Sissy Gym Stories

34,000 results
Orientation
Length
Source
Infinite Scroll

A Sissy Saga Ch. 16

by Snurge on Sep 15, 2017
Novels and Novellas

It was after supper, but the evening sun still shone through the lofty windows of the gymnasium to catch dust particles floated weightlessly in its slanting streams of light. A naked young man who promoted the delicate aura of a fragile girl stood fumbling over his words before the seated figure of Miss Twist, groping helplessly for an excuse to explain the...

Sissy Amy Loves Mummy Belinda Ch. 03

by Sissy Adele Howells on Sep 17, 2017
Fetish

Nurse Sue George sat opposite her best friend, Nurse Lynda Christopher. Both looked stunning in their royal, blue nurses uniforms. Lynda was a tall women in her middle forties, with dark, long hair, tied back in a bun. She wore glasses, but was attractive for her age. The best thing about Lynda Christopher, was that she sneezed frequently and enjoyed blowing...

Humiliated

by SissyJane on Sep 16, 2017
Transsexuals & Crossdressers

Mandy is Satan. That's all there is to it. She's made my life hell ever since I met her in Psych 135 class in September. She is one cruel, cruel bitch. I don't know what I'd do without her. They say people secrets want to get caught. They make stupid mistakes or leave evidence around to their secret. Psychologically, they need to break their silence. I su...

Sexy

by SweetOblivion on Sep 16, 2017
Transsexuals & Crossdressers

"Hi sexy," he grinned impishly out at her, blinking his eyes to adjust them to the bright sun, as he opened the front door to greet her. "Is Dora...?" She began and then did a double take: "What do you look like, Marcus?" "Don't you love the ice blue?" Lindsey looked the young man up and down and, smiled, despite the initial shock. He was wearing a pale...

Domestic Bliss

by SadistGoddess on May 1, 2018
BDSM

Every touch from Naomi reverberated with the precondition for pain. Liam knew that, but fuck her hand closing around his dick blocked out the warning from his brain. All thoughts melted away with the mere friction of her wrist stroking up and down the length of him. Naomi was barely even clenching her hand or working it in careful motion; just the feel of he...

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...

Sissy Masochist

by _pdy_ on Sep 24, 2019
Transgender & Crossdressers

I'm writing this because, personally, I really enjoy writing about my sexual desires and turn ons. I find it very taboo to express these secret thoughts for strangers on the internet to see, and to be completely honest, I have a massive hard on as I write this. Well, not massive, quite the opposite actually, but you get the point. Reflecting on my previous...

Basketball Crossdresser

by Cute Little Thing on Sep 14, 2017
Fetish

This story is about an athletic but small man who has fantasized about cross dressing from an early age. When his wife finds a strange number on the phone bill, she calls the number and has a conversation with his phone mistress. What follows contains blackmail, humiliation and of course - sex. If sex and crossdressing offend you, or if you are underage, ple...

How I Became Sissy Willow Ch. 02

by willow619 on Sep 12, 2017
Transsexuals & Crossdressers

"Now the preliminaries are over, and it's time for the entertainment part of our evening!" That was what Fern, my wife, said to me as I lay on the bed after I had been fucked by our newly mutual lover, Jason. I was dressed in pink panties, bra and slip, and a floral sundress. A blonde wig with long curls was on my head, completing the transformation. Fer...

The Desires Within

by Little_panda2412 on Sep 16, 2017
Transsexuals & Crossdressers

This is a special piece for a fan of mine. Thank you for your feedback and I had a blast exploring this new type of work, you know who you are. Thank you. * Hello, my name is Neil Shepard, I'm a thirty year old accountant from Michigan and this is the story of weird (as some people believe) yet satisfying sexual journey. Even at the age of thirty, I'm stil...