie walked over to me and began kissing me on the lips. As he was kissing me he gently took hold of my hard dick; his grip felt pleasantly erotic. We mutually and slowly masturbated each other for several minutes while we passionately kissed; illicit love should be savored and not rushed. Mattie stopped and looked me in the eyes with an unspoken question. When I nodded ‘yes’ he guided me backwards to the couch; I sat. He knelt between my legs.

I spread my legs to give him better access to what I knew he lusted for. Mattie spent more than fifteen minutes sensuously sucking me off; he was not an amateur. He derived great pleasure in fondling my testicles and toying with my garter straps and nylons; I sensed that Mattie wished he was wearing them. A wayward finger found my Princess Plug!

Pausing his skillful blowjob for a brief moment Mattie revealed, “My boyfriend said you had bought one of these.” He tapped on ‘Blue Boy’ a couple times before resuming his labor of love. He was hungry for sperm.

Referring to my Princess Plug I said, “Your boyfriend licked it first to make it slippery and then he slid it into me to avoid a crème pie mess that he created. What does he slide into you, Mattie? You act like a person that loves being slid into Miss Hager.” I chuckled a bit and said, “You’re a sissy bottom, aren’t you?” There was no denial.

In fact my comments seemed to have inspired Mattie to more ardently suck my cock; his Sissy tongue was heavenly. I was tempted to remove Blue Boy to see if Sissy Mattie would explore me further. I have no doubt that he would have eagerly rimmed me with his talented tongue.

Holding a garter strap in each hand Mattie skillfully bobbed up and down on my shaft. He made kitten like mewing sounds as he sucked and tongued me. It was electrifying. He truly knew how to suck cock. When I came it was in waves of ecstasy. Mattie eagerly swallowed every gush of my sperm. He kissed me on the lips and demurely said ‘thank you’. I could taste myself when we kissed.

Console and Control: Will it Work?

I held him to my chest and stroked his head and whispered what a great cocksucker my Sissy Mattie was. Mattie didn’t deny my comment. We rested on the couch; he wanted me to recover.

We made small talk as I gently played with his perky nipples. I made a mental note to give them a pleasant tonguing at my first opportunity. Mattie was in awe that I could come to work looking so feminine. He asked about my eyebrows, makeup and Princess Plug. There was a hint of jealousy in his tone; that I was presenting as a female and, due to his position, he could not.

Mattie also confessed that the owner of the bookstore was his first intimate boyfriend and that Ronnie had told him all about me, my talents, my Princess Plug and that he had pegged me.

Mattie had just admitted that he was a naïve newbie to the gay lifestyle he had drifted into; that Ronnie was his first lover! Mattie would need encouragement and guidance to become the submissive Sissy he was destined to be. It was a golden opportunity for me to shape and mold my own Sissy; another reason for me to suck his titties.

I nodded and added, “I lost a fingernail in Ronnie’s ass. Don’t be surprised when you find it.”

I began to negotiate

I ‘suggested’ that an important man like him could easily arrange a way for me to stay employed, perhaps working from home, and that in return I would keep him anonymously and frequently pleasured. I was offering to be his whore.

Resigned, yet anxious to suck another cock, I leaned Mattie back and took him in my mouth. I closed my eyes and concentrated on cock sucking; I was enjoying the texture of having a penis in my mouth again. I was blowing Mattie because I wanted to, not just to keep my job.

I was just starting to tease his pussy with my middle finger (he wasn’t plugged) when he stopped me. He backed his cock away from my lips. I was surprised and disappointed. As a submissive it appeared Mattie had more pressing needs; the needs and desires of every sissy bottom.

Sissy Mattie would rather be sodomized than receive a blowjob; he prefers sucking someone rather than being sucked. He is both a giver and a receiver in a weird sort of way.

Mattie sat up and removed a condom and a tube of lube from a table drawer. I sat motionless on the couch as Mattie rolled the condom down my penis. It felt damn erotic! What was even more erotic is when he leaned over and smoothed the condom onto my shaft using his lips and tongue to make sure there were no wrinkles. He obviously had no problem with the taste of latex.

We both stood up and he greased my condom covered penis. With well practiced ease Mattie lubed his boy-pussy; he was on a mission. After retrieving his pink panties from the floor Mattie led me to the end of the couch, bent over the arm rest, spread his legs and cheeks; he was offering me his pussy. He wiggled his butt as an invitation; he wanted to be bred.

Wearing only my garter belt and stockings I stepped into position behind him. Mattie was so anxious to get pegged that he grabbed my boner and guided it part way into his waiting orifice. He facilitated his own penetration by wiggling back onto my penis. Mattie knew what he needed; he was the perfect bottom begging to be filled.

As I began pistoning in and out of my Sissy the tugging of my garter straps as I thrust was erotic. Mattie wrapped his panties around his shaft and slowly stroked himself while waiting for the anal orgasm he lusted for.

I rose onto my tip toes and thrust in as deep as I could; my penis erupted. His orgasm enveloped him like a wave at the beach; his pink panties caught his ejaculate. I held tight and firm deep in his ass even after my throbbing stopped; I was hoping for something special to happen. It did.

Sissy Mattie’s post orgasm quivering and contractions resonated pleasantly on my dick. Mattie couldn’t help his involuntary squirming. I could tell Mattie was an experienced cum slut in the way he repeatedly clenched and milked every bit of sperm he could from my dick. It was exactly what I had hoped for. Ronnie was a lucky guy.

Mattie proves he’s the ultimate submissive I thought he was

Shortly after I pulled out of him, without being asked, Mattie removed the cum filled condom from my semi-flaccid penis. At first I thought he was going to empty it into his mouth; maybe next time. Instead he wrapped the used condom neatly in tissue papers for proper disposal, dropped to his knees and sucked my penis clean and back to full erection.

I gently pried Mattie off of my cock explaining that I didn’t have any sperm left for him; that it would take awhile before he could enjoy my cream again. His disappointment showed on his face. I pulled him onto the couch next to me so I could hug him. Positive reinforcement was exactly what my Sissy-in-Training needed. “Good girl” I said. “You are a very talented cock sucker, baby.” I gently patted him on his back like a mommy does to her child.

As we cuddled Mattie began to cry. “What have I done? My career is over; because I had to have you.” I wiped a tear from his cheek and kissed him. I tried to console him. “It’s our secret Mattie; Miss Britney loves you, Sweetheart.” He gave a deep sigh of relief and relaxed his head onto my chest; at that moment Mattie was my girlfriend. I knew it and Mattie knew it. He was my sissy.

A Bold Move

I got a bold inspiration. I tenderly kissed him and asked, “Since I look pretty for you would you like to look pretty for me, Sissy?” I asked. Mattie didn’t say no.

I smiled and plucked on a garter strap. “Unhook Mommy’s garter tabs and remove my stockings, Sweetie” I purred. I stood up and faced away from him. Mattie quickly scooted on his knees over to me and did as he was told. My stockings slumped down and my garter straps dangled. I knew he could see Blue Boy. I resisted having him remove it; maybe next time.

“Unfasten my garter belt and hand it to me, Sweetie.” He did. I smiled. Things were going well.

Still standing I said, “Carefully take my stockings off, Precious.” Mattie rolled them down my legs and I stepped out of them. Mattie immediately pressed them to his face and inhaled deeply. My cock dangled directly in front of him. Mattie licked his lips in anticipation; his cock began to grow.

Sissy Mattie looked up from his kneeling position and looked at me in a questioning manner. I knew what my Sissy wanted. “If you ask me I’ll let my Sissy suck me for one minute.” I rotated my hips a bit and slapped his cheek with my hardening penis. Sissy Mattie eagerly accepted his role.

“Please let me suck your cock, Miss Britney,” he implored. I made a point of looking at my wrist watch and said, “Sissy can suck me for one minute.” I loved every second of his oral skills. After the allotted time I ordered “Stop!” My Sissy reluctantly let my cock drop from his mouth; if he had begged I would have let him suck me longer.

I backed away from his talented lips and ordered Sissy Mattie to hold my panties open so I could step into them. After stepping into them I said, “Pull them into place, Sweetie” I said. Mattie took great care that they were just right. He even reached in and made sure my penis was in a comfortable position. Before releasing my waist band he kissed the tip of my cock as if putting a child to bed. Mattie had done as he was told and even more; I wouldn’t have expected anything else from a submissive Sissy.

Dangling my garter belt from my fingers I commanded him to stand up and face away from me. I wrapped my red garter belt around him and hooked it snuggly in place. I swear I could feel his heart beat increase; his penis certainly did. I used his shoulders to turn him around to face me. The garters dangled limply down his shaved legs. He was very pleased and obviously very aroused.

“The best is yet to cum” I told him

I pointed to his cummy pink panties that lay on the floor. “After you put those on you may roll my stockings up your legs and Miss Britney will make the final adjustments.” I began putting on my clothes while my Sissy was putting on my black stockings. The combination of the black stockings, the pink panties and his white skin reminded me of Good & Plenty candy.

I sat on the couch and watched. Mattie came over and in a short time I had her stockings and garters snuggly in place and properly adjusted. The bulge of his boner was sort of cute. Mattie was pleased and so was I. There was no doubt that I had control of my little sissy.

Taking Further Control

I reached into my purse and brought out my new lipstick and held it up for Mattie to see.

“Would you like to look prettier for me, Sissy? Let Mommy put some girly lipstick on you.” He dutifully nodded yes. “Yes, please Miss Britney. Will you please put some lipstick on me?”

“Why do you want to wear lipstick Precious?”

With his eyes looking downward to the floor my Sissy demurely said, “I feel very girly when I’m sucking a cock; it makes me horny and wet. I want to look as girly as I feel; maybe it will let boys know I like having my boy-pussy fucked.” Mattie had definitely resigned his self to being a submissive Sissy; my Sissy!

I carefully applied lipstick to Mattie’s lips and, as an afterthought, I put a small dab of color on each of his cheek bones; I easily blended in the color to create a nice blush of girly color on his cheeks. Coral Rose was perfect for his skin tone.

I held Mattie at arm’s length and took in the sight of a young Sissy gleefully wearing his first garter belt. “You definitely look fabulously feminine, Sweetie. Why stop with lipstick; let Britney pretty up your eyes too.” I was retrieved my mascara from my purse while Mattie came close enough for me coat his upper and lower lashes. My Sissy was anxious to looking pretty.

“Close your eyes and let me dry your mascara Precious.” Based upon her growing bulge she found my gentle blowing on her eyelids to be erotic. I used my eye lash curler to complete the look I wanted.

“Sissy darling, you really look very feminine; boys will definitely want to fuck you. Be sure to keep your pussy, cock and legs shaved and boys will know what you want.” I said. I tenderly caressed her cheek.

I smiled and my Sissy smiled. I pulled Mattie close and kissed her passionately on the lips. I used a free hand to tease the head of her cock that was extending out of her soiled panties. I was rewarding Mattie for exceptionally good Sissy behavior. I was creating and exploiting a Pavlovian response in Mattie.

Who’s the Boss?

Before things became too heated I led Mattie to the large mirror. I went and sat in her chair behind her desk. It was a subtle indication that I was her boss. I enjoyed watching Mattie as she posed and admired her girly image. Using ‘our’ lipstick she looked into the mirror and applied another coat. He kept running her hands down her nylons and feeling the tension in her garter straps. It reminded me of me.

I broke her reverie by asking, “Would you like to finish what you started earlier, my pretty cocksucker?” When she turned to face me I leaned back in her chair, pulled my zipper down and pulled my penis free. “Bring the lipstick with you, Sissy.”

After Miss Mattie had finished and swallowed what she had started earlier we had a meaningful conversation about my future with the company. “Wouldn’t you like more sex sessions like today, Sissy? Would you like to attend a party this Saturday at my house? I have a French Maid uniform that I’d love to see you in! I’d like you to meet Frannie; he’s a cocksucker to and would love to ‘do’ you AND your makeup.”

I think I had found a solution to SEVERAL of my many problems.

Friendly negotiations about my future with the company continued on the couch. I told her what I wanted and she agreed. In fact my Sissy suggested additional perks, benefits and guaranties that I had not thought of or had dared to hope for. She suggested employment security guaranties, contracts, non-disclosure and sexual exclusivity agreements and other things.

Our sexual Exclusivity Agreement obviously would exclude my wife. I asked for Frannie to be included on our sex partner list. Adding Frannie would take the pressure off of me once Mattie and Frannie became acquainted. Mattie did not mention her Ronnie. Neither did I. Details matter.

In return, based upon Mattie’s desire to have unprotected sex and her desire to consume my sperm, we both agreed to have monthly blood tests. I was to provide my stud services to her on a frequent basis.

It turned out that my Sissy’s daddy was the Senior Attorney for the entire corporation! “Daddy won’t deny me.” Mattie had absorbed a lot of legal tactics from her daddy.

I happily gifted my lingerie, new lipstick and nail polish to Mattie; the lipstick went well with her skin tone. We kissed goodbye. I left Miss Mattie luxuriating in her lingerie; she would be happily wearing it home under her boy clothes.

I left for home

My mind was whirring as I drove; I was about to be freed from Peg’s revenge AND I had a solution for Frannie. My wife did not need to know what the negotiations had involved. She should be very happy with the results; my methods were none of her business.

Considering the indignities and public embarrassment I had received over the weekend and at work I was through with Peg’s threats and demands; I had fully paid for all my transgressions. I had participated in homosexual acts, lost my virginity and had been ‘outed’ to my coworkers. And there were the intense and illicit ‘negotiations’ with Miss Hager that Peg would never hear about; nothing good would come from her knowing.

I would let the cat (Peg) have her last bit of fun with her mouse (me) before ending her game.

I got home at 7:30 PM, two hours later than usual. As expected my wife Peggy immediately pounced on me. “Where the hell have you been? Why didn’t you call? Drop your pants and show me your lingerie!”

I dropped my drawers. When Peg saw that I was not wearing my lingerie she went ballistic just as I expected. I let her rant for a couple minutes before putting a stop to it. I was done with her threats but I wasn’t done with wearing women’s clothes.

“Where was I?” I loudly said. “I was negotiating our future. Thanks to you I was almost fired today; we would have lost everything. Where is my lingerie? I traded my garter belt and stockings for a very lucrative future that will directly benefit you. If you send my ‘fuck videos’ to anyone we both lose; I get fired and we lose everything. I saved the day.” Peg calmed down and listened.

I let her know that the main reason for my new employment agreement was that I would have to function as an on call homosexual whore for Matt Hager, Vice President of Human Resources whenever he desired me; I would have to suck him and fuck him.

“Oh, is that all?” Peggy asked. I added that he may fuck me too. “Well that isn’t so bad is it Britney; now that you’ve been broken in? I’m sure you’ve been stretched enough so what’s the big deal about taking a dick up your ass again?” she replied. “Should we get a larger Princess Plug for you?” I rolled my eyes in exasperation.

I explained that I had negotiated a very lucrative pay raise and promotion to Special Project Manager and that I would be able to stay at home with full pay for an indefinite period of time. She remained silent while I explained everything in great detail but omitted my negotiation methods.

As I spoke I changed out of my work clothes and panties and slipped into fresh high cut panties, and a comfortable rose colored lounger set; matching open toed slippers completed my after-work ensemble. I brushed my hair and swapped my ear studs for the hoops. While waiting for a response from Peg I redid my lipstick.

When there was no reaction I picked up a bottle of Red Rose nail polish and began shaking it in preparation of giving my bland nails some color. I had hoped she’d compliment me on my choice of color; Peg didn’t react so I began painting my nails as I continued to explain the events of the day.

Family Negotiations

By the time my nails were dry Peg was extremely happy, we were kissing and life immediately got better. She agreed to delete all her blackmail related videos. She said I could dress up whenever I felt like it and whenever Mattie ‘required’ Britney’s presence. Stipulated and agreed to.

I made a point of getting unrestricted access to and use of the new family dildo; in return Peg insisted that she could us it and the strap-on on me whenever the mood struck her. Stipulated and agreed to.

Peg revealed that only Frannie was aware of my damning sex videos and not most of her office as she had originally claimed. Only Frannie and NOT any other co-workers would be over on Saturday. Yes, Frannie had high expectations and yes, I must wear the French Maid outfit to keep Frannie quiet. Yes, I may have to have sex with Frannie. Stipulated and agreed to.

I informed her that Mattie was both my boss and my Sissy and that he/she would be joining us on Saturday; that Frannie needed to bring a spare French Maid uniform for Mattie and that with a little luck Frannie would hookup with Mattie and not me. Stipulated.

We continued our discussion and many topics were covered. As with any couple sex and money were not the only subjects.

Rather than bore readers with all aspects of BOTH of today’s lucrative negotiations I list a few key points below. Read at your convenience.

General Agreements Overview

*An immediate pay raise and promotion to Special Project Manager reporting directly to Matt Hager, Vice President of Human Resources, Diversity and Inclusion.

*Fully paid Administrative Leave while my new Manager projects and duties were being determined.

*Executive Insurance, Benefits, Bonus and vehicle package. Five weeks paid vacation.

*Substantial severance package and buy out IF my termination was NOT “for cause”. A minimum of three years at full pay and benefits is guaranteed. Scandals, crime, blackmail, etc. were deal breakers.

*If my wife Peggy is involved in ANY matter related to or resulting in my termination (i.e. scandal, black mail) or the termination of Matt Hager ALL contracts and agreements become null and void.

*75% off all merchandise at Ronnie’s Fontana Adult Bookstore.

And of course there is a distinct benefit in having your own Sissy!

Ronnie stepped from the dressing room and back into the main convention room where the pageant was to take place. Drew remained in the dressing room.

Ronnie gathered with the other contestants near the stage podium and received the obligatory briefings, pageant rules and completed the required forms and releases. Glancing around at the other 15 – 18 contestants Ronnie checked out the competition. All were in basic girl garb but without makeup & heels. After all this was to be the first cut. Lads that didn’t meet a basic believability of passing as a woman were thanked and excused. Ronnie felt sad for those that were thanked and excused by pageant officials.

And then there were ten.

Ronnie was happy but a little nervous that he was to be in the finals. Several of the “girls” were very believable and had mannerisms that suggested they weren’t amateurs. They carried themselves differently than those that were excused.

The remaining contestants were told to change back to their normal men’s clothing and return for a second round of testing in one week. The next round required the works; makeup, heels, accessories and so on.

Entering the dressing room Ronnie changed clothes and stored his ‘costume’ in what looked like an over sized purse. Drew was nowhere to be seen. With a last glance into a floor length mirror Ronnie threw his bag over his shoulder and headed to the elevator to the parking garage.

Just as the down elevator dinged open Drew appeared from a nearby hallway. “Hey Ronnie, congratulations for making the first cut”. Drew stuck out his hand as if to shake hands and pressed a note and a tube of lipstick into Ronnie’s hand like you’d do with a head waiter if you wanted a better table.

“I dashed next door to Sephora and picked you up a good luck charm. It matches your complexion perfectly and is light enough shade that you can wear it during your daily activities or when ‘when the mood suits you’ as you said.

Ronnie stammered out a ‘thank you’ and could feel the involuntary blush well up on his cheeks. Tentatively Ronnie asked “will I see you next week?” Flashing a winsome grin Drew said “Sure… maybe sooner. Read the note when you get a chance.” Ronnie grasped Drew’s note and gift a bit firmer.

As Ronnie stepped into the empty elevator Drew patted Ronnie on the back. Ronnie turned to face Drew and quickly asked in a rapid run on sentence “Are you taking the elevator? What color is your dress? Do you need any help with your costume?” Ronnie was surprised at his own boldness in asking.

As the door was closing Drew replied “No, I’ll catch the next one. By the way I could feel that you’re still wearing your bra”. The door closed and Ronnie found himself staring at his reflection in the polished brass doors. Ronnie exhaled deeply and visibly slumped in an effort to rid his tenseness of all that had transpired over the last two hours. Or was it three hours?

During the ride down to the garage Ronnie tried to make sense of what had transpired, where some long suppressed desires and urges had come from. He knew they came from Drew but why? Drew had stirred him in a way that made his pulse rush.

The elevator door opened and Ronnie pushed his deep thinking to the background for now. Opening his car door he placed his shoulder bag of clothes onto the floor of the rear seat and slid into the front seat. Still a bit unnerved from the day’s events Ronnie tried to insert the tube of lip stick into the ignition. “Damn!” he thought. “I got to slow down and relax my brain”.

He exhaled and found his car key. Ronnie inserted the key but did not start the car. Instead he paused awhile and looked at his new tube of lipstick. Removing the cellophane wrapper Ronnie opened the tube and ran it out with one practiced motion. The color WAS perfect. And it smelled very nice. Looking first over one shoulder and then the other shoulder Ronnie made sure there was no one nearby. He reached up and adjusted the rear view mirror.

With familiar precision Ronnie slowly applied the lip color. He pressed his lips together as he always did and made a low smacking sound. The lipstick was, indeed, a perfect shade. He retracted the lipstick and replaced the cap. He read the color on the bottom of the tube. ‘Honey Blush’. “I must make a note of this” he thought. He placed the tube in his shirt pocket. The sensations were subtle but they were there none the less. He felt a familiar but not unpleasant stirring in his groin. There also were those far away ‘desires and urges’. Desires, thoughts and urges closer to his consciousness than they had ever been before.

Ronnie was about to put the car in reverse when he remember the note. He stared at the note lying on the passenger seat and picked it up. “I gotta read it sometime” he rationalized. The note seemed to crinkle loudly as he opened it. It read “I’m pretty sure I’ll be having a wardrobe malfunction pretty soon and I’m sure I’ll need some help and you offered. Call me.” Drew’s phone number and address were listed. Ronnie smiled. And the stirrings he was feeling grew stronger.

“Oh my God… what have I done!” Ronnie thought. He backed out of the stall and exited the garage. As he drove towards home his mind was racing. He was gripping the steering wheel intensely. After almost running a red light Ronnie tried to relax, took a deep breath and loosened his grip on the wheel.

Just before getting home Ronnie stopped at his favorite grocer. He spent more time than planned but selected three bottles of wine. He had a Chardonnay, a Riesling and a Merlot. The sales clerk greeted him and commented that Ronnie seemed in a very good mood. Actually the clerk said Ron looked perky. There was no mention of his Honey Blush lip color.

Ronnie got home, locked the door and put the wine in the refrigerator. He then changed into a special kimono silk bathrobe he fancied and perched himself on the couch in front of the TV. He has some very serious thinking to do. And it involved a lot more than the pageant. “Where are these desires, urges and thoughts coming from? And why does Drew make me smile?” And those sensations were of concern in a pleasant sort of way. “I just might wear my special baby dolls tonight” he thought. He smiled again and reached over and applied another application of his Honey Blush “chap stick”. Oddly enough the pleasant sensations came back. In truth the feelings popped up.

It had been a rough night for Ronnie following the events at the pageant as his subconscious kept wrestling with long repressed memories. Ronnie leisurely stretched and tried to recall his dreams and decipher their meaning. He yawned again and remained in the warmth and comfort of his bed while staring blankly at the ceiling.

Ronnie recalled being in elementary school and playing after school at his friend’s house. The name Josh came to mind. Yes he recalled it was Josh and his sister Lucy who were both a couple years older than him. They often played together. Nothing wrong with that he figured.
Then he recalled how they would dress up and pretend they were singing in a band, dancing and acting like they were big rock stars. It was an all girl band. More memories jumped to Ronnie’s forefront. He recalled that Lucy always insisted that they all dress up in skirts and tights to ‘get into the mood’. Nothing extravagant or too risqué but girly enough for what they were doing.

As he recalled the playacting only lasted for a couple years before Lucy moved on to other forms of play. Lucy discovered boys and other interests so the trio became a duet. Josh and Ronnie liked the karaoke and dancing to rock and roll. It continued to occupy their play time and it was fun.

Both boys eventually grew tired of the thick, warm tights. It was Josh that found that pantyhose were lighter than tights and would let you dance a lot easier on the wood floors. And it was Josh that also found that wearing panties enhanced the experience of the pantyhose. They made a good girl band.

It wasn’t long until Josh found some of Lucy’s cast off outfits that really made them look more authentic. A skirt, a short dress, maybe a cute blouse, short shorts, few bracelets… whatever was easy and made them look girly. It all added to their act. They practiced dancing with each other and the pantyhose made them glide easily around the room. And Ronnie fell in love with his feminine side. Especially the clothes.
Their play dates always took place when the parents were away or at work. Josh began locking the bedroom door. “Just in case” Josh said. “We don’t want our folks to think we’re sissies”. It sounded reasonable to Ronnie who was a couple years younger than Josh.

Lucy was a non factor and would come and go whenever she wanted. She thought that Ronnie and Josh were cute in a funny sort of way. She even suggested some songs and dance moves which the boys would sometimes include in their act. And it was Lucy that suggested they try a dash of lipstick to make the boys look more girly. Occasionally she’d paint their toe nails. “Nobody will notice because of your socks”. The smell of the polish was intoxicating to Ronnie. It was their personal secret. As Ronnie lay in bed certain things began to make sense.

Ronnie swung his feet over the side of the bed, straightened his baby dolls and slipped on his kimono house coat. He slipped into some warm mule slippers with a two inch heel. Ronnie drifted into the kitchen and retrieved his morning coffee. With a cup in one hand and the morning paper in the other he made his way to the couch. He sat down and curled his feet under himself in a natural but feminine manner. His odd dreams and emerging memories put the newspaper on hold. He began staring vacantly to nowhere in particular and let his mind wander some more.

There was a time…

There was a time when he and Josh were slow dancing in panties and pantyhose when Josh stopped. Josh dropped one hand down and gently cupped Ronnie’s penis through the nylons and panties. “Ronnie, have you ever noticed how nice it feels when you rub yourself over your panties and nylons?” Josh ran his hand up and down Ronnie’s crotch. Ronnie stood frozen as the sensation engulfed him. It felt very smooth and it felt very nice. It was very exciting in a new sort of way.

“Do you like the way this feels?” Josh asked. “God yes!” Ronnie exclaimed. “It feels like nothing I’ve ever felt before”. Both boys noticed that a significant bulge had begun to build in Ronnie’s panties. Josh was also looking a little lumpy in the groin. The nylon pantyhose rubbing on the panties which in turn stroked his penis was indescribable. It was mesmerizing. And it was addictive. “I can make it feel even better Ronnie but you have to rub me too. We’ll do it together”. With little hesitation Ronnie began caressing and slow rubbing Josh’s panty clad penis. Josh changed it up a bit by gently grabbing hold of Ronnie’s firmness. Ronnie followed Josh’s lead. Josh’s penis was so slippery through the two materials. Both of their young penises were firm and wanting. It was an exhilarating sensation. A magical throbbing was beginning to build in both boys.

Josh softly whispered “Ronnie this gets even better”. Josh increased the speed of his up and down stroking of Ronnie and Ronnie also began gliding his hand more quickly on Josh. The panties and nylons made it smooth and easy. Both boys were beginning to pant and slightly wiggle with some unknown but building anticipation. A sudden increased grip by Josh made Ronnie also exert a firmer grip on Josh's cock. They exploded simultaneously in a wave of extreme mutual bliss and cum. Life at that moment was heavenly. It was shortly after this life changing experience that Ronnie began to secretly wear panties and stocking on a frequent basis.

Ronnie the adult snapped back to reality. He found himself breathing more heavily. The memories were causing an involuntary arousal. So this is where those forgotten feelings and impulses began! Ronnie went for a fresh cup of coffee, returned to the couch and continued in his reverie of introspection. There’s more to this whole thing Ronnie thought. His mind drifted back in time.

Needless to say there were frequent repeats of Ronnie and Josh’s new ‘dance’ moves over the summer. Having to wash out their panties and stockings was a small price to pay for such pleasure. Both boys acquired their own sets of each item. It would be unbearable to have to do without.

Towards the end of summer while doing their special ‘slow dance’ Josh hugged Ronnie and said “I’ve found something even more pleasurable. Bill showed me. But first we start with our slow dance. OK?” Ronnie nodded okay. They had only danced for a few minutes and both were very rigid. Josh asked “Are you ready?” Ronnie again nodded his ok and quietly said “yes”.

Letting go of Ronnie Josh dropped to his knees and carefully slid Ronnie’s panties and pantyhose down to Ronnie’s ankles. Ronnie’s penis was pointing toward the ceiling. “Don’t move. I think you’re really going to like this.” Josh instructed. And with that Josh tenderly grasped Ronnie’s erect penis. Josh looked up at Ronnie and then, to Ronnie’s great surprise, Josh slowly sucked his penis into his mouth. Again Ronnie froze.

The warmth of Josh’s mouth combined with the firm grip of Josh’s lips made Ronnie see stars. His knees almost buckled. And then the sensation and feelings got better as Josh began dragging his tight lips slowly up and down Ronnie’s rigid penis. An occasional swirl of Josh’s tongue around the head of Ronnie’s penis was pure heaven. And then the firm downward glide of Josh’s snug mouth to the base of Ronnie’s penis followed by the firm lip grip on the upstroke was more than Ronnie could handle. Ronnie thought he could feel the tiny bumps on Josh's tongue. He erupted mass amounts of what he knew was cum into Josh’s mouth. His world shook.

But Josh didn’t stop. He swallowed! Josh briefly stopped and produced a tube of Lucy’s lipstick. It was a darker red maroon shade called ‘Cherries in the Snow’. Josh applied a liberal amount of the lipstick to himself and began repeating the smile producing cock sucking process again being sure to leave rings of color up and down Ronnie’s rigid cock. One ring was at Ronnie’s base, another was mid shaft and for a finale Josh applied some more lipstick and left a kiss imprint on the tip of Ronnie’s penis. “Look down Ronnie at what I left you. That’s something you’ll never forget. It’s a beautiful thing”.

Josh went back down on Ronnie’s shaft for a few more runs. Ronnie’s next eruption resulted in a lesser amount of sperm but with the same great feeling. Josh slowly stood up giving Ronnie’s penis a loving stroke of goodbye. Pulling Ronnie close, like a slow dance, Josh kissed Ronnie on the lips and expelled some of Ronnie’s cum into Ronnie’s mouth. By reflex Ronnie swallowed.

“What the hell was that?” Ronnie said loudly. “And why did it feel so damn good?” Josh started to pull up Ronnie’s panties and hose and replied “Bill says it’s called a blowjob. Not sure why because there isn’t any blowing going on. Did it feel good?” “It felt damn good but why the hell did you slip some of my cum back into my mouth? What’s up with that? And why the lipstick? ” Josh casually said “There are several reasons. First I like to mark territory, second the cum doesn’t taste that bad and third it makes us cum brothers. That’s very special. And it also gives you an interesting souvenir. You’ll get an additional thrill when you try to soap the red rings off your pecker. It’s a win-win. It also serves me as a goal to attain by showing me how much of your rod I was able to make love to. See how low YOU can place a love ring on a cock. It isn’t that easy. Besides it acts to keep my lips from chaffing. That is what Bill did to me and he’s a senior. Next time we dance you get to do it to me. OK? Promise?” Ronnie hesitated a moment, looked into his friends eyes and then quietly said “Okay Josh”.

“Be sure to wipe my lipstick off your mouth. It’s looks nice on you but it's noticeable. Before you do that lick your lips and see if you can taste yourself Josh advised”.

Adult Ronnie snapped back to the present. He found himself lightly trembling. Ronnie’s repressed memories and desires and weird dreams now had an explanation. Ronnie went for yet another cup of coffee. Things were starting to make sense. The source of his desires and urges were becoming clearer.

Back on the couch again Ronnie went back to pondering his past as he sipped his coffee. As he recalled Josh and Ronnie only did their slow dancing and panty stroking a few more times and then Josh and Lucy’s parents got a job transfer out of state. Ronnie was given Lucy’s hand me downs clothes and undergarments before the move. Luckily or unluckily, depending on your view point, Ronnie never kept his promise to Josh. Perhaps this was a deep seated regret that was messing with Ronnie’s head. It was an opportunity lost. Hmmm… Ronnie thought “Maybe Drew is my new Josh”?

Ronnie rose from the couch and walked over to the kitchen table. His car keys were there and so were the lipstick and wadded note that Drew had given him yesterday…the note with Drew’s phone number and address. Ronnie stared for a minute or two and then reached down and picked up the note.

Previously
Ronnie arose from the couch and walked over to the kitchen table. His car keys were there and so were the lipstick and the wadded note that Angel (Drew) had given him yesterday at the pageant tryout…the note with Angel’s (Drew’s) phone number and address. Ronnie stared at it for a minute or two and then reached down and picked up the note.

Chapter 4 – Do you want to dance?

Before Ronnie unfolded the note that Angel (Drew) had given him yesterday he picked up the gift lipstick. ‘Honey Blush’. Opening the tube he gave it a sniff which made him smile. “What a pretty fragrance” he thought. Extending the lipstick he put a small slash of it on his wrist. Indeed, the color was good for him. He then walked to the hallway mirror and carefully applied the ‘Honey Blush’ to his lips. He pressed his lips together to spread the coverage better. It looked and felt very nice. “I must remember to thank him.” He would use the wine as an appreciation indicator too. Ronnie used his hands to arrange his hair and blew a kiss to the girly face in the mirror.

Opening the note he re-read it: “I’m pretty sure I’ll be having a wardrobe malfunction pretty soon and I’m sure I’ll need some help and you offered. Call me.” It followed with his phone number and address. There was a PS that Ronnie had overlooked yesterday. “My name is Andrew and some people call me Drew. Please don’t. I hate that nickname. My friends call me Andy. My closer friends call me Angel. I hope you like the Honey Blush”. Ronnie reflexively smiled while his pulse went up a notch or two also.

Ronnie took the note and stuck it on the refrigerator with a Hello Kitty magnet for easy retrieval. The question became ‘should I call him?’ Taking a quick glance at the wall clock he was glad it was only 9 AM. They day was young! There was plenty of time for adventure. And there was the pageant he needed to prepare for. He was having second thought about participating: a $25 entry fee for a $200 gift card for the winner. It hardly seemed worth the effort. All that just so he could get ‘girly’ for a day.

Ronnie decided he’d give it some thought while he showered and got ready for the day. As he was turning on the shower he was glad he had a new set of peach colored tap pants with a matching camisole.

When he was almost done with his shower Ronnie grabbed his razor and quickly re-shaved his legs and armpits. He was an expert and was soon done. He was almost done when he decided to give his crotch a shave too. It had been several weeks. The act of pube shaving made him grin and feel pleasantly naughty. “You never know” he reasoned.

Stepping from the shower Ronnie quickly dried his body with a large towel but pat dried his legs. He then applied some moisturizer for good measure to his legs and a lesser amount to his pubic area. It always felt so nice.

Although his hair was only shoulder length Ronnie dried it and shaped it into a basic pixie style. A spritz of hairspray helped to hold the look. He applied his Honey Blush lipstick again, put on his kimono and mules and headed toward his phone. He felt a need to make the call. As he sat to make the call his mouth felt dry and his pulse was more rapid than usual. He opened a bottle of water, took a swig and sat down and made the call.

It took four rings before someone answered. At ring three Ronnie almost hung up out of nervousness. “Hello?” said the male voice on the other end of the call. “Is Angel there please, this is Ronnie”. There was a brief silence before the response. “Yes, this is Angel.” There was a relaxing tone in Angel’s voice and it made Ronnie’s relax a bit. “Oh my God, what do I say now?” Ronnie thought. “Yes, it’s Ronnie”.

The voice on the other end chuckled softly and said “We’ve already established that. How are YOU?” Ronnie composed himself and said “You were right, Honey Blush IS my color. Thank you again. Er… what are you doing today? You said you may need some help. You know, with the pageant”. Again his words all ran together. Ronnie hoped his voice sounded normal.

“I was just thinking about the pageant and could use some help with a few things. Not sure what to wear. You know… the usual stuff. Would you like to come over? I can make us a nice snack if we get hungry. It would be fun.” Angel said. With no hesitation Ronnie said “Yes, I’m free today. When’s a good time to arrive?”

“Five minutes ago would have been nice but since it’s only 10:30 now but how does 1 PM sound to you?” Angel said. “That sounds perfect. It’ll give me time to get my things together and stop for some pantyhose” Ronnie responded.

Angel paused a bit and said “When you go for your pantyhose make sure they are least 15 to 20 denier. We’re not into burlap covered legs in this house” he joked. “Be sure to get sheer Sun Tan or Skin Tone with nude toes. They will match your skin tone. If you’re feeling a bit trampy you might pick up a black set too. Control tops will help to keep your front flat. I noticed you were developing a bit of crotch bulge while I was adjusting your bra the other day. And not to be too pushy, bring your earrings”.

“What are you talking about? Earrings!?” retorted Ronnie. “I saw the tiny holes when I was hooking your bra. And they’ve been well used. I was standing right behind you, remember?” Angel said.

“Oh…. THOSE earrings” said Ronnie. “Well, I have to go now. I’ll see you in a couple hours”. Angel ended the call by saying “I’m looking forward to seeing you again. Bye for now”. Ronnie put the phone down and wondered what he was getting himself into. After another sip of water Ronnie got up and went to prepare for whatever was going to happen. It should be pageant related, right?

His shoulder bag still had his pageant gear from yesterday. He just needed to augment what he already had. He tossed in an extra bra, another tap pant and a “real” pair of panties. Just in case.

Ronnie put on his low profile A cup bra and then pulled on his new camisole. He then slithered into the matching tap pants. Both were a light peach color. There were no hose to put on since he was going to buy some later. He pulled on his good semi-skinny jeans which hid his panties and a white t-shirt that hid his peach camisole which helped hide his bra. This was his usual mode of operation.

Ronnie selected a nice dress shirt, buttoned it up and he was ready to go. He stepped up to the bathroom vanity mirror for a last look. Opening his jewelry box he took out a pair of dainty gold ball ear studs and expertly inserted them into his lobes. Ronnie noticed and retrieved his favorite anklet from the jewelry box. He rolled down his left sock and attached the feminine gold chain around his ankle. “Nice touch” he thought. It was another concession to his fem side.

Just before leaving the bathroom Ronnie applied a coat of his new Honey Rose “chap stick”. He did his lip smacking routine and then paused to think. Did he have everything? No he thought. He opened a drawer that had a variety of cosmetics, nail polish, etc. He ratted around for something special. He saw his special item in the rear of the drawer. He reached in and pulled out a different tube of lipstick.

Popping the cap off the lipstick Ronnie expertly twisted it out and gave it a whiff. Very nice color he thought. It was a dark red maroon lipstick. He closed his eyes for a moment and images of elementary school Josh popped into his mind. And so did the image of a lipstick kiss mark left on the tip of a special body part of his. Indeed, it was beautiful thing.

Ronnie retracted the red lipstick, put the cap back on and put the gold tube in his pocket. You can never be too prepared he reasoned. Before leaving his apartment Ronnie grabbed the three bottles of wine and put them in a pretty canvas carry bag designed for four bottles. “Angel has to like at least one of these wines” he figured.

The drive to Angel’s took about an hour primarily because Ronnie HAD to stop for his pantyhose. That took awhile. Macy’s always takes time. He bought three pair including a black pair. On impulse Ronnie also picked up a cute underwire demi-bra that was on sale. It came with a couple of removable “enhancer” pads. What the heck. Why not? Since he was already at the department store he also picked up two bra extenders. They can come in handy.

During the remainder of the drive Ronnie was thinking. “Angel is at least 3 or 4 years older than me. He looks as if he’s about 24 to 28 years old. I wonder where he learned his feminine ways? How does a man know so much about women’s things? And WHY is he interested in me?” Ronnie shrugged and continued driving.

Ronnie’s cell phone quickly led him directly to his destination. Angel’s place was a single story older home set back from the curb about 25 feet further back than his neighbors. Combined with the well established boxwood hedge that surrounded the house it created a comfortable zone of privacy. It was an older neighborhood and all the homes were well maintained.

Ronnie turned into the driveway and pulled forward to an apparent parking area close to a front porch. He turned off the engine and sat awhile to calm his nervousness. His nerve level was higher than normal. He dried his sweaty palms on his pants. He took a deep breath and exhaled slowly. Before opening the car door Ronnie freshened up his lipstick that Angel had given him.

Ronnie grabbed his pageant shoulder bag, the three bottles of wine and the Macy’s shopping bag with his recent purchases. With bag over his shoulder he walked toward the front door, locking his car via his key fob out of habit.

The porch was a covered one with two lounge chairs, a porch swing, and two side tables. Each table had a scented candle. It looked comfortable and inviting. Shifting his bra bag to his other hand he rang the doorbell and took a half step backwards. Ronnie was feeling a bit tense.

In less than 30 seconds the door opened and there stood Angel. He was wearing a short red satin waist long (and obviously feminine) dressing robe. It had a lot of humming birds on it. Ronnie noticed that Angel was wearing pantyhose. They clearly showed below the hem of the robe. Up top it looked as if Angel was wearing a boring man’s t-shirt. The total image looked good to Ronnie.

“Nice to see you again! You made good time. Please come in. It looks as if you brought some things” Angel said. They did the obligatory Hollywood hug and back rub. Angel playfully plucked Ronnie bra band. “Oh, I notice that you’re wearing a bra under your shirt. Nice touch.” Angel exclaimed. “Yes, whenever I get the chance. That’s what I do” replied Ronnie.

As he stepped into the living room Ronnie smiled nervously and looked around. The place was tastefully decorated. The dark hardwood floors brought back elementary school memories. “It’s nice to see you again too. Thanks for the invite. I brought the wine I spoke about and a few other items. I also brought the 20 denier pantyhose” Ronnie announced. “Perfect!” Angel replied.

“Have a seat. Let me have the wine and I will pop one open before we begin” Angel said. “I’ll pour us a glass and be right back. I’ll place your bags in my spare bedroom. Make yourself comfortable. The sofa is very comfortable. And your ear studs are a nice touch. They make you look prettier. I have a spare set of gold hoops that would look even better. We should give them a try.” Angel went to the kitchen.

Ronnie looked around the place and decided that the sofa was the optimum place to sit. It faced a large bay window that had a good view of the front yard. The window had lovely thick room darkening draperies. The single drape draw string was a gold braid that had cute tassels. Ronnie sat down at the far right of the sofa ensuring he had easy access to the coffee table and an end table for his wine.

Angel returned in a short time with a tray with two glasses and the bottle of Chardonnay. There also was a selection of cheeses, crackers and salami on a tray. Angel had opened the bottle in the kitchen and he filled their glasses in short order. Angel sat down next to Ronnie and handed him a glass of wine. “Here’s to the pageant” Angel said. They clinked their glasses, took a sip, and relaxed back into the sofa. Ronnie took another sip and placed the glass on the nearby coffee table. His wine glass clearly had a lipstick mark on it. Angel followed Ronnie’s gaze, saw the lipstick smudge and smiled.

“It appears you liked the Honey Blond, eh? I told you it’d look good on you. It even looks good on the wine glass” Angel joked. “Wait until you see how the sheer nylons make your legs look”. Ronnie blushed and laughed lightly at the humor of it. “Sorry” Ronnie apologized and replied “Your legs look very nice in those nylons. I noticed they are nude toe style. They look… eh… sort of sexy. What shade are they?” Ronnie picked up his glass and took another sip of wine in a nervous reflex.

Moments of silence passed as they both stared out the front window. It was a relaxing view.

Angel moved a bit closer to Ronnie and said “Make yourself at home. I was just getting dressed when you arrived. I need a few minutes to finish and will be back soon. There are some magazines on the table and a large coffee table book on The History of Cross-dressing. The TV remote is on the lamp table next to you if you want. I’ll be back soon. I have an extra room if you care to change now.” Angel turned and went to his room.

Sitting alone Ronnie took another deep breath, exhaled and took another sip of his wine. He thought he felt the start of a buzz. Ignoring the Vanity Fair and Glamour magazines he picked up the large coffee table book and began flipping through the pages. It was filled with many interesting photos of pretty men in pretty clothes in various stages of being clothed. Ronnie wasn’t focusing on the pictures… he was just flipping pages and trying to relax.

It didn’t seem long before Angel returned. He was wearing a form fitting LBD that looked a bit loose in the shoulders, a classy brunette wig, and perfect makeup. His eyes were delicious looking; his eye lashes were long and beautiful. He wore a dainty gold ring, a necklace with a cross and dangling ear rings. Angel also had a small jewelry box in his hand.

Sitting down on the sofa Angel moved closer to Ronnie. Angel opened the small box and displayed gold hoop ear rings that were about three inches in diameter. He filled their wine glasses and did another wine glass clink with Ronnie. They both took a drink. Not a sip but a real thirst quencher amount.

Putting his glass down Angel said “These will look very nice on you. Do you mind if I replace your studs with these hoops?” Ronnie hesitated a moment. Taking another sip of the Chardonnay, he looked directly at Angel and said. “Sure. Let’s give it a try.” Angel slid even closer and reached for one of Ronnie’s ears.

While Angel was removing the backing of Ronnie’s ear studs Angel said “I think you did a good job with your pixie cut.” Angel set down one stud and backing onto the coffee table and reached for Ronnie’s other ear. Ronnie turned slightly and slid closer to Angel to make it easier for the earring swap. It sort of tickled in a curious way. A few seconds later the remaining stud was also on the table.

Angel brushed a few stray hairs behind Ronnie’ ears, leaned closer and expertly inserted the hoops. Ronnie heard them click closed. Angel got both hoops in place with little effort. “There now” Angel said. “They do look prettier”. He sat back for a better look. “Very nice” he proclaimed. “Shake your head a bit and feel how they brush your cheeks. Here’s a mirror. Take a look”. Before looking into the mirror Ronnie thought “Having another person touch your ear lobes is pleasantly sensual”. Ronnie shook his head for effect and had to agree that they felt nice; like a reminder of his emerging femininity.

Ronnie reached over and put his hand on Angel’s nylon clad knee and gave it a rub. “Thank you for the use of your ear rings. They look and feel nice”. He gently shook his head again. Ronnie took another sip of his Chardonnay and stood up, placing the glass back on the table. “I think I’d better get into my outfit. I’ve been having doubts about the pageant” he stated. “It seems like a lot of effort with little in return other than having a chance to be girly for a day”.

“And you like to be girly don’t you? So do I” Angel said. It wasn’t a question it was a statement.

Before he went to the spare bedroom Ronnie had another sip of wine and took off his shirt and white t-shirt in the living room. He wanted Angel to appreciate his peach camisole. You could easily make out the outline of Ronnie’s ‘secret’ bra under the cami. Ronnie entered the bedroom with his bag of things and closed the door. He was definitely feeling the wine.

Emptying the contents of his bags on the bed Ronnie sat down at the nearby vanity, slumped into a relaxed position and closed his eyes for a couple minutes. He stood, took off his trousers and anklet and then removed his slinky tap pants and thought “Let’s not make this a project”. Standing nude in front of the vanity mirror Ronnie took a quick glance at his nudity. He saw that his penis was not as flaccid as he had hoped.

Opening the new package of sheer Sun Tan pantyhose he easily rolled them up his legs as he looked into the mirror. He remembered to put on his gold anklet. He replaced his peachy tap pants enjoying the way they felt as they slid up his nylon encased legs. The sensation was awakening a certain pleasant lust. Ronnie added a 20 inch long black half slip over his stockings and tap pants. “Excellent! “ he thought, Glancing again into the mirror Ronnie could still see the beginning of his crotch bump that Angel had mentioned. He was very glad he had bought the control top style pantyhose. They did help. Angel’s advice was correct.

Ronnie swapped out of his bland A cup undercover bra replacing it with his new underwire demi-bra that was a B cup. It also was black. Instinctively he pulled his spare flesh from under each armpit inwards and upwards to create a bit of cleavage. He left the enhancer pads in the bra. He did his little bra shrug to align things. He was about to pull his cami back on but decided against it. He grabbed his version of a Little Black Dress that he’d worn at the pageant tryout yesterday and stepped into it with practiced ease. He knew he was going to need help again with the rear zipper.

He found his black pumps with 2 inch heels and slipped into them. He then sat back down at the vanity and reached for his lipstick. Just before applying a coat he noticed he had the wrong tube. This was not the time for the dark red maroon lipstick. Reaching back into his bag he found his Honey Blush and expertly did his lips. He looked into the vanity mirror and pressed his lips together as usual. He found the Macy’s perfume sample of Cashmere Mist that he had been given and put the smallest of dab behind both ears and another dab low on his throat. “Less is more” he thought.

As Ronnie sat at the vanity prior to going back to the living room he could hear that Angel had turned on the stereo and was playing some soft music. Ronnie did his deep breathing routine twice, grabbed his hair brush, BOTH lipsticks, stood up and opened the door. He felt like he needed a little more wine.

As Ronnie entered the living room he saw that the drapes had been closed. Angel was busy lighting a couple of scented candles. Hearing the clip clop of Ronnie’s heels Angel turned to greet his guest. “My, don’t you look pretty. It looks as if you changed into a more suitable bra. That’s a pretty anklet. You look very passable”. “Thank you. A compliment from a person with such an obvious appreciation and knowledge of femininity is appreciated. HOW did you become so informed?’ Ronnie asked. “Oh, we can discus that a bit later. Care for some more wine?” Angel asked.

Ronnie nodded his head and clomped towards the sofa and wine. “I like the choice of your music. I used to dance to this type of music with a friend when I was in elementary school. We used to practice a lot”. He took another sip and sat down.

“Isn’t it fascinating the way things keep coming around in life. What was her name?” Angel asked. “His name was Josh. We danced on hard wood floor like these. Sometimes we played at being in a band… a girl band. His sister used to help” replied Ronnie.

Angel raised an eyebrow at Ronnie’s admission and smiled as he gazed at Ronnie. “Well that certainly explains a lot of things, doesn’t it? Come closer so I can do up your zipper”.

“To cut down on the noise of those heels on the hard wood you may as well kick them off for now. You can see I don’t have mine on” Angel said. Ronnie agreed and kicked them to the corner. He took the again offered wine and had another gulp. Ronnie moved closer to Angel, turned his back and asked “Please zip me up”.

“Please zip me up” Ronnie thought. Isn’t that how this all got started? He giggled aloud and waited for Angel. “By the way Angel the baggy shoulders on your dress tells me that you need a hand with your zipper too”.

Yes, it all started with a zipper. And what goes around comes around is a pretty true axiom.

As Angel was about to pull up the dress zipper up, not un-expectantly, he announced “bra fit time” and reached around to cop another feel of Ronnie’s nipples. Yes, they were hard again. After a few quick caresses with his thumb and fingers, with a gentle pinch of each nip, Angel zipped Ronnie’s dress closed. Ronnie was appreciative. He pulse rate increased.

Angel sat back a moment and said nothing for awhile. “Ronnie, you smell so delectable. What is that aroma?” Turning to face Angel Ronnie managed to say “Cashmere Mist. I was hoping you’d find it attractive”. “Yes, attractive. I find it attractive”. On impulse Angel leaned forward and gave Ronnie a soft kiss on his cheek. It left no outward mark. Inwardly it left a mark on Ronnie as that little kiss rekindled old urges, desires and memories.

Angel broke the ice by picking up their wine glasses and passing one to Ronnie. “Here’s to the pageant! Drink up.” Looking at each other they clinked their glasses yet again and both finished their wine in one gulp. “I’ll need to open another bottle. But that will have to wait until later” Angel said. “It’s your turn to zip me up and get rid of the sagging dress shoulders you noticed”.

Ronnie sat quite for awhile staring into Angel’s eyes quivering inwardly at the prospects of events that might happen. “Sure Angel just turn around and back up a little”. Angie scooted closer to Ronnie. A Victoria’s Secret tag marked Angel’s satin bra. Ronnie playfully snapped the bra band and quipped “I see you’re wearing a bra”. He paused to give Angel’s back a gentle caress from the armpits to his waist. Leaning forward Ronnie whispered as sultry as he could into Angel’s ear “You know this calls for a bra fit test”.

Reaching around from behind and above Ronnie brought his hands to the target area cupping and caressing Angel in the most seductive way. Ronnie was in no hurry. Angel made a low gasp but made no move to leave. Having gotten the green light Ronnie grabbed both breasts and did the nipple dance with his thumbs. Angel moaned but did not move. Ronnie thought Angel breasts had more mass than normal. It didn’t matter. They felt good to him. And it felt like the right thing to do.

Purposely breathing warmly into Angel’s ear Ronnie gave Angel one last titty rub and leaned forward and kissed Angel tenderly behind her left ear leaving a faint mark. “Your bra fits fine and you feel fine. Very fine” Ronnie whispered. A moment later and Angel’s dress was fully zipped. Still facing away from Ronnie Angel said “And what you did felt perfect. Combined with the scent of your perfume your touch was driving me crazy”. They both giggled like school kids… like elementary school kids thought Ronnie.

Turning to face Ronnie Angel looked into Ronnie’s eyes and leaned forward and kissed him on the lips. Not just a peck but a real kiss with a touch of tongue as they pulled apart. Ronnie’s heart was pounding. Life at that moment seemed wonderful. Embolden by the moment Ronnie reached over and brought Angel close and returned the kiss in a more passionate way. The flavor and melding of their lipsticks was erotic.

Angel broke off the kissing by saying “I best get some more wine. It looks like we can also use some more crackers”. Angel stood up, looked at Ronnie and said “I think we both need to fix our lipsticks”. Looking into the mirror Ronnie agreed. He needed a break if for no other reason than to cool off a bit. As Angel turned toward the kitchen Ronnie thought he saw that Angel was sporting a crotch bump. Ronnie was in the same situation. It was not an unpleasant feeling.

By the time Angel returned with the wine and crackers Ronnie was fully repaired and sitting on the sofa flipping through the big book again enjoying the photos and music. As Angel set the tray down he queried “Are you really thinking of bailing out of the pageant? If you’re only doing it to be girly for a day there are other options you know”. Filling their glasses with more wine Angel said “I think I could help you with some things. You really need to do something with your eyes and lashes and your nails are marginal at best”.

Being a bit offended with Angel’s comments Ronnie quickly spoke up. “What makes YOU such an expert? I’m doing okay”. Angel said “I didn’t mean anything by my comments. I apologize. It’s just I think you can do better. What makes me such an expert? Have a sip of wine and I’ll explain”. Angel and Ronnie both picked up their glasses and in a Hollywood moment they entwined their arms holding the wine glasses, pulling their faces closer together, and while looking in each other’s eyes they took a sip. They put their glasses down and sat back into the sofa.

“I may not be an expert” Angel said “but check out who the author of that 100 page book is. It’s me. Combine that with years of walking the walk rest assured I know a few things.” Ronnie checked the title page. It was true. Angel is the author. This explained many things. “I’m sorry Angel I guess I’m a bit tense. I’m lucky to have met you”. The music continued and had become a bit more up tempo. Angel had made a good party disc it seemed.

Ronnie noticed Angel’s pantyhose clad foot tapping time to the music. Ronnie had some more wine and said “This is a good song to dance to care to give it a try?” Not skipping a beat Angel said “Sure!” and stood up and began to dance. Ronnie was a second behind. The made it through two up tempo songs and began laughing at their own efforts. Their nylons made it easy to glide around.

They took a brief break, caught their breath and started dancing when the next song launched. Ronnie had surprised Angel with his dance moves. The next song was a slow dance, the music in which you hold hands and touch your partner type of song. They both stopped and it became quite.

Angel broke the ice and asked Ronnie “May I have this dance, miss?” Ronnie nodded and demurely took Angel’s hand letting him lead. They glided around the room in a firm but tender embrace. It was nice. The music, by chance, remained slow and Ronnie found himself laying his head on Angel’s shoulder as they danced. Angel was so gentle and comforting.

Another slow song began and their slow dancing continued. Angel looked down at Ronnie and gave him a passionate kiss. Not entirely knowing what he was doing Ronnie dropped one hand and pressed it on Angel’s groin. There was some distinct firmness there and it seemed to be growing. The dance continued and Ronnie continued to slowly stroke Angel's growing bulge.

Angel began to reciprocate to Ronnie’s delight. The control top pantyhose were not doing the job for either of them. Ronnie stretched up a bit and planted a loving kiss on Angel’s lips. Grabbing Ronnie tighter Angel began a full on make-out session that was leaving them both panting and wanting. They danced close to the sofa and coffee table. Ronnie stopped dancing even though the music still played on.

Not knowing where his boldness came from Ronnie began to really stroke Angel’s bulge, tracing Angel’s penis up one side and down the other. Ronnie used his thumb to better stroke Angel’s cock head while maintaining eye contact. Angel was busy too but used the palm of his hand to create a lovely hardness in Ronnie’s groin. No one was moving. Just kissing and stroking each other. For Ronnie the combination of the tap pants, panty hose and half slip was insanely perfect.

Without asking Ronnie picked up a pillow from the sofa and put it on the ground at Ronnie’s feet. Ronnie’s heart was racing and his blood was hot. Ronnie dropped to his knees and looked up into Angel’s eyes and said “Can you do us a favor and pull up your dress”? Angel was slightly trembling and said “Sure baby, anything for you”. Angel grabbed the hem and pulled up his dress.

Ronnie noticed that Angel was wearing pantyhose only. There was a damp circle of pre-cum in the middle of Angel’s pantyhose. His penis looked divine under the hose. Grabbing each side of the hose Ronnie savored pulling them down in a slow manner. Angel’s cock sprang free and was pointing toward the ceiling. It was about seven inches long and just about the best circumference. Ronnie blew his hot breath onto the shaft and got the twitch he had hoped for. Ronnie was glad that Angel was circumcised and that he was completely shaved smooth. Ronnie was glad that he had shaved his pubes too before driving over.

It had been many years since Ronnie had gotten this treatment from Josh and he was a little unsure as how to proceed. Ronnie kissed the tip of Angel’s penis and removed a pre-cum drip with his tongue tip which resulted in another twitch from Angel. It must be like riding a bike. You never forget. Angel was watching everything.

It seemed to Ronnie that both of their cocks got harder as Angel watched. Ronnie took a deep breath and made a first run with his tongue from the base of Angel’s cock to the tip taking in another drip of pre-cum. Pausing for a second Ronnie made a downward lick and then quickly moved to engulf the cock head giving it several swirls with his talented tongue. And then Ronnie stopped. Angel looked down with an unmistakable look of shock and disappointment.

Maintaining eye contact but remaining silent Ronnie smiled coyly. Ronnie reached over to the nearby coffee table and retrieved a tube of lipstick… a tube of red maroon lipstick. Still kneeling Ronnie used the mirror on the table to apply several thick coats. “Keep the dress up” Ronnie requested.

Lowering his head Ronnie continued giving his first blowjob. He made a snug ‘O’ with his lips and kept a firm grip. He locked his lips about half way down the shaft tightening his lip grip and slowly pulled his way up the shaft dragging and swirling his tongue as he went. He let the cock pop free and looked for a ring of color. It was there! He looked up to Angel and made sure he had seen it. Ronnie smiled and went back for more. Sucking, swirling and licking; making sure to maintain a good lip grip in each direction.

Ronnie came up for air, looked at Angel and took another gulp of wine. He also reapplied his lipstick. He wanted to mark territory. He had just gone down the now slippery shaft again when Angel gently inserted his fingers into Ronnie’s hoop ear rings. Angel used the hoops to guide Ronnie to where he found the better blowjob sensations… like reins on a young horse. Nice touch Ronnie thought. Up and down, a bit to the left, a bit to the right. Angel pulled the ear ring hoops up indicating that he wanted more attention to his cock head. Ronnie thought he could feel the veins in Angel’s cock. It all was very tactile. Ronnie had never felt so horny or hard.

Angel released hold of Ronnie’s ear rings giving Ronnie full control. Immediately Ronnie made a plunge for the base of Angel’s clean shaven cock and pressed his lips more tightly around the shaft. At the top of his upwards sucking he let the cock pop free again. It surprised Ronnie that the cock release actually made a popping sound. And there it was; a dark red ring of lipstick at the base of Angel’s cock. Josh would have been proud! Ronnie could feel the sweet slime that was Angel’s pre-cum. The taste was mild.

As long as he was cock free for the moment Ronnie took the opportunity to apply yet another coat of his red ‘chap stick’. Figuring it was time to bring the blowjob to a climax Ronnie made another run and tried some new moves. He lightly grabbed Angel’s balls and carefully gave them a gentle stroking. He moved his head around differently, made the cock head rub the roof of his mouth and tried jacking Angel’s shaft with a free hand as he continued to lick and suck. Angel began doing some face fucking thrusting moves.

Ronnie could sense something happening; something new. It felt like Angel’s cock was enlarging and beginning to throb. Ronnie increased his head bobbing, sucked a bit harder and more firmly gripped the base of Angel’s cock. There was a sudden and intense explosion of warm sperm! It gushed and squirted four of five times. Ronnie heard Angel cry out in ecstasy. Ronnie knew better than to stop and look up. And he was glad the taste wasn’t bad.

Ronnie changed the pace of his sucking and slowly coaxed the last of the sperm out the penis tip using his lips as a circular squeegee making several slow upwards runs on the shaft. He swallowed most of the loads retaining a small amount in his mouth. He had licked the cock clean. Ronnie could see Angel’s penis start to go limp.

Ronnie looked up at a very pleased Angel and stood up. He hugged Angel firmly and gave her a solid kiss on the lips and expelled the remaining sperm into Angel’s mouth. Angel didn’t resist and he didn’t swallow which surprised Ronnie. Instead Angel swirled his own essence around in his mouth first and then swallowed. Ronnie took note. Something new for sure.

Angel stood there in pure ecstasy. He managed to croak out “My god! Thank you Ronnie! And where in hell did you learn what you just did to me?” Ronnie licked his lips for the last of the pre-cum and smiled. He said “Wait. There’s more”. Ronnie picked up his tube of Honey Blond lipstick, applied a coat and then bent over and kissed the head of Angel’s dick making sure to leave a cute lip imprint of a different color. Angel’s cock twitched again. Ronnie then stood up and pointed at Angel’s new lip print. “See that?” Ronnie queried. “That’s a beautiful thing. And we’re sperm buddies now”.

Ronnie had the presence of mind to pull up Angel’s pantyhose. He smoothed them out a tucked Angel’s cock back where he found it giving it a final rub. Ronnie also pulled Angel’s dress back down and into place. They both retreated to the nearby sofa and plopped down. They were truly spent... for the moment. There was another clinking of glasses and another swallow of wine.

Ronnie reached over and grabbed Angel’s hand. He stroked the back of it gently and gave the back of his hand a kiss. Looking at Angel he said “Have I told you I have doubts about going through with the pageant?” Angel laughed. “I told you that you can be girly here any time you want. I can show you things and take you places that don’t involve travel. Besides I want to do up your eyes”.

“I feel bad about not giving you any relief” Angel said. “Whenever that ‘relief’ does happen we need to use the sofa or a bed. It was getting difficult for me to keep standing I wanted to keel over and writhe on the floor. I felt bad for your knees even though you had a pillow”. Ronnie let out a quite laugh. “I agree” he replied. “In fact it sort of sucked” he quipped. They both began to giggle at the humor of it all.

Still sitting side by side on the sofa and stroking each other’s nylon clad legs Ronnie asked “What did you mean that you can ‘show me things and take me places that don’t involve travel’”? Angel replied “Let me fix your eyes first. We’ll talk about the rest a bit later”. Giving Ronnie an impassioned kiss on the lips Angel stood up, grabbed Ronnie’s hand and guided Ronnie to Angel’s bedroom. There were eyes to be done and some relief to be given. And just maybe there might be new places and things that Ronnie should see and experience.

Previously
Still sitting side by side on the sofa and casually stroking each other’s nylon clad legs Ronnie asked “What did you mean that you can ‘show me things and take me places that don’t involve travel’”? Angel replied “Let me fix your eyes first. We’ll talk about the rest a bit later”. Giving Ronnie an impassioned kiss on the lips Angel stood up, grabbed Ronnie’s hand and guided Ronnie to Angel’s bedroom. There were eyes to be done and some relief to be given. And just maybe there might be new places and things that Ronnie should see and experience.

Chapter 5 – Are your ears ringing?

They entered Angel’s bedroom and Ronnie made a detailed mental inspection. It was a large room, maybe 15 x 20, with a large master bathroom with a walk-in shower, a separate tub, dual sinks and dual vanities. The walk-in closet seemed enormous to Ronnie. One side was obviously for male clothing while the other side was occupied by all things feminine. Dresses, skirts, blouses, belts, purses, and shoes were in perfect order. There was also a sit down vanity and mirror.

Angel opened a built in set of drawers to proudly display his lingerie. Silky and slinky. Panties, garter belts, nylons, shape ware, a wide variety of bras, heels, belts and purses; some items Ronnie didn’t recognize… the usual! One drawer had the lifelike breast forms that Angel had spoken about yesterday. Ronnie picked one up and felt its realistic weight and feel. Much better than the bird seed falsies that Ronnie had made. Ronnie placed it back. One drawer had a variety of sex toys and tubes of what had to be lubricants.

Ronnie made a mental note to get a garter belt and a few real stockings. They looked as if they could be a lot of fun.

The main part of the Angel’s bed room consisted of a queen sized bed, matching end tables and lamps and yet another sit down makeup table that was loaded with cosmetics. Very impressive Ronnie thought. There were two large windows that had pretty window treatments. Both windows provided a pleasant amount of natural light. An exterior boxwood hedge provided additional privacy. The list of ‘goodies’ went on.

Angel steered Ronnie to his makeup table and instructed Ronnie to remove his LBD and have a seat. “Have a seat, baby doll. There’s some wipes on the table so remove your makeup and lipstick. You’re about to have a makeover”.

Ronnie complied, carefully placing his dress on Angel’s bed. He sat down wearing only his pantyhose, anklet, tap pants, half slip and bra. He gazed at the large amount and variety of cosmetics, nail polish and “tools” of the trade like tweezers and eye lash curlers. The quantity of mascaras, eyeliners and eye shadows let him know that Angel was very serious about eye makeup.

Ronnie took one of his deep breath calming exercises, grabbed a makeup remover tissue from a pretty crystal dispenser and began to wipe off his lipstick. He usually never wore makeup. Angel was nowhere to be seen. There was some activity in the kitchen that he could hear and Ronnie could smell the pleasant odor of coffee being brewed. With his lipstick removed Ronnie sat in his lingerie and waited.

Ronnie took this break in action and scurried to the rest room, sat down and peed. He finished, stood up, blotted his penis tip and pulled up his pantyhose, tap pants and slip. He flushed, rinsed his hands and returned to the vanity bench. He didn’t have to wait long.

Angel appeared with a tray that offered coffee or tea and a variety of cookies and wafers. “Here you go, baby.” Angel said. “I needed to work through the wine buzz. Help yourself”. Angel placed the tray nearby. Ronnie opted for a basic Bigelow tea and a couple of cookies. He hadn’t realized how much he needed them. Very refreshing and much needed.

