Chastity Boy Stories

108,647 results
Orientation
Length
Source
Infinite Scroll

The Three Billy Goats Gruff Enough

by Violette on Sep 14, 2017
Humor & Satire

Lookee here now; I've got a little story for ya. It seems there was this troll, and he had himself a bangin' setup. He was a straight-pimpin' Mack Daddy with sharp clothes, gold chains, and a fine patch of riverside property. And you know how he got all of that? By having the finest ass you ever heard about! (Not HIS, stupid!) You see, player knew how to fi...

Long Wonderful Weekend

by Silentbob on Sep 13, 2017
Erotic Couplings

I was sitting at the airport waiting for Bill's plane to arrive. I couldn't wait till he got here to Philly! I came to the airport and I was waiting at the gate. My outfit consisted of a knee-length pleated black skirt and a white blouse that showed off my chest nicely. I had my red hair combed nice and neat. I sat down right where near the gate he was suppo...

Office Hours Ch. 05

by moxiesterra on Sep 14, 2017
BDSM

Coping with my denial was a little bit easier the following week. I was still horny as hell and still very much wanted to touch my pussy, but I was beginning to adjust with the fact that I didn't have permission. I suppose after enough time just about anything can start to seem normal, no matter how crazy it actually is. Still, I can't deny that I was despe...

Brian's Sleepwalking Adventure Pt. 07

by SirBosk1 on Sep 15, 2017
Novels and Novellas

This story is based on what may be an urban myth from my college days. A fraternity brother told me about the incident after my own adventure, described in my story "Pledge Class Payback" so I believe it to be true. When I asked about it, no one could remember the actual names or years or the fraternity. However, it fed my imagination and inspired me to writ...

Unleashed

by puzziboi on Sep 16, 2017
Transsexuals & Crossdressers

Ray stood up from the chair in the New Millennium African Braiding salon and checked his fresh cornrows in the lengthy wall mirror. He folded off three twenty dollar bills and told the attractive dark-skinned stylist from Ghana to keep the change. She had attempted on occasion to get the six-foot-four-inch, two hundred forty pound brother to get inside her p...

Every Summer Ch. 03

by dualwriter on Sep 14, 2017
Romance

Michelle checked on the little ones in the strollers before wondering to the back of the bus, patting heads, speaking to each of her children. They were all busy with books or games being very well behaved. Now that the bus had stopped the infant began waking. One of the older girls picked up the baby, kissed it then proceeded to lay it on the seat and chang...

Space Diary Year 3

by ROS_LOMBOT on Sep 17, 2017
Non-Erotic

Chapter III , Year 3, Cabin Boy (rank 0 merchant navy) Punch, Punch, Kick, Duck. "Cabin boy! Bloody cabin boy!" Duck, Leap, Kick, Kick. John and Lisa were sparring in the cargo bay. There was sweat galore despite the moisture drinking plants that grew along the walls. Between brief breathes the two spoke as they exchanged practice blows. "It is a step...

Retribution

by ValentineSatterlee on Sep 2, 2017
Erotic Horror

The Angel of Death sped on midnight wings as the dying rays of the setting sun disappeared upon the horizon behind her. Catching an updraft she was lifted effortlessly high above the city, giving her a better vantage point to locate her prey. The rooftops of the sprawling desert city were all beginning to look the same, but no matter, the man she was after w...

Joey Becomes JoJo

by polishjoe on Sep 13, 2017
Transsexuals & Crossdressers

I open the door and there stands MASTER ED, I bow and ask him to enter. He looks at me and laughs and says " You are a pathetic piece of worthless shit" then he goes over to Big Mama, my Mistress, and kisses her hard and hungry. I now know I am in for the worst weekend of my life, but I also realize it may be the best one too. The tape on the TV has finishe...

My First Ladyboy

by hornyrider on Sep 16, 2017
Transsexuals & Crossdressers

At 27 I reckoned I had the best job in the world. Twelve months ago I'd been appointed by the London-based international group I'd joined some five years before, to monitor the performance of our agents throughout the Far East from South Korea down to Indonesia and across to Thailand. No doubt one of the deciding factors in my appointment was that I was unat...