Strapon Pegging Stories

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Pegging Suite

by rckplsky on Sep 13, 2017
Anal

They arrived in the order I told them to. Holly first. Zoey second. Riley third. We met in the bar/restaurant of the Hyatt. I had all ready set up the room earlier around check in time. That was at two it was now nearly eleven. I ensured all the amenities were there and that I closed the blinds. The room had a balcony, but I don't think we'd need it. Bu...

Cassi: Three is the Magic Number

by BoredWifeFantasies on Jun 8, 2020
Group Sex

This story involves some of the same characters as an earlier story, "Cassi Can't Resist". However, it is not necessary to read that story to enjoy this one! It also contains limited recounting of man on man oral sex as well as pegging, so if that's not your cup of tea this is your warning. Otherwise, ENJOY!! The rushing water felt amazing as it cascaded d...

Cissy's Pegging Parlour

by Pinkmanties on Mar 18, 2020
Fetish

Fella's are you looking for a little backdoor action? Maybe you want those cheeks to feel the sting of a riding crop, or you want your boipussy filled with a firm supple dildo, or maybe you're just looking for a girl who will put your manclitty in a cage and tell you what a bad boy you've been! Come on down to Cissy's Pegging Parlour where your dreams become...

Custom Incentive

by BacchanaliaoftheRedWolf on Sep 24, 2019
Sci-Fi & Fantasy

Petra grimaced. Another day of shopping, more of those fucking stares. She was sick of them, as she perused the skirts, the stockings, the things she found cute. Her flat chest tightened a little as she clenched her fists in anger, her jaw set. She couldn't afford to do more than this, but for christ's sake, it was almost 2020, and there were still clueless...

Make Me Your Plaything

by dlcalguy on Sep 25, 2017
Toys & Masturbation

I was in my early thirties when I had my first prostate exam. A visit to a new doctor and she (yes, she) told me that it was something men should do regularly once they reached my age. My friends and I had joked about prostate exams, as you do, and I was expecting the worst. But here's the thing. I didn't hate it. The doctor pulled on a rubber glove, cove...

Venus Trader

by skinnysailor on Oct 24, 2018
Transgender & Crossdressers

It's Oh Five Thirty aboard the seven hundred foot container ship 'Venus Trader' Twelve days out of New Orleans towards the Suez. It'll soon be time to get out of bed and fetch the Captain's breakfast. I'll lie in for a bit longer. I hear the door for the head open and close. I feel the bunk as Captain crawls in beside me. I pretend to be asleep. Our little m...

Stephanie McMahon The Boss Bitch

by DickThePimp on Aug 21, 2018
Celebrities & Fan Fiction

This is a parody... It is not real "Yes babe, I know it's important. I have it under control, don't worry. I will handle it. Don't worry, just enjoy England. I will handle this, I promise. I was just taking a shower. I've been so busy, I didn't have time to go home. The shower was messed up in the weight room. I got my workout in, but had to shower in my of...

Last Friday: First Sissy Experience

by sissysyzygy on Mar 5, 2018
Transsexuals & Crossdressers

Been a lurker for a little while, and thought it was time I contributed with a post! *** Title: Last Friday "You ready for your surprise?" she asked me coyly. "Yes!" I said excitedly, thinking of the possible toys we had been looking at online, or perhaps a striptease. We had our eye on a Bad Dragon dildo as our starter strapon kit had grown my interest...

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...

Interracial Pegging: Revenge

by Samuelx on Sep 11, 2017
Interracial Love

Bad company. That's what everybody says about me behind my back. And to be honest, I don't give a flying fuck. My name is Julianna McCain. A six-foot-tall, slender and athletic, red-haired and green-eyed young woman of English descent living in the City of Ottawa, Province of Ontario. And I am a Canadian porn star with a unique specialty. I am really into In...