A Reluctant Sissy -- Part 5 -- Elegant Nights

When I opened my most recent update letter from Mrs. Trainer, these two photos fell out of the envelope.  I must have stared at them for five whole minutes before I could tear myself away from them to read her letter to me.

"Dear Mrs. ____, 

I am very pleased to report that our progress with your son is proceeding very, very well.  An entirely new personality is being revealed; One that is demure, gentle and obedient.  I am sure you will be delighted when you see the finished product in just a few short months from now.

Now that our sissy students have been with us for 16 weeks, the intensity of the training and our expectations of our "ladies" increases quite dramatically.  Days are longer, infractions are dealt with more severely and our behavior and personality manipulation (some might call it brainwashing) is taken to a new level.

We are very fortunate that our school is located just a few miles from a Royal Air Force base.  Over time, we have developed a relationship with a select group of senior officers from the base that we can trust.  Every Thursday night, we invite our officer friends over for a very swanky party with our darling sissies.  The officers tell their wives that they are working late (seems to happen every Thursday!) and our sissies entertain these handsome gentlemen from early in the evening until well past midnight.

We dress our sissies up in their finest outfits to show the officers how much we appreciate their company.  And it should be no surprise that your little Kimberly is one of the officers' favorites!  The gentlemen arrive -- in full dress uniform, of course -- around 6:00pm.  It's cocktails and flirting with the sissies.  Then dinner at 8:00 followed by more cocktails, dancing and...well, whatever the officers want to do.  We have plenty of space here at the school for the officers to take a sissy somewhere private for some one-on-one time.  This goes on for a few more hours until our gentlemen guests are exhausted and need to head home to their families.

You may be curious as to why we incorporate some much interaction with men into our training program.  Let me explain.  First, when our sissies are in the presence of alpha males, like our wonderful RAF officers, they are shocked into realizing just how little they have in common with such real men.  Being surrounded by strong, masculine, muscular men, our sissies feel small and delicate and weak.  They recognize nothing of themselves in our handsome guests.

Second, it is understood by all that the sissies are to cooperate with and please our guests at all times.  Our officers are accustomed to having their instruction followed and their needs met.  It is wonderful practice for our sissies to understand that their role is only to please and to serve.  At this point in their training, they are beginning to feel a sense of fulfillment, and even pride, in their submissiveness and servitude to these strong, dominant men.

I will write again with more photos as soon as I can.

Sincerely, Mrs. Trainer"

I put away Mrs. Trainer's letter and again marveled at the photos of my beautiful, elegant, ladylike son.  I could just imagine how these older gentlemen would absolutely drool at the site of such a lovely young "girl."  And while at first I was shocked by the thought of him being forced to endure...encounters...with men, I could see Mrs. Trainer's point that it was probably a very powerful indoctrination and re-education tool.  I reminded myself of just how bad his behavior was before I sent him away and how I was in favor of whatever Mrs. Trainer felt she needed to do to fix his awful behavior and attitude. 

 

Mommy's Pajama Sissy -- part 7

 

Tammy was having a magical time at the fancy tea dance, being led on the dance floor by his handsome date, Steve.  Tammy allowed himself to be carried away by the experience, resting his head on Steve's shoulder.  And when Steve leaned in to kiss Tammy, Tammy didn't resist at all.  Deep kisses continued on the dance floor as the band played a slow, romantic song.

"I'm going to miss you when I leave for New York on Monday. Do you think you will be able to visit me?" Steve said.

That question triggered something in Tammy's head that he decided to act on.  "Steve," Tammy whispered in his ear as they danced, "I haven't been completely honest with you."

"Oh, really?" Steve replied, having no idea what he was going to hear next. "Well, now might be a good time to set the record straight. I'm ready. Let me hear it."

"Well," Tammy said softly into his ear. "For one thing, I'm not really 22 years old like I said last night. I'm 18."

"Yikes!" Steve responded with real surprise. "That makes me much older than you. I really shouldn't be dating 18 year old girls. Well, at least you're...legal.  I'm going to need to think about this. But in the meantime, please lay off the champagne.  You shouldn't be drinking."  Tammy agreed.  "Was there something else? Steve asked.

"Well, yes," Tammy started. "This is a bit hard to explain, but I wasn't exactly born this way. I mean, gender-wise.  I haven't always been a girl like this."

