Roommate Cuckold Stories

20,909 results
Orientation
Length
Source
Infinite Scroll

B Is For Bareback

by velvetpie on Sep 13, 2017
Erotic Couplings

Inspired by Sue Grafton’s alphabetical series. He was absolutely gorgeous. No two words about it. GOR-GEOUS! I hoped it wasn’t the flashing lights or the hypnotic strobe that brought me to that decision. He had a headful of dark, curly hair that draped over his shoulders and the darkest eyes that I’ve ever seen. I think I joked with my friends that he mu...

Crystal Pegs Ch. 03

by rckplsky on Sep 16, 2017
Anal

The cum was still dripping from my face as I followed Crystal to the guestroom. I found her on the floor, crying, she still had on the strap on and her thigh high boots. I lie on the floor next to her. She tries to push me away, but she barely resists. "I'm sorry," she says while tears engulf her face. "It's okay," I say trying to hold back tears of my own...

Katherines first fuck at college

by MichelleRheimes on Sep 13, 2017
Exhibitionist & Voyeur

This is a true story about a former girlfriend. We made love many times before. She related this, her first college experience to me. She was a freshman at the time. She attended a prestigious "off Ivy" eastern college. The first time she saw him was in class. It was her first day of contemporary American history. He did not really notice her. She sat far a...

Teaching The Wife A Lesson Ch. 04

by daddydearest on Sep 17, 2017
BDSM

Mike, Terrie and Sandy get back to the house. Terrie leads Sandy into the living room. “Make yourself at home we’ll be right back.” Terrie says to Sandy. Mike and Sandy go into the bedroom and change into something a little more comfortable, and walk back into the living room sitting on either side of Sandy. “Did you enjoy listening to us back at the club?...

The Cheating Game 03

by jonthechaosman on Sep 14, 2017
Loving Wives

Elaine: I grew up in a home without much affection or supervision. My birth was a surprise for my parents who had just shipped my sister off to college and thought that they could finally relax. I suppose I acted out and partied to get attention but they were just tired and left me alone. My friends weren't the best influence either. I started having sex at...

No Pressure

by Alibug136916 on Sep 12, 2017
Fetish

This is maybe not the best of stories, but it really did happen and it was an awesome experience so I thought I would share it with you, Dear Reader. It was getting late. He had to be up early the next day (and consequently, so did I- I didn't want to be alone here while he was out for the day and the housekeeping staff were going about their business). I w...

Beauty Night

by velvetpie on Sep 14, 2017
Erotic Couplings

"Oh, come on, Barry. Come with me. You'll have a ball!" I just glared at my friend, Ronald. True, it had been awhile since the accident but my arm was still in a cast and my face was still riddled with the livid bruises, visual reminders of the horror I'd suffered through. The horror that still haunted my dreams. The piercing screech of tires, the bright sm...

The Party Ch. 1

by kallih2 on Sep 12, 2017
Group Sex

The music was loud as I sat there, feeling naked in my black teddy, matching thigh highs and 4-inch heels. Sammy, a close friend and suite mate, told me about the party and promised that it would be fun. "Besides Kallisti," she argued, "You need to let your hair down and forget about Brad." I knew that she was a bit wild and into orgies, and I think that thi...

After-Class, After-Life Affair

by Rumple Foreskin on Sep 16, 2017
Interracial Love

(note: This story is an entrant in Literotica's Halloween Story Contest 2004. IMHO, it doesn't have a ghost of a chance. But I hope you enjoy this non-family escapade by the sexually adventurous, Randi Druitt.) -- It was a fantastic fuck. Randi Druitt's sex-charged body writhed and shuddered. A large, powerfully built man was between her widespread legs. W...

Jaime and Mike Pt. 02

by LadyMelodyDarkheart on Nov 20, 2018
Transgender & Crossdressers

Welcome to part 2 of Jaime and Mike. If you haven't read the first part I suggest you start there. And as always, Enjoy! *** So here I am, dressed like Han Solo, on my hands and knees with Jaime behind me. Her slave Leia costume is perfect as she slowly makes love to me. Its been 8 months since we met, and I couldn't be happier. I can feel her getting clos...