Gay Chastity Stories

28,507 results
Orientation
Length
Source
Infinite Scroll

Letter from Tulsa

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: Kenyon and I walk along the beach as we vacation in California. It is not really a nude beach, just a clothing optional beach, and Keni has optioned that I walk naked, except for my chastity piercing, and she is wearing a pale blue bikini, to which her curves are magnificently displayed. I am in a bit of pain. I put regular milk in her co...

Caught in a New Life Pt. 02

by Fibaro on Jun 15, 2020
Transgender & Crossdressers

(Hello everyone, here is part 2 of the story requested by one of my readers.) Chapter 3 While Monroe was having breakfast the next morning Lena passed by on her way out wearing a white body con designer dress with a black belt at the waist, black sheer pantyhose, a pair of white patent leather heels, big rounded sunglasses and a wide floppy white hat with...

The Greatest Knight Of Your Life!

by MeganOckers on Jun 9, 2020
Humor & Satire

The Knight in Shining Armour/damsel in distress is a highly rated lockdown role play. But shining armour is hard to come by in these Covidinous times unless you're a member of the landed gentry or a scrap metal merchant. Also, when you visit a stately home have you noticed how small most of the suits of armour are? This is due to the multiple orgasms, sorr...

Always Read Before You Sign Ch. 02

by Reaver90 on Apr 6, 2020
Transgender & Crossdressers

Sam stood outside Miss Turner's front door. The weekend was hell was for him. He couldn't sleep, he had to sit down on the toilet and pee like a girl and more importantly, he couldn't jack off. The young man feared what the beautiful woman but deadly woman had in store for him. He took a heavy breath and knocked on the door. He waited for a few seconds as t...

Connie Throws a Party

by cmorehead on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. In a previous story, I described some of the kinky activities enjoyed by my boyfrie...

The Setup

by alexyzia on Sep 13, 2017
Transsexuals & Crossdressers

A "true" account of femdom, reluctant coerced-bi and (mild)cross-dressing/TV, blackmail, and permanent humiliating service to a very manipulative ex-girlfriend, all leading up to a total reprogramming and gracious acceptance of my destiny. PART 1 So my ex-girlfriend Jessica dumped me recently and said that the only way that she'd even consider taking me ba...

It Started Innocently Enough

by thremuff on Sep 17, 2017
BDSM

It started innocently enough. Well, not really. Brett and I had been friends since high school. Never really romantically involved though. After college we both found ourselves in careers while most of our friends were married and started families. We were spending more time with each other. Again, not in a romantic sense. Both of us dated, Brett more than m...

Paige and Spalding

by justincbenedict on Jul 4, 2018
BDSM

Dear Mom, Thanks for the lemon bars. It'll help me stay awake during my property class. Tell Rylie that I'll bring back her mohair coat, don't have a cow. So you were asking me about how things are going with Spalding. I was so glad you and Dad liked him when you came up to school. I agree he's cute and has a good sense of humor, and Dad said Spal was obv...

The Spirit of Lady Macbeth Pt. 07

by alyssawinters on Oct 19, 2020
Transgender & Crossdressers

The campus still empty for holiday Tracy his backpack replaced with a catch-all purse walked across the quad gripping the strap looking to kill some time reading before returning to home and Mistress Lisbeth. Spotting the couch in the near empty coffee house he planted down in the middle of it ready to open his book of Shakespeare's 'the Tempest'. Nervous...

As Journey to Janet Pt. 03

by jamtby on Aug 13, 2019
Transgender & Crossdressers

"Janet, I want you to listen to me very carefully. You will become the person you were meant to become tonight." Beth's slow, hypnotic voice seemed to penetrate my being. Still exhausted from my orgasm, her words touched me in a way that no one had ever been able to reach me. Beth began, "Janet, you are a beautiful woman and for too many years you were caug...