Gay First Time Straight Stories

22,593 results
Orientation
Length
Source
Infinite Scroll

Intimacy Ch. 01

by sampound on Aug 18, 2017
Gay Male

Introduction: It's funny- a lot of times when people meet us they think Jeff is the gay one and I'm the straight one. He's not effeminate, but he is an art history major with a David Bowie obsession. He dresses like he's ready for a party at Andy Warhol's Factory at any moment. He even LOOKS gay- practically hairless and very slender, with pouty lips and h...

Fantasies

by LittleTommyTudor on Aug 18, 2017
Gay Male

I got married at a very young age and both my wife and I were virgins. She was raised in a very strict environment and believed sex was for having children. Although I was a virgin, I knew that sex was also for pleasure and enjoyment. For years I had been masturbating and having sexual fantasies. On our wedding night I must have fucked her 3 or 4 times, but...

The Jamaican Fucked Me

by norm55 on Aug 18, 2017
Gay Male

At last I have the courage to write about my sexual experiences. All the stories are true. Only the names have been changed to protect the guilty. STORY 3 Two months later I was moved to another department within the railway works. I became settled there. 12 months later I became engaged to a girl from a small town some 12 miles away. Looking back I think...

Right Where I Belong Ch. 01

by anon_temptations on Sep 19, 2017
Gay Male

Matt lay across his bed and stared up at the ceiling. Mitchell had just left after collecting the last of his belongings and he was now all alone. It had been two weeks since Matt had walked in on his boyfriend of two years having sex with Ben, a mutual friend who they'd both gone to university with. Matt thought back to that day when he had let himself into...

Letting Him Down Easy Pt. 03

by vikkihawe000 on Dec 2, 2019
Gay Male

"Checking in," Jessy said to the hotel clerk. "Reservation under the name 'Jessy Smith.'" The woman with the frizzled hair looked concerned for a moment, but shook her head. "Here you are, first to arrive in room 3320. How many keys would you like? 2?" She said glancing up at Eli standing next to her. "Five," Eli corrected her. "We're having a few friend...

Master Jakob

by MJwv1997 on Feb 13, 2018
Gay Male

I was on my way to finally start my life as a slave for Master Jakob. My given birth name was Andrew but as part of my slavery i was given the name Seth. His name is Jakob or Sir to me. He's 6'4" tall with brown hair and the most intoxicating big brown eyes I have ever seen. He has big broad eyebrows a high cheek structure perfect nose and a sensual mouth. H...

Losing my Virginity!

by rodneysteele41 on Aug 28, 2017
Gay Male

My name is Rodney Steele. This year I will be celebrating my fortieth birthday. By my story begins a long time ago. More than twenty years ago, in fact. When I was a young stud of eighteen, fresh out of high school and looking forward to college. I was headed to one of the mid-west's better universities, on an engineering scholarship. I was also headed towar...

Adventures of a "Straight Guy" Ch. 01

by JJM91 on Jan 14, 2018
Gay Male

Ok, so before we start, you need to know 2 things: 1, English is not my mother tongue, so please excuse me if i have grammatical mistakes, hope the story is understandable enough, 2 this story I'm about to tell you, is completely truth, and is based in my journey to the discovery of gay sex, I have read stories about first encounters that were all perfect, i...

DJ - The Story behind The Story

by o2byoung on Feb 6, 2018
Gay Male

I became a member of Literotica in July of 2015, as a reader. I got totally wrapped up in 'Aquata Cove', a fantasy love story by 'feare909', about a blossoming love affair between a young gay man, Adam, and a Merman, Merrick. This story actually ended, finally, at about 101 Chapters. This story had me captivated for many months. If you like stories that have...

"You Go First" 01: Jake Said

by donaldelliott11 on Dec 24, 2019
Gay Male

[Thanks to Ken N. for editing me. This is a story about eighteen-year old college freshmen discovering the pleasure they could give each other when girls weren't around.] *** I didn't lose my virginity until I was in college. In fact, I had very few dates at all in high school because I was so shy. I had no idea why some male and female classmates were so...