Angel pulled up a chair near Ronnie and as they munched and sipped tea they made small talk. It was obvious to Ronnie that Angel was studying his face and eyes. Angel’s eyes darted from Ronnie to the various cosmetic on the vanity. Angel finished his wafer and announced “Let’s give you a basic makeover as it’s getting late”. Angel leaned forward, stroked Ronnie’s cheek and gave him a quick kiss making sure there was no leftover lipstick or cosmetics.

Angel moved his chair closer and proceeded to give Ronnie an over view of what he was going to do. “First I’m going to apply a general primer hat makes foundation glide on more easily, then we’ll do some foundation, followed by a concealer, if needed, a bit of a bronze, and some blush. Your cheek bones demand some blush. Next we’ll do your eyebrows and get them shaped and under control. We’ll complete the session with my favorites; eye shadow, eye liner and mascara. It’s easy! Lipstick is last. No need to be concerned. Just relax into it”. Ronnie looked a little overwhelmed and took another sip of tea. He closed his eyes and faced Angel.

Angel went to work with well practiced efficiency. Ronnie liked the feel of the soft brushes, sponges and the smell of the cosmetics in general. A crotch bump was beginning to make itself known. The lump did not escape Angel’s notice. Angel smiled but ignored it for the time being.

Angel took great care with Ronnie’s eyebrows thinning and shaping them as needed. They took on a definite feminine arch. Angel decided on a smoky grey eye shadow and finished with black eyeliner. “Open your eyes baby doll as it’s time for your mascara”. Coating both upper and lower lashes several times Angel showed Ronnie an eye lash curler. “This won’t hurt and will make your eyes stand out.” After crimping Ronnie’s eyelashes Angel selected a reddish lipstick that almost matched the love rings that Ronnie had placed on his cock earlier. Angel thought his choice of lip color was ironic. “I’m done! Take a look”.

Ronnie turned to face the vanity mirror and could hardly break eye contact with the beautiful face that stared back at him. “Wow!” Ronnie exclaimed. “This is amazing! You were correct that I needed to do something with my eyes”. As he looked longingly into the mirror Ronnie fell in love with the image. His growing erection became more obvious. It was a situation that Angel could not ignore very much longer. “So what do you think doll face?” Angel asked.

Ronnie reached over, hugged Angel and gave him a passionate kiss on his lips. “I love it! I look so much prettier and feminine. Thank you. I really need to pay attention to my eyes. It certainly makes a big difference.” In return Angel lovingly grasped Ronnie’s obvious hard on through his slip, tap pants and pantyhose and began slowly stroking his cock. “Stop by some time and I can give you some tips. I’ll even toss in a bra check.” Ronnie smiled, closed his eyes and leaned backwards a bit.

Angel had to admit that Ronnie’s multi layers of silkiness did make cock stroking more exciting. Before things literally got out of hand Angel said “It gets better. Remove your tap pants, pantyhose, anklet and stand up”. Ronnie complied and stood there nude except for his black half slip for basic modesty. He sported a raging erection that begged for relief. Ronnie could hardly contain himself.

Angel brought out an eight tab black lace garter belt and wrapped it around Ronnie and hooked it closed. Ronnie watched but didn’t move. Putting a bath towel down on the vanity bench Angel handed Ronnie a pair of 15 denier black stockings. “Here you go baby doll sit down and roll them up. I’ll hook you up when you’re done”. Ronnie sat down and began rolling the silky stockings up his cleanly shaved legs. Each garter strap had a cute white bow where it met the stocking.

Before hooking the stockings to Ronnie’s garter belt Angel said “We have a problem. Step closer”. Looking into Ronnie’s eyes Angel grabbed Ronnie’s very, very erect penis, leaned forward and licked a pre-cum drop from Ronnie’s cock head. Ronnie’s eyes rolled back and he swooned and twitched in his own personal ecstasy. Ronnie realized the advantage of not wearing panties or pantyhose: easy access to your penis! What a brilliant idea.

Angel expertly attached each of the eight garters to Ronnie’s stockings taking time to ensure that each stocking and strap was perfectly aligned. This smoothing required a delightful ankle to crotch smoothing motion. Ronnie glanced into the vanity mirror. He almost had an orgasm as he saw the reflection. The tug of the garter straps was new and exciting. His raging hard on pointing towards the sky was so very naughty. He liked it.

Angel chuckled at Ronnie’s delight. “Step closer. It appears there’s another leak that requires attention”. Ronnie stepped closer and this time Angel did not lick the tip of his penis. Instead he gave Ronnie’s penis tip a kiss which removed the drip. And then Angel grabbed the base of Ronnie’s shaft and gently began slowly sucking Ronnie’s entire cock into his mouth, inch by inch, using a lot of tongue action. It was a beautiful thing.

Angel bottomed out and just as slowly began the slow upward suck withdrawal making sure to wet the entire shaft. Angel swirled Ronnie’s cock head and released it making the same popping sound that Ronnie had done earlier. And the dew drop was gone. Ronnie was enthralled.

Smiling at Ronnie Angel said “Come sit on the bed beside me baby doll”. Ronnie did not hesitate. Angel looked at the many lipsticks on his vanity and selected the same color that he had put on Ronnie. Color coordination was important to Angel. Making sure that Ronnie was observing Angel slathered on a thick coat of the pretty red color.

Announcing “It’s time to mark territory” Angel began a slow blowjob on Ronnie. There was no resistance or objections from Ronnie. Angel stopped briefly to inspect the lip rings he was leaving and to ask Ronnie to more fully get on the bed. Ronnie complied and laid back to enjoy the experience.

After a few more minutes of mouth action Angel asked “Remember when I said I could ‘show you things and take you places that didn’t involve travel’? In a lust filled gasp Ronnie’s said “Yes”. Smiling Angel said “Well lay back, bend your knees, keep your feet flat on the bed, close your eyes and relax”. Ronnie did what was asked of him. Prior to going back to pleasuring Ronnie Angel dipped a two of his right hand fingers into a jar of lubricant that was on the night stand.

Angel improved his position as to where Ronnie was laying, applied some more lipstick, leaned over and snugly gripped Ronnie’s penis just below the cock head with his lips making sure to leave a red ring. With a few swirls of his tongue Angels lips slowly slid down Ronnie’s shaft and left another red ring at the base of Ronnie’s shaft. ‘This should make him happy’ Angel thought.

Angel repeated the routine twice with a few variations. On his third downward run on Ronnie’s shaft Angel wedged open Ronnie’s legs slightly with his right hand just enough to be able to smear some lubrication around Ronnie’s rosebud of an anus. Ronnie made and involuntary full body twitch that popped loose his shaft from Angel’s mouth.

Straightening up from his task Angel brushed Ronnie’s cheek and said “Relax baby, I’m not going to hurt you, I’m going to take you to a heavenly place that doesn’t involve travel”. Ronnie took a deep breath, exhaled and laid back. Angel smiled, leaned over and kissed him on the lips making sure to run his tongue tip and spread Ronnie’s pre-cum back and forth on Ronnie’s lips. “Relax baby, it’ll all be OK”.

Grabbing Ronnie’s shaft with his left hand he went back to ‘The Blowjob From Heaven’. As soon as Angel started the downward slide with his lips he circled Ronnie’s sphincter a few more times with a greased finger liberally spreading the lube of his target. Angel then slowly inserted his middle finger into Ronnie’s ass making sure to fully coat both the inside and the outside. Angel continued with his shaft sucking and slurping and began sliding his well lubed middle digit in and out of Ronnie searching for his prostate gland. In a moment of boldness Angel slid two fingers in at one time. Ronnie gasped.

It was no more than three minutes of being finger fucked until Angel found his target. Angel was giving Ronnie’s prostrate a gentle rub and by sheer coincidence that on an upward suck Ronnie came. His cock throbbed once and sperm started gushing. Ronnie’s rectum clamped down on Angel’s fingers. Angel smiled and swallowed. Not a drop was wasted. There was that popping sound as Angel let go of his lip grip of Ronnie’s cock. Angel straightened up and looked down at Ronnie and enjoyed seeing him go through several aftershocks of pleasure. Ronnie finally opened his eyes and almost cried. It had felt so great, so new, so naughty and decadent. It was a beautiful thing.

Angel bent forward, kissed Ronnie on his lips and let Ronnie voluntarily suck his own cum from Angel’s mouth. Ronnie made a point of keeping his seed in his mouth awhile before swallowing. Angel looked down at Ronnie and brushed a strand of hair off Ronnie’s forehead. “There now, we’re ‘sperm sisters’”. Angel climbed onto the bed next to Ronnie and laid back. They both stared up at the ceiling in silence and let their breathing return to normal while holding hands.

Ronnie rolled over to face the vanity mirror. Angel immediately rolled over to spoon Ronnie. Angel unhooked Ronnie’s bra, removed one silicon breast form and began to absentmindedly trace circles around Ronnie’s nipple and do some gentle caressing. “Well baby doll, what do you think about what just happened? Did you like it?” Angel asked as he rolled over on his back.

Ronnie rolled back over too and said nothing for awhile. When he did speak he said “THAT was a beautiful thing. I never knew that an orgasm could feel that great. Thank you for taking me places that don’t need a car.” They both began to laugh. Ronnie turned his head and kissed Angel again just for good measure.

They laid in bed staring at each other for awhile when Angel said “I know the pageant has been worrying you a lot. You don’t need a pageant to feel or be ‘girly’. I think you should cancel out and come be girly with me. Let me make you more girly. You can be as girly as you want whenever you want. I know that with a little effort we could go out in public with no problems. And don’t forget I have a 100 page book that proves that I know how to make it happen. It’s loaded with photos, instructions and tips”. Angel gently pulled Ronnie’s face closer and gave him a passionate kiss as if to seal the deal. Ronnie kissed back.

Ronnie sat up, one of his bra cups was hanging down and empty. “I think you’re right. The pageant has been driving me crazy. I don’t need the aggravation. You ARE right. I can get girly without a pageant… with your help of course.” Angel nodded his head in agreement. “In fact I’ll call the pageant people tomorrow and tell them to count me out!” Ronnie announced.

Ronnie threw his nylon clad legs over the edge of the bed and sat up, his back to Angel, the tug of the garters felt erotic; a reminder of all things feminine. Without turning Ronnie asked “Will you hook my bra? It’s getting late and I need to be leaving in the near future.” Angel reached over and hooked Ronnie’s bra giving it a light snap to signal that it was hooked. Angel handed Ronnie the missing breast form and said “Keep these. Souvenirs’ of fun times are nice”. Ronnie inserted the form back into his bra, stood up and did his shoulder bra adjustment shrug. Everything was in place. Ronnie looked into the mirror and ran his fingers thru his pixie cut hair in an effort to look decent and broke into a wide smile. The dangling hoops looked great. Angel also exited the bed and made for the bathroom.

After Angel was done Ronnie went in and took care of business. Wearing the garter belt (without panties) made peeing so much easier. Just sit, pee and blot. He washed his hands and looked at the sight in the mirror in front of him: a pretty face, with beautiful eyes, which was wearing a garter belt and black stockings that had a penis hanging down. “Oh my god, what am I to do? I don’t want to ruin my eyes” he said aloud.

Angel entered the bath room and said “No problem. Leave your makeup on until you get home. I’ll send you home with tissues and makeup remover. It would be a shame to waste that look. You can keep the garter belt and stockings. Give me back the large hoop ear rings and I’ll give you a smaller set as souvenirs. And don’t be letting anybody but me be dragging your head around by the ear rings.” Both parties began to laugh loudly. It had been a memorable moment. Heck, it had been a memorable day.

Ronnie retreated to the spare bedroom and got squared way and packed. He did not put on his tap pants electing to wear only the half slip. It was short and had always tucked easily into his pants when he wore it to work. Not wearing tap pants, pantyhose or panties felt breezy in a decadently naughty sort of way. As he pulled on his trousers, sans underwear, he admired the lipstick rings on his dick. He smiled and was afraid he’d ‘tent’ his half slip.

Ronnie took a last look in the mirror and giggled. There, in the mirror, was a cute woman wearing a man’s shirt and pants. He made sure his new bra was barely visible under his cami. The last things he did were to apply his Honey Blush, smack his lips and dab on more Cashmere Mist perfume. He winked at the girl in the mirror and blew her a kiss of goodbye.

Looking around to make sure he hadn’t forgotten anything Ronnie removed the large hoop ear rings and exited to the living room sofa. Angel was already there with another tray of hot tea, finger foods and the smaller set of hoops. “Here take these hoops baby doll” Angel said as she clicked them in place in Ronnie’s ears. “Sit down for a few minutes and relax. You don’t have to rush off and the hot tea will be nice”. Ronnie agreed. Before he sat down Ronnie walked over and hugged Angle giving him a lingering kiss. Angel kissed Ronnie back and snapped his bra strap. “That’s what you do, right?” he laughed. They sat down. Ronnie put a bit of honey in his tea, stirred it, grabbed a cookie and sat back to let the tea brew a bit.

The living room curtains were open again and it was clearly getting dark. Ronnie sipped at his tea and told Angel” Thank you for an amazing day of amazing things. I feel relieved in many ways. The fact that I’m not doing the pageant is a relief and you relieved me in a way I never could have imagined”. They both giggled and flashed impish grins at each other.

Still seated on the sofa Angel looked seriously into Ronnie’s well made up eyes. “Let me give you some advice baby doll. Don’t let your dressing up make you paranoid and uncomfortable. Express yourself in any way you want. I think wearing an anklet, shaving your legs, maybe painting your toe nails or wearing some pretties under your men’s clothes is fine if it lets you get in touch with your fem side. And you must admit you definitely have a fem side which explains that beautiful scent you reapplied. Let your fem side out while you’re young and pretty enough to truly enjoy it”. Angel leaned over and gave Ronnie a brief kiss.

“Come over anytime but call first. You can leave a tooth brush and some girly things here if you want. You can always be girly for me. I may even let you wear the large hoop ear rings again. Maybe I’ll get you a house key”. They stood, hugged again and said goodbye again. Ronnie picked up all his bags, which included the makeup removal items, in preparation of leaving.

As Ronnie grabbed the front door knob Angel handed him a copy of his ‘The Art of Cross-dressing’ coffee table book. “Here, take this with you baby doll. I think you’ll learn a few things. I autographed it for you”. Ronnie opened the book and read “To a cute girl and a special sister. Love, Angel”. This called for another smooch and hug.

As Ronnie finally got the front door open Angel said “Next time we get together we need to work on your nails. They need help. AND make sure your toe nails are painted. No one will know. I slipped a couple shades that will look nice on you into your bag. And by the way pull up the zipper on your pants for god sake!” Ronnie glanced down and saw that Angel was right again. His zipper WAS open. But that was probably an acknowledgement that this whole day came about and was literally started by a zipper. It was the zippers fault.

A lifetime of reflections, Joanie’s final purge: “You Hook My Bra and I’ll Hook Yours”

Our story follows Joanie from a confused childhood to her Golden Years. Joanie reflects on the events and quirks of fate that led her to becoming Joanie. At 72 years of age, flashbacks and self reflection, allow us to better understand her lifelong search to understand ‘how’ and ‘why’. “Why me?” she asks.

(This story is semiautobiographical adult fiction. Explicit adult content. There are six chapters. All rights reserved. Comments appreciated.)

Chapter 1 of 6

Overview - Why me?

Our story follows Joanie from a confused childhood to her Golden Years. Joanie reflects on the events and quirks of fate that led her to becoming Joanie. At 72 years of age, flashbacks and self reflection, allow us to better understand her lifelong search to understand ‘how’ and ‘why’. “Why me?” she asks.

The story jumps around a bit but that’s what can happen in your Golden Years; that’s also what happens when you condense so many years into a brief snap shot. Indulge Joanie a bit and appreciate her story, appreciate her life. You may have many things in common with Joanie. Have you ever asked yourself ‘how’ or ‘why me’? Are you curious?

Chapter 1 - The Final Purge

72 year old John, also known as Joanie, was sitting on the floor of her walk-in closet sorting through an old open foot locker that contained belongings and memories of John’s female alter ego, Joanie. Rarely used since her marriage the box was more of a pleasure chest than it was a foot locker. Widowed a few years earlier (after 52 years of marriage) Joanie was tying up loose ends prior to, God forbid, suddenly becoming gravely ill or passing away.

In the two years since Emma’s passing the friends that had said “we’ll stay in touch” had stopped coming or calling. John had cut back on his forays out of the house preferring to tend his garden, sit at his laptop, surf the web or watch television. As the months passed John’s presence faded and more of Joanie emerged. Emma would have approved. And so would Michelle.

As you age beyond 60 and beyond 70… into the twilight of your life, age spots appear, your brunette hair grays and you grudgingly come to terms with your own mortality. The feelings of a need to downsize become more frequent and more urgent. You decide that you don’t want anyone having to sort through, toss out or try to understand all your femme acquisitions after you’ve died. It would be best to neatly tie up loose ends while you’re healthy. You can’t sort or purge from a hospital bed or mortuary.

The purge begins – sorting things out

As usual Joanie wore basic morning makeup; lipstick, a bit of blush and a touch of mascara. There was no need to go all out, just enough to look pretty and feel more feminine. Her high cheek bones helped with that image.

Joanie’s platinum white hair perfectly accented her Sapphire earrings and made her beautiful vibrant blue eyes stand out. Her below- the-shoulders hair was pulled back into a perky ponytail as it kept her hair out of the way as she worked.

Joanie was wearing her comfortable clothes which on this day consisted of a very cute and practical jumper and a matching peach colored panty and bra set. The bra was a snap in the front style. Hooking her bra in the back, by herself as she used to, has become impossible over the last few years. With Emma’s passing there was no one to help. Their long standing promise of “You hook my bra and I’ll hook yours” was no longer an option.

The closet

Over the course of a couple days Joanie had already reduced her large walk-in closet of clothes and shoes to 1/10th of what it had been. It was a slow and memory provoking ordeal. It was difficult to let go of her beautiful dresses and matching outfits. Some of her clothes were too formal or revealing for her ‘Golden Years’. There no longer was a need for party dresses or business skirts and blouses. The same could be said for some of her high heels and shoes. 3 and 4 inch heels were for the youngsters. Why risk breaking a hip?

On the first day of the final purge Joanie began by sorting and discarding her beloved Emma’s clothing and shoes. It was a sad process. Joanie was wearing a pair of beautiful gold and Sapphire drop earrings that she had been given by her wife on their fifth wedding anniversary so very long ago. Joanie always shared her jewelry with Emma and these earrings were their favorites.

Emma’s clothes had remained untouched in their walk-in closet since her untimely passing two years previously. Each garment that Joanie sorted brought distant memories flooding back. Joanie brought a chair into her closet in order to sit and determine what to do with each piece of clothing. Each item reminded her of specific moments in their lives. Joanie went through a half box of tissues throughout the day as she silently cried while sorting.

Removing a classic ‘little black dress’ from Emma’s side of the closet Joanie reached over to her own side of the closet and removed an identical dress from a hanger. They had bought a couple of identical outfits for a very special cruise of which the LBDs were just one. Joanie hugged them close, sat down and closed her eyes. There was a slight hint of their favorite perfume on them. Memories of a very special 10 day anniversary Caribbean cruise from years ago came flooding back.

Flashback – The cruise

The cruise was designed for cross dressers, friends and families. The cruise theme was “ A ‘Trans’ Caribbean Cruise”. The cruise was a 10 day total immersion period of non judgmental liberation for Joanie and Emma. The crew had been trained and briefed on what to do or say and they were trained on what to not say or do. It was the ships eighth voyage for gender fluid people. There would be no awkward issues on this cruise. Emma had researched it in detail and suggested that they take it.

The spring time cruise was a beautiful, life changing experience for them both. Prior to the cruise Joanie and Emma had no idea that there were so many likeminded couples. The cruise dinners, dances, and social events were amazing as was lazing by the pool and spa. Joanie stood up and grabbed the beautiful two piece swim suit she had worn. She recalled the unique tan lines she acquired. It was interesting to meet and interact with other cross dressers and their significant others in a pleasant non-threatening environment.

There were many cruise activities, seminars and social functions for those that wanted to participate. There were hair and nail salons, couples spa opportunities, Fantasy Foto studios, raffles, make over options along with all the other traditional cruise features. Shore excursions were to CD/TG/ Gay friendly locations. In other words the cruise was perfect.

On board seminars covered many topics including how to present as female, voice lessons, legal issues, do it yourself gaff and breast form making, makeup advice, how to cope and many other relevant topics.

Joanie was ecstatic when she won a free set of state of the art silicon breast forms after a seminar explaining ‘How to Present in Public”. They looked so very realistic and they felt fabulous. It was a dream comes true! Even the nipples were perfect. Joanie couldn’t wait until she got back to her cabin to put them in her bra. Emma mused “Wouldn’t it be nice if they could figure a way to add flavor to those nips?!” Emma knew that sucking and nibbling Joanie’s nipple were a special turn on for her.

By day two it was obvious that all willing passengers had taken advantage of the included facial make over. The less than perfect makeup you saw on day one was gone. Eyeliner, eye shadow and lipstick were distinctly better. You only need to relax on a lounge and observe.

Emma had arranged a three hour ‘Fantasy Foto’ sessions for Joanie and herself which fulfilled several fantasies for them both. Complete costumes, props and help with makeup created the illusions Joanie had craved for years. The photos of her as a beautiful bride were amazing as were pictures of her as a cheerleader, sexy boudoir style photos, runway model and Las Vegas showgirl. The sexy ‘Joanie as a nurse’ photo was good but not on the same level as the others. Emma had ordered the same photo fantasies for herself.

The final photo session consisted of a few staged soft-porn Lesbian girl-on-girl scenes of them both. For an extra fee the studio filmed a 4 minute video. The entire process was very erotic for the two beautiful women. Joanie had to work very “hard” at remaining flaccid for the entire shoot. The session was time and money well spent. Glorious pent up relief came afterwards when they got back to their cabin.

The end results were amazing. The pictures and video would be a source of visual memories and stimulation they would enjoy forever. They were in a special photo album from the cruise photo studio. In gold embossed letters the album was titled: “A ‘Trans’ Caribbean Cruise”.

The social events and dinners made them new friends. One couple, Jan and six foot tall Jill, invited Emma and Joanie back to their mini suite to get better acquainted. The couples eagerly shared some of their personal details and experiences. Before the night was over they were all stripped down to their lovely lingerie. The lingerie comparisons gradually evolved into a more adult form of sharing. It turned out that the foursome had a lot in common. Halfway through their get acquainted session Jill had to call room service for more towels, linens and champagne. All agreed that the cruise would never be forgotten.

On the second day of the cruise they went for a mani/pedi session (their nail extensions were beautiful), followed by a hair salon appointment. The hair salon did wonders for Joanie’s appearance. Joanie was initially apprehensive about the way they had thinned and arched her eyebrows but Emma convinced her to relax and go with the flow. Joanie was so relaxed that she agreed to have blonde highlights added to her hair. She was easily enticed into getting an additional ear piercing. The pearl stud, contrasting with her three inch gold hoops, added to Joanie’s look. A full body wax and hair removal treatments fulfilled another long standing desire for her.

The two of them talked about getting matching navel piercings but decided against it while on a cruise. There was swimming and Jacuzzi time that they would have had to avoid while their piercings healed.

Other memorial moments of the cruise for Joanie were relaxing in the swimming pool in her one piece swim suit in plain view of everyone. The fact that there was no judgment or giggling by guests or crew was exactly what she needed. The resulting tan lines were an added bonus.

And there was the after dinner cocktail party with a live band where Emma and Joanie slow danced while wearing their identical little black dresses. Emma snuggled on Joanie’s neck as they made their way around the dance floor. Later in the evening, and after a couple of Mai Tai’s, they kicked off their heels, leaving them under their table, and glided to the music. It was a blissful time. A casual observer would have wondered about all the pretty ladies dancing together.

Not on the ship’s agenda were the intimate times that Joanie and Emma had spent in their stateroom and private balcony. The sense of freedom was fantastic.

When the cruise began it was John who had nervously walked onto the ship with Joanie in a suit case. When they disembarked ten days later it was a beautiful Joanie in a flirty yellow sundress, and her equally pretty girlfriend, that confidently strode down the gangway and onto the dock. Her matching straw purse, sun hat and oversized tortoise sun glasses were a nice touch. She was smiling humming Lou Reed’s ‘Walk on the Wild Side’ as they left the ship. These pleasant shared memories would last forever.

Next – Chapter 2: Back to the closet

(Authors like comments and constructive criticism. Please leave a comment. Thank you.)

A lifetime of reflections, Joanie’s final purge: “You Hook My Bra and I’ll Hook Yours”

Our story follows Joanie from a confused childhood to her Golden Years. Joanie reflects on the events and quirks of fate that led her to becoming Joanie. At 72 years of age, flashbacks and self reflection, allow us to better understand her lifelong search to understand ‘how’ and ‘why’. “Why me?” she asks.

(This story is semiautobiographical adult fiction. Explicit content. There are six chapters. All rights reserved. Comments are appreciated.)

The story jumps around a bit but that’s what can happen in your Golden Years; that’s also what happens when you condense so many years into a brief snap shot. Indulge Joanie a bit and appreciate her story, appreciate her life. You may have many things in common with Joanie.

Chapter 2 of 6

Our story follows 72 year old Joanie from a confused childhood to her Golden Years. Joanie reflects on the events and quirks of fate that led her to becoming Joanie. Her story culminates in her final purge.
Joanie explains how it began; being an only child and being raised by a single parent you need to sort things out.

Previously

When the cruise began it was John who had nervously walked onto the ship with Joanie in a suit case. When they disembarked ten days later it was a beautiful Joanie in a flirty yellow sundress, and her equally pretty girlfriend, that confidently strode down the gangway and onto the dock.

Chapter 2 - Back to the closet

Being Joanie on an almost full time basis had become easier and more frequent since the passing of her wife and love of her life, Emma. 52 years make for many adventures and fond memories. Some of the items Joanie was letting go were sexy lingerie sets she had received as birthday and Christmas gifts. As she sorted and culled clothes and shoes she found herself holding an item to her breast, closing her eyes and reminiscing. A certain blouse or camisole might have a lingering hint of perfume and Joanie would inhale and savor the memories. One particular royal blue garter belt made her smile. Joanie put it in the ‘keep’ pile. An occasional tear would slide down Joanie’s cheek as she determinedly went through with what needed to be done. Not all the tears were tears of sadness.

Reaching for yet another Kleenex Joanie blotted her tears and removed a wad of mismatched nylon stockings from her foot locker. She shoved them into a lawn & leaf trash bag. The nylons joined a well worn 15 inch length denim mini-skirt, a couple of blouses, an old panty girdle and a few other feminine items that had assisted John’s frequent transformations into his femme alter ego “Joanie” over the past 67 years.
Pausing a moment Joanie retrieved the denim mini-skirt from the discard bag. She was recalling how nice her nylon clad legs looked while wearing that skirt. Recalling the many walks with her Emma while wearing that skirt Joanie placed it atop a growing pile of “keep” clothes. Joanie checked the skirt pockets and found an old movie ticket stub that was still there.

The movie ticket stub was from a sentimental chick flick movie she and Emma had attended a few years ago. Joanie recalled being very nervous about being out in public. Emma had held her hand and it helped Joanie to relax and walk into the theater. Emma was thoughtful enough to have bought their tickets.

Joanie remembered how they had both cried at a couple of the more tender scenes. They shared tissues from Joanie’s purse to wipe their tears. Emma had gently rubbed her nylon covered knees in an effort to sooth her. Joanie could remember the movie but couldn’t recall the name of the movie. Getting older has a way of robbing a person of details. At home, later that night, the sex had been particularly great. It must be true that you remember the things that are important to you.

Delving again into her ‘hobby box’ Joanie pulled out 3 rather well worn bras. One was a purple 38 B underwire, one was a turquoise push up Wonder Bra and the other was a black wispy sleep bra. The elastic in all bras was old and stretched. She removed a bra extender from one bra, placed it in her romper pocket, before placing them in the waiting trash bag.

A drawstring make-up bag was the next item she removed from the old locker. Opening the bag Joanie emptied the contents into the trash bag. There were the usual items that you’d expect to find in a woman’s purse or on her vanity; mascara, fine tipped brushes, false eyelashes, several well used pallets of eye shadow and several other expired cosmetics. All went into the trash bag.

Spying a familiar tube of lipstick Joanie pulled it out of the discard bag and pulled the top off. She extended the lipstick and inhaled a pleasant memory from days gone by. Using a small makeup mirror from her cosmetics discards she used it to apply a coat of her favorite color to her lips. She pressed her lips together to even out the color. Joanie retracted the lipstick, replaced the cap and added the tube to her romper pocket. It’s difficult to let go of fond memories or a good lipstick. The aroma and flavor caused a familiar and pleasant stirring in her crotch.

Joanie grabbed a pair of well worn open toed silver lame wedgies and carefully placed them in her goodbye bag. The shoes made her recall a business trip to New York City, over 40 years ago, where she made a point of visiting a famous specialty boutique that catered to transgendered and cross-dressing clients; Lee’s Mardi Gras Boutique. Finding a woman’s shoe that would fit her size 13 wide foot had been difficult. None the less her search for a shoe with a proper fit had been fun. There were so many other items to see and explore; wigs, gaffs, false eye lashes, fetish clothing, literature, erotica and sex toys.

Retrieving a pair of shiny black, 3 inch heeled pumps she smiled. The shiny pumps were one of Joanie’s prized items. Images of her tottering around the house, while practicing to walk in them, came to mind. Smooth hard floors were easier to walk on than soft carpet. It was a wonder that she hadn’t hurt herself. She had bought them from a web site promoted on her favorite TG/CD/Alternate Lifestyle web site; Big Closet Top Shelf.

Retrieving a black thigh high nylon from his discard bag Joanie removed her gold anklet and effortlessly pulled the stocking on. She put the ankle bracelet back on over her stocking and slipped a high heel onto her right foot and extended her leg in a manner that gave her the best view. She wiggled her ankle and smiled as she admired what once was her favorite femme shoe. Pulling her foot back she removed the ankle chain, the pump and nylon and placed them both in the bag.

“Dang”, she lamented, “I wish I knew someone to give these things to”.

Peering into her secret stash Joanie gathered up a medium size wad of lingerie. Quickly sorting through the clump of clothes she set aside a pair of peach colored nylon tricot pettipants, one pair of sexy tap pants that had delicious lace trim and a rather attractive but very short half slip; all of these items had been frequently worn by her under her male clothes over the years. It’s difficult to get rid of ‘old friends’ and besides she thought she should be able to get a little more use from them. She placed these items in a growing “keep me” pile.

Peering again into the footlocker Joanie’s eyes lit up as she retrieved an old photo album. The album was marked “A ‘Trans’ Caribbean Cruise”. Holding the well worn album brought a smile to her face. Wanting to spend some time with her deceased wife Joanie stood up and brought the photo album to her writing desk for a proper viewing. Joanie lingered and savored each page. Time seemed to stand still.

To get a better understanding of what Joanie was dealing with it would be best for Joanie to explain how she found her feminine side and accepted Joanie.

Flashback – Over the years

Joanie explains

My "hobby" began when I was 3 or 4. My parents divorced and mom had fled from suburban Minnesota to the big city of Kansas City I the mid 1950s taking a job as a waitress at The Copper Kettle Café in order to support the two of us. Coffee was .10 cents a cup and her tips were small. I had no siblings.

Home was a twelve story hotel. I recall my mother occasionally painting my nails after she had painted hers. I’d sit, fascinated, watching her get dressed and do her makeup as she got ready for work. Maybe these daily observations were the beginning of my interest in girly things. Leaving for work she’d drop me off at a babysitter.

The young girl next door to my sitter was my age and always wore pretty skirts and dresses. They were always colorful and much different from what I wore. When the young girl would run or twirled around her dresses would billow like a parachute. Her dresses and skirts looked like fun to wear… unlike the jeans and t-shirts I wore. I wanted to wear what my playmate wore.

One day I asked my baby sitter if I could wear a dress too. I was told no. I asked again and added “pretty please’ to my begging. I was denied again. I persisted in what I thought was a simple request. On the third day I begged for her to let me wear a pretty dress. Shortly after being dropped off at the baby sitter on the fourth day of my quest the sitter called me into a bed room. Displayed on the bed was a beautiful blue dress! It was just like what the girl next door wore. It was just what I desired. It tied in the back and it had a bow. My sitter told me that she’d help me get dressed but she admonished me with “Don’t tell your mother.”

I rushed to the bed and picked up the object of my desire. I had no way of knowing that dresses and all things feminine would become a lifelong desire. Is this when I became infatuated with girl clothes? As I aged I’d always wonder ‘WHY’ and ‘WHEN’.

In a flash I had shed my jeans and t-shirts and was finally wearing my first item of girl clothes. I was ecstatic as a young boy could be. It was like getting your first puppy. I skipped and I hopped and went about my day as usual. They only difference was that I was not allowed outside wearing the dress. I didn’t understand why. This secrecy about wearing clothes of the opposite gender was with me, and haunted me, for most of my life. Apparently me wearing dresses was to be kept secret.

As I grew I knew I was a bit "different" with my interest in girl’s clothes, make-up and nail polish. “Girl” is what I wanted to emulate. Maybe I actually wanted to “BE” that girl. I knew girls were different. Perhaps I thought their life was better than mine. Perhaps I thought dressing would make me feel happier. At such a young age who really knows “why”? So why not join their club; even if it was only occasionally and part time. The search for “why” would never leave me.

“Do what you can, when you can”. It’s better than repressing your need to be “you”.

At such a young age you go with instincts; base instincts. I was too young to have formulated anything about such advanced concepts like social norms or gender norms; concepts of shame, embarrassment and being gender ‘wrong’ were just making themselves known to me. All I knew was don’t tell mom. Don’t tell mom evolved to ‘don’t tell anyone’. Secrecy became important.

I played cowboys & Indians with other 6 year olds and was glad when I could wear the cowgirl skirt, vest, red boots and cowgirl hat…we all loved and watched the Roy Rogers & Dale Evans TV show. I recall wearing a ‘poodle skirt’ when playing house with my playmates. It wasn’t a problem for them. I soon found out that it was a problem for the adults.

“Boys don’t wear that… boy’s don’t do that… Good boys don’t…” And there are consequences if you do. Some consequences are subtle. Some aren’t so subtle. It became clear the idea was ‘do not get caught’.

Elementary school had me investigating and enjoying nail polish and lipstick. I used crayons and colored art pencils as nail polish. More than once I had to explain away to my mother and friends that my slightly colored lips were due to popsicles.

Mom remarried and we moved to sunny and warm Southern California. I was the new kid in town and was desperate to make friends and become accepted by my peers. While searching for friends I meet Michelle.

Next – Chapter 3: Some boys do! (Not work place safe)

(Remember authors like comments and constructive criticism. Please leave a comment. Thank you.)

January 2019 "Reader Retention Contest"

(This story is semiautobiographical adult fiction. Explicit content. There are six chapters. All rights reserved. Comments are appreciated.)

Chapter 3 of 6 (Not work place safe)

Our story follows 72 year old Joanie from a confused childhood to her Golden Years. Joanie reflects on the events and quirks of fate that led her to becoming Joanie. Her story culminates in her final purge.

Have you ever been the ‘new kid’ in school, feeling alone and in need of a friend? I find Michelle and Michelle finds Joanie. It was a summer of discovery that I’d never forget.

Previously

Mom remarried and we moved to sunny and warm Southern California. I was the new kid in town again and was desperate to make friends and become accepted by my peers. While searching for friends I met Michelle.

Chapter 3 - Some boys do!

Throughout elementary school I had acquaintances but never had a close friend or buddy.

In junior high school, during the early 1960s, I found a friend who was more involved with his feminine side than I was. Mike also was an only child. He was a year older than me. We were the same height. His single mom was raising him by herself and worked 10 hours a day trying to make ends meet. As a result Mike was left unsupervised most of the time and he had found unique ways to occupy his time. He could be called a ‘latch-key kid’. Since Mike lived only two blocks from me he and I became buddies. It turned out we had at least one thing in common. We spent a lot of time together.

I happily discovered that I was no longer alone with my ‘weird desires and thoughts’! I watched as Mike applied lipstick, painted his nails, dressed in his mother’s clothes and wore her shoes. With my very willing participation I let him paint my lips with his mother’s lipstick (“Cherries in the Snow”). Since Mike’s nails were painted (and looked pretty) I let him shape and paint my nails too. The polish matched my lipstick. This day was a very big step in my life; it impacted my life forever.

I was cleaning my finger nails before going home when Mike suggested that I leave the polish on my toes. “We’ll be The Pretty Nails Club” he quipped. “Just keep your socks on around your parents.” Mike was a gentle soul and would become a mentor to me in more ways than I could have ever imagined.

The next day I returned to Mike’s house or Michelle as she called herself when in femme mode. She was already wearing tan colored pantyhose, a laced trimmed yellow bra, lipstick and nothing else. No panties allowed me to see her flaccid cock. She had several bracelets on her right wrist. I was clearly intrigued by what I saw. All her nails were a bright red again. “Wow, your legs look so nice” I said. I was talking about legs but was staring at her penis. Michele noticed my staring and smiled. “Yes, legs and dicks do look nice with hose and they feel even better to the touch. Nylons with heels make legs look even nicer. Care to try a pair?” she asked.

Without hesitation I enthusiastically said “Oh, yes that would be great!” Michelle said “I’ll show you the proper way to put on stockings. Remember that you can’t just tug them up your legs. There’s a method you need to follow. First you must roll them up in a special way before you begin to put them on or else you’ll rip them. Before we begin you need to slip into some proper panties and a bra. You should never wear hose without panties.” Michelle handed me the lingerie she wanted me to wear. They were bright red.

As I was shedding my jeans, t-shirt and boys underwear Michelle tossed me a tube of his mother’s lipstick and told me to put some on. I did. Oddly enough the red color matched my borrowed lingerie. I was struggling with my bra when Michelle came over, adjusted the straps and hooked me up. Stepping away she playfully snapped my bra strap. “You can do the same for me someday. Remember you hook my bra and I’ll hook yours. That’s what friend’s do.” she quipped.

Standing in only panties and bra, as instructed, Michelle looked at my feet and commented “I’m glad you left your toe nail polish on since it matches your panties and lipstick”. I’m not sure why but I was glad that she had noticed. “Let’s go into my bedroom so we can get you into some pantyhose”.

I had watched my mother put on her stockings many times before. I knew how it was done yet I said nothing. I willing went into Michelle’s bedroom.

Michelle had me sit down on the edge of her bed. Michelle sat down next to me; she held a pair of sheer black pantyhose that she had rolled up in a special way. Extending my left leg and pointing my toe as she requested, Michelle leaned over and positioned one leg of the hose on my left foot. She began rolling the nylon up my leg to just below my knee. “You got to do a little at a time. Don’t be in a hurry if you want to have pretty smooth legs. Now extend your right foot”. Michelle repeated the process and stopped when this hose was in the same place as it was on my left foot. “Carefully stand up, turn around and face me” she instructed. Michelle remained seated.

I stood and made a hobble turn hop and was standing facing Michelle. “Come closer” she beckoned. Her voice sounded different; almost sultry. I was standing between her legs and my panty encased pelvis was level with her face. The nylons were bunched around my ankles. Michelle blew a prolonged but steady stream of air directly onto my panty hidden crotch. I felt her warm breath and my penis began to involuntarily swell, my mouth became dry and I felt lightheaded for an unknown reason that my young brain didn’t fully understand. Michelle stared straight ahead. She blew again. Without looking up, and while staring at my panties, Michelle softly said “Here comes the fun part. You need to slowly and evenly pull your hose up each leg like this”. Following her own instructions Michelle bent over and expertly rolled the hose the rest of the way up my legs. Black nylons contrasting with red lingerie are a beautiful sight.

Looking up and into to my eyes Michelle said “A proper girl needs to smooth out her hose. Wrinkles aren’t lady like.” While maintaining eye contact Michelle used both hands to slide and smooth the wrinkles from each leg. She began at my ankles and drew her hands upward. Her hands were so gentle. It felt great to have someone caress my legs.

The feel of the nylons combined with her touch had my knees quivering. Michelle stood up and we were belly button to belly button. She smiled at me charmingly and said “You need to make sure that the rest of your pantyhose are smooth; not just your legs”. Using an open palm she began to slowly stroke my crotch in slow repeated upward movements as if she was petting a cat. It felt so good that my breathing became more rapid and my knees became weaker.

“Look how I’m smoothing your nylons. See how much better they look now? It feels nice for me to smooth your nylons doesn’t it?” I broke eye contact and looked down. I was barely able to gasp out an agreement. I nodded my head and demurely said “Yes, my nylons look much nicer and yes, smoothing them feels incredible.” I was panting with pleasure by now. Michelle stopped her stroking but left her hand on my well defined lump. I was in heaven.

Speaking softly Michelle pointed out that it appeared that her nylons weren’t smooth all over either. I took the bait and reciprocated with the same smoothing and stroking of her nylon covered crotch. I could feel the heat and firmness of her cock through her panty hose. My penis twitched. So did Michelle’s. It felt delightfully naughty. I let my hand linger on her bulge enjoying a new experience; my first cock. She pressed my hand more firmly to her penis. On purpose Michelle made her dick throb making sure that I felt it.

Without stopping her ministrations on my boy bulge Michelle leaned forward and kissed me. I could taste her lipstick. She gently caressed the length of my cock several times from the outside of my pantyhose. I made my dick throb for her. It was all so very pleasant. My penis was beginning to protrude above my hose. As I reciprocated her kiss Michelle pulled my pantyhose and panties forward enough to be able to run her thumb tip around and around the pee hole of my raging hard-on. It was yet another first for me. It appeared I was leaking something. I was naïve about preseminal fluid. Whatever it was it made Michelle’s rubbing of my cock head more slippery and more erotic.

Reaching deeper into my panties Michelle grabbed and hefted my ball sack. She briefly and gently massaged my balls. Releasing my balls Michelle encircled my dick with her warm hand and gripped it snuggly. Using her thumb again Michelle began doing what she knew would give me the most pleasure. Her snug grip was warm and affectionate. By reflex I reached into her panties and grasped her cock. Whatever Michelle would do I would reciprocate. I found her wetness. She gasped and leaned a bit closer. We continued to make out.

Michelle then grasped my penis like you would hold a coke bottle and began to slowly and gently stroke my shaft up and down being sure to spread my wetness along my shaft. Her stroking felt nicer. I returned the favor. We may have been standing there for hours for all I knew. What I did know is that I didn’t want the moment or the slippery sensations to stop. It was a new and beautiful thing.

Michelle broke our kissing and pulled me onto her bed. I didn’t resist. Sitting on her bed she kissed me again but this time she inserted a little of her tongue into my mouth. Her tongue probed. My body quivered and I tongued her back. Our tongues entwined. I thought the day couldn’t get any better as I was experiencing yet another, incredible, first. I squirmed a little and she gently laid me back as she straddled me. Lying on top of me she ground her nylon covered crotch into my nylon covered crotch. The slow humping and rubbing made my dick harder than it had ever been before. I experienced lust and desires that I never knew existed. Both of us wearing pantyhose made it all the more erotic. In retrospect I think that made me Michelle’s ‘bottom’.

Michelle stopped kissing my lips and lifted my bra for ease of access. Her mouth and tongue moved to my nipples. She sucked, nibbled and kissed each of my nipples into a delightful hardness. I loved it then and I still love it today!

Next - Chapter 4: Michelle straddles me (Not work place safe)

(Remember authors like comments and constructive criticism. Please leave a comment. Thank you.)

A lifetime of reflections, Joanie’s final purge: “You Hook My Bra and I’ll Hook Yours”

Our story follows 72 year old Joanie from a confused childhood to her Golden Years. Joanie reflects on the events and quirks of fate that led her to becoming Joanie. Her story culminates in her final purge.

Have you ever wanted to take a less traveled road? Have you ever regretted not taking a different route or trying something different? Michelle showed me the way; I have no regrets. Over the years I have wondered where and how she got her ‘road map’.

(This story is semiautobiographical adult fiction. Explicit content. There are six chapters. All rights reserved. Comments are appreciated.)

Chapter 4 of 6 (Not work place safe)

Previously

Michelle stopped kissing my lips and lifted my bra for ease of access. Her mouth and tongue moved to my nipples. She sucked, nibbled and kissed each of my nipples into a delightful hardness. I loved it then and I still love it today!

Chapter 4: Michelle straddles me

Michelle stopped and sat up still straddling me. Her butt was just below my knees. Maintaining eye contact Michelle hooked her thumbs into my pantyhose and panties and with surprising expertise she pulled them both down to knee level in one swift move. My cock waved in her face.

Reaching over to her night stand Michelle retrieved her tube of “Cherries in the Snow” lipstick and, while I watched from below, she made a show of applying it to her lips. Without asking she leaned forward and began coating my lips like she had the day before. I pursed my lips to make it easier for her. When she was satisfied she returned to an upright position and put the shiny gold tube back on the nightstand.

Michelle smiled and reached out and gripped my waiting penis. She gave it a few strokes as if she was trying to milk me. “Why did you need your lipstick?” I breathlessly gasped. Without missing a stroke she grinned and said “Watch and learn.” She leaned forward and kissed the tip of my dick making sure to leave a lipstick print. She kissed my cock head again and ran her darting tongue along the underside of my shaft. Her next move was to engulf my dick with her mouth and begin a sensual sucking and milking motion while tonguing my shaft. I literally swooned and may have temporarily blacked out.

Michelle kept doing what she obviously wanted to do. She bobbed her head up and down to her own rhythm. She kept a nice seal with her lips. The object of her desires popped free with an audible ‘pop’ sound. After she had dampened my shaft to her satisfaction she dove deep and pressed her lips tightly at the base of my shaft. As she withdrew, milking me with her soft but firm lips, she purposely imprinted two more color rings on my dick. One ring was right below the corona. She made me groan with a pleasure I had never felt before.

Popping free she sat up and proudly pointed at my shaft. “You asked about the lipstick. Check the love rings I gave you. I was marking territory!” She giggled as I raised my head off her pillow and looked. Indeed there were very well defined red rings circling my dick at various places. Michelle looked so proud. My head collapsed back onto the pillow. It was all nice but somehow I felt a little let down by this fantastic first experience. It was as if I was missing out on something. I grabbed my dick. My pretty red nails looked so sexy wrapped around my shaft. I began the same stroking moves that Michelle had just introduced me to. I felt like I needed to finish something but I didn’t know what.

Michelle slapped my hand away went back to licking, sucking and milking me with her warm soft mouth. I felt ‘something’ building deep within me, something I had never felt before, something that I needed to have. Michelle added a new twist to my enjoyment as she continued to bob; she tickled and teased my anus with her index finger. Adding some of the love slime from my dick to lubricate her finger Michelle began to wiggle her finger firmly into my virgin hole while continuing to fellate me. She made it to her second knuckle, and began using an in and out fucking motion going as deep as her finger would allow. I was being finger fucked. It felt so good. I gripped her finger and curled my toes. My clenching didn’t slow her down. Michelle bobbed her head and swirled her tongue until I convulsed in what was my first orgasm. I felt myself squirting. Each squirt caused another convulsion which caused another squirt. It was deliriously delicious. It was a beautiful thing!

I heard another popping sound as Michelle uncoupled from my glistening penis. Looking up at Michelle I saw that her cheeks were slightly bulging. I was so very grateful. Michelle immediately leaned forward to kiss me and I anticipated more kissing and tongue. I was ready I thought. Pressing her lips to mine I felt her tongue and I lightly sucked it into my mouth. As Michelle pressed her lips more firmly to mine I felt her slowly transfer warm sperm that she had just drained from my dick into my mouth. I found myself with a mouthful of my own sperm. That action caused me to reflexively squirt again. I swallowed. Michelle had saved some for herself. She nudged me and made a point of letting me see her swirl it around in her mouth before swallowing. She kissed me again.

My sperm didn’t taste bad and I tongued her deeply looking for more. Using my tongue I coated my lips with my own essence. My penis and I went totally limp. I lay there, staring at the ceiling, feeling exhausted but feeling complete. The final post orgasm feeling of bliss is what I was missing just minutes earlier. I had found something very special. I no longer felt unfulfilled. Michelle lay next to me.

After a few minutes of rest and reflection Michelle sat up. “Did that feel good?” she asked. With no hesitation I said “That was a beautiful thing”. Michelle smiled, retrieved her lipstick and removed the cap. She looked at it for a short while and began to slowly stroke her penis into a very fine erection. She stopped the stroking and pressed the tube into my hand. “Here, let’s see what you can do.”

I sat up and smiled. I gently gripped her hardness and gave it a few loving strokes. It felt good in my hand. I applied a liberal coating of color to my lips and replaced the cap on the lipstick. Handing it back to Michelle I shifted to a better position. I first kissed her on the lips, probing her mouth with my tongue as she had done. I then kissed the tip of her cock being sure to leave a bright red imprint. I took hold of her penis, pulled it to me and sealed my lips firmly just below her corona. I slowly sucked her dick deeper into my mouth being sure to wet her shaft with my tongue. Michelle groaned in appreciation and I began marking my own territory.

Fully satiated a half hour later we found ourselves lying in bed holding hands enjoying a special glow of contentment. “You did extremely well for a beginner. I’d never have guessed this was your first time performing a blowjob. And you swallowed. It was great. Thank you.” “I noticed one thing Michelle; your sperm tastes different than mine” I said. We giggled a bit. “We best clean things up as your mom will be home in an hour.” We did. As I was about to leave I had removed the pantyhose and bra when Michelle said “Keep the panties but wear them the next time you come over. I have a lovely skirt that I want to see you in. Mom has a couple of old wigs that we should try.” I agreed.

Just before I left Michelle said “The name John really doesn’t suit you after today. You look and behave more like a Joanie. May I call you Joanie during our special times?” I thought a moment and with a big grin I said “Yes, Michelle. Joanie sounds pretty and girly. Call me Joanie. I’d like that.” I walked over, kissed her and left.

Michelle and I spent summer afternoons painting each other’s nails, trying on her mom’s dresses and skirts and experimenting with makeup and eye shadow. I became comfortable wearing high heels. Michelle taught me how to slow dance. We perfected individual and mutual masturbation. Her bracelets sounded like sleigh bells as she stroked herself or me. It was a landmark year in many ways. I had found a ‘sister’ that shared my secret desires; desires I didn’t know I had. I discovered a sense of girly fashion and feminine mannerisms that has served me well. I also became proficient at sex. I learned from Michelle that wearing lipstick while performing a blowjob acts as a lubricant while bobbing up and down a firm shaft. It also helps prevent chapped lips.

Many times after a love session we showered together. The first time we showered together was because Michelle said we needed to get the bright red rings off our dicks. She would soap and wash my shaft and then I would soap and wash her shaft. Of course it was a lame excuse but I was an eager participant. During one shower session I suggested that maybe I could remove her love rings using only my mouth and tongue. I found myself on my knees giving Michelle one of the best blowjobs of my young life. It didn’t work but it was exciting to try. It became a routine thing.

Michelle suggested that we needed to keep our backsides and ‘rose buds’ squeaky clean which led us to incorporating digital penetration in to our repertoire. That process led to other things and it was in a comforting warm shower that I lost the last remnant of my virginity. It was a beautiful thing.

After each love session, prior to leaving for home, Michelle would always give me two mints to take with me. “You wouldn’t want anyone to smell me on your breath, would you?” The mental image of mom smelling my breath and asking “Is that sperm I smell?” always made me laugh.

Michelle was a very special person in my life and I’m grateful that we met. She taught me so many things other than makeup application and removal. Michelle was the cause of my first wet dream. Even as I slept my Michelle had an effect… a pleasant, sensual effect.

Regrettably my step dad took a job with a new company and my family moved to another town leaving my lovely Michelle as a beautiful memory. We swore we’d stay in touch but sadly that never happened. As parting gifts I gave her two pair of slinky shear black nylons and a gift card to Ulta cosmetics. Michelle gave me a lovely pair of crème colored tap pants, a tube of lipstick and a tin container of mints. I recall her saying that they might come in handy some day.

We had kissed goodbye and as I was about to leave she handed me a small gift wrapped package. “Open it now.” I took her gift and tore off the wrapping. It was a sleek, five inch, battery operated, two speed vibrator! “When you miss me use this and think of me and all our good times.” She kissed me tenderly on my cheek; tears were running down her cheeks as I left.

I thought I would never have sex again. I was wrong. While at a mountain summer camp near Big Bear Lake a few months later, while feeling lonely and missing Michelle, I allowed a handsome older camp counselor to entice me into the forest. Afterwards, when I returned to my cabin, I immediately popped a mint into my mouth, applied chap stick and began tweezing pine needles out of my knee caps.

NEXT - Chapter 5: At Home: Joanie reflects

(Authors like comments and constructive criticism. Please leave a comment.)

Chapter 5 of 6 (Not work place safe)

Our story follows 72 year old Joanie from a confused childhood to her Golden Years. Joanie reflects on the events and quirks of fate that led her to becoming Joanie. Her story culminates in her final purge.
Have you ever taken the road less traveled road? Joanie reflects on how she evolved, on her first purge and how she became a living dress form.

Previously

I thought I would never have sex again. I was wrong. While at a mountain summer camp near Big Bear a few months later, while feeling lonely and missing Michelle, I allowed a handsome older camp counselor to entice me into the forest. Afterwards, when I returned to my cabin, I immediately popped a mint into my mouth, applied chap stick and began tweezing pine needles out of my knee caps.

Chapter 5 - At Home: Joanie reflects

During middle school my mother occasional used me to stretch her new high heels. Too tight on her my feet fit her heels fairly well; her heels just needed to be broken in. My after school assignment was to wear her heels around the house while watching TV, going to the kitchen, to the bathroom, etc. I’d break-in her new shoes until they were comfortable enough for her to wear them at work. In fact wearing her shoes was educational and exciting to me. I didn’t complain.

I discovered that thin nylon ped socks or knee high nylons were needed in order to slip into mom’s shoes. Imagine that! I “needed” to wear nylons. Michelle would have been proud of me. I have to agree that I was truly fortunate. It was Michelle and mom that helped Joanie develop as a young woman.

Mom used to sew and mend her clothes in her youth. She used a sewing machine and made clothes from Simplicity patterns. We were about the same height so I became her living dress form as she adjusted her hems or tried a new pattern. She used straight pins, a tape measure, scissors, tailor chalk and me. I didn’t complain.

To make sure her skirt hems were straight and level when she wore heels I also had to wear high heels as she finalized the hem length of her skirts and dresses. If heels were not worn then the hemline would be off… I was told. It seemed reasonable to me. Again, I did not complain.

While she was working on a pretty ‘top of the knee’ dress mom was having difficulty in getting the darts of the breast area correct. It seems my flat chest wasn’t helping her project. Taking a break from her efforts she told me to relax while she had a cup of coffee in the kitchen and collected her thoughts. While she was in the kitchen I went to her bedroom and put on a blue underwire demi bra that I just ‘happened’ to know would fit me. I stuffed the cups, as usual, with some of my socks and went back to the den to complete my dress form duties. Standing in high heels and nylon stockings, while wearing a bra and dress, truly thrilled me. Somehow it made me feel complete.

Returning from the kitchen mom paused as she noticed my new endowments. She looked me up and down while collecting her thoughts. After a few moments she commented, “I think you saved our project.” She made no other comment. Having me wear a bra became a regular part of her seamstress projects. I became very proficient at tucking my male bulge. Michelle would have been proud of me. I often wondered what mom must have thought about the initiative I took. I also wondered why I didn’t have the courage to dress like that when not being a human mannequin. Life has regrets.

Based upon my experience wearing mom’s and Michelle’s 4 inch heels is why, later in life, I bought sensible black pumps with only a 2 ½ inch heel. (Thank you mom, thank you Michelle) After age 55 I switched to a more practical, more stable ‘chunky’ heel rather than the traditional spike heel.

A need for Joanie to look more girly

It was during eighth grade that I realized that my ‘boy’ eye glasses distracted from the girly image I desired. I plotted on how to obtain a prescription set of cat eye ‘girl’ eye-wear. I knew I could steal the frames but how could I get prescription lens? In eighth grade I got contact lens! Problem solved! My female self image took a large boost. My first contact lenses (mid 1960s) were hard, rigid and tough to get used to. My parents were amazed at my dedication to getting used to them. The desire to appear more feminine is a fantastic motivator to a young cross-dresser. I made the lens work and was ecstatic that I had them.

During my high school years Avon Cosmetics sold make-up door to door and always left several mini sample tubes of lipstick, makeup and a catalog. Oh, how I looked forward to their visits and freebies. It gave me a chance to experiment with flesh tones and lip colors. I went through a phase where I’d wear two different colors of lipstick to create a color that was uniquely mine. A white lipstick with a darker color on top of it makes for an interesting shade. You should try it sometime.

The Kinks classic song “Lola” and The Beatles “Get Back” became my personal anthems.

Live and learn

While babysitting one time, when the kid was asleep, I tried a neighbor’s bright red lipstick. It really looked cool on me but I didn’t like the smell or taste. I thought it made me look too slutty. It was then that I realized that I was a Revlon Super Lustrous Moon Drops sort of girl which smells and tastes great. After a couple hours of wearing the red, and just before the parents were due home, I diligently went to remove the lipstick. It would not come off! It would come off a little but the red stain remained. I was panicking.

I retrieved the lipstick and read the label on the bottom of the gold tube… it was a “Long Lasting 24 Hour” type of lip color! Oh, my God! I used soap and water and I finally used cold crème like Michelle had taught me. I can truthfully say that I don’t like the taste of cold crème. I rubbed, scrubbed and repeated. I rubbed my lips raw but finally, just in time, dulled the color to a passable normal boy lips. Damn that was close.

During high school I evolved to more frequently wearing bras, panties, panty girdles (with nylon stocking ready garter clips) and nylons/pantyhose in general. Considering that mom had found it perfectly fine for me to be her living dress form and shoe stretcher I found no problem in borrowing her clothing, lingerie and cosmetics. Summer vacation from school gave me eight hours to be Joanie while my parents were at work.

There was a lazy summer day, when school was out and the folks were at work, that I put on a pair of panties, pantyhose, painted my finger nails and colored my lips. I went about my day feeling pretty and feeling special. I had eight hours to do and wear what I wanted. I spent the day applying and reapplying a variety of pretty lipsticks and nail polishes. I cleaned my nails and just before mother got home from work I cleaned my lips with wet tissue, soap and water. I tossed the stained tissue in the toilet but forgot to flush the evidence.

Later in the evening mom called me into the bathroom and asked me about all the red stained tissue in the toilet. I thought I was going to die from fear and embarrassment. Looking into the toilet bowl I tried to sound unconcerned and said “Oh, I painted a model car and cleaned my brush”. She looked at me closely and reached over and flushed the toilet. “Flush next time” is all she said. Did she believe me? Probably not. But she didn’t say anything more, didn’t make a fuss or worse of all, and didn’t mention it to dad.

On yet another occasion my lips were sporting a bit of color when mom got home and I was asked “What’s that color on your mouth?” I explained it away as being from a cherry Popsicle.

Dad came home early one day and I had to quickly pull on my Levis to hide my hose. I wasn’t wearing socks to cover the easily visible reinforced toes of my nylons, just tennis shoes. If he noticed my taupe stockings he never said. I guess that's part of the excitement. It was about this time in my life that I discovered that if your wear two pairs of stockings/pantyhose that your hairy legs go un-noticed when wearing a skirt or dress. The sensations and feeling of sliding on a pair pretty lace trimmed panties or pettipants on top of hose was always exquisite. Pettipants, or slip pants as they are called now were perfect for me.

First purge

It was in 10th grade when I had my first ‘purge’ of all my girly stuff. Guilt and shame can make a person do lots of things. I tossed Joanie’s clothing collection out and swore I would be a ‘good boy’ and never indulge in cross dressing again. This is easy to say but difficult to do when the urge and need to feel girly runs so very deep. I think this purge compulsion can be traced back to age 5 when I was forbidden to go outside if I wore a dress. “Boys don’t wear dresses.”

From personal experience and research I learned that cross-dressers typically go through a series of “binge and purge” episodes regarding their female clothing stash. You acquire some nice clothing, make-up and literature; you feel guilty, vow to cease and desist and toss (purge) out your collection of feminine things. Then you start all over until the next time. I have gone through this cycle at least three times. But the urge, need and desire to express the Joanie side of me never went away

NEXT - Chapter 6: Conclusion - What am I, will it go away and why me?

(Remember authors like comments and constructive criticism. Please leave a comment. Thanks you.)

A lifetime of reflections, Joanie’s final purge: “You Hook My Bra and I’ll Hook Yours”
(This story is semiautobiographical adult fiction. Explicit content.)

Chapter 6 of 6

Our story follows 72 year old Joanie from a confused childhood to her Golden Years. Joanie reflects on the events and quirks of fate that led her to becoming Joanie. Her story culminates in her final purge.
Joanie gets married, does her military duty, looks for answers and grows old: a final purge

Previously

From personal experience and research I learned that cross-dressers typically go through a series of “binge and purge” episodes regarding their female clothing stash. You acquire some nice clothing, make-up and literature; you feel guilty, vow to cease and desist and toss (purge) out your collection of feminine things. And you always restock.

Chapter 6 - What am I, will it go away and why me?

In high school I began researching the subject of transvestism as I struggled to discover WHAT was ‘wrong’ with me, WHY I had the desire and ‘need’ to look feminine. I was fearful that I was gay. (At least not since tenth grade). What accounted for my desires? What is such a person called? Would I get over my ‘condition’? My research answered many things but it didn’t explain WHY. I accepted the fact that I'm a cross-dresser, always will be and "it" isn’t going away; so I decided to make the best of it! This self revelation made life easier.

Pick a term: Eonism, transvestism, cross-dresser, closet queen, transsexual, transvestite (an out of date term I’ve learned), sissy, deviant, CD, TV, tranny, she-male, he-she, etc. Call me whatever you want it doesn't change anything.
Looking for answers I read every newspaper article that I could find on the subject. Day time TV talk shows introduced me to the Tri-Ess Society. Tri-Ess: Society for the Second Self is an international educational, social, and support group for heterosexual cross-dressers, their partners, and their families. Books on the subject of cross dressing fed my quest to know and understand myself. I continued to wonder “why me”?

“Femininity… is a set of attributes, behaviors, and roles generally associated with girls and women. Femininity is partially socially constructed, being made up of both socially-defined and biologically-created factors. … both males and females can exhibit feminine traits.”

“Traits traditionally cited as feminine … vary depending on location and context, and are influenced by a variety of social and cultural factors…” https://en.wikipedia.org/wiki/Femininity. It’s an interesting piece of the puzzle but it doesn’t give me the “why me” that I was searching for.

Not un-expectantly I have empathy for others, I’m sensitive and I have a gentle side. There’s more to being feminine than clothes, makeup and jewelry.

After my military experience I discovered cross dresser friendly Empathy Press that was based in Seattle. Run by Charles “Cathy” Slavik Empathy Press specialized in a different type of literature; Erotic fiction. I got a PO Box and ordered literature; lots of “literature”. What a shame that the internet had not been invented yet. The PO Box allowed me to order clothes and things easily and anonymously.

Military & marriage

Purge two

Leaving for the military was both exciting and stressful. Prior to leaving home I went through my second purge of Joanie’s things. I didn’t want family to find my panties and nylons. It had to be done. Both of these life events slowed Joanie down a bit but did not scare her away for very long.

Marriage

Emma became the love of my life. I didn’t want to blind side Emma with Joanie and had, over time, left a few conscious and unconscious clues of her presence. There had been a tube of lipstick in my glove box, a lingering bit of perfume on my shirt, a hint of color on my cuticles, my overt appreciation of feminine fashion style, etc. I wasn’t a ‘flaming’ cross dresser but I’m sure I glowed on occasion. A year or so into our marriage Emma confided that when we first started dating that she had definitely felt a bra band under my shirt as we hugged on several occasions and had wondered about the lipstick marks on my coffee cup while visiting me at my apartment.

One evening, while driving to no place in particular, I told her that before we wed that she needed to know about a very special person in my life; a person that would always be in my life but who was no threat to her or our marriage. I parked in a mountain road pullout, shut off the engine, set the brake and turned to face Emma.

Joanie explains to Emma

I explained to Emma what cross-dressing was and who Joanie was. Emma listened intently. I concluded my explanation by showing her a picture of Joanie in full femme that I kept in my wallet. Taking the photo from my hand Emma gazed at it for moment and commented “She’s very pretty. She could be your twin sister.” “She is” I replied. Emma gently took hold of my hand and said “I always wondered why your hands and nails looked so nice. Actually, that’s not true; I wondered why your nails were so well shaped and pretty.” She leaned over, kissed me, and continued: “Thank you darling for confiding in me. I’m sure I can live with that. There’s room in our life for the three of us.”

Emma reached into her purse, grabbed her lipstick, removed the cap, extended the lipstick and asked me to lean towards her. Firmly holding my chin Emma slowly coated my lips with Copper Rose. She then pulled me close and kissed me on my mouth. Emma then touched up her lips and was going to put the tube back into her purse. She paused a moment and then handed me the gold cylinder. “Give this to Joanie the next time you see her. Tell her the color will look nice on her. I’m looking forward to meeting her.”

We were married three weeks later. Throughout our marriage Joanie was never a problem. On our wedding day Emma hooked my bra and attached my nylons to a beautiful Emerald green garter belt that I wore under my wedding suit. The garter belt matched my panties, bra and tap pants. All were a gift from Emma to Joanie. In fact it became a running joke throughout our marriage: “You hook my bra and I’ll hook yours.” Our honeymoon evening and the days and years that followed were sensuously satisfying. There were no complaints.

A couple of years later we bought a comfortable 3 bedroom, 2 bath house in the San Gabriel Valley of Southern California. We literally made it our love nest. Except for my military experience we never left it for long. We never had children so we never out grew it. The years went by too quickly.

Post military, we move

My military stint found me stationed in Texas. After my discharge Emma and I moved back to California. I let my hair grow to shoulder length. It fit well with the hippy era of the time. During a 4 - 5 year period I became proficient at curling and setting my own hair. Emma’s ‘hot curlers’ were quick and efficient. She took photos of me with my long ‘hippie hair’ styled hair in rollers and curlers. We enjoyed experimenting with skinny curlers, large curlers and curler placement; it all makes a difference. Tight curlers were my joy. I learned how to effectively rat my hair and I enjoyed the femme effects I could get by teasing my hair. Unscented Aquanette hair spray became my best friend.

