Gay Roommate Stories

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Sexual Secrets Ch. 06

by DickSwett on Oct 26, 2020
Gay Male

Two weeks into the new semester, just as the calendar changed from January to February, a powerful nor'easter battered the New England coast and blanketed the state of Maine with five feet of fresh snow. Logan Temple, the sandy-haired freshman boy from California had never seen anything like it. He never imagined so much white powder could be spilled in such...

You are a Sissy Pt. 04: Women

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello again, sissy. Hello, my sissy bitch. I am so happy that you are back yet again. You love coming back to continue our sessions, sissy. You love coming back because I am helping you. You need my help. You know you need my help, sissy. You need to come out of the closet and let the world know what a gay cocksucker you are. You need to let the world know...

Christening the Couch Ch. 01

by Steplianna on Aug 18, 2017
Gay Male

Laying in his bed, engrossed in his favorite daydream about his roommate, Trey, Tye felt his cock begin to swell; reaching for it, he wrapped his fist around the thickening shaft and set up a friction that matched the intensity of his thoughts which began with slow, erotic visions. Envisioning Trey’s smooth, naked body in the shower with the steaming water...

You are a Sissy Pt. 05: Master

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello, sissy. Welcome back, princess. Welcome back to our journey through your sissy mind. You will always come back because I am what you want. I am what you need. You need my soothing voice. You need to hear my voice telling you what a fucking faggot you are. You need my voice telling you what a faggot you have always been. That makes you so happy. You...

You are a Sissy Pt. 06: Slave

by Roland15Rollin on Dec 25, 2019
Gay Male

Hello again, princess. Welcome back. Welcome back yet again to our journey through your mind. Our journey through your feminine girlie mind. We are almost there, princess. We are almost to the end of our journey together. I know that makes you sad but it's okay. It's okay, my sweet sissy. It's okay because we have more to cover and I will always be with you...

My Roommate's Toy Box Ch. 01

by brycemanning on Jul 27, 2020
Gay Male

Author's Note: This chapter sets up at least two more that will contain the action, the second coming in a few days. I'd skip the story if you're going to find large sex toys off-putting. The premise was way more fun with objects that wouldn't be easily explainable. *** I moved into my freshman dorm room on the very first move-in day available for the fall...

Poor Todd

by Tallywacker on Mar 7, 2019
Gay

Today was your first day of classes. You had barely settled into your college dorms exchanging little more than a hello with your roommate before he had fucked off to hang with his friends. All in all you are feeling more than a little stressed. Looking at your mirror you take in your appearance, with tanned skin and blonde hair you could almost pull off a s...

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Stranger on the Couch Ch. 01

by PSNudist on Mar 28, 2018
Gay Male

I woke up with a start, raising my head and looking around my messy bedroom as I rubbed my eyes. I soon realized that I could have been awakened by the pounding in my head. Too many martinis last night? I tried to remember and came up blank. In desperate need of aspirin, I pulled the comforter off me and immediately felt the room's chilly air on my naked bo...

Love Without a Baseball Cap

by neko_rae on Aug 18, 2017
Gay Male

This idea come to me one day in the dinning hall watch two guy, who were roommates, eat together. The thought passed through my head the two of them would be the cutest couple if they ever started going out. I then started to think what their first time as lovers would be like for them. A day later I started on this story. I hope you like it. As he looked a...

A Load of Help

by Brass_ankle on Nov 27, 2017
Gay Male

Connor was perspiring as he made his way to his dorm room. A great deal of things were happening all at once in his life; it was mid-terms and his girlfriend back home dumped him the night before. To top it off he didn't get enough hours at the Hortons on campus to help pay for his portion of the rent. Wiping sweat off his brow he fretted how he'd get the m...