Pegging Stories

1,124 results
Orientation
Length
Source
Infinite Scroll

A Lost Lover, Changes for Melissa Pt. 01-02

by MadQuill on Feb 6, 2018
Transsexuals & Crossdressers

Please remember this is a copyrighted work and all legal disclaimers apply. I appreciate the editing assistance of Santacruzman. There is an inspiration for this tale and the character Thom in the film directed by Jean Negulesco: "How to Marry a Millionaire". I love the three women characters, Shatze, Pola and Loco and their manipulations. This tale does NO...

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...

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,...

Preacher in Her Garden

by Handymanblues on Dec 23, 2019
Loving Wives

(Of all the true stories, sweet romances, diaries, manuscripts or documented words of love and passion I have ever written, this is my favorite of all time. Read it and you'll know why. It's just so darn touching. You just know some women are going to make perfect loving wives. But if you're a man, the trick is to find one for yourself.) The early morning...

Nan Gets a Threeway Ch. 03 - Finale

by Valendon on Jul 3, 2018
Group Sex

Here's the finale' of the "Nan Gets a Three-Way" series! There's some adult incest mixed in, so if that bothers you, this might be one to skip. I hope, gentle readers, that you've enjoyed the stories. This is my last one; I don't intend to write any more. I began writing erotica as a sort of self-designed therapy after losing a life-long friend and lover...