Strapon Chastity Stories

8,434 results
Orientation
Length
Source
Infinite Scroll

Jason's Secrets Exposed Ch. 04

by jlenil on Sep 14, 2017
BDSM

The following morning, shortly after breakfast, I got a text from Marilyn. "You were 100 percent right-last night was awesome," she said. I smiled to myself and replied, "You can fill me in on the details later. It can get even better if you want it to, my dear sister-in-law." I went out to the patio to smoke my morning cigar. Jason, kneeling, presented me...

The Vault Pt. 09-10

by undherfoot on Sep 12, 2018
BDSM

Part 9 I turned my head and I could barely see Caitlin out of the corner of my eye. She took her right hand and put it under my hip and pulled it up slightly. I raised my hips just a bit so that most of my torso was still on the mattress but there was now a slight distance between my hips and the bed. I felt the cold of the lube as she squirted some into t...

The Moral Slavery Ammendment Ch. 05

by Vslave on Apr 21, 2020
BDSM

Evan came up to the stage to collect us, attaching a leash to each of our collars and giving Mistress a signed check before leading us off of the stage. Mistress seemed annoyed on our behalf once she recognized him as the boy insistent on fucking Eve. Now he would get his wish. He waited for us to exit the theater and emerge in front of some busy crowds be...

Chastity Mansion Ch. 04

by Shavvy3100 on Nov 5, 2018
BDSM

Thanks for your patience for chapter 4. I must admit this was the most exciting chapter I wrote and that's mainly because I've co-written this with Ms Lauren and Ms Sweets did the proofreading. They're both amazing Women, such a shame They both live far away from me. Anyway, I hope you all enjoy this chapter too. ***** Someone is whispering in my ear: "co...

My Father, The Maid Ch. 02

by SissyOona on Oct 30, 2018
Transgender & Crossdressers

I awoke the next morning fairly early. My sleep had not been as restful as I would have hoped due to the revelations of the previous day. Eventually I pulled myself away from the supreme comfort of the bed and stumbled to the bathroom to take care of my morning business. As I exited the bathroom I could hear the sounds of breakfast being made from the kitche...

Danni Ch. 03

by Coder3445 on Apr 21, 2020
Transgender & Crossdressers

Authors note I know it's been a few months since the last Danni came out and I am sorry for making those who want to read wait for so long. With that being said the reason for it is that I meant to write it but suffered from writers block at the time and eventually forgot about it. However I hope this does Justice as I tried to make it longer without sacrifi...

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...

Women Enjoying Naked Men Ch. 03

by escriterra on Sep 13, 2017
Fetish

The muscles in her hips she had pressed into use as she fucked fantasy-Darrian the night before were actually sore the next morning as Taryn went through her gym routine. It was a delicious soreness. She looked forward to exercising those muscles so they wouldn't be sore. Taryn was ready. She just couldn't find a guy to peg. So it was good ol' dependab...

Jeff Explores His Fantasies Pt. 04

by majorpayne_1342 on Apr 13, 2020
Transgender & Crossdressers

For most of my life, I was always the shy kid. I barely had any friends. So experiencing everything I had this past week filled the void I had inside. I spent most of my birthdays alone and hardly received any gifts. This year, however, was going to be different. I never expected to receive the gifts I was given that year. First, taking things further with R...

Locked for Love

by bodman54 on Sep 17, 2017
BDSM

Tell me what you think. This one honestly got away from me because I wanted to keep it as one story but it just kept getting longer. * I stretched sleepily and looked around. The waves crashed along the shore and the sun beat down from a cloudless sky. I was stretched out in a beach chair and all my friends were likewise sleeping on various chairs and blan...