Strap On Pegging Stories

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Orientation
Length
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Infinite Scroll

Julia Milks Her Colleague Ch. 02

by JohntheRapturist on Apr 23, 2018
Fetish

Julia pulled out her toolbox, grinning as it rattled across the floor. It was a huge, heavy thing, bound in faux black leather with satin nickel struts and latches. She fished out a small, heart-shaped key. The lock came open with a snicking sound. Julia was all legs and curves, a red headed and green-eyed vision of Amazonian paradise. Tommy, if he'd known...

Service with a Smile

by psychoskunk on Nov 26, 2018
BDSM

Sixty nine minutes ago, Katie, my live-in slave, got on her knees and asked for permission to go to the store and get a few things for breakfast tomorrow. With thoughts of the evening already drifting through my head, I allowed her one hour to go to the Whole Foods. Katie promised me that she'd be back, the market being less than a mile up the road (and only...

He Knows Pt. 02

by agens_minaci on Oct 14, 2017
Anal

This is part two of a fictional story and not intended to suggest anything about real-life BDSM play, consent, or relationships. I welcome your comments and suggestions for this story. Thank you. ***** When I awoke the next morning, Matthew had already left for work. He had left a note for me. "At 2 pm, go to the bathroom and slide this plug into your as...

Kyttn's Gift

by riley_oneill on Sep 17, 2017
BDSM

You'd left a gift for me. Opening it, my fingers trembled ever so slightly. The package held a plain leather collar, one I'd had for a long time. A shiny new red tag in the shape of a heart engraved with the word "Kyttn" dangling from the front. I finger the tag and smile, then run my fingers over the well-worn leather before putting the collar on. The tag...

The Dangers of Thinking

by RemiMarselis on Sep 1, 2017
Humor & Satire

"Is this as awkward for you, as it is for me?" I hope that by shooting the elephant in the room, we'd have a little space to breathe. Horton's internet dating stories never mentioned uncomfortable moments like this. They always started with him being a douche, doing something stupid, and fucking an overweight chick with big knockers. I shoot a glance at Tam...

A Cheating Wife's Disclosures Ch. 03

by Krystal0690 on Sep 12, 2017
Loving Wives

It was 9 PM on a cold Tuesday night and I was sitting at a bar on the other side of town. I had a date set up with a married man I'd first met online. It wasn't really so much a date, as it was a quick get together for sex. We've had sex twice before and most likely this will be our last encounter. I was no longer looking for a relationship or an emotional c...

Aphora's Mission Ch. 12

by ValoryG on Sep 15, 2017
Transsexuals & Crossdressers

My liaison with N-dasha (and Will's experience with his woman) raised our confidence levels immeasurably. It also seemed to raise our general horniness. Will continued to sleep with me when Na-hoyan was away. I must admit that (even though I keep using Will's male name here) I had begun to see "her" as a woman. Her femininity had blossomed as well as her a...

Neighbors Delight Ch. 06

by gummidurango60 on Apr 17, 2019
Transgender & Crossdressers

We crossed the street hand in hand laughing at the night's scenario. Aaron opened the front door for me and I rushed to the bedroom to prepare myself for what was to happen next. I slipped on my wedding ring from my purse, retrieved the lube from the nightstand, squatted, pulled my panties to the side, inserted the tube into my pussy and squeezed hard; prepa...

Volunteer Jenny Helps the Circus Ch. 2

by Capstick on Sep 15, 2017
Loving Wives

"Quick dear, let's get you out of that costume!" said Sonya, as she took hold of Jenny's hand. Many of the performers had gathered around the backstage area to watch her performance, and gave her a nice hand as they scurried back to her changing room. Jenny felt several pats on her rump, as she passed quickly down the narrow walkway! "This is NOT what I had...

Mark and Mary Ch. 03

by tower1604 on Feb 6, 2018
Group Sex

Mark got comfortable in the chair as the 2 young women started to undress Gloria. Zoe and Claire pushed Gloria back onto the settee directly opposite Marks chair, giving him a grandstand view of the action. Zoe removed Gloria's blouse exposing her creamy white flesh and black and white pantie set. Mark had, had sex with Gloria twice, the first, after beatin...