"Are you saying that your trans?" Steve whispered back to Tammy. "Wow, that is a surprise. But you're so...feminine. I would never have thought. I suppose you transitioned when you were young.  Wow, there is a lot to learn about you!"

To Steve's credit, he seemed more concerned with Tammy being 18 than the fact that his date was a transwoman.

"It's not exactly like that," Tammy whispered back. "I...I...I," Tammy stammered.

"You what?" Steve prompted, struggling to keep his voice at a whisper.

"Steve, I'm a boy," Tammy explained simply.  Steve went a little pale. 

They retreated back to their table where Steve said, "Look, there is a lot we need to talk about but we can't talk here. I was planning to take you out to dinner later, but maybe we should just go back to my folk's place and talk in private there.  Is that OK with you? Tammy agreed and off they went.

Mommy's Pajama Sissy -- Part 6

When Steve returned from the rest room, I made an excuse that I saw friends across the room that I wanted to talk to.  That gave Steve and Tammy some alone time.  When I returned about 15 minutes later, Steve said that he needed to leave so we said our good-byes and he left.                                                                                                                 "Well?" I said to My Little Princess.                                                                                                              "He asked me out for tomorrow.  And I said yes." Tammy replied with a bit of embarrassment in his voice.  I squealed with delight at the news and gave Tammy a bit hug.  Tammy gave me the details.  Steve's family belongs to a fancy country club just outside of town. There was a "tea dance" scheduled for Sunday -- tomorrow -- afternoon.  Steve would pick up Tammy at 2:00 and head over to the club.                                                                                    "Oh what fun! I think the little black dress we bought yesterday would be perfect.  Don't you agree?" I said.                                                                                                                                                                 "I guess so," Tammy replied uncertainly. "I don't really know about any of this..."                                                                                                                "Oh, don't be nervous. We'll make you the prettiest girl at the dance and you will be full of confidence. But for now, we should get home so you can get a good night's sleep before your big date tomorrow!"  And so we left. 

Sunday morning was very busy with getting Tammy ready for his big date with Steve. After breakfast, we spent all morning making Tammy look his prettiest.  We did his hair and his make-up.  He wore some of the new underwear we had bought at the mall just two days ago.  He slipped on his pretty new black dress, its straps accentuating Tammy's delicate shoulders, its neckline plunging intriguingly low.  I lent Tammy a chucky necklace and some strappy black sandals that went well with his outfit.                                                                                     "Mother," Tammy asked as he was admiring his own reflection in the mirror, "Don't you think I need to be honest with Steve about....everything? I mean, it doesn't seem very nice to be tricking him this way."                                                                                                                                               "Well," Mother replied, "I think you will need to figure out what needs to be said and when over time.  Don't worry about it too much right now.  Just try to have a good time and enjoy the experience. But if you decide at some point that you want to give Steve the truth, well that will be up to you.  But be thoughtful -- actions have consequences."                                                                                        Tammy was still thinking about his mother's advice when, at 2:00 sharp, Steve pulled up to the house in his BMW and off they went.                                                                                                                       Well, Tammy had never been to a fancy country club, let alone a tea dance, even as Tommy.  The experience was thrilling for him.  The valet parked Steve's car and Tammy entered on Steve's arm.  Waiters were passing trays of champagne and Tammy took one and drank it quickly.  Steven found a little table near the window where they sat and chatted. Older couples -- friends of Steve's parents, Tammy figured out -- would stop their to say hello to Steve. Each time Steve would proudly introduce Tammy as "his friend."  Everyone was friendly and polite.

When the jazz ensemble started playing again after a break, Steve asked Tammy to dance, and Tammy agreed. Tammy was really starting to relax, having had three glasses of champagne by this point in the afternoon.  "Why did they call it a tea dance if all they served was champagne?" he wondered to himself, as Steve led him to the dance floor and wrapped his arms around his pretty date.                                   

Sissy Priscilla Part 3 -- Mother's Wedding Surprise

After I had taken about a million photos of my beautiful sissy son bride, I told him that we should head back inside.  I could tell he was sad when I said that, sensing that our bridal fantasy day was wrapping up.  But I had other ideas.  In fact, the fun might be just beginning!

As I said earlier, sissies have such limited lives -- no friends, no romance.  But I knew I could change that.

