Pegging Surprise Stories

136,140 results
Orientation
Length
Source
Infinite Scroll

You and your Girlfriend's Wonderful Night

by EugPad21 on Nov 28, 2020
Fetish

You walked out of work. Relieved another working week had finished. It was Friday. However, this was no ordinary Friday. Today was your 1 year anniversary with Elle. Elle was your wonderful girlfriend. You had met at a bar. You saw her from across the room. She wasn't hard to miss. Bright neon blue hair. She was curvy too. An incredible ass complimented her...

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The Seven Dressing Sins: Vanity

by purekink on Jul 15, 2020
Transgender & Crossdressers

"To recreate this scene, you will need..." John tightened his calf muscles as he watched the young woman on the TV present an untidy scrap of cloth. "One white fishnet dress." He thought he knew her, somehow - something in her voice perhaps. He didn't know anybody with a crimson streak through her long blonde hair. And he certainly didn't know anybody who...

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...

Tease, Party, Peg

by magmacdowel on Sep 11, 2017
Anal

Lynn was examining herself in the standing mirror when her shirtless husband, James, entered the bedroom. His olive-tan skin was still beaded with steam from his shower. She looked back at her dress. It was a teal and coral printed sheath that hugged her curves, even with the back unzipped. "Someone looks nice," James said as he came up behind her and place...

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...

Pequeñas y Humillantes Historias

by 57 on Jun 7, 2020
Miscellaneous

Primero que nada me presento. Soy Guillermo, y tengo 25 años de edad. Además, como descubrirán en las historias que les voy a contar a continuación, tengo el pene pequeño. 10 cm flácido, 12 cm erecto. Es así. Ya lo acepté. Que lo haya aceptado, no quiere decir que no me avergüenza el hecho de ser objeto de burlas por parte de otras personas. Pero creo que ha...

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Your Adventures in Mixed Wrestling

by EugPad21 on Nov 20, 2020
Fetish

You walk through the doors. Excited to begin your first day as part of the Mixed Wrestling Federation. You walk up to the desk where a receptionist is waiting for you. "Hello, How can I help?" She asks "Hi my name is (Insert your name). I'm here for to sign up for the Mixed Wrestling Federation" "Ahhh yes" she said, "We got...

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Bdsm adventures

by Sgtwolf on Dec 7, 2017
BDSM

This story is for a compilation of many different bdsm adventures. It was formerly known as latex adventures, but as chapters developed they dealt more and more with different aspects of bdsm, and less consistently with latex. Latex still exists as a strong element in many of the chapters, namely because I like to write about characters wearing it. I created...

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Pegging Fantasies

by the_shires on Sep 25, 2017
Fetish

Alan looked over at Jill. As usual her face was buried deep in a stack of books. Not one book, or even two. At least four. She was studying for her exams, and her face showed intense concentration. He sighed. They had a matter of weeks left before they were out of college and working full-time jobs. There was a lot of anxiety written around them and he knew...

Somali Queen In Ottawa Ch. 05

by Samuelx on Sep 12, 2017
Fetish

The things I do for love never cease to amaze me, ladies and gentlemen. The other day, after a night of passion, I tossed my girlfriend Yasmin Hussein my house keys, mainly because I wanted more access to her pussy, and the sexy Somali chick got it into her Hijab-wrapped head that I wanted her to move in with me. I was terrified of Yasmin moving in with me b...