My name is Sean and I have been a sissy crossdresser all my life. I have always kept it a secret, dressing up like a girl alone in my little apartment. I only ventured outside "en femme" occassionally and only if I was pretty certain I wouldn't run into other people.
Night after night, I would come home to my apartment and transform myself into the lady of my dreams. I had become very talented with my make-up, my mannerisms and my voice. I knew that I looked very attractive and convincing when dressed. Alone in my apartment at night, I would read romance novels and fashion magazines and watch chick-flicks on TV. But the more time I spent pretending to be a girl, the stronger my fantasies became to actually experience life as a girl. I became obsessed with the idea of being desired and romanced by a real man -- just like in my novels and in the movies.
About six weeks ago, when my obsession became too much for me to control, I went into action. I created a profile of my femme self on Match.com. It took me several hours to get it just right. First, I picked out a few of my best girlie photos, including these two below. I like the one on the left because it shows off my legs. And I like the one of the right because it makes me look more sophisticated and mysterious.
And finally, just to make sure I got everyone's attention, a photo of me in a bikini!
I came up with a back-story that sounded believable and would be appealing to men browsing through the website. I was, according to my profile, Sheila Landers, a 26 year-old junior high school teacher who had recently moved to the area. I said I was looking for a "successful, older gentleman who was interested in a long-term relationship." I described my interests in all sorts of girly things, like ballet and cooking. I described in detail my idea of a perfect first date -- a candlelit dinner at a French restaurant followed perhaps by a romantic walk...I got myself excited just thinking about it!
What my profile didn't include was anything that was actually true. It didn't say that I was a 20 year-old sissy and college drop out who worked for minimum wage in a corporate mail room. It didn't say how the idea of being romanced by a man excited me and terrified me -- all at the same time!
When I was finally satisfied with my profile, I pressed Enter and posted it on Match. I didn't really know if anyone would write back to me or even notice my profile.
I needn't have worried about that. About two hours after I uploaded my profile, I had about twenty requests from men wanting to meet me. Within a week, I had over two hundred offers for dates!
After my parents died in a car accident, I was sent to live with my Uncle Jim. I had never really liked Uncle Jim. I had always thought that he was sort of rough and maybe a little strange. I was about to discover how right I was.
Uncle Jim lived alone in a big, old farmhouse far out in the country. His wife, Darla, had walked out on him many years ago.
No sooner had I brought my suitcase into the house the Uncle Jim announced, "You won't be needing your old clothes. I got plenty of better clothes for you to wear. You see, when Darla ran out on me, she left all her old things. And so now you can take Darla's place. So why don't you go upstairs and put on one of Darla's pretty dresses while I go out back and burn your old clothes."
I began to protest but Uncle Jim started beating me. Hard. I was no match for him; I was small and weak and he was huge and strong. It didn't take long for him to wrestle my suitcase away from me and to drag me up the stairs to Darla's old closet. He picked out a dress and threw it on the bed. "Now get changed like I told you to!" he shouted. "There's underwear and make-up in those drawers and there are pretty shoes in the closet. Now hurry up, get dressed and get your ass downstairs." He hit me again before he slammed the door behind him and stomped down the stairs.
I was paralyzed. I started crying as I sat on the bed, looking at the flowery dress that was lying there. Then I smelled smoke. I looked out the window and true to his threat, Uncle Jim was burning my clothes in the back yard. I knew I was in big trouble and that I had better start cooperating or something really bad would happen to me. I put on one of Darla's bras, a pair of her panties, the dress and some shoes. I put on some red, red lipstick and some rouge on my cheeks. I took a deep breath and headed down the stairs to where Uncle Jim would be waiting.
That was nearly a year ago. I have been living and dressing as Darla all day, everyday, since I arrived. My hair has grown longer and I am now better at doing my make-up and walking in high heels. Uncle Jim calls me Darla and expects me to do everything a good housewife does. I cook and serve three meals a day for him. I scrub the floors and wash the windows. I vacuum and I dust. I do Uncle Jim's laundry. My chores are endless. I hate my life. As I do my chores, hour after hour, day after day, all I can think about is how wonderful and free my life used to be, when I was a normal boy. But that life is behind me now. I am the Sissy housewife/slave of a demented monster.
Uncle Jim gets very mad at me if he catches me daydreaming or not doing my chores vigorously enough. And he gets furious if he thinks I don't look pretty enough or if I don't sound and walk and laugh enough like Darla did. And when I disappoint him he throws me over his knee and spanks me brutally.
