First Time Gay Stories

351,239 results
Orientation
Length
Source
Infinite Scroll

Anal Sex with Stranger on a Train 05

by SusanJillParker on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 5 Peter finally meets Roberta again, the love of his life. In just a few minutes, Robert returned to the room dressed as Roberta. Giving him a sexy cross dressing show, by her feminine antics and charms, she obviously enjoyed being watched by Peter. With a shake of her head and with a flourish, as if releasing her sword in Zorro, the gay blade, sh...

Thai Travels Ch. 05

by S_Queen on Dec 28, 2017
Group Sex

Hello again readers. Welcome to another chapter of my erotic travels through Thailand. If you've joined me without reading the other segments, I'd suggest doing so for contextual reasons. Having said that, this is a standalone encounter, albeit with familiar characters. If you've read my other chapters, you'll be well versed by now on my abilities to give in...

The Gynecomastia Kid Ch. 02

by Johnboy9 on Sep 16, 2017
Transsexuals & Crossdressers

It's been two weeks since I got out of the hospital and I was feeling better and better as each day passed. Having no income and no real money of my own, to speak of, I was forced to continue wearing the clothes that Crystal left me since I couldn't afford to go out and buy clothes of my own. I must say though I'm getting to like the soft, airy feeling of t...

Owned by The Boss and Her Gay PA Ch. 01

by labrysuk on Sep 16, 2017
Fetish

This is a story that will take place over a few chapters. Some of it, both what has happened and the feelings behind it, is true. Most, unfortunately, is just fantasy. The main characters, m,e Jo, and Andy are all real people and I've kept as close to the truth as I can without giving away who we actually are. * I first met Andy some years before this st...

My First Bisexual Experience

by desires2 on Sep 12, 2017
First Time

Let me say straight off that I don't consider myself bi-curious. Bi-sexual, or gay!! I'm not attracted to guys at all. I don't want to touch them, kiss them and I never look at guys with any sort of sexual thoughts. Having said that, as a teen I had this friend and we did engage in what can only be described as bi-sexual behaviour, and sure - I guess it w...

Here Cums the Bride Ch. 02

by ILookLikeJailBait on Apr 17, 2018
Exhibitionist & Voyeur

One man having sex with four, sexy women on the eve of her wedding, the bride, the maid of honor, and the two bridesmaids, what are the odds of him getting lucky. I'd say pretty good. Continued from Chapter 01: In the way that he did last night, he scooped her up in his arms and carried her to her bedroom and gently put her on her bed as if she was someone...

My First Gay Experience

by gravelmeter on Sep 2, 2017
First Time

My first gay experience was right after college in the summer of 1989. Three days of hitchhiking across the states found me sitting under an overpass in Birmingham, AL feeling fresh after a long shower at a nearby truck stop. As I sat holding my thumb out I remember thinking about a guy in a van that had obviously wanted to have sex with me, but I turned him...

She-Male Chronicles Ch. 3

by Anal Slave on Sep 12, 2017
Fetish

Last night my wife took me to a she-male bar and she made me dress up like a slut. We took a taxi on the way over their and my wife made me give the taxi driver a blowjob. He thought he was getting sucked off by a female, if he only knew a man dressed up like a woman was sucking his cock. When we got to the club I saw a she-male that fucked me last time we w...

I See a Red Door

by sublocked on Sep 12, 2017
BDSM

She paced slowly, methodically, back and forth like a tigress behind bars in a too-small cage. She smoked, and he hated that, but it looked right at the moment, the smoke curling from her ruby lips, sifting through her raven black hair, like flour through a sieve. She loved black it seemed, as he had seen her in nothing else. The outer garments were not pres...

Felicity Ch. 02

by jjcolejr on Sep 12, 2017
Novels and Novellas

A Conversation by jjcolejr "Why are you bothering with me?" "I'm sorry. I did not mean to bother you. Have a nice evening." "No, no. You were not bothering me. I just wanted to know why you were with me instead of those girls over there. They are a lot prettier than me and you are the type of guy they fall all over themselves for." "You know them?" "Y...