You see, at the same time that I was making arrangements to rent the cottage and buy flowers for today, I had also gone online to see if I might be able to find a fantasy "groom" to make Priscilla's wedding fantasy complete.  There are plenty of websites out there for men looking to meet sissies. My challenge was to find the right one.  I posted some details of what I was planning for my little sissy and, needless to say, I got hundreds of responses from horny men wanting to have some dirty action with my sweet sissy son.  But one profile stood out from all the others -- a young, tall, handsome man, clearly well educated.  He seemed to understand what I was looking for in a "dream date" for Priscilla.  I arranged to meet him in person and I liked him immediately. His name was Kurt. 

So on the day of Priscilla's wedding, while Priscilla and I were taking photo's outside, Kurt arrived at the cottage and waited patiently for us inside. When he saw us starting to walk back toward the cottage, that was his signal to come out.  Little Priscilla was so frightened and worried when this tall man walked out of our cottage and started walking straight towards us.  "Now, now, Priscilla," I reassured. "Don't be frightened.  In fact I know this man.  His name is Kurt and I invited him."

Priscilla looked so confused and scared.  Kurt confidently strode up to Priscilla.  "Hello, Priscilla," he said.  "I am Kurt.  Your groom.  Your husband.  For today." 

Well, it took some time for Priscilla to compose himself after much reassurance from me. "Come, come, Priscilla," I said.  "Play along.  This is all part of making today's fantasy complete."  After a while, Priscilla relaxed, mostly because Kurt was so charming and gentle with him.  Before too much longer, I was able to get Priscilla to smile and pose for some photos with Kurt.  Here's the first photo I took.


Well, after the first photo was done, I was able to take about two hundred more as I asked them to pose in various locations around the pond.  With each passing moment, Priscilla became more relaxed around Kurt and seemed to ease more naturally into his role as the petite bride to Kurt's manly groom.

"Now a kiss!" I shouted.  Priscilla was shocked when I said this.  Kurt wisely went in for a gentle peck on Priscilla's forehead.

"Oh that won't do at all!" I cried.  It's time for a real kiss."  And I guess Priscilla agreed.












Kurt pulled Priscilla hard against him as Priscilla closed his eyes and allowed Kurt to kiss him for a very, very long time. I was delighted to see my little sissy son experience romance for the first time in his life.  I took dozens of photos of this lovely embrace.



We went back inside the cottage where I insisted that Kurt and Priscilla act out a wedding ceremony while I took even more photos.  I had arranged for some wedding flowers for the living room to set the mood.  

"Do you, Kurt, take Priscilla to be your wife?" I intoned.  "I do!" said Kurt while Priscilla beamed.


"And do you, Priscilla, take Kurt to be your husband?"  "Oh yes, I do!" replied my eager and delighted sissy son.  "You may kiss the bride." I instructed Kurt.  And Kurt did as I told him, scooping Priscilla up in his arms and kissing his lovely bride.



















"And now for your first dance as husband and wife!" I shouted and pressed play on the CD player.  John Legend's "All of Me" began to play.  Kurt expertly led Priscilla around the living room in a gentle, slow, romantic dance.  As the song came to an end, I decided it was time for me to make my exit.  "Well, three's a crowd," I said.  There's a light dinner and a bottle of champagne for you two in the refrigerator.  I will be up in my room.  Have fun.  And congratulations!"  Priscilla giggled as I left.


At about 6:30 the next morning I heard Kurt leave the cottage and drive off in his car.  I came downstairs and found Priscilla, in his vintage peach peignoir set, sipping on a cup of coffee, looking rather disheveled -- and a bit embarrassed.

"Well, well, well," I said. "And how is the new bride this morning?"

Priscilla waited a moment, finally answering, "A bit sore, actually."  We both broke out in laughter when he said that.  I gave my sissy bride son a great big hug.  

"I hope you enjoyed your wedding fantasy, darling," I said.

"Oh yes mother.  That was the most wonderful day -- and night of my life."

Kurt continued to be a frequent visitor at our home after Priscilla's sissy wedding.  But those are stories for another time.

A Boyfriend for my Sissy Husband -- part 2

A week passed and it was time for Danielle's second date with his new "boyfriend," Martin.  Of course, Martin wasn't really Danielle's boyfriend - he was a man I picked to construct a wild psycho-drama for my sissy.

Danielle was all giggly and nervous before Martin arrived to pick him up.  Unlike last week when Danielle was terrified of being out with a man, tonight I could tell he was excited and looking forward to it.  Something deeply feminine and girly had been awakened by his first date.  It was as if Danielle was being flooded all at once by the emotions of a 15 year old girl!

