Squirting Boypussy Stories

16,370 results
Orientation
Length
Source
Infinite Scroll

Mistress Jaz's Sissy Slut

by barbiboi on Aug 30, 2017
Fetish

Mistress Jaz had invited me over to give her a pedicure and provide sissy maid service. What I got was a mind blowing day of servitude I will never forget! I arrived in the morning and was greeted by a vision of beauty. I had seen pictured of Mistress Jaz before, but they paled in comparison to meeting this incredible Goddess in the flesh. Tall, curvy, wit...

Greta Fights Mommy Adriana

by Gretatv on Sep 16, 2017
Transsexuals & Crossdressers

Dear Readers, this is the second part of the Mommy Adriana series. I hope you enjoy the ride, there is more to come. * * * * * Mommy Adriana continued her assault on my boycunt with her 10 inch strap-on dildo stretching me to the hilt. Meanwhile Andrea, my wife, had gotten up from my face, leaving me drenched in her juices. She sat exhausted on the couch...

Being Jenny's Summer Boyfriend Ch. 03

by Lucas96 on Jan 21, 2020
Fetish

Disclaimer: this story involves cuckolding, humiliation, cross-dressing, and gay incest. *** I have to admit, it was difficult to contain my excitement as Jenny invited my dad and brother over to show them what a little sissy slut I'd become. To prepare, Jenny let me try on the outfit she'd had on when we'd come over to Andrew's house: a pink, tight-fitt...

Intergalactic Sexy Scientist Ch. 02

by MythMaker on Sep 11, 2017
NonHuman

(Special thanks to JohnnyRottencrotch for suggesting the scenario for this story.) This time last year, an archaeologist and her assistant arrived in the Chihuahuan Desert from the UK to research ancient Native American sites. For whatever reason, that assistant had returned. David rented a cheap, beat-up car and drove for what seemed like hours to the...

Serving the Dark Lady Ch. 02

by Certeis on Mar 5, 2018
Sci-Fi & Fantasy

NOTE: So halfway through writing this, I sort of realized that the way I've been pronouncing 'Aasi' as a shortform of Aasimar actually sounds close to sissy. Intentional? Who knows! ***** Lan took Karee... to the same pub he'd been at last night? It was noon so it was pretty much empty, but the bartender was still there. "You gonna keep him outta trouble...

Elizabeth: Beginnings of a Sissy

by ElizabethJessica on Sep 16, 2017
Transsexuals & Crossdressers

I had a pretty good system going. My 18 year old sister would stay up to watch Sex And The City reruns with me (well she watched, and I smoked weed), and during the first ad breaks, would run downstairs and get changed for bed. During the next ads, I would go to the bathroom, and on my way, raid her hamper for her fresh dirty panties, usually buried under th...

Neighbors Sissy Son Ch. 04

by newfield1981 on Apr 3, 2018
Transsexuals & Crossdressers

Authors note: All characters are 18 and older. This is a stroke story about a transgender boy as he transitions into a girl and the mischief she gets into along the way. It's not meant to be a "how to". It's strictly fantasy. I hope you enjoy and cum lots! ***** It's been three months since that fateful day Tiffany's mother Carol became aware her son was...

Two Hot Blondes Get Burgled Ch. 07

by scatwoman on Jun 15, 2020
Interracial Love

Chapter 7: "Repercussions" "SMACK!" "RRGH!!" "SMACK!" "MRRGLFM!" "SMACK!" "CRFFT!" "Heh, whatsa matter whiteboy?" Donk chuckled as he stood behind Todd and alternated slapping the left and right side of the bound quarterback's face with his flaccid 20-inch dick, "doncha like big black dick as much as yo girl over there?! I thought ALL white bitches lo...

Me And My Online Master

by ftpmike1980 on Sep 16, 2017
Letters & Transcripts

This was a chat with my master. Online Master: Hello, lad. Hope you are being a good boy, Michael. Michael: I am doing well. Hope you are doing well. Online Master: Glad to hear you are doing well, Michael. I am also. Let me know when you are ready to play again on cam, lad Michael: ok. sorry we haven't been able to meet up online. i've been busy with...

A Great Recession Ch. 02

by GreaserBob on Sep 25, 2017
BDSM

A Great Recession: The 1st Pegging This is the second part of what I plan to be a short series of several stories. Part one is a briefer introduction of Laura and Rob the central characters, a married couple exploring BDSM, power exchange, femdom and male submission. Some weeks later, I found myself in the parking lot outside an adult gift shop thinking ab...