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Indeterminate sentence - Jenny & Stacie (Chapter 1)

Author: 

  • Donna T

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • EXTREMELY EXPLICIT

Publication: 

  • Serial Chapter

Genre: 

  • Crossdressing

Character Age: 

  • College / Twenties

TG Themes: 

  • Caught with Consequences

TG Elements: 

  • Estrogen / Hormones

Other Keywords: 

  • graphic
  • NOT work safe
  • Forced

Permission: 

  • Posted by author(s)

(Chapter 1) - Caught, convicted and waiting. There was no jury, only a panel of three women to determine your fate here; an indeterminate fate. 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’ you could expect was intercourse we were told.

(This story is ADULT fiction. There will be four chapters. Comments are appreciated.)

Prelude – Caught, convicted and waiting: "My name is Jenny"

Days 1 – 14

There was no jury, only a panel of three women to determine your fate here; an indeterminate fate. If you were pulled before this tribunal your fate was already sealed. Even if you were not “guilty” you would not like the outcome. 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’ you could expect was intercourse we were told.

It was all a matter of the amount of time that you would be held. And that involved recruits, aka ‘sluts in training’, obeying ALL the rules and complying with the ALL program. Emphasis on the word ALL. If you transgressed you would be in for a very long, indeterminate, stay.

The hormones, testosterone blockers, inoculations and ‘vitamins’ began immediately on day one. You were held in a traditional jail for two weeks while they gave you tests, examined you and took all your measurements like height, weight, shoe size, pant length. It was like going to a tailor to be fitted for a custom suit. It took them a week to figure out where they would put you, what program you’d be on and endless amount of similar bureaucratic red tape. The meds and shots were daily. No haircuts were permitted. Most ‘recruits’ were a bit shaggy looking when we arrived.

Program selection criteria

There were two weeks of post sentencing tests, interviews and evaluations that determined which program you would be placed in. Other criteria include: Under 6 foot, less than 150 pounds, open and willing to accept new ideas, not anti-homosexual, ages 18 to 28, a high femininity profile, NO inclination to violence, above average intelligence, and several other factors. A candidate for this program had to be deemed ‘salvageable’ to the ‘correct’ way of behaving.

It was during this 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, avoided the other ten to fifteen ‘strangers’ that surrounded us. Some of these ‘others’ looked less than nice… rough and scary.

During free time the ’fab four’ talked about sports, favorite movies, school, jobs and how we came to be in this predicament. One topic 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.” Some of us snorted in agreement. Steve volunteered “That was 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 John. “Well? What’s you guys stories?” I said “Now I don’t feel so stupid about being found wearing panties…but mine were beautiful French cut, peach colored, beauties with just the right amount of lace. The only thing is that they were mine.” Nobody laughed. We turned to hear what Jack had to say. “I feel stupid that I got caught. And that I wasn’t wearing underwear. I was going commando style. The good news for me is that the rubber glove rectal exam actually felt good.” The other’s gasped in disbelief.

In general the consensus was that no one wanted hard time in a prison: anything but that. Prison was a scary place they agreed.

“You hook my bra and I’ll hook yours”

The night before being transferred we were each given a bottle of bright red nail polish. “Here you go ‘ladies’, you’re leaving here tomorrow morning. If you don’t want to be left behind you need to paint your nails tonight; all ten of them. Your painted nails are your tickets out of this place. Be sure to bring the bottle with you as you WILL need it at your destination.” I took the bottle and immediately began shaking it in order to mix the polish. The aroma of nail lacquer soon filled the air.

I quickly had all my nails done and was blowing on my finger nails to dry the polish. I think I did a pretty good job. A few of the others were struggling to paint their toe nails. I offered to help in order to get the job done. I finished painting the toes of Steve and Rod. I stood up and stretched. “Ok, we better get some sleep.” I walked to my cot and laid down. I held my hands at arm’s length and admired the pretty color. I took a final smell of the fresh polish and closed my eyes. I was soon asleep.

Day 15

Myself, (soon to be called Jenny), Steve (soon to be called Stacie), Rod (soon to be called Rose) and Jack (soon to be called Jackie) were put on the jail transfer bus very early the next morning. We didn’t have to remove our shoes and socks and show our painted toes but everyone’s finger nails were inspected before we could board the bus. The other ‘recruits’ remained nameless to us. “Don’t make eye contact’ was our philosophy. The fact that our foursome had ‘bonded’ was noted, and reported, by our ‘guards’. Our friendship was to come in handy in the near future.