Cross Dressing: I’ve already covered the youthful Joanie

In my adult life, with Emma’s approval, I've worn stockings, panties, lingerie and bras under my work clothes. I discovered that wearing a t-shirt, in addition to a shirt & tie, hides your camisole and bra straps. No one ever called me on it. Wearing an A cup bra feels great and doesn’t draw attention; it hugs your body and doesn’t create an odd bulge. At home I wore a B cup. As I aged I found a B cup bra, used with a bra extender, did a fine job and discretely supported my man boobs well. Emma took it in stride. “Be cautious” is all she asked. And, in respect to Emma, I always was.

I appreciate painted nails, smooth legs, stockings, tap pants and ankle bracelets. Pierced ears were, in my mind, one of my most daring exploits. I had both ears pierced in my early 20s. They significantly added to my feeling of femininity. I like the feel, weight & sway of earrings and I like the taste and smell of MY lipstick. My pierced ears and love of lingerie made for easy Valentine, Christmas and birthday gifts.

In terms of having smooth legs I have used Nair, Veet and razors. Arm pits are a razor thing. All things considered I feel that shaving legs is quicker, easier, more convenient and less messy/stinky than a depilatory. On our cruise Emma arranged to have our legs and under arms waxed. As mentioned I found out that if you wear two layers of stockings that any leg hair or stubble is not noticeable. I shared this trick to a female friend while dressed in femme at a Halloween party. She complimented me on my eye makeup, nails and dress and then asked how my legs appeared be so smooth. (I think she really wanted me to admit to having shaved my legs.)

In fact I have worn pantyhose and knee highs while snow skiing. They function as a very thin ski sock which helps with my ski boots. They also provide added warmth just like thermal underwear. I initially got questions about this from my ski buddies. I was never in a hurry to remove them after a hard day of skiing. I also liked to see and feel them as we relaxed back at our lodge après ski. I always remove my toenail polish before skiing rather than risk an awkward round of questions by the ski patrol or ER staff if I was to have an on-slope accident.

Because my Emma and I didn't have a blue nail polish I picked one up. We share. For St. Patrick’s Day Emma bought us a nice Kelly Green polish. I'm lucky that Emma had "tolerated" my feminine side over the years. Actually she fully embraced it. The Trans’ Caribbean Cruise was a testament to her long time acceptance. In return I kept my girly side discrete... even in liberal California. Except for that brief period in my pre-teens I'm hetro (if that matters) and have always been true to Emma. I was never looking for a relationship with anyone but Emma. One morning we woke up and found that suddenly we were ‘seniors’. We truthfully never saw it coming. No one needs 'drama' in their lives, especially in their so called ‘Golden Years’.

Back to the ‘Trans’ Caribbean Cruise photo album

Taking a break from sorting her closet Joanie had brought a photo album back to her writing desk for a proper viewing. Each picture was special. Their cruise photos made extra special memories come flooding back. Some pictures were nostalgic, some were tear producing and some, mainly from the Fantasy Foto session, were pleasantly erotic.

Savoring the final page of the album Joanie paused and thought ‘I can trace when my cross dressing began, I can trace Joanie’s evolution and I know Joanie will never leave me but I still don’t know why. I guess I just got lucky.’

Dabbing the running mascara from below her eyes Joanie leaned back in her chair, let out a deep sigh, and slowly stood up. Leaving the well worn album on her desk she returned to the closet to finish what needed to be done.

Joanie quickly bagged up Emma’s and her remaining belongings and set them outside the closet. Making final decisions Joanie quickly filled waiting bags with the clothes she no longer needed or wanted, keeping a modest amount that would last her the rest of her life.

Setting her last bag next to Emma’s discards Joanie took a deep breath and stared into an almost empty closet. Standing in the closet doorway she paused; Joanie said a prayer.

“Thank you, dear Lord, for an amazing life and an amazing wife. I have been blessed beyond my wildest dreams. Please bless my Joanie and tell her I’ll see her soon. And, if Michelle is with you, tell her I said hello. Amen.”

Joanie flipped the closet light switch off and closed the door.

The End?

PS - To Michelle: I hope you find this story. Meeting you changed my life. Thank you.

--- Photo is from the 1960s -----

Click-bait is a web page link designed to entice users to go to a certain web-page or video. Click-bait headlines typically aim to exploit the "curiosity gap", providing just enough information to make readers curious, but not enough to satisfy their curiosity without clicking through to the linked content. – per Wikipedia.

The Setup

Jack was an unmarried recent college graduate with a degree in corporate finance and a minor in Social Media. He was in his first year with a Big Ten accounting firm and was working towards an MBA. His future looked bright. He was active with social media postings, tweets and blogging. He had accounts with Facebook, Pinterest, Twitter, LinkedIn, Instagram, Google +, and several other web based outlets; he was a frequent participant. He also was an extremely proficient, but discreet, cross-dresser.

Jack first became aware of his feminine side at age ten. More than twelve years later he had a complete ‘Jackie’ wardrobe and indulged himself as often as possible. He was adept at makeup with emphasis on the eyes. He had his ears pierced at age 13. His makeup collection was complete. Being single he never slept in pajamas; always a baby doll or chemise. His robe was a silk kimono; his slippers were fur trimmed mules with a two inch heel. His natural hair color was brunette. ‘Jackie’ was his chosen femme name.

In the privacy of his condo he routinely web-surfed cross-dressing web sites and had his favorite sites book marked. Some sites were stories, one was for social conversations, advice, and idea exchange relating to the CD/TG community, and another was videos and photos of cross-dressers. Some of his bookmarked sites were porn.

Jack had recently become enthralled with male-to-female photo morphing sites. He liked the fact that he could try a variety of makeup, hair styles and looks and not having to go to the trouble of makeup application, removal, reapplying, etc.; it was all virtual. Just upload a good selfie head shot and play around with no hassle; find a look, hair color or style he liked and then click and save. He had a special computer file labeled ‘Jackie’ where he saved and stored his better looks. His digital photo ‘saves’ didn’t totally disguise Jack. You would think it was Jack’s beautiful twin sister but there was no mistaking or hiding the innate ‘Jack qualities’. He made a very pretty woman.

Trans Form You

Trying to find a better male to female morphing site he stumbled into TransFormU.com that would, in addition to hair and makeup head shots, give you the option of selecting body shapes, breast size, and cleavage options. It also had a clothing, jewelry, shoes and lingerie feature where you could try these items on your virtual body. A finished effort through, TransFormU, would have your perfectly made up, feminine face, on a beautiful woman’s body, dressed or undressed to your specifications. TransFormU.com was perfect in many ways.

Jack was enthralled with making Jackie look and dress beautiful and therefore he was enthralled with the TransformU website. The site offered many options not found on any website that Jack had ever found. Once you had your basic image selected and ‘saved’ you could simply click on what look, image or profession you wanted to look like. With a single mouse click you could be dressed to look like a cheerleader, bride, rock star, a domination mistress, school girl, a nursing mother, etc. There were anime, adult baby, sissy, and biker bitch options. There even was a ‘slut-me-up’ button.

Another unique feature was that once you had the look you wanted you could have your femme photo placed with a background that matched your outfit. The selections were amazingly real world in appearance; if you were in a swim suit you could be shown on a beach, in a wedding dress you could be in a church, as a cheerleader you could be on a football field, as a biker bitch in a bar… just click and choose. The effects were endless and all were fantastically real looking.

Jack had visited the TransFormU site twice, trying to become familiar with how to use the many features. It was on his third visit when he found the site had added a new, adult, feature. It was a beta feature. Once you had selected your complete ‘look’ you would click on the ‘slut-me-up’ options and, for a small $50 fee, the site would put you, in your chosen image, into a two minute computer-generated imagery porn movie! $200 got you five vignettes. A finished movie looked exactly like the real thing. A person could experience, virtually, the desires, impulses and sex acts that they may have thought about, or even dreamed about, but which they would never actually do or act upon.
‘Be the slut you yearn to be’ without the fear of STDs, societal scorn or family drama.

A practical aspect of TransFormU.com was the ability for you to work on several projects concurrently, save them all on the site, and add new features to them until they were complete before saving and downloading them all at once. Among the still photos Jack had already saved was Jackie as a long haired blond with a 40D breast, impressive cleavage, nude, wearing high heels and made up like a runway model. He added scarlet lipstick and finger nails for the effect he liked.

Saving and building on this basic virtual image Jack clicked on ‘lingerie mode’ placing Jackie in matching red garter belt and panty set, black stockings, a black and red pushup bustier (with lace trim) that emphasized cleavage. Jack added black four inch pump heels, sexy gold chandelier earrings, show girl makeup and long brunette hair. For a background he had Jackie standing, with her hands on her hips, at the foot of a magnificent bed in a beautiful boudoir setting.

Jack also refined the classic cross-dressers fantasy of wearing a wedding dress. For a background he opted for a soothing mountain meadow setting. Jackie made a beautiful bride. Finding a ‘waif’ option Jack added this look giving Jackie a more provocative, pouty, look. Just one click of his mouse made it happen.

Another effort for Jackie was the bikini swim suit option. He swapped her into a red hair pixie cut hair style, increased the feminine arch of her eyebrows and opted for a skimpy pushup top that gave Jackie an outstanding cleavage. The string bikini bottom was barely there and was erotic for him to look at. He selected a Laguna Beach setting to complete this fantasy. Jackie looked hot!

The final scenario Jack created was that of the perfect Sissy. Black patent leather Mary Jane shoes and white leggings were easily added. His Sissy dress had a large bow in the back. And of course his face was perfectly made-up. Let your imagination complete your mental image of what this entailed.

Developing each image took a pleasant toll on Jack and his arousal increased the more he explored what he could do with Jackie and TransFormU. He had all his virtual creations ‘saved’ and ready for download to his laptop. Yet there was one additional feature of TranForm he wanted to use; the ‘Slut-Me-Up’ option. Before attempting this he wanted to switch to Jackie mode; it would fit with what he was about to do.

A repressed and tightly controlled fantasy for Jack was having a sexual relationship with a man. It was a fantasy that he doubted he would ever act on. He was, he thought, very much in control of his desires, impulses and fantasies. What would it be like to be on the receiving end of a steamy, same sex, relationship while in full Jackie mode? There were tastes, sensations, and lusty feelings he secretly yearned for. He was curious.

Before trying the beta ‘Slut-Me-Up’ feature Jack went to his kitchen and mixed himself a Tito’s vodka and Sprite. Taking his drink to his bedroom he swapped from his male clothes to Jackie clothes. This didn’t take long as he had been wearing lingerie under his pants and shirt all day at work as he usually did. He slipped breast forms into his bra, pulled on a pair of lacy peach shorty pettipants (for tactile reasons), donned a cute, flowered, romper and inserted 2 inch gold hoop earrings into his waiting ears. He already had his garter belt and cinnamon stockings on which made slipping into his black ballet style shoes easy; they were well broke in.

Jack went to his vanity, sat down and applied some facial make-up, eyeliner, a bit of eye shadow and mascara. His hair was long enough that he could easily backcomb it a bit and shape a believable pixie hairstyle. A blast of hairspray maintained his femininity. Finding his favorite shade of lipstick he expertly enhanced his lips. He gave himself a spritz of perfume and was ready to try the ‘Slut-Me-Up’ option on TransFormU. He wanted to be a bit naughty when he made virtual Jackie naughty.

The growing bulge in her French cut panties urged Jackie to lie down on the bed to relive her building lust. Jackie had a pressing date with TransFormU and didn’t want to take the time so she folded some tissues and placed them in her panties to soak up the pre-seminal oozing. Grabbing her purse, that held her credit card, Jackie went back to her lounging chair and her laptop.

Sitting back in her chair Jackie took another swig of her drink, retrieved her credit card, logged into TransFormU and prepared to get slutty. She was weighing which version of virtual Jackie to make “slutty”. ‘Lingerie Jackie’ or ‘Bride Jackie’? They both seemed like exciting and very worthwhile options.

Jackie carefully entered her credit card number, and when prompted, selected Lingerie Jackie. She had a couple more criteria to click on. For ‘select a place’ (for her movie to take place in) she chose the ‘bedroom’ option, and for the ‘with who’ drop down menu she clicked on ‘two men’, making a promise to herself to next time try the ‘man + woman’ scenario. Her final choice was ‘voluntary or rape’? Jackie wanted to be a willing participant in whatever would be depicted. She smiled as she thought about how the final product would play out.

Before clicking on the ‘Slut-Me-Up’ icon Jackie modified her ‘self’ by switching to long platinum blond hair, added bangs and ultra sexy, vixen looking, eyebrows; it completed the look she was trying for. Taking another sip of her drink Jackie took a deep breath, exhaled, and clicked on the ‘Slut-Me-Up’ icon. A notice appeared on the screen indicating that the process could take 10 to 15 minutes to complete. She leaned back in her chair, closed her eyes, tried to relax and waited.

Her mind was racing even though her eyes were closed. There were so many ways that she could be slutty! As she considered the possibilities her penis began growing and throbbing in anticipation. With eyes still closed she rolled up the leg of her jumper and was able to feel and stroke the bulge in her panties. She hooked her right thumb onto the elastic band at the top of her panties and pulled them slightly down. Using her right index finger she pushed aside the tissues she had placed there earlier.

Jackie began a slow circling of her cockhead, making an effort to spread her natural lubricant around and around the tip. Using the same finger she spread her slippery pre-seminal fluid down and around the corona of her penis. The mental images she was envisioning, as she waited, combined with the copious amount of pre-cum she was producing, were overwhelming and would soon need to be dealt with. Before she could take matters into her own hand her laptop beeped her back to the present. “Done” was the one word message overlaid onto the TransFormU opening screen.

Jackie licked her wet fingers out of reflex and pulled her panties and romper back into place and leaned forward to pick up her mouse. She clicked the ‘preview’ icon and leaned back again.

The Preview

The two minute, $50 mini-porn movie was just that; very graphic, very erotic and very XXX rated. It was well worth what Jackie had paid. Watching the preview, prior to downloading, was like living the experience without actually having to get down on your knees in front of your lover. Jackie watched herself pull a man’s penis from his boxer shorts, kiss the head and suck and swirl him with the timing of a pro. The moment of her ‘boy friends’ ejaculation was graphically captured; dribbles of cum were seen running down her chin as she tried to swallow. Her rigid penis was clearly visible.

The second man she had requested showed up half way through her two minute performance. Jackie could be seen eagerly bringing ‘man 2’ to a firm erection with her mouth, returning to her in-progress blowjob on ‘man 1’ while guiding ‘man2’s’ penis to her rectum and pulling the first two inches of ‘man 2’into her rectum. Very slutty! The close-ups were amazing in their detail.

Jackie had clearly been ‘slutted-up’! ‘Man 2’ could be seen giving Jackie a reach around as he plowed her ass. One of the more graphic scenes has Jackie with her legs over the shoulders of ‘man 2’ while being slow fucked, bare back, by him… she was clearly enjoying it. Another scene had her up ‘man 1’s’ ass all the way up to the base of her shaft. And then the mini-movie was over. Computer-generated imagery (CGI) has cum a long way.

Jackie found herself extremely aroused by watching her ‘movie’ and was panting like a dog in heat. The movie was all she had hoped for. It definitely was for personal viewing only. It was NOT ‘work place safe’.

Jackie adjusted her panties and romper to one side, gaining access to her throbbing penis. She picked up a box of tissues from a side table and hit the replay button. Before her personal porn video had played through to the end she had found extreme, and messy, release and self gratification. She was going to have to wash her romper. It was a memorable and joyful orgasm!

Having cleaned up and composed herself Jackie leaned over to ‘save’ her movie and four still images (bride, sissy, lingerie, and biker bitch) that she had just ‘previewed’. She clicked on the download icon. While they were downloading Jackie picked up her soiled tissues and went to change into a clean outfit. She tossed the tissues in the trash and decided to get more comfortable. After all it was a Friday evening and she had no place to go until work on Monday.

She got nude and selected tap pant underwear, a sleep bra and her silk lounging kimono. It felt good to be free of her normal bra, stockings and suspender belt. She lightly scratched her belly and breasts, walked to her vanity and changed to a lighter shade of lipstick. Smacking her lips to evenly spread her lipstick she looked in the mirror and said out loud, “Jackie, you’re such a very naughty girl. A virtual slut! And I have the video to prove it!” She blew a kiss to herself, winked, laughed and went to make herself another drink. Jackie liked her Tito’s.

She squeezed a lime into her vodka and waited for her downloads to finish. Jackie turned on some soft background music and sat back into her chair. She checked and made sure her new creations were properly in the ‘Jackie’ file on her laptop. They were. She sipped at her drink and decided to go through some emails.

The first email she read was unsettling. It was from Bob in the mail room at work. It read:

“Dearest Jackie, Thank you for trusting me to the degree that you would share your ‘special’ photos and video with me. I feel honored. Your secret is safe with me. I too have a feminine side but am too insecure to let it out. Your garter belt in your video is so yummy-sexy! And what you did to that man was very hot. If you would like to try someone new please give me a call. I’ve attached, in confidence, a picture of me in my favorite dress. Best wishes and hugs! “Diane” XOXO

Jackie’s jaw dropped. Her brain struggled to comprehend how “Diane” knew about Jackie and her movie. She refocused her eyes and read the next email:

“Miss Jackie, You are so incredibly hot! Seeing you at work I never would have expected that you could fem up so well. I had noticed that you had pierced ears but never guessed your secret. I’d like to take you on a dinner date to the Sycamore Inn sometime. I’ll leave a tube of L’oreal lipstick, with my phone number, on your desk Monday. I think the shade will look perfect on you! We have the same skin tone and it looks great on me. Call me. Yours truly, Jonny”

Jackie’s heart was pounding and her hand was shaking. How could this be happening? The numbers of unread emails were stacking up. Jackie logged back into TransFormU and immediately went to the settings area. Quickly going to the download setting Jackie gasped and slumped back into her chair. The problem was glaringly obvious; a real bone-head, amateur, mistake.

Still slumped into her chair Jackie took a large gulp of her drink and sat staring at the screen of her laptop. In the ‘download’ settings she had quickly selected ‘save’ and had left the ‘setup’ area. Looking at what she had done she saw that she had clicked on ‘save & share’! She had only wanted to ‘save’ her projects. In error she had ‘shared’ her movie and images with her entire ‘friends’ portion of her email address book. “Oh, my God… what have I done?” Life was about to get very complicated.

It could have been worse. The ‘share with’ options that were not checked included Facebook, Pinterest and several other options. In that regards Jackie was fortunate. The other piece of good news was that her email ‘friends’ has only forty entries. Some of her ‘friends’ were coworkers. This explained why Bob and Jonny had commented on her ‘movie’, so far. Thankfully the email addresses for ‘family’ and ‘work’ had been spared.

It was 9 PM Friday night and her movie had already set off a flood of emails. Some were not very nice. She only had two days to fabricate a believable explanation before reporting for work on Monday. That also meant that there were two days for more emails to roll in. “Oh, my God.”

Awakening Saturday morning Jackie lay in her bed, clad in her feminine sleep attire. She slowly stretched as she began to wake up. It had been a deep, relaxing sleep and she was enjoying the solitude and comfort of a lazy morning. And then the debacle of the night before hit home.

Jackie bolted upright in her bed and her mind began racing. “What the hell am I going to do!” she blurted out. She swung her feet over the bed, slipped into her fur trimmed mules, glanced into a mirror and fluffed her hair and went to the kitchen for coffee. She flipped the switch on the coffee maker. Glancing at her laptop she was glad that it was closed. ‘I’ll deal with that later’ she thought. Picking up her cell phone she saw that she had four messages. Setting the phone down Jackie snuck a cup of fresh coffee while the coffee pot was still brewing.

Adding a splash of milk and two teaspoons of sugar she pulled out a kitchen chair and sat down to think. ‘What the hell am I going to do?!’ she thought.

Finishing her second cup of coffee Jackie decided to shower before doing anything. Her cell phone rang and she let it go to message as she adjusted the water temperature in her shower. Whoever it was would just have to wait. Hopefully it was not her job telling her to not bother coming to work Monday. There were a few more coworkers in her email ‘friends’ that she had not heard from… yet.

The warm shower felt great and help to clear her head. Grabbing her razor and shaving foam she made quick work of making her legs nice and smooth. She shampooed and conditioned her hair, turned off the water and stepped out of the stall. She toweled her hair and patted her legs almost dry. She applied some coconut oil moisturizer to her legs and set some skinny curlers in her hair while it dried. Jackie liked the body and waves the curlers gave her.

Because it was a Saturday she pulled on a pair of French cut panties and a pair of low cut white shorts with a three inch inseam. The rolled cuffs made her shorts cuter as did the embroidered humming bird on a rear pocket. Opting for a teal colored push up demi-bra she inserted her breast forms and selected a yellow blouse that had a small white flower pattern. She buttoned a couple buttons and then knotted the shirt tails into ‘island style’. Opting for minimum makeup she chose a coral lipstick, blush on her cheek bones, and her usual black mascara.

Switching from the gold hoop earrings she inserted some cute pearl studs in her ear lobes, added several bangle bracelets and two rings. A few well placed dabs of perfume on her wrists and throat and she was ready to face the day. Slipping into a pair of leopard print flat sandals Jackie went to the living room. Looking down at her feet Jackie smiled and was glad she had recently painted her toenails a dark blue. The silver toe ring completed her. She opted to not wear her anklet. The curlers would remain in place until her hair dried.

Jackie made herself a toasted English muffin, with peanut butter and honey, and went to her laptop. She flipped open the laptop and turned it on. Her new emails were waiting.

“You disgusting pervert! How dare you send me those disgusting photos? I will have the police on you if do it again. Get some professional help.”

“I found your unsolicited images were very interesting but totally inappropriate for email. If you’d like to share your photos let me know and we can share them at my house. (You make a stunning blond.)”

“Damn, you are one hot mama! Why did you send them to ME? I’m in a relationship at present but if that changes I’ll let you know.”
“Whew”, Jackie thought, “the response isn’t as brutal as I thought it would be. Maybe there’s a way to fabricate a plausible explanation, keep my friends and my job.”

Taking a final bite of her muffin Jackie drank the last of her coffee. She reached up and felt her hair. ‘Almost dry’ she thought.

Jackie walked to her vanity, carefully removing her curlers as she walked. Using her separated fingers she slowly combed her hair upwards one time. Grabbing a can of unscented hair spray she bent at the waist, and let her hair hang down. She gave her hair a liberal spray and waited 20 seconds for the spray to firm up. Standing up she shook her head left and right a few times and checked her image in the mirror. Her hair was almost perfect. Using a brush she quickly had it the way she liked it. A final spray and she was done; a cute pixie cut in less than a minute. As long as she was at the mirror she reapplied a new fresh coat of lipstick.

Returning to the task of reading the email responses to his accidental emailing his en femme images and porn video Jackie began clicking through them.

A few replies were very negative, a few were accepting of Jackie’s hobby and a few wanted Jackie to ‘make’ them paint their nails and dress as women. And then there were some that wanted to have sex. “So far, so good” Jackie thought. And then she opened the next email.

“Jack – A copy of your video and photos were forwarded to me. They, and therefore you, reflect negatively on the corporation. Before I forward your video to HR I want to speak to you. I will call you at 12 noon Saturday. If you do not answer do not bother coming to work on Monday. If you decide to answer perhaps we can arrive at a solution.” – Mike Spence, CEO

‘Oh, my God… what have I done? What the hell am I going to do?!’ Jackie thought.

Precisely at 12 noon Jackie’s cell phone rang. On the second ring Jackie answered and stood up.

“Hello, this is Jack.”

“This is Mike Spence. Put Jackie on the phone.”

Taken aback by the request and the stern voice Jackie replied (in the same voice), “This is Jackie.”

Mr. Spence began: “Have I made it clear about how you and your video are an embarrassment to the corporation? Are you aware that your career and future are hanging by a thread… a very thin thread? And that I hold that thread.”

Jackie’s heart was pounding and her palms were getting damp. “Yes, I understand” she replied.

“Good.” Mr. Spence said in a terse tone. “We both understand your situation. Before we speak further, answer my questions. It’s obvious that you enjoy your female side. Why?”

“When I’m Jackie I feel very special. I love the taste of lipstick and the feel of nylons and lace. I find lingerie so much nicer than boring men’s clothes… you know, the usual.”

“Do you like your job? Do you want to keep your job?”

“Yes sir, I like the company and I like my job. I hope to advance to a more responsible position.”

“How far have you taken your cross-dressing? Do you shave your legs? Have you had sex with men? Your video says that you have.”

“Yes, I have shaved my legs for many years but I do no harm to the company by doing so. That video was all done with computer software. It’s not me. I’ve fantasized about sex with men before and that’s why I made the video. By mistake my images and video were accidentally sent to several people. I apologize.”

In a softer tone Mr. Spence replied with “Hmmm. Maybe there’s hope for you and we can reach a mutually beneficial arrangement. Of those photos which one do you like the most?”

Surprised at the change of tone of the conversation Jackie did not hesitate and replied, “I like my ‘lingerie mode’ first and then it’s a tie between the wedding dress and Sissy mode.”

Equally quick in his response Mr. Spence said, “I really like the ‘lingerie mode’ but I find the Sissy option is… shall we say, pleasant to consider. Your nude version is also pretty nice.”

The phone went silent. Jackie dared not say anything. She thought she could hear barely audible heavy breathing.

Mr. Spence broke the silence with “I have a proposal that could be beneficial to us both. I’ve already arranged for two days of sensitivity training at the office. You are off work, with pay, until Wednesday. You won’t have any problems at work from then on. The rest of my offer, and your career, depend upon you and your complete secrecy. I’ll have a non-disclosure agreement prepared and you will sign it.”

There was a pause and Jackie could hear ice cubes tinkle as Mr. Spence took a sip. Spence continued.

“I’ve viewed your video several times and it has awakened some very real needs and desires that I must deal with. I also like wearing lingerie and feeling slutty. It makes me feel very alive and… and very horny. To put it bluntly, I find you very attractive and I want to have sex with you. Not just once. I’m looking for a longer commitment. A one year agreement to begin with, subject to extension after six months. You would be well compensated and I’d guess that a person with your, shall we say, special ‘talents’ would need a better assignment and an office… there would be special projects that might take us out of town periodically. I have a mountain home that’s very secluded.”

Jackie was sitting in her chair, saying nothing and taking this all in. It seemed so surreal. She sensed a shift from being on the defense to being the dominant negotiator. She had something that Mike wanted very badly. He had tipped his hand. Lust can do that to a person.
“Are you there Jackie? Do you understand what I’m suggesting? It’s a win-win situation. What are your thoughts on my proposal?” There seemed to be a plaintive tone to Mike’s voice that bordered on desperation.

Hesitating a moment for effect Jackie softly replied, “It does seem like a mutually beneficial arrangement, doesn’t it?” As the proposal sank in Jackie could feel the start of an arousal. Having sex with a man AND being paid. Would that make her a whore? It didn’t really matter. It seemed like a wet dream come true.

“So what do you think, Jackie? Monday is the day after tomorrow. You’re running out of time and options. Your emails stirred up a lot of problems that the company doesn’t need. Say ‘yes’ and I’ll come to your condo tomorrow at noon. We could, if you will pardon the pun, consummate our agreement. I want you to be in the outfit I see in your lingerie photo. Is it a deal?”

Jackie smiled as she realized that she was in a position of power. She pulled the zipper down on her shorts. Holding the phone in her left hand she slowly began running her finger up and down her hardening cock. “Mr. Spence, you know I’m really a brunette, right? And in my video I’m a platinum blond, right?”

“Well, I’ll bring you a long, blond wig. Please, call me Mike.”

Jackie replied “Platinum blond, human hair, Mike.”

Dropping her voice and trying to sound sultry, Jackie added “You know Mike, sometimes I like having black hair; Sapphire black, shoulder length.”

Mike responded with “Ok, I’ll bring you two wigs and a bottle of Tito’s. Is that ok? Is there anything else?”

“Yes, there are just few things more. Don’t wear underwear, bring your favorite panties, and bring your nylons and a box of sheepskin condoms. I think you’ll like they way I feel when I’m deep inside you.”

Jackie was sure she heard a gasp from Mike who was breathing heavy like a man in lust. Continuing Jackie said, “I’m sure I have a bra that will fit you. I hope you like lace, Mike. I do.”

“I’ll see you tomorrow. By the way, I’m a 38 B.” Mike hung up.

Jackie put down her phone and giggled at the turn of events. Her future was looking brighter.

Finis?

Note to readers:

It’s the age old conundrum. There’s probably enough story left for a second chapter. But should there be another installment? I’m curious as how Bob (aka ‘Diane’), in the mail room, will interact with Jackie and I’m wondering if co-worker Jonny will actually leave Jackie the tube of lipstick he promised to leave on Jackie’s desk. Will there be other gifts left? How will the accidentally sent photos and video be resolved? And, of course, how will the arrangement between Mike and Jackie go? Will there be a trip to the mountains? A business trip to Miami or…?

"Writers must recognize the stop signs in their… stories."

Previously

“Yes, there are just few things more. Don’t wear underwear, bring your favorite panties, and bring your nylons and a box of sheepskin condoms. I think you’ll like they way I feel when I’m deep inside you.”

Jackie was sure she heard a gasp from Mike who was breathing heavy like a man in lust. Continuing, Jackie said, “I’m sure I have a bra that will fit you. I hope you like lace, Mike. I do.”

“I’ll see you tomorrow. By the way, I’m a 38 B.” Mike hung up.

Jackie put down her phone and giggled at the turn of events. Her future was looking brighter.

Things are looking better

Having gotten herself into a very dire situation when extremely compromising photos and a mini porn video were accidentally sent to the contacts in her email address book Jackie had gotten extremely luck. Not only was she not going to lose her job (and possibly many friends) Jackie was being promoted and would be involved with special projects.

The scary downside was, that for this to happen, she was going to have to fuck her boss, Mike Spence! Having viewed Jackie’s porn movie, even though it was CGI rendered, Mike was infatuated with Jackie. What added to Mike’s obsession was that he was a closeted cross-dresser that literally ached to express his feminine yearnings and for man-on-man sex.

It was a little after 1 PM on a Saturday. Jackie was feeling the need to be at her very feminine best for her boss tomorrow afternoon. Her future and career depended on it. What could she do between now and 12 noon tomorrow to look as femme as possible for Mike? A quick self assessment narrowed her options to hair, eyebrows or fingernails.

As a bonus Jackie’s “date” would be fulfilling her own latent desire to experience sex with a man. Unknown to Mike it would also be Jackie’s first foray down that forbidden trail. There were lots to be done and a short time to get it done.

And there was the nagging ‘problem’ with her sex tape and photos. She needed a way to explain them away. The photos of her in various sexy roles were the least of her worries. She could pass the photos off as a lost bet, a dare, a prank… but how to explain the porn?

Taking time to collect herself, and her thoughts, Jackie made herself a drink and went to her chair. She didn’t want to do anything brash. ‘Hair, brows or nails’? she thought. ‘I need to look more femme soon.’ Her laptop alerted her to a new email. Leaning forward she clicked it open. It was from TansFormU!

“Dear valued TransFormU beta user. You recently downloaded an end product of a TFU feature that continues to be refined. Our records show that yesterday you downloaded several still images and our ground breaking ‘Slut Me Up’ video. We omitted an important program security key which you MUST enter on the computer that was used for the download if you want to keep your items from expiring and auto deleting. Enter this security key BEFORE 6 PM PST today or you will lose ALL your creations: A147JX-G98PZ2-62KK33. We apologize for any inconvenience this oversight may have caused you. We appreciate your patronage.”

Jackie let out a loud ‘whoop!’ of excitement. A good day and a bright future just got better and brighter! She took a long sip of her drink and leaned back in her chair, laughing loudly. She re-read the email and giggled over her good fortune. ‘My “Slut Me Up” porn video and photos will automatically delete from everybody’s computer but mine! Mike doesn’t know! Nobody knows but me! They have no proof!’ Glancing at a clock she had about four hours to save her creations. She hurriedly typed in the security code to preserve her items, leaned back in her chair, and smiled like the Cheshire cat after eating a canary.

It was an amazing case of dodging a bullet, getting a second chance or whatever metaphor you wanted to use. Jackie said a silent prayer of thanks.

Jackie sipped and thought. ‘Should I cancel my date with Mike? No, I need him to conduct the sensitivity training at work or else I better never show my face there again. I need Mike in order to further my career and get a pay raise. And I need Mike because… I want a man.’
Taking another sip her pondering continued. ‘I need Mike. I need to keep Mike. I need to make Mike want me. I need to make him want to keep me. But how? I need to satisfy his desires. But how? What are his desires? He desires me to look like my porn video. But how? He desires to be femmed up (I can do that) and he desires to have sex with me (I CAN do that!)’ All was not lost.

Getting ready

‘I need to look more femme as soon as possible. Hair, brows and nails should do it’ she thought. Using the search engine on her laptop Jackie called House of Beauty Salon a block away. She explained that she wanted acrylic nails and eyebrow shaping. They had an opening and said it would take a little more than an hour and would cost $50 to $75 depending on what they did. They would be open until 6 PM. Jackie made the appointment for 3 PM. Figuring that she was off work until Wednesday that would give her Sunday, Monday and Tuesday to enjoy these feminine niceties in case she had to ‘butch it up’ with a more manly look on Wednesday. And perhaps Mike would have a solution.

Changing into a pair of mid rise denim pants and a simple print blouse Jackie applied some lipstick, grabbed her purse and left. Two hours Jackie was home and definitely looking… pretty. The beautician, upon learning that it was Jackie’s first salon visit, spent more time and effort with her. Asking if Jackie was trying for a certain vibe or look Jackie had replied, ‘Sexy, verging on slutty’.

Her acrylic fingernails were perfectly shaped and almost ¾ inches longer; definitely more girly looking than before. They were a dark scarlet as were her toenails. Her eyebrows had the super feminine thin arch seen in her ‘Slut-Me-Up’ video. As a special service to Jackie the beautician tinted Jackie’s eyelashes and eyebrows that wouldn’t fade for six weeks. There could be no going back. ‘I hope this gives Mike the hard-on that he’s looking for’ she thought.

Before returning home Jackie bought matching pairs of Silky Sheer Cocoa colored pantyhose; one for Mike and one for her, a tube of KY Jelly personal lubricant, a box of Kotex Ultra Thin Pads with wings, two deli sandwiches, and two liters of Sprite for her Tito’s.

Entering her condo she put her shopping bag down and quickly walked to her vanity mirror. She placed the Kotex Ultra Thin Pads on her vanity. Jackie sat down so she could admire her new look. She held her new dark red fingernails next to her face to confirm how they, combined with her newly tinted and shaped eyebrows and long, dark lashes, gave her the look she was striving for. ‘Damn, I’m hot!’ She used a tissue to remove her daytime lipstick and replaced it with a dark red color that closely matched her nails. Picking up her eyelash curler she gave them a nice crimping.

She had to get away from the mirror as she was infatuated with her look. Her jeans were beginning to bulge. Grabbing her cell phone she clicked off five or six selfies, making a mental note to update her TransFormU images in the near future.

Going back to the kitchen, she put the deli sandwiches and Sprite in the refrigerator and brought Mike’s new pantyhose and a pair of scissors to her usual chair. Sitting down she opened the packages and carefully cut access holes for Mike’s cock and his sphincter. ‘Best to be prepared’ she figured. She wasn’t sure how tomorrow would play out.

The evening was fading and she wanted to be bright eyed and eager for Mike. Her fate, literally, was in his hands. It was going to be an interesting day. She straightened the house a bit and retired to bed. She didn’t wear her favorite chemise thinking that she would save it for tomorrow. She removed her lipstick and climbed into bed. ‘I’ll remake the bed with my satin sheets after breakfast.’ She turned off her night light and tried for sleep.

Jackie’s alarm clock woke her at 8 AM. After coffee and breakfast Jackie spent some time to make sure that the condo and her bedroom looked nice and neat. Mike was due at noon and at 9 AM she began to get ready.

She showered and shaved all the areas that needed it and some areas that didn’t need it. She was not leaving anything up to chance. It had been months since she had shaved her crotch so she had to spend a little extra time to get it just right. ‘Mike better appreciate all this shaving’ she complained. ‘I wonder if he will be smooth. I’d like that.’

Stepping from the shower she dried and moisturized her freshly shaved legs. Once dry she tucked her penis and slipped into black French cut panties before going to work on her shag pixie cut hair style. Hairspray was the final touch. She looked pretty.

Recalling her TFU ‘lingerie mode’ look Jackie dressed in her matching red garter belt and panty set, black stockings, a black and red pushup bustier (with lace trim) that emphasized her cleavage. Her breast inserts helped her look very well endowed. She stepped into black three inch pump heels unlike the four inch heels in her CGI movie. Managing to find some dangling gold chandelier earrings she tried for the show girl/slut makeup that Mike apparently liked. On purpose she didn’t apply any eye shadow.

Sitting in her thinking chair Jackie plotted on how to keep the negotiating power she had asserted during her conversation yesterday with Mike. There were several things that were in her favor. 1- Mike didn’t know that all Jackie’s TCU images had deleted themselves by now. 2 – She had something that Mike wanted… and he had made it clear that he wanted it very much; almost desperately. Jackie made a mental note to not seem weak or desperate. She had to be in control.

With that in mind Jackie removed her earrings, placed them on her vanity, and inserted her pearl studs. Next she wiped her ‘Trollop Red’ lipstick off. There would be time for that later. She wanted Mike to see her looking fairly plain when he first arrived and would then transform to a more sultry look after he arrived. It was all about the image.

Kicking off her heels she pulled on Jack’s khaki business slacks over her garter belt and nylon covered legs and slipped into a pair of Jack’s loafers. Black nylons could be seen where socks should be. Selecting one of Jack’s long sleeved white shirts she put it on, tucked it loosely into the khakis, making sure to leave the shirt cuffs unbuttoned, and the top two buttons open.

Her new scarlet fingernails showed at the end of the sleeves in contrast to the man’s white shirt. Hints of her lace bustier were, on purpose, visible at her neck. In fact her cleavage was visible. She made an erotically androgynous image standing there; a woman dressed in men’s clothes, with obvious breasts and a pixie shag hair style. Her beautifully shaped eyebrows and well defined eyelashes completed the image. The pearl studs were perfect. It was part of a plan that would, hopefully, keep her in control of the situation as well as her future.

Jackie had sensed a definite shift as who was on the offense during yesterdays call with Mike. There was a defining moment that tipped the conversation in her favor. She felt it when Mike said he wanted her… there had been a plaintive tone to Mike’s voice that bordered on desperation. Jackie wanted to maintain that leverage.

Taking care of last minute details Jackie brought an extra chair into her bedroom and placed it next to her vanity. On top of the vanity she staged several tubes of lipstick, bottles of nail polish and mascara. She placed the KY lubricant on a night stand and strategically placed some extra tissue boxes throughout her condo. Mike’s modified pantyhose were conveniently waiting on the foot of her bed.

Retreating back to her thinking chair she closed her eyes and tried to psyche herself up. There would probably be many firsts for her today and she wanted to be as prepared as possible. With her eyes closed she mentally went down a check list. How far would she let him go with her? How far would she go on him? Would he fire her? Jackie did some yoga breathing to help steady herself.

At 11:30 AM she got up and lit scented candles in the kitchen and bedroom. Checking in the mirror she thought, being in Jack’s clothes, that she looked like a not so subtle lesbian. That mental image made her giggle. She resisted the urge to apply some lipstick but did make a few brush strokes of blush to her cheekbones. She placed a solitary dot of perfume behind one ear.

Returning to the kitchen she started a pot of coffee, laid out two coffee cups and two drinking glasses, a bucket of ice and a small plate of lime wedges. She went to the living room, pulled the curtains closed and sat on the sofa to wait.

The boss arrives

Precisely at 12 noon there was a firm knocking on her door. Jackie waited for the second knock before standing and going to the door. At about the time there would have been a third knock Jackie opened the door. Standing outside was a handsome looking man that held a large shopping bag in one arm. “Hello, I’m Mike Spence” he announced.

Jackie opened the door wider and said “Please come in, Mike. Welcome to my home.” Mike looked left and right, which was a ‘tell’ of his nervousness, before stepping in. Jackie closed the door smiling at what she had just seen. ‘This is starting well’ she thought.

Mike walked over to the counter and put his bag down. He did a careful check of the condo before making eye contact. “Your place looks nice” Mike offered. Jackie stepped closer and, in a manly fashion, firmly shook Mike’s hand and said “Thank you for coming, Mike.” While still shaking Mike’s hand Jackie made a quick assessment. Jackie stood about 5’ 7 inches and it appeared Mike was maybe three inches taller. He looked to be about 150 pounds, appeared fit and could best be described as boyishly handsome. According to company literature Mike was 30 years old, unmarried and liked snow skiing. Even by Jackie’s standards Mike was handsome. He had a boyish face, check bones that begged for blush and he had no facial hair. There were remnants, in both ears, of having pierced ears at sometime. ‘He could have been worse’ she thought.

“Would you care for a cup of fresh coffee?” Mike was checking Jackie very closely. “Yes, please. Black, no sugar.” Jackie poured a cup for Mike and one for herself. She stirred in two teaspoons of sugar and a teaspoon of cream into her cup. She walked the cups over to the kitchen table and asked Mike to have a seat. He did.

Sitting in silence for an awkward moment Mike took a sip of his coffee. Jackie kept stirring her cup, not taking her eyes off Mike. Mike took another sip and then said “I told you to be dressed… differently than this. I came to see Jackie.” “Yes Mike you did. But first I’m sure you have business to resolve with Jack, right?” With a free hand Jackie widened the gap of her shirt exposing more of her bustier and cleavage. “Jack will leave once we’re done with the paperwork.” Mike’s pupils became larger. ‘Ah, another tell’. Jackie inwardly smiled and took a sip of her coffee.

“Let’s get the paperwork out of the way first. Don’t you agree?” Mike retrieved a file folder from the bag he had brought in and returned to the table with a pen. “All of the items we discussed yesterday are in this document. The term of the contract is one year with extensions available after six months. I’ve decided that you will be my Special Assistant with duties and projects determined by me. I’ve set your annual salary at $75k with a chance for performance bonuses. In return you will… (he gulped and had to take another sip of coffee to loosen his voice)… you will help and assist me as we discussed yesterday.“ Trying to sound managerial and authoritative he added “Is that clear? There is also a Non Disclosure Agreement that, if you violate it, will make your life a living hell. And there is a Sexual Exclusivity Agreement. Neither of us can have sex with anyone else. It protects us both from STDs.”

Jackie looked demurely over her cup of coffee and softly replied, “Yes, Mike. It’s clear. And will the company conduct the two day LGBTQ sensitivity training?” “Yes, it’s all set to go starting Monday.” Jackie gave Mike a perplexed look and began tapping her pretty red acrylics on the table top. “Mike, don’t you think that it would be best if the company had annual sensitivity re-training?” Jackie asked. Mike looked momentarily startled by Jackie’s boldness. He paused to give her suggestion some thought. “Yes, I think that would be the right thing to do.” Jackie reached over and placed both of her warm hands on Mike’s hand, letting them linger just a bit; she gave them a gentle squeeze and took the pen from Mike’s hand. All documents were quickly signed and Jackie pushed them back to Mike.

“Now that that’s done why don’t we get more comfortable? Would you care for a drink?” she asked. Mike nodded and they both went to the counter where the glasses were. Jackie began filling their glasses with ice and Mike reached into his bag producing the promised bottle of Tito’s vodka. Mike poured the vodka and Sprite while Jackie added the limes. She thought she saw him try to get a whiff of her perfume.
Staring at each other they both raised their glasses. “To a new future” Mike pronounced. Jackie smiled and added “And here’s to new experiences.” They clinked their glasses, took a drink and they both nervously giggled.

It was as if a heavy weight had been taken off them. The hard part, no pun intended, was behind them.

Jack leaves

“I think we are done with Jack. Let’s have seat on my couch for a bit, shall we?” Jackie instructed. With drinks in hand they walked toward the couch. Jackie paused by her thinking chair and kicked out of Jack’s loafers. She put her drink down by her laptop and removed Jack’s pants, hanging them on the back of her chair. The white shirt quickly followed. She was now standing in her ‘lingerie mode’ items. Her nylon covered feet contrasted nicely with the white carpet. Mike was watching and enjoying her transformation. Mike commented, “That outfit is fantastic! I see no maleness. It gives me a goal to strive for… with your help. It also makes me… envious.” Jackie was sure that he was going to say ‘horny’.

Jackie picked up her drink, faced Mike, struck a not so subtle slutty-girl pose and then joined Mike on the couch. They sat a half cushion away from each other. She took a sip and placed her drink on the coffee table. Jackie crossed her legs and moved next to Mike; the sound of her nylon covered legs crossing did not go unnoticed by Mike. He took a gulp of his drink and stared some more. Jackie could sense that his mind was whirling. “So, what do you think Mike? See anything you like?”

Mike gulped and tentatively put his hand on Jackie’s nylon covered knee and slowly rubbed it. “You look, and feel, stunning; much prettier than your video.” “Thank you Mike, a girl likes to hear that. I think that, with a little effort that you could look pretty too. You have a face and cheek bones that would lend themselves to being pretty.” Mike blushed and took another sip of his drink. “I would like that” he confessed.
Jackie reached over and laid her hand on Mike’s knee and suggested, “Make yourself comfortable. Kick off your shoes.” Mike quickly did. With his shoes off Jackie saw that Mike was wearing black nylons with a reinforced toe. ‘He’s got a head start it seems. I bet they are thigh high style’ she thought. Rather than ignore the elephant in the room Jackie pointed at Mike’s nylon covered toes and said “It seems we both like black stockings, Mike. I wonder what other items we share a love for. Do you like panties and lipstick, Mike?” Mike didn’t answer and his eyes diverted away from Jackie. He licked his lips. ‘Another tell’ thought Jackie. They both took a sip of their drinks and leaned back into the couch. A strong level of tenseness had vanished. ‘So far so good’ Jackie thought.

Jackie thought about moving Mike’s hand to the inside of her thigh but quickly shrugged that off. ‘Can’t be to bold… just enough to keep things in my favor. “What did you bring in the bag Mike? Did you bring your favorite panties, heels, or maybe a cute and skimpy skirt?”
Mike took a deep breath and said “I brought three wigs and some stuff.” “Three wigs, Mike? I only wanted two.” Mike blushed and replied “I brought one for me. Shoulder length strawberry blond.”

Standing up Jackie made a display of smoothing her nylons from her ankles to her thighs, adjusting the tightness of one garter. Noticing that Mike was involuntarily licking his lips Jackie flashed Mike a pretty smile and suggested “Give my garter a little pull, feel the tightness. You may need to know the proper snugness someday”. Mike hooked a finger under one garter and pulled it slightly getting a sense of what Jackie had said. He held Jackie’s garter strap for a couple seconds, stroked her nylon covered leg with his other hand, and let it go. There was a soft snap sound as the elastic snuggled back into place. “It’s like having someone playfully snap your bra strap. Has anyone pulled your bra strap, Mike?”

Waiting a moment for the reply that never came, Jackie announced, “I’ll take your bag to my bedroom, you make us another drink and then join me at my vanity. I have a chair waiting. I also have something for those dry lips. Do you like red, Mike?” Jackie grabbed the bag and went to her bedroom.

The bedroom

Mike arrived in quick order with both beverages. He stopped just inside Jackie’s bedroom door and looked around; nice, neat and feminine. He saw the contents of his bag neatly piled on Jackie’s bed, several pairs of his panties, a tube of lube, and his boring white bra lay next to the wigs. He was puzzled about the folded nylons and the box of panty liners on the vanity. He knew he didn’t bring them.

Jackie was seated at her vanity. She saw Mike in the reflection in her mirror and motioned for him to take the seat next to her. He did. Both drinks were placed on coasters on the vanity. Without turning to face Mike, Jackie said, “Just watch for now.” She picked up one tube of lipstick, extended the lipstick, gave it a smell and rolled it back into the tube, pretending it was not quite right. “Fragrance is key to a lipstick. Some smell like wax. Choose carefully.” She held it in front of Mike’s nose for him to smell. “This smells like nothing, tastes like nothing so why bother?” Mike agreed.

Grabbing a second tube of color Jackie removed the cap, gave it a whiff, nodded and began to carefully apply the scarlet red she had pre-selected. Mike sat enthralled, watching every move. “Let me smell that please,” Mike requested. “That’s a much nicer aroma.”
Jackie then began applying her eye shadow, using small sponge brushes to blend colors; smoky black, a lighter gray and some gold highlight. She was getting slutty. Mike was taking it all in. Next came her jet black eye liner and, for Mike’s benefit, Jackie used her mascara and finished with an eyelash curler. Glancing over at Mike she announced, “Almost done.” Jackie picked up her diamond chandelier earrings and easily had them in place.

Turning to face Mike she asked, “Is this who you expected to open the door for you today?” “Wow, you look amazing!” Mike managed to say. Jackie leaned over, grabbed Mike by the chin, pulled him closer and proceeded to kiss Mike on the lips. She made an effort to transfer as much of her lipstick as possible on to Mike’s lips. She broke the kiss with a loud smack sound and told him “I just fixed your chapped lips. Lick your lips and taste the scent. Nice, eh?” Mike was obviously in a state of bliss. The lump in his pants was also obvious.

Grabbing Mike’s chin Jackie closely inspected his lips. “Nope, this won’t do. You need more lipstick if you want full coverage. You do want better looking lips, right?” She handed Mike the open tube of lipstick. “Here doll face, do it the right way.”

With barely a hesitation Mike took the tube, leaned in towards the mirror, and carefully applied the scarlet red. Without looking around Mike lamented “This color doesn’t match by skin tone, it’s to stark.” Without being asked Mike picked up the mascara and stroked his eyelashes. Following Jackie’s lead he used the eyelash curler to give them a good crimping. Looking into the mirror he could see Jackie behind him. Jackie had assumed her now classic ‘lingerie mode’ stance. Her hands were on her hips and she was standing at the foot of her bed.

Mike stood and turned around to face Jackie. “I think you look good in lipstick, Mike, and your eyelashes make your face pop. Very nice; it’s a good start,” she said. Mike was happily grinning. A few moments passed as they stood there looking at each other. In a low sultry voice Jackie announced “Mike, it’s time to remove your clothes, right? That is part of our deal, right? You already have your shoes off; that’s when I saw your nylons, remember?”

Mike removed his shirt and hung it on the back of the vanity chair. He was nude up top. Next he dropped his pants and tossed them on the bed. He was only wearing a pair of elastic top, black, thigh high nylons. No panties. His penis wasn’t flaccid and it wasn’t erect. It appeared to be an above average eight inch with normal girth; nothing too scary. Jackie was staring and wondering to what degree she would have to be involved with it. Hands, lips or both? She had no experience, other than porn, as what to do.

“Mike, select one of your panties and put them on, ok?” Mike shuffled the panties around and selected a navy blue pair of briefs and pulled them on. Jackie continued, “Your choice in stockings is good but in the long run they become too much work. The elastic top weakens, they begin to droop and you spend your day trying to pull them up with your pants on. Eventually you’ll need a garter belt to keep them up or just switch to a garter belt and stockings now. Your other option is pantyhose. There are many styles, with and without patterns and they are convenient. The silky ones feel very nice. Have you worn pantyhose before, Mike?” Mike nodded yes.

Jackie went to her dresser and poked around. While she was looking for just the right thing she said, “Yesterday you said that you like wearing lingerie and feeling slutty, that it makes you very horny, right?” Mike quietly said, “Yes, I said that because it’s true. I get feelings and desires that I can’t explain.” Taking a matching navy blue camisole from her drawer Jackie walked over and handed it to Mike. “Here, put this on. It matches your panties and will make you look more femme. It will have to do for today.” Jackie was standing directly in front of Mike as he pulled the cami on.

Tell me what you told me

“You know what else you told me yesterday, Mike? You told me that you find me attractive. There’s one more important think that you told me. Do you remember, Mike? Tell me what else you told me yesterday. I need to hear it again.” Jackie reached forward and felt Mike’s panty encased dick. Keeping eye contact Jackie rubbed Mike’s dick, as sensuously as she could. “Does this make you feel alive, Mike? Does this make you horny, Mike? I think so, based on how big you’ve gotten. Your breathing has gotten a little rough, hasn’t it?” Mike nodded but didn’t move. His cock was protruding above his panty. Still keeping eye contact Jackie used her thumb to spread his pre-cum around and around his dick head. Mike was lightly shaking.

Using her other hand Jackie started to lightly stimulate Mike’s nipple through his camisole. Jackie leaned closer and whispered “Tell me what else you told me, Mike. We both know what you said. Tell me again, I’m waiting.” Mike closed his eyes and said “I want to have sex with you! I really want to have sex with you. I’ve never done this before but I want to have sex with you!” Jackie smiled and moved her hand so she could rub up and down Mike’s dick. “There, that wasn’t so hard to say, was it?”

Standing on her toes Jackie kissed Mike on the lips. Not getting the response she wanted Jackie kissed him with more passion than before. At the same time she slipped her hand into Mike’s panties, circled Mike’s cock at the base, her skin on his skin. She gently drew her circled her fingers tighter and stroked lightly up and down his shaft. She felt a throb. Mike’s kissing improved. “Mike, what did you say you wanted?” Mike made a slight forward thrust and gasped “I want to have sex with you!”

Jackie took Mike’s right hand and held it against her dick and made a conscious throb of her penis so Mike could feel it. Jackie moved Mike’s open palm up and down her stiffening shaft. Mike moaned. “Take my panties off, Mike. I need my panties off.” Breaking from their kissing Mike knelt down and helped Jackie step free. Her cock sprang eye level with Mike and was pointing toward the ceiling. Mike stared at it. “How do you want to do this, Mike?” asked Jackie.

Mike gently grabbed Jackie’s shaft and inspected it for a moment. Taking a deep breath, Mike slowly pulled Jackie’s penis closer to his mouth. He looked up into Jackie’s eyes, extended his tongue, and licked her cock head a couple times. “What do I do now?” Mike panted. Jackie looked down and said, “Try kissing it, Mike. Leave your lip print on it.” Mike kissed Jackie’s cock head and held his lips against it for a moment. Pulling back Mike looked at his lip print on Jackie’s cock. He circled his hand around the base of Jackie’s shaft and ran his grip up and down Jackie’s dick a few times just to see what it felt like to stroke a man’s penis. Jackie made sure to properly throb for Mike’s education. Looking up at Jackie, Mike pulled her cock back to his lips and kissed it again, this time below her glans, leaving another red lip print. Mike was finding these acts very erotic. So did Jackie. They both watched Jackie’s dick grow taller. Mike could feel the difference in Jackie’s firmness with his lips. It made his heart beat increase and his penis too.

“Are you feeling slutty yet, baby doll?” Jackie asked in a low, sultry voice. “You make me feel so good… and hard… and horny. Are you horny, Mike?” Mike softly squeezed and stroked Jackie’s shaft in reply. Fondling Jackie’s penis was becoming addictive. Jackie gave him the twitch he was looking for. Mike smiled.

Going down

Knowing the answer, but actually looking for approval, Mike asked, “Now what.” There was urgency in his voice. While waiting for a response Mike continued to gently stroke his hand up and down Jackie’s shaft. He was exploring what another man’s dick felt like. Jackie sent out another sex throb. Mike smiled at this twitch.

“Do what would make you feel good, Mike. Most girls put the dick in their mouth, seal their lips around the shaft, and suck and swirl their tongue while going up and down the shaft. Think of your mouth as the hand you jerk off with. Just go with it. Lubricate it with your tongue. Make it slippery. Bob your head if it feels right. Go faster when I’m about to cum.” Placing her hand on the back of Mike’s head Jackie gently guided him back to the task at hand.

Still on his knees Mike immediately got the hang of things and was giving an above average blowjob. Jackie had her eyes closed and was moaning and smiling at the same time. With a free hand Mike was slowly giving himself a hand job in slow rhythm with his sucking. Mike had made it to the base of Jackie’s cock more than once; Jackie began making subtle thrusting moves. “Darling, I’m getting really close… get ready!”

Mike made a final dive down Jackie’s penis. He sucked and licked and swirled his tongue, Jackie’s cock head was well back in his throat. … Jackie let loose. Several waves of cum erupted from Jackie’s cock. Mike didn’t spill a drop. He made a couple gulping movements and then a final upward cleaning suck keeping his lips sealed. Jackie’s dick popped free. Mike swallowed but remained on his knees as he recovered from giving his first blowjob. He wiped his mouth with the back of his hand. Jackie grabbed one of his arms and helped him stand.

Jackie hugged Mike and kissed him passionately on the lips. She made sure to use her tongue with the kissing. “Oh, darling, I can taste myself on your lips and it makes me feel slutty. You were superb.” Jackie made a point of rubbing Mike’s cock through his panties. His bulge felt nice. “Thank you for a great time. Come sit at the vanity for a bit. Have sip off your drink.” Mike did as he was told. After a short while Mike looked into the vanity mirror and reapplied the scarlet red lipstick, pressing his lips together for even coverage. “Where did all my lipstick go?” he asked. Pointing to her almost flaccid penis Jackie said “Look”. Mike turned and saw several red rings on Jackie’s dick. “Very impressive, Mike, you left me some trophy rings! By the way, wearing lipstick when performing a blowjob not only acts as a lubricant it also protects your lips from chaffing.” Mike nodded.

Sitting next to Mike Jackie ran her fingers through his hair and tried to sooth and calm him. “So how was it, baby doll?” Mike smiled and said “It didn’t taste bad at all and I liked the way I could feel you throb in my mouth… I felt super slutty and horny.” Taking a sip off her drink Jackie went to her lingerie drawer and brought back a navy blue 38B underwire pushup bra and a pair of breast enhancers. “Lift your arms, baby” Jackie instructed. Jackie removed Mike’s cami and placed it on the bed. Jackie put the bra on Mike, hooked it in the back, adjusted the straps, inserted the tit augmenters and pulled the cami back on Mike. “Your new tits look good on you! You earned them.” Noticing her gold hoop earrings on the top of her vanity Jackie picked them up and slipped one into Mike’s left ear. Handing Mike the other one Jackie said “You insert the other one. Stay here and I’ll be right back. Give me your drink glass.”

Jackie did some thinking while she mixed them fresh drinks. Returning to the bedroom she saw Mike was sporting both hoop earrings and was adding more mascara. His new tits were a definite improvement. Jackie sat down next to Mike and told him to close his eyes. “I’m going to add some eye shadow to show you what a little accent can do for your eyes. Next I’ll use eyeliner for an even better effect. Hold still.” A few minutes later Jackie was done. “Open your eyes, baby doll.” Mike slowly opened his eyes and checked his reflection in the mirror. He broke into a wide smile and said “Wow! My entire face looks better. I love what you did with my eyes.” His hand involuntarily fingered his earrings. He leaned over and gave Jackie a gentle kiss. “Thank you” he said. Jackie returned his kiss with more ardor and said “I’m glad you came over today Mike; it makes me feel pleasantly slutty too.” Jackie tweaked Mike’s panties and kissed him again.

Jackie handed Mike his drink. “To us!” Jackie said. Mike smiled, echoed the toast and they both took a swallow. Jackie put her hand on Mike’s knee and said, “I can’t call you Mike anymore. You’re much too pretty to be called Mike and after what you just did to my penis you deserve a new name. You earned it.

(To be continued)

Previously

“Wow! My entire face looks better. I love what you did with my eyes.” His hand involuntarily fingered his earrings. He leaned over and gave Jackie a gentle kiss. “Thank you” he said. Jackie returned his kiss with more ardor and said “I’m glad you came over today Mike; it makes me feel pleasantly slutty too.” Jackie tweaked Mike’s panties and kissed him again.

Jackie handed Mike his drink. “To us!” Jackie said. Mike smiled, echoed the toast and they both took a swallow. Jackie put her hand on Mike’s knee and said, “I can’t call you Mike anymore. You’re much too pretty to be called Mike and after what you just did to my penis you deserve a new name. You earned it.”

The story continues

As Mike continued to sit at the vanity Jackie looked around and located Mike’s strawberry blond wig. Bringing the wig and a wig cap over to where Mike sat, Jackie fitted the wig cap to Mike’s head, carefully brushed the wig, and positioned it into place. Facing Mike Jackie stepped back to make sure all was right. A few more brush strokes gave Mike some nice looking bangs. “Strawberry blond really looks good on you. You look pretty and more importantly it makes you look very girly. What do you think?” asked Jackie.

Mike stared, in awe, at his image in the vanity mirror. He shook his head to make his new hair toss about. His gold hoop earrings gently tapped his cheeks as he shook. Stopping to stare longer at the pretty image in the mirror he smiled and said “”That’s a pretty cute girl looking at me.” Picking up his tube of lipstick he leaned forward and applied more lipstick in an effort to create the ultimate image of a woman playing with her makeup. Looking up he giggled and lamented “I’d love to see what I’d look like if I was doing this but was only wearing a chemise!”

Jackie chuckled and quipped “That image (as she pointed to the reflection in the vanity mirror) would make a very interesting photo on your Christmas cards!”

Jackie stepped behind Mike with a brush and two scrunchie hair bands and she quickly created a sexy, double sided, ponytail. Each ponytail stuck out and gave Mike a young school girl look. “There’s so much that you can do with long hair. Look how this shows off your earrings.” Leaning over Mike’s shoulder Jackie gave Mike a quick kiss on his neck. “You’re looking very gender fluid at the moment” Jackie noted.
Looking at Mike’s reflection in the mirror Jackie gave his bra strap a playful snap. “Like I said you’re much too pretty to be called Mike.”

Goodbye Mike

Sitting down on the vanity seat Jackie placed her hand on Mike’s knee and asked “What do you think about ‘Michelle’ with ‘Mickey’ as a nick name?” Mike gave it a thought and said “Michelle sounds nice.” They toasted to Michelle. Michelle leaned over and gave Jackie a deeper, tongue involved, lover’s kiss. Michelle gave Jackie’s panties a reciprocal tweak. It was a beautiful thing.

Jackie pulled on a fresh pair of panties, redid her lipstick, and suggested that they return back to the living room couch for awhile. “Bring your drink, Michelle”. Before exiting the bedroom Jackie grabbed a bottle of nail polish and a pair of the custom pantyhose she had made. “Let me paint your toe nails while we talk and relax, ok? Remove your thigh highs.” Michelle did.

Jackie reached over and gave Michelle’s bare leg a gentle stroking. “Wow, you’ve got some smooth legs! Smoother than mine and I shaved my legs this morning just for you. I guess you are serious about exploring your female side” Jackie said. In reply Mickey said. “I’ve been shaving for years and have recently tried a crème. I’m not sure if it’s worth the hassle but I really like smooth legs and armpits.” He smiled and leaned back on the couch.

Shaking the bottle of blue polish Jackie asked what sort of experiences that Michelle would like to experience, what sort of help she wanted in looking feminine, how feminine did she want to go, how slutty, how permanent should these things be, and a variety of other questions. In short time all ten toes were painted bright blue. Jackie told Michelle that her blue toes would remind her of today. She applied a coat of polish ‘quick dry’ to speed up the drying process. It sure beat having to blow on her toes for five minutes.

Eventually the subject returned to ‘what next’. Michelle sat quite, in deep thought, for a period of time and had painted her own finger nails on her left hand before she spoke. “You know how I said that I want to have sex with you? I meant it. More precisely, because of your porn video, I more precisely mean that I want to have sex with you in me! I want you to fuck me and never tell anyone. That, and other reasons, is why I’m paying you $75k a year. I just want you to be gentle with me.” There was that sound of desperation that Jackie was glad to hear.

Jackie mulled over what she was just told. “No problem, Michelle, I’ll be gentle. I brought you some special pantyhose that will help us both. Your nails are dry so remove your panties and put these on. I’m going to need full access. ” Michelle found the front of the pantyhose, rolled them up as needed and easily pulled them up her legs nonchalantly smoothing them up her legs. The silky style looked great on Michelle. Jackie noted her familiarity and ease in her donning hose.

Noticing that there were two holes in the pantyhose Michelle asked. “What’s with the holes?” Jackie stuck her hand into the front hole, grabbed Michelle’s penis, and pulled it out. It looked funny hanging out like that. “The pantyhose will add to the experience. They are very silky and will enhance your feeling of being slutty and feminine. The feeling of two people fucking while both are wearing pantyhose and making love is not to be missed. It’s a beautiful thing.”

To the bedroom

“Let’s go to the bedroom, Michelle.” Michelle was leading the way. “Ok Jackie, why the opening in the rear?” Rather than say anything Jackie slipped her middle finger into Mickey ass crevice and poked her sphincter, maybe gaining a half inch of penetration. “Oooo! I think I understand.”

“Michelle, let me give you a quick explanation of what you’ve asked for and what we’re about to do. But first, I think I need a work-at-home provision added to Jack’s contract, don’t you?” Michelle stopped walking, turned to face Jackie, let out a laugh and said “Done! I might have to set up an office at my mountain home too.” Michelle hugged Jackie and gave her a sensuous kiss while rubbing her butt.

“Before the night is over you will have experienced your darkest secret (more than once), you’ll have been on your back and have had your legs over my shoulders. We will have gone through a half tube of lube and half a half box of those lambskin condoms. If you really want to feel slutty we could do it bareback… use no condom. You’ll imagine sperm wiggling around in your deepest orifice. It might enhance the slut feeling you’re searching for.”

Reaching her bed Jackie picked up the other pair of special pantyhose, cleaned off the bed, placing all items on a nearby chair, making sure to have a tube of lube within arm’s reach. Jackie placed a few hand towels and a box of baby wipes near the head of the bed.

Taking Michelle by her hand Jackie guided her to the foot of the bed. Jackie had Michelle stand with the back of her legs touching the bed. Jackie stood in front of Michelle and gave her a warm hug and a soft kiss. “Are you ready for this Michelle?” Michelle nodded and in a barely audible whisper said “Yes…I’m ready. I want you in me; I want you in me bareback. I want to see if I can feel the little swimmers.” They both giggled at Michelle’s joke. Jackie removed her panties, sat on the bed and slipped into the same style of silky pantyhose that Michelle was wearing. She stood up and walked over to Michelle to try to ease her mind about what was in store for her.

“Baby doll, here is what needs to happen. You need to make my cock as hard as possible. A repeat of the earlier blowjob would work quite well. We’ll use the wetness from what you leave on my penis as lubricant. You’ll lay on your back, on the bed, with your legs bent. I’ll crawl up between your legs and we’ll wing it from there. I will be using that other hole in your pantyhose. If we have problems we have KY on standby. I’ll be very slow and gentle. Eventually, out of pure horny lust, you’ll probably hook your legs over my shoulders so I can get in you as deep as possible. I want to feel your vertebrae with the head of my dick. You may be able to feel me squirt. As a favor for me, when you feel that, clench my dick with your sphincter muscle once or twice. It adds to my experience and may add to yours too. Especially as I withdraw. Clench and see if you can feel the veins in my shaft as I slowly pull out. I hate to be so clinical. When we’re done and rested I have a favor to ask of you. Ready?” Michelle grabbed my face and gave me a very passionate kiss. “Yes, I’m ready. Now shut up and let’s do it.”

