Shy Boy Stories

134,021 results
Orientation
Length
Source
Infinite Scroll

A Helping Hand

by Delilah_Morgan on Jul 14, 2020
Mature

It's so nice that you are helping with the dishes, its much more than my kids do. Here you are, 19 years old, helping an old lady when you should be in the other half of the house playing video games with my son or hitting on my daughter. Oh, don't be embarrassed! I know why you are friends with my son, since my daughter turned into a woman all the boys hav...

Exporoni Meets the Neighbors

by Exporoni on Sep 13, 2017
Exhibitionist & Voyeur

When I married my second husband, Ray, I could not believe the freedom I had. My first husband and I were married about seventeen years and sexually he was a real stick in the mud, a boring prude. After him I lived with my boyfriend, Steve, for almost five years. He was fifteen years younger, lots of fun, but VERY jealous!!! Ray was incredible, so nasty!! I...

Love beyond Blue Balls Ch. 05

by CuteAndLovelyYetHorny on Aug 20, 2019
Fetish

Note: (I apologize to Literotica users, this chapter was to be uploaded with the last one months ago, but my mind recorded that this was done with how I cut and re-cut it all. Good news is nothing is dead, bad news is nothing has advanced and I hope this time is the good time when I plan to get back to my stories, but it's been harder since my creativity in...

College Girls Ch. 12

by TheSparkZone on Sep 13, 2017
Exhibitionist & Voyeur

Chapter 12 (Summer Job) I wanted a summer job to earn a little money before returning to college in the fall. There was a help wanted sign posted in the window of a perfume store at the mall, so I decided to apply for the job. It was a small boutique at the far end of the mall with a very expensive line of imported perfume. They offered me salary plus comm...

Mind of its Own

by bananas_4110 on May 26, 2018
Science Fiction

The morning sun was rising in the quiet town of Hampton, MA. Not many fun or interesting things ever happened there. It was cozy, the residents were warm and neighborly. It was surely a happy and peaceful place. The police force here had very little to worry about. The occasional speeders were often the major issues the officers had to deal with. But all of...

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The Brothel in Old Amsterdam

by phantome71 on Sep 12, 2017
First Time

I had always been quite close to my Dad ever since my Mother left when I was quite young. We had always had the sort of relationship with no secrets and when he started to question why I hadn't got a girl friend I wasn't embarrassed. "When I was your age I had been with several girls and here you are at eighteen and you haven't brought one home!" "I know...

Saundra

by geraldf on Sep 13, 2017
First Time

At the time this story happened, I was working as a freelance proofreader for several small publishers in New York. I had come to this particular building on Fifth Avenue to pick up a job. I had always enjoyed coming to this building because it housed one of New York's biggest modeling agencies, and I almost always shared an elevator with one or two models w...

Sex Class Ch. o2

by TheBeavMan on Sep 14, 2017
Group Sex

The teacher despite her conservative appearance was giving me an excellent blowjob. She stopped for a minute to gently push me into a sitting position on her office couch then continued to give me a good licking. I undid the bun in her hair and ran my hands through it as she bobbed her head up and down on my rock hard prick. She knew what she was doing as sh...

Sylvia Seduces

by geronimo_appleby on Sep 19, 2017
First Time

Another from me, this time charting a young man's first time. Mature, voluptuous, sexy Sylvia seduces her friend's son. The pitfall being he's her friend's son! Please send feedeback about any part you enjoy, or any part you don't. There may be errors that remain - forgive me if there are. Above all, I hope you enjoy. GA - David, Panama 20th March 2012 Th...

Wimp Loses to Young Black Boss

by michaelwimphusband on Sep 19, 2017
Interracial Love

A True Story. At the age of 49, Myron felt that he had reached a certain degree of success in both his professional and personal life. He had worked diligently throughout his academic and business careers to be in the position he now was. He had put the failures of his past love life far behind him, and he was now going on his 14th year with this corporat...