Danielle had begged me to take him shopping for a new dress to wear.  This was going even better than I could have dreamed!  Danielle explained that Martin wanted to take him to The Windsor for their second date.  The Windsor is a very exclusive and very expensive restaurant and after hours club with wonderful food and live music and dancing.  Danielle was all aflutter with the idea of being asked out on a date there.  I agreed to take Danielle shopping and we bought a very elegant purple dress for him to wear.

When the big day arrive, once again Danielle spent most of the afternoon at the beauty parlor getting all prettied for his date.  The girls at the salon made him describe every minute of his prior date.  They told Danielle how lucky he was to have such a handsome and charming man pursuing him and taking him out to really fancy places. Instead of becoming anxious by their chatter like he was last week, this time Danielle was flattered and encouraged by it.

Martin picked up Danielle and took him away for the evening. Here are some photos of the two of them on the grand staircase heading downstairs to the club after they finished with their dinner. It was another dreamy dinner date for Danielle -- his girly feelings completely overwhelming his natural heterosexual tendencies. 

Danielle was much more relaxed than he was on their first date.  And Martin was much more flirtatious.  After the wining and dining, the lovebirds moved to the dance floor, where Martin expertly led Danielle as the combo played a variety of slow, romantic songs.  Danielle felt so safe in Martin's strong arms.  Danielle felt like he was floating on air, twirling and swaying in his lovely purple dress and 4 inch sandals.

When they couldn't dance anymore, Martin navigated them both to a sofa where they sat.  Martin said, "Danielle, I know I only just met you, but I want you to know that I already have very strong feelings for you.  Danielle, I'm falling in love with you."

Danielle's heart must have almost stopped beating when he heard this. Before Danielle could open his mouth, Martin took out a small wrapped gift from his pocket.  "Here, Danielle, this is for you."  Danielle nervously accepted the small box from Martin and opened it. Inside was a beautiful heart-shaped pendant covered with about a dozen diamonds.

"Oh my!  It's lovely!  I...I don't know what to say.  This is all so unexpected!" Danielle managed to sputter.

"I'm sure it is," Martin said calmly as he helped Danielle put the necklace on.  "You don't have to say anything.  But I do want to see you again.  And soon.  And for longer. And for more."  Danielle looked confused so Martin elaborated. "Next Saturday, let's spend the whole day together. Here's my idea.  We can drive over to the lake and get room for the day at the Inn on the Pier.  We can get to know each other better, if you know what I mean."  Now Danielle knew exactly what Martin meant.  Danielle knew this was not something that he should agree to but he couldn't help himself.

"Okay," Danielle said.  "But I can't tell my...spouse.  I know that meeting you was all her idea but I don't think she would approve of me checking into a fancy hotel with you."

"Not a problem," Martin responded.  "All of this can be our little secret.  You can tell your...spouse...that I have planned a full day of activities together downtown, we'll go to the museum, then lunch, then a matinee...I will pick you up at 9:00 and have you home by 6:00.  And no one will ever suspect what we're up to."

"You are a devil, aren't you, Martin Rittenhouse?" Danielle replied with a wide grin, barely able to contain his delight that this handsome man was pursuing him as if he were the most beautiful woman on the planet.

There was more kissing and groping in the car before returning Danielle home.  I again was waiting in the living room.  Danielle gave me a report on his evening, delighted in sharing details of the dinner, the dancing, the music.  But he did exclude a number of details.  He said nothing about the necklace he received (he must of taken it off just before coming inside), nothing about Martin's profession of love for him, and nothing about their sneaky plan to screw around in a hotel next Saturday.

Of course, Martin kept no secrets from me.  And I fully expected my pathetic sissy husband to mislead me about what was really going on between him and Martin. Danielle didn't know it, but he was quickly digging himself into a hole from which he might never emerge. 

A Sissy every Weekend -- Part 7. After the Dance

Caroline followed me back to the bedroom.  She sat down on the edge of the bed and gently placed a hand on my shoulder.

"I'm sorry I teased you like that," she said.  "I really do appreciate what you did for me tonight.  And I would like to show you how grateful I am."

I had no idea what she was suggesting.

"Now take off your dress and put on your nightie and I will be back in a minute."  Caroline disappeared into the bathroom.