We were bound for an unknown, but far away, location. All we were told was that we were in a very exclusive program and that we should feel damn lucky.

Day 16

It was an overnight ride. The bus arrived early in the morning at a very remote area that was flat and had very few trees. We filed inside a sinister looking building and were told to wait in a large dayroom. The dayroom was furnished with a large high school looking table and bench combo (like in a school cafeteria) that was for meals. There was a large TV and a couple of chairs off to one side. Rod nudged Jack and pointed out three security cameras high on the walls.

We were met by a group of five women. A stern looking older woman stepped up to explain The Program. She was to be addressed as Matron we were told. “This facility is called The Nest. It can be comforting or it can be harsh. The choice is yours” she said. The explanation began.

Since The Nest was an experimental quasi “legal” facility, us ‘offenders’, were being held in a private location. Secret AND remote is a more accurate term.

We were all being kept, against our wills, at this secure, secret facility nicknamed The Nest. Oh, God… we all wanted to be kicked out of The Nest as soon as possible. 10 months was the minimum time IF you met their reeducation “goals”. Some ‘inmates’ had been in The Nest for over a year. We had all, allegedly, been disrespectful to women in some way and had been sentenced to indeterminate sentences. We were to learn and atone for the errors of our ways.

All of us had reportedly denigrated, disrespected, abused, raped, and/or used women. There were lesser “offenses” and worse crimes that had brought us all here. We were to be shown the errors of our ways and reeducated… we were to walk a mile (or ten) in the high heels of the females we had reportedly offended. We were to be kept until we got “it” right. “It” being empathy, true regret, atonement, and respect for femininity in general and have genuine remorse for whatever we had allegedly done… even if you had done nothing!

“Better get with the program!”

The program was nothing more than a very comprehensive forced feminization and mind altering program that could go on for a very long time. Degradation and becoming submissive were key elements of The Program. So was having a high level of intimacy with your roommate and the other ‘girls’. Your length of incarceration depended on your degree of program compliance hence the term “indeterminate”. Other factors that affected your release date were determined by your degree of femininity; your ability to become an ordinary woman functioning as a good citizen in the real world. And of course there was that ‘intimacy’ factor to be considered. To encourage intimacy we were given special ‘vitamins’ and food seasonings. They made you want to rut. They increased your libido substantially.

The process begins

We were stripped naked, given a pair of ‘granny’ cotton panties, and assigned a room and a buddy. Two ‘girls’ were assigned to each room. We were reluctant ‘recruits’ but were expected to help each other with whatever was required during our retraining. We would be ‘mates’ in the literal and physical sense of the word.

WE were all ‘girls in training’ and were expected to evolve to looking and automatically behaving and sounding like women before release from The Nest. Halfway homes were in place to help us transition back to the real world. We could return to the male world or we could choose to continue our learned feminine ways.

In the Beginning

All ten of us ‘recruits’ were assembled in the dayroom. We all were given name tags to be worn for the first day. I, John, was now Jenny. Rod became Rose, Jack became Jackie and Steve was to be Stacie. There also was a Fannie, a Beth, a Tracie, a Jewel and others. Since we were all naked we all sported one pair of pink, with tiny flowers, cotton ‘granny’ panties as we waited to be told The Rules. We were all looking around nervously sizing each other up. We knew we would be paired with a ‘girl buddy’. Some recruits were pretty scruffy and some were tattooed and mean looking. Many were visibly quivering and silently crying, trying to not make eye contact with anyone. My eyes shifted everywhere.

An intercom advised us to stand up and be quite. A door opened and a half dozen very attractive “girls” entered the dayroom. All five were dressed like models about to go on a date. Their makeup and jewelry were perfect and they wore four inch black leather pumps. The only real difference between them appeared to be their earrings. Some wore rubies, some wore two inch gold hoops or pearls, one had double ear piercings and one appeared to be wearing three diamonds earrings in each ear; three piercings in each ear! She must be someone important I thought. It was as if the earrings determined rank or status.

The head Matron wore a ‘no nonsense’, prison guard looking, uniform. She wore only basic makeup, black closed toe shoes with maybe a one inch courtyard heel. She also wore a black “cop belt” that held a walkie-talkie, a taser, hand cuffs, and something that might be a chloroform spray. The remaining five “girls” that came in with Matron stood behind Matron and were lined up shoulder to shoulder. They looked straight ahead. They were all very attractive. Some of us new ‘girls’ were showing their appreciation of their beauty in subtle, non verbal, ways. Some granny panties were beginning to bulge.

