Short Sissy Guy Stories Spitroasted Stories

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Trixie's Chastity 02

by trixie47cd on Sep 13, 2017
Transsexuals & Crossdressers

Tammy, the maid took me away to shower quickly in an upstairs bathroom. I was only given about 3 minutes to scrub off the caked on sperm from the guests at the party, then Tammy helped towel me off and completely re-do my makeup. Goddess had packed a dark brown wavy wig that gave me a secretary or teacher look, but the navy pleated skirt was short enough t...

Scorned Bitch

by lyzunchik on Sep 16, 2017
Transsexuals & Crossdressers

"I'm assuming this is not entirely business," I asked Rod when I meet him for drinks after work. He's a fellow businessperson and we collaborate on some projects. I provide technical and consulting services that augment his contracts with various businesses and government agencies. "No, not really, but I thought it an appropriate segue to get you here fo...

Oliver's Twist

by phoenixcinders on Jan 23, 2019
Transgender & Crossdressers

Hello! Thanks for clicking on my story, I hope you enjoy it! It contains lots lewd acts I should warn you about. Including but not limited to big giant black Transgender dick going into a small tight white boy butt. White boys being spitroasted. White boy sucking a woman's cock. A little bit of blackmail and coercion, but the white boy ends up loving it. All...

Daddy's Sissy Staircase Ch. 03

by SissyLoniOR on Sep 28, 2020
Transgender & Crossdressers

This is part 3 of a 3-part series, to understand better, go back and read parts 1 and 2. Thanks for everyone's comments, this has been my first story here at Literotica, and I have ideas for many more. Please feel free to contact me with ideas for future submissive sissy slut stories! My visits to Daddy now typically involve more time than just during the...

Breaking with Traditions

by Canadagander on Sep 17, 2017
Loving Wives

Copyright © 2005. All characters, events, and text in this story are purely fictional, and are created by and the sole property of the author. All rights reserved. - - - - - - - - - - - - - - - - - - - - - - - Writer's Note: It's time for Canadagander to make a public disclosure, to come out of the writer's den, so to speak. 'Gander is not a real person....

Office Cumslut Ch. 01

by DrLuverotica on Sep 12, 2017
Loving Wives

FRIDAY MORNING "Are you going to work dressed like that Jo?" My wife was dressed in black, sexy high heels, black stockings with a pink 1920s style pencil line up the back of them, pink frilly satin panties (she hates thongs) and matching push up bra. "Yes I am hubby," she purred, as she pulled a navy blue, short pleated skirt over her hips. "Is there s...

Nice Guys Finish Last

by SluttyJanice69 on Oct 24, 2018
Loving Wives

Note: Everyone in this story is 18. Also, I know no one in this story is married, but Loving Wives still seemed like the most appropriate category. Enjoy. ***** Tyler was nice. A consummate gentleman. He always treated me so well. Never pressured me into anything. Always said the sweetest things and thought up tons of great little romantic gestures. He was...

Sammi Starts Camming

by Sissy_Sammi_ on Dec 3, 2017
Transsexuals & Crossdressers

Sam had always been rather small and feminine. As a guy puberty seemed to have missed him which left him in the rather uncomfortable position of being very girly. He was only about 5'8" with a womanly rounded face, smaller waist, and slightly larger hips. He had brunette hair, which for a guy was on the longer end. His lightly tanned white skin pieced with...

Sissy/Cock Sucker Dictionary

by silkstockingslover on Jun 12, 2019
Reviews & Essays

Summary: A list of terms to aid in understanding the activities and nature of sissies and cock suckers. Note 1: The author's source material isn't Webster's Dictionary or anything similar, but is drawn from many years of interest in matters sexual and countless conversations, both spoken and online, with other perverts. Note 2: Thanks to Tex Beethoven and...

He Changed Me

by Sissyhalo1 on Dec 23, 2019
Transgender & Crossdressers

I know a lot of these stories are about some guy that watched porn or read it and got hooked or were some short femmy guy that got tricked into getting boned but that's not me. I'm Sam and yeah it's Samantha most of the time now. But before that it was just Sam and I was in my last year in college and to save money to fix my car I moved into a rental house...