Shy Guy Stories

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Shy Guy Hero

by kumachanz on Sep 26, 2017
Interracial Love

The security guard's lazy Sunday afternoon watching the big game is momentarily interrupted as he sees an employee swipe his card and walk in through the main door. The guard turns back to his small TV set, grabs another handful of peanuts and settles back in his chair. George puts his access card away, smiles and waves nervously to the guard who is now ign...

My First Dominatrix

by JackWanker on Sep 16, 2017
BDSM

I was always a shy guy who had a hard time getting girlfriends. By the time I was 20 and going to college, I was still a virgin. My sex life consisted solely of masturbating to dirty magazines, videos, and the like. Often I fantasized about being dominated by one or more females, but I hadn't gotten even close to acting it out. That year, I moved into a new...

Linda Ch. 01

by ableoneable on Sep 17, 2017
First Time

I was a shy guy in high school and I never dated until well after graduation. I also suffered from a distinct lack of "game". My conversation turned wooden in bars and other social venues thus impeding my ability to hook up. During the summer after my freshman year of college I was lucky and landed an internship at a local T.V. station. One of the anchors...

At The Pool (for a Shy Guy)

by LeanneSinclair on Aug 19, 2017
Exhibitionist & Voyeur

After the first month, being at University in London was not turning out quite as Kevin had hoped. Not that he missed his small home town, but he'd had such high hopes of the capital. But everything was expensive, it took ages to get anywhere, the studying was already pretty intense ... and he still had his virginity. Yep, that was the killer. Not that he ha...

Reminiscing about Her Deliciousness

by my_slut_mouth on Jan 22, 2019
First Time

I am typically a shy guy, with very little to say, typically in public. Since my teenage years, I've enjoyed using my mouth in the sexual department more than not. I'm picky when it comes to my sexual partner. There needs to be some kind of connection. And besides, I like to know what I am getting in too. One night I decided to join one of those BDSM feti...

Slave to the rich and famous

by Slavedogg on Aug 14, 2020
BDSM

You are a shy guy average age. But when it comes to sex you have the worst luck. Most of this is down be a total submissive slave boy and way too much of a whomp to tell anyone or even visit a professional dominant. Though you have tried a few things like your vanilla sex life you never been that far. You are pretty certain that your ex the only one to have...

to the rich and famous

by Slavedogg on Apr 22, 2025

You are a shy guy average age. But when it comes to sex you have the worst luck. Most of this is down be a total submissive **** boy and way too much of a whomp to tell anyone or even visit a professional dominant. Though you have tried a few things like your vanilla sex life you never been that far. You are pretty certain that your ex the only one to have s...

You've Got Lucky! Pt. 01

by lovewriter on Sep 28, 2020
Loving Wives

This is a story about a shy guy next door, and the unexpected turn of events in his routine life. A million pieces fall into just the right place to make him the happiest guy on the planet. The story starts off with a bang, and slows down, and picks up again, and goes on. If there is a description for getting lucky, then this story is it. You know what, that...

Sometimes Nice Guys Finish First

by jonthechaosman on Sep 13, 2017
Loving Wives

This was another odd little idea I had. Another "What if?" story premise. It's not a stroke story but there is some sex. It's not really a great fit for LW but it's not really romance or erotic couplings either so I put it here. ***** The seventh annual end-of-summer neighborhood bbq was going well. It was our year to host and we had gone all out. The host...

You Have to Meet this Guy

by ItalianLace on Sep 17, 2017
BDSM

"You have to meet this guy," Jenna tells me. I work with him, and all I can think when I talk to him is that he'd be perfect for you." "How so?" I ask with a mouthful of chicken salad. Jenna gives me that sweet half-smile she does when she's only half telling the truth. "Well, he's shy at first. But he's so smart and so funny once you get to know him," she...