A Sissy's Dinner Date Fantasy -- Part 3

I couldn't go out with Mark again on Saturday because I had already lined up a date with another man!  This guy's name was Jake Martin. He was in real estate and he wanted to take me to Le Maison too! I decided to wear my new dress and shoes again but I wanted to do something different with my hair. I called a salon that was willing to arrange my wig into a different style. They offered to do my make-up while they worked on my wig so that's what I did.

My second date with a man was even more exciting than the first. Jake was charming and funny. But he was also pretty aggressive. From our first few moments together in the restaurant, he had one hand on my stockinged thigh under the table, stroking and squeezing. At first it made me nervous, but after a glass of wine I decided I enjoyed it.  

The food and wine were just as wonderful as the night before and I was having a great time being an elegant lady in the company of a handsome man. 

At one point during the evening, I got up to use the ladies room, When I returned, Jake stood and pulled up my chair for me. How chivalrous, I thought. But as I sat and he pushed in my chair, he leaned in and started kissing my neck. I was so surprised, I almost fainted. And he wouldn't stop doing it until I insisted!  

By the time we were having our dessert and coffee, the restaurant was emptying out. That's when Jake really made his move. He pulled up his chair close to me and we just started making out -- right there in the restaurant!  I know that the waiters and the few remaining guests were staring at us, but I didn't care. 

As Jake was paying the bill, he practically insisted that I go back to his house with him.  And I agreed!  We took our separate cars and I followed Jake to an elegant townhouse at the edge of downtown.  Once inside, Jake turned on some music and opened another bottle of wine.  We sat down on the couch and started making out again.  Wow!

Before long, I found my hand was on his lap, stroking his enormous, stiffening cock through his trousers.  He started breathing hard when I did that and he suggested that we go back to his bedroom.  Knowing that would lead to big trouble I suggested that we stay on the couch. I unzipped his pants and his huge dick sprang out.  Without even thinking, I put my head in his lap and wrapped my lips around his giant cock.  I licked and kissed and sucked on his cock for over twenty minutes until he finally had to cum.  And when he did, it was an explosion!  I swallowed every drop of his precious semen. 

It was almost 3:00AM by the time I finally got home. And even though it was very late, I couldn't go to sleep.  My mind raced with emotions from my exciting weekend with two different men. And the feeling of having a real man cum in my mouth while I hungerly sucked on his dick! For the next several hours all I could think about was how much I wanted to see both Mark and Jake again, to feel their lips on mine, to feel their desire for me, to excite them in the ways a real woman would.  I couldn't sleep at all that night wondering where this would take me next. Would I explore my girlish feelings with Jake or Mark -- or did I need the thrill of having many more men pursue me and desire me?   

A Sissy's Dinner Date Fantasy - Part 2

Within a week of posting my profile, over 200 men had written to me!  I read every single message that I received. Then I carefully studied each man's profile and photos and I wrote flirty notes back to several of them. It didn't take long before I had actually scheduled a date with one of them!

For my very first date I had selected a man that seemed particularly promising. He name is Mark Jensen and he was in his mid-40s, divorced and a bank executive. He described himself as being six-foot-two and in excellent shape. And best of all were his photos! He was very handsome, with strong, chiseled features. His dark hair had a bit a grey at the temples.  One of his photos was taken at the beach -- with his shirt off exposing his muscular chest and shoulders!

We exchanged several emails and then we talked on the phone. I had practiced my girly voice and he didn't suspect a thing. In fact, he said my voice was sexy. And at the end of our conversation we agreed to meet for a date on Friday night!

I couldn't stop thinking about my big date all week. Even though I owned two pretty dresses that I could have worn, I decided I needed something even more special. I went to Macy's and spent $400 on a gorgeous black dress and another $200 on some sexy sling-backs with 3 inch heels.

On the night of our first date, I met Mark at Le Maison, the fanciest French restaurant in town. He was already sitting at the bar when I walked in. He looked just like his photos -- tall, handsome, sophisticated. He seemed very happy when he saw me for the first time. He gave me a quick peck on the cheek as he greeted me and the Maitre d' walked us to our table.  

My dinner date was just heavenly. Mark was a perfect gentleman and I felt like a perfect lady. He ordered a very expensive bottle of wine which was wonderful. We chatted about this and that. Mark mentioned several times during dinner that I looked very pretty -- which made me blush each time. Being with Mark made me feel like I was one of the beautiful, enchanting women in the romance novels I had read. 

We had a second bottle of wine and our conversation became flirtier. I was having so much fun -- it was like a dream come true.  

As dessert was being served, Mark got out of his chair and gave me a big kiss -- right there in the restaurant! It was so spontaneous and so romantic!