I forced myself to stop crying and dried my eyes with a tissue.  I stripped off the pretty dress, the stockings and the bra and panties I had worn to the dance and slipped on my pink nightgown.  Caroline emerged from the bathroom wearing only her bra and panties and carrying a bottle of lotion and a small towel.  "Now I want you to just lie back and relax," she said as she sat on the edge of the bed.  She looked so beautiful wearing just her underwear.  I tried not to stare but I couldn't help it.

As I laid back, Caroline lifted the bottom of my nightgown.  She squeezed some lotion onto her palm and began to gently stroke my little penis.  I had never felt anything like this before.  Here was the girl I loved so much, wearing only her bra and panties, giving me a hand-job!  My little penis instantly became erect.  As Caroline stroked me I tried not to think about how much different I must be than her boyfriend Robert.  Robert was big and strong and masculine; I as dainty and feminine, my skin was soft and my cock was tiny.

I couldn't believe this was really happening.

Caroline stopped pumping for a moment.  "Now don't make any noise, Sweetie.  We can't let anyone know what we are doing.  Do you promise to be quiet?"  I quickly nodded in agreement.  Caroline resumed playing with my cock with her soft, lotion-covered hands.

"Does that feel good, Tiffany?" Caroline whispered into my ear as she continued to pump my little penis.  "Ohhhh, yes," was all I managed to reply.

And then I started cumming.  My little cock just exploded, spurting and spurting, over and over.  Caroline smiled down at me while I orgasmed.  "Well," Caroline said.  "It looks like someone really enjoyed that!"  She kissed me on the forehead and went into the bathroom to wash her hands.

When Caroline returned she again at on the edge of my bed.  "You really were wonderful to go to the dance with me tonight."  She stroked the my cheek with her soft fingers.  "Now get some sleep."

She moved to her bed. "Oh, by the way.  Robert's parents have invited you, me and Mark out for brunch tomorrow morning.  I already said that we are going. It will be fun and I know Mark will enjoy seeing you again.  And if it all goes well, who knows, maybe I'll be able to show you how grateful I am again."  With that Caroline turned off the light and climbed under her covers.

Caroline was completely manipulating me.  She knew she had me under her spell and I was powerless to resist.  Tomorrow I would be out again -- with a boy who thought I was really a girl.

I struggled to fall asleep, but when I did, I had dreams about Caroline -- and Mark.

A Sissy Every Weekend -- Part 6 The School Dance Continued

Well, the dance wasn't as awful as I had feared it would be.  In fact, I guess it was sort of fun.

Robert and Caroline and Mark and I arrived at the dance around 8:00.  Caroline's high school gym had been decorated with balloons and streamers and fancy lighting.  We spent the first hour or so chatting with Caroline's friends and their dates.  Everyone was very nice to me and several girls told me that I looked very pretty.  After a while I started to relax.

I relaxed a lot more after taking a few swigs from the flask that Robert had sneaked into the gym.  Caroline drank more than me but it didn't seem to effect her very much.  But just a few sips made me feel a little tipsy.

The band started playing some slow music and Mark asked me to dance.  I knew this was going to happen at some point but I was very nervous.  He took me by the hand and led me out to the middle of the dance floor.  He wrapped his arms around me and we started swaying to the music.  He told me that I was very beautiful and that he was having a great time being with me.  Before I could say anything back, he kissed me!

I was so surprised that I almost fainted when he did that.  I was about to pull away from him but then I realized that being kissed by Mark wasn't so terrible.  I also realized that I enjoyed how it felt being held tightly in his strong arms.  I looked up into Robert's eyes and I let him kiss me again. This time he put his tongue in my mouth!

We danced together for a few more songs.  I could feel that his dick was hard as we danced together -- it felt like his dick must be huge!  I tried not to think about that as I placed my head on his strong shoulder and wrapped my arms around him more tightly.  His hands slid down my dress and he started feeling up my bottom.  It felt strange to be caressed by another boy this way.

The rest of the evening flew by.  The music ended and it was time to go home.  We said our good-byes to Caroline's friends and got back into the car and Mark drove us home.  I let Mark hold my hand as he drove while Caroline and Robert made out in the back seat.

When we got back to Aunt Jenny's house, Caroline and Robert went up the front door to say good night.  I stayed behind in the car to say good night to Mark.  He leaned over and starting kissing me again, really hard and really deep.  I let him.

He made me promise that I would see him again before he unwrapped his strong arms from around my skinny shoulders.  I walked up the steps to Aunt Jenny's house and gave Mark a little wave before he drove off.