And after I have cleaned the the house from top to bottom and after I have put away the dinner dishes, I have to put on one of Darla's nightgowns and take care of my "husband's" sexual needs. No matter how awful my household chores are, nothing is as awful as having Uncle Jim's giant naked body on top of me, kissing me and feeling me up all over. But worst of all is when I have to do the things that he says Darla refused to do. I have to put Uncle Jim's cock in my mouth until he gets ready to cum. Sometimes he likes to cum in my mouth and make me swallow it. But mostly, he likes to pull It out just before he cums and shoots it all over my face. After I clean us both up, Uncle Jim usually climbs on top of me again and falls asleep. That's when I usually start crying until I fall asleep, getting a little rest until my life as a sissy housewife/slave starts again in the morning.
Unless a client specifically requests that his new sissy be delivered as a virgin, I always arrange for my sissy creations to have one final important "lesson" before I consider my transformation work to be complete.
My sissies have to submit to a "lesson" in sissy lovemaking given by my good friend, Mr. Rhino. Mr. Rhino is an enormous and strong black man with the biggest cock I've ever seen. Seriously, it's like a baseball bat!
The sissies know what is expected of them, even though they are scared half to death. They are to submissively lie on their backs and allow -- no, invite -- Mr. Rhino to fuck their tight little sissy pussies. And despite the agonizing pain they experience, they are expected to pant and moan like the little sissy whores their new Masters will want them to be.
Here Mr. Rhino is giving Sissy Sally his final lesson. Poor Sissy Sally was close to tears as he lay on the bed watching Mr. Rhino undress, exposing his monster dick.
But here's the best part. When I have other sissies-in-training in my house, I make the more junior sissies sit on chairs next to the bed, watching their more senior sissy sister get his fucking lesson. It's great fun to watch the junior sissies as they sit and watch in horror. Some burst into tears watching the fucking show as they all know that within a few short months, they will be receiving the same special lesson from Mr. Rhino and that giant black battering ram he has between his legs.
Janey had a little headache when he woke up the next morning. But we weren't going to let a little hangover spoil out last "mother-daughter" day in the city. Janey wore a pretty black and white sleeveless dress, which was perfect because the day was warm. Our plan was to have breakfast and then head to church -- going to church gives Janey the perfect excuse to get all dressed up on a Sunday morning. Then some more shopping, a light lunch and then back to the hotel for Janey to put his dresses away before heading home.
But just as we were leaving the hotel to walk over to the cathedral we ran into Janey's young banker friend from last night.
"Janey!" he exclaimed when he spotted us. He gave Janey a quick kiss on the cheek. "I'm so glad I saw you. I was going to call you later, but now I can ask in person." The young banker looked my son up and down, his gaze lingering on Janey's sexy legs. "Wow! You look...amazing," he panted.
The young banker seemed to have lost his train of thought staring at Janey -- and Janey was so mesmerized by his romantic young banker that he had no idea what was going on. I helped everyone out. "Was there something you wanted to ask Janey?" I prodded.
"Oh, yes, right," he managed to stammer as he collected his thoughts. "I have these tickets to a big charity fund-raiser on Friday night at the Downtown Yatch Club. It's one of the big social events of the year. It is going to very nice party and I was wondering if, well, if you would be my date for the evening."
Immediately, and without consulting me, Janey replied, "Oh yes! I would love to go!" And with that Janey gave his new boyfriend a big hug.
I, of course, was terrified. Janey was quickly getting into very deep waters here and I was not at all certain that he would be able to pull this off.
Thinkly quickly, I explained to both of them that Janey and I would again get a hotel room for Friday night and that Janey could go to the party provided that "she" was back to the hotel by 1:00AM. The banker gave Janey some more details and promised to be in touch soon. We said our good-byes -- including a big, long kiss for Janey -- and Janey and I continued on with our ladies day out.
The days that followed that magical weekend were very difficult for Janey. Not only did he have to change back into his boy clothes for the week, but poor Janey was experiencing his first schoolgirl crush. The emotions were so powerful. He was simultaneously mopey and sad because he missed his young banker boyfriend and wildly excited about seeing him again at a fancy, very adult, cocktail party on Friday.