Matron cleared her throat and began in a terse, strong voice to explain what was going to happen to us ‘girls’ over the next months and possibly years.

“We have a program and a set of rules that you WILL live and abide by. There are no excuses. The time you spend here is entirely up to you. To help get you through the program you will be assigned a roommate. Your roommate is what we like to call your ‘girl buddy’. You WILL need her at some time if you are to survive and leave The Nest”.

The use of the pronoun “her” sent a low grumbling among the recruits.

“Silence I said!” the Matron bellowed. “You must pay attention. You have all been found guilty of maligning women in one way or another. You are here to atone for those mistakes by becoming feminized yourself. Our program goes through several phases. So will you all. And EVERYONE will abide by The Rules! Is that perfectly clear?”

“Immediately after your sentencing you were all deloused, showered and inoculated for a wide variety of diseases. The injections included the start of HRT and testosterone blockers. You may experience mood swings and a few other side effects. Your tits may itch and they WILL grow. We call that ‘cup size’ as in bra cup.”

“Everyone was given a thorough medical exam and everyone was given in-depth blood tests. This explains why, instead of having fourteen recruits, that we now only have ten ‘girls in training’. 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 go through ALL the programs and all of the MANDATED requirements.”

Stepping back a bit from the newbie’s the matron said “Take a very close look at each of these lovely ladies lined up behind me. They are all genetic males. All have been, or still are, in our program. Notice that Miss Diane has three diamond studs in each ear. She has completed all phases of our program. She could transition (no pun intended) from The Nest to one of our half way homes. She has chosen to remain with us at The Nest to help and assist us indefinitely. Miss Diane LIKES the security that The Nest provides. Maybe you will too.”

Matron turned to face her “girls”. “Martha, will you please hand out a copy of The Rules to our new ‘girls’?” Martha also had three piercing. She wore gold 2 inch gold hoop earrings at the bottom, ruby in the middle and a smaller sapphire one above that. She also wore several bangle bracelets that jingled pleasantly as she passed out The Rules. As Martha went through our small group everyone took a close look. Some of us went pale as it became clear what was to happen to us all.

Martha was very pretty, well endowed and was dressed like she was going on a date. Low slung blouse, black patent leather pumps with 4 inch heels, ample cleavage and breasts that appeared perfect and she smelled heavenly. Her lipstick was bright red and her eyeliner and eye shadow appeared nice but a bit heavy. Her eyelashes looked like a fashion models. Some of us clearly were beginning to tent out our granny panties. This did not go unnoticed by the Matron or by Martha. In fact Martha broke into a beautiful smile. It was as if she knew something that we didn’t.

“Listen up you ‘girls’ I see those crotch bulges.” The Matron said. “Let me assure you that VERY SOON you will not have to worry about such an affront to women again. All of you ‘girls’ were immediately placed on testosterone blockers and began a controlled regime of HRT… that’s Hormone Replacement Therapy to those that don’t know any better. This began immediately following your sentencing. Again, this may any itching you may be having with your tits. By the way Martha is a C cup and has three ear piercings.”

“Be advised that NO one leaves The Nest with less than a B bra cup.” Matron flashed a sinister smile and continued “Yes, everyone one of you will begin wearing an A cup bra in about 90 minutes. B cup is the minimum to leave this place. There may be extra credit for attaining a D cup or larger. In the meanwhile we provide you fine silicon prosthetics until you don’t need them. That day may be sooner than you hope. You WILL become fully and naturally endowed.”

Matron turned back to her girls and told them to leave. “Miss Diane, I want you to leave too but you are to go to the video monitoring room. Be sure to turn on the audio recorders, especially in the recruits rooms. Stay alert and send help if you think it’s warranted. Make notes of any infractions”. Miss Diane immediately complied.

Turning to face us Matron announced “Yes, you ALL will be monitored at ALL times, 24/7 and that includes the bathrooms, hallways, toilets, showers, beds and dayroom. You will now be paired off and then go immediately to your rooms. There will be a stack of clothing on your beds. Your vanities will be fully stocked. You WILL all be wearing red lipstick the next time anyone at The Nest sees you. If you don’t comply you don’t eat. And we have even harsher methods that you really don’t want to experience. Am I clear?”

