Literotica, Cum In My Virgin Gay Ass Stories

360,735 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Happy Nude Day Ch. 08

by BOSTONFICTIONWRITER on Sep 25, 2017
Humor & Satire

Jason's Mom and Grandmother stood naked in the archway between the kitchen and the living room with their arms folded. Sensing the seething synergy coming from the woman of the house, the room went suddenly silent while one by one, but for Susan, they all looked towards the archway and her. Still poised on her knees in front of her father, Susan hung her hea...

Not The First Time He Imagined

by super_chicken on Sep 13, 2017
Fetish

He was a 22-year old virgin. He hated it. He didn't know why girls didn't like him. But he had ideas. He couldn't understand why guys he knew who were even shier than him could get chicks. He could meet girls. He had friends who were girls. But he could never take it to the next step. He could never show his interest properly. Part of this was because he had...

Auburn Mistress Ch. 02

by ukmaleslave on Sep 18, 2017
BDSM

The red headed woman who stood over me had at first started off as a customer then quickly turned into a friend, how was I to know that she had other plans for me? I’ll get you up to date, we ad gone for a drink and whether she drugged my drink or I suddenly couldn’t hold much I found myself awake in her spare room dressed in her underwear, gagged. My hand...

The Alpha Who Made Me a Sissy Ch. 02

by HB77 on Jul 31, 2019
Transgender & Crossdressers

Chad texted me a few days after our first encounter and I was super hesitant to return his enthusiastic messages to see each other again. I was racked with feelings of confusion and shame. Was I gay? What will my life be like? I really didn't know what to think or what I was feeling. But he persisted at easing my apprehension and I finally agreed to meet for...

My Initiation

by lockedupslut on Sep 13, 2017
Transsexuals & Crossdressers

(This story is a work of fiction. If you don't like erotic stories that contain cross dressing, heavy gay themes and water sports please just don't read it. Thank you.) * I was determined. This weekend it would happen. I would loose my gay virginity and complete manhood. The hard way. Tonight would change everything. Until now I've never had sex with a ma...

The Doctor Ch. 01

by gayghostwriter on Jul 17, 2018
First Time

If you have any ideas for new chapters or other stories, please feel free to email me at my profile. I'm new to writing erotic stories so I appreciate your feedback! Enjoy the story! ~ My name is Lucas. I'm a closeted gay 18 year old. I never planned on my parents finding out that I'm gay, but my secret was let out after they found gay porn on my lapto...

College is a Time to Explore Ch. 01

by ddogg44 on Sep 15, 2017
First Time

I didn't know what I was thinking. My hands were still shaking from the excitement. My heart raced as I finished verifying my craigslist account. My online ad, which garnished a picture of my plump bottom being spread wide to reveal my sweet hairless hole was titled "Teen ISO Daddy". I stated that I still had my anal cherry, in fact I had never even been wit...

Her New Bra

by evil_in_the_flesh on Sep 11, 2017
First Time

Kimberly O' Brien was stretching before gym class started. All the guys in the class couldn't help but watch as Kimberly stretched. Even the girls eyed Kimberly's stretching. This was an everyday event for the guys and girls to watch Kimberly stretch. The 18-year-old had a massive bust. Kimberly would notice her fellow gym students looking and glancing at h...

A Day In The Park

by TheRandomOne on Sep 14, 2017
Erotic Couplings

Have you ever heard of people who claimed to once be gay, and then they turned straight? No? Not really, you say? Well, that's probably because it doesn't happen too often. However, about three years ago, I had an experience that turned my life from gay to straight – in the space of about half an hour. To start off with, you need to understand my background...

Aaralon's Discoveries

by Sixth on Apr 18, 2002
Fantasy

Aaralon was nervous; he was not only disobeying conventional wisdom by attempting a summons but he was flaunting the strict rules of the boarding school by doing so. He was twenty years old and had been in College of Light Shadow for the last fifteen of them, he couldn't really remember what his parents looked like and all that really seemed to matter about...

Open in Reader