Shemale Sissy Stories

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Teacher Made Me into Sissy

by johntamilandrea on Sep 13, 2017
Fetish

HI! I am Sissy Andrea. This is one my fantasies about my teachers. This story is about feminization, fantasy. If you don't like these topics Please don't read. ALL THE CHARACTERS IN THIS STORY ARE ABOVE 18 YEARS OF AGE. My special thanks to "mywifesslave" for helping me in editing this story. ***** The story happened when I was 19 years old I loved sho...

I was Scott Tenna

by tre34harr on Sep 19, 2017
Transsexuals & Crossdressers

If shemales aren't your thing don't read on; if they are please read enjoy and have your eyes opened. ***** "I hold my hand up and tell you truthfully that I used to be a guy; just like you or like any other guy you know or have met in your life time; into the normal thing a typical uni male student of his age would be; girls, drink, football and cars. H...

Brad's Adventure

by nancyvasquez on Aug 28, 2018
Transsexuals & Crossdressers

Brad was restless. He woke up with a raging hard on. He cast a glance over at his wife. She was on her side, snoring. He knew better than to wake her up. He got out of bed and went into the living room and began watching shemale porn on his laptop. Brad loved shemale porn. Most of the T-Girls incorporated the physical appearance of females, but with the sham...

How it began

by Thehypest1 on Apr 15, 2019
Fetish

You wake up after a long night of drinks with Casey. You hear the jarring sound of the alarm echo in your head. You think to yourself 'How much did I drink last night.' Your head is pounding and you lay in bed for a bit before heading to the kitchen to get water. You run into Allyson there. She made breakfast, she really is too kind. "Good morning, slee...

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Mommy Adriana, I Will Obey You

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

Dear Readers, since I am open to suggestions from now on I will start my stories with a recap of what has happened before. * Finally we were on our way home. Interestingly neither Mommy Adriana nor Mistress Andrea had cuffed or gagged me. So I just sat in the back of our car. During the short drive I had some time to think about what had happened in the p...

Sissy for the Family

by sissyboi4daddy on Aug 21, 2018
Transsexuals & Crossdressers

Hi, my name is Isaac. I'm 21 years old, Asian and a child of divorce. My father decided he wanted nothing to do with me the moment I was born, and my mother held 2 jobs to raise me. When I was 18, she decided she had enough of the hard life and remarried. She remarried Jack. Jack was a white, bordering on obese man, who was 12 years older than my 42-year-o...

My First Time as a Sissy

by SissyTara on Sep 13, 2017
Transsexuals & Crossdressers

I had moved away from home to go to college at 18. I had been cross dressing secretly for a few years. I would sneak into my mom's closet and "borrow," her clothes. I had my own apartment my parents were helping to pay for. I also had a part time job and was able to buy a few feminine clothes for me to wear. I loved the feeling of wearing women's clothes but...

Have we met before?

by HYjaCK on Jun 1, 2020
Bisexual

Light shone through the curtains, blinding you momentarily as you sat up, taking in the environment around you as there's a knock at the door. Struggling to think, you stand up automatically, putting on a discarded red robe and staggering to the door. Leaning against it, the door knocks once more. "H-hello? Room service!" A female voice from the ot...

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Sissyhood of Travelling Panties Ch. 01

by daddyslittlebitch on Sep 14, 2017
Transsexuals & Crossdressers

Chapter 1: Alex A pair of red satin panties lay on the bed. They were boyshort style with little red lace bows above the crotch. Very sexy and very slutty. Helen ran her fingers along the soft, smooth material. She was dressed in a black lace garter belt holding up thigh high stockings, her large, round breasts, still firm at the age of 45, stood out naked...

Pokemon Grunt

by Cantalope on Sep 25, 2018
Fan Fiction

Things had been rough lately. It wasn't all one thing, though plenty of them were enough to put you down in the dumps, it was the combination of all the things together. You were having a hard time keeping your life together and all this stupid world seemed to care about was pokemon and training to fight with them. What about goddamn health care huh!? Sure t...

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