Mother and her Sissy Son Plan a Trip

"But mother," Eric protested.  "I don't want to dress up like a girl!"

"Oh, not this again," mother replied with a sigh.  "Stop your fussing and let me see how you look in the blue dress.  Hmmmm.  That's very cute on you.  The skirt has a pretty flare.  Now hold the skirt out like you're going to curtsey."

"Marvelous!" she exclaimed as she took another photo.  "That dress will be perfect for when we go shopping in New York City next weekend."

"But mother, PLEASE!" he said.  "Why do I have to be dressed as a girl when we go to New York?"

"As I've told you a million times," mother replied impatiently, "You are going dressed as a girl because you are much too pretty to be a boy!  And besides, a mother/daughter trip will be such fun!"

Ever since Eric had been a little boy, his mother enjoyed playing dress-up games with him.  He didn't mind too much.  In fact he even enjoyed it.  But recently, mother had been insisting that Eric spend more and more time dressed up as "Erica". 

"Now try on the black one with the spaghetti straps," mother instructed.  Eric did as he was told.  He didn't have the spine to stand up to her.  And deep inside, a small part of him enjoyed being feminine.  But things really were beginning to go too far, he thought.

He slipped on the little black dress and his mother zipped him up.  "Oh my!" she squealed.  "That is just ADORABLE on you.  Turn around and let me see.  Oh yes.  You are simply lovely in that! That will work for going out to nightclubs.  You will certainly get a lot of attention looking like that!" she teased.  Eric hated it when she said things like that.

Eric started getting angry.  "And I hate wearing my hair like this!  I look so...girlish all the time.  All of the boys at school make fun of me.  And they can tell that I shave my legs when I go to gym class."

"Oh don't pay any attention to those silly boys," mother said dismissively.  "Sweetie, that's the way teenage boys get when they see a pretty girl and start getting...excited."

"MOTHER!" Eric shrieked.  "I'm not a pretty girl!"

"Hush now," mother replied calmly.  "Don't be silly.  You are very VERY pretty!  Now try on the long sleeve wrap dress."

Again, Eric complied.  He was too much of a sissy to fight back. 

"Oh my! Oh my!" mother said.  "You look so sophisticated in that dress."  She had Eric put on a pair of black lacy stockings and she slipped a necklace around Eric's neck before taking some more photos.  "That dress will be perfect when we go out to dinner.  I made reservations at some of the best restaurants in New York while we're there."

Finally mother had Eric try on vintage black dress with sheer sleeves a feathery trim around the neckline.  It was a beautiful, exquisitely feminine dress.  Mother took several photos and purred, "Oh Erica, darling.  That dress is just heavenly on you.  You look so beautiful."  At that moment, mother decided that Eric would wear this dress to his interview at the New York Sissy Academy.  Mother desperately wanted Eric to attend their famous one-year "Total Conversion" program so she could at last have the daughter she always wanted.  Eric didn't know anything about this part of the weekend plans.  But Mother was so confident that he would be accepted to the Sissy Academy that she had only purchased a one-way plane ticket for her Sissy son.

A Sissy Hooker

When the people at the "New York Transformation Institute" offered to finance my feminization surgery, I should have been more suspicious. But they showed me how beautiful I could become if I elected their very expensive "super premium feminization surgery" package.   I knew I couldn't afford it, but I was powerless to resist.

When the surgery was complete, I was indeed as beautiful as they promised me I would be. My face, my boobs, my hips -- everything was perfect and sexy. They even made my waist super skinny! It was all beyond my wildest dreams!  I wasn't just beautiful -- I was hot!

But now I was deeply in debt. I had no way to pay back the $85,000 I now owed the NYTI. But that was their plan all along! I am now an indentured servant -- a slave -- because I can't pay my bill.  And if I don't pay them back, they said they will kill me! 

I am forced to work for them as a sexy sissy hooker.  Everyday, I am dressed up in some skimpy, whorish outfit and made to stand behind the bus terminal waiting for men to drive buy that are looking for prostitutes.  Then I either give them blow jobs right in their cars or let them drive me to the motel near the warehouses.  The men I have sex with are mean and dirty and I feel sick everytime I have to let one of them cum in my mouth or on my face.

My doctor/pimp says that if I work really hard, I might be able to pay off my debt in fifteen years.  Until then, I will spend every day of my life as a frightened, cum-soaked Sissy whore.

My Sissy in the Tub

I have always loved my husband very much.  He has always been kind and gentle and generous with me. 

But after his second heart attack, I insisted that he quit his high pressure job and make some...lifestyle changes. 

That was three years ago.   Now, with my guidance, my husband who was once a powerful executive has been transformed into the most delightful and feminine Sissy gurlfriend. 

Here we are in the tub enjoying our time together.  His pale skin is soft and smooth and so beautiful.  His hair has grown long and is now a lovely shade of red.  And his breasts!  They are magnificent!  I simply can not resist playing with them. 

And our love life has never been better.  Of course his little tiny cock can't even get hard anymore.  But my husband can spend hours with his face between my legs bringing me orgasm after orgasm with his talented little tongue.  When that isn't enough for me, I let him fuck me with a strap-on.

And when it's his turn for a little pleasure, I wear the strap-on, sometimes still wet with my juices, and fuck his little sissy pussy.