Sissy College Stories

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Infinite Scroll

Maid in Heaven

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Many years ago my Mum worked as a bridal consultant for a well-known wedding dress shop. One day to get off College so I could bunk rugby I complained of having a stomachache. The situation was ridiculous. I'm a young man of 19 who had volunteered to continue with my education and study accounts so why the authorities insisted I had to do Rugby as part of th...

Wife in Control Ch. 03

by wifetoy on Sep 25, 2017
Fetish

This is the third chapter in the story of my submission to my wife for punishment for failure to control my orgasm. My full offer of punishment for my transgression is fully set out in the first chapter for your reference. Each part of this story is true and is told as it actually occurred. As with the previous chapters, my wife told me to let the readers kn...

Butch's Bar Slut

by sissymissyct on Jan 7, 2020
BDSM

(A bit darker than most of my tales. It would fit in gay or nonconsent as well. Gay sex, sissy sex, chastity and punishment.) *** I love this bar, Butch thought to himself as he finished another beer. And why shouldn't he. It had everything a Leather Bear could want. Plenty of hot men in leather, and some women as well. A bunch of trans girls and some siss...

Cheap Sissy Whore To Call Girl Ch. 03

by HardSoft on Sep 15, 2017
Transsexuals & Crossdressers

My first few days at the hospital wasn't the typical hospital stay. I'd get fucked by everyone who worked there. Most of the time I was too dazed to realize what was happening but there was always a cock or a pussy that needed attention. The doctors would come in during their breaks to ass fuck me. The nurses would make me lick their pussies clean. I didn't...

College Stud Takes My Girl

by easyballs on Sep 14, 2017
Fetish

Thanks again go to 'Jill' -a friend - for first requesting my assistance, for her supplying the idea, plot and direction. Also thanking her, for her continued support throughout; If reading pornographic stories offends you go and read some other form of written work! ***** Julie and Tom were both high school students, about to move on to college, having g...

Toby

by Sissyhalo on Sep 4, 2018
Transsexuals & Crossdressers

I found my real self the start of this year. A sissy gurl. Okay so, going back I sucked at being a guy. All through high school I never got laid. Not even close. I was a little short compared to the good looking guys at five six, I had unfortunately this whole soft chin thing and was never conventionally good looking. Add that to me being poor. Oh ye...

The Neighbor Daddy Next Door

by ddogg44 on Jun 4, 2019
Transgender & Crossdressers

PART 2 (continuation of "college is a time to explore) Daniel awoke with the feeling of a lacy black thong riding up his ass. A raging hard on pulsed in rhythm to the sound of Text messages being received. It was the next day, and Daniel was due for a spanking by his next door neighbor "daddy" for getting some cum on the carpet. "Be here at noon, keep th...

Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...

Cockland Island Pt. 01

by Sissyhalo1 on Oct 8, 2019
Transgender & Crossdressers

It’s actually called Huntington Island. And it’s been around a long time and most of us in the area didn’t know much about it except they brought in guests and stuff by sea plane and set out for a lot of food and deliveries. I mean it was a mystery and not around town. Most people worked there from town ended up staying there because it was this private re...

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...