A Sissy and his Mother Have a Weekend Adventure -- Part 1

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.

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.

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.

A Sissy Anniversary Surprise

Things had difficult at home for several months.  My wife had known about my interest in crossdressing for several years and had seemed pretty accepting.  However, recently she had been getting very annoyed about how much time -- and money -- I was spending on my crossdressing habit.  She said it was interfering with our relationship.  She insisted that I scale back on my crossdressing activities but I didn't listen.  But as our tenth anniversary approached, she seemed to relent.  As a peace offering, she gave me the most lavish nightgown set as my anniversary gift.  My present included sexy matching shoes, stockings, a sparkly necklace and a gorgeous new wig.  My wife even arranged for a make-up artist to come to the house who not only did my hair and face, but also managed to attach my breast forms in a way that made my cleavage look real.

 

At a few minutes before 8:00, I was ready.  I looked and felt so sexy and feminine and happy.  I turned the lights down low, lit some candles in the master bedroom and struck a sexy pose.  At precisely 8:00, as we had agreed, my wife knocked on the bedroom door.  "Come in," I said in a soft and sultry voice, my heart racing with excitement.

As my wife entered, she immediately turned on the bright ceiling light.  At first I was upset that she was spoiling the romantic mood I had created.  But that's when I saw that there was a tall and handsome man standing behind my wife.  I was paralyzed with shock. 

"Oh my God!" my wife laughed, "I can't believe my sissy husband is actually wearing that ridiculous get-up.  What a pathetic sissy faggot I married."

The man threw one arm around my wife's shoulder and started filming me with a video camera that he held in the other.  "How did you ever convince him to dress up like that?  This is the funniest thing I've ever seen.  Smile for the camera, Sissy!" he taunted.

"Oh believe me," my wife explained, "he doesn't need any convincing to dress up like a little sissy princess.  And now, Sissy, you can dress up whenever you want because now I have a real man to keep me company.  Maybe if you're lucky, someday you can get a real man too!"  They both doubled over with laughter when she said that. 

"Come on Sissy, do a sexy little dance for the camera.  I'm sure that would be a big hit on YouTube!"

Bedtime Sissy