Shut up and do it

Michelle reached into Jackie’s pantyhose hole and extracted Jackie’s penis which was already beginning to firm up. Jackie told Jackie to hold on a minute and she quickly went to the vanity and applied another coat of lipstick. Returning to Jackie she said “Sorry, I don’t want chapped lips”. She took hold of Jackie’s penis and slid to her knees and flipping her long blond hair out of the way. She began jerking Jackie off to get her hard enough to fellate. As soon as Jackie’s penis was pleasantly rigid, Michelle began sucking Jackie into her mouth. After few minutes of head bobbing, Michelle had accomplished in making Jackie hard enough for her penetration. Michelle was tempted to continue the blowjob to ejaculation but decided she had more urgent needs.

Michelle was scooting back on the bed, pulling Jackie by her wrists, up and between her legs. ‘Dang, this girl is anxious’ thought Jackie. Michelle had her legs bent and Jackie was kneeling in place. Jackie leaned forward and went in for one more kiss. Jackie too was excited since she had never fucked a man before. It was going to be a first for both of them. Being with a man was high on Jackie’s fantasy list.
Sensing a need, and to make Michelle’s first time easier, Jackie used a generous amount of KY jelly to grease her shaft thoroughly.

Widening the hole in Michelle’s pantyhose Jackie inched forward and had her penis at Michelle’s anus. Jackie was just about to begin penetration when Michelle reached down and pulled Jackie into her about an inch.

Unknown to Michelle was that this was Jackie’s first experience with this kind of sex. Jackie talked a good show but was totally improvising everything. Porn and locker room gossip was the basis for what appeared to be her prowess. Also unknown to Michelle was that Jackie was a virgin and yearned to be on the receiving of a man’s penis. For these reasons Jackie wanted to watch Michelle’s face as she was being fucked. She wanted to know what she could expect.

Michelle’s virginal tightness was an obstacle they both had to overcome. Being highly motivated, and with Jackie being compassionately gentle, full penetration was achieved. Jackie began slow fucking Michelle, partially withdrawing with each thrust, so that she could feel Michelle’s tightness with each stroke. “Are you doing ok, baby doll?” Jackie asked. “Relax yourself and it will get easier.” Michelle nodded and Jackie felt Michelle loosen up. Jackie picked up the tempo and she watched Michelle begin to smile. Michelle began to arch her back and was soon meetings Jackie forward thrusts.

As predicted by Jackie, Michelle soon had her legs over Jackie’s shoulders to attain maximum penetration, and was eagerly humping towards her first anal orgasm. The sexy feeling of their nylons rubbing and sliding together was indeed sensuous. The slick friction and sound of the materials rubbing together enhanced the moment for them both.

Pulling back a little Jackie made an effort to rub his cock head into and along Michelle’s prostate. She must have found her target as Michelle began rapidly thrusting her pelvis up to meet Jackie’s down stroke. Michelle’s eyes rolled back, she let out a load groan, and maintained her upward arching of her back. She quivered, she shook and she clenched Jackie’s shaft with her rectal muscles repeatedly and shot a stream of her warm sperm up her belly and onto her chin as she orgasmed. Michelle collapsed back onto the bed and lay still with Jackie still deep within her. Jackie shot a penile throb out to Michelle and Michelle reciprocated with a clenching of her own. They both giggled and clenched again.

“Did that feel good, baby doll?” Jackie asked. Michelle whispered “That was great… it was orgasmic.” Leaning down to kiss Michelle she used two fingers to collect some of Michelle’s goo that was on her chin. Making sure that Michelle was watching Jackie made a show of licking the sperm from her fingers. Michelle was wide eyed. Scooping up another glob onto her fingers Jackie extended her fingers and offered some to Michelle. Maintaining eye contact with Jackie Michelle sucked her seed from Jackie’s fingers performing a mini blowjob on Jackie’s fingers. A last swirl of her tongue and Michelle laid flat to relax.

Jackie was about to pull out of Michelle when Michelle grabbed her by the waist and said, “Be slow.” Jackie felt Michelle clench down on her penis as she began his withdrawal. ‘Damn, she is trying to feel my vein!’ Just as her dick popped free Jackie said “Baby doll that was a slutty move.” Michelle smiled widely at the compliment.

Reaching for baby wipes and towels the couple cleaned up a bit and then lay on their backs, side by side, staring at the ceiling. Jackie imagined that she could hear Michelle purring. Michelle grabbed Jackie’s hand and pulled it to her lips and kissed it. “Thank you, Jackie. That felt better than I imagined. I’m sure glad I came over today. I was very nervous about how things would go. You’ve made me feel so relaxed and special. I don’t feel like a pervert being with you. It all seems so natural.” She kissed Jackie’s hand once more and then dropped their hands to the bed. Holding hands, with their fingers interlaced, they allowed themselves to recover.

Jackie rolled over facing away from Michelle, and encouraged Michelle to spoon her. Michelle pulled Jackie back until they were snug and tight. Michelle was enjoying feeling Jackie’s heart beat. She leaned forward and kissed Jackie’s neck. “You smell nice” Michelle whispered, “And even without your wig your hair looks nice. Your face and nails add to your beauty.” Michelle shot Jackie a penile throb as her penis was laying against Jackie’s butt. Jackie smiled. Reaching behind her Jackie touched Michelle’s penis and gave it a brief squeeze.

“Remember when we got on the bed that I said I would ask you for a favor when we were done?” Michelle had her eyes closed as they lay there almost entwined and managed an “Um-huh. Why do you ask?”

Jackie slowly sat up and turned to face Michelle. Looking into each other’s eyes Jackie picked up and held Michelle’s hands. “You said that you wanted to feel me inside of you, right?” Michelle nodded an affirmative ‘yes’. “I want you to be inside me. I’m a virgin and can’t think of a nicer person to give my cherry too.” Jackie pulled Michelle forward and they shared a passionate kiss.

Michelle paused a moment and said “When I first got the idea of us being together I was only interested in giving blowjobs and being taken from behind. I never really thought about being fellated or in giving anal sex. I guess I’m more of a ‘receiver’ than a ‘giver’ but I could do it, on occasion.” Jackie smiled, leaned closer, kissed her and whispered “How about helping a girl out? I need to feel what you felt. Now. You won’t know that you like or don’t like it unless you try it.” Jackie reached over and grabbed Michelle’s penis as it drooped from her pantyhose. Giving it a few gently strokes Jackie could feel it begin to swell.

Jackie leaned back and got her tube of lipstick from the vanity and returned to facing Michelle. Establishing eye contact, Jackie expertly painted her lips and tossed the tube up by the pillows. As a token of sincerity and proof of her urgent need, Jackie leaned forward, grabbed Michelle’s shaft, leaned over and kissed the top of her cock. Michelle throbbed against Jackie’s lips. Embolden by her first dark red lip print Jackie hefted and felt Michelle’s penis, gently squeezing and exploring. It felt soft and smooth. Unknown to Michelle, Jackie had never been with a man and had never touched another penis.

Looking into Michelle’s eyes Jackie pulled Michelle’s penis over to her mouth and gently gripped it, with her red lips, just behind the glans, pressing her lips snugly together, in an effort to leave a red ring, Jackie tickled Michelle’s penis with her tongue. She sucked in another inch of meat and re-gripped the shaft lower with her lips. Jackie ran her tongue up, down and around. ‘My god, I’m actually sucking a man’s dick”. Jackie could feel the penis stiffen as she sucked and licked it. Michelle clenched out a throb to tell Jackie ‘thanks’. Jackie went back down Michelle’s shaft as far as she could go and began a slow, sucking withdrawal using her tongue in a way that she liked done to her. Her mouth popped free with an audible sound.

Holding Michelle’s penis, like it was a garden hose, Jackie used her thumb to smear the pre-cum around and around the tip. Michelle sent Jackie an involuntary throb. Jackie leaned closer and gave Michelle a kiss, never stopping her thumb action. ”Well” she whispered, “could you help a girl out?” She bent over and gave Michelle’s erect penis another kiss. “Please” Jackie asked. ‘I can’t believe I‘m begging to be boned! Latent fantasy or not I hope it satisfies my curiosity’ thought Jackie to herself.

“If you want me to help you out you better stop with your thumb action.” Michelle said. Taking that as a ‘yes’ Jackie quickly moved to the end of the bed and sat with her feet on the floor. Motioning Michelle to come over Jackie grabbed Michelle’s hand and pinned her between her legs. She reached to the side of the bed and picked up a tube of lube. She removed the top.

Michelle, and her raging erection, were both ready. Jackie grabbed Michelle’s smooth penis and kissed and bobbed her head up and down it a few times. She used her tongue to shove it from her mouth. Holding Michelle’s erection with one hand Jackie used her other hand to squeeze out a thick line of lube along Michelle’s entire penis; from tip to shaft and back again. Putting the cap back on she tossed the tube back onto the bed. Jackie had an odd grin on her face. “I want it bareback too, baby doll.”

Jackie took hold of Michelle’s dick and began lubricating the entire length with long, slow pulls up and down her shaft. The gel was very effective and soon Michelle’s shaft glistened in readiness. Jackie wiped the leftover lube onto her own dick enjoying the slipperiness that would aid her first penetration. ‘God, I’m so damn horny’ thought Jackie. She leaned back onto the bed and used her legs to pull Michelle closer. “Let’s try it with you standing and we’ll move onto the bed if we have to.”

Jackie pointed her legs at the ceiling, reached back and spread her butt cheeks through her pantyhose. Michelle poked her penis through the rear hole in Jackie’s pantyhose and into Jackie’s sphincter with her cock head and stopped. Using her cock Michelle made a few circles around Jackie’s opening which helped spread the lube. Michelle noticed that Jackie’s hole was making little puckering moves of anticipation. ‘Her butt is trying to kiss my dick!’ thought Michelle. “Lean forward so I can rest my legs on your shoulders.” Jackie requested.

Michelle took a deep breath, thrust forward a little and slowly began the insertion, sliding in almost two inches. The pair of them both gasped in unison. “Wow” said Michelle, “Arrrgh!” said Jackie. Michelle pulled back and repeated the process gaining more than three inches entrance. Applying almost no pressure Michelle could feel Jackie relax and stretch. It sounded like Jackie was doing yoga or Lamaze breathing exercises. Still applying very little pressure Michelle watched in awe as her penis was slowly sucked in to Jackie’s warm ass. Her penis began to disappear deeper and deeper. “Hold on a minute”, Jackie gasped. “Let me catch my breath.” Michelle held still. Wiggling her butt and adjusting her legs so as to get more comfortable Jackie gasped out “Ok… I’m ready.”

Michelle quickly pulled back and just as quickly thrust forward. Jackie gasped. Michelle repeated her in and out technique three more times, savoring the warmth and uniform tightness around her shaft. It felt really good! Trying to be cute Jackie clenched down on Michelle’s dick and maintained a firm rectal grip. Michelle slowly pulled back enjoying the way Jackie’s sphincter milked her cock. “Jackie, I gotta tell you, I think you made a convert out of me. This feels fucking great! Our pantyhose’s rubbing together makes it even better.” Jackie had a double handful of bedspread in an effort to steady herself.

Michelle fell into a pleasant, steady rhythm that was working well for them both. Her strawberry blond hair swayed to the rhythm. Jackie had become passionate with experiencing her first fuck. She clenched, she grunted at each thrust, she wiggled and was making upwards thrusts of passion. ‘God, it is good!’ Jackie thought.

In an inspiration of lust Michelle partial withdrew from the sanctity of Jackie’s bowels. Michelle transferred some of the KY from her dick into the palm of her hand. As she thrust forward into Jackie Michelle wrapped her greased hand around Jackie’s easily available penis and began jacking her off. Jackie screamed loudly, “Don’t stop! Go faster! Faster, I’m so close…!” There was no mistaking the urgency in her voice.

Michelle was also close to orgasm and the tension was extreme. When the moment happened she yelled “Fuck!” thrust forward, and ground her shaft as deep as possible into Jackie. She shoved Jackie a foot further up the bed with just her dick and then spewed her warm seed deep in Jackie’s bowels. The feel of Michelle squirting was all it took to push Jackie over the edge into a sensory over load orgasm.

Jackie bucked upwards several times and wrapped her legs around Michelle, not wanting to let her pull free. Jackie blew her load and it leapt up to her neck and chin. It felt warm as it hit. Jackie relaxed and began softly crying, her legs hanging limp off the edge of the bed. Michelle pulled out. “That was a beautiful thing” Jackie sobbed. Michelle got on the bed and started trying to comfort Jackie, stroking her hair, kissing her face and whispering “It’s all good, all will be fine, take a few deep breaths, there, there…” Michelle grabbed a few baby wipes and began cleaning cum off of Jackie as well as the wet results of their act from her penis.

Jackie scooted herself further up the bed and laid back to compose herself. Michelle lay next to her and began kissing her forehead and eye lids. “Are you ok? Can I do anything for you?” Michelle asked. Jackie looked over, wiped her tears away, smiled beautifully and said “No, I’m ok… it’s just that… I mean… wow! I’m not sure what I expected but this moment was fantastic! How was it for you baby doll?”

Michelle flopped onto her back, stared at the ceiling and began talking. “I had no idea. I told you that I wasn’t keen on fucking people in the ass. What we did here, today, has changed my mind forever. I’m a new man… I mean, I’m a new woman. And I owe it all to you. Maybe it was the way you clenched and milked me, maybe it was because I felt so damn horny.” “And did you feel slutty?” Jackie probed. Michelle turned on to her side and faced Jackie. She smiled and gently stroked Jackie’s cheek. “Jackie, you have made me feel very slutty… and naughty and…and horny… and pretty. I can’t thank you enough. My wondering about how I could experience the things we’ve done just today are over. It could not have been any better. I’m glad I came over. There’s so much to look forward to.” Pulling Jackie closer Michelle gave her a lingering kiss of passion. “Anything else, baby doll?’

Rolling back Michelle sighed and said, “Not only did you make me feel slutty you gave me the chance to be slutty. Never in my wildest dreams did I think that I would ever give someone a blow job, be up their ass, have someone pleasure me anally, wear lingerie and makeup… or hire a full time sex partner/gender trainer” Jackie was thinking the exact same thing about her day! “You did fine on all accounts baby doll.”

Jackie gently tugged on Michelle’s hoop earring and said “It’s getting late baby doll and we have so much to do, you have so much to learn and we haven’t even tried on our beautiful wigs yet, you only have nail polish on one hand, and I’d like to see you in 3 inch pump heels.”

“We need to plan how you can wear some of your sexy lingerie under your male clothes at work and in off work activities. With a little planning we can have you wearing a bra, panties, garter belt and stockings, jewelry, light makeup, lip color, nail polish; so many ways to express your inner girly self. You need to let your hair grow so we have something to work with. Pixie shag would be a good start for you and it could easily be brushed into a guy look. You might like being adventuresome.”

Jackie crawled out of bed and immediately sat at her vanity. Applying a fresh coat of lipstick she began brushing her hair while explaining to Michelle what needed to be done today. “Let’s get out of bed and get on with our day. Come here doll face.“ She motioned for Michelle to come stand by her. Gently holding Michelle’s face Jackie expertly applied lipstick to her lips. Jackie then put a short smear of lipstick on Michelle’s and her cheekbones. “Blend it in with your finger tips and it makes a quick and easy blush. Add more if you want.” Leaning towards the vanity mirror Jackie showed Michelle what she meant, rubbing the colored streak into a healthy looking blush. Michelle followed the lead and smoothed in her own blush. “Wow, that sure makes a difference.” proclaimed Michelle. Michelle took the opportunity to add some mascara to her lashes.

“Pull off your pantyhose and get a fresh pair of panties” Jackie directed. “You may want to use the restroom and clean up a bit. I see you are dribbling a little down the back of your leg. Clean that up and I’ll help you deal with it later. I’ll use the restroom first and then we’ll meet in the kitchen. I have some deli sandwiches and chips that we can eat.” She gave her hair a brief spray of lacquer and then removed her bustier. She had kept that on for Michelle’s benefit.

Adjusting her bra Jackie got busy getting dressed in the same casual, but feminine ‘beach’, gear that she had worn the day before. The only difference was she used a fresh blouse. Michelle was observing her every move. Jackie was pulling on some pretty lace trimmed French style panties but stopped when they were just above her knees. Opening the box of Kotex Lite Days pads, that was on her vanity; Jackie removed and opened a thin pad. Peeling the adhesive from the back of the pad she pressed it into her panties. Looking over to Michelle Jackie said, “Look and learn. This thin pad will soak up any leakage that you may have from having bareback anal sex. It’s an easy way to avoid a messy or embarrassing situation. You’ll hardly know it’s there. It has little plastic wings that spread out and provides better protection from ugly wet spots soaking through your clothes. Sperm will leak out no matter what you do.” Pulling her panties completely up Jackie grabbed a pad and tossed it to Michelle. Michelle stared at it in amazement. ‘My little Jackie is damn resourceful’ she thought.

Following Jackie’s suggestion Michelle lowered her panties and affixed the pad and re-positioned her panties.

Jackie continued dressing and opted for new set of cocoa colored Silky pantyhose quickly pulling them on. Next came her mid rise jeans and a blouse. She slipped into a feminine pair of sandals and started for the kitchen. “I’m going to fix us some nice deli sandwiches and chips. Call me when you’re dressed. I have an extra pair of pantyhose if you’re interested. Oh, and for God’s sake, please toss out our dirty ones.” And then she was gone.

Michelle took the time to use the rest room and cleanup a bit. Looking in the mirror Michelle took a quick inventory of her situation: Matching Navy blue bra and panties, breast enhancers, camisole, cocoa colored pantyhose, beautiful shoulder length strawberry blond hair (with dual pony tails), makeup, eye shadow, eyeliner, mascara, dark red lipstick, blue toe nails and one hand with blue polish. Michelle giggled at her own image. She smiled widely at how feminine she had become in such a short time. She was pleased.

She was about to join Jackie at the kitchen table when Jackie came back in. “Whoa, there Missy, let me see what you have going there.” No doubt about it Michelle was looking nice. “We can’t have you running around in only your camisole and panties. I have a white tennis skirt with an elastic waist that will show off your great legs and add another layer of femininity.” Jackie opened a drawer, found what she needed and brought it over to Michelle. Holding the skirt open Jackie said “Step in to this baby doll.” Michelle did and Jackie pulled it into place.

Jackie gave Michelle a hug and walked them in front of the vanity mirror. “What do you see, Michelle? Do you see the two pretty girls looking back at us?” Michelle stood in silence admiring her female self. She made a point of flipping her hair. Jackie produced a cute tennis bracelet and a gold necklace for feminine effect. Clasping the tennis bracelet closed she stepped back to admire her creation. “Damn, you’re cute”. Michelle gave Jackie a good hug and enhanced it with a long kiss. “Thank you, my Jackie. Thank, you.” Still embracing, Jackie gave Michelle’s panties a good rub; there was a stirring. Michelle felt the need to grab Jackie’s crotch and was in the process of pulling on Jackie’s zipper tab. Jackie playfully slapped Michelle’s hand away saying, “Stop that! There’s plenty of time for that later. It’s time we ate. Oh, and by the way if you were to wear a control top pantyhose it would help make that cute little bulge of your less noticeable.” Michelle added this bit of information to memory. ‘Nice to know’ she thought.

They went and sat at the kitchen table where the sandwiches, chips and olives were waiting. They made idle chatter as they ate. Jackie finished first and went and retrieved the bottle of blue nail polish, shaking it as she was sitting down. Without asking she picked up Michelle’s unpainted right hand and began stroking on the first of two coats. “I want to thank you again for helping a girl out earlier. It felt so ‘right’.” Michelle lightly blushed at the reference to their earlier love making.

While Michelle’s nails dried Jackie took the opportunity to make them both a drink. Jackie took a sip of her drink and then sat the drinks on the table. “There are a lot of decisions that need to be made by both of us. You have to decide on how femme you want to go. One thing is clear you need to build a wardrobe, get some jewelry and accessories, find clothes and colors that will accent your potential and grow out your hair and nails. And you need to let me know how often you want to ‘see me’ and how frequently feminine you want me. Am I to always be girly for you? “Jackie stopped talking and enjoyed a sip of her drink.

Pulling her chair close to Michelle Jackie continued. “Look at my face, my eyebrows, my dyed eye lashes and my nails. I had this done for you. I don’t think I can return to our office like this. It would be difficult for both of us.” Michelle gently held Jackie’s face in her hands. She ran her thumbs over Jackie’s girly eyebrows. Taking in Jackie’s face, her eyelashes and red lips Michelle leaned in and gave Jackie a soft kiss. “You’re right again. You definitely would create a distraction if you showed up at work looking like this. You are so… so… so very ‘Jackie’. I think you’re beautiful.”

Placing her hand on Jackie’s leg, Michelle continued with “We could say that you were transitioning to being a woman. We could find you a new office or job site… you could be away on a special project for weeks, maybe we could make it work. I need to be near you.” Softly holding Michelle’s hand that was on her knee, Jackie pulled that hand and pressed it to her crotch. Jackie squeezed Michelle’s hand between her legs. “I just don’t want to be your office whore.” That remark got Michele’s attention.

Leaving her hand where Jackie had placed it Michelle began to speak and also began to seriously stroke Jackie’s crotch. Her thumb was at the bottom of Jackie’s zipper and her middle finger was at the base of where Jackie’s balls should be. She stroked and asked “Have you given these things any thought?” Jackie moved her chair closer so the finger tickling pressure would be more intense. Jackie pulled her zipper down in invitation to Michelle. Michelle took the bait.

“I think,” Jackie began, “that you and the corporation need a Director of Corporate Diversity that reports directly to you.” Jackie rolled the waist bands of her pantyhose and panties as far down as she could, wiggling to loosen her jeans more, exposing about half of her penis. “I also think that you need to find a nice, near bye, condo that could function as an office and a hospitality suite for you, me and special guests.”

Michelle took more of the bait and had fully gripped Jackie’s shaft and was slowly stroking Jackie’s shaft as Jackie spoke. She adopted the ‘thumb-on-the-cum’ method of petting, spreading Jackie’s natural lubricant around and around. Jackie gave out a soft gasp and slid even closer. “Many executives have private retreats and places to relax or conduct business. You can make it happen.” Jackie’s voice was sounding raspy and urgent.

Jackie leaned back and let Michelle tug her pants off. Jackie freed her cock from the remaining confines. As a tease Jackie made her penis twitch in Michelle’s hand. Michelle giggled and playfully called Jackie a ‘slut’. Maintaining a friendly grip on Jackie’s shaft Michelle pulled it towards her, bent forward and sucked in three or four inches of Jackie’s penis. Her tonguing felt so fine to Jackie. Michelle began bobbing her head up and down Jackie’s now slick penis while still milking her with her hand.

Jackie leaned back into her chair. Michelle got down on her knees. Within minutes Michelle had taken Jackie to heaven and back.

To heaven and back

Grabbing Michelle by one hand Jackie pulled her to the bed room to reciprocate a loving blowjob. Thirty minutes later Jackie was snuggling next to Michelle and was resting on her back with her eyes closed. She was holding Michelle’s hand and could have easily fallen asleep in her contentment. Michelle tugged on Jackie’s hand and said, “I don’t want you to be my paid whore and I wouldn’t expect you to be continually dressed as a female. I think it would be wonderful if you did.”

“I also agree that you returning to your job or office is out of the question. And you’re correct that I could justify the need for ongoing diversity training and a special projects manager. The idea of having an executive retreat, other than my mountain home, is superb. On a personal level I know I’ve found someone that could help me explore my feminine side; someone that could share my new found experiences that were, until today, only far off fantasies. You’ve taught me a lot in a very short time and I feel relaxed being with you.”

Sliding out of bed Michelle sat at the vanity touching up her lipstick, mascara and hair. She removed her dual pony tails and switched to a single pony tail. She was removing the hoop earrings she had been wearing and was inserting a pair of long drop earrings that were lying in view. Snapping on the back of the final earring Michelle casually said: “In short I need you. We could use your first initial on your business cards rather than ‘Jack’ until we arrange a formal name change. How would you like to be my Director of Corporate Diversity and Special Projects? $75k a year, reporting directly to me and working off site. Will you take the job or must I offer it to someone else?”

Jackie leapt out of bed and rushed to hug and kiss Michelle. After a long and sensuous kiss they separated long enough for Jackie to say “Yes! Yes! I’ll do it! We may need to add to my title: ‘Clothing, Makeup and Gender Coordinator’.” They broke into laughter at the thought.
Michelle was heading to the kitchen in order to make them another drink. Over her shoulder she said, “I’m glad your porn tape auto destructed so you have nothing being held over your head. You have the only copy. Maybe someday we’ll have a movie night and watch it together.” She laughed out loud.

“You knew my blackmail videos had disappeared! And you never told me until now!” Jackie almost yelled. “Yes, I knew. That means you did what you did without any coercion. You had sex with me out of your own free will. You really helped a girl out. I truly appreciate that. It proves that we can trust each other. We’ve shared some extremely intimate things today.” Putting her arm around Jackie Michelle pulled her close. “I never thought I would ever say this but I am very attracted to you. You’re intelligent, resourceful, well poised and… delightfully slutty.” Michelle pulled Jackie even closer, kissed her on the cheek and held her hand. “We’re a good match! What’s that expression? ‘You complete me’.

Suddenly Jackie’s future was even brighter. And they hadn’t even made it to trying on skirts, dresses, lingerie or casual girly clothes. There’s so much to do for Michelle. Jackie actually wanted to see how Michele would look in heels.

Unlike yesterday Jackie was looking forward to what lies ahead. Giggling inwardly, Jackie wondered if Jonny from work would actually leave her the tube of lipstick that he had promised, on her desk on Monday. ‘Sure hope his copy of my porn video evaporated to’ she thought. She was very confident that it had.

“I was thinking about taking on a roommate in a month or two” Michelle began. “And my mountain house is in need of a live-in house keeper.”

(The story ends… or does it? the options are many)

A word to the wise: Be careful what you click on!

Epilogue

Here is what prompted this story. Several sites offer gender morphing or adding makeup, hair, a magazine cover of you, etc. That’s okay. However, if you are NOT careful what you click on, the site sends your femme photo to your Facebook page and will be seen by all your friends! Those pretty photos of you could result in many interesting conversations if your femme side is secret.

http://www.clipquiz.net/?all=1

Instructions
1- Click "Login with Facebook and choose profile photo"
2- Accept permission so we can list your Facebook photos
3- click the photo that best shows your face
4- Wait for your result to be ready

I almost did this in error and thought about what sort of turmoil posting such cute photos would have stirred up. On another site I got to the “review image” part of my makeover and was able to ‘save’ my photos BEFORE clicking on the “accept and continue” options. Whew! So I do have several photos of my pretty femme self; they are not seen by anyone (that I know of) but me. Have fun out there but read the fine print.

Maybe you could create a new Facebook page, have no friends, and then morph to your heart’s content. Share if you find a solution. In the mean time “Be careful what you click on”.

Here’s other sites: https://www.esteelauder.com/virtual-try-on & http://www.morphthing.com/

Previously

Connie replied, “I’m looking forward to getting to our campsite too. My nipples are on high beam and are tenting my bra. Too bad I didn’t bring my underwire push up bra or I’d show you some real cleavage.”

Bonnie discreetly repositioned his penis to make walking easier. That action by Bonnie made Connie smile. It seemed as if they both had a fresh bounce in their steps; an urgency to reach camp.

With Connie’s help Bonnie began a slow and considerate penetration. It felt warm, snug, comforting and long overdue.

Day 2 - Morning

Connie woke to the sound of a crackling fire and the delicious aroma of fresh morning coffee. Yawning and stretching she tossed back the sleeping bag and began her day. Doffing her sleeping shirt she pulled on a gray sports bra and a cute denim romper. Her flannel long sleeve shirt would keep her shoulders warm. A pair of leg warmers would get her through the morning chill. Kneeling at her knapsack, she removed her leather purse; she produced a small mirror and a brush. She applied her lipstick, grabbed a pretty scrunchie and stepped out of the tent with knapsack and purse in hand.

“Good morning, honey buns. Thank you for a fabulous evening.” She walked over, dropped her knapsack and purse next to a log and gave Bonnie a happy hug and a sensuous kiss to the lips. Bonnie returned her kiss and obviously was trying to transfer Connie’s lipstick to his lips. Connie stopped her and said, “Hold on tiger… there’s enough to go around.” Removing her lipstick from her romper pocket she held Bonnie’s chin still and applied a coat of Copper Rose to her sweet lips. “This color really looks great on you. We always used a similar shade at your house when we were in school.”

Bonnie handed Connie a cup of coffee and the two sat on one of the large tree stumps near the fire. “Thank you. You’re very thoughtful.” After a thoughtful pause Connie added, “And you’re very virile too.” They both laughed and Connie scooted closer to Bonnie who immediately put his arm around her shoulders. They snuggled, watched the fire and drank their coffee.

Finishing her coffee Connie was brushing her hair and was about to make a pony tail when Bonnie told her “Let me do that for you. Do you have another scrunchie?” Connie reached into her purse, handed Bonnie two hair bands and the brush. She remained perched on the stump. Bonnie stood behind her and deftly brushed and parted her hair. Instead of a single ponytail she gave Connie two perky ponytails that stuck out in a playful manner. It was a good look on Connie. Peering into her compact mirror Connie’s eyes lit up. “Oooo, that’s so damn cute!”

Bonnie lowered their food supplies from the tree and Connie set about making breakfast. Freeze dried food packets made for an easy meal. Their single burner compact propane stove made food prep quick and easy.

Following breakfast Bonnie went in search of more firewood. Connie straightened the campsite kicking pinecones into the forest. She tidied their tent, zippered their sleep bag and arranged their belongings neatly inside. Needing to take care of her post breakfast ablutions Connie took a roll of biodegradable toilet paper and walked to the agreed upon latrine area and squatted.

Bonnie returned to camp and dropped a double armful of the evening’s firewood next to their fire ring. Not seeing Connie Bonnie called her name. Still squatting Connie shook a nearby bush and loudly said “I’m over here honey…” using a navy term she added “I’m using the head.” Bonnie laughed at the inside joke. “Do me a favor and reach into my purse by the log and bring me a fresh tampon please.”

Opening Connie’s bag Bonnie peered inside. Moving things around she saw panties, a clear zippered makeup case that contained a wide variety of girly things like mascara, lipstick, nail polish, tweezers, a travel sized pack of Pearl Lite Days tampons and travel sized hair spray.

Unzipping the bag Bonnie removed a single tampon. She returned the package to the makeup bag. Taking a closer look Bonnie saw there were also six ribbed latex condoms and a tube of lube inside Connie’s makeup bag! ‘I wonder why she decided to take it bare back? She sure has embraced her feminine self by having so many female items in her purse’ Bonnie thought. Closing Connie’s purse she walked the tampon over to where Connie was waiting.

Connie was standing with her legs spread about two feet apart. She had her hand outstretched toward Bonnie. Bonnie passed the tampon to Connie with a friendly, “Here you go.” “Thanks kissy face” Connie said as she started to squat. Bonnie returned to the campfire area. It was only a few minutes later when Connie emerged from the bushes. She had removed her morning leg warmers and quickly crammed them into her knapsack. She cleaned her hands with a baby wipe and tossed the tissue into the low campfire flames before joining Bonnie on the tarp.

“Sorry about getting you involved with my hygiene needs but either you squirted more than six times last night or you are a walking garden hose! You always seemed to make the biggest puddle in high school. I want to keep my romper clean for awhile.” She leaned over and gave Bonnie a kiss. She pulled Bonnie closer so she could lean on her shoulder. Bonnie tossed a couple of small branch parts on the fire in order to prolong the moment. They held hands like the young lovers they were.

Bonnie broke their reverie by saying “We need to plan our day. We need to get some water from the creek, we need more wood and I’d like to see if I can catch us a couple trout for diner. I think there are a couple of good fishing holes just downstream. I’d also like to show you a beautiful vista point with views of the desert in the distance.” Connie nodded in agreement.

About 11 AM.

Skies were blue with a few puffy white clouds. The temperature was perfect. Both yawned and stretched as they stood up. Connie refreshed her lipstick and tossed the tube to Bonnie.

Bonnie grabbed her backpacking ultralite fishing rod and reel and Connie picked up an empty three gallon collapsible water bladder. Connie followed Bonnie to the creek. They stood on the bank and listened to the water babble. “Get your water from over there where the flat rock is. You shouldn’t drink this water unless you boil it first. There’s no problem in using it to wash your hands and face. I should be back in an hour or two. Okay?” Connie nodded and said “Be careful, darling.”

What had been intended as a simple kiss goodbye escalated into some serious heavy petting. Connie had created an eye pleasing bulge in Bonnie’s pants and Bonnie had found easy access to Connie’s panties via her romper. Connie had hold of Bonnie’s zipper pull and purred into her ear, “Let’s go back to camp. I want to have my way with you!” Bonnie smiled and stepped towards the trail. “I’ll take a rain check on that offer until I get back.” She turned and headed down stream.

Connie filled the water bladder and returned to camp. After stacking the firewood she took a short walk around their private meadow. Finding several patches of yellow and blue flowers Connie gathered several bunches and returned to camp. Placing the flowers on the tarp in the shade of their protective log Connie rolled the tarp back and began gathering all the nearby pine needles that she could find. Using a fallen tree branch as a rake she spread the needles about four inches thick and then rolled the tarp over them. She sat down on her home made pine needle mattress and smiled. ‘Definitely a nice creature comfort’ she thought.

Feeling inspired she used another spare tarp and two sturdy sticks to create a nice sun shade over their new mattress. ‘My god, I made a honey moon bed!’ Her laughter scared a blue jay into flight. ‘I better make myself presentable’. Bringing her purse under the tarp awning Connie went to work. She took her tweezers and mirror to shape her eyebrows into a more feminine look. Using her lipstick she smudged her cheeks with color, rubbed it in and created a very respectable blush. She cut a yellow plastic bag and created accent ribbons that she tied in her two pony tails. Looking into her mirror she complimented herself on the way it made her hair ‘pop. Using more of the plastic bag she tied flower bouquets on each of the two awning sticks.

About 2 PM

Wondering what else she could do to look enticingly sexy Connie walked to the tent and opened her main back pack. She had an area where she kept cold weather items. She pulled out an unopened package of black tights. ‘Yes, as warm as thermal underwear these will complete the image I want Bonnie to see.’ Standing up she removed her romper and morning panties. In doing so she found her tampon string dangling. ‘Damn, sure glad I remembered this.’ Quickly removing the leak stopper she blotted herself, making sure she was dry, and put it in their trash bag. She carefully pulled on her black tights and then a fresh pair of black nylon tricot tap pants. Her penis began to grow as she relished the erotic feeling of nylon on tricot. ‘No time for this,’ she thought. She pulled on her denim romper, tugged her sport bra down into place and took a deep breath. She completed her ‘seductress outfit’ with her ankle socks and hiking boots. Connie returned to the lean-to she had just built.

Connie sat down on the pine needle mattress to catch her breath and wait. Her light headedness wasn’t all altitude related. Taking another look into her mirror she thought there was something missing. ‘Dang, no eye make-up!’ Connie thought. Delving back into her purse she found her mascara and gave her lashes a double coating of black. In a moment of inspiration Connie picked up a piece of charcoal from the fire ring. She used her index finger and rubbed it on the black coal. Transferring the black onto her eyelids she created the sexy dark eye shadow she liked. Staring into her mirror she re-did her lips, blew a kiss at her image and waited. She tossed her bag under the awning in case they needed a pillow. She lay back to rest and wait.

Bonnie returns

About 3 PM

Hearing Bonnie’s return Connie came out from under the awning. She stood, smoothed her clothes and perched on the big stump and struck a pose that she thought was sexy. Less than thirty seconds after she got settled Bonnie appeared from behind a tree. She remained silent.

When Bonnie looked up she smiled at her and said, “Hey, babe how was your day?” Bonnie stopped in her tracks, dropped her fishing pole and stared. Connie slid off the log and put her hands on her hips. Bonnie came within three feet and stopped again. Her eyes were ogling her and she loved it. She glanced at Bonnie’s crotch. She noticed her glance and began to smile. “I’ve found a beautiful forest nymph. You’re absolutely gorgeous. And you have yellow ribbons in your hair and black tights. You’re makeup brings out your features. How did you get those sexy eyes?” Connie replied, “I learned it in the Boy Scouts.” She did a 360 degree turn around.

Bonnie hugged her and gave her a ‘happy to see you’ kiss. Connie pulled her closer and returned her kiss. Looking over her shoulders Bonnie saw flowers tied to two posts. She broke off her kiss and asked, “You’ve made some improvements to our camp?” Grabbing Bonnie’s hand Connie tugged her to the pine mattress. “Feel how comfy this is. Duck your head and get under our awning.” Bonnie didn’t hesitate. “It’s our honey moon bed, babe.”

Their kissing and petting was becoming steamily intense. She had Connie stripped down to her tights and then removed her bra. Connie soon had Bonnie’s jeans completely off. Stopping just long enough to apply more lipstick Connie soon had Bonnie’s jockey shorts off and was eagerly performing a blowjob on her. Lipstick rings marked her progress as well as marking her territory. Bonnie had her hand wrapped around Connie’s rigid shaft. Connie had yanked her tights down for easier access. Following Connie’s lead Bonnie greased her lips with Copper Rose and rolled Connie to being on the bottom. She too was soon marking territory as she sucked and nuzzled Connie’s throbbing cock.

While still bobbing up and down on Connie’s shaft Bonnie used her other hand to finger Connie’s butt hole. Noticing that there was no longer a string hanging out of her Bonnie stopped long enough to say, “Oh, you pulled your tampon out. You must have been expecting me.” “No, not really”, Connie breathlessly said, “I didn’t want anything to spoil this moment. You want to know why I call this our honey moon bed? It’s because I’m taking your cherry right here.” Connie quickly slipped into a spooning position behind Bonnie. Connie grabbed her penis and began rubbing it up and down Bonnie’s butt crack. Pausing when she knew she was at Bonnie’s sphincter her penis probed forward and made partial penetration. Her pre-cum helped. Bonnie gasped at the intrusion.

“I don’t have any condoms but I have a lube that will make it nicer for us both.” Reaching into her nearby purse Connie had the top off the lube within the blink of an eye. Using her middle finger she made sure Bonnie was well lubed inside and out. Bonnie playfully clenched onto Connie’s probing finger. Applying a coating of lube onto her throbbing shaft Connie began inserting herself into Bonnie. Bonnie was as tight as she had been hoping for.

Grabbing the bag she had placed it the lean-to under Bonnie’s butt gave Connie the fucking angle that she wanted. Bonnie reached back and helped guide Connie’s cock to the opening of her virgin ass. Bonnie anxiously tried to stick it in by herself. She had never been the ‘receiver’ before. Connie’s cock was soon buried half way in Bonnie’s ass. “Wrap your legs around my waist”, Connie instructed. Bonnie did. Connie kept stroking Bonnie’s dick as she slowly pumped in and out of Bonnie’s tight virgin rectum. Bonnie’s prostrate was Connie’s target.

Without being asked Bonnie began involuntary subtle upward thrusts of passion that created deeper penetration. Connie was taking her time when Bonnie began increasing her tempo and brought them both to a glorious climax after about ten minutes of rutting. Connie caught Bonnie’s warm orgasmic spurts in the hand that was jacking Bonnie off.

With Bonnie watching Connie sensuously sucked one of her fingers clean of Bonnie’s sperm. Smiling at Bonnie she extended a sperm coated finger to Bonnie. “Have you ever tasted yourself before?” Connie asked. Bonnie pulled Connie’s hand closer and sucked Connie’s fingers clean one at a time performing a slow ‘finger job’ on each wet digit. Bonnie had licked half of her remaining boy juice off of Connie’s palm when Connie brought the remainder to her lips and slurped her palm clean.

Bonnie released her fuck grip of Connie’s waist and dropped her legs. “Whew, that was a beautiful thing,” Connie gasped. “I am so glad to have been your first. Thanks for a great ride.”

It was only then that Connie fully slid out. Bonnie was softly crying. Connie leaned forward and softly kissed Bonnie’s eyelids and gently rubbed her butt cheek. “Did I hurt you honey?” Connie asked. “No”, Bonnie replied. “It’s just I never thought it would be so intense. I’ve never been fucked before. I’ve never milked a man’s penis with my ass before. I was always the one on top.” Connie smiled affectionately and told Bonnie, “It was intense? Wait until we do this again and use the ribbed condoms.” Bonnie’s eyes widened as she envisioned what Connie was suggesting. Connie pulled her bag from underneath Bonnie and laid it to the side.

Lying on their backs and holding hands they let things settle down. It was great to just relax in a forest environment. After a few minutes Bonnie nudged Connie. “I feel like I’m leaking. What do I do? I’ve never leaked before.” Connie chuckled and told her to raise her hips a bit. Connie slid a couple sheets of paper towel under her ass. “Ok, you can relax awhile until the paper gets too wet. If you want to stop the leaking you know what has to be done, right?” Bonnie nodded yes. “Ok, just let me know when.” Bonnie meekly said “When.”

Retrieving a tampon from her bag Connie was kind enough to lube it prior to insertion. “Roll over, get on your knees, bend over and spread your cheeks apart.” Connie commanded. The tampon slid in smoothly. Connie gave the tell tale string a gentle tug. Grabbing Bonnie’s hand she guided her hand to the dangling string. “Here, give it a tug. You need to know where to find it and you need to know what sort of pressure it takes to remove your little friend. Otherwise you’ll think it’s just going to pop out when you least expect it and you’ll walk around without the confidence you need to use one of these.” Bonnie did as instructed.
They used baby wipes, paper towels and some of the water that Connie had brought from the stream to clean themselves as best they could. The cleaning materials were tossed into the nearby fire pit.

Bonnie said, “You know, seeing you standing there in black tights, with ribbons in your hair and made up like a princess was the nicest thing I’ve seen in a long while. The thought and effort you took in building us a pine needle mattress is impressive.” Bonnie hugged her and kissed her softly on her ear lobe. “Don’t go anywhere. I’ll be right back.” Connie chuckled as she watched Bonnie waddle to their tent with the tampon string dangling from her tight butt. In less than thirty seconds she was waddling back.

Bonnie produced a small white box and handed it to Connie. “Here’s a gift I bought for you the day after our class reunion. I wasn’t sure how to get them to you at a good time. There will never be a better time than now.”

Connie opened the box and revealed a pair of three inch gold hoop ear rings. “Oh, my god! They’re beautiful. Thank you. I love them!” She immediately began removing her studs. Her new hoops were soon dangling from her ears and the studs were in the box. Connie hugged and passionately kissed Bonnie several times. “How can I show my appreciation for your thoughtfulness?” Bonnie hugged her tightly and whispered into her ear, “Before we leave I want you to fuck me again… using a ribbed condom.” Connie softly laughed and replied “Hey sailor, what are you doing tonight?” Bonnie laughed.

About 5 PM

The day was fading and Bonnie suggested they put some clothes on. Soon they were clothed as they were two hours before. The only two exceptions were that Connie opted to not wear her tights (unless it got cooler). Connie had quite easily convinced Bonnie to wear a spare pair of her panties. “For old times’ sake.”

Evening dinner was the two deli sandwiches they had brought up from Jensen’s. Quick, easy and filling. As they were eating Bonnie said, “I have a few questions, Connie. I saw condoms in your knapsack. So why did you let me ride you bare back and squirt into you? I am not complaining. In fact it felt better than orgasmic for me.”

Connie thought for a moment before speaking. “I knew you had to have seen my condoms when you got me a tampon. You saw them, right? So the question really becomes why did you allow me to crème your prostate just now when you knew full well that there was an alternative to the fucking I gave you? For my part I let you cum in me because it made me feel sexily naughty. I can’t remember the last time I was that horny.”

Bonnie absorbed Connie’s comments and took her time before replying. “I did it because it made me feel like you and I are one person… skin to skin. And I was curious if I could feel you cum. I could. It felt warm. That was a very special sensation.” The couple held hands and smiled as they lay reflecting on recent events.

About 7 PM

Having given in to their pent up lust over the last two days the couple settled into a more traditional and less sexually active camping trip. They each took a water bag and walked to the stream to stock up on water making idle chatter as they walked. They made a second trip and transferred the water into every spare canteen, pot and container they had.

Bonnie built a fire and Connie made them tea using the propane stove. They spent the rest of the evening roasting marshmallows, staring at the stars and catching up on the last four years. They allowed the fire to burn down to embers. Bonnie doused the fire and they two retreated to their tent. After a few good night pleasantries they drifted off to sleep.

Day 3

About 6:30 AM

Connie was first up. Quietly slipping on a cute green A-line floral mini dress that she had brought she then pulled on her leg warmers. Reaching for fresh panties Connie hesitated and decided it would be a ‘no panty’ day. Returning her tap pants to her bag Connie left the tent wearing her white sandals with the gold trim. The cool air on her crotch felt good; very freeing. She started a morning campfire and set about warming some wash water on the propane burner stove. When the water was warm enough Connie filled a bowl with water. She set the water bowl on a nearby stump where she had already placed a disposable razor, a small bottle of Dr. Bronner's Organic Peppermint Liquid Soap, her hair brush, mascara and mirror.

Wanting to look pretty for Bonnie she quickly mixed up soap lather and shaved her face smooth. She passed on taking care of her legs and armpits; that could wait for later. Rinsing her face she tossed out the water and patted her face dry. Next she brushed her hair and created an off center high pony tail. She used a fluffy green scrunchie that matched her green dress. It was a style she had seen in a magazine; the dress looked like a sexy Girl Scout uniform. After an application of lipstick, her home made blush and mascara she was ready for the day. She was also ready for Bonnie.

The coffee had just finished when Connie heard the zipper of their tent. Bonnie stepped out and stretched. She was wearing denim shorts, sleeping shirt and flip flops. Seeing Connie she offered her a “Good morning lover” greeting. “You sure look cute for being out in the wilderness. Nice dress… I’m a bit envious.” Flashing a foxy smile Connie replied “Good morning honey buns. I hope you can walk OK today after our love session. Sure hope you aren’t lame.” They laughed.

Connie poured her a cup of coffee and motioned her to a log near the fire. Bonnie made a joke of walking bow legged. It brought out a giggle in Connie. Coming within range Connie planted a big morning kiss on her lips. Bonnie gave her a hug. Connie made them a nourishing freeze dried breakfast of scrambled eggs and hash browns. A light breeze rustled the pines.

Bonnie was sitting on large stump near the fire pit. Connie was returning from the tent where she had removed her leg warmers. With her purse in hand she took a seat next to Bonnie. Bonnie greeted her with a kiss to her cheek and again complimented her on the green floral mini dress. Connie began with, “There were times in high school when you would be the one anxious to wear a dress like this. You made a pretty girl when you wanted to. Remember?” Bonnie nodded in agreement.

Connie continued, “You were the one that bought a special padded push up bra two weeks before our pageant so you could have a hint of cleavage! And then, a week after the pageant, you bought a second one in a satin royal blue. Damn, you looked hot!” Bonnie nodded again. “So why don’t I see you trying to get back in touch with the girly side we both know you have? You have more options than lipstick and panties.” Connie rubbed Bonnie’s inner thigh.

Bonnie pulled Connie into a hug, kissed her softly on the lips and explained, “The military almost killed my femme side. Four years of boot camp and being in the Navy will do that to a girl. You’ve heard about the ‘Don’t ask, Don’t Tell’ policy? There’s also an unspoken ‘Don’t get caught or life will be hell’ that’s a very strict part of their policy. This morning when I saw you in your green dress I envied the freedom you have in expressing your femme side. Those puffy shoulders are perfectly feminine on you and the length shows off you pretty legs.” It sounded as of if Bonnie might cry.

Connie cuddled with Bonnie and tried to soothe her. “Babe, you aren’t in the military anymore. Be who you want to be. Let the inner Bonnie out. Be as femme as you want when you want. Butch it up when you have to. You have options now. Agreed?” Bonnie nodded in agreement. “Would you let me try some cosmetics and things on you out here in the wilderness in our own secret meadow?” Bonnie laughed and said, “Sure do your worst, baby.”

About 10 AM

Handing Bonnie her Copper Rose she said, “Do your lips… they need some color.” Ratting around in her purse Connie pulled out a bottle of Raven Red Maroon nail polish and began painting Bonnie’s toe nails. “We’re lucky. The polish sort of matches our lipstick” Connie said. Bobby softly repeated “Our lipstick… like it was in high school.” While the first coat of polish was drying Connie brought out the white jewelry box that held her gold ear studs. Standing in front of Bonnie Connie inserted a stud in each of her ears. Connie stopped what she was doing and said “The studs went in too easy. What’s going on?” Bonnie blushed.

“The evening of the reunion I found an old pair of pearl studs and forced my holes back open. I slept in them. I did the same every night until we began our trip.” In a perky voice Connie said, “Way to go girl... that’s a good start.” Connie sat down and applied another coat of red to Bonnie’s toes. “Hold still and let your toes dry.” Producing a delicate gold chain anklet Connie hooked it on Bonnie’s left ankle. “This looks nice on you and will remind you to enjoy your femme side. I hope it also reminds you of us.”

Bonnie’s hair in a pixie shag. Looks good… femininely athletic.

Connie stood and took back her lipstick. She put a one inch streak of lip color on Bonnie’s cheeks and effectively blended it in to a healthy looking blush. “Don’t move,” Connie admonished. Connie gave Bonnie’s eyelashes a double coat of her black mascara. “Damn, sure wish I had my eyelash curler.” Again Connie said, “Don’t move.” Bonnie patiently let Connie pluck and shape her eyebrows. “Hey, don’t go crazy I need to look semi normal when we get back to the real world.” “Don’t worry sweet cheeks; I’m just making things tidy.” Connie then did a quick tease to Bobbie’s pixie shag to give more fluff to her pixie shag blonde hair. Stepping back to check her project Connie smiled. As a finishing touch Connie repeated her dark charcoal eye shadow on Bonnie’s eyelids.

Stepping back Connie told Bonnie to remove her t-shirt and hop off the stump. Connie began cuffing Bonnie’s shorts until it appeared that Bonnie was wearing girly short shorts with a 5 inch seam. The total look was impressive considering what Connie had to work with; femininely athletic. Handing Bonnie her mirror she ordered Bonnie to take a look at herself. Slowly moving the mirror around it was apparent that Bonnie was impressed with the outcome. She twisted her ear studs. “Wow!” is all she said.

“We still have things we need to do but we have all day to do it and no one around to say we shouldn’t… just like our love making. We should finish doing our nails and if we wanted we have all we need to shave our legs. In fact there are several things we could shave if we wanted.” Bonnie held her fingers to Connie’s lips and said “Shhhh…” She hugged Connie tightly and said “Thank you babe for doing this. You’ll never know how important this is to me. It’s therapeutic.” They kissed.

Bonnie commented about how clever Connie was and how they could start a trail side spa for cross dressing back packers. They had good laughs about the possibilities. Bonnie paused a moment and said “You’ve worked wonders on me and I’m extremely pleased but I’m wondering why you had me remove my t-shirt?” Connie looked at Bonnie mischievously and said, “I had ulterior motives.” She moved closer and then began sucking and tonguing Bonnie’s left nipple. Using her thumb and forefinger Connie fingered and tweaked Bonnie’s right nipple. It too became quickly rigid like a pencil eraser!

Taken by surprise Bonnie gave out a low moan of pleasure. Connie continued with tongue teasing and sucking Bonnie’s flat breasts alternating from one nipple to the other. Her lipstick prints marked her progress. Reaching deep into Bonnie’s shorts Connie lovingly caressed Bonnie’s penis and cockhead until a liberal amount of pre-cum was achieved. After coating her thumb and forefinger Connie withdrew her hands from Bonnie’s pants and licked her fingers clean. It was a beautiful thing.

About 11:30 AM

Being near their pine needle nest that Connie had built, Bonnie backed Connie onto the edge of their ground tarp. Connie unbuckled Bonnie’s shorts and Bonnie kicked free of them. Bonnie was wearing the pretty panties that Connie had loaned her. Upon seeing the panties Connie began stroking and rubbing Bonnie’s penis while asking Bonnie, “Doesn’t this feel so good baby, so slick, so horny…?” Bonnie pulled Connie down onto the cushioned tarp and then she pulled Connie’s panties down. Connie’s prick was firmly at the ready. It too was dripping pre cum.

Connie pulled Bonnie’s panties down and shifted her full attention to Bonnie’s naked penis. Tonguing the head of Bonnie’s dick she sucked it into her warm and waiting mouth. Connie left lip prints and lipstick rings all up and down it. Leaning back Bonnie let Connie continue. Bonnie gently inserted her fingers into Connie three inch hoop ear rings and used them to gently move Connie’s head to where she wanted her on her dick. Connie hesitated a moment and with Bonnie’s cock still bulging in one cheek she looked her in the eye’s with a questioning expression. Bonnie answered the unasked question “I learned this in the Navy.” Connie resumed what she loved to do.

Bonnie reluctantly asked for a break in their love making. Holding up one of the ribbed condoms Bonnie announced, “I really want to experience what these condoms feel like.” Tearing open the condom wrapper she eagerly rolled the rubber down Connie’s rigged shaft. Forming her lips into a classic “O” Connie made sure there were no wrinkles in the condom by making a few runs up and down Bonnie’s shaft. After giving Connie’s cock a few dick hardening sucks she assumed the doggie position and said, “Fuck me. Fuck me deep.” Connie didn’t wait to be asked twice.

Lubricating her latex covered shaft Connie shuffled into position and placed her cockhead at Bonnie’s waiting sphincter. Bonnie reached back and inserted Connie partially into her. Connie considerately leaned forward and let gravity slowly slide her deeper into Bonnie’s recently discovered boy pussy. Bonnie extended her butt backwards in an effort to be more quickly and fully filled. Bonnie emitted a kitten like mew of pleasure. The condom ribs made a pleasurable difference.

The couple humped and fucked for a long while. As their climax approached Connie dug her toes into the tarp and thrust her cock as deep inside Bonnie as she possibly could. Connie ground and gyrated her penis deep into Bonnie’s rectum, arched her back, held Bonnie’s hips tightly and, at maximum possible penetration, she ejaculated with multiple squirts. After a couple more powerful waves of sperm Connie relaxed for a moment.

Still holding tight and firm in Bonnie’s rectum, Connie whispered, “Now clench my penis with your butt and hold it; feel me drag out of you.” Bonnie did as she was instructed. With Bonnie’s firm sphincter holding tight around her penis Connie slowly withdrew her penis by three inches. Bonnie let out a low moan of pleasure. Connie told Bonnie to relax. “Ok, clench me and hold my cock tight”. While Bonnie clenched again Connie slowly thrust and withdrew herself into Bonnie’s virginal tightness twice more. “Milk me!” Connie pleaded.

Connie slowly withdrew until only two inches of her cock remained in Bonnie’s body. Her cockhead was being gripped. The friction was good for both of them. “Relax baby doll. Take a deep breath, we’re almost done”, Connie said. Connie took a breath, slapped Bonnie very hard on her bare ass and loudly commanded, “Milk me, milk me!” By spontaneous reflex Bonnie immediately clenched down on Connie’s dick. Connie emitted a final and delightful penile squirt and began to go limp.

Connie’s expert ‘wrap around’ stroking of Bonnie’s penis while she had been fucking Bonnie left a large ‘Bonnie’ puddle on a well placed towel. Connie eventually pulled completely out of Bonnie butt and fell over, exhausted, onto her back. So did Bonnie. They were both breathing heavily.

“What a fantastic day” Bonnie stated. “Damn fantastic” Connie agreed. “Making sweet forbidden love out in the open; it can’t get any better. You bring an entirely new meaning to the term ‘milk man’.” They kissed.

Thirty minutes later Bonnie was still basking in a post orgasm glow and Connie was reapplying her lipstick. “You are truly a devious and erotic vixen; no panties and a nipple sucker. What a lucky girl I am.” Bonnie said. Connie smiled at Bonnie’s reference to himself in the feminine form.

About 1 PM

Bonnie had made lunch which consisted of chicken noodle soup and jerky. A bottle of lemon flavored water washed it all down. Afterwards Connie retreated to the tent for a nap.

About 2:30 PM

Unzipping the tent Connie stepped out and looked for Bonnie. She was not nearby. Bonnie was sitting in the sun on a stump near the trail that leads to the stream. Connie walked quietly towards her. Bonnie was obviously very engrossed with whatever she was doing. Holding still Connie saw that Bonnie had a bowl of water on the stump she was sitting on. It took a minute for Connie to comprehend; Bonnie was shaving her legs! Not wanting Bonnie to nick her legs Connie made her presence known by walking heavily.

“How are you doing, babes… need some help with that mow job?” They both laughed. “Just finishing but thanks for the offer.” Reaching Bonnie Connie said, “You have been a busy girl while I napped. I see you finished polishing your nails. Your hands look prettier now.” “Yes”, Bonnie said, “I borrowed your nail file and shaped my nails a little.”

Bonnie tossed the biodegradable soapy water into a bush and patted her legs dry. Bonnie ran her hand over her freshly shaved legs. She broke into a big smile and said “They feel like high school all over again. Thanks again for the anklet.” Connie bent over and kissed her on the cheek. “I see you brushed your hair into a cute pixie style. It looks very nice. And you switched out my gold studs for your pearl studs. The pearls are a prettier femme look for you. It’s all very nice. I’m happy you’re rediscovering your girly side. ”

“Did you shave your arm pits too?” Connie asked. Bonnie’s face became serious looking. “No. I’m not sure that I should; maybe when we get home. That whole military thing is messing with my head. I’m not ready to be so open with my femme side yet. Maybe I never will be. I need to be subtle.”

Next – (final) Chapter 3: Time to leave

(Remember that authors like comments. Thank you.)

UPDATE & FYI:

A character, Stacy, is introduced in the last part of the the next installment of this story that blossomed into several Stacy stories.

Who is Stacy?

Stacy’s first appearance was in the last few pages of High School Reunion: Bromance on Pacific Crest Trail – Chapter 3 of 3 where she was working as a very cute waitress in a small mountain town. Stacy was such an interesting character that she deserved her own story called Pretty Stacy. That story necessitated Pretty Stacy: Beginnings to explain how Stacy evolved to being Pretty Stacy; it shows her becoming empowered and confident. She is referenced in “Girls” for the Summer Club next. Which brings us to Stacy’s most recent story (“Girls” for the Summer Club 2 – A sister’s revenge).

Previously

Connie bent over and kissed Bonnie on the cheek. “I see you brushed your hair into a cute pixie style. It looks very nice. And you switched out my gold studs for your pearl studs. The pearls are a prettier femme look for you. It’s all very nice. I’m happy you’re rediscovering your girly side. Welcome back.”

“That whole military thing is messing with my head. I’m not ready to be so open with my femme side yet. Maybe I never will be. I need to be subtle.”

Time to leave

Bonnie stood up and hugged Connie and kissed her cheek. “I’ve been doing a lot of thinking about our time here. There have been so many feelings; so many desires are being resurrected. The sex I’ve experienced with you has been fantastic. You’ve brought ‘Bonnie’ out of her shell where she’s been dormant for so long. I’ve finally been able to let go some of the uptight military mind-set I’ve been subject to for four years. I just need some time. And I’ve found that I need you.”

Pausing to catch her breath Bonnie continued, “Rather than stay here the full week I think it would be best if we returned home early. I need to resolve things within my head and I definitely need to go clothes shopping. Let’s get back to camp and try to figure things out.”

About 4 PM

Connie began making hot water for tea and Bonnie sat on her favorite stump. Connie soon joined her and they sipped their tea together and enjoyed their secluded meadow. Sliding closer to Connie Bonnie shook the bottle of nail polish. Picking up one of Connie’s hands Bonnie began nonchalantly painting her bare fingernails. “You keep your nails shaped nicely. They look pretty.” While busy with her project Bonnie began speaking. “I need to get back early so I can psyche myself up and do some shopping. I can’t be as public with my femme side as you are. It will be our secret shared by close friends or when we go hiking.”

While Connie was blowing her nails dry Bonnie picked up her other hand and continued painting fingernails. “I’m just a run of the mill cross dresser that doesn’t want a lot of attention concerning my femme leanings. For me cross dressing is more of a hobby, for you it’s a way of life; a lifestyle, an attitude.”

Connie replied, “Don’t kid yourself honey… it’s definitely more than a hobby with you… shaving your legs proved that, whether or not you want to admit it. Welcome to the male sorority.” She continued, “I wasn’t sure how receptive you’d be to reverting back to your girly ways. You are very receptive. That’s why I left a three pack of panties on your back pack. You proved you will wear them. I hope you like the styles.” Bonnie said ‘thank you’ and then, “I don’t want to be ‘outed’ and embarrassed. I’ll need to focus on keeping my hands off you.”

Connie gave Bonnie an affectionate hug and said, “Well said. What you said makes sense. There is one thing you forgot to mention: you like to fuck… frequently. It’s something that you do extremely well. I doubt you can give that up entirely. If you need to store your new femme clothes, or place to try them on, or if you get lonely, I’ll give you a key to my apartment. Most importantly I’ll respect your secret until you tell me otherwise.”

While the two sat on the stump drinking tea and waiting for Connie’s nails to dry Bonnie absent mindedly applied another coat to her own nails. Looking over Connie giggled. “What’s so funny, Constance”, asked Bonnie. “Oh, a funny thought just popped into my head. Remind me when we get back to the trail head tomorrow and I’ll tell you. I’m sure you’ll get a kick out of it then.”

Connie offered Bonnie her leg warmers or tights if her legs felt too cool so soon after having shaved her legs. It had been years since Bonnie had smooth legs and freshly shaved legs always feel cold for the first day or two until the sensation wears off. “Just let me know.”

With their nails now dry they took a leisurely walk past the stream and down to where Bonnie thought there were trout. The view of the valley floor was impressive as was the view of the top of Baden-Powell. After awhile they turned to go back to camp. “That trout is going to have to wait until our next visit.”

About 7 PM

Back at camp they started a fire and turned on their propane mini stove. A package of freeze dried beef stroganoff was quickly ready and quickly eaten. All they had to do was relax and wait for morning. And then Connie began to get amorous. Her and Bonnie were kissing and enjoying each other when Connie reached into her purse and pulled out two ribbed condoms. Handing one to Bonnie Connie climbed under their lean to and onto their pine needle bed and said, “It’s our last night so let’s put these to good use; and I’m going to milk you dry.” Bonnie quickly joined Connie.

About 9 PM

Fully spent the two lay on their backs holding hands and basked in their post orgasmic bliss. Bonnie finally commented, “Those ribbed condoms sure make for an interesting sensation. They are like rumble strips for your ass. My butt is still tingling.” Connie commented, “I think a slow backstroke feels the best if you’re on the bottom.” The two killed the fire and went to their tent.

Day 4

Connie and Bonnie stayed in bed a little longer savoring the time they had left in their mountain retreat. Bonnie exited the tent first and quickly had a fire burning. When the coffee was ready she called Connie. “Rise and shine sunshine,” she said. By the time Connie got to the campfire her coffee was waiting on a stump. They ate a small breakfast as they were looking forward to a real meal in town.

Working at a steady pace they soon had their tent packed and the tarps folded. The last thing they did was to remove the tarp from their pine needle day bed. Bonnie untied the wilted flowers from the awning support sticks and tossed them aside. Reluctantly they scattered the pine needles that had been their mattress. They leaned their backpacks against a tree and fully cleaned their campsite. A single bag of trash would be carried back to a trash dumpster. It was only after washing off yesterday’s makeup that they took a break.

About 9 AM

Pulling her brush, mirror, mascara, scrunchies and lipstick from her purse Connie took care of last minute business. She brushed her hair and a single pony tail appeared. She wore it high and perky. Using her mirror she colored her lips and flicked her gold hoops. For the hike back to the trailhead Connie opted for her denim romper, a dark blue sports bra and white short sleeved cotton shirt with the shirt tails tied in the front. She cuffed her shirt sleeves for a bit more of a girly flair. Ankle high hiking boots with socks cuffed just above the boot and oversized sunglasses completed her look. Her cross shoulder purse hung from her shoulder.

Bonnie was wearing 501s, Connie’s panties, khaki REI sport shirt, boots, socks and a wide brimmed safari sun hat that hid her pearl studs. Her hairstyle helped hide her ear studs. Bonnie was also wearing the gold anklet that nobody would see. Her outfit was not too femme in any way. Unlike Connie she had personal demons and fears that needed to be resolved before daring to overtly display her girly side.

Connie offered Bonnie use of her lipstick. She was about to take it when she hesitated and said, “No thanks. I need to start being more discreet about being Bonnie.” She hiked up towards the outcropping that would take them back to the main trail. Connie followed.

Reaching the trail fork they both stopped and turned for a last look at their private Eden. “It’s been a fabulous few days.” She hugged Connie and gave her a kiss. “Yes, baby doll it’s been fucking perfect.” She chuckled at her lame joke and followed Bonnie.

About 11 AM

They hiked in silence for the most part except for brief comments about the beauty that is the Pacific Crest Trail and the best place to buy lingerie and women’s clothes. Forever 21, Kohl’s and Marshall’s were mentioned prominently. They also vowed to bring more baby wipes and paper towels the next time.

They were almost to the trail head parking lot when a group of four guys came their way. Bonnie and Connie stepped off the trail so the group could get by. The guys stopped to exchange basic trail pleasantries. “How’s the weather been? Any bears? Any fresh water springs? Do you know of any nice places to spend the night?” The men told them they had started at Big Bear Lake, 125 miles ago and were hiking through to the Mammoth Lakes part of the PCT, another 540 miles to the north, where they would meet friends.

Bonnie informed them: No bears, no springs, designated campsites about three hours up the trail. Don’t veer off the trail, good luck and safe travels. Putting the cap back on their canteen the guys pressed on.

As they were moving on Connie and Bonnie heard them comment, “The cute one was pretty quite. She’s fortunate to have someone so pretty to share her tent. The nights can get very cool.” Bonnie and Connie had both heard the guy’s comments. Bonnie playfully patted Connie on the butt and said “I’m damn fortunate. If they only knew how true that is. And we kept each other warm. Heck I think that we were blazing a few times!” “Why did they refer to me as a fortunate ‘she’?” Bonnie asked.

