Shy Boy Stories

134,021 results
Orientation
Length
Source
Infinite Scroll

Oh, Library Boy!

by nymphobrainiac on Dec 25, 2019
Exhibitionist & Voyeur

He stood there by the brick wall, a book splayed open as he stared down at the pages. I couldn't help but notice the length of his fingers as he scanned the words one by one, and his tongue as he licked the very tips to turn the page. Silly me, having these glimpses in the library. Silly me for having decided that I must get a closer look. As I trailed arou...

Dakota's Surprise Pt. 02

by mfan2112 on Oct 6, 2020
Transgender & Crossdressers

Dear Readers, I hope you find this story interesting. Unfortunately, there is not that much sex in this part, but there will be more in future parts. Please consider reading the first part if you have not done so already. Special thanks to my reviewers who helped identify many errors, but I am sure a few still exist. If you would like to be on my team of edi...

Luk in a Lincoln

by KeithD on Jan 7, 2020
Transgender & Crossdressers

"Park it in a safe, remote area, please. A girl wants to feel safe." The voice was soft and deep, with an alluring foreign accent. The figure was small, shapely, with long, black hair, a China-doll face, and a slinky crystal-beaded-covered spaghetti-strapped top, buttoning down from the cleavage split, above a matching, tight, miniskirt—a figure that sparkle...

Poornima's Sexual Journey

by svh7219 on Oct 6, 2020
Erotic Couplings

Disclaimer: The name of the characters are changed for privacy purpose and any resemblance to any person alive or dead is purely co-incidental. I will be narrating the story in two or three parts, depending on the feedback I receive. I am narrating it as it was narrated to me by my friend. It was raining incessantly for the last 3 days, and Poornima had r...

The First Time I Touched a Boob!

by MrAlex on Apr 17, 2018
First Time

My name is Alex and this story I am sharing you is about the first time I touched a girl's boobs and how it all happened... My name is Alex (23 years old) and I am an engineering graduate. Like all virgin boys I always wanted to have sex with a girl and wanted to run my hands and tongue all over her body. It all happened after I got my first job in Cana...

Daniel and Aubrey

by SykotikOne on Mar 13, 2018
First Time

Aubrey was a shy but beautiful girl. She had long straight blonde hair, blue eyes, and she was slim but not overly skinny. All the boys talked about her, and on several occasions, she had boys try to go out with her, but because of her shyness, she turned them down. There was only one boy that she had on her mind, and that was Daniel. One day, Aubrey was in...

Lusus University Ch. 04

by Sonnetprose on Sep 16, 2017
Sci-Fi & Fantasy

Shylah got up from the chair that she was sitting in, looking about her darkened dorm room. Mel wouldn't be home tonight, Shy knew this, so if she was going to attempt any spell casting, tonight might be a good time to try. She moved over to her shelves and looked over the ingredients and items as the thought about what she'd need for the spell. "Lets see...

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...

The Slut Couple

by kin1041 on Sep 30, 2019
Swinging

The Slut Couple is inspired by the cover art (made by Chromosomefarm from Hentai Foundry). The idea of a slut couple was interesting and I liked the idea of couples getting into sexy situations but coming out of it still together if not a little twisted at the end. Something like borderline netorare and such. So before we begin; who's the couple?What's next?...

Open in Reader

Ryan's Friend Lisa: The First Night

by dcrane1978 on Sep 19, 2017
Exhibitionist & Voyeur

How good is Tracy, in helping with my fantasies? You'll see. For example: Lisa. I see Lisa every week, sometimes twice a week, since we sing on the praise team together. Lisa will tease me a little, and likes to be teased, or complimented, so that's fun, almost flirty at times. She's a little shy in some regards (until a few beverages are flowing) but so ni...