Sorority Sissy Stories

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HSPL - Trip to the Sorority

by sissydn on Aug 7, 2019
Transgender & Crossdressers

"After being left on the road by Meghan and Sophie, princess was caught by Cindy and her companions. Zoe, apparently the leader in the group, had informed sissy that she could get back to Sophie and Meghan if she pledged the sorority and joined with honor. If she chooses not to pledge, they would drive her to the other end of town and leave her there in her...

Master's Degree in Crossdressing Ch. 02

by wifetoy on Sep 16, 2017
Transsexuals & Crossdressers

This confession is the second chapter of a follow up series to my earlier series "College Crossdressing Confessions." My wife forced me to make those confessions detailing my shameful addiction to wearing panties, pantyhose, and other girly intimates, and my panty pilfering ways in college. While I was making those confessions to the public for the first tim...

Brandi's Turn Pt. 02

by 9volt on Mar 3, 2020
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** So we woke up with my sister looking, mouth agape, at my husband in his torn panties, garter belt stockings and bra and me with a 6-inch strapon cock jutting from my otherwise naked body. There wasn't even a blanket handy to pull over ourselves. There was a pretty awkward silence...

Kelly, the Sweet Slave Ch. 01

by HumiliatrixEnigma on Sep 2, 2017
Novels and Novellas

Act 1 No one has any recollection of her even having parents. An extravagantly rich couple in their early thirties found her, completely unclothed, lying by the side of their man-made lake. Mr. Smith, a naturally observant man, instantly noticed her while he and Mrs. Smith were out on an early morning stroll. As the couple neared her, both man and woman wer...

Master's Degree in Crossdressing Ch. 01

by wifetoy on Sep 11, 2017
Transsexuals & Crossdressers

This series is the follow up to my earlier series "College Crossdressing Confessions." My wife forced me to make those confessions detailing my shameful addiction to wearing panties, pantyhose, and other girly intimates, and my panty pilfering ways in college. While I was making confessions to the public for the first time, my wife has generally been aware o...

The Molly Virus Ch. 04

by Sissyhalo on Nov 14, 2017
Transsexuals & Crossdressers

*Jackie... I used to be called Jackson and I had Jeri as my roommate and she or I thought at first was transitioning. I was never much into being a homophobe and stuff so it was just me kinda leaving things alone. Until Jeri and I started fucking. She's really fucking great in bed too and it was pretty hetero too with me the guy fucking this trans black g...

Spellbound & Sissified

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

SISSY FOR A SPELL The Omega Psi Phi Fraternity loomed in front of him. The lights were on in almost every room. Frank's hopes, that maybe the brothers of Psi Phi were at the Halloween party across campus being thrown by their sister sorority Sigma Gamma Rho, were dashed. He took a step forward. His hand was shaking and the child's Jack O' Lantern bucket...

A College Sissy Ch. 03

by nat_rose on Sep 26, 2017
Transsexuals & Crossdressers

There was the time I was playing hide and seek at my friend's house. I was hiding. I ran upstairs, looking for some place to sneak into so I wouldn't be found. I felt my time slipping, but before it was too late, my friend's sister caught onto the game we were playing and waved me into her room. Her name was Stephanie. I was a shy kid, and my face turned r...

Wife in Control Ch. 01

by wifetoy on Sep 25, 2017
BDSM

I originally posted this story almost two years ago, but lost the other parts of the story when my computer crashed. I am reposting this part and will be posting the other parts of the story over the next few weeks as I finish retyping them. While I may post some fictional stories in the future, all of the events in this one and the other parts to follow are...

He Brought Me Panties

by Cute Little Thing on Sep 14, 2017
Transsexuals & Crossdressers

Ok, here's a quick story and true at that. I was away on business one night and surfing for sex on Craigslist. The title of my post was "If I'm so strait then why do I want to get fucked like a girl?" It was a popular post and I got a bunch of replies, and a bunch of men wanted to fuck me. This made sense and I wasn't that surprised. I'm on the small side, 5...