Serving Sissy Waitress

A True Sissification Story

This is the story of how I ended up being a serving sissy waitress- serving others. At the beginning of the night, I had no idea it would end like this!

My wife, Susan, one evening announced to me that we had been invited to a party at a new friend of hers. Victoria had inherited a fortune from her father and she lived in a mansion in the best part of town. It all sounded very exciting. Apparently she had these parties once a month. Susan said that we would go earlier as she had offered Victoria that she’d help her with any last minute arrangements.

The evening arrived and, dressed in our finest evening clothes, we left the house and traveled to Victoria’s by cab. I was rather boringly dressed in my usual tuxedo. But Susan looked fantastic. She had gone to a lot of trouble getting done up for the party and had spent two hours at a beauty salon that afternoon.

She was wearing a long red dress with a plunging neckline and a slit up one side that came all the way to the top of her thigh. I walked behind her to the car and the absence of any panty-line on her sexy bottom indicated that she either wasn’t wearing any panties or she had the skimpiest g-string on.

As I helped her into the rear seat of the car, her dress parted at the slit and I caught a glimpse of stocking tops and suspender straps. Mmmmm, I think I’m going to get lucky tonight. I almost couldn’t wait for the party to be over so that I could get her in my arms and get her dress off.

Idea for Serving Sissy Waitress Planted

We arrived at Victoria’s house and it was really impressive. Victoria met us at the door and, wow, she was even more impressive. A tall athletic woman with red hair and a striking electric blue evening dress. “Hi Hon”, she greeted Susan, “and you must be David?” She leant forward and kissed me on the cheek. She was clearly used to being a dominant woman in control.

“Make yourself comfortable in the lounge while Susan and I get the last minute preparations done. My dear, I’ve got problems. Some of the waiters haven’t arrived”, she said to Susan, as they disappeared towards what I assumed was the kitchen. Before I could settle down in a couch in the lounge, Susan was back. “Dave, Victoria has got a real problem. She’s short of waiters and waitresses. Could you please please help her out?

I promise I’ll make it up to you later tonight if you be a real honey and act as a waiter tonight.” This wasn’t what I had in mind at all. Totally out of character, I agreed before I even had a moment to think about it. Somehow I had a desire to please Victoria. Strange feeling! “Oh you’re real darling”, Susan exclaimed, and she hugged my tightly and gave me a peck on the lips.

“Victoria is waiting for you in the kitchen. She’ll sort out what you wear.” I walked through to the kitchen, which was a hive of activity with waiters milling around in their tuxes. Victoria grabbed me by the arm and led me out of the kitchen and up the stairs. “You’re a real hon”, she said. “Lets get you sorted out quickly before the other guests arrive.

Unsuspecting Male Turned into a Sissy Waitress

She led me into a huge bedroom and through into what was clearly her dressing room. “I don’t actually need waiters, there are plenty of them. What I’m missing are waitresses. Susan said she was sure you wouldn’t mind dressing as a sissy waitress for the evening.” What! I’m not a girl, I’m not dressing as a waitress!” I exclaimed. “Yes you are darling. Don’t worry, you’ll look wonderful and gorgeous.” She didn’t even wait for my reply. There was that control-thing of hers again.

“My beautician and her assistant is still here and they’ll have you ready in no time.” And with that she breezed out of the room and left me with her beauticians. Then things moved fast. I had no control over it. My clothes were whipped off, lotions applied to my body, rushed under a shower, and before my mind had time to register I was sitting in a chair, completely naked and exposed, with not a hair on my body from my neck down. One beautician was working on my face, plucking eyebrows and doing my make-up, while the other was painting my toe and fingernails.

She was applying long false nails and these where being painted bright red to match my painted toenails and the lipstick that was now being expertly put on my lips. Then I felt my ear being pierced and long dangly earrings put in. To complement the earrings, a pearl necklace and matching bracelet was added. They were not messing about! This was being done properly and professionally. Then they produced a long red curly wig and once that was in place and styled, the clothes were brought out. I was dressed and within what felt like minutes, but actually was an hour, they led me to a long floor length mirror.

