Pegging Boyfriend Stories

56,080 results
Orientation
Length
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Infinite Scroll

White Women Got Big Dicks Too

by Samuelx on Sep 17, 2017
BDSM

My name is Susan Edgar. I'm a six-foot-tall, blonde-haired, green-eyed, forty-something Irishwoman living in Boston. I'm happily married to Stuart Lemond, a tall and good-looking, red-haired gentleman of French-Canadian descent. Lately, our relationship has been rocky. Partly because the passion is gone. So, we decided to spice things up. Bringing new people...

Bed and Breakfast Hotwife

by donaldelliott11 on Mar 9, 2020
Loving Wives

[Note: The hotwife in this story is, well, a wife, right? That means she has a husband. When she gets hot, he becomes a cuckold. You following this, Annony? Get over it, or read a different story. Oh, yeah, one more thing -- BTB is a fetish and has no place in Loving Wives.] *** Tracy and Don Elliott, empty-nesters in their late 40s, supplement their incom...

Learning to Let Go

by NRMathis on May 15, 2019
BDSM

Jonah could not remember a time when he was more nervous. Per his habit, he showed up far too early at the Cheesecake Factory, and was waiting at a table. For her. For the woman he had been chatting with online and exposing some of his deepest, most embarrassing fantasies to. The woman who wanted to meet him in person. The Domme who he wanted so badly....

Black Cuckoldress Tales

by Samuelx on Sep 13, 2017
Interracial Love

"I am a Black Cuckoldress, the type of Black woman who likes to take my man's big Black dick, put it in a chastity device and make him watch me fuck other men," I said to my reflection, and I smiled wickedly as I stood alone in the washroom. A tall, curvy young Black woman stared back at me. Clad in a red tank top, Black leather miniskirt and thigh-high Blac...

Mistress Whitney of Ottawa

by Samuelx on Oct 15, 2017
Interracial Love

"Samuel, you're a frigging waste of my time, I don't want anything to do with you, so lose my fucking number," Mistress Whitney, one of Ottawa's top professional dominants, screamed into the phone before hanging up. The curvy, caramel-hued biracial gal sat in the living room of her townhouse located near the Bayshore Mall in Ottawa, Mistress Whitney shook he...

Boston Guys for Ottawa Girls

by Samuelx on Sep 16, 2017
Interracial Love

Katharine Tremblay winced as Stephen Rothschild eased his cock out of her asshole. Never let it be said that anal sex is an easy thing to do. The tall young woman took a deep breath before rolling over on her side. Glancing at her boyfriend, she breathed a sigh of relief. The big and tall, dark-skinned young man she loved pulled her into his arms, and plante...

My First Pegging Experience

by doncamillo on Nov 19, 2018
Fetish

When I mentioned my interest in pegging to my professional dom friend her eyes sparkled. We were out drinking and have had quite a lot of drinks already. So it wasn't surprising that we ended up in her studio to satisfy my curiosity. After we got in she put her bag to the side, took off her jacket, helped me take mine off and stood in front of me. Looked u...

A late night at the office

by morpheus_arms on Aug 30, 2019
Miscellaneous

This is a Hub Page to make it easier to select a path the reader would enjoy most right from the start and as such very much a WIP. {Morpheus here: This story is what Germans call a "Fingerübung", a finger excercise to test out how to structure and maintain a first complex story all of my own. As such, expect some newbie mistakes and such, even tho...

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It's not All About Her

by Copycat88 on Sep 17, 2017
Fetish

DISCLAIMER: This story is about Femdom, Cross Dressing and Cuckoldry. If these topics offend you please don't read it... Just move on. No need to vote or comment if this isn't your "thing". If these appeal to you, please enjoy. ***** -IT'S NOT ALL ABOUT HER- I absolutely hate trying to get anything off of my husband's computer, but here I was trying and...

Tinder Pt. 02

by TwistedPanties on Jan 22, 2020
Transgender & Crossdressers

I appreciate you all asking me for more of the story - It would be hotter if you begged ;) Sissies can be so over-eager... (Keep the feedback coming please, Sweeties) Background: Bryan's roommate Caitlin has just discovered his crossdresser girl Tinder profile, while her friend Allison was swiping for a new girlfriend. Bryan is in the kitchen with a baby...