Bully Roommate Sissy Stories

23,222 results
Orientation
Length
Source
Infinite Scroll

Don't Stereotype Cuckolds

by eviltwin52 on Apr 27, 2020
Loving Wives

Let me start by saying that I am a cuckold and a happy one. It was my choice and I found a Woman that would lead me down the path to unbridled satisfaction. Unfortunately too many Lit readers either disregard our lifestyle altogether or deride those of us who are strong enough to give our Women what they want and thereby meeting our own needs. But what are...

Wanderlust - Sabrina Pt. 05

by GeneraZ on May 11, 2020
Sci-Fi & Fantasy

5 - The Power Shift Paul's feet flexed painfully within the pink high heels. They weren't his, and they were much too small. With their lift he was exceeding six feet in height, causing him to loom over his beautiful blonde haired counterpart, but that did nothing to change the air of power she held over him. She giggled sinisterly as he, otherwise complete...

COVID-19 - Campus Closed

by puzziboi on May 12, 2020
Transgender & Crossdressers

"Momma, they're shutting down the campus on Friday," lamented the college junior. "I figured they would. I've been on the phone with Aunt Nettie. You can stay with her for the time being since she's close." "Doesn't she already have a ton of people living with her." "Patrick..I mean, Prisha," she swallowed hard. "There's just not a lot of options right no...

Be Careful What You Wish For

by ChainedToAKeyboard on May 12, 2020
Fetish

Author's note: This short story was inspired by Vitalis' amazing hentai artwork: "Bimbo Catalog: Bianca." * It was date night in the Whitley household and things were just starting to get exciting. Alice and Richard had enjoyed a lovely meal at a five star restaurant, a wonderful performance at the theater and a couple glasses of fine wine upon returning h...

Picked Up On the Prom

by DeborahC on Jul 15, 2020
Transgender & Crossdressers

I was nearing 20 years old and had no real life plan. At my Aunts suggestion, I accepted her invitation to use her coastal cabin. I was her favourite nephew and she thought I could make use of the solitude, the wide open space and the fresh sea air to gather my thoughts. The village near her cabin was a lovely old place. Set in a valley between rolling hil...

Bitch Trains A New Cum Slut

by dicktinie67 on Aug 17, 2020
BDSM

Bitch Trains A New Cum Slut -- Ch. 01 It was not as fun as I thought it was going to be. It started out great, but it did not end so well. My buddy, Mike and I were on a fishing trip in Maine and we met a couple of girls doing the same that were staying in the cabin next to us. I probably should give you some background on the friendship between Mike and...

I'm a Mess

by ClarasBestFriend on Oct 6, 2020
Loving Wives

Mike, my loving husband, had finally convinced me. Ever since we had gotten married, and even before then, he had been trying to convince me to fuck other men. "I want you to feel real pleasure!" "My little cock doesn't fill you nearly as much as you should be filled!" "I want to see you really get your brains fucked out!" I had heard things like this f...

Sissy Powers Ch. 01

by ClarasBestFriend on Sep 29, 2020
Sci-Fi & Fantasy

I smiled, looking at Clara resting her head on my chest, the way she usually does in the morning. But something felt different... Wait! Everything from earlier in the day came rushing back all at once, and I realized why these wake-up snuggles felt different: Clara's beautiful face was resting on my impressive bust! Clara laughed at feeling me jerk in sur...

Sexy Mandy Gets Her Just Desserts

by BAD BOY BILL on Sep 28, 2020
First Time

The day was fucking hot, Typical Southern California weather. I had been here a week and still wasn't used to the heat. San Francisco could get warm but not like this. Our saucy Mandy Collins had been the perfect host. Dinners, workouts, massages, and of course, fucking. Platinum haired Mandy had drained my ballsack several times a day for the last week. S...

Turning Tom

by DaddyAndrewG on Oct 6, 2020
Fetish

"She's sexy, isn't she?" I said to Tom, shifting my head towards Louise on the other sofa. Tom took a sip of the drink, clearly nervous at being invited over by this good-looking and clearly dark couple. Normally he wouldn't do something so bold, but lately he'd been feeling incredibly dissatisfied with his sex life, even though he'd be fucking a lot of wom...