Sissy Maid Server Transformation Complete

That was when the true sissy maid sissy waitress was born. There I stood, fully made up feminine face, six-inch high black stilettos, stockings, French maids dress and underneath the dress I had on a lacy black corset with suspender straps and the tiniest lacy g-string. The short ruffled white petticoat under my dress barely covered my bum and you could see the suspender straps and stocking tops. Oh my god, I was a very sexy French maid waitress!!!!!!!

I could hardly walk in the high heels. They forced my back to arch and my bum to wiggle seductively. “Oh, you look wonderful”, exclaimed Victoria, who had suddenly reappeared. “You are going to be quite a catch, you sexy little girl”, she laughed. I again looked at myself in the mirror and actually felt a stirring in my cock. I was turning myself on!

Victoria escorted me down to the kitchen, which was now very busy and active. “Hi guys. Meet Dee. She’s a new sissy waitress who will be helping out tonight. Dee’s not a pro like the rest of you, so please be kind to her and show her the ropes.” With that she chuckled and patted me on my bum under the ruffled petticoat. I suddenly realized that I’d accepted my introduction as “Dee” without a moment’s hesitation. That was my new name and it seemed to fit and sit comfortably in my head.

Victoria left and I was caught up in the blur of waitressing. I carried drinks on a tray, rushed back to the kitchen to refill it and then back out to the guests. I had no time to think or stop to reflect on my situation. It was too busy and I had to really concentrate in carrying the drinks tray without spilling drinks or dropping it. The guests were spread all over the house.

There were several formal lounge rooms and some guests where in the TV room and other lounge rooms upstairs. Fortunately I didn’t have to serve upstairs. With my very short sissy waitress dress, I would have been totally exposed from underneath if I had to walk up the stairs.

I caught a few fleeting glimpses of Susan (remember my wife?) as I was serving. She seemed to be having a great time and always had a bevy of guys around her. She was totally unperturbed about me and didn’t even acknowledge that I was there. I noticed that some guy invariably had his arm around her waist as they talked. And often a hand was on her sexy bottom, loving stroking it. She undoubtedly was enjoying the attention.

Newly Transformed Sissy Waitress Has a Fabulous Time!

But I had no time to reflect on Susan’s activities. I was far too busy being a sissy waitress serving drinks. My mind had totally shifted to my current role and duties. I was Dee the French serving-maid. My walk was sexy, with bum and hips moving sexily on the high heels. I loved the feel of my stockinged-legs brushing against each other.

And the admiring glances, comments and frequent hand-caresses on my sexy little bum was accepted and, yes, in fact welcomed. I was vaguely aware of the fact that I was intentionally mincing around as sexily as possible and even flirting with the male guests and waiters. I was truly a sissy waitress and hadn’t even realized it yet!

After about 2-hours of frenetic activity, things started calming down. The guests were not requiring new drinks as frequently and I had more time to enjoy the atmosphere and stop for brief flirtatious chats with the guests. Guys were putting their arms around my waist as I stopped to chat with the drinks tray in my hands. Oh how I was loving being a sissy waitress!

Sissy Server Turned Sissy Slut

With their arms around my waist, their hands would drop down under my ruffled petticoat-dress and gently rub my sexy ass, caressing my bum-cheeks and tracing the thin g-string cloth down my bum crack. I was loving it! I felt sexy, erotic and horny and my mind turned to thoughts of sex, cocks and copulation.

As my Dee-mindset took over, I became braver and I would find myself pushing my leg against a warm groin while the recipient of my attentions was taking his drink from the tray. In every one of these instances, the guy reciprocated by pushing back against my leg. The feeling of a hard cock against my thigh was a wonderful feeling. It gave me a taste of my sexual power over these horny guys.

As I went back into the kitchen to replenish my drinks tray, the head waiter announced, “OK guys, time for a change of pace. Get your clothes off and strip down to your undies.” The waiters immediately shed their tuxedos and were down to sexy little black silk g-strings within seconds. The small silk pouches showcased their well- endowed cocks beautifully.

