Shemale Pegging Stories

2,414 results
Orientation
Length
Source
Infinite Scroll

Pinch Hitter Ch. 01

by npanxx on Sep 14, 2017
Anal

This is a work of erotic fiction. All characters in the story are over the age of 18. ~~~~ My fascination with shemales had cost me my first marriage. I guess if I were to be honest with myself I would have to admit that the marriage was doomed to fail anyway. Barbara was as close to being asexual as a person could get, and in addition she was bitchy a...

HypnoSissy: Educated to be Pegged

by silkstockingslover on Aug 13, 2019
Fetish

Summary: Cock sucker's training is advanced to hypno videos on anal sex. WARNING PLEASE READ: -This is a hypnosis story with potentially influential subliminal messages within it. -The story also contains hypnosis video scenes. -So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to...

Made to Obey Ch. 08

by madetoobey on Jul 29, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...

A Masseuse Named Eve

by Legatus on Sep 13, 2017
Transsexuals & Crossdressers

This is my first submission, I hope you enjoy it. I tried to focus on character development, so this may be a bit longer than most are used to. **WARNING: This story contains a hermaphrodite/dickgirl/shemale with an inhumanly large cock and lactating breasts. There's shemale on male sex, lactation, and unrealistically large cum shots. If that isn't your thi...

Women Enjoying Naked Men Ch. 03

by escriterra on Sep 13, 2017
Fetish

The muscles in her hips she had pressed into use as she fucked fantasy-Darrian the night before were actually sore the next morning as Taryn went through her gym routine. It was a delicious soreness. She looked forward to exercising those muscles so they wouldn't be sore. Taryn was ready. She just couldn't find a guy to peg. So it was good ol' dependab...

Cissy's Pegging Parlour

by Pinkmanties on Mar 18, 2020
Fetish

Fella's are you looking for a little backdoor action? Maybe you want those cheeks to feel the sting of a riding crop, or you want your boipussy filled with a firm supple dildo, or maybe you're just looking for a girl who will put your manclitty in a cage and tell you what a bad boy you've been! Come on down to Cissy's Pegging Parlour where your dreams become...

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.....

Pam's Shemale Experience Ch. 08

by majicman21 on Mar 11, 2019
Transgender & Crossdressers

Content warning: one scene with a golden shower... Pam woke with a start. It took her a few seconds to hear her alarm ringing. Next to her, Tanya was still asleep, and further down on the bed, Alex was as well, her head resting on Tanya's thigh. Pam reached over to the bedside table and quickly turned off the alarm. Neither of the other women stirred....

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...

Shemale Utopia

by Lewd_Ruby on Jun 15, 2016
Transsexual

*De-De-De-De-Deep* *De-De-De-De-Deep* *Click* I gently pressed the large red button atop my alarm clock to stop the annoying racket of those high pitched beeps. Sitting up I began to take a look around at my surroundings, Beige wallpaper spread across the walls, the odd video game poster stuck on lazily with some blu-tack. Letting out a small sigh I swung my...

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