Pimped Out Sissy Stories

353,644 results
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Beating a Ticket

by jjgarces on Sep 12, 2017
Celebrities & Fan Fiction

It was just another night of patrolling for me on the little stretch of lonely country road that I patrol as part of my job as a cop, and up until that point, nothing exciting had ever happened. Being that it was just outside of Hollywood, I had always secretly hoped that I would have a run-in with a celebrity, but so far, that had yet to happen. But when...

Workout Session

by JesseEvans on Sep 19, 2017
Group Sex

My best buddy, Will, came over today for a workout in my backyard. Will and I have been friends for years now, all the way from kindergarten through college. We try to work out as often as we can, and have set up our own kind of gym in the backyard. Once he comes over, we stretch out, and begin bench pressing. We usually shoot the shit for a while when we...

Driving Ms. Gifford

by DickThePimp on Sep 4, 2018
Celebrities & Fan Fiction

This is a pussy pounding parody... But, it ain't real... Unfortunately. I was starting my first day on my new job, driving Kathie Lee Gifford. I was at her home in Greenwich waiting to drive her to NYC. It was veryyyyyyy early. It was the only bad part of my job. I have a massive crush on Kathie Lee and she was very nice when she interviewed me for the job....

Blackmailed into Submission Ch. 02

by tzleaze123 on Mar 26, 2019
Transgender & Crossdressers

How in the Hell did this happen? I am not about to let this little girl blackmail me. She is only 20 and cannot possibly know how to pull something like that off. She has already had me sucking cock (first time) in front of a guys girlfriend. I have no idea who it was because I was blindfolded. Sure she said his name was Jack and his girlfriend Kim and true...

K's Candy Ch. 006

by candy_slut on Sep 14, 2017
BDSM

Part 6: Busy Day I was cleaning up after breakfast when Katherine called to me. "Here's everything you need." I peeked around the corner at her. She smiled. "Oh, and I realized I might not have been clear about something. When I said 'wash the cars' I meant you wash the cars, not take them to a car wash." She turned and started to walk away. "OK, time for...

Earning Their Record Deal

by jjgarces on Sep 15, 2017
Celebrities & Fan Fiction

I hadn't been working at my job as a record executive in Nashville for too long when I heard the rumors that the "next big thing" was about to hit Nashville, in the form of a couple of hot blonde 19-year-olds named Maddie Marlow and Taylor Dye, who are now professionally known as Maddie & Tae. Recent trends, though, suggested that female country artists wer...

Enjoying the Strawberries

by kris_with_a_k on Sep 13, 2017
Erotic Couplings

It's a cheerful Saturday mid-afternoon and you and I are out picking up some food at a grocery store. Walking down the produce aisle, we pass a bin full of those little green baskets of strawberries. I get a big grin on my face and reach out to pick up a basket to put in our cart. You're watching me, trying to figure out what I have in mind, but I'm not givi...

Lindsey and the Crew

by sportsfreak9182 on Sep 1, 2017
Group Sex

Scott and Lindsey walk into Starbucks, get their drinks and find a table secluded near the back. Scott's phone starts buzzing, as he gets a text from Alonso saying he is here. As he looks up, Alonso is entering the building. He walks over to their table as they stand up to greet him. Scott and Alonso shake hands, while Lindsey and Alonso hug his hands moment...

Elaina and Kayla Pt. 01

by katiegray on Sep 12, 2017
Toys & Masturbation

After the four-hour drive to Washington, DC, Elaina slid gratefully out of the car. Traffic on Interstate 95 was always terrible; she didn't know how she had been so lucky today. Before reaching into the back seat of the car to pick up her bag, she stopped for a moment to look at the house where she would be staying this weekend. It was a simple row house, r...

Nailing the Interviewer Pt. 03

by jjgarces on Sep 13, 2017
Celebrities & Fan Fiction

"John, are you crazy? I don't mind interviewing almost anyone you ask me to, but you know I hate that bitch!" Katie complained to me one day after work in the house we now lived in together, having just fucked when the subject of her interviewing Taylor Swift for the show came up. "Katie, how can you hate her when you haven't even met her?" I asked her, try...