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.
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. 
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.