“You have lots to read and lots to do. First on your agenda will be to shower and shave ALL the hair off your bodies except your eyebrows and the hair on your head. That means your pubic areas… front AND back. You’ll probably need your roommate to give you a hand. You’ve not had a haircut in weeks and it’s reaching a manageable length. We will schedule you with a beautician in the near future. In the mean time we have provided you wigs.”

“I will pair you off, assign a room number and you’ll IMMEDIATELY hold hands with your roommate kiss each other ON THE LIPS and exit down the hallway to your room. Did I say kiss? On the lips? I damn sure did! On the lips. What better way to introduce yourself to someone and get to know them better? You better get used to it now. It will help with what is coming later easier to endure. When you get to your room you’ll find a pile of clothes and sleepwear lingerie on your bed. There will also be instructions on your beds. Bring your Rule Book. And you better read it twice.”

“From this point forward you will only use your fem names. I’m to be addressed as Matron. If you see Diane again she’s to be referred to as MISS Diane… believe me, she has EARNED the title and your respect.”

“I’m going to begin to call names and rooms. Hold your partners hand and wait until all rooms are assigned. I’ll tell you when to kiss. When that’s over I’ll dismiss you to your rooms. This first kiss doesn’t have to be long and passionate but it damn well better not be a brief peck. As you get to know each other some passion will develop. Especially as the hormones and blockers kick in. In everything you do while here you are to treat each other AND staff with respect.”

The Matron began the roll call

“Jenny (John) and Stacie (Steve), room one.” I looked around, found Stacie and immediately took her hand in mine. Like mine, Stacie’s 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. Everybody got that? Good. Now turn and face your new buddy. Kiss her ON THE LIPS until I count ten. Start now.”

We found out later that it was not an accident that our foursome was assigned to be the other’s roommate. The Nest authorities had been notified of our budding friendships while we were awaiting our fate; it would be easier for us to acclimate and accept The Program if we knew someone.

It seemed like an eternity until we were told to stop. “You all did well. When you’re wearing lipstick it gets more enjoyable. Think of it as colored Chap Stick. Continue to hold hands and go to your rooms now. Report back here in ninety minutes for your first inspection dressed as the instructions say. A late breakfast will follow. You’ll have time to talk and get acquainted. You’ll then go back to your rooms to study and learn The Rules. Don’t fight your hormones. Go with the flow and your stay here will go smoother for you. You have ninety minutes. Breakfast waits for no one. Go!”

We all walked down the hallway, holding hands and entered our rooms. All of us were experiencing shock of some kind. WE were all dazed.

The rooms

Each room was a studio apartment with two double beds, a couch, love seat, a Queen Ann chair, two mirrored (and very well stocked) vanities, a bathroom with a large walk-in shower that could easily accommodate 3 people, a tub, toilet (with bidet) and a TV. The rooms were decorated in feminine motifs. There were two way observation mirrors on the walls. And there were several security cameras in the corners of the ceiling and over each bed. Each had video and audio recording capabilities.

An intercom in the ceiling allowed the staff to make announcements, provide instructions and encourage the ‘girls’. And the intercom was one of several conversation monitors. Staff could hear you complaining and they could hear any moans of carnal delight. Your progress could be easily tracked and recorded. You had goals to meet. The arrangements had been well thought out.

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 shaking. I thought she may collapse. Out of instinct I gave Stacie a hug to calm her down. That’s when I began crying too. Together we cried and mentally tried to digest what we both were going to have to endure. And we hadn’t even read The Rules yet.

Gathering a semblance of composure I broke our hug and held Stacie at arm’s length. “Hold on, Stacie. Calm down a bit. It’s going to be ok. We can get through this together. We just need to work as a team and think this through.” Out of reflex I pulled Stacie into another embrace to comfort her and gave her a gentle kiss to her cheek. I looked around their room, saw a sink and went for a glass of water for Stacie. I came back with a glass of water. “Here, take a sip. We’ll be ok. Come sit over here.” I guided Stacie over to a pair of chairs near the sink area and helped her sit down.