After dinner, Mark walked me to my car in the parking lot. But the evening didn't end there. We made out in the parking lot for another twenty minutes. Mark pressed me up against my car while he frenched me hard. He was so strong and forceful. I could feel his dick getting hard as he rubbed against me. It was so exciting!!! His hands even drifted up to feel my breasts -- he had no idea he was squeezing silicone falsies. He practically begged to see me again on Saturday, but I said no -- not because I didn't like him, but because I already had other plans for tomorrow night!

You see, I had already arranged a date with another man for the very next night!

After I got home from my exciting first date as a girl, I put on a sexy nightgown, some soft music and made myself cum, looking at Mark's profile photos, imagining that our wonderful date hadn't ended in the parking lot.

A Simple Minded Sissy

Poor Sissy Gretchen.  His transformation had been particularly difficult.  He had resisted the process every step of the way.  He simply would not cooperate with the plans I had for him.  But I knew he would make an exceptionally pretty -- and valuable -- sissy once the transformation was complete.

Through a combination of drugs, hypnosis, electroshock and beatings, I was eventually able to break through his resistance and complete his conversion.  And I was right -- I was able to transform this young man into one of the prettiest sissies I ever made.

Aided by a daily dose of narcotics, Sissy Gretchen becomes a simple minded little sissy who no longer has any will of his own.  He will obediently follow any instruction given no matter how demeaning or disgusting.  That makes him the perfect sissy escort.  I have a long list of wealthy men who have no problem paying me thousands of dollars for a few hours with this gorgeous and completely docile sissy love doll.

At the end of every long day of sissy sex servitude, Sissy Gretchen has an unusual bedtime routine.  He strips off his pretty dress and slips into a sexy, sheer and very revealing baby doll nightgown. Then he allows me to put a ball gag in his mouth and to tie his wrists and ankles to the bedposts.  Sissy Gretchen falls asleep, content and mindless.  I leave his bedroom light on.

These bedtime preparations are required because during the hours before dawn, Sissy Gretchen will awaken as yesterday's dose of narcotics begin to wear off.  As his brain begins to refocus, he remembers who he was -- and what he has become.  I expect his mind is flooded, all at once, with images of his feminized self submitting to the disgusting demands of his many male clients.  The terror he experiences is amplified by seeing his own gorgeous sissy reflection in the mirrored ceiling above his bed, his enormous breasts barely concealed by his sheer baby doll nightie.  He writhes in mental agony on top of his bed, struggling to free himself from his lashings.  His screams muffled by the bright red ball gag in his mouth.

I allow this to continue to a couple of hours until I am ready to get out of bed and deal with poor Sissy Gretchen.  By then he is a wreck, overcome by his exhaustion and horror.  I stand above him and tease him.  "Oh, what's the matter sissy?" I might say.  "Don't you like staring at your sexy reflection in the ceiling mirror?  Aren't you happy that you are now a perfect sissy slut?  Didn't you have fun yesterday -- and everyday -- doing all those nasty things you did to all those men?"  It doesn't take much to get him to start sobbing.

Eventually I take pity on him I inject him with today's dose of narcotics.  He slips back into unconsciousness for a couple of hours.  When he awakens later, the episode he experienced just a few hours earlier will have been completely forgotten, as he begins another day of obedient sissy sex servitude.

After School Sissy -- Part 3

Last Friday afternoon, when I came home from school, I went straight to my mother's room to do my make-up and put on one of her dresses like I do everyday.  As soon as I was satisfied that I looked pretty and girlish enough, I got busy on my chores before it was time to start making Stepfather's dinner.  As I was dusting upstairs, I went into my bedroom and discovered that my bed was gone.  When Stepfather came home I asked him what happened to my bed.

"Oh, I decided that you wouldn't be needing that old bed any more," he said.  I didn't understand what that meant, but I know he doesn't like it when I ask a lot of questions, so I let go.

After dinner, we went to the den and I climbed onto Stepfather's lap like usual to watch TV.  He wrapped his big arms around me, and started stroking me through the satiny dress I was wearing.  But after just a few minutes he let out a big yawn and announced that he was tired and wanted to go to bed.  "Come with me," he said.  "I have something to show you."

He took my hand and led me up the stairs to his bedroom.  I noticed that one of my mother's nightgowns was laid out on his big bed. 

"I want you to put that on," he said.  I knew better than to argue, so I picked up the silky nightie. 

"Okay," I said.  "I'll take this to my room and I'll try it on."

"No," he replied.  "You can change right here."

