Shemale Sissy Stories

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Infinite Scroll

Mistress de Sade's Sissy School

by spitzharder on Sep 16, 2017
Transsexuals & Crossdressers

My whole body hurt, everything, both inside and out, the pain had brought me agonisingly awake. I could feel the bars of the cold cage I had been thrown into, it had been my home for several months but the beating was new. The other sissies had turned on me, they might be 'girly' but they were cruel, Mistress Kayne had warned me that to disobey one last ord...

Sissy Fantasy to Nightmare

by Anon729 on Sep 16, 2017
Transsexuals & Crossdressers

My first ever story here so I would appreciate any feedback. Hope you enjoy it! ***** Sunlight drifted gently through the hotel room as I woke up and rolled over to feel the warmth of Rosie next to me. "Morning sleepy head," she greeted me with a smile. "No time to waste if you're getting ready for the stag." It was just 3 days until our wedding and the...

When Mom's Away

by tenk on Nov 18, 2016
Transsexual

"Honey, wake up. I'm leaving on my trip, I'll only be gone today and Saturday." My mom whispered to me as she shook my shoulder. Your mom was nearing fifty but still looked amazing, huge tits and a large ass. "Happy 18th birthday, I love you. I left your presents on the kitchen counter. Sorry I can't be here, but I'll be back Sunday Morning. R...

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Hades University for Men

by Testytesterton on Mar 15, 2020
Fantasy

Welcome to Hades University, a place of myth, magic, and potent masculinity. You are a first year student, enrolled without your knowledge, by a father you have never known. As you were raised by your human mother, you had no knowledge of you mystical, possibly infernal legacy from your father's side. Suddenly, on your 18th birthday, you started developing i...

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Made to Obey Ch. 08

by madetoobey on Jul 29, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...

The Society Ch. 05

by Barno on Sep 19, 2017
Transsexuals & Crossdressers

"I don't think that I'm the right person for this. You need someone more experienced. What if I fuck this up? I'll get my balls snatched right out from under my cock!" I was more than a little nervous watching Serena and Corinna rifle through my closet. "Your balls were snipped off quite a while ago my dear and the woman who owns them has given you her orde...

Seven Lessons Ch. 01

by Vertex on Sep 16, 2017
Transsexuals & Crossdressers

(1) - Acceptance Bryan was king of the road warriors. Speeding around the country in his sleek, powerful Mercedes selling whatever his latest job demanded. He was damn good at it too, always raked in huge amounts of commission until some faggotty client bitched about a one-sided deal he had put together and then it was off to another company. Talking of bi...

Sex therapist

by qaz on Sep 1, 2016
Miscellaneous

Who do we follow?What's next? A boy A girl What's next? A boy A girl...

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Girlfriend Trouble

by lovelymess212 on May 29, 2019
Fantasy

You've been dating Sam for a long time, even thinking of popping the question sometime soon. She's perfect in every way, and its near your second anniversary. You have your own apartment together, living with each other to count on. Maybe life is far from perfect, but you have each other. Of course, sometimes life throws you a curve ball. You wake up one mor...

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Mamma Mia - Forced Femme

by ppeaks42 on Sep 16, 2017
Transsexuals & Crossdressers

"We need a little more feminine energy around here." The words hung in the air as Tommy's devoted licking of Mia's ass slowed to a stop. "You mean another woman?" Mia hooked her legs behind Tommy's head and pulled his face back into her ass. "No, I mean you, you dumb sissy bitch." Once Tommy finished with pleasuring Mia, she led him into her closet. She...