Shy Boy Stories

134,021 results
Orientation
Length
Source
Infinite Scroll

My Shy Neighbor

by Ozgal2 on Sep 17, 2017
BDSM

Marty was such a sweet guy, but so painfully shy. He’d moved in next-door 3 months ago and in all that time had uttered no more than a couple of words and only when I spoke to him first. He had this cute little way of dipping his head into his shoulder and never making eye contact. Marty was quite a handsome man. He was about 6’ tall, with dark blonde hair...

Sprite-Snowdrop Tales Ch. 07

by Michael142 on Sep 11, 2017
Sci-Fi & Fantasy

Acknowledgement: I wish to express thanks to KJPlotts, for her professional review and edit of this Story. Michael142 ***** Chapter Seven - A Visit to the Fairy's Village: Jasmine returned to her village full of tales about her new friends among the water sprites. She kept her promise not reveal the location of Snowdrop's secret pond. The other girl fa...

Lady Sheffiels's Chess Match

by rattails on Sep 17, 2017
BDSM

Lady Charlotte Sheffield enjoyed watching chess matches while she took her afternoon tea. Not that Charlotte was an intellectual snob. Not at all. You see her chess matches were conducted to satisfy her erotic fetish; to see two men trying to concentrate under the most trying of conditions. Competency at the game was of course important, but equally so was s...

School Daze

by Croony on Dec 29, 2017
Fetish

Abbottsford College, situated in the City of London, was a prestigious all boys finishing school that catered for teenagers from the age of sixteen to eighteen. The pupils were mainly from rich and titled families who wanted their sons to experience the strict regime and make them into better adults. David Bryden was the headmaster that dealt with disciplin...

Fun with Soldier Boy and Friend

by BritPop on Aug 31, 2017
Group Sex

"Brett's in town. He needs a place to stay for a while." My boyfriend's voice interrupted my thoughts as I lingered over my cup of coffee. "Ummm? Brett?" "You remember. Tall, dark, handsome and shy. All the girls loved him...," grinned Mark. I did remember now. Mark's handsome, rather shy friend. He had joined the army, becoming even more of a heart throb in...

Lynn and Leif Forevermore Ch. 01

by mich80new on Sep 14, 2017
Interracial Love

Leif fell in love with Lynne from the instant he saw her. Singing, almost alone, in a crowded bar, with creamy beige skin, and soft brown hair which she wore shoulder length. There was a different quality to her, almost ethereal. She was a cute, petite black girl, with great legs, and a wonderful ass. But that wasn't what attracted him to her initially. It w...

Brighton Hairy 1st Round

by belab on Aug 18, 2017
Fetish

This is a story of the early sixties when I was a young boy in London. I was just out of my teens, painfully shy and ordinary looking. The one thing that literally stood out was my exceptionally massive penis. I am small built just over five feet six inches tall but no underwear is big enough to hide my huge cock. The one time that I managed to entangle with...

The Camera

by GradStudent on Aug 19, 2017
Exhibitionist & Voyeur

I finally chose an Ivory fabric softener box from the laundry. I did not think anybody would notice it sitting on the shelf in the bathroom. The camera fitted nicely. The camera was very fancy, motion sensor, auto focus, and even had a mode for automatic, 820.11b transmission to my laptop. But the pictures were also stored on the camera. Cynthia and Carol...

One Step Too Far Ch. 03

by LanaChu123 on Dec 9, 2019
Transgender & Crossdressers

"Lana... Lana..." "Lana?" My eyes fluttered open sleepily. Ms Garvey calling out to me as she undid my foot bindings with the wrist bindings already undone by either side of the bed. I rubbed my wrists and could see the hosiery ripped where bindings had been at my feet. "Sorry to wake you up but I think it is better to get on a schedule." I sat up cross-le...

Sunday Morning Pt. 01

by fadedgiant on Sep 14, 2017
Romance

This is part one of at least a two part submission. In this episode, the first person perspective is that of Mr Adams. The plan is part two will be from the perspective of the young David as his romance with Abbie continues. ***** Early Sunday morning. I sit naked watching the sun rise over the small lake. Next to me lies someone who only recently entered...