Prolapse Gaping Stories

22,937 results
Orientation
Length
Source
Infinite Scroll

First Time I Fucked as a Girl

by ambercumz on Mar 5, 2018
Transsexuals & Crossdressers

I just wanted to say this is a real story that really happened to me. * It was the summer after graduation and I had just turned 19. I was dating this beautiful brunette girl. I liked her a lot! One reason, was she was very bisexual and I loved watching her have sex w/other girls. Plus, we both had a little bit of a "kink side" to us. She introduced me to...

Jack and Jill Pt. 06: Jean

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

They had been trying for a baby for some time and had come to the sad realisation that it wasn't going to happen without some intervention. The doctors wanted them to use donated sperm and have insemination, but it seemed so clinical. Jean had told them about a breeding club that she had worked in and they both liked the sound of it, but as she was walking t...

Shannon's Submission Ch. 02

by alexanderdevalley on Sep 16, 2017
BDSM

Chapter 2: Shannon's The Party The knocks on the door crashed in Shannon's ears like a pounding bass drum, her heart beat quickening, her pulse racing, thumping in her ears. A slight feeling of embarrassment, anxiety and arousal falls over Shannon, knowing she is bound spread wide for the visitors eyes, her ass filled with the short, fat jelly butt plug, th...

Inny-Mini Penis Won't Come Out

by billyrobey on Sep 17, 2017
Fetish

I wasn't super overweight, but most of my fat was in my middle. At the time I was in denial about my manboobs. I guess I was just avoiding the whole thing as I quickly became kinda fat. I hadn't jerked off in what seemed like months. I was kinda uncomfortable with the walls, floor and ceiling being so thin as far as sound was concerned. Having a kinda short...

Vanessa and I - Ch 17: Exploring

by TEBJrNghwJqw on Nov 26, 2018
Loving Wives

I returned home from a business trip two days early, but didn't tell V. I wanted to surprise her. I'd been away for almost two weeks, and all I could think about was fucking her. Parking my car quietly, I entered the house, but no sign of V. Not surprising - it's sunny outside, so she is probably tanning. I grab a beer from the fridge, take a deep pull, and...

Julissa Takes Big Cocks

by Robertshotwife on Sep 19, 2017
Loving Wives

Over the past two years, Julissa and I had engaged in her fantasies, our fantasies, her fuck-buddies' fantasies and encounters with several strangers. While fooling around one night, my wife asked me what she could do for me for my 45th birthday. I told her she had entertained most of my fantasies already; however, I had always dreamed of watching her being...

Fucktoys for Futanari

by RedragonLite on Jun 28, 2020
BDSM

Join the CHYOA Fan Server and discuss this story and many more with the community: https://discord.gg/DQn3bVH If you want to support me and my work, please check out my Patreon: https://www.patreon.com/redragonlite Reality has changed, and the third sex: Futanari (Or Futa) are considered the most respected members of society. Futas can do almost anything t...

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Brianna's Surprise Ch. 03

by TX_Dude_ on Sep 14, 2017
Group Sex

Brianna and Howard had settled into a very comfortable and frequently adventurous relationship. They had established two very structured dynamics but, they frequently bled into one another. Brianna was always in charge, even if on the surface, for the benefit of other family, it appeared as though Howard was the authoritative father figure. In reality, Howar...

The Nasty Slut Ch. 01

by theprince on Sep 19, 2017
Fetish

Prince and Jenna were on a holiday. They were in Acapulco, in the Presidential Villa in the Villas of Acapulco. Both knew they were going to need all the space and luxury for a dirty, kinky, nasty fuck session that they were going to have. Plus they had the company of Lola. Lola is the nastiest slut in Acapulco. They had hired her services for the vacation...

Slut - The Model Returns Pt. 03

by NeilMc123 on Aug 13, 2018
Exhibitionist & Voyeur

I lay on the makeshift bed, sprawled out wearing my sexy lingerie, with my right hand between my wide open stockinged legs, gently stoking my shaved pussy. I'd Just swallowed Neil's, his brother Tom's and my husbands orgasmic fruits. Neil and Tom were setting up lights and cameras over the other side of the studio as my husband looked lovingly toward me, sti...