Plug Punishment Stories

45,846 results
Orientation
Length
Source
Infinite Scroll

Kitten, Humiliated

by Jinx1621 on Sep 24, 2019
BDSM

I love my job. I'm a secretary for the CEO of a large financial institution. It doesn't sound like much, but the perks are fantastic. Every day, at the end of shift, Mr. S, my boss, becomes Mr. S, my master. As soon as my day ends I'm expected to be promptly in his office, stripped down to matching bra and panties ready to give myself to him in anyway he dee...

Skyrim: Punished by Astrid

by kajiragames on Dec 31, 2019
Celebrities & Fan Fiction

Based on the Skyrim RPG game, Assassins Guild characters. by KajiraGames - F/F caning & groping "You've paid your debt, but you still need to be punished!" Dovahkiin looked wide-eyed at Astrid. She was in awe of her Dark Brotherhood leader. Ever since she had first seen this cool sexy woman sitting on a shelf up in the corner of the old cabin, she had fel...

Captive Hacker Ch. 02

by CaptiveHacker on Sep 17, 2017
BDSM

If you enjoyed this story and would like to comment then please write to the link below. ----------------------------------------------- I can now confidently say that my lower body is as hairless as Mistress Green wants it. An afternoons waxing with Mistress Benny made that a certainty. I endured the pain as best as I could, indeed any begging and pleadin...

Side Bet Bluff Ch. 07

by statsultan on Sep 14, 2017
BDSM

Part 7 – Tuesday (Jan. 20) "Sure, Will, I can find some work I can throw your way once you land somewhere, but you have to know that all of the origination work has just vanished completely." "Yeah, I know, Dan," I said into my phone to the sixth potential client I'd gotten a hold of this morning. "But there's going to be some statutorily mandated loan mod...

A judicial punishment

by Studio2 on Oct 21, 2017
BDSM

In the near future, the justice system has reintroduced the use of corporal punishment for minor offences, or when the person in question would be unfairly affected by a prison sentence. The punishments are designed to be both painful and sexually humiliating for the offender. Both men and women over the age of 18 are punished in this way...What's next? Mal...

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Coach Daddy Ch. 03

by whatcouldofbeen on Sep 18, 2017
Transsexuals & Crossdressers

A short time later, Beth and I arrive at my apartment. Giggling we unload the car and carry my knew wardrobe in. We drop all the bags on the floor and I flop down onto my couch exhausted from my day. "First of all young lady you are still acting like a boy. Ladies do not just flop down with our legs spread wide. You are showing the whole world the goods."...

Allison's New Life

by Goldeniangel on Sep 12, 2017
Novels and Novellas

author's note: If you want to read more about Allison's previous adventures (although I do explain it some during this first story) check out the series "Poker Loser" in my bio, it's kind of a prologue to this novel/novella. ********************************************** Allison sat looking in her mirror, waiting for Roger to pick her up. He would be her f...

Happy Anniversary

by Cheekyoz on Sep 11, 2017
Loving Wives

Happy Anniversary For our 8th wedding anniversary I had taken my wife out for dinner. We enjoyed our time away from the kids, and my wife had clearly enjoyed her glasses of wine. Whenever she has had too much wine, my wife would become extremely horny, my mind started thinking about the fun we would have when we got home. On our way home, I felt my wife's h...

Allison's New Life Ch. 08

by Goldeniangel on Sep 16, 2017
Novels and Novellas

Being with Todd for one incredible night and having him leave again had left Allison more despondent than she would have thought possible. She moped and sulked for a few days, never leaving the house as Diana and Chad tried valiantly to cheer her up. After the second day she started accepting calls from Roger again, although she kept making up excuses as to...

Sissy Son Taken to Costume Party

by JD2100 on Sep 26, 2017
Transsexuals & Crossdressers

I was making my way to my moms and dads house to house sit for them as they were going to a party that night and I had agreed to be there to watch the house and hand out candy. I was going to be alone in the house. I loved being all alone as it gave me a chance to partake in my fetish of dressing up in girls clothes. My sister still lived there and she had s...