So I unzipped my dress (I mean mother's dress) and let it fall to the floor.  Stepfather seemed to enjoy watching me as I did this.  I unlaced my corset and pulled off my stockings.  I was about to take off my bra, but Stepfather said to keep it on.   While I was undressing, Stepfather started rubbing the front of his pants with his hand and was breathing hard.

I carefully pulled the silky nightie over my head, being careful not to mess up my wig or make-up.  The nightie was extremely feminine and sweet.   It had little ruffly cap sleeves and was trimmed with several ribbons and bows.   "Walk around," Stepfather instructed.   "Yeah, that's nice," he said as I paraded around the room. 

After a few minutes he handed me another one of mother's nighties.  "Here," he said.  "Try this one on."  I did as he instructed.  I modeled several nightgowns for him that evening.  He decided that he liked the one I tried on last the best.  It was soft pink with white applique flowers trimming the neckline. 

"Yes," he said.  "Keep that one on."  He kept staring at me, his hand still rubbing his erection through his pants.  I felt so exposed just standing there in th sheer nightie.  I held onto the back of the chair while he continued to stare at me. 

After a few minutes, he came out of his trance.  He said that he was going to go to the bathroom, and that when he came out, he wanted the lights dimmed and the candles lit.  I didn't like where this was going but I didn't argue.

I prepared the room the way he asked and after a few minutes he emerged from the bathroom.  He was completely naked!  He ran at me and literally pushed onto his bed.  He fell on top of me, all of his weight -- and his erection -- pressing down on me.

"This is the way things are going to be from now on, Lydia," he stated, calling me by my mother's name.  "Now spread your legs."

Sissy Gets Ready for his Master

The Sissy heard his Master open the front door and enter the home.  "Oh dear," the Sissy thought to himself.  "My Master is home early and I'm not at all prepared for him."

The Sissy quickly ripped the flowery dress he had been wearing off his delicate frame.  He ran to the bathroom and grabbed a bottle of "Feminine Lubricant" and leapt into the bed.  He tore off his little lacy panties and rammed the tube of lubricant into his "Sissy Pussy."  He gave the tube a hard squeeze and he gasped as he forced half of the tube's icy cold lube up his "pussy."

Lubricated, the obedient Sissy positioned himself as instructed on the bed just as his Master entered the bedroom.

"Well, look at you," the Master said with great satisfaction.  It looks like you've been waiting for me and my cock all day.  Is that true?"


"Oh yes, Master, yes," the Sissy panted in reply, as he was trained.  The Sissy felt a wave of relief, having narrowly avoided a severe beating for not being ready for Master's return home.


The Master approached the bed.  He rubbed his sexy Sissy's soft bottom, and then gave it a stinging slap.  He laughed at the pain he inflicted on his Sissy.  He unzipped and lowered his pants.  His huge cock sprang out and he mounted his defenseless little Sissy love doll...

A Sweet Sissy Nest

While some Sissy Trainers I know prefer to work with just one Sissy at a time, I prefer to train mine in groups of two or three.

I find that in groups, forcibly transformed Sissies form an odd and powerful dependence on one another.  A weird bond is forged among Sissies as their masculinity and ability to think for themselves is stripped away, replaced with fear, uncertainty, obedience and confusion.  My Sissies cling to each other like sweet little Sissy Sisters.

I force my Sissies-in-Training to do everything together -- eat, dress, bathe, accept punishment -- everything.  Here is a photo of my latest crop of Sissies-in-Training snuggled up close for their afternoon nap.  The twin bed that the three of them share becomes a cozy Sissy nest.  Isn't that sweet!

Sissy's DisneyWorld Vacation -- Part 2

We got up early the next morning.  Today we were going to Epcot!  I asked Stepmother for the clothes that she had bought for me yesterday.  "Of course,"  she said, "I got you a nice shirt and some jeans to wear today."

Well, I opened the bag and was horrified by what I found.  "But this is a GIRL'S tank top.  And these aren't boy's jeans -- these are girl's capri pants!"

"No shit," replied Stepmother.  "Now put them on and let's go.  Or don't you want to go see Epcot?  And don't you want some more 'nightie fun' with me tonight like we had last night?"

"But, but, but,"  my head was spinning. "I can't go to Epcot dressed like a girl!"

"Of course you can.  No will know but me.  Now hurry up  and get dressed."

Well, I did as she commanded.  Once I had the tank top and capris on,  she put a little make-up on me and brushed out my hair.  "There!  You look lovely!  Just another teenage girl at Epcot.  Now let's go!"

We did go to the park and no one seemed to notice that I wasn't a girl.  In fact, it seemed like a lot of boys (and a lot of grown men) were staring at me.  Stepmother said that they were staring because I was so pretty and they were imagining having sex with me.  Yuck!

