Pegging Surprise Stories

1,000 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com

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...

Black on Black Pegging : Surprise!

by Samuelx on Sep 11, 2017
Erotic Couplings

Guys, don't you just hate it when your woman walks in on you while you're watching porn? It's happened to all of us at least once. And recently it happened to me. Actually, that embarrassing episode turned out to be the best thing that ever happened to my girlfriend and me. No, seriously. I mean that. My name is Thierry Jean-Guillaume. My friends call me T.J...

Surprise Pegging

by SlutProblems on Aug 7, 2019
Group Sex

"Put this on," I told Toby. I smiled wickedly at him to let him know that what I had planned was going to be something special. I'd been working on this for the months leading up to his birthday. I'd scoured sex sites and watched porn to get ideas. He had no idea what I was up to but if I had my way, he was going to have a birthday he wouldn't soon forget....

My Little Ventrue Pt. 06 Ch. 03

by NovusAnimus on Jul 13, 2020
NonHuman

~~Antoinette~~ She combed her hair over chest, and sighed. She was still dressed in the suit she wore, though she had dismissed the jacket, more comfortable in the white shirt and gray skirt. Sitting with one leg resting upon the other at the knee, she leaned back upon the couch in one of the many lounge rooms of her Elysium tower, and looked up at the ceil...

A Femme Domme Tale Ch. 02

by melanieatplay on Sep 25, 2017
BDSM

I awoke the next morning to the smell of bacon and freshly brewed coffee. Is Chris cooking? I looked over at the bedside clock, I had slept until just a little past noon. Slowly, as I begin to wake up in earnest, the previous evening's activities flooded into my mind. The restraints, my dominatrix outfit, our extreme facesitting session, and Chris licking...

A Big Surprise!

by rj1774 on Jul 6, 2020
Transgender & Crossdressers

As a man's sexual desires come to light this story features, femdom, pegging, crossdressing, and dating a TS woman. Please share any constructive criticism or where to take a next chapter. I hope you enjoy! **************** My sweet, caring, brilliant girlfriend, Stephanie, and I have been dating for a few months and we decided to plan a long weekend get a...

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...

Birthday Surprise

by HighPlainsDrifter on Sep 14, 2017
Erotic Couplings

We were both headed out the door to face the day. "Don't forget, dinner is at 7. I have something special planned for you. I think this will be a birthday you won't forget, " she said, flashing that huge sparkling smile. I thought about her comment several times as I worked through the day. I texted her once asking her to give me a hint. Her only reply was...

Lottery Surprise

by legsfeettoes on Feb 13, 2018
Fetish

I'm still not sure this really happened. All my school debts and expenses have been paid. My tuition, my books, all my supplies, my living expenses - food, clothing, medical insurance, vacations, etc., etc., etc. are all taken care of! When I complete grad school, I will be debt-free. I will have the money to buy a home wherever I settle. And I didn't win th...

The Best Present: Pegging my Man

by silkstockingslover on Sep 25, 2017
Fetish

Summary: A wife discovers her husband is curious about pegging and.... Note 1: This is a Holiday 2016 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, Dave and goamz86 for editing this story. The Best Present Ever: Pegging my Man I was working from home, stuck with a sick child, when my whole world changed. My work laptop died and...