Story Of A Sissy Prostitute Stories

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Cheap Sissy Whore To Call Girl Ch. 02

by HardSoft on Sep 15, 2017
Transsexuals & Crossdressers

The day I woke up after being knocked out was a strange one. I didn't know how long I had been missing but I felt my body had been completely transformed. My skin felt softer, I had breasts, my lips were filled with collagen. I remember waking up in a what seemed like a hospital room and walking up to a mirror and looking at a gorgeous bald woman with a peni...

Sissy_World 03

by JDBones on Sep 16, 2017
Transsexuals & Crossdressers

Billy rode in the front seat of the car, staring out the window, and watching the world go by. His mind swam and his body already hurt, but he knew better than to protest his pain to his Husband. If he did, he would be punished with a Bare ASS Spanking and he didn't want that. He stood at 5'6 and weighed maybe one hundred pounds soaking wet, but he doubted...

Interracial Sissy

by nancyvasquez on Sep 16, 2017
Interracial Love

Remember how I told you the story my ex wife told me - of how that white prostitute at the strip club came out of the booth after having been in there with a black guy, and how she was flushed and proud and was telling all of the other hos about how proud she was to have been with that handsome black man? Well it happened to me tonight! I almost can't believ...

Afro Stress Relief Ch. 07

by llts1970 on Sep 23, 2019
Transgender & Crossdressers

Author's Note: - there was a character in the previous chapter called Jane who was working in Tina's company, I realized this was too confusing because of the main character Dr Jane and so I've changed the name from Jane to Monica. I apologize for the delay in getting this chapter out and hope to have more chapters completed sooner. ***** Staci rang and sa...

Humiliated Sissy Slut

by Allice on Sep 16, 2017
Transsexuals & Crossdressers

I have been dressing as a woman at home in private for many years. No one has ever seen me dressed as a sissy slut before but I do it to feel sexy. I know I would never pass as a woman for I am 6 feet tall, 170 lbs and at the age of 45 not a real trim body. My girlfriend Rachel who lives with me is must younger at the age of 35 with a young trim body that h...

Julie is a Whore Ch. 06

by Pretty_Sissy_Julie on Jul 14, 2020
Fetish

Ch 6 Hello, my name is julie and I am a sissy CD. I am very passable and by the time of the events in this story took place and I had a nice bra size of 34B. This is a difficult story for me to write because I am going to write it in 3 parts. The first 2 parts will seem to be unrelated, but hopefully the third part will tie it all together. Just as a warnin...

Afro Stress Relief Ch. 05

by llts1970 on Aug 1, 2018
Transsexuals & Crossdressers

My alarm went off the next day, my mouth and asshole ached, it was going to be a long day I thought. I had put plenty of grease up my asshole just to ease the soreness but it still felt pretty stretched. I started to remember last night, I couldn't believe I'd taken Baba G's fat black penis in my mouth, or that I'd spoken to the police officer like that! I w...

Julie is a Whore Ch. 02

by Pretty_Sissy_Julie on Jun 2, 2020
Transgender & Crossdressers

I would suggest you read the first chapter of this series, but for now; I am a very submissive sissy that has just agreed to become the property of Madame. I did so in front of a demanding and demeaning woman I have lived with for a week. During that time she brutally beat me and I loved it. She even had me licking her filthy arse after she shit, and again,...

Afro Stress Relief Ch. 06

by llts1970 on Dec 12, 2018
Transgender & Crossdressers

I was running a bit late after I'd overslept my alarm clock, my shift at Missy Bee's and the hard riding I got from Leroy must have tired me out more than I thought. I managed to get into work just on time, once there I rang Sarah. "Oh hi Johnny, sorry I mean Tina, wow it's early," Sarah lazily answered. "Hi Sarah, is Marci OK? I can pick her up this eveni...

Ian's New Job Ch. 02

by SatinSlip on Dec 10, 2018
Fetish

Authors note- this story includes non-consensual, rough, and coerced sex. As well as straight and bi-sexual sex, crossdressing, and humiliation. ********** Wendy wore the shortest skirt she owned. A blue, pleated thing that stopped a few inches short of her knees. Underneath she wore red lace panties Ian had bought her for valentines a couple years ago, an...