It was such a horny sight that I couldn’t stop myself from putting my hand on the nearest pouch and giving his cock and nice feel and squeeze. The waiter clearly loved it because it immediately grew hard and was barely kept covered by the g-string. I stripped my dress off and their I stood in my black lace corset, g-string, stockings and high-heeled stilettos.

I felt hands on my bum and then a male g-string glad cock was pushed hard against my ass. The owner gave his cock a nice hard rub between my bum cheeks as his hands grabbed my tits from behind. He pinched and tweaked my nipples till they were hard, which was within seconds. Mmmmm…..that felt so good. If I had a vagina, it would now have been wet.

Sissy Sluts Serving Real Men

We were then sent back out to mingle with the guests, but with no need to carry our drinks trays anymore. Our purpose and role had clearly changed from sissy waitress(es) to sissy slut(s).

The waiters and other waitresses dispersed around the guests and all of us were in hot demand. Female guests were chatting to the waiters with the arms around their waists and their hands were openly and blatantly running over the firm male buttocks and cocks. The female waitresses were getting the same attention from the male guests.

In fact, now that I’m looking more carefully, there wasn’t a strict gender divide at all. Male guests were enjoying the male waiters and several female guests were caressing the waitresses. This was a group of people who were very comfortable with playing, touching, caressing and enjoying either sex.

Sissy Slut Enjoys Attention from Both Sexes

I was having a wonderful time being a sissy waitress and sissy slut. It was quiet scary how much I was enjoying the attention of the small group of guests that I’d joined. There were three guys and a beautiful woman. My clitty-cock was clearly visible through the scanty lace of my g-string and she was lovingly stroking it through the lace. I could feel two pairs of hands stroking my bum and I in turn was rubbing a nice firm cock through a pair of trousers. It was rock hard and I could even feel that it was a nice circumcised cock.

One guy’s hands disappeared down the front of my panties as I transferred my hand to the girl’s breasts. She had wonderful tits and I slipped my hand inside her low cut dress and felt her hard nipple. She sighed as I played with her tits and nipples. One of her companions undid the zip at the back of her dress and her dress dropped to the floor. She was naked to the waist and looked stunning and sexy in dark red suspenders, matching g-string and sheer black stockings.

All three guys attentions turned to us two girls and we were being caressed all over our bodies. The one guy, Ben, leant towards me and kissed me hard, his tongue forcibly pushing into my mouth. I reciprocated and we kissed passionately with our tongues entwined. I felt hands on my g-string and the next moment they were ripped off my body. My clitty-cock jumped into the open, hard and exposed.

Sissy Slut Humiliation

“My my, but you certainly are enjoying yourself aren’t you”, a voice laughed next to me. It was Susan. For a moment I was mortified, but then I saw that she had two guys on either side of her and she had a hard cock in each hand and judging by the pre-cum on each cockhead, she had been giving these cocks a good solid workout. Without thinking, I leant forward and licked the pre-cum from the one cock.

Susan released her hand from her partner’s cock, put it behind my head and shoved my head down on the cock, shoving it deep into my mouth and down my throat. “Didn’t take you long to be transformed into a cock-sucking slut, has it my dear”, Susan laughed. “Well darling, enjoy yourself. I think we may have found a new career for you. I can see that I will make a lot of money by selling your body.” I couldn’t care less. All I could think of was the hot cock in my mouth and how I was now a cock sucker. I was on my knees sucking it for all I was worth.

Hands pulled me back onto my feet, and with my hands hanging onto the guy’s waist, my mouth clamped tightly to his cock, my naked ass was clearly exposed for all to see and use. I felt first one, then more fingers probing my cunt from behind. I was being finger fucked from behind. My clitty-cock grew hard. I then felt something bigger push against my cunt opening. “Oh my god, that’s definitely a cockhead”, I said to myself in my thoughts.

Then I heard Victoria’s voice. “Wait guys, Dee’s a virgin….the only virgin here tonight….and I’m planning a virgin-deflowering ceremony later, so don’t get yourselves carried away yet. Use your fingers and let her suck cock till she has nothing left in her mind except cocks. But keep your cocks out of her pussy for now. You’ll all get your turn later tonight.” I couldn’t care less what she had planned.

