Strapon Chastity Stories

8,434 results
Orientation
Length
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Infinite Scroll

Penis Shrinking from Chastity

by tinywhiteboi on Sep 19, 2017
BDSM

After losing my wife to her big dicked black lover I was pretty depressed. I knew that my 4 inch skinny penis was not big enough to satisfy any experienced women. Sure it was fine as a teenager fucking young girls, but in my mid thirties I figured pussy for me was likely to be rare. While reading pornography on the web I discovered stories about small penis...

Chastised, Feminized, Sodomized

by Stefani on Sep 25, 2017
BDSM

My name is Kim Lee. I am half Korean and half Chinese. My first name got me teased quite a bit when I was in school. Nor did it help that I am a bit small and slender. Consequently I grew up rather shy and reserved. I never really had many girlfriends, as most women that I ever met seemed to prefer bigger, more macho guys. So I was not prepared at all when I...

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...

BDSM by the Book

by Stefani on Sep 11, 2017
BDSM

I was rather slow when it came to dating. My love life moved at glacial speed until I met my wife. In high school I was skinny and too short to be any good at sports. At school and in the town I grew up in outside Sioux City, I got pushed around a lot by other boys, all of which translated into a lack of confidence. Particularly around women. When I got to...

Becoming Hers Ch. 07

by fpat97 on Nov 6, 2017
Fetish

After five days locked up, Alex wasn't sure how he was going to handle this. Last week, Karen had made him cum and eat it every night as punishment and this week his body was still expecting that treatment. Plus, he was supposed to edge himself every day in the shower! The first few days weren't so bad, but now getting back into his cage was a challenge. He...

Careful What You Wish For Pt. 04

by Switch90 on Sep 25, 2017
BDSM

Shane laid in bed, completely exhausted from hours of endless teasing. Michelle had iced down his cock, still barely being able to contain it in chastity. "I'm sorry that you made me lock you up slave. I was really enjoying using My cock." "Please. Please unlock me. Please use me some more. Please let me fuck you! You're driving me crazy!" "I know." Sh...

Crystal: A Sissy Set Free Pt. 03

by InSpectrum on Sep 16, 2017
Transsexuals & Crossdressers

This is a direct continuation from Parts 1 and 2. You should probably read those first, if you haven't already. ***** Before he could think Ryan was gone, Crystal shut the toilet seat re-locked the door and sat down feeling a jolt from his plug, He suddenly felt very uncomfortable, his feet ached from dancing in ridiculous heels, his corset was way too ti...

Be My Slaveboy

by gynarchite on Dec 10, 2018
Sci-Fi & Fantasy

A very short story in the same universe as A Slave Under Contract "I think it's time we take our relationship to the next level, Robert," said Amy as she lay on her bed, stroking her bound, naked boyfriend's flank while she looked into his eyes. She had thought it would be quite interesting to date a free male for a change, but like most women on her plan...

The Matriarch – Ladies’ Night

by AMurphyWriting on Apr 13, 2020
BDSM

Granted, every night was ladies' night at The Matriarch. It's to be expected from a club designed around a femdom lifestyle. There had never been a guys' night, and there never would be. That isn't to say the male "employees" didn't enjoy ladies' night too. While I had never been informed of how pricing works for the clientele, it was apparent to me that t...

Property of the Elven Princesses

by gynarchite on Apr 25, 2018
Sci-Fi & Fantasy

Chapter 1 -- Taken From her golden throne, the Queen Ada of the elves surveyed her domain. To either side of her sat her adopted daughters, Princess Elvira and Princess Adria. As had been their way since their very creation, the elves did not produce offspring of their own. Rather, they took humans from their world and transported them into the different e...