Crossdressing Punishment Stories

32,309 results
Orientation
Length
Source
Infinite Scroll

Auctioned Ch. 01

by Anonanonymous on Aug 19, 2017
Exhibitionist & Voyeur

***This is a true story*** "Any improvement on $5...going once, going twice, gone." I peeled off both soxes one at a time, balled them together and arced them into the corner of the room. "Now I'm trusting you, Eve. You put that fiver in the mail." 'You bet :-)' appeared in the textbox. So I left both bare feet up on the desktop, wiggling my toes, etc, fo...

Day 2

by Someonesfreak on Sep 17, 2017
BDSM

That night, after his little "show" of domination, he spent the next couple of hours making the slowest, sweetest love to me. He kissed, caressed, loved every single inch of my body. Then, I curled up in his arms and went to sleep, sleeping the best I've ever slept in my life. The next morning, I woke in the grips of fear. I was in a strange room, naked, t...

Chauffeur Driven Adventure

by CreativeUK on Sep 17, 2017
BDSM

When jane struggled to open her eyes the sun was streaming through her window and she realised with a start that she was alone. Memories of the previous night shocked her into wakefulness and she was very aware that both her cunt and arse felt well-used. It had started out normally enough - she had gone with her Master to have a quiet drink, but it appears...

My First Time, Their Slave Ch. 01

by a64and18 on Sep 17, 2017
BDSM

A year ago, when I'd just turned 18, I was out hanging with my friends at their favorite hookah bar. Sure I admit I had a good time with the guys, but I've been eyeing this woman since I got here. I always had two sexual fantasies that stood out more than others: messing around with older women, and bondage. I never told anyone, they'd all think I'm weird wa...

Morning Experience

by DadDomSeeksLTR on Sep 17, 2017
BDSM

The day began as any other in the past, the sun rose. The sun shone through the window. The sun's shimmering streaks showed off her sexy naked form and as always I was in awe of her. Irene slept hard after our session last night her body still tender from my pounded bottom. So, I decided Dad would get her breakfast going. I slip out of bed quietly and tiptoe...

A Night Out With Master

by exquisite_pet on Sep 12, 2017
BDSM

I was nervously waiting for You to come home. You had called earlier and said that we would be going out to dinner tonight. You were specific in what you wanted me to wear. You wanted me in the short black dress that was modest yet sexy. But I had not had a chance to pick it up from the dry cleaners. So I had to wear the other black dress. It was a bit more...

Always in Trouble

by razorshift on Sep 17, 2017
BDSM

Hello readers! Please note that this is my first real story, so forgive me if there's a stupid mistake some place or another. All kinds of criticism are welcome. This is the first part of a multi-part story, I'll continue if I find enough support. It's going to build slowly, this part doesn't contain much smut. Also note that it contains, or at least comes n...

Tonight

by eclipseofurheart on Sep 17, 2017
BDSM

Tonight. The word sends shivers down my spine. Tonight is when the pleasure begins for me and for my Master. I yearn for it and can feel every cell in my body vibrating from the strain of holding me earth bound. Every muscle vibrating from consciously willing them to stop tensing and coiling. It's as if I'm ready to jump from my skin and spread my arms and...

Lady Hipnaughtyk

by Hipnaughtyk on Sep 17, 2017
BDSM

Your moves were fluid and I enjoyed watching your hips moving languidly as smooth as wine being poured out into a glass. You peeked at me a few times, curious to see if I was watching you from my perch and the satisfied look on my face when we locked eyes told you everything you needed to know. I held my drink to my lips, sipping now and then, the sweet liq...

Need

by EnergyEntitles on Sep 17, 2017
BDSM

She screamed, knowing it to be a futile effort. He had her. She wanted this, but she also wanted the struggle. So she let the rope rub her wrists raw and she vainly tried to free herself from the bed. He stood just above the bed watching her struggle. He smiled, he loved this as much as she did. He was a foreman on the controversial tunnel project and alwa...