Crossdressing Punishment Stories

32,309 results
Orientation
Length
Source
Infinite Scroll

Playday

by babycuddlebunny on Oct 8, 2019
Fetish

Daddy has me tied up in the playroom today. He is working on an important project from home and says I need to be accessible for stress relief. I'm lying on our special bench- naked of course- with my wrists and legs up for easy access. I've been here for a while now, I'm not sure how long. I just love to be a good girl for Daddy! He fed me lots of water bef...

Letter from Grand Island

by justincbenedict on Sep 24, 2019
Sci-Fi & Fantasy

Dear Shoeblossom, As an artist of sorts, I remember reading that the writer William Burroughs spent his final years, after his debacles in New York and Tangier, in very quiet Lawrence, Kansas. It wasn't as exciting as Mexico, where he'd shot Mrs. Burroughs' head off while playing "William Tell" with a martini glass so precariously placed...but it was time...

Meridiana Pt. 02

by Tangledskein on Nov 18, 2019
NonHuman

"BUGGERY, BUGGERY, DAMNATION, AND FUCK! FUCK, FUCK ALL HUMANS!" Aka Manah, high demon of the Realms of Darkness and General of the armies of Buiti; recent victor of the battles of Akatosh and defeater of Zarathustra's hordes, picked up the glowing "orb of sight" and threw it, not caring where it went. The orb smashed into the head of a minor demon and stave...

Lady Orenthia

by justincbenedict on Jul 17, 2019
BDSM

Auden shook hands with his manager. "It was a great crowd tonight, Auden." Hal said. "Remember, you have to meet with Tusselbaum for the scoring tomorrow. You have composed-" "Yes, of course. Don't worry about it, Hal." Auden was thrilled to be doing the music for an actual movie. He enjoyed his work with the Buttermilk Falls Philharmonic and the CDs he'd...

100 Centimetres - Experience 04.2

by icefantasygirl on Jan 1, 2019
BDSM

Authors Note Thanks once again for all your support. I didn't have the time to write this experience as one story thus it's two parts. Hope you enjoy! Ice ~ The Ice Fantasy continues... Ecstasy. Eternal Bliss. Fireworks. That's what I was expecting to feel but it didn't eventuate. No, you had something more cruel, more sinister, more dominating in mind....

Lace, Gag and Anal for Him Pt. 02

by DirtyLonelySlut on Apr 3, 2019
BDSM

As I stand, my juices dripping and sticking between my thighs, my hands tied behind me, naked and at his mercy, he stares at me and smiles. "Please Sir, can I taste your cock?" I whisper quietly. I want him so badly, to taste him, feel his throbbing cock fill my mouth, push down the back of my throat. To kneel and swallow his cum with my hands tied away. H...

Bits of Bondage

by ropucha on Apr 24, 2019
BDSM

The Pendant He stepped by her and placed the small lock pendant around her neck. After he latched it and stepped away, she turned and dutifully lifted her skirt, hooked the thin thong panties with her thumbs and dropped them to the floor. He lifted her skirt and swatted her firm, round cheeks. A sign he approved of her knowing the rules, but also a small pu...

Tease

by Maaya2000 on May 28, 2019
Exhibitionist & Voyeur

I was alone in my flat which is on 5th floor, that cool breeze and a little sun rays were peeking through windows. In hall there was a window of glass joining balcony. I was a little turned on and being alone at home was a chance to play with myself. Taking in consideration that opportunity, I wore a sexy see through black lingerie and black high heels. Wi...

Pretty Little Slut Ch. 03

by Steve1980 on Jun 3, 2019
Fetish

I was a little worried about my new role as Beth's "lesbian slut". Things had escalated quite quickly from her dressing me in panties and a camisole to her ass-fucking me with a dildo. At this rate, I wasn't sure what could happen next. The last encounter was last night. I was physically okay, but had spent the morning crying about my lack of control over t...

Mistress Chloe and Adrianne Palicki

by CaptainNinnin on Jan 16, 2019
Celebrities & Fan Fiction

Adrianne drove up to Chloe Bennet's house upset with her manager for keeping her for so long on THIS day of all days. She had been emailing Chloe in secret for the past two months. She had fallen into a deep lust for Chloe ever since they worked together on Agents of S.H.I.E.L.D. But she never had the guts to tell her while they worked together but now that...