Strapon Pegging Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

I Want to Peg You

by pwlrstr on Sep 25, 2017
Fetish

I slip my hand around your waist and pull you into me, into a tight embrace. I'm wearing four inch heels, but you still stand a couple of inches taller than me, looking down into my gaze, an excited sparkle in your eyes. You run your hands through my hair, pushing it away from my face so you can see me better before coming in for a kiss. My hands run from yo...

International Pleasure Trip

by Escritor on Apr 29, 2025

Me, Sergio and her, Julia, have been a couple for six years now. I'm from Argentina, and after getting my college degree as an aerospace engineer, got contracted by a company in Phoenix. I'd lived there for five years until I met Julia, a simple girl from Sacramento, two years younger than me (I'm currently 35), that was in Phoenix in the middle of a nationw...

Reason? Nah.

by curdles on Nov 8, 2020
Bisexual

"Oh, fuck!" she gasped as soon as my cock had slid out of her throat. She had held it there for almost a full minute, massaging my balls with her tongue all the while. We hadn't seen each other for almost a week, so our appetites rivaled those of Erysichthon of Thessaly. "I'm almost there," I said, stroking my shaft. "Open up,"...

A Strapon Tale Pt. 02

by damn_thats_me on Mar 2, 2020
Fetish

All the events in this story really happened, only the names have been changed. Warning: contains themes of pegging, femdom, leather & latex, chastity play, and mild cuckolding. *** As mentioned in our last story Alex (29) and I (36) are both switches, and enjoy taking turns dominating each other. We had been dating for about a year now. Yet while we met...

A Strapon Tale Pt. 01

by damn_thats_me on Mar 2, 2020
Fetish

All the events in this story really happened, only the names have been changed. Warning: contains themes of pegging, femdom, leather & latex and chastity play. Alex (29) and I (36) had been seeing each other for about a year now. During our first date I immediately sensed that she had kinky potential. There was simply something about her looks and attitud...

Pegging With Lisa

by slutfreya on Sep 25, 2017
BDSM

Lisa and I have been swinging for a number of years and have always been pretty open with each other sexually. She is a beautiful, 42 year old bi, blonde standing 5'7" and a trim but shapely 135lbs. Her shaven pussy is absolutely sweet and she will squirt, usually when with other women or new male lovers. I'm Al, your average guy, 48, 6', 235lbs (working on...

Pegging Tales: Justin's First Time

by hfernandez1983 on Sep 13, 2017
Illustrated

*-*-* Pegging has been a topic that I have wanted to write about for a very long time. In my personal life, I have yet to do it. It has long been a fantasy that I felt has been left unfulfilled for a while. I have read a lot of stories on the topic and have loved most of what has been published on Literotica. So I thought it was time maybe I write a story o...

Sex Adventures with Alisha Ch. 01

by GeorgiaSexAdventurer on Mar 16, 2020
Erotic Couplings

WARNING: This story features a woman pegging a guy's ass with a strapon and the man eating his own cum. If neither of those two scenarios appeal to you, then you should consider reading another story. *** When I moved to my current town about six months ago, I knew no one. I moved here because I was recently divorced and desperate for a job. After almost a...

Pegging Surprise

by jane1179 on Sep 19, 2017
Fetish

Surprise pegging for my wonderful husband My hubby and I have been married for almost 5 years, No children yet, and we are both approaching 30 years old. We have been playing around with anal toys and a strap on for a little over a year now. I have a very rough and tough masculine husband, and never consider him a sissy in any way. Our pegging fun is stric...

Pegging Suite

by rckplsky on Sep 13, 2017
Anal

They arrived in the order I told them to. Holly first. Zoey second. Riley third. We met in the bar/restaurant of the Hyatt. I had all ready set up the room earlier around check in time. That was at two it was now nearly eleven. I ensured all the amenities were there and that I closed the blinds. The room had a balcony, but I don't think we'd need it. Bu...