Bully Roommate Sissy Stories

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Infinite Scroll

Futanari World Transmigration Ch. 02

by Gregory8 on Feb 3, 2020
Transgender & Crossdressers

**Author's note: All characters in this story are over the age of eighteen. This story contains scenes of incest or incest content (Kind of but kind of not, as the person gets transported to another world so the people in it aren't really related to him.)** *** A dribble of jizz run down his chin, forming a small droplet that fell down to the ground. Antho...

Best Friends Forever Pt. 07

by Kantarii on Oct 24, 2018
Transgender & Crossdressers

"I want to have sex with you....." Brian's words echo over and over in my head as soon as they roll off his lips. Normally, guys tell me they want to fuck me, but he just made the moment a little more special. I might have wanted him to cum in my mouth earlier, but that's suddenly changed. Now - now I'm really, really horny and want him even more. As I gaz...

It All Started When...

by crashmatt on Oct 24, 2018
Transgender & Crossdressers

It all started when... well, perhaps that's not a great way to start. It's difficult to say exactly when it started, or perhaps even what "it" is. For the purposes of this story "it" relates to an episode at Halloween, yes I know, another Halloween story. But, you see, in the UK Halloween isn't the event that it is in the USA, and crossdressing for Halloween...

Craigslist Cocksucker Pt. 02: The Club

by putmeonmyknees on Jan 28, 2019
BDSM

The following story is part two of a series of group encounters that are loosely based on some experiences I had a few years ago with a man I met online. I had answered an ad in the 'Men Seeking Men' personals section: "Wanted: Submissive Cock Whore Willing to be used by Me and My Mates." This chapter continues my odyssey as I willingly service this man and...

Letter from Courtfield Common

by justincbenedict on Oct 21, 2019
BDSM

Dear Shoeblossom So the strangest thing happened to me recently. I am kind of a nerd, and I fix the bikes for friends of mine in a motorcycle club and I ride one myself, though possibly not as fast as they do! Recently I found out that one of my very tough, muscular friends had another interest in common with me...Scruffy was in chastity, and had a long-di...

Takeover!

by redwolf555 on Apr 23, 2019
Fetish

Brianna Wilson was feeling pretty good these days. Her marriage was in good shape, her husband Alan loved her very much and had a successful career. She was still a very pretty woman with a very good body. Her small cleaning company, Brianna's Cleaners, was doing very well. Her company primarily cleaned business offices but had recently begun offering Maid s...

My New Pet

by whisperingsubmission on Sep 14, 2020
BDSM

I've never had a pet before, at least not of the human variety, and had I been asked I would have claimed little interest in one. I suppose I should have known I was wrong, for I am certainly enjoying the delightful attentions of one at the moment... immensely. I adore my little slave boy, and how much he aches and whimpers for cum, and humiliation... anythi...

A Chance Encounter Ch. 03 - Some Excreted Evening

by fexhominum on Jul 15, 2020
Fetish

The motel was a seedy affair. Though the grizzled old desk clerk was friendly enough, offering me a flirty, "Here you go, sweety!" as he slid the room key across the counter and winked at me. Winked at me! Why? Because I was obviously some kind of kinky pervert on his way to be debauched by who knows how many men, or women, or ... or, maybe it was the outfit...

Naughty or Nice

by BigTittyHexManiac on Dec 23, 2019
Group Sex

Editor's note: this story contains scenes of incest or incest content. ***** Inspired by an online writing prompt. ====================================== The clock stroke midnight. Christmas morning officially began, and a young man by the name of Jason and his twin Mason officially reached eighteen years of life. But there was still time before the sun...

Bi Cuckold Humiliated and Fucked Ch. 03

by DaveLoveAss on Dec 16, 2019
Fetish

Part 3. If you haven't read the first one you should do that and learn how the cuckolding began. People keep asking for more so here it is, the second night... * Work that day was long and painful. Every step was a gentle reminder of the pounding Abe had given me the previous night. Every time I sat down was excruciating as my ass never seemed to fully clo...