The instructions

We read the information silently. These instructions were for tonight only. New instructions would be issued in accord with the Program agenda. Tonight’s requirements were:

“All clothes have been selected on the measurements we took of all recruits after sentencing. All clothing and accessories fit.
Shave completely. Douche yourself rectally, deeply and completely. You need to get used to this. Use a moisturizer for any body part that you shave. Become familiar with the contents of the vanity, closet and the room. Familiarize yourself with the make-up and feminine products that are in your vanities and medicine cabinets. Tonight will be simple. Change out of the cotton panties. From the skin out you are to dress in modern female clothes. This means nylon panties of your choice and a matching camisole, a properly adjusted bra with the gel inserts in proper place, a matching skirt and blouse.

Your outfit is to be color coordinated. For footwear you can choose sandals or Mary Jane style shoes. Your choice. They must have at least a two inch court shoe heel. Use nylon foot peds if you want. Nylons and/or panty hose will be required in the future but not tonight. You are to wear basic make-up which includes mascara, lipstick and blush. You’ll need to become familiar with makeup removal and skin care. There will be classes on this and related information can be found on your in-room TVs.

Sleepwear will be baby dolls, satin pajama set, Shorty night gown or a chemise. There will be no sleeping in the nude.

Always carry these items in the provided hand bag. Include a hair brush. Select one of the two wigs that we have provided. You will use them until our hair grows out. Be sure to apply one of the four perfumes on your vanity. You each have your own vanity that is fully stocked. Your jewelry MUST include clip on earrings for now, two rings of your choice, one bracelet, a wrist watch, a necklace and a gold anklet. See you at inspection. Breakfast follows immediately.”

Stacie looked up and was about to burst into tears again. I stopped her by just saying “Shhh…don’t cry Stacie, this is easy. It could be much worse. You go shower and shave first. I’ll select and layout our clothes to save time. Call me if you need help in those… errr… awkward areas.”

“Take some deep breaths Stacie. Let’s think this through. We’re on a time schedule.” I got up and retrieved the instructions that were on our beds. The room was very cool and I had the presence of mind to grab pink nylon chemises from the pile of clothes on our beds. “Here pull this on for now. It’s cold and we have to get going. Here are our instructions. We need to read them now.” I handed Stacey the letter.

Flashback 1

Months after arriving at The Nest

I sat pensively on the edge of my bed, nervously twitching my nylon clad foot which in turn caused my black 4 inch high heels to slip on and off my foot. I was wondering WHEN my new ID would arrive.

I glanced at my blood red nail polish; ‘Cherries in the Snow’. Each nail had been grown and shaped to the ½ inch minimum extension as specified in The Rules. I knew my toenails were fine because Stacie had taken care of that for me. It was one of many mutual aid routines we had established in order to survive and end their ordeal as soon as possible. “You hook my bra and I’ll hook yours” so to speak.

Playing for the cameras I stood up from my bed and made sure to pull her my dress down in a well rehearsed lady like fashion. The hem of my dress was about seven inches above my knee and I didn’t want to expose my garter belt tabs. I walked over to a full length mirror and gave myself another inspection. My lips were perfectly done, my mascara was double coated and curled, my eyeliner was in order and my eye shadow went with my complexion. Out of habit I made sure my necklace and gold anklet were in position. I touched up my lipstick, glancing towards one of the camera monitors. I applied a light amount of Cashmere Mist perfume in all the right places. It all looked so natural. By now it was second nature to me. Perhaps, in reality, it was third nature. I chuckled at the thought.

I took a deep breath and went to a Queen Anne’s chair, sitting down, instinctively remembering to smooth out my dress as I sat. I crossed my shimmering smooth legs just like Sharon Stone had done in Fatal Attraction.

Picking up a fashion magazine I took my time in flipping the pages. I was in a hurry but I knew I wasn’t going anywhere quite yet. Stacie was out in the day room whiling away her time, chatting with others while painting her nails and listening to TV. So I was alone in our room.

While waiting and trying to be as demure as possible I let my mind wandered back to our first day days at The Nest. It seemed like such a long time ago.

I smiled and giggled as I recalled that first day with Stacie. Stacie had only been in the shower for about ten minutes before I got her call for help. It seems there were two areas of shaving that Stacie was having difficulty with. The most difficult was her backside. She just couldn’t gain access to her rear crevice. She couldn’t separate her buns enough to get a razor onto the area. “Jenny, could you help me out here? I don’t dare fail inspection. I can lather but I can’t shave. I’ll do you a favor sometime. Please.” She begged.

