Chastity Roomate Stories

6,938 results
Orientation
Length
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Infinite Scroll

First Time Chatlog

by Maddirose on Sep 15, 2017
Letters & Transcripts

by Maddirose (edited by the impervious DeReve) -------------------------------------------- Did you love this story? Hate it? Could it improve? Please let me know in the comments, or via the CONTACT tab on my profile. -------------------------------------------- imasweetieXX: Hello there browncoatXXXX: hi! imasweetieXX: I'm not really sure what to typ...

I Came Home Early & Came Ch. 02

by Curtain on Sep 15, 2017
Loving Wives

When I came home the next day, the first thing on my mind was whether Sharon would mention her dalliance with Lisa. She was all hugs and kisses when I got home but made no mention that day nor the next about our beautiful, young neighbor. I said nothing of what I saw, and went about work and home with nothing more than a heightened sense of observation. Ne...

Craigslist Adventures 04

by PorscheKaru on May 13, 2020
Transgender & Crossdressers

Before I tell more of my stories from the past I'm going to update you on what's going on with me most recently. The girlfriend I have been living with has left me and moved to another state. So despite the hurt I figured the best thing to do was to order gurly stuff and start dressing again. But before that, while still together with my girlfriend, she...

Cum Party

by 15inches on Sep 25, 2017
Group Sex

My name is Chris and I had to share an experience I had with 3 of the sexiest and sluttiest girls that I met through my College roomate. Before I get into the details though I should tell the readers a bit about myself. I am 18 years of age, I have light brown hair and blue eyes, 6-2 205 pounds with a well toned body that is almost completely hairless. Altho...

Tabby's Friendly Roomate

by Tabby18lover on Sep 16, 2017
Group Sex

Angela and I roomed together from the beginning of that first year at college. Two 18 year olds away from parents and both of us remote from our original communities. For me the experience was a great adventure, a whole new world to explore and like any teenager there was plenty to explore with. After all as a five feet 11 inches, slim, a long legged brunett...

Halloween Party

by damonX on Sep 16, 2017
Group Sex

Halloween.  October 31st and I didn't have any plans.  I had a bit of a headache so I decided to take a little walk around the dorms.  I had heard that there was a big costume party going on somewhere but I hate to dress up.  The halls were pretty quiet for a friday night so I figured everyone must be out for the night.  As I stepped out of the stairwell I h...

Laura's Story Ch. 02

by latesummernight on Sep 12, 2017
Group Sex

I walk in and I can tell you're mad. I look at the clock. It's 7 a.m. I've been out all night. I'm still in my skirt that I wore yesterday to work, though it looks like it hasn't been ironed in a week. "I thought you were 'just going out with some friends'" you glare. "I did. Christ I did!" I say, already tired of the fight that I know is breweing. "It su...

A Co-op Beginning

by Gschuerm on Sep 1, 2017
Group Sex

I've had sex with eight girls so far in my life. Almost of all of them have been decently long relationships. It was not until the summer before I moved to Berkeley that I really understood what it meant to take it easy, you know, not get too excited when dealing with girls who like you. Man, I wished I had learned that lesson sooner, but I'm happy just so l...

Dealing With Post-Exam Letdown

by Moonraker_Bond007 on Sep 14, 2017
Erotic Couplings

Okay, so my name is Chris Johnson. I am not tall at all - I'm only 5'5" but a highly muscular wrestler. In addition, I have a dick that hangs seven inches when limp and pops out to eleven when it's erect. I'll admit, sometimes it looks a little freakish, but hey - it earned me the locker room nickname of "Big Johnson", and plenty of girls have enjoyed it! I...

Romancing the Raptor

by Cashmere_Snow on Sep 15, 2017
NonHuman

Tiffany. Maria. Sandy. Destiny. Chastity repeated the names to herself as she directed a coy smile at the man she had brought back to her apartment. Tiffany. Maria. Sandy. Destiny. They were the names of the women he had raped and then sent to the grave in one case and into the ICU with the others. They were women like her—women who shared an... affliction...