Shy Boy Stories

134,021 results
Orientation
Length
Source
Infinite Scroll

Wife's Massage Voyeur Ch. 04

by gonzi2 on Sep 19, 2017
Exhibitionist & Voyeur

My normally shy wife Carol had reluctantly taken over my male massage clients after I’d been crippled from the waist down. Being jealous I drilled a spy hole to watch her and after weeks of straightforward massages a client exposed himself to her and asked for a hand job, which she refused. But our finances were so bad she obliged him the next time. Amazin...

His Black Master Ch. 02

by NickJBella on Sep 19, 2017
Interracial Love

Clarence & Nora McMahon were thrilled to give birth to their son Kevin. Nora had several miscarriages and was told she would never give birth. Kevin was born premature and spent most of his youth in and out of the hospital. He was home schooled and eventually graduated from a private high school. Nora was very protective of Kevin and he was very shy and d...

Shy Young Mistress

by hampshiresub on Sep 17, 2017
BDSM

Carrie was 18, and the most shy girl I had ever known, but also behind that shyness, as kinky and dirty as anyone I had chatted to. For the last few months she had been coming out of her shell more to me online, and had become my Mistress, and we were due to meet for the first time. It was not the first time we had been due to meet, but the previous times he...

Sunday Morning Pt. 03

by fadedgiant on Sep 14, 2017
Romance

This is the third installment of the continuing story of young love between Abbie and David. Things couldn't be much better, yet much better they will get. ***** The next two weeks were filled with college preparations. Abbie was about to enter her first year of college and David was an upperclassman going into his third year. They were virtually inseparab...

The Next Step

by peterpecker on Sep 26, 2017
Romance

The story is set in the south of France. Part I has already been published on this site as "Vineyard Adventures". My father and I were turning bottles of wine in their racks in the vineyard's cellar. He said to me, "I'm glad Martine is becoming more at ease around you, Pierre." I glanced at him, wondering if there was any hidden meaning in his statement,...

Spin the Bottle

by Poker1 on Sep 12, 2017
First Time

It was getting late and Sarah was frantically trying on different outfits in her bedroom. She kept tossing clothes to the corner of the room and cursing not finding anything suitable. She had been looking forwards to this night for weeks because she would be soon arriving at her best friend, Amy's house, for a Halloween party. Amy's parents were much more...

Spin the Bottle Party

by Poker1 on Sep 12, 2017
First Time

It was getting late and Sarah was frantically trying on different outfits in her bedroom. She kept tossing clothes to the corner of the room and cursing not finding anything suitable. She had been looking forwards to this night for weeks because she would be soon arriving at her best friend, Amy's house, for a Halloween party. Amy's parents were much more...

Village Ch. 03: The Party

by Stanlow on Jun 18, 2018
Erotic Couplings

The party was at the Manor House, this was in the centre of the village, next to the church. It was a large rambling Victorian house, in large grounds and was owned by an elderly couple, Mr and Mrs Perry. The house in the twenties, when they were young, was filled with a large family, they missed that, so allowed the house to be used for a party for the scho...

My Shy Neighbour

by Ozgal on Sep 14, 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...

Sister Agnes Takes Charge

by Codis on Sep 13, 2017
Mature

There are never any secrets. Not ever. Not in a large or small community. People are spies by nature. Sister Agnes had caught Father Pete having sex with Meggan. It was their sin and didn't Jesus die for all our sins? Weren't they all washed away by His blood? Sister Agnes younger sister had gotten married to a young strong bull of a Lithuanian, a police o...