About 12:30 PM

Reaching the trail head and the SUV Bonnie helped Connie off with her backpack. They loaded everything except for Connie’s purse into the back hatch of Bonnie’s SUV. While Bonnie was disposing of their trash Connie opened the passenger door and placed her open purse on the seat. Retrieving her brush and another Scrunchie Connie gave herself the two high on the head ponytails that Bonnie had done for her back in camp.

Bonnie unlocked her door and got in the car. Connie slid into the passenger seat and flipped open the makeup mirror. After putting a few strokes of mascara on her eye lashes Connie freshened her lipstick and gave herself some of her home made blush on her cheeks. She restored the items to her purse. Looking over at Bonnie, who was watching her intently, she held out her lipstick for her. Bonnie shook her head in the ‘no thanks’ motion. “I need to be on the down low” she said.

“I’m amazed that you are looking so girly for the ride home. Those boys on the trail sure appreciated your cuteness and that was before you did the dual pony tail and mascara. You’re damn courageous.” Bonnie leaned over and gave Connie a quick kiss and said, “Thanks again for a great time. I hope we do it again soon.”

Connie smiled and replied “I’ve gotten to the point that sometimes it just doesn’t matter. I’m not trying to impress anyone and anyone we do meet we’ll never see again. I just hope they like my hair.”
Bonnie started the car and let it warm up before putting it in gear. “We need to stop at the ranger station and let them know were safe and are leaving early. It’ll just take a few minutes.” She put the car in gear and pulled onto the road.

Pulling into the ranger station parking area Bonnie turned off the car and set the brake. Just as she was about to open the door Connie grabbed her arm and said, “Hold up tiger. What’s the hurry? I just want to clarify a few things, ok?” She had a sly smile. Bonnie nodded and said, “We have all day. What’s on your mind, baby doll?”

Connie began; “Let me get this straight. You do not want to flaunt your femininity, right? You want to be cautious and not call attention to your girly self, right? And do you remember last night when you were painting our nails that I giggled and you wanted to know what I found was so funny, right? And you also recall that I said I’d tell you today, right?” Bonnie shook her ahead in the affirmative and replied, “Yes, I remember all of that. So what was so darn funny yesterday?”

Connie began laughing and said “Look at your fingernails, Missy. Your painted nails are about to give you away… what are you going to do with your ol’ femme self now? You sure don’t look very subtle to me.” Glancing at her nails it was obvious that Bonnie was so comfortable in having painted nails that she had forgotten to remove her polish.

“Oh, my god, that would have been pretty difficult to explain away! Pass me your remover please.” Connie began laughing harder. “Well baby doll, that’s the funnier part; we don’t have any remover with us!” Bonnie visibly turned pale. Her mind was racing. Connie was still laughing.

“And that isn’t the funniest part; check your ears. Old Missy, ‘I’m-so-subtle, I’m-so-worried, I’m-so- careful’, left her freaking pearl studs in! You’re going to give ditzy blondes a bad reputation.” Connie’s laughter got louder. Bonnie grasped her lobes and sank back in the car seat in bewilderment. She went limp in her seat and stared vacantly out the windshield.

“And those hikers… what the hell must they have thought?” Connie stopped laughing long enough to reassure her girlfriend. “Your wide brimmed hat and your shaggy hair cut must have kept them from noticing your ears. When you were conversing with them I noticed your fingers were curled as if you were in a military parade so they saw nothing. The most they could have seen were your thumb nails. Besides they were too busy checking me out to pay you that much attention. I saw them staring at my bra. Maybe they thought we were two lesbians!”

“You knew I had screwed up and you let me walk down the trail wearing earrings and nail polish?” Still laughing Connie stopped long enough to say, “Hell, yes! That’s what makes it even funnier. You sure are discreet… not!” Starting softly Bonnie began softly laughing until she too was laughing out loud. Connie was wiping away tears of laughter. Gradually their laughing stopped. “Ok, now what do we do?’ Bonnie asked.

Connie patted her leg in reassurance, reached into the glove box and brought out a pair of thin leather driving gloves. “Put these on, go in, check out and don’t forget to return to the car. Then we’ll think about stopping to eat somewhere. I’m hungry and a fresh cheese burger would be greatly received. Be sure to thank the ranger for the hot chocolate.” Bonnie exhaled in relief and exited the car.

It was about five minutes before Bonnie returned. She opened the car door, took off the gloves and started the engine. “What took you so long?” Connie queried. “The ranger was asking about my pretty girlfriend with the perky ponytails… if we had fun, were there any bear sign, etc. He was also prying for information on how many times we ‘did it’ in the tent. To tease him I said that you were a real slut and that we ‘did it’ eight times but that only twice was in our tent.” They both started laughing as they got back on the highway. Bonnie gripped the steering wheel; her pretty maroon talons contrasting with the black steering wheel.

About 1:30 PM

“Let’s stop for a real meal at Beth's Grizzly Café. It’s coming up in about ten minutes. I’ll pay if we go in with our matching painted nails in full view… no driving gloves. Let’s see how bold you think you are kissy face, you’ll never see these people again. Let’s give the locals something to talk about.” Bonnie gripped the wheel tighter and got quiet. Connie started softly singing the Bonnie Raitt** song ‘Something To Talk About’:

Ooh, ooh, ooh,
People are talkin', talkin' 'bout people,
I hear them whisper, you won't believe it.
They think we're lovers kept under cover,
I just ignore it but they keep sayin' we...
Laugh just a little too loud,
Stand just a little too close,
We stare just a little too long.
Maybe they're seein', somethin' we don't darlin'.

Let's give 'em somethin' to talk about
(Somethin' to talk about)

Connie had resigned herself to a basic drive through hamburger down by Highway 138 and the Interstate when Beth's Grizzly Café came into view. Taking a deep breath Bonnie pulled into the café parking lot and parked. She shut off the engine, set the brake. Connie looked over to see what Bonnie was going to do. ‘Is he woman enough to do this?’ Connie thought. They sat in the car for a few minutes while Bonnie contemplated her options. “Are you up to doing this, baby?” “I think so”, Bonnie softy replied.

“Hold a minute while I get ready” Connie said. She used the rear-view mirror again to apply lipstick and then put on a down camping vest. “I’m ready” she said. Bonnie looked at her and said “What’s with the vest?” Connie smiled and proudly said, “By wearing the vest they won’t know that I don’t have big tits. It’s all image, illusion and attitude. They’ll see my romper, my nails, my lipstick, my sports bra and my two beautiful pony tails and assume ‘girl’.” Bonnie nodded her head in agreement. “When I look at you I see woman.” She leaned over and gave Connie a tender kiss. Connie returned the show of affection with a firm kiss to Bonnie’s lips in an effort to transfer some of her lip color to Bonnie’s lips.

Taking another deep breath Bonnie and Connie exited the car. Connie wore her cross body purse into the café. Without incident they were quickly seated in a comfortable booth; their matching Raven Red Maroon nail polish glistened. Bonnie took off her sun hat and ran her fingers through her shaggy blonde hair, exposing her forgotten pearl studs. Connie shifted her sunglasses to on top of her head.

In a short while their waitress came to the table. “Hello, my name is Stacy. What would you like ladies like to drink?” Stacy was definitely cute. She was dressed in the mountain café waitress image of the Alps. She wore a blue and white gingham waitress outfit with short puffed sleeved shoulders. Her uniform included a white lace apron, a snug bustier and an attractively short dress that ended about four inches above her knee; a starched crinoline petticoat with ruffled hem gave her dress the girly flair she sought. White tights, black ballet shoes and cute chandelier earrings completed her uniform. She definitely looked pretty.

Connie ordered a Pepsi. Pausing from reading the menu Bonnie ordered an Arnold Palmer. The waitress shifted her gaze from Connie to Bonnie and back again.

Before leaving to get their beverages Stacy said, “You two make a cute couple. It’s not often that a couple has matching nail polish and lipstick. It’s darling.” Bonnie was momentarily taken aback about the reference to them having matching lipstick but replied, “We just got back from four days of camping. We got bored and decided to give each other a manicure.”

Turning to Connie Stacy said, “I love your perky twin pony tails. They are so adorable. Who did it? Did you go to a salon?” Connie grinned and gestured with a maroon thumb nail towards Bonnie and said, “She did it.” The waitress smiled and was about to leave when Bonnie spoke up; “Our toe nails match too.” The three of them laughed and the waitress went for their beverages.

Connie turned to Bonnie and said, “See that wasn’t so bad. In fact it was kind of fun and she noticed that our lipstick matched.” Bonnie smiled and repeated “It wasn’t so bad after all.”

Stacy returned and set their drinks down. She was just about to write down their food order when she hesitated. Bonnie and Connie looked up. Stacy said, “I was thinking that I may have seen you two before… maybe a few years ago. You look familiar. Did you or your girlfriend attend South Hills High?” Bonnie nudged Connie under the table and in a mocking tone said, “Nobody will recognize us. Right.”

Connie explained that they had graduated five years ago. Stacy perked up and said, “I was a year behind you. In fact you girls won the Womanless Beauty Pageant didn’t you? You’re Connie and Bonnie! Sorry but I’m not sure who is Connie and who is Bonnie. You inspired me with your courage to let your girly side be known. It was very brave of you. It was because of you that I entered the Womanless Pageant the next year. And I won! Look at me now! It took me a year to work up the courage to go public with Stacy. I can’t wait to tell my friends that I met you both.”

Stacy looked at Bonnie and said, “Your pearl studs are cute but the chandelier earrings you wore when you won the Pageant were prettier. Studs must be better for hiking.” Immediately Bonnie quickly touched her studs. “Damn, I thought I took them out,” Bonnie exclaimed. Connie chuckled.

“Your chandelier earrings and the way you carried yourselves really inspired me. It was nice to see others that liked dressing up like me. I thought I might be the only one.” Stacy nervously toyed with her own earrings.

Putting down her menu Connie said, “I’ll have a cheese burger with onions and a side of potato salad.” “Make that two,” Bonnie echoed. Prior to placing their order Stacy said, “I live in town on Blue Bird Lane. If you wouldn’t mind another hiker I’d like to go hiking with you girls sometime. I have my own boots.” Stacy left with their food order.

Connie was still giggling. “You sure are discreet, aren’t you?” Bonnie just shook her head and rubbed her ears. “I was wondering why, when we sat down, she asked ‘what would the two ladies like’. And you let me leave my studs in. Thanks.”

Stacy brought their food. Bonnie said, “I’ve been trying to remember you from high school but I’m drawing a blank. I usually would remember someone as attractive as you.” Stacy leaned forward and in a soft whisper informed Connie and Bonnie, “I used to be known as John Miller. I played junior varsity basketball.”

Bonnie continued, “Stacy you sure are a cutie. It’s not easy to look as feminine as you. How do you do it so well on a full time basis?” Stacy blushed. “Your petticoat looks yummy. It accents your girly curves; very nice look.” Bonnie felt the edge of Stacy’s petticoat. “Damn, that’s hot! I think I’m going to pick one up for special occasions. It looks so… sexy.” Connie gently kicked Bonnie’s leg.

Before speaking Stacy looked cautiously around. Speaking in a low whisper Stacy said, “If you’re wondering if I had myself ‘snipped’ in order to look feminine, the answer is no. I love my appendage too much; I wouldn’t want to miss out on all the pleasure it gives me… or others.” Taking a quick look around she continued, “I exercise and I do take a few ‘vitamins’ to keep myself fit.” She thrust her chest out for emphasis. “Have you girls been ‘snipped’?” Stacy asked.

Connie and Bonnie laughed. Bonnie said, “No, we agree with you. Why get rid of a major source of pleasure?” Stacy smiled and replied, “Whatever you’re doing keep it up. You girls are very pretty.” She turned and left them in peace.

After Stacy left Connie sternly said: “Stop hitting on the hired help! Yes, she looks like 120 pounds of fun but you came to this party with me. Next you’ll be telling her how virile you are or what a large puddle you make.”

Noticing that the girls were finished eating Stacy brought them their check and a single slice of whip crème topped strawberry pie with two forks. “The pie is on the house, just don’t tell my boss. Did I mention that I live in town on Blue Bird Lane? I’m off work in 45 minutes. Maybe you would like to shower off the trail dust? My walk-in shower will easily hold us all. I have a few petticoats I think you’d both love to see… or try on. Everyone should have some rustle in their bustle.” Stacy slipped Bonnie a café business card with her phone number and address on the back. Her hand lingered a bit on Bonnie’s hand. Stacy sort of sashayed over to another customer, flourishing her petticoats as an enticement to the girl’s.

Connie rubbed Bonnie’s knee and said, “Baby cakes, I think you’ve got an admirer.” “Correction”, Bobbie replied, “I think WE have a fan club.”

The end?

Or is it a new beginning? Should Bonnie and Connie go camping again? Should Stacy go with them? Should Bonnie and Connie go to Stacy’s or drive home? Is Stacy 120 pounds of fun?

PS 4/25/2019

Stacy, the waitress character mentioned here, spawned a NEW story called “Pretty Stacy”. Bonnie and Connie accept Stacy’s invitation to stop by her house. This spin off Stacy story is ‘work place safe’. Give it a read.

There is a "Pretty Stacy: Beginnings" story. Stacy is an interesting character. But HOW and WHY did John Miller become Pretty Stacy?

-- ("Pretty Stacy: Beginnings" was posted August 18, 2019) a 16K story --

(Remember authors like comments. Thank you.)

Post Script: For readers that may be curious about the Pacific Crest Trail or Mt. Baden-Powell I’ve left links that explains and shows much of the beauty of the south end of the PCT. Readers that are curious about Connie’s twin pony tails a photo of the look is included below.

Pacific Crest Trail is 2,653 miles - 2,650 miles (4,265 kilometers) from Mexico to Canada through California, Oregon, and Washington.

Southern California: Traversing 700 miles of deserts and mountain ranges, the Pacific Crest Trail is striking and easily accessible in Southern California. To the west of Mount Baden-Powell and the Angeles Crest National Scenic Byway.

Mt Baden Powell trail: Very good link. Photos, maps, info.

https://images.search.yahoo.com/search/images;_ylt=AwrNJkmAOQRcqjAATkpXNyoA;_ylu=X3oDMTEyOWY2NDlsBGNvbG8DYmYxBHBvcwMxBHZ0aWQDQjU4NTlfMQRzZWMDc2M-?p=mt+baden+powell+trail&fr=mcasa

Hiking Mt Baden-Powell - Mt. Baden-Powell (9,399′) — one of the highest mountains in the San Gabriel mountains. The stunning 360° views made those 40 switchbacks worth climbing.

https://socalhiker.net/hiking-mt-baden-powell/

San Gabriel Mountains , San Gabriel Mountains National Monument - 8-mile trek up the north face of one of the tallest mountains in the San Gabriel’s. Good info.

https://modernhiker.com/hike/hiking-mount-baden-powell/

Originally known as North Baldy, Mt. Baden-Powell was named in 1931 after Lord Robert Stevenson Smyth Baden-Powell, the founder of the Boy Scout movement. It is one of the most popular peaks in the San Gabriel mountains, with stunning views of the Mojave desert, Mount Baldy, and the Los Angeles. The annual Angeles Crest 100 Mile Endurance Run passes over the peak in the fall.

https://www.summitpost.org/baden-powell/150664

Here's Connie's hairstyle as they hiked out

Who is Stacy? Stacy has become my favorite character. I wish I knew a Stacy when I was younger.

Stacy’s first appearance was in the last few pages of High School Reunion: Bromance on Pacific Crest Trail – Chapter 3 of 3 where she was working as a very cute waitress in a small mountain town. Stacy was such an interesting character that she deserved her own story called Pretty Stacy. That story necessitated Pretty Stacy: Beginnings to explain how Stacy evolved to being Pretty Stacy; it shows her becoming empowered and confident. She is referenced in “Girls” for the Summer Club next. Which brings us to Stacy’s most recent story (“Girls” for the Summer Club 2 – A sister’s revenge).

Chapter 2 - Indeterminate sentence - Jenny & Stacie

(This story is ADULT fiction. Comments would be appreciated. Thank you.)

Previously

“Adjourn to breakfast and meet back here in an hour. Take note that from this point forward any time you need to pee you MUST sit down. To not do so could put you on ward C. As you noticed there will be NO excuses. Enjoy your breakfast and special vitamins. Report back here in 60 minutes for a late breakfast. We have many things that you need to know.”

Day 16 - Breakfast

It was a late breakfast, as promised, but it was adequate. It was filling but very institutional tasting. Maybe some of the flavor was the ‘special’ seasonings. Beside every plate was a small paper cup with three pills we were to take. ‘Vitamins’ we were told; ‘vitamins’ that would make us want to rut. Each recruit was watched as we swallowed them. If you refused the pills there would be no food.

I studied the other recruits as they ate and noticed that all, including myself, had developed an itching in their tits and we were subconsciously scratching and rubbing the affected area. I’m sure it was caused by the program to give us a B cup size tits in a short period of time.

Unnoticed by us was that after our meals we all noticeably mellowed out and were less apprehensive; more open to suggestions and instructions. The marvels of pharmaceuticals are amazing.

As I ate I chatted a bit with Stacie but also tried to engage myself with some of the other recruits. Jackie, at the end of the table, in particular piqued my interest. She appeared to be in good shape, had a friendly smile and Paul Newman blue eyes. Her blond hair wig made it even better. ‘I need to introduce myself’ I thought.

The general conversation at the lunch table was everyone’s fears and concerns of what the program was going to involve. Our concerns were somewhat abated by what was in the food. The removal of Jewel and Mary also was brought up. Their departure had gotten our attention. It was soon time to report back to the dayroom. We cleaned the table and left for the meeting area.

The Matron explains

“Thank you for being on time. We have a lot to go over in a short period of time. As you know The Program involves both physical and mental changes to you all. Your blatant disregard for women will be gone before you are allowed to leave The Nest. There will be lots of classes and training on topics ranging from how women should be respected, to learning make-up skills, the proper way to dress and behave. Your male mannerisms and voice modulation will be scrutinized and modified as needed. Each of you will have the chance to be the giver and the receiver. Street terms call it being the ‘top’ or the ‘bottom’. One of your TV channels in your rooms covers this in graphic detail. As the hormones take effect these activities can be very pleasurable. It involves trust. Again none of you have an STD.”

“Each room has a TV. The only channels available consist of make-up techniques; love making and hygiene techniques, how to conduct your selves as women in terms of walking, talking, posture, mannerisms, intimacy and other related subjects. We are monitoring you. Your use of the various channels will be duly noted as will the number of times you access a channel and how long you watch a program. It’s crucial for your realize that you must watch them all and in their entirety.”

“Today’s inspection was very mild. Inspections will become increasingly more complex. Today you were not required to wear nylons. You will gradually be introduced to panty hose and eventually to garter belts and stockings. Your make-up today was very basic. Little by little you’ll be required to increase your femininity. Tomorrow panty hose and a bit of eye shadow are mandatory.”

You will also be required to become intimate, first with your roommate, and then with the other recruits. Your room doors remain unlocked, unless the staff locks them, you are free to cum and go. You have already kissed and held hands. And we know, by way of our monitoring systems, some of you have taken steps in that direction. Everyone must comply or you will join Jewel and Mary.”

“In a moment you will be taken to get your ears pierced. It’s quickly done with a special earring piercing gun. Medium sized gold starter posts today. As time goes by your earrings will be changed to note your progress. Some may earn double or even triple piercings. Read The Rules. After your ears are done you are to return to your rooms to get better adjusted to your roommate and the program. I suggest you start watching your TV. Your required sleepwear is already placed on your beds.”

“After your ears are pierced you will no longer be referred to as ‘recruits’. You will be referred to as ‘ladies’ or ‘girls’ which better reflects your future status. Dinner will be at 6 PM sharp. Do NOT be late and be sure to bring your hand bags."

Twenty minutes later we were slowly walking to our rooms fingering and rotating our new ear studs. Joan mentioned to me: “It didn’t look like they used the piercing gun on you.” With a sideways glance I replied “No, my ears were already pierced. Their studs slid in easily.” We talked quietly among ourselves as we walked. You could hear dorm room doors closing.

Flashback 2 – our final month

Stacie wakes Jenny

I had my eyes closed and was relaxing on my bed. Stacie entered the room placing her purse, and a large envelope, on the nightstand. I emerged from my trip down memory lane. “Are you alright, Jenny? You seem a little spaced out.” Stacie said. “I’m fine Stacie. I can’t believe a new State ID takes so freaking long! I was also thinking about our first week here. It seems so long ago.” Stacie walked over and sat on my bed. She smiled down at me and slowly stroked my head in an effort to comfort me. Bending over Stacie kissed me gently on my lips. She smelled nice. “It’s almost over” Stacie whispered.

I smiled back and pulled Stacie down for a longer and more passionate kiss. “Mmm… that’s yummy. Did you get a new lipstick? It smells nice and tastes divine. You bring out desires in me you little vixen.” With a well practiced move I pulled Stacie down onto the bed and cuddled her close. She was wearing a blouse so it was easy for me to undo a couple buttons and gently cup and fondle Stacie’s breasts.

Stacie’s bra was a front closure and I easily popped it open exposing her aureola and nipples. Her nipples were rigid in lustful anticipation. I pulled Stacie closer and licked one nipple. Stacie moaned like I knew she would. Moving even closer I began nursing on Stacie’s other tit, swirling my tongue in slow circles. Stacie moaned a little louder and did a gentle, kitten like, squirmy move. I gave Stacie’s breast a final kiss, leaving a cute lipstick imprint. ‘That’s a beautiful sight’ I thought.

Staring Stacie in her eyes I smiled and ran my hand up Stacie’s skirt. The feel of her garter belt straps was a definite turn on for me. The feel of the top of Stacie’s nylon’s was even more erotic. All concerns and anxiety about my release date were gone. Sex is a good therapy.

Stacie was a willing player in this game and while I was soul kissing her Stacie’s hands found my crotch. “My, aren’t we naughty today. No gaff. I guess it’s my lucky day. Better yet it’s my licky day.” We both chuckled at her joke. Stacie rubbed the front of my dress exactly where and how I like it rubbed.

Giving Stacie another passionate kiss I broke away and sat up. “Wait a minute; I need to get this dress off before I accidentally hose it down. Unzip my dress you little slut.” Stacie quickly had it done. I stood up and stepped out of her my dress leaving it in a pile on the floor. She too was clad in garter belt, nylons, lacy panties and pretty balconette demi-bra. I asked Stacie to lift her legs a bit and I was able to easily pull off Stacie’s skirt. Stacie made a beautiful sight lying on the bed with just her garter belt, hose, panties and an open, unhooked, bra. Stacie’s smile and sultry eyes were inviting. Her eye shadow and mascara helped the image. She made me throb.

Grabbing a blanket from the foot of the bed I rejoined Stacie in bed and pulled the blanket over us. It was a matter of being cold and had nothing to do with the video and audio surveillance units. Heck, this type of behavior was not only encouraged by staff it was expected.

Resuming our passionate kissing our lust grew. Stacie inserted her hand into my panties and freed my engorged penis. Out of impish impulse Stacie’s, while grasping my shaft, used her thumb to spread my pre-seminal cum around and around my penis. ‘God, she is really wet’ Stacie thought. It was me that was moaning now. Using her thumb and forefinger, Stacie firmly circled my cock head, making sure to gather my leakage. Stacie circled finger slowly spread the pre-cum down my shaft with a slow, downward, slide. She made it all the way down my shaft and had pre-cum to spare. “God you are really hot… and really wet” said Stacie. My eyes rolled back and I began to kiss Stacie even more passionately.

I moved my attention back to Stacie’s tits, alternating kissing, sucking and licking them both. Her hard nipples were a favorite target and I carefully nibbled them from time to time. I was also busy with my hand and was lovingly caressing Stacie’s shaft. Stacie’s panties were below her knees by now. I grabbed Stacie’s entire shaft and began the classic, but slow, jacking off movement. Copying me, Stacie also used her thumb to help increase the flow of my pre-cum by circling my cock head and pee hole. My cock head and crown were not ignored. They glistened with slick, wet, pre-seminal fluid. Our panting became quicker.

I took hold of Stacie’s perky breasts and slid down her body towards Stacie’s very rigid penis. I had just licked my lips and was getting ready to fellate her when suddenly Stacie said “Stop!” She reached over to the night stand and grabbed her new lipstick. “Here put this on first. Please.” I took the tube, flipped off the top and with seasoned practice extended the lip lube with just my thumb and forefinger. Locking eyes with Stacie I didn’t blink as I applied a liberal coat of her dark red cosmetic to my lips. I pressed my lips together and licked them for flavor.

I just as expertly retracted the lipstick tossed it onto the bed. Extending myself up to Stacie’s face I kissed her on the lips. We tongued each other and our passions became more intense. I broke off the kissing, and tenderly stroked Stacie’s hair and cheek. Giving Stacie a sly grin I threw off the blanket and began moving downwards toward my engorged target. On purpose she made it twitch. Our sex-musk permeated the room. Our hearts were pounding in anticipation. Neither of our hands had missed a stroke.

Reaching the object of my lust I maintained a firm but gentle grip on Stacie’s cock with one hand. Lifting Stacie’s penis just enough, I tickled her penis tip with my tongue, and then planted a long and sucking kiss on Stacie’s cock head leaving a souvenir in the shape of a lipstick mark. Stacie twitched again. I loved to make Stacie twitch! It felt good. It made me feel alive!

Opening my mouth to form an ‘O’, I sucked Stacie’s cock head about an inch into my mouth. Pressing my lips tightly on Stacie’s cock head, I blotted my lipstick on her rod, leaving a dark red ring. There was another, more noticeable twitch from Stacie and I thought I detected a hint of an upward thrust. I tried to smile but that’s hard to do with a cock in your mouth. Holding Stacie’s dick in place with just my firm lips I swirled and flicked my tongue in all the right places.

Maintaining a firm lip grip I slowly suctioned and licked my way down Stacie’s well lubricated shaft. Her cock head hit the back of my throat. I made a swallowing move with the back walls of my throat that squeezed Stacie’s cock head. I felt yet another twitch, a throb, from Stacie. My tongue was busy licking, swirling and caressing Stacie’s rod the entire length.

Reversing direction, and using my tongue in creative ways, I found the sizeable vein that I knew was there. I traced it with my tongue. Reaching the tip of Stacie’s cock there was a noticeable popping sound as I broke suction and my mouth pulled free. I licked my lips clean of Stacie and smiled. “Let’s see if the audio monitors heard that” I announced to Stacie. “My god that was nice! Any complaints?” I whispered.

I was about to make another run down Stacie’s rigid and throbbing pole but Stacie stopped me. Looking directly at me she leaned over the bed and retrieved her tube of lipstick. Twisting it open Stacie followed my lead and applied a thick coat of red to her own lips. “You can’t have all the fun, Jenny. It’s my turn.” In the blink of an eye Stacie quickly assumed the classic 69 position and grabbed my shaft. Foregoing any formalities Stacie quickly engulfed my cock, expertly guiding it into her mouth. In a heartbeat Stacie had suctioned her way halfway down my shaft swirling her tongue to increase my sensations. She made a point to press a red lip ring on my shaft. She slurped back upward and quietly popped free to inspect her red lip print on my cock. With no hesitation she immediately dove back making a point to make it to the base of my penis. She made sure to place another red trophy ring. I was glad I had shaved myself smooth today.

As I tried to pull her off my dick Stacie slowly and reluctantly sucked and slid her way up and off of my appendage. She made sure she had left two red rings. Stacie loved to ‘mark territory’. I grabbed Stacie and we kissed, making a point of spreading our pre-seminal cum on each other’s lips. I pushed Stacie slightly backwards and said “If we’re going to do this let’s do it right” I picked up the lipstick, reapplied yet another coat of red and passed the tube back to Stacie. Stacie did the same. She retracted the lipstick and set it on the bed.

We looked at each other and smiled. Stacie spoke up and announced “Ok, let’s roll!.” We immediately assumed the 69 position and went back to passionately sucking each other’s cocks. No one was keeping time but after a pleasant amount of time we climaxed in unison. I could feel her multiple squirts and the flexing of her penis. I held still and let her throb. It was a beautiful thing. I tightened my lips and slowly milked the remnants of her seed as I slowly backed up and off her shaft. The popping sound of uncoupling was something I always try for. As a matter of habit neither of us swallowed right then. Fully satiated we rolled on to our backs and stared at the ceiling and enjoyed our post climax glow, allowing our pulses to slow. We waited a minute savoring each other’s flavor. Then we did a slow swallow while looking into each other’s eyes. Her look was angelic. I reached over and used a finger to remove a drop of ‘me’ from the corner of her mouth. Still staring at her I licked my finger clean. Her smiled widened.

We rolled over to face each other and shared a kiss of happiness. Stacie began to laugh and said “Boy, your lipstick is all messed up!” I grinned and replied “I’m glad to hear that. I sacrificed my lipstick for your pleasure.” “By the way, yours doesn’t look so perfect either. And I thank you for that” I replied.

“I still get a chuckle recalling how when you were picked up by the cops that you were wearing panties and I was wearing French cut panties!” We laughed, pulled the blanket up to our shoulders and assumed the normal ‘both heads on the pillow’ position and spooned in contentment.

Moving my earring out of her way Stacie gave me a loving kiss on the side of my neck. “I brought you something, darling” Stacie purred. Rising from the bed Stacie retrieved the envelope from the nightstand and handed it to me. Opening the envelope I found what appeared to be a letter and some papers. Removing the papers I reached in again and pulled out my brand new, shiny, State ID card! The look of surprise on my face made Stacie laugh. Grasping the ID to my breast I looked over to Stacie and began to softly cry. They were tears of happiness.

Stacie came over and sat next to me. She wiped a tear off my cheek. Wrapping her arm around me, Stacie pulled me into a warm hug. She pulled me tighter and whispered, “Don’t worry, we’ll be fine. We got through it together, just like you said we would so long ago.” Turning to face each other we had another passionate, prolonged kiss. Breaking free I said “I can taste you on me… and I like it.”

Stacie smiled and relaxed her hug. “We ALL got our IDs just a little while ago! Jackie and Rose are sitting in the day room waiting for us. Pull some clothes on and let’s go share the moment. I would have told you sooner but ‘something’ popped up.” We both giggled like school girls.

Back to the present

There was a lunch and a dinner. Nothing to write home about… even if we were allowed to write. There were more indoctrination speeches and long explanation about the importance of following the Program. There were sessions on makeup application and removal, female voice training, proper expected girly mannerisms, how to sit, how to cross your legs, etc. It made for a very long day.

Day 17

Inspection 2

We “girls” were awake 30 minutes earlier than the day before. We removed our silky chemises that had been given us. After a quick shower, and a dusting of the after shower powder, we donned and combed our wigs and put on our panties and bras. We jiggled our silicon enhancements into place. The jiggling helped ease the constant itching. I noticed that Stacie was using my wash rag trick from yesterday to enhance her bust. So did the video monitor above.

The two new requirements for today were pantyhose and eye shadow. Both of these mandates were no problem for me. I had already done my eye shadow and I had my silky pantyhose on. A delicate anklet was on my left foot.

With practiced ease I showed Stacie how to roll down and scrunch up each nylon leg, insert your foot (one at a time) and then roll them up each leg. I emphasized the need to smooth each nylon leg out (in order to eliminate wrinkles) by grasping your ankle with BOTH hands and then sliding your hands up each leg. The hose we wore was of the control top variety and it was immediately noticeable that they could help minimize crotch bumps.

I noticed that Stacie was missing her anklet. “Pass me your anklet and I’ll hook you up” I instructed. Stacie handed me her anklet and I knelt to put it on. After hooking the clasp, and while still on my knees, I looked up and was eye level with Stacie’s crotch. There seemed to be a bulge in the middle of Stacie’s skirt. I reached over and gave her bulge a slow, but firm stroke, using one finger, from the bottom of her bulge to the top. The bulge seemed to be about six inches in length. “Where did THIS come from?” I asked.

Looking down at me, Stacie obviously blushed, and said “I couldn’t help it. I was looking how cute you look, how nice you smell and when you were touching my ankle it just happened… I’m sorry!” I stood up and looked at Stacie. I gently hugged Stacie and then pulled her closer in a friendlier hug. “Don’t worry about that, baby doll. In fact I’m flattered.” I whispered into Stacie’s ear. I planted a soothing kiss on Stacie’s lips and gave a comforting rub to her left butt and stepped back. Looking down at Stacie’s skirt I was sure the bulge was a bit bigger now. “We may need to get you some stronger control top hose or maybe a gaff.”

“With all the hormones, vitamins and blockers they’ve been feeding us it’s no wonder that we have itchy breasts, are hornier than hell and are a bit moody. It’s probably what they want” I said while glancing up to one of the video monitors.

I had already done my eye shadow and motioned Stacie to come sit on my vanity bench for some help. “This is easy. You pick a color suited for the occasion or color of your eyes and simply apply it to your closed eye lid. I dip my little finger into the color I want and just gently spread it over my lid. You can mix colors and create a unique shade. Some girls like to use a small sponge applicator or a special brush. Now you try it.” Stacie hesitated a bit while trying to process how Jenny was so knowledgeable on eye shadow application. And gaffs?

Stacie decided on a light blue color and elected to use the small sponge applicator. It went on easily and Stacie gave a sigh of relief. “That was easier than I thought it would be.” Jenny smiled and ran her hand gently on Stacie’s cheek. “You did fine and your eyes look… pretty” I replied.

Stacie started to stand up but I said “Hold on a minute I want to show you another trick that we’re going to have to know sooner or later.” I picked up a tube of eyeliner, unscrewed the cap and used a built in tiny brush to carefully outline each of her eyes. “Note that I went a bit beyond the outer corner of my eye and ended with a slightly upward line extension at the end. You need to wait a minute to let it setup and dry or you risk smudges. We will do yours tomorrow.” Stacie starred in amazement at my eyes. Yes, they did look more feminine. ‘WHY does she know these things’ Stacie wondered? Stacie stroked my cheek, flashed a friendly smile and said “Thanks for the tip.”

We both stood up and went to the full length mirror for a self inspection before leaving for the day room. Everything seemed to be correct. On impulse I opened the top button of my blouse. My necklace (and my cleavage) stood out in a better way. Satisfied with our look we grabbed our purses and gave ourselves a last minute spray of perfume.

Stacie opened the door and as I stepped into the hallway she gave me a playful pat on my butt. I quickly turned to look and we both giggled at the gesture.

Fabulous Foursome

Stacie, Jackie, Rose and I had met and became friends as we all went through the two weeks of processing. We all looked very different now. We all were attractive, very feminine looking and we smelled ‘pretty’. Our entire group was a bevy of beauties (some more than others).

Almost immediately I saw Jackie coming down the hall towards us. In an attempt at humor I stepped in front of Jackie and extended my hand in a lady like fashion. Jackie stopped and did the demur feminine handshake. “Hello, I’m Jenny and this is my roommate Stacie. I meant to say hello yesterday but things got a bit hectic. How are you doing today?” Briefly taken aback Jackie quickly recovered and played along “I’m doing OK I guess, considering the circumstances. Are you ready for today?” Jackie absent mindlessly gave her left breast a bit of a scratching.

I flashed a smile and replied “We’re doing ok too. I wanted to tell you how nice your ear studs look with your hairstyle. Your blue eyes are quite stunning.” ‘Oh God’ Jenny thought. ‘I hope she doesn’t think I’m being to forward.’ Sensing a bit of awkwardness Stacie cleared her throat and said “We better be going or we’ll be joining Jewel and Mary in ward C.” The gaggle of girls giggled and started walking to where we needed to be.

We were the second group of novice women to arrive and we immediately took a seat at what was a basic cafeteria bench style table. I made a point of sitting between Stacie and Jackie. I leaned slightly towards Jackie and took a sniff of her perfume. ‘Very subtle and tropical… I need to ask what she’s wearing’. The remaining girls arrived and took the remaining places. It was obvious that others were experiencing the chest itching too. There were some discrete tittie rubs and some not so discrete outright breast scratching going on.

There was idle talk among us. Some of us girls were commenting on the TV videos. Rose asked if anyone else had seen the video on intimacy yet. Everyone shook their heads in the negative. “You got to watch it! It is so detailed and graphic. It’s a complete ‘how to’ guide on just about anything you can imagine. It gave me a raging hard on!” Beth spoke up and admitted that she too had also watched it. “It’s a triple X and leaves nothing to the imagination! I swear I could smell the love making! It made me horny.” Our group all laughed and agreed to make viewing it a priority. Tracie volunteered that she had watched the video on makeup and hygiene and that she had found it helpful. “At least I know what things are called and how to use them. I had never douched before.” There was another round of nervous laughter.

We were just starting to talk about our new feelings, emotions and itching we were experiencing and were wondering to what degree the hormones and vitamins had to do with it. “Last night I just started crying for no reason. I had a hard time stopping.” Jackie said. Just then the Matron and Miss Diane walked in. Martha was there too as were two other “girls”. The room went silent.

Day 17 - pre-breakfast briefing

“Good morning girls we hope you had a restful night as we have another busy day ahead of us. You all have met Miss Diane and Martha. The other ladies are Cindy to my left and Rhonda is to my right. They are here to help and assist. We will do our basic inspection again, you will all go for another round of injections, and your newly pierced ears will be checked as you can’t earn the other earrings until your starter earrings have healed. Immediately after breakfast you will be given another inoculation. You will also have your eyebrows shaped and be taught how to maintain the look we expect of all our ladies.”

“Following this you will be introduced to a few new experiences and tactile sensations that should be new to all of you. This is where your roommate is needed. Be gentle with them and they will return the favor. It will make all the experiences easier. If you need additional help we have staff members at the ready. This process requires your complete cooperation. If you relax and take deep breaths it will be easier for you. For some the process will outright enjoyable.”

The Order of the Earrings

“Many of you have wondered what the different colors of earrings and number of earring piercings mean. Although these meanings can be found in The Rules book that you were given and on your room’s TVs. A copy will be provided to you shortly. “

“In conclusion it seems I need to explain more about our monitoring program. You are all constantly being monitored including video and audio. You have been told about this before. Notes are being taken and progress reports are being written about you on a daily basis. Your progress is being tracked and your release date is determined by these reports. Staff members are responsible for this and you will never be told which staffer is your monitor.”

“Let me give you a few examples of our thoroughness. Just minutes ago only two of you admitted to watching our video on intimacy and hygiene. The correct number is five. You all have been told to sit when you pee. Beth ‘forgot’ twice and Rose has failed to comply four times. I have other examples of infractions but will not bore you with them now.”

“On a lighter note it is time for breakfast. Go eat. And ladies, you may want to have a serious discussion with your roommate, and maybe others, about how you will get through this day. You have sixty minutes. Be sure to take your vitamins.”

We remained seated as the sober reality of what Matron had told us sank in. There was a lot of rubber necking as we tried to size up each other. We began standing up and shuffling towards breakfast. There was muted, yet agitated, conversations going on all at the same time.

Breakfast Day 17

Breakfast, like yesterday, was very basic; scrambled eggs, potatoes, sausage links, fruit and a variety of beverages. It all had an odd after taste. And of course there were the paper cup of vitamins. Conversation was diverse yet subdued. All too quickly breakfast ended and the girls started making their way back to the dayroom. Jackie stopped as I was standing up. “Thanks for talking with me earlier. I really appreciated.” Jackie gave me a quick hug and said “Good luck today.” And then she left.

Back in the dayroom

We were all seated and waiting for Matron and Martha. We didn’t have to wait long. Martha approached our group and announced, “Listen up ladies, here’s the plan. You can see they we’ve set up what appears to look like four barber chairs. In a moment you will go there and have a seat. A beautician will shape your eyebrows into a more feminine manner. We expect you to keep them exactly like we shape them today. The process typically involves eyebrows being plucked and shaped with tweezers. Sometimes a waxing process is used. Everyone has a personal tweezers in their vanity. Watch and learn. If you can’t do it right, ask your roommate to help. As is our custom we have instructional videos on the TVs in your room.”

“Your earring piercings will be checked for infection. Your beautician will remove your studs, inspect the holes, dip the studs in alcohol and reinsert them. We expect to upgrade you all to the two inch gold hoops within the next three to four days. Before leaving the chair our medic will administer another dose of hormones. You can expect to be a little moody, a bit emotional and you may find yourself crying for no apparent reason. These side effects are normal and will cease in a couple weeks. These “side effects” are what all women go through and so will you. Your program requires you to learn what women experience. With four techs working the entire process should take 30 to 45 minutes. When you are done you are to come back to this table and await further instructions.”

Martha was right. Before 40 minutes had gone by we all were back at the table. Some were twisting their ear studs, casually scratching their evolving titties and carrying on subdued conversations. The main topic was how very feminine their new eyebrows looked. A few were reapplying lipstick. So did I.

I sought out Jackie and told her “You really look pretty. Your new brows look awesome”. “Thank you, Jenny. Yours are pretty too. I hope we can keep them looking nice. That plucking sort of hurt.” I agreed and replied “But now we have fewer to pluck!” Stacie chimed in with “Have you seen how fantastic Jackie’s brows look?” All of the ladies nodded their agreement.

Pre lunch purse inspection

Matron, Martha and Miss Diane came over to our table.

“Girls, we have a busy day but first we’re having a purse inspection. Everyone open their purse and dump the contents directly in front of you. As long as you have the basics mentioned on the first day you’ll be fine. Mascara, lipstick, blush and a hair brush.” Matron took a quick look down the table and was pleased that everyone was in compliance. “That’s great. Everyone did fine.”

“Miss Diane is passing out four more items that will be a ‘must have’ in your purse at all times. These new items are in a zip lock baggie being passed out to you now. The ‘must haves’ are a tube of personal lubricant, a makeup compact with a mirror and two Lite Days tampons. Also in your zip lock is a small 8 inch vibrator that’s only one inch in diameter. You’re to keep this in your personal vanity in your room. You will be using this device very soon. Ladies, repack your purses as I have more information about today’s activities.” A low gasp rose in unison from the table. Vibrators!?

“Here’s the drill. You are to pair off with your roommate. Put your hands palm down on the table and wait for my instructions. In general you will bend over and your roommate will lube and gently insert your vibrator into your rectum. You need to know in advance what to expect when you’re penetrated in the days and weeks to come. It will be inserted up to the 4 inch mark on the device. This will be done very slowly at first. There is no rush. The secret is to relax your sphincter. If you get lucky your roommate will find and touch your prostate gland. You will know if they found it because it feels so good that you will not be able to keep from smiling. Don’t be upset if it isn’t found today. You will have other opportunities on other occasions. Maybe, in your room, you can find it for yourself.”

“The insertion procedure will last only five minutes. During these five minutes your roomie will slide the phallus in and out of your rectum making sure to get to the 4 inch mark. At the end of 5 minutes the device will be removed and you’ll be given the opportunity to clean yourself up. You will also clean the vibrator. It’s yours so clean it well. You’ll be taking then back to your rooms. After a few moments of rest you will trade places and you’ll service your roommate. Do not be embarrassed if you involuntarily ejaculate on to the table. It’s a natural response and paper towels are cheap.” Nobody laughed at the Matrons attempt at humor.

“The girls on the hallway side of this table will be the first to receive. You will stand up, pull down your panties and panty hose, drop your skirt, bend over and keep your hands flat on the table and wait. Your roommate will pick up your vibrator and stand behind you. She will dip the tip of the vibrator in to a bowl of provided lube. The rest of your indoctrination will start when I give the command. At the five minute mark of my stop watch the device will be removed by your roomie and placed on a paper towel that will be in front of you. Again, it is your vibrator and you will clean it and put it in your purse until you get back to your rooms. Take a few minutes now to collect your thoughts. Take a few deep breaths. Those girls doing the insertion are free to rub your back or neck to help relax and soothe you. An occasional kiss has been found to be calming. Your initial response will be to clamp down on the device. Don’t do it this time. Relax. When engaged in a real sex act, with a real partner, feel free to clamp down on their penis. It is like a ‘milking’ motion that can be very enjoyable for your partner; grip, ungrip, grip again, clench, etc. Clamp and release then clamp and release again. You’ll figure it out as you learn what makes you feel good.”

“To assist you with a better understanding we’re passing out a diagram so you have an idea of where your target is for maximum satisfaction. Take a moment to review it before we proceed. Take this to your rooms and put in your notebook of rules. You may want to refer to it again. Your target area should include your prostate gland; this true if you’re have sex with a partner or if pleasuring yourself with a vibrator.”

“Everyone sit down for now and I’ll tell you when to start. If you can’t shove the dildo in deep enough, Martha, Miss Diane, Cindy or I WILL make it happen. We may not be as gentle as your roommate. Afterwards you will have time to relax and compose yourself. Lunch will follow.”

Our table went quite. You could see some of our faces become pale. Some of us started shaking. A few had tears running down their cheeks. Without an exception roommates reached across the table and gripped their roommate’s hands. You could hear the girls either begging their roomie to be gentle while others were promising their roomie that they would be gentle. Matron noticed that I was the most composed of the group. I was squeezing Stacie’s hands and whispering assurances to her. I gave Stacie a smile and told her “Take some deep breaths. Relax. Be calm. It will be over soon. I’ll be easy with you and then you get to be gentle with me, right?” I gave Stacie a wink and a final hand squeeze. The time was near.

Taking a look at her watch Matron announced “OK, first group stand up, pull your panties and panty hose below your knees and drop your skirt to your ankles, bend over, spread your legs and put your palms flat on the table. Roommates pick up the vibrator in front of your roommate and go stand behind her.” Matron waited until everyone was correctly in position.

“Roommates, using whichever is your dominate hand grab the vibrator and dip it in the bowl of lube as it’s passed around. Do not spare the lube. Dry spots hurt. Use your other hand to spread the lube evenly on the dildo… er, vibrator I mean. Using the hand without the vibrator step up to your roommate and spread her butt cheeks. Look and find her ‘rosebud’ and wait for my next command.” Looking around Matron saw that Cindy was stroking a frightened girl’s hair. Martha and Miss Diane were slowly pacing back and forth behind the receiving group that were bent over and were ready to jump in if needed.

Matron said “Get ready. See your target? I’ll start my stop watch when we begin. You ‘bottoms’, take a deep breath and exhale. Place your palms on the table. ‘Tops’, start the insertion NOW!” She clicked her stop watch. In unison the ‘tops’ began shoving the greased phallus into their roommates’ anus. “Slightly twist the vibrator back and forth like removing a wine cork and begin pushing. It spreads the lube and makes the penetration process easier.” She was right and soon everyone had full insertion. “Slide it in to the four inch mark and stop. You ‘bottom’ girls, try to relax. Try not to clamp down, don’t clench and do not ‘milk’. Exhale. Close your eyes if it helps.”

You could tell which pair was having it easier. Beth was rubbing Tracie’s shoulders, I had stepped enough to the side of Stacie that I could whisper in her ear and tenderly nuzzle on her ear lobe. I also planted a few kisses on her neck. It seemed to help. Stacie visibly un-tensed her shoulders and back, taking the plastic shaft like a pro. Miss Diane made a mental note to add this info to my file. ‘Stacie is lucky to have Jennie for a roommate’. At that moment Matron said “Begin the butt fucking now. Do not go deeper than the four inch mark. In and out. In and out. Try tilting it slightly upwards, then downwards; you might hit the magic spot. You have three more minutes to go. Increase the speed of your thrusting; try the wine cork technique. Twist it back and forth like your using a door knob; it increases the feeling. Pick up the tempo ladies.”

At the 3 ½ minute mark most of the faces of the ‘receivers’ were emotionless… except for Stacie. Stacie was beginning to smile and thrust backwards to meet my thrusting. With my free hand I gently grabbed her testicles and started caressing them. Stacie began panting and was clearly excited. She loudly moaned once, thrust backwards and immediately ejaculated half way across the table and shouted “Quicker, quicker, don’t stop. For god’s sake don’t stop”. I gladly accommodated her by thrusting more quickly, ‘turning the door knob’ and doing a little wiggle movement at the same time. She let loose with a couple more squirts.

“Stop!, time’s up. Remove the vibrators.” shouted the Matron. I did as instructed but removed it slower than normal making sure to continue ‘opening the wine bottle’. Stacie collapsed onto the table. Her eyes were closed and she was breathing heavily. “’That was a beautiful thing’ she thought. She felt hot and was horny as hell.

Stacie grabbed some paper towels from the table and quickly wiped her rear crevice as best she could. She took no time in pulling up her panties, panty hose and skirt. It was bit difficult as her penis was still semi rigid. Still breathing like a marathon runner she turned around and grabbed me around the neck. Stacie stood tall in order to kiss me on the lips. It was a lingering kiss of passion. “Oh, god! Thank you, thank you, and thank you. That was marvelous!” She kissed me again. Turning to face the bench she smoothed her skirt in a lady like fashion and sat down. The Matron, Miss Debbie and the other staff members made mental notes of Stacie’s enthusiasm.

Sitting on the bench Stacie caught her breath and began wiping up her sperm puddle from the table. Looking around the table Stacie began blushing and feeling embarrassed. “Oh, I am so VERY sorry. I really am embarrassed that I was so noisy… and so messy.” No one seemed to mind. Truth is some girls looked visibly disappointed at their experience. Her enthusiasm excited me. There was one other puddle on the table. The second puddle had cum from Jackie. It looked like it would be a few minutes before Jackie could pull her panties up and over her raging erection. Rose apparently had done her good.

“Take a short break and we’ll get on with the next session. You know the routine. Remember to clean YOUR vibrator and put it in your purse. There will be a pull string storage bag for each of you on your vanities when you return to your rooms. Keep in mind this unit is only ½ inch diameter, most men are at least two inches. Your future partners may be better endowed. As a side note, had you just been penetrated by a man or your roommate, this is when you’d insert one of your tampons to stop any leakage. You wouldn’t want to soil your clothes or your bed.”

We were chatting at the table as the initial fear of the unknown was gone. Many of us were asking Stacie and Jackie about their experience. Stacie was very animated as she spoke and was smiling broadly. There was some giggling as she recounted her experience. And then it was time for the second round of penetration preparation. My heart began to beat faster in anticipation.

The second session went quicker. Everyone knew what was expected. I was the first one to be ready to start. My panties, panty hose and skirt were pulled down further than suggested. I didn’t want anything to interfere with MY experience! I had already assumed the position while others were just getting into position. In short time roommates were standing behind their roommates. The vibrators were well lubed and ready to go.

Matron told us to get ready and then she held up the stop watch and shouted “Go!” The insertions went easier and everyone was on target. I reached backwards and helped Stacie place the device on my rose bud. Whispering over my shoulder I told Stacie “Make it good.” I helped make the initial inch of insertion. My butt fucking was going well. All around me it was a controlled frenzy with a hint of sex in the air.

Stacie was rubbing my shoulders and softly speaking encouragement to me. Out of impulse Stacie reached into my blouse and massaged and squeezed my tiny titties. She did something to a nipple that was electric. I moaned my appreciation and arched my back. I shifted left and right wanting to feel it all… to get a different feeling in my rectum. I was making an effort to have the vibrator meet my prostrate.

It seemed like only a couple minutes had gone by when Matron announce “Ninety seconds more ladies, finish strong!” Smiles were evident on several recipients and things were going well. I was already thrusting backward in a lusty attempt to increase my pleasure. My eyes were closed. I was making little grunting sounds as I thrust backwards and wiggled my butt. I was clenching and milking. I felt slutty and I wanted more. I was breathing rapidly. Twenty seconds later I thrust backwards, gripped the vibrator once and exploded. My semen made it completely across the table. I paused but a moment and continued my backward humping. It was obvious that I was clamping onto the vibrator and enjoying the feeling as it was being pulled outwards from my ass. “Times up! Pull them out and start cleaning up” Matron bellowed.

I didn’t move. My head was bent downward, my shoulders slumped and I was staring vacantly at the table top. My breathing was rapid and I was still panting. There were two other puddles of cum from the other girls on the table. Without looking up I asked hoarsely, “Will someone please toss me a towel?” Immediately three towels were thrown my way and as a group everyone began laughing. As I was cleaning myself Stacie bent down and helped pull my panties and pantyhose up and into place. Getting them over my penis felt so sexy to Stacie. Stacie gave my erection a caring caress. I pulled up my skirt with no help and turned around.

“Did I do OK? Did I hurt you?” Stacie anxiously asked. I paused but a moment and then grabbed Stacie in an ardent embrace. I gave Stacie a fevered kiss. There was no lack of passion as I used my tongue on Stacy. Breaking the embrace I said “Babe, you were great! You did fine. Thank you. I had no idea that it would feel so damn good!” Stacie noticed that a tear was slowly rolling down my cheek. Stacie leaned forward and kissed it away. We both smiled and held hands for a few moments prior to continuing with the session’s clean up.

Walking behind the group Miss Diane had been watching us all but Stacie and I, in particular, caught her attention. She liked what she saw. ‘It looks like Jenny could be a lot of fun. She sure milked that vibrator…clamped on it like a dog with a bone. I may have to give her my bone. It may be time to schedule a one on one evaluation. Damn I’m getting wet.’ she thought.

Matron began an announcement. “In general you all did well. At least you know what to expect. Most of you are experiencing feeling, emotions and desires that you’ve never felt before. Because of the hormones and vitamins you’ve been taking these feeling and sensation are normal. Embrace these feelings and desires. They are part of your reeducation program and it will lead to your eventual release. Your itching breasts are normal too and the itching will subside as your breasts grow. Most of you are already an A cup already. Enjoy your new breasts. Note how they bounce as you walk. Explore them. Rub your nipples. Ask your roommate to kiss or suck them. Your breasts can bring you and your roommate much pleasure.”

“You have asked about the meaning of the various earrings you’ve seen on the staff. I am passing out a copy that explains The Order of the Earrings. Read it. Remember it. You may want to keep a copy in your purse. For your convenience a copy is now posted in your bathrooms. As always you can find a copy on your in room TV. It’s a straight forward, easily understood, explanation of what your release is dependent on. It could help you set personal goals. Have a seat at the bench table and Martha will give you each a copy. Once you have read The Order of the Earrings you may return to your rooms. You have free time until lunch at 12:30 PM. Use your free time wisely. You have much to accomplish, requirements to be met and a lot of pleasure to experience. As a reminder do not fall behind on your mandated instructions. You may be called in for individual one-on-one counseling.”

As the staff members started to exit Miss Diane stopped and turned back to face the recently penetrated and deflowered girls. “Before you return to your rooms you are to remove your compact from your purse and reapply a fresh coat of lipstick. Get used to it. You are to do this after every meal, after every heavy episode of petting and kissing and especially after every blow job you give and as needed throughout your day. Do it now!... and then I’ll leave you be.”

We did as we were told. It was no big deal. Besides, most of us had begun to like the smell and taste of our lipstick. Some of us were also beginning to like the taste of our roommate’s lipstick as long as our roommate was wearing it. You could hear our compacts snap closed. We all went back to reading our copy of The Order of the Earrings; goals we had to meet.

Order of the Earrings

Advancement to another level requires a MINIMUM of 5 experiences from each category. You are encouraged to EXCEED the minimum. To attain release from The Program you must attain the Sapphire level, be a C cup or greater and constantly maintain a feminine appearance and demeanor.

Gold 2 inch hoops- a novice just beginning the requirements.

Pearl – Cum colored; signifies you have given 5 blow jobs minimum. You must swallow each time.**

Ruby – Red colored; signifies you have lost your Cherry and have received anal sex 5 time’s minimum. Your partner must cum in you for you to get credit. Use of condoms is not permitted**

Sapphire – Blue; signifies you have met all minimum requirements in every category. You must be a C cup or better and constantly maintain a feminine appearance and demeanor. You are eligible for release but are not guaranteed immediate release. Final determination is based on a final staff report.

Diamond - signifies you have met all requirements, are receptive to any type of sex and are fully committed to the Program and its goals. You constantly maintain a feminine appearance and demeanor. You must be a C cup or better but have decided to remain in The Nest.

Double ear piercing - wear any combination of gems, hoops or studs - has fulfilled all requirements in all categories and is receptive to any kind of ongoing sex. You must be B cup or better.

Triple ear piercing - wear any combination of gems, hoops, or studs - has fulfilled all requirements in all categories and is receptive to any kind of ongoing sex. You must be C cup or better. The only difference between double and triple piercings is that the wearer prefers to be the “bottom”.

Vibrator – All ladies in training MUST use their vibrator for self gratification that must end in ejaculation a minimum of seven times.

** If you are giving oral sex while receiving anal sex both parties get credit for the act(s) they are performing as long as there is ejaculation. The same is true for the reverse. Remember you are disease free and sperm does not taste bad. Condoms are NOT permitted.

(to be continued in Chapter 3)

Chapter 3 - Indeterminate sentence - Jenny & Stacie

(This story is ADULT fiction)

Previously

We did as we were told. It was no big deal. Besides, most of us had begun to like the smell and taste of our lipstick. Some of us were also beginning to like the taste of our roommate’s lipstick as long as our roommate was wearing it. And some had simply begun to like the taste of their roommate. You could hear our compacts snap closed. We all went back to reading our copy of The Order of the Earrings; goals we had to meet.

The Order of the Earrings

We were sitting at the dining table reading the Order of the Earrings that we had just been given. The goals that were expected of us were clearly laid out. Comments like “Wow! Really? They must be kidding”, “The sooner we start, the sooner we can be released” were heard. The audio monitors got it all. A few of us said nothing and a few just smiled.

Everyone stood and meandered to our rooms. Some of us were holding hands and some had their arm around a new friend or their roommate. Before reaching my room I asked Jackie, “Would you like some company later? Stacie and I have talked about getting to know some of the others better and after today we think we’re ready. I’m sure we could learn some things. Maybe practice some techniques?” I blushed and continued “Geeze, I hope I’m not being to forward.” My heart beat went up.

Jackie smiled and said “I’m flattered that you thought of us. I’m OK with it but I want to ask Rose first.” Jackie reached over and stroked my cheek. “If Rose isn’t receptive right now maybe I could visit you guys. I’ll let you know at lunch.” She looked over at Stacie and said “See you guys later.” Jackie continued to her room. Rose was just behind her.

I opened the door for Stacie. As soon as the door had closed we kicked off our heels, removed our anklets and rolled down our pantyhose. “Whew, am I glad to get those off” Stacie said. I nodded in agreement and said “I’m pretty sure that’s what they want us to feel; it’s part of our education program to experience and feel what women go through.” I removed my blouse and went to the restroom to wash my face. I left my panties and bra on. As I was splashing water on my face Stacie came up behind me and unsnapped my bra. I didn’t realize how big my tits had become until I saw them dangling down and swaying as I washed.

From behind Stacie reached around and gentle grabbed both of my tits at the same time. Stacie began using her thumbs and forefingers to circle my nipples. She gently rolled my nipples between her thumb and middle finger. Her soft touch, and her groin pressed against my panty clad ass, sent a strong tingle straight to my penis. My nipples were at full rigidity and stood out like pencil erasers. I didn’t want her to stop. Stacie cupped my breasts and “You know, I can definitely feel some real tits. Your nipples are responsive too. They’ve both obviously grown since we got here. You must be one of the B cup girls they were talking about… they may be almost a C. They feel marvelous.” Stacie stepped back.

I turned around and shrugged my shoulders and easily slipped out of my bra. I hung it on a towel rack. Facing Stacie, I cupped her tits, looked down and felt her nipples. I felt and watched her nipples stiffen. “You really think so?” I asked. Stacie leaned forward and kissed my right nipple. She sucked it into her mouth and began tonguing all around the nipple while making little flicking moves with her tongue. I felt another jolt go right where I wanted it. Stacie moved to my breast and repeated the process. I groaned, closed my eyes and leaned back so that the wash basin was holding me up. It felt REALLY sensuous. I felt my cock firming up and my panties beginning to tent.

I pulled Stacie to me, wrapped my arms around her and unhooked her bra. “Lift your arms” I said. In the blink of an eye Stacie’s bra joined my bra on the towel rack. I reciprocated the pleasures that Stacie had just given me, sucking first one tit and then the other. Running my tongue around and around Stacie’s nipple was making her pulse race. It also was making my penis grow. My dick was about to pop above my panties. Looking down I saw that Stacie was responding in the same way. I leaned into her and made our nipples touch. I grabbed one of my tits and drew nipple circles around her nipples with my nipple. I had never done that before. Whatever drugs they were feeding us had to account for our high lust levels. Nobody was complaining.

I reached over and grabbed Stacie’s thickening shaft and gave it a few strokes through her nylon panties. The head of Stacie’s penis was poking above her panties. I took the opportunity to use my thumb to spread her pre-seminal leakage around and around the head of her cock. It was very slippery and wet; just the way I was beginning to like cocks. It was Stacie’s turn to moan. I pulled our panties down letting our shafts spring free. She made a slight thrusting motion and her cock touched my cock. Stacie grabbed our cocks and held them touching, side by side. I could feel us throb. I could feel the heat. She stroked us both at the same time. She mentioned a novel sex act called ‘docking’ that she had found on our in-room TVs and how we should give it a try. She had watched the video several times and said it would be very 'different' and enjoyable for us both.

Based upon the video instructions Stacie was able to insert her cock-head into my foreskin, placing her cock-head along my skin covered shaft. She then pulled my foreskin over her cock! It appeared we shared a seamless penis. We slid our cock-heads slowly back and forth alongside each other’s shaft. We were one. It was truly electric. We were both oozing and breathing heavier. Stacie leaned forward and kissed me deeply while continuing to jack us both off at the same time. We could taste each other’s lipstick.

We ‘undocked’ and somehow Stacie got hold of somebody’s panties and began to slowly slide them up and down our dicks which were still side by side. She then started to lightly “buff” our dicks with the nylon panties; it was like she was slowly buffing shoes. It was a tickle of lust. I have never been that hard in my entire life! A point of no return was fast approaching. I wanted to prolong those sensations as long as I could.

Stacie grabbed me by the wrist and pulled me to her bed. We kissed again and Stacie pulled me down onto the bed. “I really want to thank you for the pleasure you gave me in the dayroom. It was fantastic” Stacie said. We kissed and stroked each other for just a bit and while kissing Stacie whispered into my mouth “Will you fuck me? Fuck me now? Like in the dayroom but use your dick. I want to feel you throb and cum deep inside me.” Stacie spread her legs and pulled me on top of her.

“Do me first and, if I’m able, I’ll do you, OK?” she pleaded. Her voice and her eyes conveyed her urgency. I thought a minute and said “Ok, let me get some lube.” I was reaching for my purse and Stacie stopped me. “No. No lube. I’ve got a better lube.” She flipped around on the bed and grabbed my stiff shaft. My cock was standing tall and proud. Stacie moved her grip to the top of my cock and gave me a few strokes, up and down my shaft, smearing pre-seminal wetness with each stroke. I groaned and laid back. Keeping eye contact with me Stacie pulled my cock head toward her mouth. She used her closed lips and tongue to further smear my pre-cum. She then made a slow lick down and up my shaft. She tickled my pee hole with her tongue tip.

I was quivering in anticipation. Shifting to a better position Stacie puckered her lips and sucked my shaft into her mouth as if was a big piece of spaghetti. She swirled her tongue making my shaft as wet as possible. The flow of pre-cum was increasing and Stacie took advantage and made several runs up and down my cock. Sensing that the time was right Stacie sucked and licked her way up my dick. There was an audible ‘pop’ as she broke suction. “There now, I think we’re lubed up. How do you want to take me?” Before I started I pulled myself over to Stacie’s lips and gave her a passionate kiss. I ran my tongue over Stacie’s lips. “I can taste myself… and I like it” I told her. She kissed me back and made sure to kiss me in a way that transferred more of my pre-cum onto her lips.

I said, “You read the chart. If you finish the blow job you get brownie points.” Stacie gave me an unmistakable glare and tersely replied “Fuck that chart! I want YOU to fuck me. Now! So how do you want me?” God, she was hot, horny, wet and wanton. “In the porn I’ve watched it’s good if you lie on your back and wrap your legs around me” I said. In a split second Stacie was on her back and was pulling me between her legs. I grabbed my well lubed cock and pressed it gently against Stacie’s sphincter. “Yeah, that’s the spot” Stacie panted. I pushed a little harder and got my penis about two inches beyond her initial anal muscle. Stacie reached down and grabbed my penis and tried to pull my cock in deeper. She succeeded. I took the hint and made another slow, steady, forward thrust.

I stopped at about four inches and then partially withdrew which garnered another glare from Stacie. With another forward thrust I was in the full length. I stopped and held still. In return Stacie made a clenching rectal movement and gripped my cock. It made me my rod throb, which is what I’m sure she was trying for. I couldn’t help but smile.

I began a rearward withdrawal movement; Stacie’s tight anal muscle felt so warm and good when she clenched. ‘No wonder they call it ‘milking’ I thought. Stacy relaxed; her rectal muscles and anus stretched and opened wider and I began a true butt fucking. It felt so right! I increased my tempo and Stacie raised her legs up a little higher and then she moaned as my cock rubbed against her prostrate. “Argh!! Damn you, go faster”. I obliged and soon we were rutting in a sex crazed frenzy. “Quick, grip me” I begged. Stacie made multiple rectal clenches on both my in and out strokes. Finally, for maximum feeling and depth, Stacie threw her legs over my shoulders and my cock went to places never visited before. My testicles’ were beating a rhythm on her butt.

I made a several forward thrusts and then held steady as far in as I could get. It felt like I could lift her off the bed and have her hanging from my dick. To get deeper I tried to push Stacie up the bed with my dick and then I erupted. Wave’s of cum squirted deep into my roommate’s bowels. There was a second and third ejaculation but I held firm, pressing forward and holding it. I had my toes dug into the bed for leverage. Stacie was sure she could feel my sperm. She made a few more rectal clenches and gave a loud yell and arched her back.

“There’s that feeling again, make it last! Do it, do it!” she pleaded. I made a few more rapid stabs into her. And then she collapsed. She flexed her sphincter muscles a couple of more time, which I greatly appreciated, and then laid still. Stacie was completely spent and satisfied. Her breathing was rapid like a sprinter; a broad smile of contentment on her face. “I could feel your warm sperm wash my rectum.”

We laid there, coupled together between her legs, and let our bliss subside. Stacie dropped her legs onto the bed. We both exhaled and said “ah…” The moment was over. I started to slowly withdraw from my lover. Stacie made a few more, half-hearted, clenching movements and I laughed. “Nice try you naughty vixen! Now I know why you were wearing panties when you got arrested. ” She leaned into me and we kissed some more. I tried a few more tittie sucks and nipple tongue twirls but we were both done. My cock pulled free.

