Shy Boy Stories

134,021 results
Orientation
Length
Source
Infinite Scroll

Shy Wife Exposed

by ttlvr on Sep 26, 2017
Exhibitionist & Voyeur

I met my wife, Jessica, when we were in high school. She was, and is, young, petite and beautiful. She remains into sports and now, even at 32 retains her smooth athletes body. Despite what I consider to be a flawless body, she is painfully shy, dressing conservatively, even at the beach. Now don't get me wrong, she will go out in a swimsuit, but she always...

The Tutor and Her Student Pt. 01

by myboyfriendthewhore on Mar 26, 2019
Erotic Couplings

I'm a 37 year old office worker by day, and a maths tutor by night. I prefer my evening job: it supplements my income and I find it rewarding helping students learn in the run up to their A Levels. I teach 18 year olds, who tend to want to learn quickly. I work most evenings, particularly at this time of year, with A Levels just a couple of months away. La...

19 Cute Kiss Scenes (Role Reversal)

by CuteAndLovelyYetHorny on Oct 31, 2018
Romance

Author's note 19 super sweet little stories of a few hundred words about a cute kiss done by / given to a good boy or the lovely girl that takes care of him! :3. Inspired from a picture I saw online that was simply a handwritten listing of those kisses! They are more or less SFW, those who aren't aren't about sex scenes either. If you don't know the...

Kinky Jenny Ch. 02

by skinnypom on Sep 1, 2017
Group Sex

All characters in this story are over 18 years of age. ******* "I've got a special surprise for your birthday Friday." "Yeah? Oh thanks love, something to look forward to." "A threesome." "Not a surprise anymore is it?" "I guess not. But the work experience girl Tasha at work told me she saw your picture on my Facebook and thought you looked quite sex...

Heavenly Woman Made Me Cum Helpless

by CuteBabyBoy on Sep 12, 2017
Fetish

This Story is so precious to me. I worship all women as superior to me. I'm a skinny cute looking boy; and I went over to a strip club and this was as usual, I was so nervous, shy and also my baby penis throbbing and dripping with cum. I went in and took a seat, asked for a bottle of water and just looked around. I noticed a well built lady who was unbelieva...

German Nude Sauna

by ChrisEva on Dec 24, 2019
Erotic Couplings

The atrium was beautiful, it was true, but she couldn't appreciate it. The tingles of uncertainty that began in her stomach on the bus ride down from the hills had spread into a full-body tension. A momentary feeling of faintness wafted up to her head and she realized she hadn't been breathing; a place to sit down for a moment would be a wise choice. The res...

Helpless - His First Time

by MissRileySapphire on Sep 25, 2017
BDSM

We were sitting on the edge of her bed, fingers laced, both staring out into the night sky over the city. It was awkward at first, sitting with her on her bed, but awkward silence quickly turned into lustful energy as soon as I heard her tender voice. What had started as a semi-casual conversation about sex had turned into a heated exploration of kinky desir...

Am I Jealous? Ch. 03

by iuandwe on Sep 15, 2017
Loving Wives

I looked at Vikash; his smile was from ear to ear. He looked towards Sunehra and then after a while looked down in shyness. I looked at Sunehra and saw her looking at him. Then she looked at me and we smiled. I left them there and went to the toilet to wash myself. I was almost done when Sunehra entered the toilet. I didn't lock the door as we fucked in fro...

DIY Teens Ch. 01

by Mag58 on Sep 19, 2017
Toys & Masturbation

I had been a bit of a frumpy chubby girl, but as happens sometimes, I suddenly blossomed soon after my 18th birthday in 1975 and grew three inches taller in four months. I was still no model but I caught the eyes of a few boys on the beach in Great Yarmouth during our Summer holidays and even let one boy feel my enormous new boobs on the last night. I had a...

Rayne Ch. 03

by Undercoverwriter on Sep 19, 2017
Romance

Stevie felt all warm and comfy as he hovered in that place between sleep and wakefulness. His head ached but the softness his head rested on made it feel much better. As Stevie slowly opened his eyes his vision was a bit blurred but it almost seemed like he was in a pink room. He blinked a couple of times to clear his vision and when it was fully restored he...