I had no choice. I picked up the Gillette Fusion razor and told Stacie “Ok, I’ll do it but you definitely owe me. Apply more Foamy shaving creme, bend over, squat and spread your cheeks.” Stacie did as she was told. Now there was clearly enough room to allow access for the razor. As delicately as possible I made several passes with the razor. Problem solved. Although not intentionally looking for it I was surprised at how clean and oddly symmetrical Stacie’s rear ‘rosebud’ was. Stacie had obviously thoroughly douched as instructed. It amazed me how Stacie’s sphincter reflexively puckered and contracted with each stroke of the razor. It was mesmerizing to watch.

Obviously blushing Stacie said “Jenny, I also need help up front too. I’m afraid of using a razor so close to my penis and ball sacks. It keeps hanging in the way. Sorry” she said. “For some reason it doesn’t get hard and doesn’t give me the angle I need to do the deed. I double owe you.” I rolled my eyes and said “OK, but I’ll only do this once and you DO owe me big time!”

Stacie had gotten rid of most of her pubic hair but there were clearly parts that needed help; the base of Stacie’s cock and most of one testicle. I rinsed the razor, applied Foamy where needed and grabbed Stacie’s shaft. God it felt odd. All squishy and limp. I had never held another man’s penis. It did not get hard and didn’t feel as creepy as I thought it would. I could feel a stirring in my cock. I expertly shaved all around the base leaving Stacie’s cock looking like a hairless baby. The single ball sack was easily shaved clean. I may have made a few unneeded passes with the razor; it was a good excuse to retain hold of Stacie’s dick. I recall giving it a squeeze before letting go.

I put the razor on the shower shelf and told Stacie “Next time get a depilatory; some Nair. I’m not doing this again. Now get out of the shower as I have things to do. And where did you put that douche bag and are there two nozzles?” Damn, there was only one nozzle.

I ordered Stacie out of the shower reminding her they were up against a deadline. “I laid your clothes out. Go dress yourself. I’ll hook your bra if need be. Go!”

I stepped into the shower with the douche bag already filled. Be prepared. I inserted it and cleansed my bowels and rectum thoroughly. It added to the stirrings I felt just a bit ago. Composing myself I made sure to clean the nozzle and return it to the shelf.

All of this was noted by Miss Diane via video. ‘Subject Jenny has no qualms in touching Stacie’s penis or rectum or in douching herself. She seems to be a special slut in the making. I suggest increasing both her estrogen and testosterone blocker doses.”

Fifteen minutes later I was inwardly and outwardly cleansed and shaved. In addition to using the moisturizer I took it upon myself to use after bath scented dusting powder all around my crotch. ‘That’s a pleasant smell’ I thought. This too was logged by Miss Diane.

After drying off I entered the bedroom. Stacie was 90% dressed but as expected she needed help with hooking her bra and positioning her gel inserts. I took care of the details and even shortened one bra strap to its correct length. I also took the liberty to gently plucking her nipples. Yes, they were capable of getting erect.

I quickly got fully dressed and hooked my own bra using both hands behind my back with no assistance. ‘Very feminine movement’ Stacie thought.

I took charge of my own make-up applying blush, lipstick and mascara. A big surprise to Miss Diane, I found out later, was when I picked up an eyelash curler and crimped my lashes into a more feminine look! ‘Perhaps we have a ringer in our group. Jenny seems a bit too familiar and at ease with many aspects of feminine dress and procedures’ was the next entry Miss Diane made into my file.

I looked into the vanity mirror and checked my appearance. “Not too bad” I thought. I motioned Stacie’s to sit at the vanity. Stacie’s only problem was using the mascara wand. Again, it was me to the rescue. I even used the eye lash curler on her. “Don’t worry you’ll get the hang of all this quickly enough” I said.

Glancing at the clock I saw we had ten minutes to make inspection. Grabbing both of our wigs we soon had them on and combed enough to be passable. We both had the required jewelry on and were stuffing our hand bags. I liked the way the anklet completed my outfit. The clip- on earrings are a bummer. They hurt! ‘Maybe we’ll get our ears pierced like Martha and Miss Diane’ I thought.

Stacie opened the room door and we were about to report for inspection 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.

We gave each other a mini inspection and all seemed ok. Stacie mentioned “I really like your cleavage and bust. How did you get that that 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 in half, folded it and placed it at the outer bottom side of my bra cup. It pushes your breasts inward and upward too”. We turned off the light and left for our first inspection.