The school days passed very slowly for Janey that week. When Friday did finally come, I let him miss school so that I could take him back in to the city to shop for a new dress to wear to the party. We checked back into our hotel and hit the designer boutiques. And we found the perfect dress! It was a black, sleeveless dress with little white polka dots. It was a faux wrap style that had a bow on one side and was cut tantalizingly low in front. The full skirt came right to his knee, a layer of chiffon gave the whole dress a romantic, elegant effect. Janey looked stunning in his new cocktail dress.
We spent most of the afternoon getting him ready. I took Janey to a salon near the hotel to get a mani-pedi (I knew he wanted to wear his favorite open toed shoes with the ankle strap) and to get his make-up done.
Janey's banker met us in the hotel lobby. I thought the young man was going to die from excitement when he saw how pretty Janey looked. The banker had arranged a limo to take them to the party. I said goodnight to the young couple and whispered to Janey to be careful. As the limo pulled away from the curve, I gave a little wave as I watched Janey head off for his first date as a young lady.
Of course I stayed up waiting for Janey to come back to the hotel that night. When he did get home, he was wide awake and bubbling over with excitement. Janey had to tell me about every detail of his dreamy, romantic evening: the music, the celebrities he saw, the food, the drinks, the pretty dresses the "other" ladies wore -- everything. He even had to describe the fancy ladies rest room at the yatch club. But mostly he wanted to describe how charming and romantic his date was. How they danced together and how they made out on the balcony overlooking the harbor.
Then Janey said, "He wants to take me out on another date -- alone -- tomorrow night."
I knew that this charade must not continue. Someone was going to get very hurt when the truth came out -- probably Janey. "No Janey, that is not a good idea. I can't allow you to do that. This is all getting very...complicated. Just what do you think is going to happen when he finds out you aren't really a girl?"
"I already told him and he doesn't care!" Janey replied. My mouth dropped open and I almost fell over with surprise. "It's true," Janey continued. "I told him that am a Sissy during the limo ride after the party. At first he didn't believe me until pulled down my panties and showed him."
"WHAT?!?" I exclaimed. "What did he do then?"
"He said that if I wanted to be his Sissy that I needed to suck his cock. So I did. Right there in the limo. And after he came in my mouth he told me that I suck cock better than any real girl that he's been with. And that he wants me to be his Sissy! Isn't that wonderful, Mother? I am so happy! I am in love with him, Mother."
Before I fainted, the last thought that passed through my mind was that my sweet little Sissy daughter was now a complete Sissy slut!
Janey finished doing his hair and his make-up. He slipped on the dress I had bought him earlier that afternoon. He looked simply stunning. I was so proud of my beautiful sissy son.
We rode the elevator down to the restaurant. As we crossed the busy hotel lobby, I was aware that everyone was noticing this striking, elegant and -- dare I say it -- sexy young lady as he walked past. I'm sure Janey noticed that many heads were turning because of him.
Unfortunately, the restaurant was very busy and we hadn't made a reservation. The Maitre d' suggested that we have a drink at the bar and "perhaps a table might become available." We did as he suggested and stepped into the hotel's lounge. The bar was mostly full of men -- and it was very crowded. When we couldn't easily find a seat, I started thinking about leaving. But just then, two men slid off their bar stools and offered their seats to us.
The men introduced themselves as investment bankers from out of town. They were stuck here over the weekend, they explained, because they were working on some big deal. The older one was a senior partner with their firm, the younger one was a junior associate. They wasted no time in buying us drinks and chatting us up. The younger one seemed quite delighted with Janey and was working very hard at impressing him. I could see that all of this attention was making Janey a bit uncomfortable but I was really enjoying the older banker's flirting. He was quite charming and I was starting to have a lot of fun.
After his second glass of white wine, Janey started to relax. He seemed to get into the spirit of the moment and started to enjoy the young banker's overtures. Janey laughed at the young banker's jokes and partipated more in the conversation.
More than an hour went by when I mentioned to the older banker that Janey and I had hoped to get a table at the restaurant but that we didn't have a reservation. "Let me fix that," replied my handsome older banker. He walked out of the bar and returned two minutes later. "Our table is ready," he announced.
Apparently, my new banker friend was a VIP of sorts and when he wants a table, one is immediately made available. Before I could react, Janey and I were being seated at a table with our two gentlemen admirers. Janey was starting on his third glass of wine (and keep in mind, he is too young and shouldn't be drinking at all!) and he seemed to be OK with this unexpected turn of events.