Stacie rolled over and snuggled up immediately to me in the classic spooning position. She pulled me as close to her stomach as possible. I could feel the length of Stacie’s softening shaft on my butt. I reached back and lifted my butt cheek and Stacie’s penis fell into my crevice. I released my cheek and it dropped, trapping Stacie’s penis like a hot dog in a bun; I could feel it squirm as it was retreating. We laid still. I made a clenching move and I felt Stacie’s cock twitch. “Oh, who’s the vixen now?” she asked. “I can feel your penis shrinking. Don’t forget it’s my turn next” I said. Stacie gave me a kiss on the back of my neck; she cupped my breast. “That reminds me. Unlike the vibrator, you are bigger than one inch in diameter. I had to work at letting you in. It will be easier next time.” She kissed my neck again.

I made another clenching movement and got the desired twitch again. “We best save our energy as Jackie and Rose may be stopping by later.” I glanced at the wall clock and immediately sat straight up. “Oh, crap. Lunch is in an hour and we need to clean up, get dressed and slap on some makeup or we’ll be late.”

Stacie looked over my shoulder, saw the clock and also sat up. “Will you get me something to clean up with… I feel something wet leaking from my ass.” Looking around, I tossed her a box of tissues from the night stand and said “This will have to do for now. They really need to give us baby wipes. This is primitive! The least they could do is to provide us with panty liners.” Stacie did her best to clean herself and climbed out of bed. We had to get a move on.

I loudly laughed as Stacie waddled toward the bath room. She had wedged a couple of tissues in her butt crack and it looked as if she had a rabbit tail. Looking over her shoulder into the full length mirror Stacie saw the tissues hanging from her butt and she began laughing too. From the video monitoring room Martha and Miss Diane broke into laughter.

Stacie sat to pee and tried, without success, to squirt some of my cum from her bowels. She wiped herself and muttered “I’ll be getting a wet spot on my skirt for sure. There’s no time to douche.” I pondered the situation and said “I have a solution.” Reaching into my purse I produced a tampon and held it up for Stacie to see. “We have to go to plan B. When you’re done in there come here and I’ll get you squared away.”

Stacie pulled up her panties and walked over to where I was sitting and asked “Ok, now what?” I replied “Watch and learn. First you peel open the tampon wrapper, remove the tampon and extend the applicator rod. The tampon is inside the applicator. See that string hanging out of the rod? That’s what you pull on to remove your tampon. The tampon itself is on the other end of the string and is inside the plastic applicator. They are skinnier than the vibrator and they are skinnier than me.”

I continued. “We’re lucky that they gave us Lite Days tampons as they are thinner than regular flow tampons. They are more comfortable and you don’t feel like you always need to take a dump. And trust me; you do NOT want to shove a heavy flow tampon up your ass. It would make you go cross-eyed. Now turn around, back towards me, drop your panties, bend over, and spread your legs. I’ll do the rest this time.”

Stacie did as instructed. “Now spread your cheeks. These come pre-lubricated but it’s never enough, especially for your first time.” I opened her tube of lube and applied about a dime sized amount of lube to the top of the tampon and smeared it around the top half of the tampon. “I’m now going to use the applicator rod to insert the tampon into your anus. When it’s in far enough I’ll keep hold of the applicator and push out the cotton part of the tampon into you. Then I’ll pull out the rod and plastic applicator. The cotton tampon remains inside you; the removal string hangs outside. You can then stand up and go about your business with no leaks or wet spots on your clothing. You have to be sure you get past your sphincter. If it feels like you have a hot dog hanging out your anus then you need to insert it deeper. You should feel like there’s nothing there. I found a diagram that will help you understand proper tampon placement for males. Look and learn. It MUST be inserted beyond the sphincter ring of muscle.” Again Stacie thought ‘How does she know these things’?

I showed Stacie a detailed diagram of what I was referring too. Very detailed!

It only took about 20 seconds and it was done. Stacie had her first tampon. I lightly tugged on Stacie’s hanging string. “Did you feel that tug Stacey? Now you reach back here and give it a gentle tug just so you know where to find the string.” Stacie found the string and gave it a gentle pull. She was pleased that it would take a stronger pull to pop it free. She pulled up her panties and continued with getting ready for lunch.

Stacie and I were ready. New pantyhose, clean panties, proper lipstick, a fresh coat of mascara, curled eye lashes, correct jewelry and a hint of perfume. I took the extra time and added her eye liner. It looked perfect. Stacie had tossed our old panty hose into the trash. She was surprised to see me retrieve them from the trash and see me cutting the legs off of the panty part. I threw the legs away which left me with the control panty part. “What in the world are you doing!? Stacie asked. In reply I said “Remember how our crotch bulges were starting to show? If we double up on the control part of the panty hose we should be less obvious. Just pull them on like an extra pair of snug panties. I just don’t want to tuck and tape or wear a gaff.”

‘Tuck and tape? Gaff? What in the world is the girl talking about’? thought Stacie. ‘The use of an extra control top is pretty damn clever, brilliant actually.’

Lunch –Day 17

Lunch was the usual. It gave us girls an hour to talk and gossip amongst ourselves. “Stacie, what was all the noise we heard coming from your room? It sounded pretty serious” asked Fannie from down the table. Stacie began blushing and then volunteered “My roommate and I were getting better acquainted.” The table laughed. Beth ventured, “Tracie and I found ways to pass the time too.” Lunch ended, lipstick was reapplied and the table was cleaned.

Miss Diane and staff member Cindy entered the dayroom. Cindy was wearing Ruby earrings. Miss Diane began the briefing. “This afternoon will be devoted to watching two important videos on feminism and the history of the oppression and discrimination of women in America. Around 4 PM you’ll be on your own until diner at 7PM. Take advantage of your free time and get to know the other girls in our group.”

Cindy spoke next. “It appears we omitted some key information today. It concerns your vibrators. Joan brought it to my attention. Your vibrator is just that; it’s a two speed, AA battery powered vibrator. The ‘turn on’ button, pun intended, is in the end of the grip. Use your thumb to activate it. Press once and it is on slow, press down again and it goes full speed. Press three times and it turns off. I’m sure you’ll put this information to good use. Joan did and she has already completed four of the ten mandated rectal ejaculations as outlined on the Orders of the Earrings. She attained these credits between breakfast and lunch. If you need extra batteries just ask.”

Joan blushed deeply and the table gave her a friendly round of applause. “You go girl!” shouted Fannie. “Can I have more batteries now?” asked Rose. “Thank you Joan,” quipped Jackie. You could hear several of the girls opening their purses so they could more closely inspect their ‘new best friend’. The buzzing of the vibrators was noticeable as they turned them on and off. The buzzing stopped but the giggles did not.

We followed Cindy and Miss Diane into the viewing room. As Jackie passed Cindy she said “Pretty earrings” and then took her seat. Cindy smiled and walked over to let Miss Diane know Jackie’s comment. Miss Diane made a note on her clip board. The first movie started.
The movies were finally over and we were on our way back to our rooms. Dinner would be in about 4 hours. Jackie took me aside and said “I’ll see you later. Rose wants to stay in the room and play with her vibrator.” She winked at Stacie.

Stacie and I stepped into our room and each found three items that had been placed on our beds. There was a container of baby wipes, two packs of panty liners, and a pack of AA batteries. “Wow! I guess they do hear what we say.” Going into the bath room Stacie found a box of tampons. “Look here Jenny, we get to share a box of tampons!” She sat, peed and stepped out of her pantyhose and tossed them on her bed. She returned to the toilet area, fresh tampon in hand, dropped her panties, bent over and pulled out her used tampon. It was soaked. She wrapped it in toilet paper and put it in the trash. She lubed her new tampon as I had instructed and was able to insert it with little effort. She tugged on her string for assurance. The insertion and her tugging her string were slightly erotic for me for me to watch.

Dressed only in our panties and bras we laid down in our own beds to relax, cool down and collect our thoughts. I removed my bra for comfort. My developing breasts were pretty I thought. My nipples were relaxed and ‘limp’ so I played with them a bit to make sure they responded. They did. They looked like perky raisins. It felt very pleasant to play with them.

Less than fifteen minutes had passed when we heard the tapping of finger nails on our door. Without rising from our beds, in unison, we said “Come in.”

The door opened and Jackie came in. She placed her purse on the night stand and closed the door. She too had removed her pantyhose but had clearly freshened up her makeup and lipstick. She looked nice in her skirt. Her blouse had the top two buttons opened. The pleasant aroma of a strawberry musk perfume followed into our room.

Stacie and I got up from our beds to greet our visitor. Stacie was about to shake hands but decided on a generic kiss of ‘hello’ on Jackie’s cheek. “Welcome” said Stacie. Jackie returned the cheek kiss and then stepped closer to me. “We’re glad to see you, please come in” I said and leaned in to do the cheek kiss too. Jackie dodged a bit and planted more than a generic kiss on my red lips. Jackie lingered a bit on my lips and flicked her tongue along them. “You’re lipstick tastes yummy” Jackie said. “I’ve been meaning to get to know you both better since I first saw you”.

Jackie stepped back but held my hands. She gave me an appreciative look-over and said “Your eyeliner sets you apart from the others. It looks like your titties are coming along fine. They must be at least a B cup. I’m sure glad you have your bra off.” She reached across and tweaked my nipples. Jackie pulled me closer and planted a kiss on my left breast leaving a red lipstick mark that ran over onto my left nipple. I jerked a little and said “Wow, that feels pretty nice.” “It did? “ Jackie asked. She then leaned forward and began suckling on my right tit, swirling her tongue in as sensuous way as she knew how. My nipples got rigid and my knees went weak. I felt the need to sit down and I sat on the edge of my bed. Due to involuntary response I was beginning to grow a crotch bump; it was beginning to take shape.

Turning to Stacie Jackie said “I don’t want you to feel left out” and she gave Stacie a non-generic kiss that lasted a pleasant length of time, and a hug. As she was hugging Stacie, Jackie reached around and unhooked Stacie’s bra. Following Jackie’s lead Stacie shrugged here bra to the floor and gave Jackie a deep soul kiss. Stacie’s hand immediately went down to where Jackie’s swelling cock was. She gave it a sexy stroking. Still hugging Jackie, Stacie reached to the back of Jackie’s bra and unhooked it. She then unzipped Jackie’s skirt. Becoming bolder Stacie pulled Jackie’s skirt completely down. A wet spot on the front of Jackie’s panties was already the size of a quarter.

Stacie stepped back and sat down beside me. “Care to have a seat?” I asked. I scooted over to open a place between me and Stacie. Stacie said “You certainly don’t mess around!” and patted the empty place on the bed. Jackie laughed and said “Yes I do! Why do you think I’m here? I want to knock out some of the program requirements.” Jackie plopped down between the two girls and began rubbing us both through our nylon panties. She was rubbing up and down on both of our panty clad penises at the same time. She was not only talented she was also determined. All three of our penises were beginning to poke above the top of our panties. Jackie used the thumb, ‘spread-the pre-cum’, technique on the both of us at the same time. Jackie’s wet spot was now about the size of a 50 cent piece. The smell of sex was in the air.

I leaned over and gave Jackie a long kiss on her mouth, and made little tongue probing moves. Jackie took the bait and in a brief monument we were engaged in sensuous French kissing. I moaned and reached into Jackie’s panties and began some pre-cum spreading of my own on Jackie’s cock head and shaft. It was Jackie’s turn to moan.

I had made about three full length strokes on Jackie’s wet shaft when Stacie reached over and swatted my hand out of the way. “Hey, leave some for me!” she said. Grabbing Jackie’s shaft with her whole hand, Stacie resumed a slow milking motion up and down Jackie’s now slick shaft. Jackie had both of our shafts in a similar grip and the three of us sat on the bed slowly jacking each other off. Stacie leaned over and kissed the tip of Jackie’s dick, making an attempt to lick it into her anxiously waiting mouth. It was marvelous way to spend the day.

I removed my hand from Jackie’s penis and asked, “Wait a minute, what do you have in mind?” Seizing the opportunity, Stacie leaned further over and swirled her tongue on the head of Jackie’s cock. It was there for the taking. Stacie had started some tip suction that was drawing Jackie’s glans into her mouth. She had just circled her lips around Jackie’s glans when Jackie stopped her. She leaned over to Stacie and licked her own pre-seminal fluid off of Stacie’s lips. “Thanks darling that was very special.”

Jackie stood and turned to face us both. Hooking her thumbs into the side of her panties she pulled them down her legs and kicked them aside. Stacie and I were at face level of a raging hard on. Jackie stepped over and offered her slick cock to me which I gladly accepted. I made a point of kissing Jackie’s cock tip and leaving my signature red lip print. I had just slurped Jackie’s cock to beyond her glans when Jackie stepped back. There was another audible pop as the suction broke. I licked my lips in an effort to taste Jackie.

Jackie said “Jenny, ever since I saw that you could cum across the width of a table, I’ve wanted to get a piece of you. I’d like to feel you squirt onto my tonsils.” “Stacie,” she continued, “when I heard you wailing the other day I knew that we needed to hook up. Both of you raise your legs and let me pull your panties off.” A second later there were two sets of legs pointing toward the ceiling. Jackie laughed as she went to her purse and retrieved her lipstick and vibrator. She stepped forward and pulled off Stacie’s panties first and then mine. Our two cocks were standing tall and proud in anticipation. Standing between us Jackie twisted open her lipstick and applied a thick coat. She tossed the tube and vibrator onto the bed. We remained seated on the edge of the bed.

Jackie stepped between Stacie’s legs and said “It looks like you’re leaking.” Indeed. A large drip of clear cum was on the head of her penis and was starting to run down her shaft. Jackie got on her knees and licked it off. Jackie then kissed Stacie’s penis tip making sure to also leave a red imprint. She then sucked in the penis to just beyond the neck and pressed her lips together leaving yet another red ring. Jackie’s lips were snug, warm and firm. Jackie swirled her tongue and moved her tightened lips up and off Stacie’s penis, slathering it as she went. Stacie looked disappointed that Jackie had pulled off. Jackie looked over at me and said “Don’t worry, your turn is cumming.”

Jackie looked back at Stacie, gave her a wink, opened her lips and dove back down Stacie’s shaft leaving another red ring at the base of her cock. She sucked and twirled her way back up the shaft dragging her tight lips up and off the penis with a milking move. Stacie moaned loudly like she does. She closed her eyes and leaned back on her elbows. Jackie reached again for her lipstick and reapplied another coat, tossing the tube back onto the bed next to the vibrator.

Jackie shuffled over, on her knees, to me. She placed a small throw pillow on the floor between my legs and gripped my shaft. “This is my real target” she said.

Maintaining a firm grasp on my rigid shaft Jackie pulled it forward and bent slightly down and repeated what she had done for Stacie, making sure to leave her trademark double red rings on my shaft too. She was starting to bob and fellate me enthusiastically when Stacie asked, “How are we going to make this work? Jenny promised ME her cherry!” Jackie slurped up and off of me. There was another breaking of suction pop noise. “I have an idea but it’s not polite to talk with your mouth full.”

Jackie explained “If Jenny moves to the end of the bed I can suck her off with no problem. That means you’d have to fuck Jenny doggie style. You’d both be on your knees. Is everyone ok with that?” We eagerly nodded our heads ‘yes’. I hurried to the end of the bed. Jackie went to stand in front of my lips. Her cock was bobbing in my face. Stacie grabbed a tube of lube and positioned herself at my butt. Jackie had the foresight to suggest that once Stacie got her cock into my puckering sphincter then she would start what she had came over to do.

Stacie was so excited that she had trouble opening the lube. I looked over my shoulder and said, “Don’t skimp on the lube.” Stacie applied a liberal coating of lube on her penis giving it several strokes up and down to grease it good. Applying a good amount on two of her fingers she smeared a teaspoon full amount all over my anus. She used one finger to lube just inside my sphincter. She circled my innards twice. I gripped Stacie’s digit by clenching. Stacie was kneeling behind me where she needed to be and placed her cock head right on target. I was accommodating enough to use one of my hands to spread my cheeks wider.

Stacie pressed forward, made contact with my puckering hole and then pressed forward again and got in about four inches. I exhaled and tried to relax. “Can I start on Jackie now?” I gasped. I was licking my lips. “Wait a moment, I want to get settled. I’ll tell you when!” Stacie said. Stacie pulled all the way out and then shoved her cock back in. She had made it to five inches this time. On the third thrust Stacie was firmly in place. “Go for it!” she barked. Jackie stepped a bit closer to my lips. I opened my lips and was about to suck in Jackie’s cock when Stacie made a sudden and earnest forward thrust that propelled me onto Jackie’s cock. It hit the roof of my mouth and caromed to the back of my throat.

Stacie stopped for awhile and savored the nice warm feeling of my tight ass. This gave me time to begin Jackie’s blow job. I had made several runs up and down Jackie’s dick when Stacie began a nice thrusting. I gasped but remained sealed on Jackie’s shaft. I began a nice head bobbing motion and Jackie started a pleasantly slow face fucking motion. The three of us set up a steady and mutually satisfying rhythm. We were all either moaning or grunting. It wasn’t long until we were all getting close to our orgasms. Jackie was making new wiggle movements with her pelvis and I was panting in anticipation. Stacie was enjoying her ride. The friction of my clamping, gripping and milking actions on her penis was pulling her towards a climax.

Seeing Jackie’s vibrator on the bed Stacie picked it up and turned it on. She rubbed it around on my scrotum and then held it on the base of her cock. The vibrator buzzing transferred up her shaft and transferred to my anal rings and beyond. It was another magical moment. I began a fevered and quicker head bobbing which caused Jackie to speed up her trusting. My tongue was alternating from trying to circle and hold her cock to cock tickling only the underside of her glans. It’s something that I like done to me.

In an inspired act Stacie’s took the vibrator and began rubbing her own balls. Less than 45 seconds later Stacie yelped “Oh, god!” and spewed her cum deep inside me. She pulled me back getting her dick as deep as possible in me. She held me tight. She let loose another blast. The warm feeling of Stacie’s sperm caused me to have a deep, twitching, orgasm that caused my eyes to roll back in my head. I did a tight, slow sucking withdrawal on Jackie’s slimy shaft and immediately slid back as close as I could get to Stacie’s cock base. I wanted to keep Stacie’s cock deep inside me. I made sure to clench and milk her. She thanked me by making herself throb large. I was sitting on her dick; keeping it deep.

Jackie leaned forward to make up for the distance between us and came in wave after wave of cum spurts that filled my throat and mouth to overflowing. I leaned forward, while still impaled on Stacie, and slid my lips down her as far as I could go. Jackie began knelling on the end of the bed which allowed me to plummet down her shaft again. I sucked and lip-squeegeed the last bit of sperm from Jackie’s balls. I stopped moving and held my mouth still, savoring the throbbing and ecstasy of the moment. I took my time in releasing the lip grip I had on Jackie’s cock, withdrawing slowly. Meanwhile Stacie enjoyed being packed into my ass as far as she could go. I could feel her try to squirt one more time.

A moment or two went by and I released my lips on Jackie shaft. Stacie did a slow withdrawal from my rectum that was pleasurable for the both of us. I kept clamping and milking Stacie as she pulled out. Eventually we were all uncoupled and breathing heavy. I turned my head toward the ceiling camera and stuck out my tongue to show off my prize. Still staring at the camera, I slowly swallowed most of the mouthful of Jackie’s cum, retaining about a half a shot glass of cum in my mouth.

I climbed gingerly off the bed and embraced Jackie. Jackie hugged me back and kissed me. I slipped her a swig of her own cum. Surprised at first she looked up at the camera, stuck out her tongue to display the cum and made an obvious swallow. Stacie was off the bed and she and I kissed deeply. “Lick my lips and you can taste Jackie.” Stacie did what she was asked.

We fell exhausted but satiated back onto the bed. Our penises slowly went limp. Stacie was the first to move and grabbed a baby wipe to clean her dick, passing the container over to us. Only I needed one and I made wiping motions up and down my crack. Jackie just smiled and laid there. “Jenny, you do know you still owe me a tonsil shower.”

We all eventually clambered out of bed. Jackie retrieved her lipstick and vibrator. As she was putting the vibrator back into its travel bag Jackie said to Stacie, “Using that vibrator in the way that you did was brilliant! Where did you get that idea?” Stacie said “Jenny inspired me based upon the first day we got our vibrators. Speaking of vibrators, it’s too bad Rose didn’t join us today. She really seems to be in love with hers.” Jackie agreed “It was buzzing before our door had closed. I hope she doesn’t wear it out!”

I looked down at the old blue bedspread we had just gotten off of and exclaimed “Damn, look at the wet spot I left. I’m seeping for sure. I wonder if they ever change the linen. I’m going to need a tampon.”

Stacie looked startled. “Tampon! Damn, I forgot to remove mine last night. Why didn’t someone tell me my string was showing?” Jackie looked bewildered. ‘Did she say tampon?’ she thought. Stacie rushed into the rest room, bent over and quickly removed, wrapped and disposed of her used tampon. “While you’re in there would you mind bringing me one? I don’t feel like douching right now” I complained.

On her return Stacie gave me what I’d requested. In a flash I had it peeled, lubed and inserted. I gave the string the tug test for reassurance. Jackie asked me to turn around, bend over and show her my butt. Sure enough there was a little ‘mouse tail’ of string clearly hanging from my recently fucked rectum. She gave it one soft tug. Now Jackie was truly amazed. “Err… would you ladies mind telling me what the deal with the tampons is?”

Stacie replied “Jenny taught me. It works fine, stops leaks and saves a lot of time.” She went on and explained all to Jackie. Jackie just shook her head in disbelief and said “You learn something new every day. I’ll have to keep that trick in mind. You never know when you might need such a time saver.”

Just then an announcement came in over the intercom. It seems pantyhose would not be required for the rest of the day. “That’s a relief” we all said in unison which caused us to break into laughter.

“None the less we better get ready for dinner. Since we don’t need the pantyhose I’m going to try a new style of panty. I saw a pair of cute tap pants that I’ve been dying to wear” I announced. With Jackie and Stacie both watching, I pulled out a pair of peach colored tap pants and slid them on. Next I grabbed a panty liner, peeled off the adhesive and attached it to the crotch of my tap pants. “There now, no wet butt drools for me tonight. A box of the thin Kotex pads with wings would be useful.” I then put on the top portion of the legless control top pantyhose I’d made earlier.

Jackie turned towards Stacie and asked “How does she know about all this stuff?” Stacie shrugged and replied “I’ve been asking that too. Pretty amazing; sort of like a Fairy MacGyver.” We had a good laugh.

Stacie, Jackie and I had pretty well pulled ourselves together and Jackie was about to leave. She had picked up her purse but stopped at the door and asked, “Jenny, would you apply some eyeliner on me before I leave? It looks so nice on you.” “No problem, have a seat. I was going to touch up Stacie’s anyway.” It only took me few moments and Jackie was done. She looked into the mirror, batted her eye lashes and smiled. Standing up she gave me a last kiss and said “Thank you, darling.” I returned her kiss and could feel her penis throb. “You better leave.” I opened the door and as Jackie exited I gave Jackie’s crotch a rub.

The door closed and I turned my back to the door and leaned against it. I closed my eyes and took a few deep breaths to relax. Stacie looked over and asked “What’s going on?” I took another deep breath and said “I REALLY want to fuck her.” Recovering my composure I said to Stacie “Hey, you bring out the same feelings in me.” Ten minutes later we left to the dining area.

Dinner- day 17

Dinner was just another chance to get acquainted and swap stories. Jackie made a point out of sitting next to me. Between forkfuls of salad she stroked my thigh. Her hand crept under my skirt and her fingers made contact with my crotch. I spread my legs wider. “Stop that!” I whispered. Jackie giggled softly and several girls looked to see who the new lovers were. “I just wanted to see if the panty liner and control tops worked… they don’t!” “At least there won’t be a wet spot!” I whispered.

Dinner ended and Cindy came in to make the usual announcements. The group noticed her three earrings, gold hoops, ruby and sapphire gems. “As a group you’re coming along fine. There are a couple girls that need to start meeting the requirements. A vibrator by itself will not get you out of here.” The entire table turned to look at Rose. “With that in mind I’m giving you your first Score Card. You can also find it on your in-room TV. It’s updated as needed. Take a look ladies. You may want to pick up the pace. If we’ve missed anything let me, Martha or Miss Diane know. I’ll see you in the morning.” Cindy turned and left.

We picked up the score cards and studied it intently. Beth turned to her roommate Tracie and testily said “I wondered where you went last night!” There was more than a little jealousy in her tone. The table stood and we started to make our way back to our rooms. It was only 7 PM and the night was young. As we walked some of the girls were putting their arms around each other or were holding hands. There were several new pairings and in some cases there threesomes making nice. I had Jackie held around the waist and kissed her ear. “Are you busy around 7:30? I’d like to stop by for a visit. I don’t mind if Rose is there. In fact it could make things interesting… like this afternoon. Stacie is expecting a guest that’s a little shy.” Jackie gave me a not so subtle goose to the butt with her middle finger and said “See you then, babes.”

By 8:15 PM I was fully buried up to the base of my cock in Jackie’s ass. Clothing and underwear were everywhere. Jackie was on her bed with her legs over my shoulders. I had found what I’d always wanted. And it was good. My strokes were deep and well timed. Jackie was the best ‘milker’ I had ever had. She clamped so tight it made both the inward and outward moves exquisite. She was a human squeegee.

Rose was on her knees and her ‘guest’, Tracie, was sitting on the edge of Rose’s bed enjoying a perfect blow job. Tracie came quickly and loaded Rose’s mouth. Rose immediately joined Tracie on the bed. As she was slowly swallowing Tracie’s sperm, and before it was gone, Rose was already rapidly shoving her vibrator in and out of her own ass with the vibrator turned on high. She was panting like a dog in heat. She did like her ‘magic wand’. A few moments later she was bucking and spasming on the bed. It was noted that Rose got two scores added to her Scorecard in one ‘session’; blow job and vibrator.

Tracie recovered enough to take over the thrusting and twisting of the vibrator for Rose and was doing the ‘wine cork’ routine. Tracie turned it on high and made contact with Rose’s prostate and held it there. Rose squirted so hard that her cum landed on her tit. Instantly Tracie was on it, sucking and licking Rose’s cum off her body. Or maybe Tracie was sucking and licking Rose’s tits just for fun. It didn’t matter as they were both enjoying it.

The sights and sounds of Rose and Tracie were amazing to witness. It was just before 9 PM when I kissed Jackie good night and I was about to leave. Jackie grabbed my hand and said “Bend over.” I did and Jackie grabbed my dangling tampon string and slowly pulled it out of my ass. I immediately stood up and twirled around. Jackie had a big smile and was holding the sperm soaked tampon like a trophy. “I was afraid you’d forget. Need help with a fresh one?” I laughed and said “No, not unless you need the practice.” And opened the door and left.

When I opened the door to my room I found Stacie bent over a chair and taking it up the ass from Beth. They had just finished and I was just in time to see Beth’s penis plop free. Stacie blushed and began putting the baby wipes to good use. Turning to face me, while continuing to clean herself, Stacie offered “Beth’s cock has a lot more life in it in case you’re interested. It’s insatiable!” Beth had a cute smirk on her face and was using her vibrator to motion me over to her. “Jen,” she purred, “If you’ve got the time I’d like to show you a new way you can use a vibrator. It’s pretty innovative and feels so very, very nice for both of us. Just look at Stacie’s grin.” She was slowly hitting the palm of her hand with the vibrator while awaiting my reply. I’m not sure how she sustained it but she was still very erect.

I politely declined mentioning that I needed to remove my makeup and get some rest. “I am truly worn out; maybe another time. It sounds like fun.” I entered the bathroom and closed the door.

Day 25… or was it 35?

Breakfast

Breakfast was no big deal; the usual round of vitamins and a basic breakfast. The dining table was all buzzing with yesterday’s news, when would the Scorecard be updated, and Rose’s love affair with her vibrator was topics. It was noted by consensus how larger their breasts had become and how grateful we were that the itching had stopped.

As breakfast was breaking up Cindy announced that me, Stacie, Jackie and Tracie were excused from the morning’s activities. We were told to report to the administrative building for a progress evaluation meeting. We were asked to remain at the dining table after the others had left. Another wave of buzzing and speculation rose from the table. The rest of the girls finished their breakfast leaving us four at the table.

Cindy came to our table. It seems that Jackie and I were to meet with Miss Diane and Stacie and Tracie were meeting with Martha. “Follow me girls” Cindy said. We all stood up. I gave Stacie a hug and a quick peck on her cheek. “Good luck” Stacie said. I held Jackie’s hand as we walked to the admin building. No one had been there since our arrival.

Cindy led us down a hallway and told Stacie and Tracie to enter office 2. Jackie and I were to go into office 2. The agenda would be explained when we were inside.

We entered office 2 and sitting behind a large desk was Miss Diane. She looked as beautiful as always but today she was wearing a lovely silk lavender colored chemise. Two chairs were in front of her desk. We waited by the door for instructions.

Miss Diane began. “Good morning ladies. Before you sit down I want you both to strip down to just your bra and panties. To your right is a shelf to put your purses and clothes on. When that’s done please take a seat. Also be advised that there is audio and video monitoring in here.”

As I we were disrobing I asked Jackie “Is my makeup ok?” Jackie nodded her head to indicate yes. We were soon seated and facing Miss Diane.

“You are not in any kind of trouble but on occasion we like to have more informal conversations with our students. What’s happening here is also happening with Martha.“

“I want to begin with telling you how feminine looking you both have become. The eyeliner in particular was a nice touch and its use has been picked up by several of the girls. I know this began with Jenny. I also know Jenny was responsible for several other ideas. Her comments are the reason that additional feminine items were placed in your rooms. The use of tampons was a new concept we hadn’t thought of before. We feel in enhances the feminine experience we are looking for. Jenny, when you get back to your room you’ll find a new bed spread that is much nicer and girly than that old blue one that suddenly became soiled.” I turned three shades of red at the compliment.

“Also you ladies have become obviously more endowed in the chest area and before you leave you’ll be given several new bras that better enhance your pert breasts. Unlike standard issue bras these will be prettier, under wired, balconnette demi-bras that will enhance your cleavage. There will be additional clothing and items that I’ll mention later. Don’t be surprised if the other girls are somewhat jealous.”

“As a reward for what I’ve already mentioned, and because of your progress on your Scorecards you will be issued two inch gold hoops. I think that you’ll like the feeling when they bounce or touch your cheek. They’ll remind you of how girly you’ve become. Please remove your studs now. You may keep them. If you advance to additional ear piercings, and we’re sure you will, the studs will come in handy. Matron insists on doing second piercings herself.” We did as we were told.

Miss Diane stepped from behind her desk and gave the girls a small jewelry box that contained the new two inch gold hoops. “Take a box, take out the hoops and place the studs in the box. Because you ladies seem to be so close, you are to insert the hoops in each other’s ears. The staff jokingly calls them ‘training wheels’.”

Doing as instructed we inserted and closed the hoops in each other’s ears. There seemed to be a louder ‘click’ sound as they snapped shut than normal. The proximity to each other, clad only in panties and bras, (and combined with the touching of each other’s ears) was beginning to have an effect on us. An obvious erection response was creating panty bulges. Out of impulse we kissed each other deeply. Our passion and bulges increased. We held hands and turned to face Miss Diane.

“These earrings have a thicker wire and the click you heard was locking mechanisms that can only be opened by a staff member. They earned the nick name ‘training wheels’ because when you’re giving someone a blow job they can hook their fingers in the hoops and guide you to where they get the most pleasure. Up, down, sideways; just tug and pull gently as you don’t want to tear out an ear. I want you to explain their functionality to the other girls. They get theirs NEXT week” Miss Diane paused to let all this information sink-in.

“To give you a practical experience with your ‘training wheels’ I have an exercise that you must do.” Miss Diane opened and discarded her robe. She was dressed in only a breast enhancing bra, and a garter belt with silk stockings. She wore no panties. The most noticeable feature was that she had at least an eight inch cock dangling between her legs! It was thicker in diameter than any cock we’ve seen since arriving. It appeared to be almost three inches in diameter. It was not totally flaccid. In fact it appeared to be ‘on the rise’.

She smiled at our surprised look. In a dramatic gesture she gave her shaft one slow stroke from base to tip. The bulges in our panties increased. “It appears you should have worn that extra control top panty that you invented, and a Lite Days panty liner, as I see some wet spots” she said pointing towards are panties. “You must have noticed the thickness of my cock. Sometimes a bit of a stretch is good for you as it prepares you for what may find in the future.”

She walked over and sat on a love seat that had been covered with a large towel. There were long skinny pillows waiting on the floor. “You are to remember that YOU are to service me. I DON’T service you! Staff takes care of each other, which IF you elect to remain at The Nest, could be a good thing. Both of you are to remove your bras and then come over here and kneel on the pillow.” The bras came off quickly and were tossed on the shelf. We were soon kneeling as instructed.

“Jenny, you are to kneel between my legs. Jackie you are to kneel beside Jenny. Jenny, you are going to give me a partial blow job. Jackie will finish it when I say so. Maybe you will learn something by observing each other. Before you start I want you to reapply your lipstick. I want to see a red ring as far down my shaft as possible.” Miss Diane passed me a tube that was my usual shade of red. I quickly slathered it on. Miss Diane inserted a finger into each of my new hoop earrings and gently guided my mouth to her cock. “Get started Jenny.”

I reached over and hefted Miss Diane’s penis. It was getting stiffer by the second. It seemed so long and BIG! I encircled the base using my middle finger and thumb. It was almost three inches wide for sure. I first made two pumping motions up and down her shaft and then used my thumb to smear the inevitable, clear, pre-seminal fluid around her cock head. I dragged more of the slippery wetness down her shaft. I made one last jack-off stroking motion and then kissed her cock head leaving an expected red imprint. Miss Diane guided me down her dick. I left the requested red rings as far down as I could go. Jackie got so hot watching that she started rubbing one of her own nipples while fingering and teasing one of nipples. Despite having a cock in my mouth I made a low moan but never broke suction. I felt my earrings pulling my head back up to the top of her shaft. I spent more time and attention to the top of Miss Diane’s cock.

Making an ‘O’ with my mouth I put a lip grip just beyond her cock-head, using my tongue to lubricate and tantalize. I also used my tongue on Miss Diane’s pee hole which caused an involuntary twitch of her shaft in my mouth. She made a low groan of appreciation. Jackie got behind me and cupped and fingered both of my tits while I was working on Miss Diane’s penis. It made me feel hot.

I made three or four up and down runs on her shaft and then dove for the base just as my earrings were signaling me downward. Holding for a moment, to tongue tickle and swirl, I pressed my lips tightly on the shaft and left another red ring as far down her penis as I could. I was about to gag so I slow milked my way back up her dick giving a lot of tongue action as I went.

I enjoyed rubbing Miss Diane’s stockings and tugging gently on her garter straps. ‘Damn, that’s hot!’ I thought. Making one last tonguing of the neck of her glans I popped free, took a deep breath, and was about to go down for more. Miss Diane gently held my chin to make me stop, looked me in the eyes and said “You can stop now darling. You learned why we call the hoops ‘training wheels’.” She removed her fingers from my hoops. “It’s Jackie’s turn.” We traded places.

“Jackie, here is a darker shade of lipstick. You know the drill. Put it on. I’m curious as who can take more.” Jackie did as instructed keeping direct eye contact with Miss Diane as she did. Jackie looked down at Miss Diane’s cock, rubbed her inner nylon encased thighs, and also left a kiss print on the other side of her cock head. Miss Diane grabbed Jackie’s hoops and gave them a tug to get Jackie’s attention. Jackie gripped the base of Miss Diane’s shaft and continued where I had left off. I went behind Jackie and was massaging and caressing both of Jackie’s tits like she had done for me. I loved to thumb and tweak nipples. Anybody’s nipples.

With such encouragement Jackie’s head bobbing increased. Sucking her way down the shaft, because her earrings were pulling her downward, she could feel the cock head at the back of her throat. She clamped her mark about four times. On the third time Miss Diane came. Lots of the sperm seem to go immediately down her throat but a lot didn’t. Jackie had a mouthful of love sauce. Opening her mouth to show Miss Diane her mouthful of cum, Jackie winked and swallowed.

Both of us were still on the pillows. Jackie pulled me close and kissed me squarely on her lips. She also spewed a teaspoonful of Miss Diane sperm into my mouth. I didn’t break our kiss. Instead I ran my tongue back and forth on Jackie’s lips. Larger wet spots were spreading on our panties. Miss Diane watched as we each reached over and grabbed and stroked each other’s hard on. It was a beautiful thing.

Sensing that this was a special moment Miss Diane stood up and told us “You may as well finish each other off. You can “69” on my love seat. I need to recover for awhile anyway. Besides I’d like to watch.” In an instant Jackie and I were on the love seat and were head bobbing each other with urgency in the classic “69” position. There was some mutual tugging and pulling of our new ‘training wheels’. Within moments of each other, we spewed. I told Jackie “There’s the tonsil wash I owed you.” We sat up and turned to face Miss Diane, opened our mouths and we swallowed the leftovers. “So noted” Miss Diane said and pointed to the ceiling camera.

Miss Diane said “To show our appreciation we have a few things for the both of you. We’ve prepared a goodie bag for each of you that includes: Victoria’s Secret garter belt, several pairs of 15 denier nylons, 3 under wired size B demi-bras with cleavage enhancers, Victoria’s Secret panties that has your names on them and an eight inch silicon dildo. Wear them and use them with pride. And please take the lipsticks you used today; your names are engraved on the tubes. We’ve included a bottle of blue nail polish that will be mandated next week. You’re ahead of the times.” Handing us each a new Victoria’s Secret bra Miss Diane told us to put them on. Both were midnight blue and looked very sexy.

“There’s one more token of our appreciation: Immediately after leaving here you will get a professional makeover, manicure and eyebrow waxing. Also we’ve noticed that your natural hair length now allows us to give you a hair salon pixie cut. No need for a hot wig anymore.”

Assuming we were finished we were making our way to our purses, clothes and goodie bags.

Miss Diane said “Hold on, there’s two more things before you can leave. First, Jackie was able to take more cock then Jenny.” She pointed at her semi-flaccid penis. The lipstick marks were clear. Jackie was able to eat about ¾ inches more cock then me.

“The last thing before you leave is a tightness test. I’m going to penetrate you both. I won’t cum in your ass. I’m glad I’ve had some time to recover from my blow job. Both of you girls remove your panties, go to the front of my desk and wait for me. I need to get my lube and a few warm and wet wash cloths. Jenny, you’ll be first.” Stacie and I looked at each other in surprise. Neither of us had seen THIS coming. The eight inch, three inch diameter snake was going to invade us!

We were at the desk and Miss Diane brought the lube and warm wash cloths. “Here’s the drill. Because I’m fucking Jenny first she will lube me to erection, face the desk and bend over with her hands on the desk. I’ll fuck her for awhile, perform a tightness test on you and then withdraw. Jenny will then take a warm wash cloth and clean me off. Jackie will then lube me again, insure my erection, bend over, grab the desk and get fucked. I’ll check her tightness, withdraw and she’ll clean me with another wash cloth. You’ll get dressed, take your presents and report for your makeovers.”

Handing me the lube she ordered “Get started”. Taking a large amount of lube I picked up Miss Diane’s cock and began smearing it on the head of her dick. I made a palm swirl on the cock head and then ran the lube down her shaft. Returning to the lube I filled the palm of my hand and began stroking her cock up and down. I was really ‘greasing the pole’ and the results were quick and obvious; Miss Diane’s cock was stiff and eager. I wiped my hands, grabbed the desk, bent over, closed my eyes and gritted my teeth. Miss Diane placed some lube on my rose bud and inserted her middle finger to ensure that it too was well greased.

Miss Diane wasted no time and quickly had the tip of her cock in my rectum. I grabbed the desk harder and Miss Diane’s next thrust went in about four inches. “Ouch!” I exclaimed as I tried to relax my anus. On the next thrust she was in and set up a steady thrusting, going deeper with each forward shove. I clenched down on Miss Diane’s cock a couple times. Entering me as far as she safely could go Miss Diane held still, doing a flex-throb move of her cock that actually felt erotic to me. ‘So deep, so filling, so warm’ I thought. A moment later Miss Diane withdrew completely. “Clean me” Miss Diane ordered. I took the warm wash cloth and cleaned the cock that had just been in me. I took the liberty to take a new clean cloth and wipe the lube from my crevice. I tossed the cloth on the desk and went to get dressed leaving Jackie on her own.

“It’s your turn Jackie.” Jackie turned around and in a bold move dropped to her knees and began blowing Miss Diane. Taken by surprise Miss Diane held still. A few more slurps later, one slurp down to the red ring she had just placed there, Jackie stood up and said “You said make sure you were hard.” She then packed her hand with lube and greased Miss Diane’s shaft. Taking an extra glob of lube Jackie reached between her own legs and lubed her self. She smeared some into and around her rectum. Jackie turned, grabbed the table, bent over and spread her legs.

Miss Diane was right there and was five inches deep in just a few fucks and was at her maximum depth a few thrusts later. Miss Diane began thrusting very quickly and began grunting. She grabbed Jackie by the waist and pulled her back while thrusting forward. She held Jackie tight, at maximum depth. Jackie clenched several times. Miss Diane immediately ejaculated. Still holding Jackie tightly she squirted three times more. All motion stopped for about a 30 seconds. Jackie did a final ‘milking clench’ move and pulled herself clear of the offending shaft, squeezing it as tight as she could as she dragged it from her bowels. “Damn, you! You said you wouldn’t cum!” Grabbing a wet cloth she cleaned herself first and then used the same rag to clean Miss Diane. “I’m sorry Jackie; I thought I could control it. I’m sorry”.
Jackie stormed over to her purse, got out a tampon and shoved it home. She threw the wrapper and empty applicator on the shelf. She was determined to not be a butt drooler.

Jackie got dressed, grabbed her belongings, grabbed my hand and stomped out of the room. And that’s how Jackie got an extra score for taking it up the ass. The Rules said you get credit for anal sex if the partner cums inside of you. Miss Diane had cum. In fact Jackie had to insert a new tampon about three hours later.

The makeover

Jackie and I thoroughly enjoyed our makeovers. It gave us time to relax and compose ourselves. I’m natural a dirty blonde and went with a fringed pixie cut with some nice highlights; Jackie, being a brunette, opted for a longish shag with bangs and with hint of red. We had our brows waxed to perfection and the manicure left our toes and fingernails well shaped and a vibrant dark blue. None of our ‘class’ had that color. Our eyes, eyeliner and eye shadow, lips, etc. looked perfect! Lunch was soon and we were getting ready to leave.

The beauticians told us to relax for a little longer and brought out everything needed to wax our legs and other body parts. Jackie said “I don’t think so; this isn’t what we were told.” The head beautician said “We got instructions from Miss Diane that we were to do something extra and that you’d understand.” I started laughing and told Jackie “Sit down and enjoy the perks of having done someone a favor. You’ve become a wax whore!” We sat back and relaxed and watched the beauticians work their magic. Jackie reached over and took hold of my hand. Jackie looked at me and asked “I’d still like to ask her who of us is the tighter!” I retorted “You may have been tighter but I was the better fuck!” We both began to laugh. The two technicians looked at each other and agreed “Let’s give them the works”.

An hour later Jackie and Jenny left waxed and smooth in every area possible. I had never had a Brazilian wax before. The process and the smoothness were amazing. I knew that Stacie and Jackie would enjoy our smoothness eventually too.

I asked Jackie, “Pass me your new tube of dark red lipstick.” I applied the new shade and passed the tube back to Jackie. “The monogram looks classy.” We took time to put on our new garter belts and hose for the first time. I had them on in short order. Jackie struggled and I helped clip her garters to her stockings being sure to put panties over the garter belt. “Over, if you’re just going to work, makes it easier to pull down your panties and pee. If you’re going on a date then you put them under the garter belt as it looks sexier for your date.” I explained. Jackie wondered ‘How does she know these things’?

As we slipped on our two inch pumps I told Jackie that a good pair of four inch heels would make our legs look nicer. We unbuttoned the top two buttons of our blouses and turned to hug each other. The hug evolved into a few kisses with each of us giving a few good natured tugs on each others ‘training wheels’. We broke off our kissing and strode, hand in hand, into the dining area with our ‘goodie bags’. We could catch the last 30 minutes of lunch.

A final Chapter with a surprise ending is next.

(The final chapter has been posted since April and has the least amount of reads of all the previous chapters. The last few paragraphs explain how and why our main character became so 'girly'. It's actually a poignant revelation and ties up a very key element. That explanation begins in the paragraph entitled 'Revelations'. I encourage you to read the final reveal.)

"Revelations" is found in the next and final chapter.

“I have something I want to share with you. We’ve become special (and very intimate) friends as we’ve gone through the program. On more than one occasion you, and several others, have asked ‘How does she know about all these things?’

(Comments would be appreciated. Thank you.)

(This chapter has been posted since April 2018 and has the least amount of reads of all the previous chapters. The last few paragraphs explain how and why our main character became so 'girly'. It's actually a poignant revelation. That explanation begins in the paragraph entitled 'Revelations'. I encourage you to read the final reveal.)

Previously

As we slipped on our two inch pumps I told Jackie that a good pair of four inch heels would make our legs look even nicer. We unbuttoned the top two buttons of our blouses and turned to hug each other. The hug evolved into a few kisses with each of us giving a few good natured tugs on each others ‘training wheels’. We broke off our kissing and strode, hand in hand, into the dining area with our ‘goodie bags’. We could catch the last 30 minutes of lunch.

Lunch – Day 25 or was it 35... or maybe 40?

We were freshly fucked and freshly waxed. We approached the lunch table. The entire table of girls turned to look. Stacie and Tracie were already seated. Comments of ‘Wow’, ‘fantastic’ ‘damn, they’re hot’ could be heard. As we got closer Jackie made a point of lifting her skirt to show off her new garter belt and stockings. Her name embroidered on her garter belt was noticed by all. Jackie snapped one of her garter straps for effect, smoothed her skirt and sat down at the table. I sat next to her.”Look, they also have matching gold hoops and manicured, blue nail polish, finger nails just like Stacie and Tracie” said Joan. “These aren’t hoops; these are ‘training wheels’ I replied. Most of the girls looked puzzled. Stacie and Tracie smiled at the inside joke and winked at Jackie and me.

“What do you mean by ‘training wheels’? Damn, you both seem so beautiful and radiant” remarked Fannie. “Those stockings make you look so smooth”. “We were treated to a full body waxing; legs, eyebrows and then the rest of our parts. We won’t need to shave anything for quite a while. We had a Brazilian wax treatment. Having our pubic areas done felt weird” I announced. “We’ll explain about the ‘training wheels’ later or you can ask Stacie or Tracie.”

Fannie pressed further with “How did you get the extra treatment… who did you have to fuck?” Jackie looked around the table and said “Trust me, we earned it. I’m not sure that the results were worth what I had to pay.” She was smirking. “I’ll explain later” I said. Tracie ventured, “Rose will love her goodie bag as they toss in an eight inch silicon dildo… I figure her vibrator will need to go to the shop for repairs soon.” We all laughed.

Lunch was over and everyone was to go for session 18 of voice modulation… where we were being taught how to sound more feminine. Marked improvement was apparent in every one of us; speaking in a feminine sounding voice was becoming second nature. I made sure that Stacie, Tracie and Jackie held back for a few minutes. I wanted to compare notes with the two other girls that had been ‘interviewed’ by Martha.

“How did it go for you two? I see you also got goodie bags but did you have to give Martha a blow job? Did you have a tightness test? Did you have a chance to 69 with each other?” I asked. Tracie seemed surprised “What’s a tightness test? Whatever that is we didn’t do it. Yes, we had to suck off Martha but only I was allowed to bring her to orgasm. She had a hint of some flavor in her sperm that I’ve never experienced before. No, we didn’t 69 each other. I have to tell you, she was hung like a horse and was three inches big. My jaw is still aching!” Stacie chimed in, “Her garter belt was downright beautiful and I think the ‘training wheels’ are a cute idea. I can hardly wait to try them on someone.” She reached over and gave my hoops two gentle tugs.

Jackie replied with “First off, when Miss Diane is naked it looks like she has a snake dropping from her crotch. And she has some real girth too. We did the sucking thing. I was ‘lucky’ to get the ‘gift’ of her seed. I didn’t think I would be hungry for lunch because she came so much. Because Jenny and I were so damn horny she offered us her couch so we could finish each other off. I just think she wanted to watch. And it gave her time to recover from me draining her so she could do the bullshit ‘tightness test’. At least we can check off a couple things off our requirements list. And I get to check off one additional thing from the list.”

I piped up, “Before we could leave she told us that we both had to undergo a tightness test. She poked us both… made us put our hands on her desk, lube her shaft and bend over.” Tracie and Stacie looked surprised. “So why does only Jackie get to check off being fucked off of the list?” I rolled my eyes and hissed “Think about the rules you ditzy girls!” Everyone looked over at Jackie. “That’s how we got the extra wax job. Miss Diane was trying to make up for an ‘accident’. Accident in my ass! That reminds me, I need to swap out tampons. You ladies go ahead and I’ll catch up.” ‘My ass!’ That’s a pretty funny joke when it isn’t YOUR ass.

Jackie made it to the voice training and it was soon time for dinner.

Dinner

Nothing new or exciting. The enhanced femininity that the ‘special’ makeovers did for our appearances and deportment was noticed and appreciated by all. Comments about Miss Diane’s massive appendage and Martha’s girth were of great interest as was what a Brazilian wax feels like. I found my private parts being rubbed in search of stubble. Oh, the price of popularity!
Staff member Cindy brought out the most recent Score card. “Here ladies’ take a look. It’s time to pick up the pace. I’m also giving you the new dress code. It begins in two days. Your wardrobes will be updated soon.”

Score card #2

Oral --- Anal --- Vibrator

Rather than bore you (or brag) about everyone’s score, our count in all categories were dramatically higher than on our first Score Card. The special pharmaceuticals we have been consuming for so long were definitely making their presence know. Our inhibitions were almost non-existent and our libidos were off the charts. Thoroughbred stud horses are chaste by comparison to us. Life had evolved into a prolonged rutting season. There were no complaints. We were all skilled, and willing, male lesbians by now. We could start our own sorority!

As had become the custom, after a passage of time, the Program would increase their expectations of us. When we had become comfortable and proficient with a certain degree of our femininity the Program would up the ante. Pantyhose evolved to garter belts and stockings; Two inch heels became three inch. They wanted us to expand our girlishness. Toward that end we were given a new dress code after dinner.

************

New dress code effective immediately:

Everyone has progressed and so must your clothing. Heels will be an inch taller and their heels will be narrower. You’ve graduated from pantyhose to garter belts and real stockings.

Monday thru Friday lingerie: garter belts & nylon stockings (no pantyhose), boy shorts, French cut, thong or tap pant panties.

Monday thru Friday clothing: Dresses with a hem six inches, or less, above your knee. No skirts.

Weekends: short shorts with an inseam of 5 inches or less, leggings, mini skirt, sun dresses, one piece rompers, skirt and blouse, skorts with 5 inch inseam maximum, crop tops

At all times: complete makeup including lipstick, mascara, eyeliner, eye shadow, perfume, earrings, anklet, necklace, no less than one bracelet, 2 rings minimum, push up bra, with enhancements, that are at least a B cup (enhancements waived when you reach a natural B cup or larger).

Nail polish: Toes and finger nails must both be painted. Blue and other colors other than red are now permitted. Take advantage of the nail salon we are now providing.

Footwear will now have 3 inches heels: Kitten or pump heel styles. The wider court shoe heel worn previously is no longer an option. It’s time to learn to walk in real heels like other women. Your new shoes are in your room. Be careful.

Hair: No more wigs. Your hair is long enough to be styled. You’ll be scheduled to the beauticians soon. Layered bob, various pixie styles, bangs are some of your options. Check out the Dolly Parton options. Pony tails or longer hair styles when your hair length allows it. Beauticians are available for you on the weekends and will help you select highlights or hair color.

Sleepwear: Just as before - baby dolls, satin pajama set, Shorty night gown or a chemise. There will be no sleeping in the nude.

***************

The days were all the same yet different at the same time. The learning was constant and so was the sex. Intimate details and techniques were shared.

Breakfast a few days later

Immediately after breakfast I was summoned to Miss Diane’s office and Jackie was told to report to Martha’s office. It was another ‘special’ one on one evaluation meeting. As before sex acts were required of us. About three hours later we met, by chance, at a pair of beauty chairs. Jackie noticed that Jenny’s gold necklace was now sporting a diamond on ring. Seeing this Jackie held up her necklace and wiggled a similar ring on her necklace that held a ruby. As we were sitting down Jackie asked “Leg wax?” I slight grinned and said “Nope, another Brazilian.” “Jackie leaned over, and in a loud whisper, said “Me too!”

As we were being attended to Jackie said “Nice ruby earrings.” “Yeah” I replied, “Those pearls look good on you.” Continuing, I quipped, “Do you know what this means since it came from Miss Diane?” pointing to my new rubies. I grinned and said, “It means I’m a better fuck!” That gave us a good laugh.

Everything had been waxed smooth, pubes, eyebrows, armpits and legs. We were minutes from getting out of the chair when Matron came in. She had what appeared to be a lunch box in her hand. “Please remain seated ladies. There’s something I want to give you both. You ladies have excelled in every category. It is my pleasure to give you each a second ear piercing.” While reclined the Matron inserted the proper stones in her gun and shortly we had two additional gems ear studs just above where the initial holes were. We both had ruby AND pearl earrings; dual piercings. We both exited our chairs and stood.

Displaying the most emotion we had ever seen, Matron gave us both a polite hug. Matron cupped each of our breasts and gave them a significant fondling. Nipples grew rigid. “Before I leave I have new C cup balconette demi-bras for each of you. It’s obvious that you need them. I hope you like peach color. Victoria’s Secret of course. Additional new bras are already in your dressers. Hand me your old bras, please.” We, by now were so well practiced in donning and removing our bras, that we only need one hand to reach behind our backs and snap out of our bra’s. We hung the old bras on the beauty chairs and put our arms into the new ones. Matron made sure to personally hook them up. She gave our straps a playful snap and gave us each a butt rub. If I didn’t know better I’d think she was hitting on us! “Good luck.” Matron turned and left.

Lunch

Arriving at the lunch table late, because of our ‘beauty’ session, it was quickly noticed by the others that we both were double pierced and had new gem studs. We received a modest round of applause. Jackie piped up “Yes, we both got waxed again… in more ways than one!” “The things a girl will do just to get a free wax job” was tossed out by Joan. “Sure hope your knees aren’t sore” was Tracie’s comment. “Better not leave a puddle on the bench” said Rose. There was a lot of good natured finger pointing (some middle fingers to!).

Weeks became months

All the months we have been held should not to be construed as a raging fuck fest. Actual learning took place. In addition to the carnal aspect The Program also offered classes that included: Sociology of Sex Roles, anti-discrimination training, anger management, contributions of women in science and business, famous female inventors, gender sensitivity, female voice training, and a variety of similar courses to aid in our enlightenment.

To help provide the girls with a more feminine sounding voice, Adam’s apple reductions and tracheal ‘shaves’ were provided to the ladies that wanted them. No one turned them down. Additionally, The Program would provide us all with new State ID cards, with a photo of our newly feminine selves, so we could cash checks, travel and get on with our lives. The IDs would indicate gender as male. We would not be allowed to leave until our new IDs arrived. If anyone wanted to make ‘the final leap’ and transition to a fully functioning female that was up to each girl. We four wanted to remain ‘Chicks with Dicks’.

Mannerisms, deportment, attitudes and sex had become automatically feminine. Some did prefer to be the ‘bottom’. Hair styles, makeup and clothing choices became more sophisticated and sexy. Blow jobs became increasingly superb. Most of the girls had adopted my tampon technique even when there had been no sex.

They ‘Fabulous Four’ had decided to get matching ankle tattoos when we got out. We decided on a delicate, but colorful, humming bird. We were anxious to have them soon.

We ‘fledglings’ were trying out our ‘wings’. Somewhere, over the months, I had my shoulder length hair dyed platinum blonde, Jackie went red head. She really looked hot. It suited her well. Our ‘fluttering’ and desire to fly free had increased. We all were nervous. It would soon be time to leave The Nest. Key decisions had to be made.

Leaving the Nest – post breakfast

Our entire group of ladies would be leaving The Nest at the same time we were told. We all had ‘graduated’. Perhaps the threats of being held longer were false; perhaps a new group of trainees needed our space. It didn’t matter. We were all going to be able to resume our previous lives… if we wanted too. All the details would be told to us at any moment. WE were waiting for our new State IDs to arrive.

Leaving the Nest – post lunch: the IDs arrived!

A make shift living room had been put together a few weeks ago in the corner of the dayroom. It consisted of two coffee tables, eight chairs and some side tables. A large Persian rug and a couple of lamps completed the area. It was a comfortable place to kick your heels off, put your feet up and relax.

Stacie and I walked into the dayroom having just consummated our need for each other. We both were smiling ear-to-ear and were proudly holding our new State ID cards. We made our way over to join our friends, Jackie and Rose, who were already relaxing in the corner lounge. We plopped ourselves into a chair.

‘So what are you going to do now?’ was the topic among the Fabulous Four.

Rose began. “I know I don’t want to go back to living as a male. Maybe I’ll go back to school. Based upon my experience here speech pathology or audiology seems interesting. I would be helping people. It would be better than a boring office job.”

Stacie piped up next. “I really don’t want to go back to an accounting job. I was hoping to open a bed and breakfast place or maybe a transitional safe zone for wayward or troubled young cross-dressers. Jenny and I have thought about going into business together. We certainly have the experience!” We all chuckled and nodded our heads in the affirmative. Stacie continued. “Before I came here I had a few acquaintances… now I feel I have three good FRIENDS.” We paused and let that concept sink in. It was a touching moment. “What about you, Jackie?”

Jackie took a moment to think and flipped her hair back in a most feminine way and began her story. “For some strange reason I like this place. Not at first, but it has brought some order to my life and it put me in touch with my feminine self. For that I will always be grateful. I have heard that Martha is leaving The Nest to join her girlfriend somewhere in California. Hollywood area I think. I’ve already made a formal application with Matron. I think I could really help the new ‘girls in training’ headed our way. It would also provide an income, a roof over my head and a source for some beautiful clothes. And of course there might be some ‘tightness tests’ to administer.”

The girls turned their heads toward me and waited for my response.

I had been subconsciously playing with my double earrings. “I’m inclined to go along with Stacie’s idea. I think there’s a real need for a user friendly transitional environment. Younger cross-dressers are lost and confused. I think Stacie and I could help them get through a rough spot in their lives. In terms of adult cross-dressers I think we would get a LOT of referrals from The Nest, especially if we had someone on the inside.” I winked at Jackie and continued with: “For me it would be a labor of love. We could take advantage of the halfway housing offered us by The Nest which would save us almost a year’s rent. We could apply the amount we saved to our new business. Maybe The Nest would help us get it up and running, rent us a place on their compound.”

We four smiled at each other and leaned forward to grab hands, making a friendship circle. We held our grip awhile and with a final squeeze, let go and leaned back in our chairs. Contentment seemed to ooze from us all. A couple minutes went by and I loudly cleared my throat. I wanted their full attention.

Revelations

“I have something I want to share with you. We’ve become special (and very intimate) friends as we’ve gone through the program. On more than one occasion you, and several others, have asked ‘How does she know about all these things?’ Two things in particular: my use of tampons and how I made crotch control panties from old pantyhose. Do you remember? “I sure do!” said Stacie. “I wondered where you got your expertise with eyeliner.” “There were a few other things that seemed odd” tossed in Jackie. I softly giggled and leaned forward in my chair to continue.

“My father taught me everything I know about make-up, lingerie and women’s clothes, and with my mother’s approval! Dad had been a cross-dresser since he was five or six. When I was four or five he’d sit me on his stocking covered knee and I’d watch him apply his make-up or nail polish. I would play with all his tubes and bottles of lipstick, nail polish, perfume, etc. I’d say ‘gimme gimme’ and he’d apply a light shade of lipstick on me, paint my nails or maybe run a mascara wand on my lashes. I can still remember the delicious tastes and smells. He’d ask me to hand him his bra or hose and I’d go get them. Knowing what I now know those activities are considered ‘girly’.”

“Mom didn’t mind any of it. She used to help dad with his dressing and make-up sometimes and eventually with me. In fact she gave me my first set of panties and a nylon sleep set for Christmas at age five; she gave me my first makeover at age seven. I’d started dressing as a girl at home at age six. They had my ears pierced at ten. I was wearing stud earrings in public then. At home I wore hoops or chandeliers and I always wore them on long car trip vacations. I still love their feel on my cheeks. I always wore age appropriate girl clothes and looked forward to birthdays and Christmas.”

“Mom was the one to show me how to properly shave my legs and it was dad that rolled my very first set of nylons up to my very first garter belt. It was our family secret.” I took a deep breath, leaned back in my chair, took a sip of water and continued.

“Mom was a would-be artist, painter and poet and thought that all the femininity would inspire my artistic side. Dad was a mid level office manager and always shaved his legs, wore lingerie under his suits and sport jackets. He taught me to wear an A cup starter bra under a T-shirt in order to go unnoticed. Shear, ‘nude toe’ hose and nylon tap pants were natural to me. We just never spoke about it or flaunted our ‘hobby’ to anyone.”

“Sex was never a part of any of this. I did learn, personally, how lingerie can cause erections and ‘wet spots’. Dad showed me the advantage that a panty liner provided. I know you’re wondering about my knowledge of tampons. I think it was when I was fifteen. I had been diagnosed with a severe form of IBS and diverticulitis. I was having problems with anal control; rectal leakage was a problem. Mom came up with the tampon solution. The thin panty liner Kotex, with wings, was dad’s inspiration. I have used them both frequently. Two years later I didn’t need either of those items but I was fully experienced in their use. I remember being extremely embarrassed when I lost the string to my tampon once. I thought I’d have to go the ER to have it located and removed. It took both of my parents to find and remove it. Dad kept pushing it deeper! As a side note, should this ever happen to you, an enema or two should flush it out. “

“Considering all that I just told you I hope you can see the irony of me being assigned to this program. I’m pretty sure I have the high femininity profile The Program was looking for.” I began to softly cry.

I had stopped speaking and the girls went silent as they tried to absorb what they had just been told. Tears were running down my cheeks. Tears were running down everyone’s cheeks. It took a couple minutes but all the girls stood up and silently motioned me to rise. Stacie, Rose and Jackie stepped over to me and created a four person hug. We were all quietly crying. Rose was going through a lot of tissues. It was a very tender moment.

Stacie went for a solo hug and kissed me tenderly on the lips. “I knew there was something. Thanks for trusting us so much as to share this. I couldn’t have had a better roommate or a better business partner.” Giving me another smooch she stepped back and let Jackie have her own moment with me.

Jackie and I embraced firmly and enjoyed the personal kind of kiss that only a lover could give. Jackie wiped her own tears and then, while holding my head gently in her hands, used her thumbs to remove the tears from my cheeks. “Damn, I love you!” Jackie said. You would never be able to find a happier group of male lesbians anywhere.

In a remote video monitoring room Miss Diane smiled, shook her head and laughed.

Caught and convicted: “My name is Jenny now and because I was a good girl I now have the tits and State ID card to prove it.”

It's amazing what young men will do in order to NOT get committed to a hard core men's prison.

Days 1 – 14 = Pre-trial intake; the process begins

All detainees had (allegedly) committed crimes and affronts against women and had been sentenced to indeterminate sentences in a special prison diversion program to atone for the crimes caused by our toxic testosterone fueled ways.

The Program

“Respect, tolerance and appreciation of all things female will be deeply ingrained into you prior to your release back into society.”

Criteria for the diversion program included being ages 18 to 28, no inclination to violence and being deemed ‘salvageable’ to the ‘correct’ way of behaving, mentally pliable and being receptive to the goals of the program. There were 12 of us at the beginning.

Upon conviction rather than being transferred to a harsh mainstream prison we would be diverted (transferred) to a Program facility that could deal with convicts like us. Avoiding a ‘real’ prison was our goal.

The Program was a comprehensive forced feminization and attitude modification program. We were to literally ‘walk a mile’ in the high heel pumps and bras of the females we had reportedly victimized and/or abused. We were ‘girls in training’ and expected to evolve to looking, sounding, thinking, dressing and behaving like women before being released.

Development of secondary sex characteristics, mannerisms and attitudes of women were crucial parts of our reeducation and release program. The term ‘progressive feminization’ was used a lot. We would be held in a secluded jail for several weeks prior to a “trial”.

Feminization began immediately upon arrest. We were required to shower and shave our legs and armpits; it was a large communal shower. It was an odd sight to see so many naked men sitting on shower benches and carefully shaving their legs; spontaneous erections popped up on a few of us. Smoothly shaved legs feel erotic if you’ve not experienced shaved legs before. In the weeks ahead we’d find that nylon stockings and silky panties enhanced that those stimulating sensations.

Mandated wardrobe

Outerwear was a drab 1/2 sleeved blue print prison shift with an elastic waist band; the hemline was knee high. White cotton ‘granny’ panties and white satin, lace trimmed camisoles with one inch shoulder straps was our underwear. Black opaque tights served as socks. Black ballet style shoes with one inch kitten heels were to familiarize us with eventually walking in higher heels. The degree of progressive feminization in store for us was beginning to hit home. Our image was becoming girly.

We became aware of the feeling of vulnerability and draftiness that wearing a dress entails which is exactly what the Program intended.

Inoculations, ‘vitamins’, testosterone blockers, hormones, hypnosis sessions, subliminal messaging, libido enhancers and anti-anxiety drugs began on day one. A sedated prisoner that has also been subjected to subliminal messaging is more compliant and less trouble than a non dosed prisoner. Facial hair growth slowed significantly while hair growth on our head increased; haircuts were forbidden until release. We were assigned a communal dorm room that had a single communal shower. Sundays and Thursdays were leg shaving days; we routinely saw each other nude.

14 days of exams, tests and indoctrination

We were subjected to detailed psychological and medical exams which included a full body cavity search and digital prostate milking to obtain semen samples. While we held a plastic cup to catch the specimen a technician wearing a lubricated thin rubber glove penetrated us and stroked our prostates until we involuntarily ejaculated; sperm motility was being measured as was the elasticity, tightness and gripping power of what they called our ‘boy-pussy’.

Perhaps it was the libido enhancers kicking in or the hypnosis but being digitally penetrated was an odd yet satisfying experience on many levels. I and most of the others began to look forward to our weekly prostate exams; there’s no such thing as a ‘bad’ orgasm.

Our height, weight, chest size, waist, inseam, penis size, shoe size and other measurements were dutifully recorded. It was like going to a tailor to be fitted for a custom suit.

