Bully Roommate Sissy Stories

23,222 results
Orientation
Length
Source
Infinite Scroll

A New Person

by Reecer on Aug 18, 2017
Fetish

I thought stuff like this didn’t really happen. But I guess it does. I had been married for 7 years, and our sex life sucked. I guess it might have just been the seven year bitch, but we didn’t seem to agree on anything anymore. We only had sex on nights when she was horny, which actually was more often than one might expect. If I would go down on her that w...

House Bitch 01: Panty Slut

by gomez8 on Sep 13, 2017
Fetish

"Suck it, bitch! Suck it, you cunt!" Mistress was in fine form. She and Bec had just had a tussle. It had ended predictably, erotically. Mistress J had forced Bec to surrender and was now enjoying her well-earned delights with a 7-inch black strap-on. Bec's eyes were moist, her skin flushed from the contest, she glowed with heat and energy, and shined as she...

Time for a Kit Kat Ch. 03

by cashcrunch on Sep 17, 2017
Fetish

While kneeling there, before Kat's naked 20-year old body, memories of the summer of 2000 were flooding through Evan's head. Kat's older sister Sharon had been his lover the summer before he headed up to the big city to make a name for himself in corporate finance. Now, Kat had just caught him masturbating while reliving some of their torrid affairs. Worse s...

Alabama Nan: Good Time Granny

by SubLadyD on Sep 16, 2017
Transsexuals & Crossdressers

My first full year of college was over with and I found myself driving to my grandparents for the summer. The 'conversation' I had a day earlier with my folks was fresh in my mind... reminding me why I was making this drive. I could still hear my mother's condescending voice, "Nathan... NO your name is NOT Nancy! Your name YOUNG MAN is Nathan. I didn't car...

Winter Night

by rockhardy on Sep 16, 2017
Romance

The snow squeaks under my shoes as I step along the sidewalk leading to your door. I'm careful not to slip. My breath billows gray smoke in the night air. I check to make sure that I haven't forgotten my bag of goodies. It is too cold to come back to the car. Yes, all there, I assure myself. The bag is heavier than one would suspect. The contents swing with...

Caught Exploring

by SuprHap11 on Sep 12, 2017
Transsexuals & Crossdressers

I open the hotel room door and look around the room. The front room has a couch and table and the back room has two beds. A window in the front room looks out on the walkway and then past to the open atrium. I close the door and walk to the bedroom with my bag. I think again about the chat from last week and how exciting it was. I took the plunge and finall...

Becoming Missy

by hottiehunter on Sep 16, 2017
Transsexuals & Crossdressers

It all started back in 1973 in Seattle, Washington. I was 21, living on the south side with a couple of buddies while we were all stationed at area military bases. One Friday night we had a party at our apt. I was standing outside by my car smoking a joint when this guy pulls up in his pick-up. "Hey, how's it hangin?" he asked "Long and loose." I replied tr...

A Slut's Triangle Pt. 05

by Kantarii on Sep 19, 2017
Transsexuals & Crossdressers

It's 3:30 am. By the time I reach the I-85 southbound overpass, I'm an emotional wreck. Tears stream down my cheeks as I speed down the interstate, heading home from Atlanta. All I care about is getting as far away from Kryss as I can. Despite my enduring love for Kryss, those feelings are growing cold. Things really need to change for the better between us...

The Correction of Debbie Donovan Ch. 13

by RoryOmore on Sep 19, 2017
BDSM

Chapter 13: Hung DEBBIE "What are you waiting for girl? Strip!" Mrs Hammersmith demanded. "Can't you see everyone is waiting for you?" The gym at Silvermill wasn't like any gym I'd ever seen before. It was half the size of the one at my school, but instead of being dark and gloomy, it was bright and airy. Late afternoon sunlight came streaming through tal...

Fairy Tale Life Ch. 01

by petitelove on Sep 16, 2017
First Time

Breanna felt like the luckiest ex-secretary in the whole world. Staring at herself in the bathroom mirror, she just couldn't believe so many wonderful things were happening to her. A petite brunette in her early twenties, Breanna was wearing a very expensive white satin nightgown, cut low to show off the cleavage of her luscious high-riding tits. As she whi...