Pegging Crossdressing Stories

2,183 results
Orientation
Length
Source
Infinite Scroll

Born to Be Ch. 02

by DamienDeath20 on Apr 23, 2019
Transgender & Crossdressers

A.N. A CHAPTAH TWOOOOO Fun times up ahead :3 the world has been kicking my ass with trying to keep up with my projects, but I'm powering through as best I can. The Following Contains: Femboy with tall black babe fucking him up the butt with a strap-on. *cries it's not futa* Lol, also in this chapter, we begin the process of feminizing our pretty protagon...

A T-Girl and a Tomboy Pt. 03

by AlexBailey on Sep 14, 2020
Transgender & Crossdressers

A Surfer and a Swimsuit Model _____________ Hello! This is part three of a full length novel in four parts. It's a gender-fluid, 'what if everything fell into place,' fantasy about self-discovery, coming out and coming of age. It explores pansexuality, cross-dressing and several fetishes - especially for things like swimsuits and athletic-wear. Some part...

Bought Ch. 02

by Jeremydcp on Jan 21, 2020
Group Sex

Chapter 2. "First" "When I was younger, I liked these to be slightly toasted, but now that I'm older, I like 'em... charred." "You obviously have a thing for flaming balls." Bella's laughter, sweet and melodious as it was to Jason's appreciative ears, filled the late morning air all around them. A rare, precious gem, his bride was brimming with spirit - u...

Freaky Fuckday

by GayTripper on Sep 18, 2017
Sci-Fi & Fantasy

This is a bodyswap story with a twist. The erotica in this tale focuses exclusively on straight sex (a rarity for my works, I know) though there are homosexual elements to the story because of how the plot develops. If you're looking for an instant erotica fix, this probably isn't the story for you but I guarantee it pays off eventually. This is my first ent...

From Stubble to Foundation

by tre34harr on Sep 16, 2017
Transsexuals & Crossdressers

This is a story about a guy who can only love with someone if he changes them from a guy to a girl... in time the guy he takes goes through the changes and welcomes the end outcome. If there is anything you don't like about crossdressing and sex changes this isn't the story for you, but if it is read on and have your eyes opened wide. ***** "I hold my han...

A Sea of Heartache

by drnosty on May 11, 2020
Novels and Novellas

"Conrad, have you seen or heard from the Doc lately?" "Not in a couple of days. The last I heard; he was out at the Colony. One of the rich and famous probably got a hangnail or something." "Come on. You know he doesn't cater to the rich and famous. We're damn lucky to have him. Any man who gives up on the world and dedicates himself to helping isolated...

Mistress Maggie

by Joscelyn2tg on Sep 15, 2017
Transsexuals & Crossdressers

My Dear Reader, Welcome to a most unorthodox love story. A story containing romance, transgenderism, spirituality and yes, even S&M. But first allow me to ask you a question, and when you reach the end of this story, it will make much more sense to you. If your soul returned in the body of someone else after you died. And you were allowed to whisper one th...

Altered Ch. 07

by MaximusTheMad on Jul 4, 2018
Sci-Fi & Fantasy

*All character engaged in sexual activity are over the age of 18, in case it's not obvious or mentioned. *This chapter has no sex scenes in it. Don't be too disappointed, there will be chapters that will have too much sex in them and everything will balance out. *This is a long story intended to span many chapters, please go back and read the previous chap...

The Making of a Man Ch. 01

by Imakewetspots on Feb 10, 2020
Mature

(Author's Note - First, a special thanks to Literotica author "Cockhole" for his help. I have a mental outline of potential future stories branching off this first piece, each developing characters more fully as the overall storyline progresses. Please feel free to message me, privately or publicly, any constructive criticism, opinions, or ideas to incorpor...

What's the Worst That could Happen

by Ky_Da993 on Jun 11, 2019
Loving Wives

Quinton The reason people live in southern California is for the weather. Few places in the world can offer the perfect temperature on an early evening in middle of winter. Not too hot, nor humid, just perfect. This perfect night, I followed my wife up the dozen stairs to the front door of an outrageously expensive and opulent home. The house was amazing,...