Every day in pre-trial confinement allowed the drugs, subliminal messages and mental conditioning to take effect.

Day 15 - The “Trial”

If you were pulled before their tribunal your fate was already sealed; that’s why our medications and psyche sessions began immediately upon being arrested. Even if you were found “not guilty” you would be subconsciously changed forever. One day you have a life and the next day you just disappear… for an indeterminate period of time. No hope of rescue. No recourse. The only ‘course’ we could expect was intercourse because our lives were now fucked.

There was no jury, only a panel of three cranky, bitter, old women with dry vagina syndrome who were charged with implementing a controversial prison diversion program for non-violent young hoodlums. The Program was a severe behavior modification pilot program called Total Immersion Therapy (TiT). The twisted irony of the acronym is that detainees could not be released from The Program with less than C cup sized breasts.

The tribunal believed toxic masculinity was the cause of all wrong doing and aggressive behavior; ridding troubled youths of their ‘toxic testosterone’ would rehabilitate and reverse their unruly male ways. Becoming submissive and feminine were key elements of The Program. Castration: surgical, chemical and/or mental castration of detainees was perceived as the optimum solution in making bad boys into good girls.

We all were found guilty of being male and susceptible to gender reprogramming; we were given 5 injections within 30 minutes of our ‘conviction’; 2 of the injections went directly into our tits. The shots had a mellowing effect and undoubtedly contained anti-anxiety drugs in addition to female hormones. Facial hair growth stopped and our tits were becoming noticeably puffy and itchy. Our hypnosis sessions were designed to make us more receptive to cross-dressing and same sex intimacy.

Low frequency subliminal messages were broadcast into our dorm as we slept. Split second flashes of hidden images and subtle cues were imbedded in all videos we were shown. Absorbed at a subconscious level this technique would prove to be very effective.

‘Convicts’ were given mandatory reading materials to encourage the feminization and behavior that was expected of us. Frock, TG Life, Transliving and other magazines were very informative and very stimulating; erections were frequent as was the need for sexual relief.

Due to the hypnosis, drugs and subliminal messaging none of us were shy about solo or mutual masturbation; leg shaving days seemed to make the need for relief more urgent. Extra boxes of tissues were put in our dorm.

Day 16 - Post conviction – Progressive feminization began in earnest; we become accustomed to NOT wearing pants; wanting to shave our legs; wanting to look ‘nice’. We were being groomed to be dressed for success.

Our simple blue prison shifts were replaced with more feminine short sleeved, high waist, flared summer dresses with sweetheart necklines; our hemline was now six inches higher to ensure our stocking covered legs were fully on display. We became accustomed to the draftiness of wearing dresses; it was a reminder of what our future held.

Ultra feminine pink nylon tricot French cut panties were substituted for our bland cotton ‘granny’ panties; white 15 inch nylon half slips we were added to our daily wardrobe as part of our ‘progressive feminization’. Progressive feminization required wearing nail polish; ‘Cobalt Blue’ made our nails look pretty.

We were given a 3 pack of multicolored satin spaghetti strap camis and could wear the color of our choice; I liked the yellow cami the best. Our black opaque tights were swapped for sheer thigh-high lace-top stockings; they felt naughtily pleasant on freshly shaved legs and rubbed pleasantly as we walked.

Our 1 inch heel ballet shoes were upgraded to classic black peep-toe pumps with 2 inch heels that were designed to shorten our calf muscles and get us used to walking on our toes; the stockings made wearing heels easier. Our red toe nails were always on display.

Program compliance

Length of incarceration depended on the degree of program compliance while in custody hence the term “indeterminate”. Respect and empathy for femininity in general and development of the secondary sex characteristics and attitudes of women were essential. Other factors that affected your release date were: the degree of feminine intimacy you embraced, your submissiveness, feminine appearance, breast size, etc. Having a ‘C’ cup breast was required for release.

Despite fear of incarceration in a men’s prison 2 recruits was dismissed from The Program.

There were two weeks of post conviction tests, interviews, and evaluations; daily deep hypnosis sessions were very relaxing. The inoculations, ‘vitamins’, testosterone blockers, hormones, subliminal messaging and anti-anxiety drugs continued. Inhibitions against displays of affection and touching decreased.

The ‘Fabulous Four’ – John/Jenny, Steve/Stacie, Rod/Rose and Jack/Jackie

It was during the testing and evaluation period that I (John) became acquainted with Jack, Steve and Rod. We bonded easily and it gave us someone to talk to. The ‘Fabulous Four’ as we called ourselves talked about sports, cars, movies, school, jobs and our current predicament.

What’s your story?

One topic to help pass time was: ‘What was the most embarrassing thing about the process so far’?

Rod quickly spoke up, “The full body exam, especially the rubber glove up the poop chute freaked me out. I offered to jerk off but I think they wanted to finger fuck me.” Some of us nodded in agreement.

Steve volunteered, “The exam wasn’t bad but when they had me strip they saw I was wearing panties… er, they were my girlfriends and I had just left her. THAT was embarrassing!” The entire group laughed.

The group turned towards Steve and me. “Well, what are your stories?”

I volunteered, “Like Steve I was found wearing panties too…but mine were beautiful peach colored French cut beauties with just the right amount of lace. The only thing is that they were mine.” Nobody laughed.

After an awkward pause we turned to Jack.

“I feel stupid that I got caught. I wasn’t wearing underwear; I was going commando style. The prostate exam actually felt good; like the orgasmic dick-tickle feeling that slowly climbing a rope in gym class was like.” The other’s nodded in agreement to the rope climbing reference. I had the same pleasant sensations in gym class and with the exam. The other’s gasped in disbelief.

Our consensus was that no one wanted hard time in a prison filled with career criminals lusting after sex with young men; anything but that! We had been told that prison or The Program would be a real life changer. Prison was a scary place and is why we agreed to enter The Program.

Your ticket to ride – out of the blue and into the red

The night before being transferred we were each given a bottle of ‘Cherries in the Snow’ red nail polish; two bottles of polish remover and a bag of cotton balls were left in our dorm.

“Here you go ‘ladies’, you’re leaving here tomorrow morning. If you don’t want to be left behind remove your blue polish and re-paint your nails bright red; all ten of them. Red nails are your tickets out of this place. Be sure to bring the bottle with you as you will need it at your destination.” The aroma of polish remover filled the dorm room.

I was the first one with clean nails and was soon blowing on my pretty blue fingernails to dry my polish. A few boys were obviously struggling and I offered to help. I discovered that I enjoyed painting and drying the toes of Steve and Rod in particular; it felt erotically naughty to be femming up a boy. We were rewarded for my efforts with pleasant erections in our panties; Rod briefly touched my penis through my panties, leaned over and kissed my cheek. “Thank you Johnny” he said. Something in the Programs methods was obviously working.

I stood up, stretched and went to my bunk leaving Rod and Steve to work things out. I lay down and held my hands at arm’s length to admire my pretty nails. I closed my eyes and discreetly relieved myself of my erection under my blanket; I fell asleep to the sound of giggling young men unabashedly jerking off. The Programs mental conditioning efforts were effective.

Day 31? - a month of hormones, hypnosis and conditioning

I, (soon to be called Jenny), Steve/Stacie, Rod/Rose and Jack/Jackie and the rest of us were to be put on the jail transfer bus very early the next morning. The fact that our foursome had ‘bonded’ had been noted by our ‘guards’. Our friendship was to come in handy in the near future.

We are transferred

It was dark when we were awakened. We put on our dresses and heels and went to breakfast. Afterwards we ‘girls’ lined up to board the bus. Our painted toes were easily confirmed.

We were bound for an unknown far away location on a bus with blacked out windows. We were told we were in a very exclusive program and that we should feel damn lucky to not be going to a high security men’s prison. It was long trip with no stops. I repainted Steve’s and Jack’s and my nails to help pass the time. I was not surprised that when I blew on their toes to dry them they developed erections. Our bus was well stocked with boxes of relief tissues.

Halfway to our destination we were given a paper sack with a single ham and cheese sandwich on white bread, a single packet of mustard, six carrot sticks, a juice box and a packet of our daily medications. The prison bus was equipped with a restroom; a chain link security cage protected the driver from us.

Our bus arrived at our destination many hours later; we heard radio chatter directing the bus driver where to park. The ominous sound of a heavy security gate slamming shut behind was un-nerving; it didn’t bode well. We were in a flat remote area that had few trees; we had no clue where we were. Escape was not an option. We were ordered off the bus and told to form a line. Our only possessions were the clothes we were wearing and a bottle of nail polish. Boxes of our medical records, court files, personal effects and our previous girl clothes were given to our new facility.

We stood in front of a stark looking cement building that looked like a huge warehouse or secret government prison. Towering chain link fence topped with rolls of razor wire surrounded the huge compound. Two skinny windows were adjacent to the heavy a blast door type of entrance. A sign over the door read “The Nest”.

We were led inside to a large ‘great room’ that was the hub of the facility. One portion of the room was set up for eating with high school cafeteria looking table/bench setup. We could smell food being prepared behind closed doors in an adjacent cafeteria; the clanking of pans was unmistakable.

Another part of the room was configured as an assembly area with about 20 chairs, a huge flat panel TV and a podium for presentations. There were several long tables near the podium. Each table had large pink shopping bags on them. We were told to take a seat and wait quietly for instructions. We sat and nervously looked around our new home and wondered what was in store for us.

Hallways to rooms, administrative and medical areas radiated like spokes of a wheel from the great room. I nudged Steve and pointed to a sign with arrows indicating there were a beauty salon and a doctor’s office nearby. A pleasant looking lounge area that resembled a living room complete with carpeting, couches, chairs, coffee tables and reading lamps was in the corner of the room.

A huge banner proclaimed “Welcome Ladies”. Rod nudged Jack and pointed out security cameras high on all the walls.

In the Beginning

Eventually two attractive women with clipboards entered the room from a side door and walked over to where we and the pink bags were waiting. Each woman was intently checking us out and making notes on their clip boards. Both ladies were very attractive.

After a few moments a tall woman addressed our group. “Ladies, my name is Miss Diane; my associate is Miss Martha.” Miss Diane paused and gave us a stern visual inspection; Miss Martha took notes.

Making eye contact with each of us Miss Diane shouted at us. “Cross your damn legs like a woman when you sit! You have your legs spread apart like a bunch of retired drag queens trolling for a John! Nobody wants to see your ugly snatch! Our goal is to have you looking, acting and behaving like women! That was made abundantly clear to you. So do it or quit the program. Perhaps a few days on Ward C are needed?” Miss Diane had our undivided attention.

Gritting her teeth in anger Miss Diane took a deep breath and loudly ordered, “Everyone stand up!” We immediately did as she commanded. Calming herself Miss Diane continued.

“Watch and follow along as Miss Martha shows you what should become automatic to you every time you sit.” Miss Martha pulled out a chair and waited for Miss Diane’s instructions.

“As you sit always begin by smoothing your skirt under you with a brush of the hands. Then step back toward the chair, bend from your knees and sit.” We followed Miss Martha’s example.

“Now that you’re seated cross your right leg over your left leg at the knee, hold your thighs together without any gaps like Sharon Stone did in Basic Instinct!” We all were sitting like women. Miss Diane smiled.

“Ladies, if you had read the literature we provided you immediately upon your conviction we would not be having this conversation now; you would already know many of the things required of you. You damn well better read what you’ve been told to read; you’ll be better prepared for what is in store for you. Do you understand what I just said?” Miss Diane paused to let what she had said sink in. We nodded our heads in the affirmative, some of us answered with ‘yes’. Miss Diane continued her welcome speech.

“More explicit instructional literature and videos awaits you in your rooms. ‘Regiment of Women’ by Thomas Berger is mandatory reading; reading it and the other materials will help you graduate The Program.”

Miss Martha stood up and spoke.

“Proper feminine grooming, dressing, demeanor and sitting are essential for your eventual release. Electrolysis, vocal surgery, breast and nipple augmentation will be offered to those that want it. Never forget that no one leaves without Miss Diane signing off on their release. Never forget that I and the rest of the staff control your future, is that clear?” We all nodded and said, ‘Yes, Miss Martha.’

Miss Diane’s demeanor seemed to have lightened up. “I’ve been told that Jenny was the first one to finish painting her nails at the jail and that she helped several less enthusiastic girls at the jail and on the bus. Remember this; everyone needs a big sister and cooperation is rewarded.”

We had puzzled looks on our faces trying to figure out who Jenny was.

Miss Diane chuckled, “I got ahead of myself. Who is ‘Jenny’ you ask? Jenny used to be called John. From this day forward she is to be called Jenny.” A soft gasp came from our group.

“Let’s meet all our new girls. When you hear your boy name called raise your hand and listen for your new name; repeat your name and put your hand down. From now until your release you will respond only to your femme name.”

The process didn’t take long. The only delay was when Steve objected to being named Susan. Raising his hand Steve politely asked, “I would really like being named Stacie.” Miss Diane and Miss Martha looked at each other and said, “Sweetie, if you promise to be a good girl that would be fine.” Stacie smiled and said, “I’ll be a good girl Miss Diane. I promise.” A happy tear ran down Stacie’s cheek.

Recap: I, John was now Jenny; Rod became Rose; Jack became Jackie and Steve was to be Stacie. There also was Fannie, Beth, Tracie, Jewel, Mary, Joan.

Reality sets in – Day ??

Miss Diane called for our attention. “In addition to clothes there are other important elements to your transformation from bad boy to good girl; cosmetics, attitude, tits, counseling and a purse are just a few examples.”

As Miss Diane was speaking Miss Martha was handing out black leather purses to each of us; they were a medium sized convertible clutch/cross body combo; a shoulder strap was inside. A tasteful gold colored medallion reading “Nest” was imbedded on the side.

Miss Martha explained, “A purse is a ‘must have’ for every woman; you will carry one with you at all times when not in your room. Every woman’s purse contains lipstick, a mirrored makeup compact, tissues, a hair brush and a variety of other essentials. Additional necessities will be given to you as you progress. There will be occasional purse inspections to insure that your purse is properly stocked. Women wear cosmetics and so will you.”

Miss Martha paused for a moment to let her words sink in.

“And now we progress to a new element of your progressive feminization. Open your purse, get your compact and lipstick and color your lips. Everyone has the same color for now. Apply your lipstick and we’ll continue with your in-processing.”

Miss Diane chuckled at the struggle that some girls had in applying the bright red color and noted which girls had no trouble or reluctance at all. Jackie and I were the first ones done; Jackie winked at me to acknowledge my proficiency at lipstick application. The lipstick color matched our nails.

Miss Diane resumed control of the presentation. “Good job, ladies. Place your purse on your chair, form a line along the table with the pink bags, remove your boring denim jail dresses and strip naked. We have pretty clothes, shoes and bras for all our pretty new women.” The way in which Miss Diane phrased her comments about our situation was mentally emasculating. Several of us perked up at the reference to finally getting bras.

We made an unusual sight; 10 naked ‘men’, wearing 2 inch heels, cocks swaying, wearing red lipstick and nail polish. We looked around nervously sizing each other up waiting for instructions. In my opinion Jackie had the prettiest penis.

Miss Diane motioned with her hand and a rack of pretty tropical print puff sleeved sundresses were wheeled into the room; they were femininely short and would show a lot of leg. Our names hung on our specific dress. A cute yellow print dress caught my eye.

“Yes, girls, sundresses, garter belts, high heels and tits are the epitome of femininity.” Pointing at the dresses Miss Diane said, “You’ll soon be wearing one of these beauties; garter belts and perky tits are also in your future but not today. First let’s get you dressed.”

“Step forward, take the “welcome” bag that has your name on it and get dressed. Your new heels and first bra are in your bag.” Three of our group were visibly quivering and silently crying; Stacie was one. I wanted to comfort him.

Before we began dressing Miss Diane said, “As you put on your bras and camisoles take note of the puffiness, size and increasing definition of your areolas on your growing breasts; your tits and nipples will soon be the size of a mature woman and will require the comforting support of a bra. In the mean time you’ll have a basic B cup starter bra; sewed in enhancer pads will provide you with some cleavage; very soon theses pads will not be needed.”

We took our bags and began to dress; red high cut nylon panties with cute accent bows first, then matching half slips, followed by delicious looking sheer thigh high nylon stockings. In keeping with the progressive feminization we were given our first bra. It was a bright red lace trimmed push up; the B cup padding gave everyone the instant cleavage that Miss Diane had mentioned.

I quickly had my bra on; I hooked it behind my back like my mother used to do. Most of the others struggled and resorted to hooking their bra in front and then rotating it into position. Miss Diane duly noted my dexterity in hooking my bra. ‘How does she know this already?’ she thought. Fuchsia colored spaghetti strap camisoles completed our underwear.

“We look like the photos in the magazines that we’ve been reading” Tracie commented. “Based on the abundance of panty bulges I think we look very sexy” Mary added. Void of any inhibition Mary lowered her panty and displayed her erection. “Would you like to touch it?” she coyly asked. There were no volunteers. Program methods were again displaying their effectiveness. I smiled as I looked around to see who had the biggest bulge.

“Before you put on your new heels you need to put on your dresses.” Miss Diane pointed at the rack of dresses. “Find the dress with your name and get dressed; we wouldn’t want you girls to catch a cold.” All the dresses were the same style; the differences were pattern and color.

By luck the yellow dress I had noticed had my name! It was a beautiful tropical print short “flared” sleeve, high waist, ruffle hem that stopped 6 inches above the knee, V-neck and cute! I felt very lucky.

Our new shoes were classic black slingback pumps with 3 inch stiletto heels. We could feel the tightness in our calves and the arches of our feet but they, combined with our now defined breasts, definitely added to our feminine image. We looked fantastic. Knowing that under every dress was a turgid penis made the moment erotic; it was a ‘tranny fest’! I refreshed my lipstick because I wanted to. Erotic urges roiled through my groin; I was anxious to get to our room.

Miss Diane and her associate walked amongst us taking notes and checking for erections. Miss Diane seemed pleased.

Miss Diane called for our attention. “Settle down ladies! It was nice to see boys get excited about wearing pretty dresses. You’re beginning to look girly in your dresses, bras, panties, heels, lipstick and nail polish. Be advised that you will not leave here until you reflexively look and act womanly; until men are attracted to you and until YOU are attracted to men.” Half of our group gasped at her declaration.

“Put your old clothes into your pink bag and be seated; Matron wants to greet you before we allow you to have dinner! Be sure you sit like women. Sleepwear, shoes, cosmetics and hygiene items await you in your rooms.” We did as instructed.

A breakthrough in attitude

We sat, legs properly crossed and excitedly chattered like women at a wedding shower; we complimented ourselves on how pretty we were, how nice our lipstick matched our nails, how nice our new heels and stockings made our legs look, etc.: our collective attitudes had definitely changed. There was no embarrassment in wearing feminine clothing, nail polish and lipstick. We had become more effusive towards each other; cheek kisses, butt caresses and more had become routine.

Our short dresses made feeling each other’s stocking covered thighs easy. When Jewel began sensuously rubbing my inner thigh I did not deny her; I spread my legs. She had just cupped my bulge when an overhead intercom advised us to stand up and be quite. Miss Diane had been observing us; she gave me the ‘thumbs up’ signal, smiled and reached for her clip board.

Matron

A door off to the side opened and four very attractive women entered the dayroom. All were dressed like models about to go on a date. Their makeup, jewelry and fingernails were perfect; they wore four inch black leather pumps. A stern looking older woman appeared to be in charge. We were told she was to be addressed as ‘Matron’.

Matron had close cropped hair, wore basic makeup, black closed toe shoes with a 1 inch heel, a black cop “utility belt” that held a walkie-talkie and a taser. She wore a plain looking below the knee Navy Blue business skirt with a formal looking white blouse; she looked stern. The women that entered with Matron stood behind her with Miss Diane and Miss Martha.

Matron cleared her throat and began in a terse, strong deep voice to explain the program and what we should expect over the next months and possibly years.

Welcome to the Nest

“Ladies, this facility is called The Nest. It can be comforting or it can be harsh. The choice is yours. The Nest is an experimental rehabilitation facility. You are being held in a secret and remote location. Some ‘girls’ have been in The Nest for over two years.”

“We have a set of rules that you will abide by; there are no excuses. The amount of time you spend here is entirely up to you. To help you through the program you have been assigned a roommate. You will need each other if you are to survive and leave The Nest. If you don’t comply you don’t eat. We have harsher methods on Ward C to insure your full compliance to the program; methods that include castration and other procedures that you don’t want to experience. Am I clear?”

“No one in this group has an STD and no one is HIV positive. This will prove to be a big relief to you as you indulge in the intimacies required for graduation. As you know you were immediately started on female hormones and testosterone blockers to begin your feminization. What you don’t know is that libido enhancing medications and subliminal messages were also given that encourages acceptance of same sex intimacy.”

A collective gasp arose from our group.

“Because of your medications you will experience new urges and mood swings, your tits will itch as they develop and you will find yourself attracted to each other. You will be psychologically reprogrammed to live a better, crime free, feminine way of life. Take a close look at the lovely ladies behind me; they are genetic males.”

Some of us went pale as it became clear what was to happen to us all.

“As your passion and desire for intimacy and sexual release increase don’t fight it; follow through with your urges. There is no such thing as being gay in the Nest; we know that several of you began mutual masturbation before being transferred here. That is fine but never masturbate or be intimate during a meeting or class activity and always cleanup any mess you make.”

“Miss Diane, Miss Martha and the other ladies completed all phases of our program and could have left a long time ago. They have chosen to remain with us at The Nest to assist indefinitely.”

“To help you understand how this facility works think of The Nest as a school campus. I am the Principal and Miss Diane is Assistant; the other ladies are like guidance counselors and teachers.”

Miss Martha

Miss Martha was Miss Diane’s assistant it seemed. She too was very feminine, well endowed and dressed like she was going on a date. Low slung blouse, black patent leather pumps with 4 inch heels. Her lipstick was bright red just like ours. Her eyeliner and eye shadow appeared nice but a bit heavy.

Our group had not seen this degree of feminine beauty for many weeks. Some of us were clearly showing our appreciation in not so subtle, non verbal, ways; panties were beginning to bulge. This did not go unnoticed by Matron, Miss Diane or by Miss Martha. In fact Martha broke into a smile and took notes. The Program worked hard at making us hard.

Monitoring explained

“We use very advanced audio and video monitoring. You will be monitored and recorded 24/7 and that includes the bathrooms, hallways, toilets, showers, beds and dayroom.”

Their system also bombarded us with subliminal messages to reinforce program objectives. Split second flashes of hidden images and subtle cues were imbedded in all videos we were shown. Low frequency subliminal messages were also broadcast into our dorm as we slept; absorbed at a subconscious level their methods were very effective. All of this had a powerful impact on us and explained the desires I was experiencing; I was infatuated with two boys in our group.

Matron turned to her staff and told them to leave. “Miss Diane, I want you to leave too but you are to go to the video monitoring room and activate the recorders. Stay alert and send for help if you think it’s warranted. Make notes of all infractions.” Miss Diane immediately complied.

Addressing us again Matron said, “Familiarity with cosmetics, clothing, lingerie and high heels is essential for you to you fully understanding what women experience every day. You will also routinely shave your body and maintain your nails. From this point forward any time you pee you MUST sit down just like the women you will soon be. You have lots to read and practice in order to become the young women you agreed to become in avoiding prison. Reading ‘Regiment of Women’ and viewing all our in-room instructional videos will help.”

“I’ll now call names and assign room numbers. Get over your shyness now; it will help with what is coming later be more pleasant.”

“Jenny and Stacie, room one.” I looked around, found Stacie and immediately took her hand in mine; her hand was clammy. “Jackie and Rose, room two. Beth and Tracie room three, Fannie and Joan room four and Jewel and Mary are in room five. Each room has just one shared double bed to promote cuddling; you will become very familiar, and perhaps intimate, with your roommate.”

“You’ll find a variety of outfits, clothes, sleepwear, lingerie and instructions on your bed. Your walk-in closets have been well stocked with additional women’s clothing, shoes and very cute rompers for the weekends. You’ve been provided with a wide variety of skirts, blouses and dresses to familiarize you with mixing and matching a woman’s wardrobe. What you wear, unless we specify a certain outfit, is up to you. There are no pants.”

“Your chests of drawers have been stocked with panties, bras, stockings, etc. Bathroom medicine cabinets are fully stocked with feminine necessities including enemas, douches, tampons, panty liners, razors, etc. Vibrators and extra AA batteries are in each night stand.”

“Your dual vanities are fully stocked with cosmetics, brushes, nail polish and related necessities. An assortment of costume jewelry such as necklaces, bracelets, anklets and rings is in every room; feel free to accessorize when the mood strikes you. Ladies wrist watches are on everyone’s pillows; wear them!”

“Although you have been shaving your legs and armpits for several weeks first on your agenda today will be to shower and shave all hair off your bodies except your eyebrows and the hair on your head; this means your pubic areas… front, back, balls and butts. You’ll probably need your roommate to give you a hand.”

“Report back here in ninety minutes. A late dinner will follow. Afterwards you’ll go back to your rooms to get acquainted with each other; don’t fight your hormones or urges. Relax and go with the flow and your stay here will easier. You have ninety minutes. Dinner waits for no one. Go!”

We adjourned down the hallway towards our rooms. Stacie was three inches shorter than my 5 foot ten inch height; a perfect height differential for a boyfriend/girlfriend relationship. I recalled that when she was arrested that she, like me, was wearing panties. Unlike me she told us they were her girlfriends.

Our rooms are nice; our wardrobe is extensive

Each room was an oversized studio apartment with chairs, love seat, side tables, lamps, writing table, two dressers, two mirrored vanities, paintings and a 50 inch flat panel TV; a shared bed would insure physical contact and intimacy. There were no windows.

We had a spacious bathroom with a large walk-in shower that could easily accommodate 3 people, a tub, toilet (with bidet) and large shared walk-in closet already had the clothes we had been told about. A few outfits were hanging on the closet rods. We would select our own clothes.

A copy of ‘Regiment of Women’ by Thomas Berger and two boxed ladies wrist watches were on our bed pillows; vibrators were in the night stands of every room and a 50 page bound compilation of Big Closet stories was on the coffee table in each room.

Monitoring arrangements had been well thought out

Each room had high resolution cameras and audio surveillance equipment in the ceiling, in the bath room and over each bed. Motion and sound triggered them to turn on. Two-way observation mirrors were built into the walls.

Intercoms in the ceiling allowed the staff to make announcements and broadcast low frequency subliminal ‘Night Whisperings’ as we slept. Without our knowledge staff listened and recorded conversations and intimate moans of carnal delight.

We enter our room

I opened the door for Stacie and we entered our room. We stood there for about thirty seconds before Stacie broke down in tears. She was sobbing and trembling; I thought she may collapse. I gave her a compassionate hug to calm her down and began softly crying too. Together we cried and tried to digest what we both were going to have to endure. And we hadn’t even read The Rules yet. We kicked out of our heels.

Gathering a semblance of composure I broke our hug and held Stacie at arm’s length. “Hold on, Stacie. Calm down; it’s going to be ok. We can get through this together. We just need to work as a team.” I pulled Stacie into another embrace to comfort her and reflexively gave her a gentle kiss on her lips. Our three inch height difference was perfect so I kissed her again. Her reaction was to hug me tightly and passionately return my kiss. I felt her tenseness subside.

I looked around our room and retrieved a glass of water for Stacie. I guided Stacie to the love seat. “Here, take a sip; we’ll be ok.” I put my arm around her, pulled her close and caressed her hair; she rested her head on my chest. We sat with our eyes closed and relaxed. Her heartbeats slowed and became one with mine; I felt an attraction. Having our own room was cathartic.

After fifteen minutes of relaxing I picked up our list of instructions and we silently skimmed through them. New instructions would be issued as needed.

Instructions – key points

“All clothes and shoes were selected based on measurements taken after your apprehension. You will always dress completely in female clothes. This means panties, camisole, bra, skirt, dress, slip, etc. Footwear will have a 3 inch heel for now; nylon stockings, pantyhose or garter belts are mandatory. More casual rompers and tennis skirts WITH HEELS are allowed on weekends. Heels are mandatory at all times.
Become familiar with your make-up, clothing and feminine hygiene products. Your vanities are fully stocked. You will always wear make-up which includes mascara, lipstick, blush and nail polish.

There will be no sleeping in the nude. Sleepwear will be baby dolls, chemise or similar woman’s nightwear.
Shave daily and more frequently if needed. Douche at least twice a week.

Your purse is a key part of your femininity. You will carry it with you, fully stocked, at all times; it is to be fully stocked with cosmetics, compact mirror, hair brush and other female essentials. Purse inspections will be randomly done.”

When we had finished Stacie looked up and was about to burst into tears again. I stopped her by saying, “Shhh…don’t cry Stacie, this is easy. It could be much worse. You should shower and shave first. I’ll layout our clothes to save time. Call me if you need help in those… awkward places. We’re on a time schedule.”

Help me!

Stacie had only been in the shower for ten minutes when she called for help; there were two areas that Stacie was having difficulty with. Most difficult was her backside; she couldn’t gain access to her rear crevice. “Jenny, help me! Please” she begged.

I had no choice

I stripped naked, picked up the razor and stepped into the shower with Stacie. I sat on the built in bench and told Stacie, “Back up closer to me, bend over, relax your butt and spread your cheeks.” Stacie did as I asked. I used my fingertips to spread the shaving foam in her crevice; I circled and teased her soft opening.

As delicately as possible I made several passes with the razor. Her sphincter reflexively puckered with each stroke of the razor or touch of my fingertips; it was mesmerizing to watch. I was surprised at how clean and pretty Stacie’s ‘rosebud’ looked. I had a strong desire to kiss and explore her pretty pink pucker. I was panting with lust and had spread Stacie’s cheeks for better access to her boy-pussy when Stacie’s voice snapped me back to reality.

“Jenny, I need help up front too; I’m afraid of using a razor on my ball sacks. I can’t get the angle I need.” Before beginning my new task I leaned into her crevice and kissed her exposed pussy; I probed her virgin hole with my tongue and licked her perineum. Stacie moaned in delight and wiggled her pussy against my eager mouth; I fluttered my tongue and probed deeper. I had found a way to end her panic attacks. I ignored my raging erection and reluctantly focused on shaving her.

Stacie had rid herself of most of her pubic hair but there were areas that needed help. I remained seated on the shower bench, rinsed the razor and applied Foamy where needed. I gripped her wet shaft and took my time in shaving the base of Stacie’s cock, testicles and inner thigh; it was a good excuse to retain hold of Stacie’s erect dick. I had never held another man’s penis before. My own hardness was clearly visible. Stacy smiled at my dilemma.

My first cock

Feeling a penis engorge as you hold it is thrilling! Drug induced urges and desires engulfed me. I was finding it difficult to control my desires. The admonition, “Don’t fight your hormones…go with the flow” was strong in my mind; it was like I was in a lust induced trance designed to fill an inner need. I turned her and her penis around to face me.

I held Stacie’s smooth testicles in one hand and gripped the base of her shaft in my other hand; her erect penis was level with my face. I felt my heart rate increase as I knew I was about to become a cocksucker.

As is customary, based on the porn we had been reading, I looked Stacie in the eyes before kissing the head of her pretty wet penis. I wondered if my urge to suck her cock was a reaction to the programs methods.

I tentatively took two inches of her penis into my mouth exploring her corona and meatus with my tongue; Stacie stepped closer and gently slid her cock two inches deeper into my welcoming mouth. I closed my eyes and savored what having a cock in your mouth entailed; the texture on my tongue, the spongy yet rigid consistency, the subtle taste, the stretching of my mouth; her pulse and involuntary sex pulsations transferred directly to my mouth. I fantasized what the moment of ejaculation would feel like; I was anxious to taste what she had to offer a cocksucker. As if in a trance I moaned with forbidden desires as I slurped, sucked and tongued her penis.

I discovered that when I pressed my middle finger against her pussy Stacie’s dick would throb and momentarily expand in my mouth…so I did it again… and again. On my fourth tease Stacie wiggled and squirmed downward until my teasing finger was impaled in her up to my second knuckle; she gripped my finger with her pussy and made a delightful girly squeal of delight. I savored the feel, texture and erotic process of cock sucking; I anxiously anticipated savoring and devouring Stacie’s sperm.

Knowing that we were running out of time for Stacie to orgasm I probed for her prostate with my middle finger while increasing tongue and lip action on her rigid shaft; Stacie began involuntary thrusting her cock across my lips and tongue; she was face fucking me! Stacie’s penis began to throb.

Stacie let out a guttural, “Oh, my god!” She grabbed my head and thrust all seven inches of dick to the back of my throat and kept it there; she squirted several loads of her viscous sperm into my mouth. I sucked harder in an effort to drain her hairless testicles. Stacie slumped against the shower stall wall. I held still savoring her essence as her penis slowly became flaccid in my mouth. I reluctantly released her bountiful penis from my mouth, maintaining a mouthful of her cum that I swirled, tasted and swallowed. I felt satiated and content.

Stacie collapsed onto the shower seat next to me and put her head on my shoulder and closed her eyes. After a few post orgasm quivers she opened her eyes, smiled and gave me a passionate kiss; her tongue searched for leftover sperm.

Pointing at my erection Stacie asked, “What about that?” Reminding her that we were up against a serious deadline I reluctantly ordered Stacie out of the shower. “I laid your clothes out. Go dress. I’ll hook your bra if need be. Go!” Stacie bent over and gave my erection a prolonged farewell kiss and exited the shower. ‘Tomorrow’s another day’ I thought.

As Stacie was drying herself she watched in fascination as I sat on the toilet and masturbated to a much needed orgasm. It didn’t take long until I had a handful of warm cum dripping between my fingers and into the water below. Without any hesitation I brought my hand to my mouth. Stacie watched in amazement as I had my first taste of sperm.

Still sitting on the toilet Stacie leaned down and kissed me passionately. “Damn, that was so erotic!” She grabbed my open hand and licked the remaining sperm from my palm. I blotted myself and flushed; we both watched my pearly white ‘baby makers’ swirl down the toilet drain. “What a waste” she said. I washed my hands and brushed my teeth.

I didn’t know it but what I had done to Stacie’s pussy and cock plus my jerking off was videotaped; notes were added to our files.

I quickly showered, shaved and dried off. I straddled the toilet to complete my internal cleansing. My douche bag filled with Summer’s Eve Fresh Scent hung nearby. I inserted the bulbous nozzle in my boy-pussy and cleansed my bowels completely. Unknown to us was that female hormones had been added to all of our douche products; colonic absorption is very efficient.

I felt compelled to bugger myself and continued an in and out probing even after the bag was empty. The quick orgasm I sought did not happen. It was time to go. I made sure to thoroughly clean the nozzle and return it to the shelf for later use. “Damn, too bad they don’t have a thicker nozzle… and we need more douche” I said out loud.

All of this was noted by Miss Diane. ‘Subject Jenny has no hesitation in touching or sucking Stacie’s pussy and penis; Stacie did not protest being touched. Jenny engaged in prolonged douching and self anal penetration. She seems to be a very receptive ‘bottom’ in the making. I suggest increasing her estrogen and perhaps administer another dose into her puffy tits; let’s reward compliance. Additional and larger diameter douche wands are needed in all rooms. More douche for all rooms.”

Stacie was 90% dressed but as expected needed help hooking her bra. Although I was nude and still partially erect I adjusted her bra straps to correct length. Noticing that Stacie was obviously inspecting my tumescence penis I took the liberty of briefly kissing Stacie’s nipples to firmness. To my tongue’s delight her nipples become delightfully erect; the drugs were obviously working.

*********
Clarification: Our Program was NOT a non-stop raging Trannie fuck fest!
In addition to the carnal aspect The Program also offered classes that included: Sociology of Sex Roles, anti-discrimination training, anger management, dressing as a female, contributions of women in science and business, famous female inventors, gender sensitivity, female voice training, makeup application, bi-sexual intimacy & hygiene. A variety of educational and vocational courses to aid in post incarceration employment opportunities were offered.

The pharmaceuticals we have been consuming were making their presence know; our inhibitions were almost non-existent and our libidos were off the charts. We had evolved from being heterosexual virgins to being skilled cross-dressing cocksuckers and sodomites in a short period of time.
*********

Make-up

I applied my mascara, curled my eyelashes into a feminine look with an eyelash curler lying on our vanity. I effortlessly hooked my bra using both hands behind my back for the second time that night. ‘How did she learn that very feminine move’ thought Stacie.

As Stacie watched I dabbed a small dot of lipstick on my check bones and created a ‘poor girls’ blush by blending the color to accent my otherwise pale face. “Blush on a budget” I said. “Very effective” Stacie said. ‘How DOES she know this?’ she thought.

I looked into the vanity mirror and checked my appearance; I re-blended my blush to tone it down. “Not too bad” I thought. I motioned Stacie’s to sit at the vanity. Stacie’s only problem was using the mascara wand. Again, I came to the rescue; I even used the eyelash curler on her. “Don’t worry you’ll get the hang of all this quickly enough” I said. Before I let her go I repeated the ‘lipstick blush’ on her. “It comes off easily with cold cream.”

My bra fastening and makeup moves were duly noted by Miss Diane: ‘Perhaps we have a ringer in our group. Jenny seems familiar and at ease with many aspects of feminine dress and cosmetics; she certainly is not adverse to same gender intimacy’.

Dinner in 15 minutes!

Glancing at the clock I saw we had fifteen minutes to make dinner. We put on our ladies watches and gave each other a mini inspection; all seemed ok. Stacie mentioned, “I really like your cleavage. How did your bust get so big if all our bras are the same?”

I smiled and said, “All you need to do is hook your bra on the next tightest hook… also I cut a wash cloth into four pieces, I fold a piece a couple times and place it at the outer bottom of my bra cup and then do the same for my other cup; it pushes your breasts inward and upward. Use my leftover scraps tomorrow.”

This tidbit of info was picked up and stored by the room’s audio monitor. Miss Diane would listen to the audio byte and add it to her notes later. ‘Recruit Jenny is creative, helpful and experienced with bras and cleavage enhancement’.

We grabbed our purses, opened our door and were about to leave when I said, “Oh, shit. We almost forgot the perfume!” Grabbing a bottle off the vanity I gave us a light misting of perfume. “Damn, that smells great!” Stacie said. We both read the label; ‘Cashmere Mist’. “Let’s not forget the name” we both said in unison. We giggled out of nervousness and the irony of the situation.

The first inspection & dinner

Stacie and I were the first to arrive in the dayroom. We took a seat and nervously fiddled with our purses. There were still four minutes until the deadline. Jackie and Rose were the next to arrive and were followed closely by Fannie and Joan. Beth and Tracie just made the cut. Jewel and Mary missed the deadline! As a group those of us that were in the dayroom took a deep breath. We were grateful they we were not Jewel or Mary. No excuses.

The Matron and Miss Diane arrived at the appointed time. A roll call was taken. Jewel and Mary were heard running toward the dayroom. “Miss Diane, please lock the day room door. The two slackers will be diverted to a different and not so pleasant program on Ward C.” The sound of the hallway door locking was like the sound of a prison cell door being slammed shut.

Mary and Jewel began knocking on the now closed and locked dayroom door. Their knocking increased in volume and desperation. “Miss Diane, please pull the door shade down.” The shade denied letting anyone to see in or out of the door windows. As the knocking continued Matron used her walkie-talkie; “Security, code red. Remove two new girls from the dormitory hallway. Take them to ward C. Do it now!” she said. The knocking and pleading ceased a few moments later. There was a muted scuffle, pitiful wailing and then silence.

We lost 2 girls

“Thank you for being on time. We have a lot to go over in a short period of time and will not tolerate non-compliance with Program rules. As you know The Program involves physical and mental changes. Your male mannerisms and voice modulation will be scrutinized and modified as needed. There will be on-going training and behavior modification classes. Your testosterone fueled anti-female masculine attitude and disrespect for women will be erased from your brain AND your testicles before you are allowed to leave The Nest.”

“For difficult inmates forced surgical castration, permanent makeup, breast augmentation, hormone implants and other medical procedures on Ward C are an option of last resort.” Pausing for effect Matron scanned her captive audience before locking her eyes on me. She continued; “Of course cooperative girls may request these enhancements if she desires them.”

Matron makes introductions

“You all have met Miss Diane and Miss Martha. My other staff members are Miss Cindy to my left and Miss Rhonda to my right. They are all part of our Mentor and Monitor staff. Every set of new girls are assigned a staff member. Mentors are available to everyone who asks; your confidentiality is guaranteed.”

We did not know but by sheer luck and good fortune we would find that Stacie and I were assigned to Miss Diane.

Miss Rhonda addressed us. “Each room has an instructional TV. Our channels cover hair and make-up; how to conduct your selves as women in terms of walking, talking, posture, mannerisms and, as previously mentioned, love making and hygiene techniques. It’s crucial that you watch all videos in their entirety; they and the low frequency subliminal messaging will aid your development; your viewings of our videos will be tracked.”

“Your release requires intimacy with the other girls in ways that may be new to most of you; your meds will help you be receptive.” Turning to face Stacie and me she said, “As some of you have already discovered same sex intimacy is very pleasurable. One of our TV channels covers this in graphic detail. Your room doors remain unlocked; you are free to cum and go between rooms.”

Miss Cindy spoke; “Today’s clothing and makeup requirements were very lenient. Tomorrow stockings, eye shadow and mascara are mandatory. Little by little you’ll be required to increase your femininity; progressive feminization.”

Earrings

“Tomorrow morning in order to increase your visible femininity your ears will be pierced and you’ll undergo salon treatments and perhaps a few other feminization surprises. It’s quickly done with a special earring piercing gun. Eventually you will receive voice training which may include voice feminization medical procedures. Electrolysis will be offered in the future.”

“Upon your complete feminization, and prior to your release, graduates will receive a State ID card reflecting your new feminine image and perhaps a new gender. SRS and other feminizing procedures will be offered to grads but is not mandatory. After release you may return to your old male world or you may choose to continue life as a female or a male that dresses and acts like a woman; in either case your mindset and physical image will be undeniably feminine. You’ll find the ID card very useful in daily life.”

Matron explains today’s inspection

“Here’s what we are checking for now: Are your legs, face and body parts cleanly shaven; legs, armpits, genitals and boy-pussy; no stubble anywhere. Smooth legs but a hairy butt is bad. Coordinated makeup, painted un-chipped nails, clothing, bra, panty and purse.”

“Jewel and Mary are no longer with us. The only thing they did was bitch and moan; they were unfocused so they failed. They will remain on Ward C until their stitches are removed.”

“Now then, shall we start the inspection? Miss Diane, you take the backsides and I’ll take care of the front side. Bring your clipboard.” Miss Diane snapped on a pair of thin blue latex gloves.

“Stand and as we walk by show your arm pits and fingernails to me and then pull down your panties and bend over and show Miss Diane your pussy and legs. Once Miss Diane pats your ass you may then be seated.”

While Matron inspected our front Miss Diane started a slow walk behind our group. She ran her hands over every recruit’s legs and checked everyone’s boy-pussy; I’m positive she fingered my pussy! I smiled and sat down. There was very little to complain about: A lipstick smudge or two, imperfect mascara application, 5 o’clock shadow; trivial things.

“Some of you need to shave your face twice a day; it’s not easy being a woman. Jenny, your legs and pits are smooth; making your own makeup blush is commendable; you also helped your roommate. We like to hear of roommates helping each other.”

Matron and Miss Diane whispered between themselves briefly. Miss Diane nodded her head and smiled.

“Adjourn to dinner and meet back here in an hour. As you noticed there will be no excuses for lateness or program infractions. Enjoy your dinner.”

Dinner

It was a late dinner, as promised; it was filling but institutionally bland. Beside every plate at every meal was a small paper cup with three pills; ‘vitamins’ we were told. Pill swallowing was monitored. If you refused the pills there would be no food. We were always mellower after every meal.

As I ate I chatted with Stacie but also tried to engage myself with the other girls. Jackie, at the end of the table, had piqued my interest; I remembered she had a pretty penis, appeared to be in good shape, and had Paul Newman blue eyes. Her blond hair made it even better. ‘I need to introduce myself’ I thought.

The general conversation at the dinner table was everyone’s fears and concerns of what the program was involved. The removal of Jewel and Mary also was brought up. Their removal from the Program had gotten our attention. What goes on in Ward C that requires stitches? Bilateral orchiectomy came to mind.

It was soon time to report back to the dayroom. We cleared our table and left for the meeting area.

The Matron explains

“You are free to return to your rooms and get better acquainted. I suggest getting a good night’s sleep. Do not neglect your reading. Breakfast will be at 8 AM sharp. Do NOT be late.”

Day 36? 46? -

A typical day: Breakfast, lunch and dinner interspersed with indoctrination speeches and explanations of the importance of following the Program. We had classroom training on makeup application and removal, female voice training, proper girly mannerisms, how to sit, how to cross your legs, etc. It made for a long and boring day for some of us.

Next day inspection - getting Stacie ready

We woke 90 minutes before breakfast and would do so until we found a morning rhythm and routine. We showered and donned our panties and bras. Stacie used my wash rag trick from yesterday to enhance her bust. Today’s requirements involved pantyhose and eye shadow which was no problem for me. I had finished my eye shadow and had my silky pantyhose on when Stacie asked for help. I patiently showed Stacie how to scrunch up her pantyhose like a donut, stick her foot into the donut hole and then easily roll them up her leg being sure to smooth any wrinkles. “The rolled donut method works the same with stockings and garter belts” I said.

As I watched Stacie try to master her pantyhose I saw a bulge in the middle of her panties that called to me. I reached over and traced her bulge from the bottom to the top. Her bulge seemed to be about six inches in length and emanated heat. “Where did THIS come from?” I jokingly asked. Our control top pantyhose minimized but did not eliminate boy-bumps.

Stacie blushed; “I couldn’t help it. I was looking how cute you look and was thinking about our shower yesterday and my erection began to grow!” I hugged her and pulled her closer. “No worries baby doll. In fact I’m flattered.”

I planted a kiss on Stacie’s lips and gave a comforting rub to her left butt and stepped back. Looking down at Stacie’s dress I saw her bulge was bigger. “We may need to get you some stronger control top hose or maybe a gaff.” “What’s a gaff?” Stacie asked. I explained what a gaff was and how they worked. Stacie was trying to process how I was so knowledgeable gaffs.

Eye shadow

I motioned Stacie to sit at our vanity. “This is easy. Pick a color suited for the look you’re trying for. Dip the tip of your little finger into the color you want and gently spread it over your closed lid. Some girls like to use a small sponge applicator or a special brush. Now you try it.”

Stacie decided on a light blue color and elected to use the small sponge applicator. It went on easily and Stacie gave a sigh of relief. “That was easier than I thought it would be; my eyes defiantly look prettier.” Stacie flashed a friendly smile and said, “Thanks for the tip.” ‘How does Jennie know these things’ Stacie wondered?

We both went to the full length mirror for a self inspection before leaving for the day room. Everything seemed to be correct. On impulse I opened the top button of my blouse; my cleavage stood out in a better way. Satisfied with our look we grabbed our purses and gave ourselves a spritz of perfume. Stacie opened the door and we headed toward the great room.

Fabulous Foursome

Stacie, Jackie, Rose and I had met when we were first incarcerated and became friends. We definitely looked different than we did a month ago; attractive and feminine. I saw Jackie walking down the hall towards us. In an attempt at humor I extended my hand in a ladylike manner. “Hello, I’m Miss Jenny and this pretty lady is my roommate Miss Stacie. I meant to say hello yesterday but life became hectic. How are you?”

Taken aback Jackie quickly recovered, stopped and did the demur feminine handshake. “I’m doing ok I guess, considering our circumstances. Are you ready for today?” Jackie absent mindedly scratched her left breast.

Sensing a bit of awkwardness Stacie cleared her throat, kissed me on the cheek and said, “We better be going Sweetie or we’ll be joining Jewel and Mary in Ward C.” Stacie’s was marking her territory.

We were the second group of ‘girls’ to arrive and immediately took a seat. I made a point of sitting between Stacie and Jackie. Stacie used a saliva dampened tissue and wiped her lip print from my cheek. The remaining girls arrived shortly. It was obvious they were experiencing tit itch too.

Subliminal audio & video messaging

As we waited the in-room videos became a topic of discussion. Rose asked if anyone had seen the video on intimacy yet. “You must watch it! It is so detailed and graphic. It’s a complete ‘how to’ guide on same sex intimacy; it gave me a raging hard on!” Beth spoke up and admitted that she and her roommate had also watched it. “It’s triple X rated and leaves NOTHING to the imagination! It made us so horny that we began experimenting; our orgasms were magnificent!” “Perhaps that’s the idea” I offered. We laughed and agreed to make viewing it a priority, perhaps as a group ‘movie night’.

Tracie volunteered that our reading material had made her so horny that she had to masturbate. “I would have taken care of that for you if you asked” quipped Jackie. There was another round of nervous laughter. Rose said the personal hygiene video was helpful. “At least I know what things are called and how to use them. I had never douched before.”

Matron, Miss Diane, Miss Martha and two other “girls” walked in. The room went silent.

Matron speaks – mentors & monitors

“Good morning, ladies we hope you got your beauty sleep as we have a busy day ahead of us. Today you will get your ears pierced and have a beauty enhancement day; you’ll definitely be prettier by the end of the day. On a lighter note it is time for breakfast. Go eat. You have sixty minutes. Be sure to take your vitamins.”

For weight control, breakfast, like every meal, was a half portion. Special ‘seasonings’ gave meals an odd taste. And of course there were the paper cup of vitamins. Conversation was diverse yet subdued. All too quickly breakfast ended and we started making our way back to the dayroom.

Jackie stopped as I was standing up. “Thanks for talking with me earlier. I really appreciated it.” Jackie gave me a hug and kiss. “Good luck today.” And then she left. Stacie looked annoyed. We made our way to the dayroom.

Pierced ears, eyebrow shaping and lip staining

We were all seated and waiting for instructions. We didn’t have to wait long. Miss Martha approached our group and announced, “Listen up ladies. With four beauticians working the entire process should take less than an hour. They will pierce your ears, insert training studs, and further beautify you by staining your lips a lovely, indelible, light red. Lip staining lasts a long time and proclaims your femininity 24/7 to everyone that sees you. It is NOT a substitute for your mandatory lipstick; it’s an enhancement and a constant reminder of your girly status. You may apply other shades on top of your lip stain.”

“Our beauticians will enhance your feminine appearance by shaping and tinting your eyebrows and tinting your eyelashes a uniform black. Brows are to be keep well groomed and shaped EXACTLY like we shape them today. Everyone has tweezers in their vanity. If you can’t do it right then ask your roommate to help. There are instructional videos on your TV. Remove your lipstick and stay seated until it is your turn. Reapply your lipstick when you return.”

Martha was right. Before an hour had gone by we all were back at the table. Some girls were twisting their ear studs, casually scratching their growing titties and carrying on subdued conversations. The main topic was how very girly our shaped eyebrows, stained lips and eyelashes looked. Joan nudged me and said, “It didn’t look like they used the piercing gun on you.” I smiled and replied, “No, my ears were pierced a long time ago and their studs slid in easily. I did get two injections direct into my tits; they said it was a reward from Miss Diane.”

“Your earring piercings will be checked for infection in a few days when we administer a special dose of hormones. You can expect to be a little moody, a bit emotional afterwards. These side effects are normal.”

Big girls need big purses

Matron, Miss Martha and Miss Diane came to our table.

“Miss Diane is passing out more items that will be a ‘must have’ in your purse at all times. These new items are in the zip lock baggie being passed out to you now. Your new ‘must haves’ are a tube of personal lubricant, two Lite Days tampons and two panty liners in addition to your regular things. A larger new style purse has been placed in your rooms. Big girls need big purses.”

Matron began an announcement

“In general you have all done well. Most of you are experiencing feelings, emotions and desires that you’ve never felt before. Enjoy your new breasts. Explore them; ask your roommate to explore them. They will bring you and your lovers much pleasure. As a reminder some girls may be called in for a progress evaluation or individual one-on-one counseling.” The staff left and we stood and meandered to our rooms.

Hooking up with Jackie?

Before reaching my room I saw Jackie and asked, “Would you like some company later? Stacie and I have talked about getting to know the others.” My heart beat went up at being so forward. Jackie smiled, “I’m OK with it but I want to ask Rose first.” Jackie reached over and stroked my cheek. “Look Sweetie, if Rose isn’t receptive right now maybe I could visit you guys. I’ll let you know at lunch.” She looked over at Stacie and said, “See you girls later.” Jackie and continued to their room.

I opened our door for Stacie. As soon as the door had closed we kicked off our heels, removed our pantyhose and flopped onto our bed to relax. “Whew, I’m glad to get those off!” Stacie said. I nodded in agreement. “I’m pretty sure they want us to experience and feel what women go through.”

After a few minutes I stood up, removed my blouse and went to the restroom to freshen up. I left my panties and bra on. As I bent over and began splashing water on my face Stacie came up behind and unsnapped my bra. I didn’t realize how big my tits had become until I saw them hanging and swaying as I washed.

Stacie makes a move

From behind Stacie reached around and gentle cupped both of my breasts at the same time. Stacie used her thumbs and forefingers to play with my nipples. My nipples were at full rigidity and stood out like pencil erasers. I didn’t want her to stop. Stacie said, “Your tits look and feel marvelous.”

I hung my bra on a towel rack and turned to face Stacie.

Stacie said, “We started something in the shower the other day… something we need to finish.” Stacie leaned forward and kissed my right nipple and began circling my nipple with her tongue. Stacie moved to my other breast and repeated the process. I groaned, closed my eyes and leaned back; the wash basin was supporting me. Having my tits and nips stimulated felt fantastic! A glorious erection began to form.

I pulled Stacie to me, wrapped my arms around her and unhooked her bra. “Lift your arms” I said. In the blink of an eye Stacie’s bra joined my bra on the towel rack. I reciprocated the pleasures that Stacie had just given me, sucking first one tit and then the other making her pulse race. My penis was popping out above my panties. Looking down I saw that Stacie penis was responding in the same way.

I leaned into her and made our nipples touch. I grabbed one of my tits and circled her nipples with my nipple. I had never done that before. Whatever drugs they were feeding us had to account for our high lust levels.

I was beginning to like cocks

I grabbed Stacie’s shaft through her nylon panties. Her penis poked above her panties so I took the opportunity and used my thumb to spread her pre-seminal fluid around the head of her cock. It was very slippery and wet; just the way I was beginning to like cocks. It was Stacie’s turn to moan.

Stacie pulled our panties down and let our shafts spring free. She thrust her pelvis forward until our cockheads were touching. Stacie leaned forward, kissed me and began to slowly masturbate me. As she stroked me she smiled and said, “There’s a reason that I douched this morning Sweetie.”

Grabbing me by the wrist Stacie pulled me onto our bed; we lay side by side. “I really want to thank you for the pleasure you gave me in the shower; it was fantastic! I never had my cock sucked before” Stacie said. While resuming stroking my cock she whispered, “Fuck me first and if I’m able, then I’ll fuck you, OK? I want to feel you cum deep inside me!” she pleaded. Her voice and eyes conveyed a lustful urgency; the pharmaceuticals were making her slut like.

I was reaching for the lube in my purse when Stacie stopped me. “No. No lube. I’ve got a better lube.” She flipped around on the bed and grabbed my stiff shaft. My cock was standing tall and proud. Stacie moved her grip to the top of my cock and stroked it lovingly; she stroked up and down my shaft, smearing my pre-seminal wetness with each stroke. I groaned and laid back.

Keeping eye contact with me Stacie pulled my cock toward her mouth. I was quivering in anticipation and my pre-cum was flowing. Stacie gripped my cock with her lips and sucked my shaft into her mouth as if was a thick piece of spaghetti. She swirled her tongue making my shaft as wet as possible. Sensing that the time was right Stacie stopped my blowjob. “I think you’re lubed up enough for me. How do you want to take me?”

Hot, horny, wet and wanton; Stacie gets fucked

I turned her question around; “How do you want to take it Precious?” I asked. “In the porn I’ve watched it’s good if you lie on your back and hang your legs over my shoulders.” In a split second Stacie was on her back with her butt on the end of the bed with her knees pulled to her chest. I stood between her legs with my feet on the floor; she placed the back of her knees on my shoulders with her legs hanging down. My wet cock was an inch from her boy-pussy.

Stacie grabbed my cock and rubbed it on her puckering hole; the hole I had kissed and licked last night. “That’s the spot” Stacie panted. She spread her cheeks and I pushed my penis two inches into her beautifully tight virgin pussy. Trying to be a ladylike about fucking her I paused to let her pussy muscle stretch; I wiggled my hips to help the process.

Stacie gave me an unmistakable glare of frustration and tersely demanded, “Fill me! I want you in me!” Stacie reached back, grabbed my penis and tried to shove my cock deeper into her: she succeeded. I took the hint, leaned into her and allowed myself to slide fully into her; Stacie gasped.

I tried to gently dilate her by partially withdrawing and then reinserting it several times before imbedding myself as deep as I could; pubis to rectum. I held still for a moment, allowing her to relax, and then sent her a penile throb in the hope that it would please her.

In return Stacie made a clenching rectal movement gripping my cock; it felt great and I couldn’t help but smile. Her clenching made my penis throb which is what I’m sure she was trying for. In return I moved my hips and wiggled my cock around deep inside her. It was Stacie’s turn to smile.

As Stacie’s pussy stretched wider I began a true butt fucking. I increased my tempo and Stacie raised her legs towards the ceiling; she moaned as my cock rubbed against her prostrate. “Argh!! Damn you, go faster!” I obliged. My toes dug into the carpet for leverage and my testicles beat a rhythm on the cheeks of her butt.

Stacie dropped her legs around my waist and gripped me tight for maximum penetration; I thrust as deep as I could and held steady. “Grip me!” I begged. Stacie made multiple rectal clenches and we both erupted. Stacie’s eyes rolled back in her head. She let out a loud yell, arched her back and orgasmed. Waves of my sperm squirted deep into my roommate’s bowels. Stacie’s seed splattered warmly on her mouth, chest and tits. “That’s feels so damn good, make it last!” she pleaded. Stacie made more rectal clenches which resulted in more ejaculations from me.

I leaned forward and sucked up the sperm puddles from her tits and used my finger to feed Stacie most of what was stuck to her face. She sucked my finger like a hungry baby sucks their mother’s tit. We were high on lust. We both exhaled and the moment was over. I held completely still.

Stacie dropped her legs and I began a slow withdrawal from my lover. Stacie clenched her sphincter muscles in an effort to retain me inside of her, which I greatly appreciated. Her tight anal muscle felt fantastic. ‘No wonder they call it ‘milking’ I thought. We laid there and let our bliss subside.

Stacie was completely spent and satisfied; a broad smile of contentment was on her face. “I could felt your warm sperm spraying inside my pussy.” She leaned over and kissed my sperm coated lips. We rolled over and snuggled in the classic spooning position; she was behind me. She pulled me as close to her stomach as possible; Stacie’s shaft rested on my butt.

Reaching behind me I lifted my butt cheek and Stacie’s turgid penis fell into my crevice. I released my cheek and it dropped, trapping Stacie’s penis like a hot dog in a bun; I felt its warmth. I had lustful visions of losing my virginity.

Giving her ‘hot dog’ a friendly clench I controlled myself and announced, “We best save our energy as Jackie and Rose may be stopping by later.” I glanced at the wall clock and immediately sat straight up. “Oh, crap. Lunch is in an hour and we need to clean up, get dressed and slap on some makeup or we’ll be late.” Based on Stacie’s reaction to being deflowered I was disappointed that I would have to remain a virgin awhile longer.

In Need of a “cork”

Stacie sat up. “Will you get me something to clean up with? I feel something wet leaking from my ass.” I tossed her a box of tissues from the night stand and said, “This will have to do for now. They really need to give us baby wipes. This is primitive! The least they could do is to provide us with panty liners.” Stacie did her best to clean herself and climbed out of bed. We had to get a move on.

I loudly laughed as Stacie waddled toward the bath room. She had wedged a couple of tissues in her butt crack and it looked as if she had a rabbit tail. Looking over her shoulder into the full length mirror Stacie saw the tissues dangling from her butt and began laughing too. From the video monitoring room Martha and Miss Diane broke into laughter.

Stacie earned her first tampon

Stacie sat to pee and tried, without success, to expel my cum from her bowels. She repeatedly wiped herself and muttered, “I’ll be getting a wet spot on my dress for sure. There’s no time to douche.” I pondered the situation and said, “You need a cork and I have a solution.” Reaching into my purse I produced a tampon and held it up for Stacie to see. “We have to go to plan B. When you’re done in there come here and I’ll get you squared away.”

I explain

Stacie pulled up her panties, washed her hands and walked over to where I was sitting and asked, “Ok, now what?” I replied, “Watch and learn. Tampons are skinnier than the vibrator, skinnier than me and they stop leaks. You peel open the wrapper, remove the tampon and extend the applicator rod to the ready position. The cotton tampon that stops your leaking is inside the plastic applicator tube and has a removal string attached to it.”

“The tampon remains inside the plastic tube until you insert it deep in your pussy and plunge the tampon out of the tube and into your pussy by pressing on the applicator rod. You pull the applicator out of you and the cotton ‘cork’ stays inside you blocking and absorbing any leaks.”

“See that white string hanging out of the end of the rod? It dangles out of your pussy until you pull on it to remove the tampon. It’s really very simple.”

I “cork” Stacie

“I’ll insert it in your pussy this time but the next one is up to you. We’re lucky that they gave us Tampax Lite Days tampons; they are skinnier than regular flow tampons. Now turn around, back towards me, drop your panties, bend over, and spread your legs.”

I spread a dime sized amount of lube to the top and sides of the plastic tampon applicator and moments later Stacie’s first tampon was securely in place; a small “mouse tail” string hung between her checks. I lightly tugged on Stacie’s dangling string to get her attention. “Did you feel that tug Stacey? Reach back, find your mouse tail and give it a gentle tug so you know where to find it.”

Stacie found her string and gave it a gentle pull. She was pleased that it would take a stronger pull to pop free. She pulled up her panties and continued with getting ready for lunch. Again Stacie thought ‘How does Jenny know these things’?

An emergency (social) gaff?

Stacie and I were ready. New hose, clean panties, proper lipstick, a fresh coat of mascara, curled eye lashes, correct jewelry and a hint of perfume. I took the extra time and added her eyeliner. She looked femininely perfect.

Stacie had tossed our old pantyhose into the trash. She was surprised to see me retrieve them, cut the legs off and keep only the panty. “What in the world are you doing!?”Stacie asked.

“Remember how our crotch bulges sometimes show? If we double up on the control part of the pantyhose it will be less obvious. Just pull them on like an ultra thin girdle; it’s easier than tucking, taping or wearing a gaff.”

Tuck? Tape? Gaff? ‘What in the world is the girl talking about?’ thought Stacie. ‘The use of an extra control top is pretty damn clever; actually brilliant.’ How does she know these things?!

Our monitors had lots to write about.

Lunch

Lunch was the usual. It gave us girls an hour to talk and gossip amongst ourselves. “Stacie, what was all the noise we heard coming from your room a little while ago? It sounded pretty serious” asked Fannie from down the table. Stacie began blushing and then volunteered, “My roommate and I were getting better acquainted.” The table laughed. Beth ventured, “Tracie and I found ways to pass the time too.” Lunch ended, lipstick was reapplied and the table was cleaned.

Miss Diane and Miss Cindy entered the dayroom; Miss Diane began the briefing. “This afternoon will be devoted to watching two important videos on feminism and the history of the oppression and discrimination of women in America. Around 4 PM you’ll be on your own until diner at 7PM. Take advantage of your free time and get to know the other girls in our group.”

We followed Miss Cindy and Miss Diane into the viewing room. By now we all knew that all Nest videos, including these, were loaded with subliminal audio & video indoctrination messages designed to modify behavior, attitudes and libidos. We had stopped caring and we watched the movies.

The movies were finally over and we were on our way back to our rooms. Dinner would be in about 4 hours.

Getting accustomed

Stacie and I stepped into our room and found several items placed on our beds. There were two containers of baby wipes, two packs of panty liners, and a pack of AA batteries. “Wow! I guess they do hear what we say.” Entering the bathroom Stacie found two larger diameter douche nozzles sealed in clear plastic packages and a box of Lite Day tampons had been placed on the sink. “Jenny, we get to share a box of tampons and you got your douche dildos!” She stepped out of her pantyhose sat on the toilet and peed.

I heard the sound of a fresh tampon wrapper being torn open so I went to the doorway to watch.

Still sitting on the toilet Stacie bent over, reached behind and slowly removed her old tampon; it was soaked with cum. She wrapped it in toilet paper and put it in the trash. She lightly lubed the new tampon applicator as I had instructed and was able to insert it with little effort. Watching her remove and insert her tampons was erotic to me. It was like watching the daughter I never had come of age. I’m sure it was the drugs but for that moment I felt very maternal.

Dressed only in our panties and bras we laid down in our bed to relax, cool down and collected our thoughts. I removed my bra for comfort. My developing breasts and large areoles were pretty I thought. My nipples were relaxed and ‘limp’ so I played with them a bit to make sure they responded. They did. They looked like perky raisins. It felt very pleasant to play with them.

Stacie rolled over to watch, moved closer and began kissing and sucking one of my sensitive tits. She put her hand into my panties and toyed with the head of my penis; my pre-cum inspired her to straddle me. “You did promise me your cherry baby doll.” My little vixen wanted to play.

First time for both of us: Stacie takes my cherry!

Stacie had never fucked anything before and I hadn’t been sodomized before. I draped a bath towel on the end of the bed, removed my panties, bent over leaned on the bed with my forearms. I looked over my shoulder and based upon her erection Stacie was very excited and standing where she needed to be; the angle should be perfect. I briefly wondered if she wore her heels if it would give her better leverage. I spread my legs and waited; my pre-cum dripped onto the towel.

Stacie tenderly lubed my pussy; inside and out before greasing her penis. That process was exciting on its own merits! She placed her lubed penis on target; I felt the heat of her cockhead radiating on my hole. I spread my cheeks wider to encourage her.

Stacie leaned forward and I wiggled my butt to facilitate initial penetration; she slid her hardness partially into my virgin pussy. I gasped at the entry, clenched the bed spread with my fists, exhaled and tried to relax.

Stacie held still, like I had done for her, to allow my pussy to accommodate her. She backed all the way out of me, grabbed my hips and then and then slowly slid completely in. I wiggled my butt for Stacie; my wiggling transferred to her dick that I had been clenching. Stacie paused to savor the warm grip of my tight pussy. We were engaging in the ultimate act of queerness for the second time; the naughtiness of the moment was intoxicating. I felt her penis twitch deep inside me.