This tidbit of info was picked up and stored by the room’s audio monitor. Miss Diane would add it to her notes later. ‘Recruit is creative, helpful AND experienced’.

I snapped out of my reverie and glanced at my ladies wrist watch. I snuck a quick glance toward one of the cameras. ‘Wow’ I thought. That was one of the longest days of my life. The memories were long ago but still vivid in my mind. I closed my well made up eyes and let my mind wander again while I waited.

Those mental images had Jenny laughing out loud! Oh boy, those were the rough “good old days” she thought. She stood, paced the room a bit and walked over to the full length mirror again. She looked fine. She made sure, for the cameras sake, to brush an imaginary hair behind her ear and to make a show of lifting her boobs back into place. She was actually proud of her C cup tits. She loved their weight and the way they jiggled when she walked. She also loved the pleasure that playing with her nipples and tits gave her.

Out of boredom Jenny walked over to the bed and laid down making a concerted effort to not mess her hair or dress. She kicked off her pumps and lay back to wait and to rest.

Back to the present

Day 16 continues

The Rules

In addition to the first days instructions The Rules were posted in every room and throughout the facility. They were also available on the in room TVs. If you transgressed you paid the consequences. Plain and simple. Consequences could be denial of food, clothing or added time to your indeterminate sentence and/or additional “goals” you would have to meet. Everyone knew. What everyone did not know is where they were being held and how long they’d be kept.

It was an exclusive program. Men only. Like the “judges” it was run by very bitter group of women that were dedicated to make men respect women and femininity. Their goal was to re-educate us and make women out of us; one way or another.

The video and audio Monitors

Every set of girls in training were assigned a staff member to monitor and report on the pair. The recruits would never know who their monitor was. By sheer luck, and good fortune, Jenny and Stacie were assigned to Miss Diane. The ‘girls’ were unaware whom their monitor was.

Miss Diane, in The Nest control room many rooms away, observed all this via the security cameras and microphones that were in all rooms. Miss Diane made an entry into Jenny’s progress report. ‘Jenny is a nurturer. She appears to better understand our program goals. She shows empathy and real concern for others. She is the most pragmatic and organized of the two roommates. She has excellent program potential.’

Opening Stacie’s file Miss Diane made note that ‘Stacie appears to be timid and scattered. May need some sedation added to her diet.’

The First inspection

Stacie and I were the first to arrive in the dayroom. We took a seat and glanced at our very feminine wrist watches. Nervously we massaged our hand bags. There was still about eight minutes before the deadline. Jackie and Rose were the next to arrive and were followed closely by Fannie and Joan. That made six of our ten. Beth and Tracie just made the cut. That made eight out of ten. 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”. The sound of the bolt locking was like the sound of a prison cell door being slammed shut.

Mary and Jewel began knocking on the day room door. There knocking increased in volume and desperation. “Miss Diane, please pull the door shade down.” The shade denied letting anyone one to see in or out. The knocking continued and the Matron used her walkie-talkie. “Security, code red. Please remove two sluts in training form 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 and then silence. Several of those that were on time were quivering with what had just happened.

“Now then, shall we start the inspection? Miss Diane, you take the backsides and I’ll take care of the front side. Bring your clip board. Jewel and Mary in room five are no longer with us. So we’ll start with room four. You ‘girls’ will comply with ALL of our requests or you’ll find yourself with Jewel and Mary on ward C.”

“ALL of you are to drop your panties down to your ankles. Is your lingerie and clothes color coordinated? Are your legs AND body parts cleanly shaven? Drop them now! Bend over and grab your ankles. Do it NOW!” Miss Diane started a slow walk behind the group. She ran her hands over every recruit’s legs. “Room four. Fannie. You have hair stubble on your left leg. That’s unsatisfactory. Your clothing is coordinated. Joan, your legs are smooth but your butt us hairy AND dirty. Do a better job or get your roommate to help. Room 3. Beth your posterior and legs look fine. I do not smell any moisturizer. Tracie you also have fine, smooth legs. A good pair of nylons will make them prefect. I’d suggest a Sun Tan color with a nude toe. Good job. Room two. Jackie. You obviously missed shaving your ass area but you appear fine otherwise. If you squat when you shave you can reach all the areas you need to reach. You may want to consider a depilatory crème. I personally find them messy and time consuming. Get hairless the best way you can. Ask your roommate to assist if you have to.”

