Shy Boy Stories

134,021 results
Orientation
Length
Source
Infinite Scroll

The Dildo

by diminutivedemise on Sep 19, 2017
Erotic Couplings

*Edited by Redwings1202 "Hello?" "Hey Brian, it's me. Listen, are you available Saturday? "Depends. What time?" "Like the afternoon, say 2?" "Sure, I think I can manage that." "Great! I'll text my address but, listen, you can't say anything." "You know I never do." "No I mean when you get here. You can't say anything. Not a word ok?" "Wait, what...

The History of Stripping

by Reefkeeper on Sep 13, 2017
First Time

Everyone's over 18 I once had a student who, in response to an exam question, wrote that Australopithecus invented stripping. I had the Genus mixed into a list of Homo sapiens progenitors and was looking for those students who saw that it didn't belong on the list. Obviously Francine hadn't picked up on that fact so she, in a gesture of academic frustrati...

Men Are Like Cars

by xtcnymphette on Sep 13, 2017
First Time

Beautiful Pia an Internet sex star plans a 'sex free' holiday and ends up helping a virgin couple discover their sexual partnership and finds herself falling in love with an older man. First times are always amusing in retrospect. What we find amusing is our inexperience and lack of practical knowledge. At the time it is a serious affair made more hurtful b...

Midwest College Groupsex Ch. 01

by TriumphTread on Sep 16, 2017
Group Sex

Maria is a freshman in college, attending a prestigious University located in the center of the Midwest. Being an accounting major she had to bust her ass to make straight A's like she did in high school. Growing up in a small town on the out skirts of large city, Maria enjoyed the social life that college had to offer. In high school she was pretty shy and...

Life on Zaltar

by Trapper ak Bobby on Sep 14, 2017
Sci-Fi & Fantasy

Authors Note... This is my first attempt to write a light easy reading fantasy that could perhaps include love and sensuality as well as being completely bizarre. It was my hope to be able to produce a "feel good" story. Please let me know by your comments if you think I have accomplished that. Thank you Trapper It was later then Marcie would have liked to...

Connie's Weed Pt. 02

by PaulGerard on Sep 25, 2017
Sci-Fi & Fantasy

Connie's Weed, Part 2 — Standing On The Bosoms Of Giants A four part tale, laced heavily with lesbian encounters and strange transformations. ~ A word of warning, before you even start reading: A lot of what happens in this story focuses on the rather weird fetish of Breast Expansion (BE) -- from A to D, and occasionally up to and ultimately beyond the si...

Creme Brule: Connor

by Cognantreverie on Dec 23, 2019
Interracial Love

I feel like I should offer a disclaimer just to be polite. Initially I was going to apologize for my fetishizing of interracial sex but I'm not sorry, I think it's hot. Since starting writing here my readers have been far more vocal about what backstories they want to hear. This story was requested by the subject whom we will call Connor. I asked the group a...

The Virgin Delivery Girl Teases

by nylonpunkie on Oct 5, 2020
First Time

My very first job was at a bakery on the outskirts of the city, not a little artisan patisserie but a massive industrial edifice that was organised like a military operation. Three o'clock in the morning I had to wake up and catch a bus, along with a handful of other ghostly figures going to their own ghastly employments; the journey took a long, meandering...

Family Issues Ch. 12

by allthatisfuta on Sep 10, 2018
Transsexuals & Crossdressers

Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. As always, I need to thank, Stylus and Madison, my cool editors - for their endless patience, and great insights. Last chapter had ton of complaints, and mixed emotions. I've been building the gangsters stealing Helen's company since chapter 3, and I tho...

The Indecent Proposal Ch. 04

by whome712 on Sep 18, 2017
Erotic Couplings

John was running late, and I was worried that he was going to miss the plane. He had to meet a client for lunch and we had agreed that we would meet at the office at 2:00 and drive to the airport together. I'm a punctual person, and he tries to be but sometimes things get in the way. Our flight was at 5:00 and we're about 30 minutes from the airport. It's no...