Strapon Pegging Stories

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Women Enjoying Naked Men Ch. 03

by escriterra on Sep 13, 2017
Fetish

The muscles in her hips she had pressed into use as she fucked fantasy-Darrian the night before were actually sore the next morning as Taryn went through her gym routine. It was a delicious soreness. She looked forward to exercising those muscles so they wouldn't be sore. Taryn was ready. She just couldn't find a guy to peg. So it was good ol' dependab...

A Wedding Night Pegging

by pwlrstr on Sep 12, 2017
Fetish

"It would be more of a big deal if it was the first time," Jon had said, instantly regretting that it sounded a bit negative, when his fiancée Naomi had asked if he was looking forward to their wedding night. "I mean, I don't really believe in saving yourself for marriage or any of that crap. I think it's definitely been a good idea to have lots of sex first...

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...

Sissified by My Sister

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

I will never forget that night. The night I discovered how I truly am. My true self. Its an unforgivable night. And I never thought my little sister would be the one to help uncover this part of me. I was a young, average 19 year old, my sister and I were home from college for winter break. I had short, blond hair and my sister had brown hair cut about at h...

Sissyhood of Travelling Panties Ch. 01

by daddyslittlebitch on Sep 14, 2017
Transsexuals & Crossdressers

Chapter 1: Alex A pair of red satin panties lay on the bed. They were boyshort style with little red lace bows above the crotch. Very sexy and very slutty. Helen ran her fingers along the soft, smooth material. She was dressed in a black lace garter belt holding up thigh high stockings, her large, round breasts, still firm at the age of 45, stood out naked...

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,"...

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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...

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...

Keeping an Open Mind

by Templar_Writer on Nov 4, 2019
Fetish

Not much to say about this one, just an idea I have been meaning to get to. "Okay, now I'm asking you to keep an open mind." Having just finished a great meal cooked by my girlfriend, Seema, for our anniversary, I was in a good mood. However whenever she asked me to "keep an open mind", it didn't mean the same thing other people mean. When she uses that phr...

Careful What You Wish For Pt. 04

by Switch90 on Sep 25, 2017
BDSM

Shane laid in bed, completely exhausted from hours of endless teasing. Michelle had iced down his cock, still barely being able to contain it in chastity. "I'm sorry that you made me lock you up slave. I was really enjoying using My cock." "Please. Please unlock me. Please use me some more. Please let me fuck you! You're driving me crazy!" "I know." Sh...