Chastity Boy Stories

108,647 results
Orientation
Length
Source
Infinite Scroll

Come Sail Away With Me

by robertreams on Sep 13, 2017
Romance

Chastity, in a long, elegant evening dress of deep green satin, whirled around the dance floor with one man after another, thoroughly enjoying the swishing sound the dress made, the way it contrasted with her flaming hair. She was the official hostess of this dinner party. Since her mother had died four years earlier, when Chastity was only fifteen, Chastity...

Financially Dominated and Cuckolded

by johan26 on Sep 12, 2017
Fetish

This is a story about a woman cuckolding a man and taking all his money - don't read if that doesn't interest you! ***** I first met Kristin on a Saturday night at a trendy bar in my city. She was cute, around 28 with dirty blonde hair, and a sexy blue dress on. I'm 33. We hit it off and I bought her several drinks throughout the night. I thought I might b...

Letter From Tacoma

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: When my husband, who is owner and ringmaster of the Epic Circus, comes into our hotel room (We, thankfully, don't have to live in the circus trailers) I'm ready for him. He lays the whip down, and then it's my turn... "Strip it all off Apollo, my love! Now you'll get a nice thrashing....it's MY turn to use the whip!" Sometimes after th...

The Palmist Ch. 08

by PeterOmez on Sep 16, 2017
BDSM

AUTHOR'S NOTE: Everyone in this story is at least 19 years of age. ***** On Sunday Derek and I both called Lila and we all talked on speaker. Lila was thrilled to hear everything that had happened the last two nights and how Ashley had been made aware of my "bitch boy" role. At one point she said to me, "You rrrrreallly like Ashley, don't you?" "Yes, ma'a...

A Trip to a Clothing Optional Beach

by DanLockered on Sep 1, 2017
Fetish

A large rowing boat approached the shore. It had been rowed from the yacht in the distance. 8 large males glistening with sweat manning the oars. In the centre of the row boat sat what looked like a lady pirate administering a riding crop to the rowers. In front of her a smaller male obviously sitting on the floor of the boat was fanning the lady as she exer...

The Sexy Cuckold Couple Pt. 07

by cuckcpl4play on Sep 19, 2017
Loving Wives

The Day of the Ceremony is Finally Here Part 7 As I drove home from work, I could not stop thinking about how our lives as slave and slut had escalated so quickly. What felt like days ago, I was a powerful executive about to obtain my new and even more respected position, but instead I was driving home soaked in my colleagues urine as the new office demoral...

Road Dog

by TwistedPanties on Mar 3, 2020
Erotic Horror

It all started with a bit of fun on his road trip. Bryan was en route to San Francisco to hang out with an old female work colleague, as "friends". She was a couple years older than him, 32 to his 29, and she had a great apartment downtown. Of course Bryan had wondered if she would let him put the moves on. It didn't matter if he got to hookup with her or n...

Weekend Discipline

by amypussy on Sep 18, 2017
Fetish

"Oh please Anna! Please, please?" My husband Dan pleads with me. We have been playing various games, for some time. We both enjoy Dan's desire to be submissive. Every Friday night Dan comes home from work, and for the entire weekend, he goes along with various humiliations. He seems to be very tolerant. When ever I think I'm being too severe, he reveals la...

Mistress Katie Supervises Ch. 03

by royalrogue on Sep 18, 2017
Fetish

Michael was mowing the lawn when she called. Slowly he had been crossing the small lawn, pushing the mower at comfortable pace chosen to avoid sweating too much in the warm summer afternoon heat. The quiet mower whirred, clipping the few grass blades that had grown tall enough to reach its rotating blades. Luckily, the mower did not prevent him from hearing...

The Evolution of a Femdom Marriage

by herpantyboy on Sep 18, 2017
BDSM

I woke up this morning and realized that I'm living in a femdom marriage, that the fantasies I've had in years past are now a very real situation happening right now. I look down at my waist and slowly put a hand under the waist band, then pull down and notice a pair of black panties with pink lace covering the little bulge of my dick in the silicon chastity...