Shy Guy Stories

162,824 results
Orientation
Length
Source
Infinite Scroll

Gone BLACK...Again!

by sara00smile on Sep 13, 2017
Interracial Love

I had always been fairly shy and conservative when it came to sex. My husband had always tried to get me to relax and try new things. I would fantasize with him during sex, but afterward never acted on those fantasies. My favorite fantasy was the one where I found a black guy and fucked him. I had been with a black guy once before and knew it was wonderful,...

Tina's First Exhibitionist Experience

by Loginer00 on Sep 13, 2017
Exhibitionist & Voyeur

This story is based on real events. Feel free to rate and comment. Special thanks to my editor Pete_L . * Hi! My name is Paul and this is a story about me and my girlfriend's first exhibitionist experience. I'm just an average built 22 year old guy who lives in Europe. Like most students who are attending college in their own town, I live with my parents....

Bedroom Surprise Ch. 02

by wylite on Sep 13, 2017
Fetish

I endured several more bedroom cleaning sessions; each time I wore my sissy pink dress and panties but I think Mandy and Beth had become bored with this routine. I had a definite feeling that they were cooking up something for me. I still wore the chastity devise but had received no more release from my pent up sexuality. A good solid hard on was not a luxur...

Bimbette's Valentine Fashion Show

by Jackson Blacke on Sep 14, 2017
Group Sex

Bimbette decided it would be a good time to neaten the widow display at Samantha's Sexy Slut Salon. It was an hour before closing on Friday, February 13th, a doubly bad day for her. Friday the thirteenth is intimidating for most people, of course. But it was also the day before Valentine's Day, which was especially depressing for Bimbette. The reason was t...

The Fame Game

by adam applebiter on Sep 16, 2017
Anal

"So who's Lois?" She asked, returning with a second round of drinks and some change for the pool table. "You rack 'em. This dress..." She let the sentence hang in the air like a tantalizing whiff of perfume that instantly reminds you of a long forgotten encounter. And her hem was rather high. And where the pool balls came out was rather low. I racked them u...

Some of Sam

by flat5ive on Sep 1, 2017
Group Sex

The first time I was with another couple was in California. I worked at night as a musician, spent days running, biking, practicing. Occasionally I'd pick up a movie at the local adult store. Adult store patrons are the same the world over: middle-aged married men, rendezvous-ing gay men, horny twenty-year-old gotta-get-off-NOW men (that was me). Drunks and...

My Twin Sister is a Cheerleader Ch. 02

by Callicious on Sep 25, 2017
First Time

If you have not read Chapter 1, please read it first so you understand what is happening. If you are looking for a quick jerk and a lot of sex this is probably not for you. There is no actual intercourse in this chapter, although there is sexual activity. This is an exploration of an extremely shy young man who is taken advantage of by senior cheerleaders,...

Janice Worthy

by GeneMajors on Jun 1, 2020
Romance

© 2020 by author This story encompasses 3700 words and 7 book pages All Characters are age 18 or older at time of the story. Few of my fellow classmates at Sunny Slope High paid much attention to Janice Worthy. Not that she was unattractive, she wasn't. Slim, five-seven maybe, medium high cheek bones, medium brown hair, skin and complexion that seemed to...

Shy Wife Ch. 03

by daydreaming101 on Sep 19, 2017
Exhibitionist & Voyeur

Chapter 3 – Black's Beach Revisited I had set out to get my shy wife Chris to be more adventuresome. Not every attempt was successful, and I will not bore you with my failures. But I am still working on Chris, without pushing her too far. She had gotten naked on the Black's Beach before and had her picture snapped with a tourist (Shy Wife #1), she posed for...

Cinema Fantasy

by ToldInTurns on Aug 31, 2017
Group Sex

This is a fantasy, told in turns. We worked on it together, taking it in turns to write a section, without each of us discussing where the action would go but letting our fantasies dictate the turns of events. We've been to a cinema and fucked each other while others have watched, but nobody has yet tried to get involved... He writes: We agree to meet at...