Shy Guy Stories

162,824 results
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Infinite Scroll

Bowled Over

by Frenchman on Sep 14, 2020
Erotic Couplings

(Dedicated to my old gang from Mar-lin-do Lanes) A true story of Gutter-lust Introduction I was a 19 yr. Old kid in college living in an upscale area of the San Fernando Valley. It was a 'Cottage Community' near Hollywood in the late fifties and I was commuting to the local Glendale College Campus while living at home so as to save money. My folks had mone...

Impossible Threesome Dream

by lyruv on Aug 18, 2017
First Time

Mine is a special story, and a long one too. You must be patient and be really interested to keep on reading. 22 is too old to have sex for the first time with a girl. That was my case. I was probably too shy and girls didn't seem to be attracted by me. In general, there were no places where young people could have sex at that time. So I had time to explore...

The Game

by GirlOnAWire on Aug 31, 2017
Exhibitionist & Voyeur

"See anyone you like?" He leaned in and whispered in my ear. I smiled and took a sip of my drink then quickly scanned the bar. I loved this game. "He's not too bad...." I nodded toward a good looking young man sitting alone at the end of the bar, a few seats away from where I sat. Almost as if he had heard us, the young man glanced in our direction and sh...

Pakistani Wife's First Threesome

by hitman221 on Sep 19, 2017
Loving Wives

Note: Please read my earlier two posted stories if you want to enjoy this story fully and completely. * It finally happened, after many years of fantasizing on my part and over the years slowly opening up my shy, conservative wife Hina, my ultimate fantasy has finally become fulfilled. I am Junaid, and this is the true story of my wife Hina and me that h...

Best Friends

by meibuo on Sep 14, 2017
First Time

Simply put, Jackie is one of the hottest girls in school, in town, and on earth. There has never been a guy who's seen her and was not attracted to her. And she is aware of that. Unlike most popular girls though, she is nice and easy to get along with. Of course, she always dates jocks and hot guys. She has hit it with many people at school, no less tha...

Lynn and Leif Forevermore Ch. 01

by mich80new on Sep 14, 2017
Interracial Love

Leif fell in love with Lynne from the instant he saw her. Singing, almost alone, in a crowded bar, with creamy beige skin, and soft brown hair which she wore shoulder length. There was a different quality to her, almost ethereal. She was a cute, petite black girl, with great legs, and a wonderful ass. But that wasn't what attracted him to her initially. It w...

How To Pick Up Women Like Musicians

by NickFoxx on Sep 13, 2017
How To

I'm writing this for three reasons. 1. I grew up singing and playing guitar, bass, piano, sax and flute. And before you ask-Yes, I picked up girls while playing flute-so I know what I'm talking about. 2. I've slept with a number of women and I met virtually every single one of them (including my wife and my ex-wives) when I was in a band. In all honesty...

Alicia's Day Of Pleasure! - Part 1

by Chubby Chic on Sep 14, 2017
Erotic Couplings

Alicia was just a normal woman, aging like a fine red wine she liked to say. She wasn't the only one to think this either. Karl, a close friend of the family totally agreed. He and his wife Julie had know Alicia and Greg (Alicia's husband) since they were all in high school. He had always had a 'thing' for Alicia, but Greg the bastard stole her heart first....

Two Thumbs Up

by Czarina on Sep 14, 2017
Exhibitionist & Voyeur

I came out of my office, frustrated as usual. Why was a women of talent and accomplishment subjected to such mindless drudgery as a 9to 5 job? I should be an accomplished author with hundreds of thousands of readers clamoring for my latest book. That was the Gypsy’s prediction. Millions would express their deep appreciation for my craft by making me a millio...

Tits Have Benefits Ch. 09

by hottchic on Sep 18, 2017
Transsexuals & Crossdressers

Following her honeymoon life starts to assume more of a normal routine for Andrea, well as normal as you can get when you are a shemale t-girl in a family with 4 lesbians. Kate finds a shy new boyfriend and asks Andrea for help with him. But can Andrea's idyllic lifestyle continue indefinitely, in this story things events take a nasty turn... * After tra...