Crossdressing Punishment Stories

32,309 results
Orientation
Length
Source
Infinite Scroll

The Threesome Becomes Four

by Celticredneck on Feb 25, 2019
BDSM

Our little trysts with Master continued for quite awhile and we all grew quite comfortable with each other. Enough so that Master gave Carrie a new name, calling her simply girl. She has come a long way in the past few months, from a prudish housewife to a horny subservient slut ready to do almost anything to please her Master or fellow slaves. Unfortunately...

Workplace Fun by Karen Ch. 04

by Karenk63 on Aug 28, 2018
BDSM

After the end of October Halloween party I realised that it would not be long until my January birthday when I would receive a beating. As I had participated in thrashing others I could hardly avoid what was due to me on my reaching thirty. When after joining the company in May and realising what went on I had been filled with a mixture of fear and excitem...

Letter from Schenectady

by justincbenedict on Aug 7, 2019
BDSM

Dear Taryn, here is one for your "Interesting Tape Recordings" series from my wife's old college buddy, and my Dominant Mistress. Hope you enjoy! "So, Marseille--" "My parents were pretentious assholes. Just call me Mars." "Um, okay. I came here to see Georgene and Nivens, and I probably shouldn't have just dropped in, but this is weird. Who's the guy in...

Turning Tides

by Masterbation on Apr 15, 2020
BDSM

This story was created to entertain. All characters are 18+. I'm making my way into the community and would appreciate criticism, thoughts, and support. Thank you for your attention, we hope you enjoy your flight. This story was created in Co-Work with the volunteer editor Nouh_Bdee. Thank you so much. *** I enter my home after a hard day of work, too ti...

Sexy punishment for Bella Pt. 02

by Bella_Gigi on Mar 3, 2020
Group Sex

Part 2 Gigi surprises Bella with a threesome Read part 1 through my profile. *** After Bella got herself together, she believes it's unfair that both Anwar and Gigi still have so many clothes on. She decides to help them undress. Bella unhooks Gigi's bra and the girls together help Anwar out of his boxers. They climb on him and his just revealed huge hard...

Nurturing Cindy 06: Turning Point

by stoneartly on Oct 6, 2020
Novels and Novellas

Cindy told me that she had a surprise for me and I was to come to her house at two. I knocked on the door and heard her say, "It's open, come in." I opened the door and Cindy was slouched on the chair, legs extended out, wearing a short belted silk robe. She opened her legs, placed the heel of one foot on the cushion, and pulled her robe open. Her freshly...

A Sister's Revenge Ch. 01

by Johnboy9 on Sep 18, 2017
Transsexuals & Crossdressers

This is a revised version of the "Sister's Revenge" story. I am only doing this because in coming back to this site after so many years away, after having originally written the first series, I feel my story-telling has gotten much better, at least in my ability to write it down, and much less cruel, as the way I feel about my life has become more peaceful a...

Telepath King Ch. 15

by LustinTranslation on Sep 25, 2017
Novels and Novellas

Another for ya, enjoy! Chapter Fifteen - Punishment, Forgiveness, Betrayed Again Outside, we were greeted by Deanna with cigarettes and a bottle of fine Irish whiskey. I sat down at one of the patio tables, and watched as she poured my drink and lit my cigarette. Sophia sat next to me, scooting her chair close enough that I could touch her. This act showe...

A Demon...Or Two Just For Me Ch. 02

by Reddestiny921 on Sep 18, 2017
NonHuman

(O_O wow I was not expecting that type of feedback, thank you to everyone, this story will have multiple chapters but if by the end you still want a sequel just let me know. I love to know that it was enjoyed and that the length was acceptable. As you may have noticed I had a ton of fun writing the previous chapter, this chapter will probably have less sex b...

The Maestro Ch. 05

by barabajagal001 on Sep 19, 2017
BDSM

Hands. There were hands everywhere. Hands and tongues. Someone's hands on her breasts, and another pair of hands holding her legs open, where one tongue was licking her ardently. Her hands twined in golden curled hair and her tongue twisting with the man who owned it. Then he was gone, replaced my the man with the so-handsome face, capturing her mouth so tha...