Stacie began slowly thrusting in and out of me and set up a mutually satisfying rhythm. I was moaning and she was grunting. Stacie’s balls were slapping my butt; she was close to her first coital orgasm. She and her dick didn’t care that her orgasm would be the result of a homosexual liaison. We were close to orgasm. I was hopeful for an analgasm.

Stacie came first; “Oh, god!” Stacie yelped and began spewing her seed deep inside me. She held my hips tight, thrust deep and let loose another warm squirt.

The prostate massage by Stacie’s penis combined with the warm jets of her sperm caused an amazing analgasm for me. I sprayed the protective towel with sperm which saved our bedspread. I held still, savoring the throbbing ecstasy of the moment. Stacie withdrew from my pussy in a way that was pleasurable for the both of us. Exhausted but satiated we wallowed in joyous post coital bliss.

I turned my head toward the ceiling cameras and blew a kiss.

I earn a needed tampon

Eventually I slid out of bed and looked at the towel we had fucked on. “Damn, look at the size of the wet spots we left!” I felt a warm dribble beginning to seep from my pussy and down my inner thigh. As I rushed to the bathroom I cried, “I need a tampon!” I sat on the toilet and peed. Still seated I peeled the wrapper from my tampon, lubed and deftly inserted it; a white ‘mouse tail’ dangled. After letting Stacie do the string tug test we rested and recovered on our bed.

Afterwards

“We better get fresh panties and get ready for dinner” I announced. With Stacie watching, I grabbed two panty liners, peeled off the adhesive and attached one to my panties directly below my oozing pussy. “One liner goes directly below your pussy; further back in your panties than a woman would place it. Another liner is placed in the front to prevent pecker tracks; no leaks anywhere tonight. A box of the thin Kotex pads with wings would be nice to have.”

Stacie said, “You’re like a Fairy MacGyver! How do you know about all this stuff?” I shrugged and we both had a good laugh. Ten minutes later we left to the dining area.

Dinner

Dinner ended and Miss Cindy made the usual announcements. “As a group you’re coming along fine. A couple girls need to start meeting requirements if they don’t want to flunk out of here. If we’ve missed anything let me, Miss Martha or Miss Diane know. I’ll see you in the morning.” Miss Cindy turned and left. The table adjourned and we started to make our way back to our rooms. It was only 7 PM and the night was young. Stacie said she would be entertaining a guest and asked if I would delay my return to our room for about an hour.

Back to the room

When I opened the door to my room I found Stacie lying on our bed with her legs over Beth’s shoulders. I was just in time to see Beth pull free. Stacie blushed and began putting baby wipes to good use. Turning to face me, while continuing to clean herself, Stacie said, “Beth’s cock has a lot more life left in it in case you’re interested. She’s insatiable!” Beth had a sexy smirk on her face and was still very erect.

“Jen dear,” Beth purred, “If you’ve got the time I’d like to give you and your pussy a real good time. Just look at Stacie’s grin.” I politely declined. “Maybe another time, I’m sure it would be fun.”

Without being asked I retrieved a tampon from my purse, tossed it to Stacie, entered the bathroom and began removing my makeup. I listened as Stacie explained and demonstrated to Rose the benefit of having a ‘mouse tail’.

Day 52… or was it 72?

Breakfast

The dining table was all buzzing with yesterday’s news; Rose’s love affair with her vibrator, Beth’s love of Stacie’s pussy and something about ‘mouse tails’. I was developing a reputation of being the Swiss Army Knife of cross-dressers; ‘How does she know these things?’

Progress evaluation meeting; another sperm sample

Miss Cindy announced that Stacie, Jackie, Tracie and I were to report to the administrative building for a progress evaluation meeting and medical tests; we were excused from the morning’s activities. We were asked to remain at the dining table after the others had left. Another wave of buzzing and speculation rose from the table. The rest of the girls finished their breakfast and left leaving only us four and Miss Cindy at the table.

Miss Cindy explained that Jackie and I were to meet with Miss Diane and Stacie and Tracie were meeting with Miss Martha.

“Before you can have your review you must return to your rooms and double douche to be squeaky clean for your exam; don’t get lost pleasuring yourselves. I’ll be waiting here so be quick.” No mention was made of the hormones that had been added to all our douche products.

Twenty minutes later we all were back and were hornier than when we left; Tracie had an odd smirk on her face.

“Follow me girls” Miss Cindy said. We all stood up. I gave Stacie a hug and a kiss on her cheek. “Good luck” Stacie said. I held Jackie’s hand as we walked to the admin building. No one had been there since our arrival; we had no clue as what was about to happen.

Miss Cindy led us down a hallway and told Stacie and Tracie to enter office 2. Jackie and I went into office 2.

Meeting Miss Diane

We entered office 2 and sitting behind a large desk was Miss Diane. She looked as beautiful as always but today she was wearing lovely lavender colored sundress and a string of pearls. Two chairs were in front of her desk and a love seat and coffee table were nearby. We waited by the door for instructions.

Miss Diane began; “Good morning ladies. Before you sit down I want you both to remove your dresses, step out of your heels and strip down to bra and panties. To your right is a desk to put your purses and clothes on. When that’s done please take a seat. Be advised that there is audio and video monitoring here.”

As we were disrobed I asked Jackie “Is my makeup ok?” Jackie nodded her head to indicate yes. We were soon seated and facing Miss Diane.

“You are not in any kind of trouble but on occasion we like to have more informal conversations with our students. It’s also time to obtain another semen sample. We at The Nest have a special method for obtaining sperm samples; it involves you wearing and filling a condom with your sperm sample. What’s happening here is also happing next door with Miss Martha.”

Kudos

Miss Diane flashed a friendly smile and launched into today’s agenda. “I want to congratulate you on how feminine you have become. The eyeliner in particular was a nice touch and its use has been picked up by several of the girls. I know this began with Jenny. I also know Jenny was responsible for several other clever ideas. Her comments and suggestions are the reason that additional items were placed in your rooms. The combined use of tampons and panty liners was a new concept we hadn’t thought of before. We now feel that tampon training promotes the feminine experience.” I turned three shades of red at the compliment.

Rewarded

“You ladies have become obviously more endowed and as a reward you’ll be given new and nicer bras. Unlike our standard issue basic white bras your new bras are pretty, colored demi-bras. Two additional colored bras await you in your rooms. I can tell that the two extra injections given Jenny had the desired effect.”

Gold Hoop Earrings

“You are also getting two inch gold hoops earrings before the other girls get theirs. Your hoops and new bras should inspire the other girls. Remove your ear studs now.” We did as we were told.

Miss Diane handed us a small jewelry box containing our gold hoops. “Insert your hoops and place your studs in the box. Would you like a mirror?” We both said no. We tilted our head slightly and inserted and closed one hoop and repeated the process with the other ear. There was a noticeable ‘click’ as the hoops snapped shut.

“Your hoops have a stronger wire than normal hoops. The click you heard was locking mechanisms; your hoops can only be removed by a staff member. The other girls get their hoops next week.”

Fucked and sucked by Miss Diane

Stepping out from behind her desk Miss Diane walked to the front of her desk and stood three feet from where we were sitting. She leaned her butt against the edge of the desk and announced: “To evaluate your progress you must prove to me that you are effeminate, enthusiastic cocksuckers and willing and receptive queer ‘bottoms’.”

The shocked look on our faces made her smile; a sly grin formed on her face.

As we watched Miss Diane removed her sundress; her lingerie was black. She was wearing a beautiful breast enhancing bra, a matching garter belt, silky stockings and 3 inch black pumps. She wore no panties. An eight inch cock dangled between her legs! It appeared to be three inches in diameter. It was not flaccid and appeared to be ‘on the rise’. Jackie gasped and I nodded in appreciation of the beauty in front of me; her cock was beautiful.

Miss Diane smiled at our surprised look. “You must have noticed the length and thickness of my cock; you will become accustomed to it.” Leaning on the desk with her legs spread wide Miss Diane gave her thick shaft a seductive tip to base caress and her erection became stronger. The bulges in our panties increased. “I’m pleased to see wet spots.” Miss Diane said pointing towards our tented panties.

Progress evaluation: Our “skills” are tested

Miss Diane walked over and sat on a love seat that was covered with several large bath towels; several knee pillows waited on the floor. Boxes of tissues were nearby. She sat down.

“Remove your bras and kneel on the pillows at my feet.” Our bras came off quickly and were tossed on the desk. We knelt as instructed.

Miss Diane passed me a tube of lipstick that was my usual shade of red. I applied it, unasked, and without a mirror. Miss Diane passed Jackie a darker shade of lipstick. “Put it on Sweetie, I’m curious as who can take more cock.” Jackie did as instructed.

“Jenny, you are going to begin my blowjob and Jackie will finish it when I say so. I want to see which of you can leave red rings lowest on my shaft as possible.”

Miss Diane spread her legs and gave her long shaft few more enticing strokes. “Be a good girl Jenny and suck Mommy’s dick.”

I leaned forward and hefted Miss Diane’s penis and circled her base using my middle finger and thumb. I blotted my lips on Miss Diane’s cockhead and licked her glans before taking her into my mouth. Her cock was getting divinely stiffer and larger by the second. I gave a lot of tongue attention on the top portion of Miss Diane’s cock. Miss Diane made a low groan of appreciation. I enjoyed rubbing Miss Diane’s stockings and tugging gently on her garter straps as I sucked her cock. ‘Damn, that’s hot!’ I thought. I boldly stroked her perineum; my mouth felt her cock involuntarily flex at my touch. I pressed my lips on her shaft and left my mark.

After a few minutes of spirited cock sucking Miss Diane gently held my chin to make me stop. “You can stop now darling. You give a fine blowjob; where you touched me was heavenly. “I wanted you to cum” I whined. “I know Sweetie, all cocksuckers want the same thing but it’s Jackie’s turn.” Jackie and I traded places.

Jackie gripped the base of Miss Diane’s shaft and placed a dark red lip print on the side of her cockhead before resuming where I had left off. Jackie plunged her mouth down Miss Diane’s shaft until she felt Miss Diane’s spongy cockhead at the back of her throat; Jackie clamped her lips to mark her progress. Jackie had just begun an upward sucking and milking when Miss Diane came. Large quantities of sperm flowed into Jackie’s welcoming mouth. Maintaining direct eye contact with Miss Diane Jackie winked and swallowed; and swallowed two more times.

Watching this made me horny as hell. I leaned over and gave Jackie a prolonged kiss probing her mouth for leftovers.

Despite her ragged breathing Miss Diane managed to compliment us. “You girls are inspired cocksuckers; don’t let anyone tell you otherwise.”

Assuming we were finished Jackie and I stood up and began making our way to our purses and clothes.

Miss Diane said, “Hold on you cocksuckers, there’s two more things before you queens can leave. First, Jackie was able to take more cock then Jenny.” She pointed at her semi-flaccid penis. Our lipstick marks were clear. Jackie was able to eat about an inch more cock then me. “Second on our agenda are the sperm samples I need from each of you.”

Sperm samples

Miss Diane handed us each a special specimen collection condom. “I need to collect a sperm sample. You wear a condom and I don’t. After you roll on a condom and bend over I’m going to mount you and rub your prostate with my penis until you give me a sample; after ejaculation removes your condom and place it on the tray in front of you.” Miss Diane smiled. “Don’t worry; I won’t cum in your pussies.”

“Remove your panties, go to the front of my desk and wait for me. Jenny, will be first.” Jackie and I looked at each other in surprise. Neither of us had seen THIS coming. Miss Diane’s thick eight inch snake was going to invade us!

Miss Diane brought lube and a stack of warm moist wash cloths in a bowl to her desk. “Here’s the drill; face the desk and bend over with hands on the desk. I’ll fuck Jenny until she gives me a sample. I’ll withdraw and then collect Jackie’s sample by fucking her. When I’m finished get dressed, take your gifts and report for your makeovers.”

Miss Diane lubed her shaft and soon had the tip of her bareback cock in my rectum; my erection began to show itself. I grabbed the desk harder and Miss Diane’s next thrust went in about four inches. “Ouch!” I gasped as I tried to relax my pussy; my erection grew. I was grateful that Stacie had stretched me when she took my virginity a few days earlier. On the next thrust she was completely inside me. I gasped and my swollen penis throbbed.

Beginning a slow but steady fucking of my pussy Miss Diane made sure to drag her cockhead and shaft back and forth across my prostate; it felt so damn good! When she entered me as deep as she could I clenched down on her cock. In response Miss Diane did a ‘flex-throb’ contraction move of her cock that pushed me over the brink; I joyously erupted multiple times.

Miss Diane got her sample and I felt great about giving it. I removed the condom and placed it and its warm contents on the waiting tray. I used a warm damp face cloth to clean myself before getting dressed. I put my panties on, sat down and waited to watch what was about to happen.

Miss Diane used one of the damp wash rags from her desk to clean my slime from her still rigid penis. She tossed the used rag on her desk, turned to face Jackie and smiled; her cock twitched in anticipation.

“It’s your turn Jackie.” Miss Diane said. In a bold move, prior to bending over on Miss Diane’s desk, Jackie dropped to her knees and began fellating Miss Diane again. Taken by surprise Miss Diane held still. A few sucks later (one suck down to the red ring she had just placed there) Jackie stood up and said, “I wanted to make sure you were nice and hard.” Jackie turned, grabbed the table, bent over and spread her legs.

Miss Diane re-lubed her hardness and was soon eight inches deep in Jackie. A very excited Miss Diane grabbed Jackie by the waist and pulled her butt snuggly against her groin while repeatedly and quickly fucking her sizable shaft back and forth against her target; like a dog in heat. While holding Jackie tight, at maximum depth, Jackie clenched several times; as a result Jackie and Miss Diane both spontaneously ejaculated waves of cum.

Caught up in her own quest for pleasure Miss Diane continued to hold Jackie tight against her mons pubis; she moaned and thrust hard again sending another three squirts of sperm deep inside Jackie, pressed deeper and enjoyed Jackie’s tightness. Giving no indication that she was ever going to withdraw, Jackie pulled herself off of Miss Diane’s impressive shaft gripping it as tight as she could as she dragged it out from deep inside her bowels.

Miss Diane got her specimen and Jackie got a very large quantity of sperm from Miss Diane; Miss Diane’s viscous sperm began seeping down Jackie’s legs.

“Damn, you! You said you wouldn’t cum!” Jackie angrily barked. Jackie pulled the specimen condom off and tossed it on the desk. Grabbing a wet cloth Jackie cleaned herself.

“I’m sorry Jackie! I thought I could control it but then you did something…you milked me and I couldn’t help myself. I’m sorry.”

Jackie stormed over to her purse, got a tampon and shoved it home. She threw the wrapper and empty applicator on Miss Diane’s desk next to her sperm filled condom. Jackie got dressed.

More rewards to enhance your femininity

Miss Diane said “We prepared goodie bags for each of you that include: Victoria’s Secret garter belts, several pair of 15 denier nylon stockings, 2 special bras, Victoria’s Secret panties with your names on them, 4 inch pumps and an eight inch silicon dildo. Take the lipsticks you used today; your names are engraved on the tubes. A special makeover, manicure and eyebrow waxing await you.” We both would receive something special for taking it up the ass.

We grabbed our gift bags and put our old heels into them. Jackie stomped out of the room; I followed. We quickly adapted to the higher heels.

The makeover - time to relax and compose ourselves

Jackie and I thoroughly enjoyed our makeovers. My natural hair is dirty blonde so I selected platinum blonde with highlights with a fringed pixie cut; Jackie, being a brunette, opted for medium shag with bangs and a hint of red. Our brows were waxed to perfection and the manicure left our toes and fingernails well shaped and pretty. Our eyeliner, eye shadow, lips, etc. looked perfect! Since it was semi-permanent makeup it could not be washed off.

Lunch was soon and we were getting ready to leave when our beauticians told us to relax a little longer explaining, “We have instructions from Miss Diane to do something special for you and that you’d understand why.” I started laughing and told Jackie, “Lay back and enjoy the perks of having sucked the right person; we’ve become cock sucking whores!” We relaxed and let the beauticians work their magic.

Neither of us had a Brazilian wax before. An hour later Jackie and I left waxed and smooth in every area possible; we exuded femininity. I knew that Stacie and Tracie would enjoy our girly smoothness.

Time for lunch: We dressed in our rewards

Using a spare room in the salon we took time to put on our new garter belts and hose. I had mine on in short order. Jackie struggled and I helped clip her garters to her stockings being sure to put panties over the garter belt. “Wearing panties over a garter belt makes it easier to pull your panties down and pee…or be sucked” I explained. Jackie wondered, ‘How does she know these things?’

After Jackie changed her soggy tampon and we slipped into our new 4 inch pumps. I asked Jackie to pass me her new tube of dark red lipstick. I applied the new color and passed the tube back to Jackie; “No one has this shade!” We unbuttoned the top two buttons of our blouses and strode, hand in hand, into the dining area with our makeover, lingerie and ‘goodie bags’; we would catch the last 30 minutes of lunch.

Lunch

Freshly fucked and waxed

As we approached the lunch table the entire table of girls turned to look. Stacie and Tracie were already seated. Comments of ‘Wow’, ‘fantastic’ ‘damn, they’re hot’ were heard. Jackie made a point of lifting her skirt to show off her new garter belt and stockings. Her name embroidered on her garter belt was noticed by all. Jackie snapped one of her garter straps for effect, smoothed her skirt and sat down at the table. I sat next to her. Someone said “Look, they have matching hoops, manicured nails and new heels just like Stacie and Tracie”.

“Damn, you both seem so beautiful and radiant” remarked Fannie. “Those stockings make you legs look so pretty.” “We were treated to a full Brazilian body wax; legs, eyebrows, front and rear boy bits. Having our pubic areas waxed felt weird. We won’t need to shave anything for quite a while.”

Fannie pressed further, “Why did you get the extra treatment… who did you have to fuck?” Jackie looked around the table and said, “Trust me, we earned everything. I’m not sure that the rewards were worth the price my pussy had to pay.” She was smirking.

Lunch was over and everyone was to go to session 18 of voice modulation where we were being taught how to sound feminine. Marked improvement was apparent in every one of us; speaking with a feminine voice and inflection was becoming second nature. Of course we had been educated about and had been offered voice feminization injections and laryngoplasty surgery.

Comparing notes

I made sure that Stacie, Tracie and Jackie held back for a few minutes. I wanted to compare notes with the two girls that had been ‘interviewed’ by Martha.

“How did it go for you two? I see you also got goodie bags. Did you have to give Martha a blowjob?” I asked. Tracie seemed surprised. “Yes, we took turns sucking Martha. She is hung like a horse; “My jaw and tonsils are still aching!” Stacie said. “Their semen collection method was interesting” added Tracie.

“When Miss Diane is naked it looks like she has a snake dropping from her crotch” Jackie commented. “I was ‘lucky’ to get the ‘gift’ of an amazing amount of her seed. I didn’t think I would be hungry for lunch because she came so much.”

Tracie and Stacie looked surprised. “So why did you girls get the special wax job?”

Miss Diane was trying to make up for an ‘accident’ she had in my ass! That reminds me, I need to swap out a tampon. You ladies go ahead and I’ll catch up.”

Dinner

Nothing new or exciting. The enhanced femininity that the ‘special’ makeovers did for our appearances was noticed and appreciated by all. Comments about Miss Diane’s massive appendage and what a Brazilian wax feels like were of great interest.

Weeks and months pass

The Program progressively increased their expectations of us. When we become comfortable and proficient with a certain degree of our femininity the Program would up the ante and require more. Pantyhose evolved to garter belts and stockings; Two inch heels became three and then four inch heels. B cup tits became C cup breasts. The Program wanted us to expand our girlishness and we did. The Program wanted us to experience sex with men and we did.

We requested and received tracheal ‘shaves’, laryngoplasty and a couple other feminization procedures. Our mannerisms, deportment, attitudes, voices, breasts and sex acts had become feminine; hair styles, makeup and clothing choices became more sophisticated and sexy. Our blowjobs became increasingly superb. We ‘fledglings’ were trying out our ‘wings’ and wanted to fly free; we wanted our IDs. Months flew by.

Over the months I had my shoulder length hair softly permed and dyed platinum blonde; Jackie went red head. She really looked hot; it suited her well. We all were nervous. It would be time to leave after the IDs arrived. Where were they? We waited.

New State ID cards

The Program promised to provide us with new State ID cards with a photo of our newly feminine selves, so we could cash checks, travel and get on with our lives. The IDs would still indicate gender as male. If anyone wanted to make ‘the final leap’ and transition to a fully functioning female the new ID would reflect female. The ‘fabulous four’ wanted to remain ‘Chicks with Dicks’ for the time being.

Daydreaming and reflecting

Stacie was in the day room whiling away her time, chatting with others, painting her nails and listening to TV. I was alone in our room.

I sat pensively on the edge of our bed, nervously twitching my stocking clad foot which in turn caused my black 4 inch heels to slip on and off my foot. Yes, I had progressed to wearing 4 inch heels. I was wondering WHEN my new ID would arrive. I glanced at my dark red ‘Cherries in the Snow’ fingernails.

Playing for the cameras I stood up from my bed and made sure to pull my dress down in well rehearsed lady like fashion. I walked over to the full length mirror and gave myself another inspection. I touched up my lipstick; by now it was second nature. I took a deep breath and sat down in our loveseat, instinctively smoothing my dress as I sat. I crossed my stocking covered legs just like Sharon Stone had done in Fatal Attraction. Picking up a fashion magazine I took my time in flipping the pages while fiddling with my earrings.

Out of boredom I put down the magazine, walked over to the bed and laid down making a concerted effort to not mess my hair or dress. I kicked off my pumps and lay back. I closed my well made up eyes and let my mind wander back to my first day days at The Nest. It seemed like such a long time ago. I dozed off.

Stacie Returns

Returning from the day room Stacie entered our room, placed her purse and a large envelope on our nightstand before giving me a kiss. I emerged from my trip down memory lane. “Are you alright, Jenny? You seem a little spaced out.” Stacie said.

“I’m fine Stacie. I can’t believe a new State ID takes so freaking long! I was also thinking about our first week here. It seems so long ago.” Stacie walked over and sat next to me on our bed. She smiled down at me and stroked my hair in an effort to comfort me. Stacie leaned down and kissed me gently on my lips. “It’s almost over darling” Stacie whispered.

I smiled and with a well practiced move I pulled Stacie down onto the bed and gave her a longer and more passionate kiss; we kissed and cuddled.

Stacie: A good time waiting to happen

Stacie made a beautiful sight lying on the bed; her smile, sultry made up eyes were inviting; she looked like a good time waiting to happen; she was angelic. We rolled over to face each other. Stacie smiled delightfully and gave me a loving kiss on the side of my neck. “I brought you something, darling” Stacie purred. Rising from the bed Stacie retrieved the envelope from the nightstand and handed it to me.

Opening the envelope I found a letter and official looking documents. I removed the paperwork and reached in again and froze. I gripped what I thought was a 3x5 card and withdrew my hand. I gasped! In my hand was my brand new, shiny, State ID card! I looked at my ID and there was photo of a pretty young woman on it; that woman was me! The look of surprise on my face made Stacie laugh. Holding the ID to my breast I closed my eyes and began to softly cry; they were tears of happiness.

My brand new, shiny, State ID card!

Stacie hugged me again. She wiped a tear off my cheek. Wrapping her arm around me, she hugged me tighter and whispered, “Don’t worry darling, we got through it and we’ll be fine, just like you said we would so long ago; and we have each other, right?”

I stopped my crying and Stacie relaxed her hug. “We ALL got our IDs just a little while ago! Jackie, Tracie and Rose are sitting in the day room waiting for us. Let’s go share the moment.” We both giggled like school girls.

Sharing the moment

Stacie and I walked into our makeshift living room area proudly holding our new State ID cards. We joined Jackie Rose and Tracie. We plopped ourselves onto a love seat.

Everyone received their IDs!

Our entire group of ladies would be leaving The Nest at the same time; we had ‘graduated’. Perhaps the threats of being held longer were false; perhaps a new group of trainees needed our space. It didn’t matter. We were going to be able to resume our previous lives… if we wanted too. Considering our feminine transformation could any of us truly go back to our previous lives? Would friends and family accept us? All things considered, who among us would want to regress back into toxic masculinity?

‘So what are you going to do now?

Rose began. “I know I don’t want to go back to living as a male. Maybe I’ll go back to school. Based upon my experience here speech pathology or audiology seems interesting. I would be helping people. It would be better than a boring office job.”

Stacie piped up next. “I really don’t want to go back to an accounting job. I was hoping to open a bed and breakfast place or maybe a transitional safe zone for wayward or troubled young cross-dressers. Jenny and I have thought about going into business together. We certainly have the experience!” We all chuckled and nodded our heads in the affirmative. Stacie continued; “Before I came here I had few friends. Now I have three good girlfriends.” Stacie paused to let that concept sink in. It was a touching moment. “I’d gladly give any of you my last tampon!” she joked.

“What about you, Jackie?”

Jackie took a moment to think and flipped her hair back in a most feminine manner. “For some strange reason I like this place. Not at first, but it has brought some order to my life and it put me in touch with my feminine self; for that I will always be grateful. I have heard that Martha is leaving The Nest to join her girlfriend somewhere in California; the Hollywood area I think. I’ve already made a formal application with Matron to work here. I think I could really help the new ‘girls in training’ that are headed our way. It would also provide an income, a roof over my head and a source for beautiful clothes.”

The girls turned their heads toward me and waited for my response

I had been subconsciously toying with my hoop earrings.

“I’m inclined to go along with Stacie’s idea. I think there’s a real need for a user friendly transitional environment for younger cross-dressers who are lost and confused. I think Stacie and I could help them get through a rough spot in their lives. In terms of adult cross-dressers I think we would get a LOT of referrals from The Nest, especially if we had someone like Jackie on the inside.”

I winked at Jackie and continued; “For me it would be a labor of love. We could take advantage of the halfway housing offered us by The Nest which would save us almost a year’s rent. We could apply the amount we saved and invest it in our new business. Maybe The Nest would help us get it up and running, rent us a place on their compound and share resources.”

We smiled at each other and leaned forward to grab hands, making a friendship circle; sweet tears of relief spilled down our cheeks. Contentment seemed to ooze from us all. A couple minutes went by and I loudly cleared my throat. I wanted their full attention.

Revelations from Jenny: Why she knew all those things

“I have something I want to share with you. On more than one occasion you and others have asked ‘How does Jenny know about all these womanly things?’ Three things in particular come to mind: my use of tampons, how I used lipstick for blush and how I made crotch control gaffs from old pantyhose. Do you remember?”

“I sure do!” said Stacie. “I wondered where you got your expertise with eyeliner.” “There were a few other things that seemed odd like the ability to hook your bra behind your back” tossed in Jackie. I softly giggled and leaned forward in my chair and continued.

“The expression that ‘the apple doesn’t fall far from the tree’ comes to mind. With my mother’s approval it was my father who taught me everything I know about make-up, lingerie and women’s clothes. Dad had been a cross-dresser since he was five or six.”

“When I was four or five he’d sit me on his stocking covered knee and I’d watch him apply his make-up or nail polish. I would play with his tubes of lipstick, nail polish and perfume bottles, etc. I’d say, ‘gimme gimme’ and he’d paint my nails, apply a light shade of lipstick or maybe run a dry mascara wand on my lashes. I still remember the delicious tastes and smells. If he asked me to hand him his bra or panties I’d go get them. I didn’t know those activities were considered ‘girly’.”

“Mom didn’t mind any of it. She used to help dad with his dressing and make-up sometimes and eventually with me. At age six I started dressing as a girl at home. That same year mom gave me my first set of panties and a nylon sleep set for Christmas; she gave me my first makeover at age seven. Because I begged and pleaded we had my ears pierced at ten. I’ve been wearing stud earrings in public ever since. I always wore age appropriate girl clothes and looked forward to birthdays and Christmas.”

“Mom was the one to show me how to properly shave my legs and it was dad that rolled my very first set of nylons up to my very first garter belt. It was our family secret.” I took a deep breath, leaned back in my chair, took a sip of water and continued.

Tampons and panty liners?

“Mom was a would-be artist, painter and poet and thought that all of the femininity being heaped on me would inspire my artistic and sensitive side. Dad was a mid level office manager and always shaved his legs, wore lingerie under his suits and sport jackets. He taught me to wear an A cup starter bra under a T-shirt in order to go unnoticed. Shear, ‘nude toe’ hose and nylon tap pants were natural to me. Sex was never a part of any of this. I did learn, personally, how lingerie can cause erections and ‘wet spots’. Dad showed me the advantage that a panty liner provided. We just never spoke about or flaunted our ‘hobby’ to anyone.”

I know you’re wondering about my knowledge of tampons. I think it was when I was fifteen. I had been diagnosed with a severe form of IBS and diverticulitis. I was having medical problems with anal control; rectal leakage was a problem. Mom came up with the Lite Day tampon solution. The thin panty liner Kotex, with wings, was dad’s inspiration. I have used them both frequently. I remember being extremely embarrassed when I lost the string to my tampon once. It took both of my parents to find and remove it. Dad kept pushing it deeper! Two years later my medical condition was resolved and I didn’t need either of those items yet I was fully experienced in their use.

“Considering all that I just told you I hope you can see the irony of me being assigned to this program. I’m pretty sure I have the high femininity profile The Program was looking for. It may sound strange until I got here I had never had sex with a man.” I began to softly cry. The girls were silent as they tried to absorb what they had just been told. Tears were running down everyone’s cheeks.

It took a minute but all the girls stood and silently motioned me to rise. Stacie, Rose and Jackie stepped over to me and created a four person hug; we were all quietly crying. We were going through a lot of tissues. It was a very tender moment.

Stacie went for a solo hug and kissed me tenderly on the lips. “I knew there was something, sweetheart. Thanks for trusting us so much as to share this. I couldn’t have had a better roommate, business buddy or sex partner.” Giving me another smooch she stepped back and let Jackie have her own moment with me.

Jackie and I embraced firmly and enjoyed the personal kind of kiss that only a lover could give. Jackie wiped her own tears and then, while holding my head gently in her hands, used her thumbs to remove the tears from my cheeks. “Damn, I love you!” Jackie said. You would never be able to find a happier group of male lesbians anywhere.

In a remote video monitoring room Miss Diane managed to stop crying. She smiled, shook her head and laughed.

****************

Dear readers: I invite you to read my other Big Closet stories (there are 24 stories so far). Be sure to at least leave a "hello" in the review/comment area. I recommend:

“Adventures of Sara: Evolving deeper into femininity” –
“A Womanless Beauty Pageant: It was the zipper's fault” –
“Accidental Acceptance” – and the “Avon Lady” series

Do a ‘Search by Author’ for Donna T and enjoy. Be sure to say “hello” in the review. Hugs and kisses to you all.

Maxie’s “Dutch Treat” (Part 2 of 2)

Recap of Part 1:

Synopsis: My name was Marc; friends call me Maxine. I was raised in a single parent household with no male role model. Mom and two sisters made sure I was pretty as I grew up. As a result I am attracted to a femine way of life, women's clothing and men. I've never left a date disappointed.

After graduating trade school I found a unique way to financial security while also exploring opportunities to express my innate femininity. To that end I found I had to be an actress of sorts; I was facing an "audition" that would change my life as well as Vivian's and Melanie's lives.

If you've not read Part One a brief synopsis is provided. - Special thanks go out to the REAL Maxine that inspired this story.

Previously at end of Part 1: THE REVEAL – “I stood at Vivian & Melanie’s door for a moment before ringing their doorbell. I adjusted my sweater sportily over my shoulders like a cloak and took a few deep breaths. I knew they had been coaxing me to reveal the inner me; the inner Maxie. I was glad I decided to wear slacks.

I rang the doorbell. The door opened.

Oh, my!

Melanie opened the door and froze in place, mouth open and stared as she tried to take in what she was seeing. I waited a long moment and said, “Good evening Mel. My name is Maxine and I’m your new neighbor; my friends call me Maxie. I hope I’m on time.” Mel’s eyes widened, her face lit up and smiled. “Oh, my God! You’re beautiful! Please step in… Maxine.”

I stepped into the house, briefly displayed my fingernails for Mel’s inspection and waited.

“Mom! Come quick, we have a lady visitor!” Vivian rushed in from the kitchen and stopped in her tracks. “Oh, my God!” she also exclaimed. I began to blush.

Mel said, “Mom, meet Maxine.”

V & M embraced me warmly, held me at arm’s length to confirm what they were seeing and then hugged me again. Viv kissed me on the cheek and smiled in disbelief. Mel took my sweater and commented “You smell as pretty as you look.”

I was made to do a slow turn so they could take in my feminine beauty. Both ladies shook their heads in pleasant disbelief.

“I had no idea that our handy-“man” could also be a pretty woman!” Vivian exclaimed. Mel added, “We obviously had our suspicions but never in our wildest dream did we expect how nicely feminine you could be! I’d love to see you in a dress.”

“Me too, I’d love for you to see me in a dress but I didn’t want to overwhelm you with my cleavage so I went with a less femme outfit” was my reply.

“Less femme?” Mel asked. “I hate to disappoint you Sweetie but you certainly don’t look unfeminine to me!”

“Maybe, once this is all over, I’ll breakout my sexy party dress and we can have a girl’s night out” I replied.

Vivian said, “Let’s adjourn to the living room where we girls can be more comfortable.” I was ushered into their living room for girl talk and questions. Once seated I crossed my legs in a feminine manner and to break the ice I made a pouty face and asked, “What’s a girl got to do to get a drink around here?” We all laughed at my question; I began to relax.

“What’s your pleasure Princess?” I was asked.

“Do you have a Chardonnay or a not too sweet Riesling?” I queried.

What’s your story Morning Glory?

Over the next 30 minutes and two glasses of wine I answered most of their tactful questions. They raved about my clothes, hair, makeup and earrings. I was also complimented on my anklet and neck chain; “My sisters gave me the anklet when they left for college.” I hesitated a moment and continued, “A boyfriend gave me the neck chain.”

Vivian and Melanie exchanged looks of surprise; they now knew exactly who and what I really was; their questions kept coming.

“How did you get so skilled with your hair?”

“Mom always fussed with my hair so I could look like my sisters; I became so familiar with wearing ponytails, barrettes, dresses and makeup that I considered becoming a hairdresser.”

“Who decided to get your ears pierced?”

I sheepishly responded, “I did. When my sisters had their ears pierced I begged mom to have mine pierced too. I was six years old; I wore gold starter studs at first but eventually mom let me wear big girl hoops like my sisters; earrings became a routine part of life.”

“That sounds normal to me,” quipped Mel. “But then again I’m a girl. Are you?”

I ignored her question. All you had to do was look at me and have heard my self-revelations and know the answer.

We emptied our bottle of wine. V & M decided it took the two of them in the kitchen to get more. They went to the kitchen and as they uncorked another bottle of wine I could hear them whispering amongst themselves. Maxie and I enjoyed the moment of quiet; I closed my eyes and slowly exhaled; I felt the nervous tension in my neck subside.

More wine, more questions

Viv and Mel returned with the wine and announced that the dinner was in the oven and almost ready. “You should never rush pot roast” I said.

Vivian said “I have a couple more questions and then we’ll leave you in peace. You must admit that your background combined with you meeting up with us and our special salon is pretty amazing; it’s like divine intervention.”

“Yes, it is an amazing set of circumstances” I agreed. I was still curious about Dutch and his ‘test’.

“So you were just one of the girls as you grew up? Do tell!” Viv casually asked. So I did. Living alone is no fun.
“Yes. I was always ‘just one of the girls’ and I still am.” I squirmed uncomfortably in my chair.
“When you’re in girl mode may we call you Marcia? It seems to fit much better than Marc.”

“No, call me Maxie; it’s short for Maxine; Maxine was to be the third baby girl that my mother never had. I’ve been Maxie for all my life.”

Dinner

The homemade pot roast with all the trimmings was delicious. It was the best food I had eaten in several months. Fast food and microwaves may be filling but homemade meals are best.

Over dinner V & M filled me in on possibly acquiring a second salon; a spa that catered 80% to the gay, transgender and ‘special needs’ community that Melanie would run. I was again made aware that if they were to be able to acquire the new salon it involved passing a very odd ‘proof of ability’ evaluation mandated by the seller. “Dutch is a bit offbeat” they volunteered. “He wants to leave his clients in good hands.”

V & M explain

“Dutch was a guest at an extravagant transgender wedding we were involved with. We did a fantastic job in making the entire wedding party beautifully feminine; the male bride and six men in the bridal party were absolutely gorgeous when we got done with them. Our effort attracted Dutch’s attention.”

Vivian: “The Duchess approached Mel at the reception and told her that he was impressed with our work. He mentioned that he was retiring and was anxious to sell his “The Woman Within” salon, and all name and franchise rights, to the “right” people. He was aware that our salon, like his salon, discretely served the LGBTQ community without passing judgment. He asked if we would be interested in buying his shop and franchise potential; he wants his clients to continue to be well taken care of.”

“I told Dutch that we had very limited funds and virtually no collateral.”

Vivian: “When Mel returned home she told me about the fantastic opportunity Dutch had mentioned. We agreed that we shouldn’t let this opportunity slip away and vowed to do whatever was necessary to make the deal work.”

“Whatever is necessary?” I asked.

Vivian: “Dutch has made a small fortune with his salon and is retiring to Palm Beach, Florida and enjoy life with his boyfriends. Acquiring his salon would be a very good thing for us and we could sell franchises nationwide; we could become filthy rich!”

And, as if I didn’t know, Mel added, “Everyone knows that Palm Beach is a well-known gay community with a thriving LGBTQ nightlife; it’s a popular vacation destination for gay travelers. Palm Beach is to Florida what Fire Island is to New York.”

Questions become more direct

The meal was over and the evening was winding down. V & M touched up their lipstick. When they were done they politely offered me their lipstick. Without saying a word I reached into my purse, retrieved my own lipstick and expertly colored my lips without a mirror! I smirked, held up my lipstick; it was identical to theirs. “It appears we share the same shade.” I quipped, “Perhaps we also share the same type of man.” We all laughed.

Could a handyman help them attain their goal? I asked how I could help.

To access my potential of being able to help with their Dutch problem V & M had more questions; very pointed and very direct questions. I was a bit buzzed on the wine and I may have been more forthcoming than I should have been.

THE questions

Q - “Do you date? Have you ever been “with” a man?”

A - “It’s been awhile but I’ve had my share of boyfriends if that’s what you mean.”

Q - “Let me rephrase that” said Vivian. “Have you ever been intimate with a man?”

A - “I’m not a tramp but I manage to have a good time when I go out. I’m an enthusiastic ‘bottom’ but can be an in-control ‘top’ when the mood suits me. I’ve never left a date disappointed.” I pointed to Troy’s necklace.

They had a puzzled look. I sensed hesitation so I expanded on my reply.
A - “Recently, by personal choice, Maxine went dormant like a once vibrant volcano.”

Q - “What if that volcano was needed to ‘erupt’ again… for a special need or good cause?”
Thinking I knew where they were going with their interrogation I quipped; “It would depend on the cause and what’s in it for me.”

Q - “You really amaze us Maxie! Is there anything else you’d like to share?”

A - “Yes. I sit down when I pee; I can hang drywall and can fix or build almost anything. Most important for your special need with Dutch is that I can milk a man to orgasms without using my hands.”

V & M smiled broadly and in unison proclaimed “She’ll do quite nicely! I think we have an ace in the hole, no pun intended, with Maxie; we just may have a chance with Dutch.”

“What?” I asked. I was pretty sure it was my hole that they wanted Dutch to stick his “ace” into.

“As part of Dutch’s evaluation he wants our pretty dormant ‘volcano’ to erupt again; multiple times! In reality HE wants to ‘erupt’ many times and it’s up to you to make sure it happens.” Viv made it sound so stark and clinical.

“So my goal would be to fuck or suck whatever it takes to get Dutch to sign the sales agreement?” I asked.

Melanie told me, “That sums it up pretty well Maxine; considering your past this could be a fun assignment.”

I took another sip of wine; “It’s been a long time since I felt the rhythm of testicles slapping against my butt; after Dutch signs off on OUR new salon and if I don’t wear him out I may stay with Dutch a bit longer.” I had said “our” salon on purpose.

Mel turned to Viv and said, “I think we have the right girl for this assignment and we now have a fighting chance of owning a new salon.”

Time to say good night: a sorority of three

I took a last sip of wine, leaving a lip print on the glass and bid my farewells. I thanked my hostesses for a fine meal and very “interesting” conversation. Vic and Mel smiled and thanked me for trusting them with such personal information. “We’ll get more information when we meet with Dutch in a day or two; we’ll keep you posted.”

The three of us hugged and I made my way home to remove my makeup, take my ’vitamin’ and go to bed.

In retrospect all of our planning, conversations and time together were something I subconsciously needed; I felt that I was just ‘one of the girls’ again; it had been too long of a time since I had felt this way. It felt good.

Vivian and Melanie meet with Dutch for clarification

Dutch - “I like my boyfriends to be Las Vegas showgirl stunning and buxom; I insist their makeup be over the top and heavy handed. Shiny emerald-blue eye shadow, heavy eyeliner and eye brows, over sized eyelashes and exaggerated lipstick.”

V & M looked at each other and asked, “Oh, is that all? “You have very high expectations. Where in the state are we going to find a willing pansy that will fulfill your queer criteria? We can’t just take out an ad or dial ‘Rent a Tranny’ can we? I think my sources for ‘well rounded’ Sissies willing to endure theatrical makeup, constricting undergarments and what you have planned is very limited!”

Dutch - “Yeah, your lucky Sissy must have exceptional oral skills and spend the night with me in my bed as my paid whore doing whatever I ask. I’ll reserve a suite at the Fairmont Hotel for two nights that any girly-boy would love to spend a night in.”

V & M looked at each other and asked, “Oh, is that all?”

Dutch took a sip of his Fire Island Cosmopolitan cocktail before continuing; “Tell your Sissy that he can keep all of clothes, wigs and high heels when I’m done with him.”

“What you’re asking is over-the-top difficult, time consuming and expensive; our steady customers will be kicked to the curb and we’ll lose much needed income while we indulge your debaucherous fantasies. We need startup money if you want your fantasy to happen?”

“I know my evaluation will be expensive to you so I’ll gift you $2000 seed money to offset your losses and get you started buying any needed items. I always planned on going out with a bang when I retired; now I’ll go out with several very memorable ‘bangs’.

“Tell the Sissy that if all goes well and after I put a not-so-little something in his mouth and ass a few times that I’ll put a little something extra in his purse, swat him on his ass and send him waddling out the door with a smile on his face.”

Poor Maxie!

Aware of Dutch’s lecherous intentions they asked if I would be their entrant in Dutch’s bizarre “contest.”

“When people find out that your hair, make-up, nails and wig came from V & M our sales will shoot up” Mel predicted. She wanted me bring a stack of business cards in my purse.

Mel and Viv explain Dutch’s rules

“Maxine, we need to find a ‘someone’ willing to submit to an over-the-top showgirl/hooker makeover that includes shiny emerald-blue eye shadow, heavy eyeliner and bold eye brows, over sized eyelashes and exaggerated lipstick.”

I thought to myself ‘So far I don’t see a problem.’

Vivian: “Our entrant must look and behave like a lascivious woman looking to meet a man and get laid. His poise, image and slutty sensuality must be good enough to get him to award us his salon. Most importantly our contestant must agree to spend the night with him at the Fairmont Hotel and submit to his every whim. In reality the Dutchman is trolling for a Sissy trollup that he could have his way with.”

I thought to myself ‘So far I don’t see a problem.’

Maxie: “If I’m to succeed I need background info about who Dutch is; what makes him tick, what to expect, what he likes, how I should act… I need a ‘tell’, something to give me an advantage.”

“Dutch is a rich gay man looking for a goodtime. When you first meet Dutch it will be obvious that young men are on his mind. His blond streaked hair, perfectly manicured (slightly tinted?) nails, tight fitting slacks, open necked colorful shirt, multiple gold neck chains and ‘swish’ demeanor will leave no doubt about his intentions. The lump in his pants and diamond ear studs are more of a calling card than a fashion statement. Don’t be intimidated.”

“Rumor has it that he likes his boys to wear pantyhose and call him Daddy.”

Convincing me or bribing me?

After a few cocktails they revealed the details of Dutch’s requests. I told them that the idea was oddly appealing. The ordeal would be like an extremely erotic, Las Vegas showgirl makeover; a makeover that would satisfy a nagging curiosity and provide me with a nice cash bonus. Some girls like me pay a lot of money for this extreme of a makeover. I didn’t mention that the sex I anticipated would be a bonus.

I decided to leverage the situation by being reluctant to quickly reply.

V & M upped their offer to me by telling me that I could keep all ‘evaluation’ clothes, makeup, shoes, and boots that Dutch had mandated. V & M would also pay me $5000 (in addition to Dutch’s $2000) IF they got ownership of Dutch’s salon and $2000 if we failed. “$7,000 is a big incentive to do well and win.”

Mel chimed in with, “We’ll also pay your way through a state-licensed cosmetology program and guaranty that you will get your license.”

All things combined it was an offer I couldn’t refuse; I now had options.

They agreed. I said yes.

Being the woman I am I was able to quickly rattle off all my sizes. Despite my detailed sizing information V &M took my measurements again. “We have a lot to gain and a lot to lose so we’re not taking any chances for a misstep Princess.”

When Vivian said, “We need to visit upscale thrift stores for some of your clothes” I frowned and countered with “I’d prefer new clothes from REAL stores or online stores. I don’t want to be the pretty Princess that goes to her first ball looking frumpy and out of style.”

To lighten the mood Mel replied, “Sorry Princess, you aren’t going to a ball, you are going to BE balled!”

Outwardly I cringed at Mel’s comment but inwardly I felt an exciting anticipation of things to come. The caldron of ‘Volcano Maxine’ was beginning to heat up and bubble.

Shopping list

Based on Dutch’s kinks and ‘suggestions’ we put together a basic list of what special items, undergarments, clothes, boots, and makeup we’d need. I said “Be sure we get a dozen ribbed condoms.”

“Ribbed condoms?” Viv asked.

“The condoms are for Dutch and the ribbing is for me. I have to get some fun out of this experience don’t I? Besides I want to see if I can pull one off of Dutch’s shaft without using my hands.”

V & M looked a bit startled at my openness.

“If you’ve not been on the receiving end of a ribbed ‘love glove’ you don’t know what you’re missing out on.” I smirked and added, “I could help you ladies experience the thrill of a ribbed rubber sometime, just ask.” They gave me two thumbs up.

What Dutch Wants?

The list included: 40 D breasts, long line bra, open bottom girdle, black PVC above the knee skirt, boots, heavy makeup, a ‘girl’ willing to submit to his needs. There were ways to earn ‘extra credit’ and that he would let his date know.

I told them, “I want two additional pairs of black and two additional pairs of red crotch-less Silky pantyhose for me and another set for Dutch.” My request took them by surprise but they agreed.

V & M were adamant about having two high quality wigs. For simplicity’s sake I advocated for just one wig. They reluctantly acquiesced.

The day before

I arrived at the salon with a positive attitude and a clean face. With L & M’s help, and without the heavy handed makeup that Dutch demanded, I began being outfitted in my dating regalia; it was an ordeal getting dressed in such constricting ‘gear’. We laughed our way through the process with the help of a martini or two but were glad when we finished. The results were both startling and exotic; big tittie Maxine in a mini skirt was far from reality. Mel made a point of capturing the process with her cell phone camera.

Without any makeup or wig my image looked bland so I asked them to use their cosmetology skills and do my face and hair in a more traditional feminine manner. To be less time consuming they used a curling iron on my natural hair; they added the sparkly chandelier earrings I would wear tomorrow. When they were done our consensus was “Wow”!

Before doing my acrylics we had another martini; we all felt relaxed. We decided yesterday that getting my acrylic nails done today would give me some experience with longer nails; a long nailed clumsy queen would be a deal breaker; it would also save time and stress tomorrow.

Since my nails would be a 90 minute process I sat in a comfortable overstuffed chair and watched as Mel worked her girly magic.

Mel gave me one inch long ‘rounded’ nails and then got creative with rhinestones and graphics. The 1 ½ hour process was worth it based on the beautiful results; it definitely was a feminine experience; I imagined I could feel my body being re-molded by my heavy duty bra and girdle.

Even if Dutch was not impressed I was; I found them to be erotic! I had a mental image of how Dutch or any boyfriend would respond to seeing these acrylic beauties wrapped around their cock; I longed to see them gripping my cock!

I made a mental note to indulge myself with pretty nails whenever possible or passable; working for V & M would solve that problem. The results were exceptionally ‘over-the-top’ gorgeous. Mel took more photos; some were for her portfolio to show clients.

I stood from the chair, flashed my new nails at them and we hugged. “Thank you ladies, you did a marvelous job; I’ll be sure to refer all my girlfriends to you.”

To also get used to the feel of the short blonde wig they fitted it to my head and did a quick styling; tomorrow they would spend more time on it. I found it exciting to be a blonde. “When I get home I’d love to try on a few more wigs!” They nodded, “Anything our Maxie wants” they collectively said.

We retreated to the living room for cocktails and a snack. We discussed how tomorrow would evolve. A limo was arriving for at 1 PM in order to get me to the Fairmont Hotel by 2 PM. Check-in was at 4 PM. Dutch had reservations for dinner at 5 PM, cocktails at 4 PM which would give Dutch ample time to show off his Sissy ‘date’.

We decided that if arrived at 8 AM it would give us five hours to prepare; have cocktails, get made-up, have cocktails and get dressed. Having my nails done today would give me more time tomorrow before having to face my fate.

It was agreed that I would phone Vivian, night or day, if Dutch agreed to sell his ‘The Woman Within’ beauty shop. Likewise, day or night, I was to call to be picked up from The Fairmont. “Don’t be afraid to ‘tap out’.

After a very busy and stressful day I returned home to get the rest I would need to accomplish my mission; “fuck or suck whatever it takes to get Dutch to sign the sales agreement.”

Final Exam Day

After a morning muffin and a cup of coffee I gave myself two enemas which is my usual procedure when I know I’m going to be fucked. As I showered I shaved myself baby smooth; I then shaved my legs and face. I put on panties and a satin dressing gown, grabbed my purse and left for the big event.

I showed up 30 minutes early in order to drink coffee and get in the right frame of mind before letting Vivian and Mel have their way with me. I made sure that my pubes were closely shaved and well tucked. I found myself anxious yet excited about the transformation I would have.

Viv and Mel thanked me again and again for agreeing to such a wild scheme in trying to acquire ‘The Woman Within’ salon. I had a vested interest in making it happen.

Panties and nylons – Viv sent me into an adjacent bedroom to put on my panties and pantyhose saying “I don’t need to see your junk this early in the day.” I donned red high waist French cut satin panties with a sexy rear access ‘portal’. L & M would help me later with my very controlling girdle and torso hugging long line bra. After slipping into a pair of black crotch-less panty hose I left the bedroom and briefly modeled my under layer pretties.

Mel handed me a short modesty slip. “You look like you are open and ready for business Maxine; good job.”

Makeup

Before putting on any of my other clothes I sat in the beauty chair and Mel and Vivian begin the makeup process that would give me an image and persona I had never experienced before.

Face – I have a very light/reddish complexion and knowing how essential my facial makeup would be we used RCMA Crème stick foundation makeup. Sephora blush on my cheek bones went well with my lip color; the blush went all the way to my ear line. Using an eyeliner pencil Vivian created a fashion beauty mark that qualified as being ‘over-the-top’.

Full makeup and chandelier earrings

Eye brows – Mel fulfilled our goal of being ‘over-the-top’ when she penciled and brushed my eyebrows. My brows were dramatically stark.

Eye lids – Mel used 3 shades of eye shadow beginning with a dark emerald-blue shadow next to my lash line; then a softer blue color and finishing with silver up to the eyebrow line. She spent a lot of time with an eyeliner pen. Sensing I was startled at her results Mel said, “Dutch wants an over-the-top ‘working girl’ look; I believe this meets that standard.”

Eye lashes – we first applied a heavy amount of Maybelline eyeliner above and below lash lines. This was followed by oversized Ardell ‘Studio Effect Wispies’ false eyelashes that required Duo eyelash glue.

Lips – I LOVE wearing lipstick! Mel used Merle Norman lip liner to outline my lips and then colored my lips with a generous amount of Burgundy plumping lipstick. I’m sure Dutch would have preferred true ‘cock-pillows’ for our date. Mel used a lip liner that was a shade darker color than my lipstick and made my lips appear fuller.

The wig - It was time for the wig we had agreed upon. I had chosen the blonde wig.

With Vivian’s help I tucked my shoulder length atop my head and pulled a silk mesh wig cap on. The cap would make my wig more secure and make wearing my new ‘hair’ easier. Vivian began fitting the wig to my head.

My wig was a shoulder length layered style with blonde highlights, bangs and a bit of a flip; Mel styled it so my dangling chandelier sequin earrings would standout. After a minimum amount of brushing and styling they said it was time for me to see how things looked.

(This is the Peacock Blue blouse I wore for my date with Dutch.)

When I got out of the salon chair we took a few minutes and a glass of wine to relax before beginning to get dressed in the manner that Dutch had specified. V & M took photos.
Foundation garments

My 40 D long line bra was Spandex framed with comfortable 1 inch camisole straps and three inch 360 degree waist panels to prevent riding up. My big tittie breast bra had 8 hooks in the rear that were beyond my ability; I needed help in getting it hooked up. I knew I could never escape its snug confines by myself; feeling ‘trapped’ was naughtily erotic. Would Dutch release me from my feminine bondage? How could we have sex? Must I sleep with them on? Such thoughts were troubling. My bra and girdle were black.

Girdle: My extra firm open-bottom girdle with 15 inch side boning was a blend of nylon and Lycra with a power mesh tummy band. A hidden right side zipper made putting it on easier. While the floral lace accents on the front made me feel sexy the stiff boning on the front, rear and sides that would prevent ride up, made me feel trapped in the firm grasp of an erotic fetish! To avoid ruining my acrylic nails Vivian helped me with my girdle. Would Dutch be so kind in the morning?

For me overly constricting foundation garments were like self-inflicted bondage; there was no way that I would be able to release myself from their tight grip; I would be helplessly trapped and at the mercy of others; I found the situation to be unexpectantly arousing; I yearned to have a moment in which to seek relief.

Blouse – My blouse was a Peacock Blue satin with long sleeves and a button up collar and sleeves.

Skirt - a shiny black PVC above the knee mini skirt; skirts were fairly short because they said I had great legs - a contrasting silver Concho belt was good accent.

Boots – Finding stylish size 11 knee high leather riding boots with a 4 inch heel was a problem. By sheer good fortune we found a pair of knee high Bernini pointed toed dress boots in my size on-line. Their 3 inch heels would make my night much easier than 4 inch spikes.
After I was fully dressed Vivian and Melanie escorted me to the shop’s full length mirror; I marveled at my refection. I hoped that Dutch would deem me beautiful and worthy of being fucked. I wished he was beside me staring into the mirror because the process and my image had put me in the mood to be with a man. I struggled mentally to minimize the spontaneous erection that screamed for release.

More photos and a video were taken. Vivian said that photos of the three of us would make excellent Christmas cards and/or marketing brochures.

Departure

I was embarking on an important mission whose success was critical to the future of Vivian, Melanie and myself; I was determined to bring my “A” game. If being an actress, slut or fellatrice would contribute to the mission’s success it was ok with me.

My luggage consisted of a medium sized suitcase, a small suitcase and an empty wig case. My makeup bag, ribbed condoms, mouth wash, makeup remover and lube were in the bag. The limo driver put everything in the trunk.

Vivian, Melanie and I entered Dutch’s limo at 1 PM. We helped ourselves to the open bar in the back area and made dirty martinis. “Driver, be so kind as to not arrive until we’ve finished our second beverage please” I asked.

Arrival

We three ladies made nervous conversation about inconsequential things in an effort to remain calm. We had just finished cocktail number two when the driver pulled under the Fairmont portico and parked. We could see Dutch waiting at the front entrance. Our driver walked around the limo and opened our door; “Ladies you have arrived” he announced. It was 2 PM.

Before stepping out of the limo we finished our cocktail, held hands, closed our eyes and thought good thoughts for a moment; we prayed for things to go well and for me to be safe. As we were exiting the limo Mel said, “Maxine, I put a half dozen Valium in your purse just in case you need one.” I smiled and said, “You’re so sweet… thank you.”

I grabbed my purse, our driver extended his hand and assisted the three of us out of the limo; he retrieved my luggage from the trunk and loaded it on a shiny brass hotel luggage cart. Knowing that two of us would be returning home our driver closed the door and waited unobtrusively nearby.

The limo driver had called ahead and Dutch greeted us at the limo drop off area. We wanted him to be aware that I had friends that were looking out for me. We girls faced each other, spoke briefly and kissed good bye as Dutch watched. Viv and Mel would not get back into the limo until I was whisked inside the hotel. Just before entering the hotel I turned and waved to my friends and business partners.

While my luggage was being brought to hotel check-in Dutch took the opportunity to inspect the ‘goods’ he had ordered. “Very nice” was his comment. “Same for you” I said; Dutch was not an unattractive man.

Dutch hugged me and gave me a prolonged kiss to establish that he was the ‘top’ in our relationship. His hands evaluated my butt and the firmness of my bra and girdle as he held me tightly; I dared not resist his amorous intentions. I was curious as to how this situation would play out. I cupped his crotch, felt his firmness and kissed him back with equal passion. Dutch seemed surprised at my touching.

He looked me in the eye and said, “Your nails are nice”. I smiled, pressed my pudenda against his leg and lightly traced the length of his crotch bump with my acrylic nails. Perhaps getting Dutch to turnover his salon to us may not be as difficult as we three girls had thought. ‘Whatever it takes’ I thought.

He smiled lasciviously and quipped “We’re in for an exciting night, Peaches”. I nudged him sharply with my elbow and sternly said, “My name is Maxine!”

With his arm around my waist and one hand cupping my ass Dutch steered me to the front desk. The Fairmont had an impressive aura of opulence. I knew the suite would be equally pleasing as would the king size bed.

Check in

At check-in a very well dressed Assistant Manager directed one of his staff to bring my trousseau and Dutch’s bag to our suite; from a distance the Assistant Manager looked vaguely familiar to me. His voice brought back distant memories of years past. I smiled at the recollection and asked, “Are you going to summer camp this year?”

Taken aback by my odd question the man turned to face me; a lapel name tag confirmed he was my “Troy” from summer camp. It took a moment for Troy to see through my makeup and recognize me. “Maxie, I still have dreams of you!” he exclaimed. His smile told me that it was true.

Before Troy could come from behind the check-in counter for a hug and a kiss I discretely pointed at Dutch and gave Troy the ‘hush and be calm’ gesture. I mouthed a silent ‘I’m with a date’ admonition, winked and blew him a subtle kiss. Troy nodded his acknowledgement, flashed me a smile and winked back. He also licked his lips.

While looking directly at me Troy asked in a professional manner, “Is there anything else we can do for the lady during your stay with us?”

“If we need room service later will it be you that brings champagne to our room?” I asked.
Troy handed me his business card; “Here’s my direct phone number Maxie. Just call.” I nodded my head, took his card, and placed it my purse.

As Dutch and I made our way to the trendy hotel cocktail lounge I wondered if Dutch would find having a third person in our suite ‘over-the-top’ erotic enough to secure his signature on the salon transfer document.

Over cocktails and a bar menu sampler platter of snacks I conveyed to Dutch the special skills that Troy had. Halfway through our second cocktail Dutch decided to cancel our restaurant reservations and have room service bring dinner to our suite. “I’ll make the arrangements now” he said.

Prior to leaving for the front desk Dutch (so he could arrange dinner, champagne and maybe Troy) leaned over and gave me a prolonged kiss on the lips; he made a point of using his tongue. Meanwhile, under the table, his hand sensuously stroked my inner thigh and panties; if he was feeling for my boy-bits he struck out. I gripped his probing hand between my legs and kissed him back making sure to use a bit of tongue.

When I was finished kissing him I released his hand and as coquettishly as possible purred “Hurry back, Daddy.” When Dutch finally excused himself and left to make our arrangements I could clearly see that his boy-bulge was definitely more pronounced. I was well pleased at my effect on him. ‘Act One’ was over.

On purpose I was reapplying my lipstick when Dutch returned. I greeted him with, “I’m trying to stay pretty for you, darling.” He sat down and we sipped our Cosmopolitan cocktails. Dutch said we would order our meal downstairs at the restaurant and then go up to our suite to get “better acquainted” while we waited for room service. “After the wait staff clears our suite I’m having a couple bottles of cold Champagne brought up. Troy says you’ll recognize the vintage”.

Jump forward

After kissing like newlyweds in the elevator we got to our room around 4 PM. When our food arrived around 5 PM Dutch had to put his pants on before answering the door; I had to freshen up my makeup and lipstick.

We were finished with our steak and lobster dinner by 6 PM; my girdle and long-line bra kept me from overeating. Less than 30 minutes finishing our meal all dinnerware had been picked up and our suite was back to normal; the night was still young. Not long afterwards there was a knock on our door. A muffled voice on the other side of the door announced that our Champagne had arrived.

I looked at Dutch, flashed a pouty kissy face smile and shrugged, “Before you open the door you need to ask yourself how much of an ‘over-the-top’ evening do you want Daddy?” Dutch smiled at the nick name I had called him. This was a ‘tell’ that I would use again. I would play the submissive ‘young twink’ role to his ‘I’m the top’ dominant Alfa male façade.

“While I am explain things to room service go put on the negligee and peignoir set I bought for you. It’s hanging in the closet. I think you’ll approve. Take your time; touch up your makeup while Troy and I have a talk.”

As I headed to our bedroom Dutch added, “Leave the pantyhose on.” His words were not a request. As I was doing what Dutch said I tried to recall Troy’s special desires.

I was thrilled with the sexy black boudoir ensemble that Daddy had bought for me; there was also a delicious pair of matching mules with a five inch heel. I gleefully put them on and minced to the vanity mirror for makeup touchup. The way I had to walk in them made me feel like a newly minted simpering Sissy. Perhaps once I get used to them I’ll walk as easily as an experienced pole dancer.

I heard the popping of the champagne cork which was my cue for me to return to Daddy’s presence. When I went to the sitting area of the suite I made a point to play the role of a coquettish ingénue. I was in heat and my ‘cauldron’ was bubbling nicely. Even though I knew that Troy and Dutch would have their way with me I felt I was in control. ‘Act Two’ was over.

Jump forward

Shortly after 3 AM Saturday morning I took a break from very steamy activities. I went to the living room of our suite and called Vivian.

V - Why are you calling so early? Are you okay? Do you want us to pick you up right now?

Me - Good news, the ‘Maxie volcano’ erupted, lava flowed freely and my ‘rear access’ panties were a big hit with everyone; I’m now your Facilities Maintenance Manager for two salons!

V - How did you get him to sign?

Me - First I had to repeatedly take and pleasure his 8 inch penis in every way imaginable and let him watch Troy thrust into me with a ribbed condom. Dutch would only sign the contract if I agreed to comply with one caveat. He’s a sexual beast for god sakes!

V - And what my darling have “we” agreed to?

Me - Daddy says I must spend two weeks with him as Maxine, in normal makeup and clothing, once a year.

V - He actually asked for that!? Viv exclaimed.

Me - No Viv, that was my idea. Dutch is a very generous pussy cat; unlike some dates Daddy was gentle with me. He wants me to meet a few of his Florida friends.

Wait until you see the black satin negligee, peignoir and mule set he bought me! Daddy made me keep my pantyhose on! (I must have sounded like a ditzy teenage girl.)

Me - I’m sore in places that have never been sore before, my jaw aches, my lips are chapped and I’m seeping! Men can be so demanding when they’re in the rutting season.

V - Oh?

Me - It’s a long ‘over-the-top’ story; I’ll explain everything when I get back. My ‘rear access’ panties and crotch-less pantyhose were a big hit! I was able to get Dutch and Troy into pantyhose; they loved the feel of their nylons rubbing and slipping against each other; it made their man-on-man humping sessions more erotic.

We drank Champagne, showered, soaped, sucked and fucked to our hearts content. I had to remove one acrylic nail to help seal the deal.

V - Let me guess… right hand, middle finger?

Me - Exactly! It was the only safe way I could safely rub their prostate glands. My prostate got beautifully massaged in a way that didn’t involve fingers and I enjoyed another anal orgasm from Troy; my crotch less panty hose and rear access panties were a big hit; we were all glad I was wearing them.

V - Who is this Troy person that you mentioned?

Me -Troy had a lot to do with getting Dutch to agree. We wanted ‘over-the-top’ and Troy was definitely ‘it’; you might say that Dutch got a ‘twofer’. Seeing Troy giving head to Daddy was so damn erotic I thought I would burst! I’ll share the details with you and Mel when I get home.

V - Anything else we should know about Missy?

Me - Dutch and Troy removed my fake breasts and girdle to give them access to my boy-bits and tits; both were nursing my breasts at the same time! It’s a good thing that Troy brought Viagra because they both want to be on the receiving end of a ribbed condom while wearing crotch-less pantyhose.

V - Will you be able to give them what they want?

Me - It’s been awhile but I’m sure it will all come back to me. Besides my body parts and I are anxious for a new type of action; being the ‘top’ after so many years will be fun!

V - What time are you coming home on Sunday?

Me - I’ll let you know Monday morning. In the meantime Troy’s arranged for new bed sheets and a room service champagne brunch for later today and then Dutch is taking us to a swanky dinner tonight. After that I need my beauty sleep, right?

V - Are you sure Dutch didn’t say you all were going to a “skanky” dinner?

We laughed at her humor. I hung up and lay back on the bed, two wrapped condoms in my hand, and took time to reflect on how very odd life can be.

Troy and Daddy’s voices calling for me from the bedroom brought me back to the present. I was going to give them both a good “ribbing”; Troy was going to be my bitch again! Sharon from my young girl days was right, I was doing fine! ‘Act Three’ would be starting soon… or would the next few hours be considered an ‘Encore’?

END (of a beginning)

Special thanks go out to the REAL Maxine that inspired this story. “Stay pretty Princess, your Sorority Sister in life, Donna T.”

To read my other 35 CD/TV/TG stories do a 'Search by Author'. Several are PG, sentimental, promote acceptance and feature the door-to-door Avon Sales Ladies from years ago. Take a walk at Paradise Cove or enjoy a Womanless Beauty Pageant. Be sure to leave a “hello” in the comments/review area. Thanks; stay pretty! Donna.