Roommate Chastity Stories

20,671 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

Anal Virgin

by DaddysGrl on Sep 15, 2017
Anal

Molly and I sat there waiting for Dennis. He was a friend of hers. Well, more like an acquaintance. He was roommates with her boyfriend, John and her boyfriend had asked her if she knew any young girls…Dennis like young girls. Even though I was in a relationship at the time, she instantly thought of me because she knows I love older men and would never pass...

Mandy Gets Her Man!

by easytvgirlmandy on Sep 16, 2017
Transsexuals & Crossdressers

One long hot summer a transvestite girl named Mandy was working away in a remote location on a project. There were positives and negatives to working so far away from home. The major negative was that she had no wardrobe at hand, except a well concealed bra and a pair of panties. Mandy used these to slip into in the bathroom and enjoy brief moments of the fe...

African-American Wedding

by Samuelx on Sep 14, 2017
Erotic Couplings

There is an old saying that once you do certain things, undoing them can prove difficult or even impossible. I'm starting to agree. My name is Alec La Pierre. Pronounced exactly the way it sounds. A six-foot-one, lean and wiry young Black man with light brown skin, curly Black hair and pale green eyes. My father Napoleon La Pierre is Black and my mother Eile...

A Restless Week

by sagitair on Sep 16, 2017
Erotic Horror

William was exhausted. This was the third day in a room he was barely able to drag himself out of bed. The very thought of all the work involved in dragging a razor across his face left him listless. So instead he sat there staring at his bowel of cold cereal, rubbing his cheeks and feeling the sandpaper texture of his skin. 'You look like shit,' his roomma...

The Argument

by Monsoon6391 on Sep 12, 2017
Romance

He's your roommate, I thought irritably to myself. Your relationship is platonic. But somehow, watching him walk out the door with Amelia, the busty blonde from next door, all of that logic flew out with them. I had been living with Max for a year now. We'd gotten close in an AbPsych class our sophomore year. Neither of us wealthy enough to support oursel...

Hair-Raising Encounter

by VTDarkAngel on Sep 16, 2017
Transsexuals & Crossdressers

(Note: The original in this series was entitled "Falling For My Roommate, of which this is a continuation, which includes "A Trip To The Park" and "My Sweet Little Crossdresser." It was a rather difficult trip home, even in the light of some of the things I had been through. It was most difficult leaving because of Marty, my sweet little cross-dresser who I...

Educating Marri Ch. 01

by MarriPetX on Sep 14, 2017
Novels and Novellas

A college girl becomes a prostitute to pay the bills. The fire alarms were blaring everywhere and everyone was scrambling to get out. I grabbed my purse and hurried out of the room. I joined the small parade of girls heading down the stairs and out of the building. I didn't see any smoke or fire, but I wasn't crazy enough to go looking for it. Once I was o...

She Doesn't Pt. 03

by barnabus on Sep 12, 2017
First Time

Chapter 4: Discovery By now, I knew that she was totally love-starved, but I still wanted to move slowly to allow her the maximum opportunity to enjoy our time together. It also allowed me the chance to savor her even longer. She was tight as a drum, so I just held her, and cuddled. Women always like to cuddle . . . It makes them feel loved and valued as...

A Walk to Forget

by shamelessme on Aug 19, 2017
Exhibitionist & Voyeur

It was the last few days for me in Bangalore, my hobby of displaying myself to women was coming to an end and I thought it had already reached its zenith. Now there was a girl named Aishwarya who stayed near my place. She was a colleague of mine and we knew each other but hardly spoke. She would have to cross my place to go to hers when she returned from off...

Frau is a Dirty, Nasty Slut

by historycup on Aug 19, 2017
Exhibitionist & Voyeur

I've taken three years of German language class. I did that because it's the requirement to go on the trip to Germany with the class. The class was taught by one of the sexiest women I've ever encountered and she just so happened to flirt with me every chance she got. It got to the point where the class thought we had a thing until I waved it off. The teach...