This story contains scenes of an erotic nature, and is not intended for minors. Further if such material is considered illegal in your area, you should bypass this story. This story remains the property of the author. Permission is granted to download, photocopy, copy and re-post so long as any such action contains these disclaimers, and no attempt is made to profit from this story.

 

Sissy in the City            by: Charlotte             sissy_charlotte@sissify.com

 

Part One

I am a 29-year-old guy living in England. In most respects I have a normal life. I think readers might be interested in me because 10 years ago I spent three months in California on a work visa program. Lots of students have been on these programs over the years but I think I must have been the first one to spend the summer as a waitress and sex toy of a rich businessman.

When I arrived in California I already had a room booked at a cheap, run down hotel in the centre of LA. I didn’t have a job yet but I wasn’t worried because I had a lot of money with me. A few days after I arrived, I was on my way back to the hotel one night when I saw a sign for a transvestite club. I’d always been turned on by the idea of dressing in girl’s clothes, but never had the guts to do anything about it. Eventually I decided to go in and take a look around. The first thing I saw when I walked through the door was a group of gorgeous women dressed as waitresses. They were wearing very skimpy, black satin, French Maid’s uniforms with white piping. The uniforms had a short skirt and low cut top, and were worn with sheer stockings with seems running up the back, four inch spiked heels, layers and layers of white petticoats to push out their skirts, black elbow length gloves, a black choker, mop cap and a large, white, frilly apron tied with a big bow at the back. I must have stood there with my mouth open for 30 seconds. I realized they were guys, but I couldn’t get over how good they looked.

Eventually, I found my way to the bar, and after a few drinks, I started chatting with one of the waitresses. As I was obviously a foreigner on my own, she started asking me about myself. I figured that I was 8,000 miles away from home and unlikely to run into anyone who knew me so I was totally honest (plus I’d had a few drinks by now!) I told her how I’d always been turned on by the idea of dressing like her, but never had the courage to do anything about it. Sophie immediately called over her friends to hear my story. It turned out that most of the girls shared a house a few miles away and my fate was decided!

As soon as their shift was over, I was taken back to their house to play dress up. I had a few more drinks when we arrived for courage and soon found myself dressed in a corset, stockings, white blouse, black pencil skirt, low heels, make up and wig. I was amazed when I looked in the mirror, I always thought I’d look like a guy in a dress, but they had made me look just like a young career woman. I was thin, weedy, and short as a guy but I looked really hot as a girl. Dressed like that, I obviously needed a female name and they christened me Charlotte.

Pretty soon, I was spending as much time as I could at their house. I borrowed clothes from all the girls and was soon accepted as one of them. It took me a little while to get the voice right, but if I was careful, I could pass as a woman. After a few days, they even managed to persuade me to go out with them while dressed…once I realized nobody knew I was a guy I had a great time. A few nights later, I was at the club with them, wearing a beautiful green silk dress, with very high heels, when they introduced me to their supervisor. He was so impressed he offered me work covering for one of the waitresses who had twisted her ankle. At first I was scared by the idea - going out dressed in the evenings was one thing, but I wasn’t sure I could cope with wearing such a revealing uniform and being hit on by customers all the time. The girls soon talked me round, they pointed out that the dress I was wearing that night was pretty skimpy, plus I really needed to get some paid work. Eventually I agreed with the supervisor that I would try out the following night and see how I did. The girls were thrilled with the news and the next day took me out for a manicure and a haircut. My hair was quite long for a guy, but they got the hairdresser to give me a very cute bob. I wasn’t too worried at the time as I figured it meant I wouldn’t have to wear a wig while working. It was only later that I realized I would now have to stay as a girl all the time as there was no way I could comb my hair into a more masculine style. They also took me shopping and I got a few outfits of my own so I wouldn’t have to keep borrowing from them.

That night as I dressed in my sexy uniform for the first time, my heart was in my mouth. I really didn’t know what I was letting myself in for. I loved the way the uniform made me feel so feminine and vulnerable but I didn’t know how I would deal with the attention it would attract. The girls encouraged me by telling me I looked fantastic, but I made a lot of silly mistakes with my first few customers. There were a lot of hands on my ass as I took orders, but I learnt to brush them away. By the end of the night, I was exhausted (I wasn’t used to wearing stilettos for that long), but I had to admit I wanted to do it again. The supervisor agreed, and I signed up for the next ten days.

