Poker Night Sissy

Every Friday night, Master invites five or six of his friends over for poker night.

Master insists that I get all dolled up in a fancy cocktail dress, 5-inch heels and sexy make-up.   My strapless dress barely covers the large breasts Master forced me to get.  He says I have to look my best when his friends are over.

At 8:00 the guests begin to arrive.  I greet them at the door and take their coats.  Always keeping my eyes lowered, I inform them that I am the "sissy of the house" and that I have been instructed to serve my Master's guests in whatever way they require.  As I say this, I can feel their hungry eyes on my exposed cleavage.  I can tell they are smirking at my humiliation and submissiveness.

For the next four hours, I serve them drinks and snacks.  The men play cards and drink and smoke and laugh.  Mostly they ignore me, but they often grab my ass or squeeze my boobs when I am serving them. They say mean things to me and call me "whore" and "slut" while they fondle me.  When I'm not serving the men, I stand silently in the corner and wait.

Then, promptly at midnight, the men put down their cards.  The game is over and they count their chips.  They carefully figure out who won, who came in second, third, and so on.  Then they line up, the winner in front.  It is now time for me to do what I have been dreading all evening.  I drop to my knees in front of the winner, I pull down his pants and I open my mouth.

The night's winner jams his big dick into my mouth and I suck and lick it eagerly the way Master trained me. The winner's dick get bigger and harder.  He roughly bucks his hips, ramming his cock in and out of my mouth for several minutes.  Then he grabs the back of my head and forces his cock down my throat.  And then he explodes.  He blasts his hot, sticky cum into and I swallow it all.  All the other men hoot and shout as they watch the winner cum in my mouth.

"Next!" Master yells to everyone's amusement and the next man in line drops his pants.  I put his cock in my mouth and let him rape my face.  I repeat this until each man has unloaded his sperm into my mouth.  And for being the night's winner, I have to give the first man a second blow job.

I feel sick and disgusted, with the load of several men in my stomach and on my face.  "Get yourself cleaned up!"  Master yells at me.  "What a whore!" he adds to the amusement of the others.

I race to the bathroom and quickly wipe off my face and redo my lipstick.  I rush to get the men's coats and to see them out.  They usually have something mean to say or enjoy one final laugh at my expense as they leave.  With the final guest gone, I get busy cleaning up after the night's game.

With the house clean and the clock striking 3:00, I enter Master's bedroom where he has been sleeping.  I pull back the covers and begin performing my last blow job of the night on my Master's massive cock.  "You are such a filthy little sissy slut," Master mutters, half asleep, as I begin to cry.

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.

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.

New Sissies at the Beach

Last week I took my two newest Sissies for a day of fun at the beach.  It was a holiday weekend, so the beach was very crowded and my Sissies attracted a lot of attention!

These two fell into my clutches just a few weeks ago.  They are just at the very beginning of their transformations.  Their boyish haircuts are just starting to grow into more sissyish styles -- although I already dyed their hair to a prettier, more feminine color.  They are still very confused and frightened by their captivity and forced transformations.

My newest Sissies were horrified when they saw the outfits they would be wearing.  But their protests subsided after a few whacks with my hairbrush.

And aren't they absolutely darling!?!  I just loved dressing these two up in these identical sissy bathing suits -- with the matching sissy cover-up.  The high waisted panty (with an adorable little bow!) and the training bra tops are simply devine.  And the little pink heartsare just perfect for little Sissies.

I love this photo.  The Sissy in front is about to start crying as I just ordered him to take off his cover-up and let everyone see him in his pretty Sissy bikini!