Shemale Pegging Stories

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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...

Sun, Sex, and a Summer of Love

by SolarRay on Sep 23, 2019
Exhibitionist & Voyeur

This is my entry for the 2019 Summer Lovin' contest. It is based on a collection of real-life incidents that have happened over the years either to me or things I've witnessed at both nude and non-nude events. It's also a little nod to this year's 50th anniversary of the first Woodstock festival in 1969. Enjoy! *** Kyle rushed through a maze of restless of...

A Perfect Life

by Wholemanz on Sep 19, 2017
Transsexuals & Crossdressers

DECLARATION: This story is an original literary work. I wrote a story just to stretch my creative muscles. All scientists and Wizards in this work are fictional. Any resemblance to anyone living, dead, or born in the future, is purely coincidental. WARNINGS: Contains transgender themes, Sci-Fi, explicit sex, mild violence, swearing, and strange ideas. It ha...

The Happiest Day of Her Life Ch. 12

by tangentjoker on Sep 16, 2017
Novels and Novellas

All of the characters in this work of fiction who engage in sex are above the age of 18. This chapter contains (in no particular order) elements of lesbian sex, group sex, gay male sex, voyeurism, pegging and bondage. Previously in this series, Marie Stevens Melar, an Emergency Department nurse, used her training to get through the traumatic experiences of...

Professional Excellence Ch. 11

by Touch_type on Jan 28, 2020
Exhibitionist & Voyeur

This one is long, but I hope you'll stick with it, it covers the action of Monique's cabaret-debut weekend. There are references throughout to earlier incidents about which I've written. I've put in a little context where relevant, but you can go back to the earlier tales if you want to find out more. You'll get more of the back story of other main character...

One Week In October

by ProtagorasII on Sep 14, 2017
Novels and Novellas

Part I Bloody Golf (FM+, MM) At thirty four I reckon I have weathered not too badly, at 5ft 6inches my 34-26-35 figure is fairly well proportioned, wavy auburn hair drapes over my shoulders and I am told I am "quite pretty" by those who would offer an opinion. OK I may not make page three anymore but my husband Andy reckons I am his dream girl. Married for...

The Fappening

by YKN4949 on Sep 25, 2017
Transsexuals & Crossdressers

Part I: The Data Breach I padded quietly down my stairs and crossed over into the kitchen. I felt the need to be absolutely silent for some reason even though I was, as usual, totally alone. Maybe it was something about the absolute silence of the early morning, with the crisp orange light pouring in through the window, that I didn't want to disturb. Maybe...