It was really strange going back to the hotel wearing a dress but nobody seemed to realize I was a guy. I soon got used to sleeping till noon and working at the club until the early hours, and as the end of the first week approached, I realized how much I would miss it. That’s when Ramon walked in (I’ve changed his name). Ramon was a tall, good-looking Arab who already knew most of the other girls. I couldn’t take my eyes off him and he spent most of the night chatting with me. It turned out he was a businessman. When I asked Caroline about him, she just laughed and told me he had been out with some of the girls and was a ‘bit kinky’. He was obviously interested in me though; when I went back over, he asked me if I would have a drink with him after my shift finished. I was thrilled, I rushed through the rest of my work and all the girls were giggling and teasing me about how I’d pulled big time. I’d come in that day in jeans and a sweatshirt, so I borrowed a little black cocktail dress from Suzie and went out for my drink with Ramon.

After about 5 minutes, I think I would have done anything he asked. I thought his stories were fascinating and I was totally captivated. We danced for a bit and then he leaned over and whispered that his car was outside and did I want to come back to his house? Needless to say it didn’t take much to persuade me. I got a real shock when I saw his car - it was a huge limo with a bodyguard in the front. We settled into the back and he showed me the bar. It seems really strange to say, but until that point, I had never had a homosexual thought in my life. After a few drinks however I found myself kissing another guy for the first time ever and pretty soon Ramon guided my head down onto his cock and I found myself giving my first blowjob. Thinking back, it felt like a natural step. With everything that had happened to me recently, I felt totally comfortable in my role as the girl doing everything possible to please her man. I even managed to swallow!

When we arrived at his house, I got my second shock of the night. It was a large mansion set in its own grounds with guards on the gate. We stumbled through the front door with Ramon’s hands all over me. He soon found the zip on my dress and by the time we got to his bedroom I was down to my corset, knickers, stockings and heels. I was having a really hard time with the buttons on his shirt, the girls had put false nails on me and I couldn’t grip anything. Soon he was naked and I got my first real look at Ramon’s cock. It was massive, much bigger than mine and it was rock hard. Then I felt Ramon gently bend me over, apply a sticky goo to my ass, and very gently enter me. At first, the pain was unbearable, and I thought he would split me in half. Then it began to ease and waves of pleasure overtook me. I could feel Ramon’s balls slapping against my ass as he rode me, and I tried to control my muscles to give him the tightest possible ride. His orgasm tipped me over the edge and we both came together, with him filling me up. Afterwards I was lying on the bed exhausted and Ramon got up to go to the bathroom. When he came back he was carrying something, but I was to weak to turn my head and see what it was. It was then that I got my third surprise of the night and found out why Caroline had called him kinky. Ramon lifted me onto his lap and began to spank me. I was too shocked to struggle, but after half a dozen really hard slaps I began to scream. He didn’t stop until I’d taken at least 20, by which time I was sobbing quietly. Ramon then lifted up the object he had just collected and fitted it around my waist. As he clicked the lock shut, I realized it was a chastity belt.

I was so shocked, I just looked at him with my mouth open for 10 seconds. Eventually Ramon laughed and reached over to stroke my hair. He told me I was his little sissy whore now and I would have to wear the chastity belt to make sure I only thought sweet, girlish thoughts and didn’t stray from my man. I was amazed, but more turned on than I’d ever been that this man had taken control of me in such an intimate way. Suddenly I winced as the belt did its work, Ramon just laughed again and told me I’d get used to it. If I pleased him, he would allow me short periods of relief. As I got dressed again I tugged at the leather band of the chastity belt but couldn’t shift it. Eventually Ramon got his driver to take me back to the hotel. As I sat in the back I wriggled around trying to get comfortable and coming to terms with the fact that Ramon now controlled my sexual pleasure.