Sissy Slut a Virgin No Longer!

All I could think about were all the cocks now presenting themselves to my mouth. I was back on my knees and servicing one cock after another, sometimes two or three at a time. I couldn’t see or care about anyone’s face. All I was focused on was hard cocks of all shapes and sizes. And then the first cock exploded in my mouth. I sucked and swallowed the cum.

My first ever taste of cum. I swallowed every last drop and then the next cock was shoved into my mouth and after fucking my soft mouth as hard as possible, another load of cum exploded into my mouth. This was repeated several more times by several more cocks. My mind was filled with “cock, suck, cum, swallow, suck, suck, fuck, cock, cum, cock, suck, suck”. Nothing else was in my head!!!!

Eventually I fell back, exhausted and with my mouth sore and covered in cum. Victoria reappeared and said, “Come my darling, let’s go and get you cleaned up and get your makeup sorted out.” Obediently I let her lead me from the room and up to her dressing room. There she sat me down and fixed my makeup and reapplied bright red lipstick to my lips. She instructed me to play with her pussy while she worked on my face and dutifully I played with her clitty and moved my fingers in and out of her pussy.

She was wet and had a sexy musky smell. Slowly thoughts of cocks partially left my mind and it settled down to bi-sexual thoughts. “You were quite a little performer in there my dear”, she said with a giggle. “Susan and I just knew that you were a little girly slut at heart. She’s told me that she wanted to turn you into a sissy-slut for years and so we hatched this little plan together. And you haven’t disappointed us at all.

New Sissy Assignment

From now on we are going to use you often for my and other parties and you will live the rest of your life as our sissy plaything, to use and rent out as we please- from sissy waitress to sissy slut. We’ll get you on hormone treatment so that you can grow some nice titties.” To my (very brief) horror, I found myself nodding obediently in assent. This is exactly what I wanted. I wanted to be a submissive sissy-slut that was used for serving and sex. But I had no time to reflect on this news or my new state of mind. Victoria was impatient in getting me ready for whatever she had planned as a next step for me.

She re-applied lipstick to my lips and tidied up my make-up. “You seem to have lost your panties darling”, she said as she produced a new lacy g-string. “Slip these on and then we’ll go and rejoin the merry group downstairs.” Obediently I put the panties and then followed Victoria back downstairs.

There was plenty of activity and fucking going on in the living room. Groups of two’s, threes and more were engaged in all variations of sex acts. Guys were sucking each other’s cocks, girls were licking pussies, guys were fucking girls (and each other) from both ends. It was a very erotic and horny scene.

In the middle of the room stood a large leather covered ottoman. Victoria lead me straight to the ottoman and announced, “Gather round everyone. We have a virgin whore, which is a most unusual specimen to have at our disposal, who is just dying to perform for our pleasure.” Everyone laughed and moved to seating around the central ottoman. Susan, I noticed, was already seated on a couch facing the ottoman.

She was naked except for her suspenders, stockings and high heels and was seated on a guy’s lap with her back to him and her tits and pussy facing forward. His huge cock was in her pussy and she was riding him with long up and down movements. On the up stroke, his cock would almost be out of her cunt….you could see the cockhead appearing…and then she would impale herself to the hilt as she lowered her body back down. She had a dreamy sexy look on her face. He was playing with her nipples from behind. I felt jealous of his big cock, double the size of mine, and also jealous of Susan…I wanted that big cock in me.

“On to the ottoman with you, sissy slut whore”, Victoria commanded. “Get onto your hands and knees.” I did as I was told. My ass was open and vulnerable for all to see. “Now start sucking some cock while I auction your virgin cunt off to the highest bidder.” Immediately a large cock presented itself to my mouth. I started sucking while Victoria started an auction process. She was going to make money out of me.

Sissy Waitress/Sissy Slut Auction

I was so busy sucking one cock after another that I couldn’t keep my mind on the auction process. My mouth and mind was filled with cocks. Finally the auction was finished. My virgin cunt had been sold to a syndicate of three guys. For $10,000 they were going to have the pleasure of being the first three guys into my cunt.

