Shemale Fucks Boy Stories

119,352 results
Orientation
Length
Source
Infinite Scroll

Neighborhood Good Boy

by Kami107 on Feb 13, 2020
Transsexual

Brian had recently turned eighteen, he was finally a man. Although he didn't quite feel it. He was much smaller than the other boys around his age being only 5'4" and weighing in at a measly 120 lbs. With black hair, pale smooth complexion, skinny but proportionate limbs and wide hips that contoured his firm bubbly butt, his effeminate features didn't q...

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Ex-Cellmate Looks Him Up

by SugarandSalt on Sep 11, 2017
Transsexuals & Crossdressers

Everything was going to be perfect. Nathan hummed an upbeat tune to himself as he set the table. His girlfriend would arrive for their dinner in any time now. Nathan checked the food simmering on the stove for the second time in as many minutes. He heard a knock at the door. "Be there in a minute," Nathan called out from the kitchen. He quickly ran a comb...

Amy Finally Lives Out Her Fantasies Ch. 02

by LuvAGoodPegging on Sep 11, 2017
Transsexuals & Crossdressers

(Author's Note: This is a continuation of "Amy Finally Lives Out Her Fantasies -- Shy Amy uses her strapon on Kyle". Thanx to all who provided such great feedback. Hope you like part two. Warning: this story contains male/female strapon sex, cum eating, and as the category suggests, shemale sex. If those aren't your things, you won't enjoy this story. Love t...

Pam's Shemale Experience Ch. 10

by majicman21 on Dec 2, 2019
Transgender & Crossdressers

Pam woke up, and as she remembered what day it was, a smile crept across her lips. Earlier in the week, her owner had decreed that she would not fuck Pam until Wednesday. That had been Sunday night, and now, with Monday and Tuesday past, today would be the first time in a long time she would feel that magnificent cock opening her up. It's been too long.....

Lady Denisa's Gang Banged

by gonzi2 on Sep 14, 2017
Loving Wives

The young black youth aged eighteen was lying on the bed while I mounted him for the third time that day. I used his cock and muscular body shamefully to bring myself off with no thought for his pleasure. Kenny was my toy boy, an aircraftsman from the base my husband commanded when he wasn't away on active duty. I'm Lady Denisa forty-seven year old wife of...

Pool Party

by GuyIncognito06902 on Sep 26, 2017
Celebrities & Fan Fiction

Happy to share this story with you. This one is a bit odder than the usual fare and I warn you going in that this story involves well hung celebrity shemales. I kind of wanted to save it as a surprise twist, but that seemed a bit unfair to have the story seem like a typical lesbian celebrity story and then have it be about girls with hot cocks instead of cun...

Pleasure World

by Robopoop on Jan 20, 2020
Science Fiction

(( Author's Note: Once again, in my fit of inspiration, I leave behind a mess that makes little sense or impact. This post and all others later written by me will be undergoing significant amounts of intensive editing. Otherwise, feel free to post anything you like. The thread has been set to Public after all. Note 2: Posts are notorious difficult to organiz...

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Pool Party Ch. 02

by GuyIncognito06902 on Sep 26, 2017
Celebrities & Fan Fiction

It's time for a sequel and if you like imagining beautiful celebrities as hot, hung dickgirls with big tits and big cocks then this is the place to be. I hope everyone likes it. This story is COMPLETELY fictional and not meant for people under the age of 18. This is all fantasy and not any kind of reality. The story codes for this are FF, FF+, orgy, shema...

Jabba's Shemale Slave Pt. 01

by mkh78 on Sep 24, 2019
Celebrities & Fan Fiction

This story is from the imagination of the writer and inspired by Return Of The Jedi. ***** The Hutt's sexual appetite was growing. He had been thinking about expanding his harem of gay sex slaves to include a transsexual. This was all due to a drug dealer who caught the eye of the exalted Hutt. Although they had done business only two times in five months...

Pam's Shemale Experience Ch. 11

by majicman21 on Jun 1, 2020
Transgender & Crossdressers

Content warning: one scene with a golden shower. "Ah, what a way to start the day," Tanya sighed, letting her cock slip from Alex's pussy. The shemale had just filled it with a load of cum, dribbles of that gift already leaking out. Pam smiled from next to them, at the possessive yet affectionate way Tanya slapped her cock onto one of Alex's thighs and...