“Room one. Stacie. Your backside looks extremely clean AND inviting. Did you have any help?” “Yes Miss Diane, Jenny was a big help. She got me hairless front and back, she grabbed my shaft and shaved the base! She also did my rear crevice. All I did was to ask for some help.”

“That’s what I like to hear; roommates helping each other. The only thing former recruits Jewel and Mary did were bitch and moan. Their efforts were divided and they failed. Jenny, your legs and arm pits are smooth; you’re clean front and rear. And you remembered the perfume. You also have another fine smell. Tell your girlfriends what that is.” “Miss Diane I used an after bath powder in my crotch area. It keeps me dry, prevents chaffing and smells pretty.”

Matron told everyone to stand up except Stacie. She was to remain bent over. “Recruits: you are all to walk behind Stacie and take a close look at her anal ‘rose bud’. Note how smooth and clean it is. She knows (or her girly buddy knows) how to properly douche. Look and learn. Notice that when I touch her ‘rose bud’ with my gloved finger how there’s a nice involuntary pucker reflex. If I poked a little deeper Stacie would easily grip my finger.” As Matron made a gentle probe Stacie gave a slight wiggle and took a gasp of air. Matron pushed again and went in about three inches. “Yes, there’s that gripping reflex I was mentioning. You will learn how to control this muscle for maximum pleasure for you and your lovers. You can learn to ’milk’ your partner by just flexing. Try it. Here’s a lubricated latex finger sleeve for each of you. Penetrate yourself.” Each recruit, put on the rubber sleeve and gave it a try and felt exactly what Matron was talking about. “Everyone stand upright and get back in line.” said Miss Diane. “Matron will now inspect your front.

Matron found very little to complain about: A lipstick smudge or two, an imperfect mascara application; trivial things. “Jenny, step forward and face your new sisters. Recruits take notice of how beautiful and attractive Jenny’s eye lashes are. She used multiple applications of mascara to thicken both her upper AND lower lashes. Without being told, she found and used an eye lash curler. She also found and used eyeliner. Her use of eyeliner makes her eyes standout. She did a fine job. You all will begin using a lash curler starting tomorrow. I hope you can appreciate the nice feel of your new nylon under garments. As you walk the friction and feeling of your panty hose is almost erotic. You have a lot to learn. 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.”

(to be continued -Chapter 2 "Day 16 - Breakfast" )

Indeterminate sentence - Jenny & Stacie- Chapter 2

Author: 

  • Donna T

Caution: 

  • CAUTION: Rape / Sexual Assault

Audience Rating: 

  • EXTREMELY EXPLICIT

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Illustrated

Character Age: 

  • College / Twenties

TG Themes: 

  • Crime / Punishment

TG Elements: 

  • Estrogen / Hormones

Permission: 

  • Posted by author(s)

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.”

diagram-of-anus-and-prostate-anal-cancer-4.jpg

“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)

Indeterminate sentence - Jenny & Stacie- Chapter 3

Author: 

  • Donna T

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • EXTREMELY EXPLICIT

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Erotica

Character Age: 

  • College / Twenties

TG Themes: 

  • Physically Forced

TG Elements: 

  • Panties / Girdles

Permission: 

  • Posted by author(s)

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.

Score1a.jpg

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.)

Indeterminate sentence - Jenny & Stacie- Chapter 4 (conclusion)

Author: 

  • Donna T

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • EXTREMELY EXPLICIT

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Erotica

Character Age: 

  • College / Twenties

TG Themes: 

  • Crime / Punishment

TG Elements: 

  • Sex Toys / Dildos

Other Keywords: 

  • male lesbians
  • male sorority

Permission: 

  • Posted by author(s)

(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.

Indeterminate Sentence Redux: Men Sentenced to Be Women

Author: 

  • Donna T

Caution: 

  • CAUTION: Sex / Sexual Scenes

Audience Rating: 

  • EXTREMELY EXPLICIT

Publication: 

  • 17,500 < Novella < 40,000 words

Genre: 

  • Illustrated

Character Age: 

  • College / Twenties

TG Themes: 

  • Gay Romance

TG Elements: 

  • Sissies

Other Keywords: 

  • becoming bi-sexual

Permission: 

  • Posted by author(s)

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.”

breasts

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.


Source URL:https://bigclosetr.us/topshelf/fiction/73909/indeterminate-sentence-jenny-stacie-chapter-1