When Caroline and I went inside, everyone was still awake and waiting for us.  "How was it?"  "Did you have a good time?"  "How was the band?" Mom and Aunt Jenny and the twins showered us with questions.  Caroline did most of the talking and reported that the night had been really, really fun.

"Well, Tiffany, did you have fun?  And what was Mark like?" Aunt Jenny asked.  The twins were anxious to hear my answer.

"Yes, the dance was pretty fun, I guess.  Mark seemed nice enough," I blandly replied.

"Nice enough!" Caroline replied with a big laugh. "I thought Mark was going to get you pregnant right there on the dance floor!"

That made me so embarrassed that I burst into tears and ran straight up to our bedroom and fell onto my bed, sobbing into my pillow.

A Sissy Every Weekend -- Part 5. The School Dance

"Oh please! Oh please! Oh please!" Caroline begged.

"No!" I said. "Why can't one of your friends do it?"

"Because they are all going to the dance already!" Caroline explained.

"Well then ask one of the twins to go!"

"I already told you. The twins are upperclassmen and they aren't allowed at the Freshman/Sophomore Spring Dance," Caroline responded.

"This is crazy!" I insisted.  "I am not going to a prom!"


"But it's NOT a prom!" Caroline insisted. "It's just a school dance. Robert's cousin, Mark, is visiting from Arizona next weekend.  Robert's parents say that Robert can't go to the dance unless Mark can go too.  Please, Tiffany!  If you don't go as Mark's date, then Robert can't go with me. PLEASE!"  She looked like she was about to cry.

I hated seeing Caroline so upset.  I knew that going to the dance with Robert was important to her. "Oh, alright. I'll go. But only as a favor to you."

"You're the best, Tiffany! Thank you!" Caroline gave me a big hug and then ran off to call Robert and let him know that she had found a date for his cousin.







The week went by quickly and the Friday of the dance arrived.  Mother took me out of school early so that I would have plenty of time to get ready for the dance.  When we arrived at the house, Aunt Jenny had already laid out five or six of her nicest dresses for me to choose from.  Mother suggested that I wear the tailored, sleeveless, pink dress with a blue floral pattern.  I slipped it on and it fit perfectly.  At 5:00, a lady arrived at the house to do hair and make-up for Caroline and me. We were finally ready at 7:00 when our dates, Robert and his cousin Mark, arrived.  I was surprised to see that Mark was driving Robert's family's car but then remembered that Mark was a couple of years older than us and had a drivers license.

It turns out that Mark was very tall and and handsome. And he seemed to like how I looked too.  When we were introduced, he came right up to me and gave me a kiss on the cheek.  Nothing like that had ever happened to me before!  I was really embarrassed because everyone was watching when he did that.  But it also felt sort of nice.

Mother insisted on taking pictures of Caroline and me with our dates and then we headed off for the dance.

A Sissy and his Mother have a Weekend Adventure -- part 3

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!

The Sissy Debutante Ball

Mother had been dressing her son Jimmy up as "Ginger" for years.  At first Jimmy had resisted but his mother was very strong-willed and Jimmy was weak.  Over time, Jimmy stopped fighting his feminization and accepted what his mother was doing to him.

"I had always wanted to have a daughter," Mother told him a million times. "But unfortunately you were born a boy.  But just because you were born a boy doesn't mean I can't make you into my daughter." 

So ever since he was a little boy, Jimmy spent most afternoons -- and every weekend -- dressed as Ginger. And while wearing his pretty party dresses and nightgowns, Ginger and his Mother would spend countless hours doing things that mothers and daughters do.  Mother taught Ginger how to do his make-up and his hair and his nails.  They would do chores around the house like cooking and cleaning and ironing.  At night they often watch chick-flicks together while wearing their pretty night gowns.

So Ginger was brought up to be a perfect little Sissy.  But Ginger was growing up and tonight they would celebrate the lovely Sissy lady that Ginger had become.  Tonight was the Sissy Debutante Ball!

Tonight, nearly fifty Sissies, aged 18 to 20, and their Mothers would celebrate the long and sometimes difficult journey of raising a son to be a Sissy.  Mothers from all over the country brought their lovely Sissy darlings to this lavish affair at a posh hotel in New York City.  

