Shy Boy Stories

134,021 results
Orientation
Length
Source
Infinite Scroll

Steve and Mrs. Carin

by RedBaron60 on Dec 25, 2018
First Time

Kitty Carin, 54, had been divorced for 12 years, leaving her as a single mom to her son, Colin, who was 18 and about to graduate high school. She worked out regularly and was proud that it showed in her figure. She was a classic brunette, 5'2" and about 110, and especially proud of her 34DD bust, which drew plenty of looks from men. Kitty's ex-husband was a...

Moriah Teaches Sex Ed

by MarahMoriah on Sep 17, 2017
BDSM

The alarm clock went off and James reached across the bed in exhaustion from last night's exploits. Moriah twitched and moaned in her sleep, her body begging her not to get up. James shook Moriah awake after waiting five minutes. "Honey, it's time to get up. Today's the big day, and you are going to be late if you wait any longer." Moriah growled and lifte...

Rear View Mirror

by KingofCucks on Sep 17, 2017
Loving Wives

This story involves the following; non-humiliating cuckolding, voyeurism and exhibitionism, swinging and MILF/student sex. *** The back area of the bar's parking lot was deserted as I swung the car around and found as unobtrusive a spot that I could before turning off the engine. The street light a few yards down provided just enough illumination withou...

A Virgin released from Chastity

by ronron1818 on Nov 16, 2020
Fetish

It was time to move on... I will be graduating today, 4 years after moving in with Ruth, and tomorrow, I will be moving out to start my life as a grown up. I already found a job in my home town, and rented a small apartment near the new office place. Ruth came with me and my parents to the graduation event. My parents liked her a lot. For them, it was lik...

Tall Beautiful Woman Made Me Cum

by CuteBabyBoy on Sep 15, 2017
Fetish

Tall Beautiful Woman - She Made me cum in my Pants This is a great experience for me, it was like an adventure. I was living alone in Chicago, for my job. I always admire tall, beautiful women, and well built (That is important to me). In my opinion these women are much superior to even all men. They are goddesses. I'm dripping in my shorts as I'm writing t...

Ellie

by BeMyPet on Sep 2, 2017
Erotic Couplings

Ellie and I became lovers when we were freshmen in college. She was this small, slight little goth girl, with waist-length straight black hair and flowing black dresses. Her smile was a Mona Lisa thing, fuzzy at the edges and hinting as something naughty. She rarely spoke but often stared, and it was this staring that originally caught my attention. We had a...

Angel in the Night 01

by ReefBeach on Sep 12, 2017
First Time

I'm new to this, so comments are welcome! I lay on my back on the bed, stroking slowly. I thought of the sexy, unapproachable girls on the beach. I thought of their pert breasts in bikini tops with the nipples showing through (nice effect in the cold seawater). The wet fabric clung to their bottoms, and even showed their pussies if you got the chance to be...

Theirs -Collared

by shyone71 on Sep 17, 2017
BDSM

I'd done it. Sucked Master's cock and swallowed His cum, sharing it in a kiss with Mistress and finally swallowing it down. I imagined I could feel it inside, like a warm, glowing liquid ball of light. Settling back on my heels, hands clasped behind my back, I bowed my head down and said, "Thank You, Master." Placing His hands on either side of my face and...

The Bastard Ch. 01

by H. Jekyll on Sep 14, 2017
Novels and Novellas

Chapter 1 : The Game I saw her again today, just this evening. It's a small world, I know, especially our little world, but that's twice now, in a week. If I didn't know better, I'd think she was setting them up, going to places she thinks I'll be, but I do know better. She can't stand me. I tried not to look at her, or even to notice her too much. I can...

Calendar Girl

by antony4127 on Aug 30, 2017
Exhibitionist & Voyeur

As Susan waited nervously for the photographer to open the studio door, she wondered how the hell Jayne had persuaded her to model for the charity calendar that the girls at the nursing home were putting together. "Don't be such a prude" she had said. "Just turn up in your nurses uniform and you'll be out before you know it." Then she had scowled at Susan's...