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

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

Previously: John reflects

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

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

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

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

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

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

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

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

Start of my work week - My face still looked kissable

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

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

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

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

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

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

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

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

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

Britney Arrives at Work

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

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

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

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

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

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

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

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

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

Lunch

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

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

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

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

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

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

To Pretty John in bookkeeping

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

I smiled broadly. “Oh, really?”

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

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

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

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

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

Last Break

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

Called to Human Resources: Diversity and Inclusion

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

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

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

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

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

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

Alone with Human Resources

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

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

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

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

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

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

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

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

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

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

Going on the Offensive

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

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

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

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

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

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

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

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

Bull’s eye!

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

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

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

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

Matt takes the bait!

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

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

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

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

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

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

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

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

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

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

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

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

Console and Control: Will it Work?

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

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

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

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

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

I began to negotiate

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

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

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

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

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

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

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

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

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

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

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

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

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

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

A Bold Move

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

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

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

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

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

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

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

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

“The best is yet to cum” I told him

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

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

Taking Further Control

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

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

“Why do you want to wear lipstick Precious?”

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

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

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

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

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

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

Who’s the Boss?

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

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

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

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

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

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

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

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

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

I left for home

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

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

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

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

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

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

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

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

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

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

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

Family Negotiations

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

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

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

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

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

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

General Agreements Overview

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

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

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

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

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

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

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