Tricked Into Sissy Stories

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Infinite Scroll

Panty Posers Ch. 03

by EROTICbearscribe on Sep 14, 2020
Transgender & Crossdressers

It was early on Sunday morning. I awoke needing to pee and slipped out of bed, doing my best not to wake Daphne. I could hear him breathing deeply next to me most of the covers on his side as usual. My roomie was lying on his stomach, his head under his pillow. He looked so sexy lying there. I felt the warm rays of the sun on my back as I breathed in his cu...

A Sissy Saga Ch. 21

by Snurge on Sep 15, 2017
Novels and Novellas

The next morning Jennifer Hancock went down the stairs with her hair piled on top of her head and wearing a crumpled pale-blue linen overall to be amazed when Lulabelle said she looked as fresh as a daisy. Her mother was talking on the telephone, and when Jennifer appeared in the sitting-room she clapped her hand across the mouthpiece. "I've been negotiatin...

Gordy Gets a Skirt Ch. 02

by KristaMorane on Feb 10, 2020
Transgender & Crossdressers

I wish to thank Mike Lair for feedback, discussing ideas with me as my editor. *** As expected another box arrived before the weekend making him the proud owner of four bras and six panties all free samples from his employer, the lingerie leader, Maidenform. Free in exchange for wearing them daily and giving feedback on fit. He was tricked into the runway...

Owned by my Mother-in-Law Ch. 07

by Sputnik57 on Sep 13, 2017
BDSM

I was released from the haven of my mistress' crotch and she stood by me in a central position, flexing her cane in readiness for my punishment as we watched the gimp's misery. The wickedly pencil-skirted headmistress that was Arabella, placed the black dish from earlier at her feet, and ordered the gimp down to it in full view of the eager crowd of women. A...

Sarah Goes to College Ch. 04

by Sarahcheer on Sep 19, 2017
BDSM

Chapter 4: Sarah before the Court Sarah was utterly beaten, and she knew it. Brian, her owner, had been keeping her locked in a cage at his dorm room for the last week, only letting her out to use the bathtub restroom and to fuck her pussy when he was in the mood. Otherwise, she had been left locked in the cage, forced to wear a VR helmet that had continual...

A Sissy Saga Ch. 04

by Snurge on Sep 15, 2017
Novels and Novellas

The highly polished writing table was uncluttered, the only item encroaching its pristine surface being the letter of application Miriam Hancock had received from Emma Twist, the young woman who now sat stiff backed in the chair facing her. Miss Hancock folded her hands over the pieces of paper and gave the impression of ignoring them as she assessed the ca...

How I Became A Girly Slut Ch. 03

by richfun71 on Sep 13, 2017
Transsexuals & Crossdressers

Copyright 2008 [email protected] To make sense, I recommend reading parts 1 and 2 first.... Samantha, moaned as I lay on the floor underneath her in my school uniform, licking the cum from her freshly fucked arse as she ground herself onto my face, rubbing her clit through her skirt. It seemed to go on forever as she kept orgasming and telling me...

Anthony/Toni

by orvette1 on Sep 16, 2017
Transsexuals & Crossdressers

When I was 15 I was hanging out with some bad guys. We robbed a store, I got caught and went to jail for five years. Anthony, my brother, was only ten when this happened. When I got out of prison my parents told me to not come back to the house. So I moved out of town. Five years after getting out of prison things weren't going well for me. When you are an...

Real Life Adventure of a Cuckold

by stevecraigslist on Aug 18, 2017
Fetish

This is a true story of a recent adventure. Let me know if you like it at the address in my profile and I will post more. * I met Lydia from a posting on craigslist. I was in the habit of posting a variety of ads every week in the casual sex section, trolling for playmates. Sure, the odds of getting a date out of an ad were low, but what was the cost? And...

Revenge Story

by Dark0007 on Jul 14, 2020
Loving Wives

Hi My name is James. I was in the army and after my unit got shut down, I had been trying to earn my bread through a small business of pipe cleaners. It was a complete role reversal for me from being an ex-military assassin to a business man. After the closure of my unit I was in complete depression. I had seen lot of blood my whole life but it all changed...