Strapon Pegging Stories

2,794 results
Orientation
Length
Source
Infinite Scroll

Mistaken Identity

by grimbous on Sep 26, 2017
Miscellaneous

You step out of the office building onto the busy city street, the sidewalk is crowded with 9-to-5ers rushing to get home for the weekend. It is late afternoon and the heat of the day is just starting to abate. You see a woman who was on the panel in the job interview you just had rush past you to grab a cab. She must have been in the very next elevator afte...

Open in Reader

Boy with the Butt Pt. 03

by HornetNest471 on Jan 28, 2020
Fetish

*Knock! Knock!* I can't stand my fucking mom. Was it too much to yell at my girlfriend and kick her out of the house when she found us? My answer would lean towards yes. Did she take it a little too far when spanked and verbally degraded me? Definitely. But now, even she might be doing too much. The door in front of me swung open slowly as the head of a...

Sami

by Tricker126 on May 5, 2018
Fetish

You've known her for years. A blonde-haired, brown-eyed girl who always had the energy to for just about anything. As far as you know, she's just an ordinary girl doing ordinary things. Studying macroeconomics at an expensive college you couldn't afford (Her parents were both lawyers), she left just after you told her how much you were into her at the airpor...

Open in Reader

AC: lost in the animus

by Damos on May 17, 2019
Fantasy

“David; nice of you to come!” a voice spoke and looking over there I saw the dark haired woman standing there greeting me, “This is the team, Lucy!” I looked over and seeing the blonde nervous woman she whispered, “Hi!” I looked over to Rebecca who whispered, “She fancied a man who died saving the world!” I nodded before saying, “Desmond!” she nodded before...

Open in Reader

The Big White Trash Bang Theory Ch. 01

by DickThePimp on Jan 22, 2019
Celebrities & Fan Fiction

A Big White Trash Fucked Up Fuck Parody Motherfuckers!! WARNING: DEPRAVED OFFENSIVE AND FUCKED UP TO THE MAX... READ AT YOUR OWN RISK My stars and stripes, super charged van is careening out of control... about 165 mph... down the PCH (Pacific Coast Highway). I'm late for a meeting with my agent... Basketball Wives LA star Jackie Christie. I brought along...

My White Trash Life Motherfucker Ch. 01

by DickThePimp on Jan 15, 2019
Celebrities & Fan Fiction

Fucked up fuck parody series alert WARNING : The most offensive and depraved fuck parody series ever written... Read at your own risk... If you're not offended then you're one of my fans motherfucker... I approved this fucking message... Read on motherfuckers... This series replaces the White Trash For Life series... Pussy + Moonshine = Life... FUCK YEA...

A Submissive Mind Ch. 03

by raytrace34 on Sep 15, 2017
BDSM

Preface. This is the final chapter of the story. While I hope you will enjoy it, I would recommend starting with the previous chapters, as some events here won't make any sense otherwise. Alex tried to forget Anya and Natasha. He still had some good memories of what happened, but he felt Anya was pushing him too hard. He got a girlfriend. She was just...

Variation

by Genas on Sep 1, 2017
Group Sex

(Note to readers - This is a true story and is co-authored by me and Linda1234, another Literotica author. I am posting it here with Linda's full knowledge and consent. Only the names have been changed to protect the privacy of the subjects.) * My name is Katie. I'm in my 40's, a Sara Evans lookalike, 5'6" 115 lbs, C cup, and very Bi. In fact, I'd be a le...

Pegging Parker

by Purple_Parli on Sep 12, 2017
Transsexuals & Crossdressers

Parker answered his phone with his usual, "Yo." "Do you even look to see who's calling when you answer?" Jamie's voice said. "Not usually." Parker admitted. "Why?" "I'd think that when I called, at least, I'd get something a little more romantic than, 'Yo'." He could tell she was just fucking with him, trying to poke him a little to see if he'd respond,...

Mike and Chris Together

by Boxlicker101 on Sep 15, 2017
Transsexuals & Crossdressers

NOTE: This is my entry in the 2012 Literotica Valentine's Day Contest, and it is about a man having sex with a male to female transsexual. They basically take turns fucking each other in the ass. If this kind of activity bothers you, you should probably stop reading this story now. * Mike's sex life had taken a definite series of turns for the worse. When...