When I woke up the next day I thought it was all a dream at first - until I felt the metal tube cut off my erection. The girls crowded round me when I walked in the club, demanding to know what had happened. Shyly I lifted my skirt to show them. Of course they all thought it was hilarious. Ramon showed up early that night and was very attentive. The chastity belt was really frustrating; I was desperate for relief, and probably would have done anything he asked. He added to my frustration by teasing me by waving the key in front of me. We went out again after my shift; he did take the chastity belt off for a short period like he promised, but only after I had spent half an hour on my knees giving him another blowjob.

The next night was my last night at the club and Ramon said he would let me go out with the girls afterwards, but he wanted to go to dinner with me the following night. I got back to my hotel really late and was woken by a knock on my door at 8:00AM. It was John (Ramon’s driver). He handed me two packages and told me I was to be ready for dinner at 7:00PM wearing exactly what was in the bags. After he had gone I had a look and found a beautiful white full-length evening dress with spaghetti straps, low front and a straight skirt with a split up one side, almost to the waist. I would have to be careful wearing that or everyone would see my chastity belt! There was also a corset, knickers, stockings and five inch spike heels. I spent most of the day getting ready for my date with Ramon, starting with a long luxurious bubble bath and another shave to make sure my body was totally free of hair. Eventually I squeezed into the corset and zipped the dress up. John knocked on my door again at 7:00PM sharp, and I stood up to go. Even though he had hardly acknowledged my existence before, he smiled broadly when he saw me and told me I ‘looked great’. I was feeling a little exposed, so I picked up a wrap. John immediately took it out of my hands telling me that Ramon’s instructions had been very specific. I was to wear only the clothes I had been given.

Needless to say there were lots of people staring at me as I walked out of the hotel. I even attracted a wolf whistle. John just smiled and steered me to the car. Ramon was already at the restaurant and stood up to greet me. I could feel his eyes all over me, and blushed deep red. Dinner was lovely, Ramon kept telling me how beautiful I looked. Towards the end he told me he had a surprise, but first he wanted to test my devotion. He told me to go to the Ladies, remove my knickers and hand them to him. I was so much under his spell by then, I just did as I was told without question. I felt a little thrill as I realized Ramon had demonstrated his complete mastery over me again.

When I sat down Ramon told me his surprise. As I was now unemployed, he wanted me to move in to his house. He would pay me pocket money and in return I would be at his side whenever he wanted. He told me that while we had been eating, his staff had packed all my things and settled the hotel bill. He gave no thought to the possibility that I might not agree - I was coming home with him that night. As we drove back to the house, I reflected that a few short weeks ago I had been just another guy. Now I was dressed as a beautiful woman being driven to the house of this man who had just taken ownership of me, as though my wishes did not matter. This really was my fantasy come true, I was so turned on by the fact, that I didn’t know where this was heading and had no control over events.

Ramon was obviously turned on as well; we had some of our best sex ever that night. We started in the kitchen and I think I was screwed in most rooms in the house. I must have kept the staff awake into the small hours with my screams of ecstasy.

Ramon spent most of his time away on business trips so I found I was left alone for three or four days and then with him constantly for 24 hours. He had sent someone out shopping to make sure I had a fully stocked wardrobe, although I noticed I didn’t have any trousers or shoes without heels. It was also clear there was no way Ramon’s staff would let me leave the compound; everything would be brought in for me. One day, about a week later, Caroline and Suzie came to visit me. Ramon had put me on a strict diet and they were amazed at how much weight I had lost. We were sitting around laughing and chatting when Ramon rang to tell me he would be home in a few hours.

While he was away I got to dress in more comfortable clothes but he liked me to dress as sexy as possible when he was around. This time he instructed me to go and remove the loose summer dress I had on and change into a white blouse, a very short and tight black leather miniskirt, sheer stockings and four inch strappy sandals. Of course the girls teased me and told me I was a good little wife doing what my husband told me. I didn’t care - the chastity belt was driving me wild with frustration by then. If this was what it took to please Ramon and get him to unlock me for a few hours then it was worth it. When he arrived, he pulled me to him and kissed me. He was delighted to see the girls there; he immediately started teasing me by patting his crotch and telling me how he had a big present for me. The girls thought all this was hilarious, especially when Ramon got me to serve all three of them during dinner later. As usual, on the nights when he got back from one of his trips, I received many loads of his precious cum in both ends of my body that night.

