Strapon Pegging Stories

2,794 results
Orientation
Length
Source
Infinite Scroll

Dry, No Lube

by Voboy on May 30, 2018
Sci-Fi & Fantasy

This was fun! Thanks to PuckIt for spearheading this little dip of the toes into an old love of mine, SciFi. I suppose, in keeping with my usual practice, that Lieutenant Pixy Pfeiffer would be a many-times-removed granddaughter of Chad Pfeiffer and Ashley Gallo, if such things are important to you; she's certainly got the bewitching Ashley's bold eyes. I'...

My Niece and Her Friends

by rmdexter on Sep 13, 2017
Novels and Novellas

Note: This is NOT a new story. I have broken up the story previously published as "My Niece and I Go on Vacation" into two parts. This is the first part, prior to the vacation actually starting. * As I left my brother's place, pressed on the accelerator and headed back towards my own place, I pulled out my cell phone and called Tanya's number. She answered...

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...

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...