“Victoria, we want her tied down. We don’t want her breaking free while we fuck her”, the leader of the gang said. Victoria response was, “That’s fair. Get some of those silk ropes and we’ll tie her down nice and firmly.” The ropes were produced, and whilst kneeling on the ottoman, my legs were pulled wide apart and secured to hooks on the side of the ottoman. I couldn’t move my knees in any direction.

Not forward, back or move them closer together. Then they tied a rope to each wrist and pulled me forward. My body rested on my elbows and the ropes where tied to hooks at the front of the ottoman I was firmly tied, unable to move other than by slightly moving my bum forward and backwards. My ass was totally exposed and prominently displayed for all to see. For the second time that evening, my panties were ripped off my body.

“John”, Victoria said to the ‘rape’ syndicate leader, “you get Dee to get you nice and hard and wet and ready for her pussy, while I lube her up for you.” John presented his cock to my mouth and forced it between my lips. I immediately started sucking his cock. There was no thought process in my head. I just wanted that cock to suck and lick.

I could feel cold lubricant being placed at my pussy opening and then it was being worked in with a finger. Must be Victoria. Everyone cheered and laughed. I looked sideways towards Susan was sitting. She was laughing louder than anyone else and she was now riding her cock with force. I’d never seen her so turned-on. The stranger’s cock in her cunt and the sight of me being prepared for a raping was clearly very exciting to her.

“She’s all yours John”, Victoria announced. John pulled his cock from my mouth, moved behind me and then I felt a hard, and yet soft, knob against my pussy opening. He grabbed my by the hips and pulled me back towards him as he pushed forward. I could feel his cock head starting to push into me. I screamed with pain. He was not being gentle at all. He kept forcing his cock deeper into my tight pussy.

The pain kept building. Then I felt his balls touching my ass. He was in right up to the hilt. He pulled back, and the pain subsided slightly, and then he rammed his cock back into me. I screamed again, and I kept up the screaming as he pounded my pussy, fucking me hard and roughly. I have no idea how long this continued. Eventually, what felt like an eternity, I heard him groan and then I felt warm liquid squirting inside my pussy.

He was cumming. He kept fucking me for a few more minutes, until every drop of his cum was pumped into me. He withdrew, and immediately I felt the next cockhead at my pussy entrance. Again I was fucked hard as the next guy shoved himself into me. Again I screamed with pain as he fucked me.

And then, suddenly, I became aware that I was no longer screaming. I was moaning with pleasure. The pain in my pussy had been replaced by the most incredible sensation of wanton pleasure. I was even pushing my bum back with each forward stroke of his cock. I was fucking just as hard as he was. I had become a fuck-slut. My own clitty was now hard and standing at attention underneath me.

This change in my behaviour from reluctant sissy waitress and sissy slut to eager and willing sissy slut, had not gone unnoticed. “Look at our little sissy-slut. She’s loving it. She wants to be fucked. Look Susan, look at our cock-loving slut”, Victoria laughed. And she was right. I was loving it. I didn’t want him to stop fucking me and I wanted it hard and rough.

He groaned, shot his cum into my pussy, withdrew and then the next cock pushed into me and started fucking me. “Oh yes, yes, yes…fucking me”, I moaned. One cock after another shot their cum into me. Cum was dripping down the inside of my thighs.

I was wet, juicy, hot and ready for these cocks. Wave after wave of femme orgasms rippled through my body. I wanted every single guy to fuck me and for it to never end. Eventually, after what must have been at least two hours, there were no hard cocks left in the room. People were lying sprawled on couches, chairs, day beds and the floor, spent and relishing in the afterglow of good hard fucking. I could see cum dripping out of pussies and assholes.

I still wanted more of being a sissy waitress/sissy slut. I had been transformed into a single-minded cock-loving sissy fuck-slut and I was loving every minute of it!

By Sissy Dee

Did this story get you all excited to be turned into a Sissy Slut? Give one of our Sissy School Mistresses a call, today to begin your sissy slut training!