Perhaps the strangest thing that happened was a few weeks later, just before I was due to come back to the UK. As you may have realized by now, Ramon had a healthy interest in BDSM, and he belonged to a local Dominants club. Most of the members exercised varying degrees of control over their slaves, and one woman, with a house in the hills outside the city, had decided to marry her live in, feminized, sissy maid. Ramon had volunteered me as one of the bridesmaids. As I got into my dress on the day of the wedding, I had some of my worst jitters ever. I was wearing a full-length, cream silk dress with a tight bodice and straight skirt. My hair was a lot longer by now and Ramon arranged for a hairdresser to come in that morning. By the time he had finished, my hair was teased into a very elaborate arrangement and decorated with flowers.

When we got to the house, I found the other two bridesmaids and bride were already there. We were put away in a room on our own while the guests got drunk waiting for the ceremony to start. They told me all sorts of stories about the way their Masters treated them and I realized the humiliations Ramon put me through were mild by comparison. Jane (the bride) had even been made to serve dinner in a Victorian Maid’s uniform for two of her ex-girlfriends who her Mistress had tracked down. Throughout the meal, she had been forbidden from talking unless it was in French. One of the other girls had been made to walk into a bar and offer a blowjob to the first guy to join her outside. They asked me about Ramon, and told me they were very jealous my Master was so good looking. I was about to object and tell them Ramon was not my Master when I realized how silly that was. After all, Ramon had subjected me to, it was clear that he owned me body and soul. I had never disagreed or objected to a single order he had given me and I couldn’t see myself starting now. In a few short weeks, he had turned me into an obedient, feminine creature whose only goal was to make him happy.

It was a lovely sunny day, and the ceremony was out in the garden. The only problem with this was that our heels kept sinking into the lawn. Of course June had to promise to obey her Mistress and was made to kneel while a collar was locked around her neck. After the ceremony, a magician had been booked to entertain the guests. The bridesmaids had to serve drinks while Jane was made to change into a gold lame bikini and heels and act as the assistant to the magician. The poor girl was sawed in two, made to disappear, and shut into a box which the magician then stuck swords into. At the end of the final trick, Jane found herself in handcuffs, chained to a ring in the ground, without the top half of her bikini. She was just left there for 30 minutes while all the guests crowded around feeling her up.

After we had served dinner, Jane’s Mistress called the bridesmaids into a big bedroom at the top of the house. On the bed were three gold, white, and red cotton cheerleaders dresses which we were ordered to change into. We then put on track shoes and braided each other’s hair into pigtails. Mistress produced some leg irons and chained the three of us together. She then locked collars around our necks. Each of the collars was attached to the others with a short length of chain. Once we were securely fastened Mistress led us back downstairs as we shuffled behind her. She stopped outside one of the dining rooms and knocked. When we entered we saw our owners sitting around a large table covered with a white tablecloth playing cards. We were ordered to get under the table and give our owners a blowjob.

We must have been under there for hours! The women all thought this was hilarious and clapped every time we managed to bring one of them to orgasm.

Shortly afterwards, it was time for me to go home. Ramon never suggested we had a long-term future together, he always told me he would let me go when the time came. Even so, he was determined to keep me under control for as long as possible. I was allowed to get a hair cut and dress in T-shirt, jeans, trainers, and jacket for the journey to the airport but he made me wear a corset, knickers and suspenders underneath and would not release me from my chastity belt. He also made sure all my clothes were packed in the suitcase so I would not be able to change during the flight. When the time came to say goodbye, he kissed me on the lips in front of all the other passengers and handed me a key. Then he walked off.

I ended up undressing in the toilet on the aircraft and leaving my lingerie in the rubbish bin. Luckily the key he gave me was for the chastity belt so I was finally able to remove that too. I’ve often wondered what the cleaners must have thought when they found all that sexy underwear and a chastity belt when they were cleaning the plane!

 

I hope everyone enjoyed the story; it is my first effort.

I welcome any comments or suggestions.

 

 

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© 2001 by Charlotte. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.