Strapon Boy Stories

106,036 results
Orientation
Length
Source
Infinite Scroll

The Bet reLoaded Ch. 01

by jomar on Sep 26, 2017
Fetish

I hope you enjoy the kink. ********** "Fuck!" Lilla flicked back her brilliant shoulder length red hair in that way women do and laughed. "Aww, poor baby." She set her coffee on the end table. "Not funny," I said. I was sore that I had lost our latest bet and a little afraid of what she had in store. "Is too," Lilla said and straddled me. I was sitting...

A Slave under Contract Ch. 01-03

by gynarchite on Jul 18, 2018
Sci-Fi & Fantasy

Chapter 1 – I sell myself Sitting on the monorail, looking at my reflection in the window and ignoring the city as it sped by, I told myself it would only be for three months. Three months wearing the collar, three months of almost no-holds barred slavery. The credits would get me out of the hole I'd dug for myself, and then I could book passage off this ma...

A Dickgirl's Birthday Present

by sajukno on Sep 19, 2017
Transsexuals & Crossdressers

"Happy birthday, Ann!" Charlene presented her long-time girlfriend, Ann, with a beautifully wrapped present. The two had been together since they were both freshmen in college. Ann was drawn to Charlene's beautiful smile and her wit. At first, Charlene hadn't been very receptive of Ann's overtures, but after a spontaneous drunken fling, Charlene had fallen...

Sam's Story Pt. 03

by Shadykingcolor on Jul 29, 2019
BDSM

Editor's note: this story contains scenes of incest or incest content. ***** I awoke the next morning to my cock trying to break free from it's cage. As I started to move I realised Mel was laying across my chest. As I laid there I pondered my predicament. Last night I wanted out of the cage, Mel asked me to wait. She also changed her mind and NOW wants...

The Phone Call

by whipped31 on Sep 17, 2017
BDSM

"Hello?" I said as I picked up the phone. "Hey Max, it's Jessie." Jessica Burns was one of my closest friends. We had met in high school and became closer friends when we both attended state university. "Hey Jessie. How was your therapy session today?" Two months back Jessie had been raped in a parking garage. She was going to unlock her car when someone j...

Doctor’s Visit

by LonelyLez on May 6, 2020
Fetish

All characters who engage in sex are 18 years old or older. Feel free to comment with any requests/ideas. Hope you enjoy. ——————————————————————— Daniel Cross sat in the waiting room, his cheeks burning. The reason for his embarrassment was the fact that his mother was sitting in the chair next to him. “Mom,” he said exasperatedly, “I’m eighteen now, I don’t...

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Sissy for Mommy's Nipple Cream Ch. 05

by ppeaks42 on Nov 2, 2020
Transgender & Crossdressers

The evening after Jaime's doomed attempt at seducing Julia found the young sissy crying into her pillow as she tried to reconcile herself to the whirlwind of changes she'd gone through. Less than two months ago "Jaime" had been nothing but a shared figment of imagination, a character he dressed as for his regular breastfeedings with his mother. When he'd tri...

Training Him to Take Dick Ch. 03

by magic_tantra on Sep 25, 2017
Fetish

As soon as I drove home couldn't wait to try on my new dick! Going to the bedroom I strapped "cock" viewing myself in my full length mirror. The end inside my vagina felt so good inside me stimulating all the right places especially my G-Spot. As soon as I turned on the vibe I came. I was so horny I didn't hear the door open and Michael walk in on me. His ja...

I'm No Man, I'm Her Asian Bitchboy Ch. 02

by Veryrespectable on Feb 25, 2019
Fetish

The story so far: Anne is a beautiful and charismatic white woman living with her short, weak and submissive Asian boyfriend. Anne treats him as her "her cute Asian bimbo fucktoy." After he cums without properly asking for Anne's permission, Anne decides corrective measures are needed to remind him that he is no real man and that his role in life is to get...

Kellys Sex Toy

by teasedslut on Sep 17, 2017
BDSM

This was agonising. My Princess locked me up in a chastity belt almost a year ago, and has only let me out to edge and frustrate Her cock before locking it up again. Only problem is, I am so incredibly horny that almost ANY woman looks good. Even some guys, now that Princess has got me sucking Her boyfriends clean after She has fucked them. Now I have a huge...