Ginger and his Mother looked heavenly in their coordinated, custom-made outfits.  Mother wore a tailored suit of beautiful golden silk jacquard. Ginger wore a long gown -- made of the same gold silk jacquard as her mother.  Ginger's gown made him look sweet and sexy at the same time. Ginger and his mother had spent most of the aternoon at the beauty salon. Their hair and make-up were perfect.

Even though he looked very beautiful, Sissy Ginger was so nervous as he and his mother rode the evevator down from their hotel room to the ballroom below.  Sissy Ginger didn't know what to expect. 


They made their entrance when the Master of Ceremonies announced their names over the speaker: "Presenting Sissy Ginger and his Mother, Lady Annette!"  The other guests clapped as Ginger and his Mother entered the room.  Ginger was quite stunned by the applause and by the flashes of cameras capturing his big entrance. They found their seats, Lady Annette at one of the Mothers' tables and Ginger at one of the Sissies' tables.

As Ginger introduced himself to the other Sissies, he noticed there were several other tables in the ballroom that were occupied by men. Ginger asked one of the other Sissies who the men were.

"Don't you know?" answered one the other Sissies with surprise.  "After dinner is finished and the announcements are done, the Mothers will all leave and go to another room for the rest of the evening.  That's when the men are free to talk to us and dance with us and..."

"And WHAT?" Ginger asked, somewhat panicked.

"Well, they can ask us to come up to their rooms with them, of course.  And you are not allowed to refuse.  That is all part of the Sissy Debutante experience.  Tonight we become real Sissy Ladies with the Gentlemen that pick us.  Are you saying that your Mother never explained this to you?"
Poor Sissy Ginger.  He nearly fainted when he heard this.  Of course Mother had never told him about all this.  He would have been too terrified to even come here tonight.  

Tears started to well up in poor Ginger's eyes.  "Here, take this," said one Sissy offering Ginger a Xanax and a glass of champagne.  "Just relax and remember that this is what your Mother wants for you.  You need to be brave and do what your Mother expects you to do."

The other Sissy was right, thought Ginger as he downed the pill and the champagne in a single gulp.  "May I have some more champagne?" asked Ginger trying to prepare himself for the frightening evening ahead.  "A lot more."

The Sissy Behind the Curtain

"Martin!" my wife shouted, "Get out here.  NOW!"

My wife had caught me dressing up in her clothes a few weeks ago -- and she didn't like that one little bit.

"Don't be shy, Martin!" she continued.  "We all want to see how pretty you are."  My wife and her lover were waiting for me in the Master bedroom.  They both started giggling when she said that.

I had been dreading this moment.  During the afternoon, my wife had spent hours getting me ready.  First she did my make-up and pinned a curly brunette wig on my head.  Then she dressed me in a sexy red outfit including some strappy high heel sandals that she had picked out for me to wear tonight.  She even put some of her jewelry on me.



"WE"RE WAITING!" she yelled.

I reluctantly stuck my head through the curtain that separated the Master bedroom from the dressing area.  I saw my wife and her lover, both half naked, wrapped in each other's arms sitting on the bed.

"Come on now," my wife called.  "Come all the way out here.  Don't keep us waiting any more."








I tentatively pulled back the maroon curtain and stepped fully into the Master bedroom.

"OH MY GOD!" her lover shouted.  "I can't believe this!  What a Sissy!  He really does look like a girl!"

"Can you believe I actually married a Sissy faggot like that?" my wife asked.

"Now do that sexy dance I taught you," my wife commanded.  And with that, I began to sway and rock, wiggling my hips in a sort of burlesque dance.   "Oh yes!  That's soooo sexy!"  my wife yelled.  And with that, the couple on the bed broke down into fits of laughter.

After a few minutes my wife told me to stop dancing and to come stand next to the bed.  "Now you just stand there and watch while a real man fucks me."  As she said that, the two lovers stripped off the rest of their clothes.  My wife's lover was a big, muscular man with a huge cock.  I just stood there, wearing my sexy red lingerie, while he climbed on top of my naked wife and started fucking her.  I couldn't fight back the tears as my wife started screaming with pleasure, being fucked by such a masculine man. 

After they were done fucking, my wife sat up and looked at me with disgust.  "Aw, is the widdle sissy sad because he's feeling left out?  Well don't cry, sissy.  We have something very important for you to do.  Now get on your knees and clean my man's cock with that pretty sissy mouth of yours."

I did exactly as I was ordered.  As I wrapped my painted lips around this giant cock I realized my life would never be the same again.