After a while I began to relax and focused less on the fact that I was dressed like a girl.  And Stepmother was really nice to me all day.  She must have taken 200 photos of me that day!  All day long she called me Alice and seemed to really be enjoying having me dressed up like a girl in public.

We were exhausted from our busy day when we returned to the hotel.  We took quick showers and I didn't protest when Stepmother told me to put on my nightie.  Stepmother brushed out my hair and did  my nails.  I enjoyed being treated so gently by her -- even if it was a little strange to be dressed as a girl.    After we turned off the lights, Stepmother once again started carressing me and whispering in my ear what a pretty girl I was.  I lay back as she gently stroked my stiff little cock through the silk of my nightgown.  In just a few moments she made me cum -- all over my nightie.  She raised the cum-covered hem of my nightie to my mouth and made me suck my cum off of it.  "That's a good little Sissy," Stepmother said.

The next day we went to Disney Studios.  This time Stepmother handed me a flimsy little sundress and some flip flops to wear.  I tried to protest but of course, in the end I did what Stepmother told me to do.

I was really nervous and uncomfortable wearing the little dress.  I felt like everyone -- especially all the boys -- were staring at me.  I felt half naked.  I worried all day that my skirt wouldn't stay down and everyone would see my panties. 

Stepmother and I had a wonderful time at the park.  She told me about a thousand times how cute and pretty and sexy I looked in my little flowered dress.  She took tons of photos and even some video of me having fun in the park wearing my pretty dress.

And of course, at the end of the day, Stepmother and I returned to our hotel for what she called "nightie fun."  I was in heaven.

The next day we were going to the Magic Kingdom...

Sissy's DisneyWorld Vacation -- Part 1

I was so excited that my Stepmother was going to take me on vacation -- to DisneyWorld!  I had always dreamed of going to DisneyWorld.  Our trip was planned for late October when I had a short break from school. 

I really don't like my Stepmother.  She is not nice to me.  Ever since she caught me once trying her clothes, she has insisted that I wear girls clothes at home whenever my father is away -- which is very often because he is in the Navy and is sometimes away for months at a time.  She says that I am a pathetic Sissy Faggot.  She makes me cook and clean and she beats me for making even a tiny mistake.  She made me practice my make-up, my voice, my walk -- everything -- so that now I can really look and act like a girl.  She hasn't let me get a haircut for nearly a year and now my hair is starting to get pretty long.

Anyway, I thought the vacation might mean that maybe my Stepmother was going to start being nicer to me...

On the day of our trip, the limo came to the house very early.  Everything seemed to be in a big, frantic rush to get out of the house.  Unfortunately, in our rush, it seems that my suitcase was left behind.  Stepmother was very, very angry with me, saying that it was all my fault that my suitcase was left in the house.  She slapped me hard across the face, calling me a "Stupid Sissy Faggot" -- right in front of the limo driver, who just laughed at my humiliating treatment.  There wasn't time to go home and get it so Stepmother said that she would have to get me some new clothes when we got to Florida.

When we arrived at the hotel and entered our room, I saw that it only had one big bed, not two smaller beds.  When I asked Stepmother about it she just said that this was the only room the hotel had available and that it wasn't a problem and that would just share the bed.  That sounded very strange to me...

I hung out in the hotel room while my Stepmother went shopping for some new clothes for me.  She seemed very happy when she returned.  We ate room service for dinner.  When it was time to get ready for bed, Mother noted that since I didn't have any pajamas I would have to borrow one of her nighties to sleep in.   She handed me  a pretty, clingy black silk nightie that was trimmed with lace.  I didn't argue because she had been so angry with me earlier.  I put it on and she gushed about how pretty and sexy I looked in it.  She insisted on putting my hair in a ponytail and taking some photos of me -- which she often did when she had me dressed as a girl.  She put the camera away and I climbed into bed. 

A few minutes later, Stepmother emerged from the bathroom -- wearing the exact same nightie!  That was so strange.  Why would she pack two identical nighties for a vacation to DisneyWorld?  I was beginning to think that my suitcase wasn't left behind by accident...

Stepmother turned off the lights and climbed into bed.  She snuggled up very very close to me, rubbing her hands all over my silk covered body.  She whispered in my ear that I was beautiful and that it made her excited to dress me up like a girl.  It made me very uncomfortable and frightened and confused to be cuddled and carressed by Stepmother like this.  But I was also getting excited from her touch.  My little cock became stiff and Stepmother wrapped her long fingers around it.  She stroked my cock and whispered in my ear, "I am going to start calling you Alice.  Cum for me now, Sissy Alice!"

And I did.

Bedtime Sissy