Dinner with our two handsome bankers was lovely. Both were charming and fun. Janey was a perfect lady and played his part perfectly. Maybe too perfectly. As dinner progressed, Janey and his young banker were whispering to each other and giggling. After the salads were cleared, I noticed the banker had his hand on Janey's stockinged thigh -- and Janey didn't seem to mind. And while we were waiting for dessert to be served, Janey and his admirer started making out -- right at the table! I was quite shocked but I wasn't going to interfere. And besides, it made it very natural for me to start a little canoodling of my own with my senior partner.
As my banker was paying the bill, Janey and I stepped into the ladies room for a quick talk. Janey was nearly bursting with excitement. "Mommy, I think he really likes me!" he panted. "He wants me to go back to his room with him. What should I do?"
"Absolutely not, Janey. You've had too much to drink and you have no idea what you are getting yourself into," I replied. I had never even dreamed that Janey would feel this way about a man, worked up in a girlish romantic frenzy like this. And what did he think was going to happen if he went up the banker's hotel room? "Why don't you and your new 'boyfriend' have another cup of coffee down in the lobby and I'll come back and get you in an hour. That should give you some time to...get better acquainted."
So after Janey and his young admirer excused themselves to go to the lobby, my senior banker and I went up to his room for a quick roll in the sack. I expect that he was married, but I didn't care. I was super horny and he was great in bed.
After the hour was up I put my clothes back on and went down to the lobby. There was Janey sitting on a sofa frantically making out with his new boyfriend. I separated them and dragged Janey back upstairs to our hotel room.
My son, Jamie, and I share a big secret. Jamie is Sissy. And while he tries his best to act like a boy at school, at home he is my Sissy daughter, Janey. Over the years, Janey has really blossomed into a delightful young "lady" and I love the special times I get to spend with the daughter I never had.
Last weekend, we had the most wonderful adventure. After Jamie came home from school on Friday afternoon, we drove into the city, which is only a couple of hours away. We checked into our hotel and that's when the real fun began. Jamie stripped off his boy clothes, slipped on a fluffy bathrobe and started becoming my daughter Janey. Over the next hour and a half, Janey and I got ourselves all dolled up for a night in the city.
We finished doing our hair and makeup. I helped Janey zip up the new little black dress that I had bought for him. I let him borrow one of my necklaces and a fun oversized purse. Janey put on his favorite strappy platform sandals and he was ready. Doesn't he look lovely!?!
We then went to the ballet which we both loved! Then we enjoyed a late dinner at a fancy French restaurant. It was marvelous. The waiters fawned over my pretty daughter. One even jokingly begged Janey for a date! Janey was a good sport and giggled and blushed like a young lady would.
Exhausted, we went back to the hotel where we slipped into our nighties and went to bed.
On Saturday morning, Janey decided that he wanted to wear his red dress. It is very simple and yet so elegant. And Janey knows he looks fabulous in it!
We had breakfast at the hotel and then went to the art museum which had a wonderful exhibit on ballgowns from the 18th and 19th centuries. Janey and I both enjoyed this very much. We spent so much time at this one exhibit that we barely saw anything else in the museum.
After we were done at the museum, we walked over to the Ritz Hotel where they serve the most delightful afternoon tea. Janey and enjoyed all the little sandwiches and sweets that were served. Elegantly dressed ladies sat at all the other tables; some tables apeared to have mothers and daughters having tea together -- just like Janey and me! I felt so fortunate to be able to share this experience with my special Janey.
After tea, we spent the rest of the afternoon shopping. At the lingerie shop I bought Janey some new bras and panties and stockings. We then found some shoes for Janey at the big department store -- a pair of black patent leather slingbacks with a three inch heel and some cute sandals for the summer. Then we visited a couple of the designer boutiques and I had Janey try on literally dozens of dresses! In the end we only bought one dress for Janey -- oh, but what a dress.
We returned back to our hotel exhausted carrying all of our new purchases. Since we were tired, we decided that we would have dinner downstairs at our hotel. As we started to get ready for dinner, Janey asked me, "Mother, do you think I can wear my new dress tonight -- the one you bought me this afternoon?"
"Of course, sweety," I replied. "I am sure that your new dress will be just perfect for tonight. The hotel's restaurant is rather fancy and I am sure people will be dressed very nicely. So yes, please wear your new dress."
We finished doing our make-up and fixing our hair. Janey slipped on his new dress and modeled it for me. "Oh, Janey," I sighed. "You look...amazing." A tear started to well up in my eye as I gazed at my beautiful, elegant son.
