Sissy Pimped Out Roleplay Stories

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House Rules

by GavinNuisance on Mar 16, 2020
Transgender & Crossdressers

Los Angeles, California. It's where we used to make movies. Through all the powdered glitz and pretentious glamour lies a smoldering relic of a bygone era. An era of entertainment, sun, palm trees, and success. It now is a shadow of its former self, overrun by high taxes, rampant homelessness, and drug problems from Downtown to Venice Beach. But in this sto...

Powerless

by siscuc on Sep 16, 2017
Transsexuals & Crossdressers

I was alone in the house, Tina was at work. It was 4 in the afternoon and i was looking over some pictures when the phone rang. It was Tina, "Hi Sweetheart" i said. The tone of her voice was harsh "Start getting ready, tonight you will be my sissy, you can choose to wear any of my clothes except the ones in the top drawer, I'll be wearing them." That was all...

Sissy's Decline into a Slut Pt. 04

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Six: Chantel's Decline is Achieved, Owned by a Black Master as his Sissy Maid and Slut. I cannot believe at what is happening to me here. Master named Gage is about to purchase me and place me into slavery as his sissy maid and sissy slut. I am near in panic, I want to run away, get into my car and drive for the safety of my home. But I know this wi...

House Rules Pt. 02

by GavinNuisance on Mar 16, 2020
Transgender & Crossdressers

Terry laid naked on Lana's couch, face down with his ass sticking up. Her cum had dried. Drowsy, and still a bit tired, Terry began to move, and stretched as he adjusted his eyes to light. He noticed the sun was setting and he was clearly there for at least a few hours. He rubbed his eyes, but noticed a peculiar feeling in his backside. "What the fuck?" He...

Sissy's Decline into a Slut Pt. 05

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Seven: I've been taken, Made into a Maid, Turned out as a Slut. Two days have passed by, it's Thursday morning. Today Master Gage and Master Martin are to arrive by 10:00am. I awake by 8:00am and my stomach is turning. I get up sit on the edge of my bed wearing my sleeping lingerie today it's a white satin full slip, white lace bra and satiny panty....

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...

Sleazy Times and Sluts

by DickThePimp on Dec 9, 2019
Celebrities & Fan Fiction

Ahhhhhhhh. Nothing like a mid day piss. Especially in the fancy ass lobby of your office/apartment building. Right there in my favorite chair. Piss flying on the fucking floor. I own the building, so no pain in the ass bitching about it. I love pissing in front of people. All over people too. I get off on it. They do too. Most of em do. The others... fuck em...

Mistress Red Fox Becoming a Devotee

by His_fag_wife on Sep 24, 2019
BDSM

A story of what might have been a dream. Names have been changed. *** One evening I was looking through profiles on a BDSM website and came across one for a local Mistress, she was developing a new dungeon and she was asking for suitable subs for her to try it out on. Someone to test the new equipment and layout on. I read the ad over and over again, this...

Few of My Ultra-Perverted Fantasies

by whiteboibbclicker on Sep 16, 2017
Transsexuals & Crossdressers

Hello, I am a white boi who's addicted to sissy porn and have a lot of wicked and perverted fantasies. In this list, I will enumerate some of them. I would ask the readers to name the one that they like the most in the comments section so I can write a story about it. Authors are more than welcome if they want to write about any of the themes mentioned here...

White Gurl Pimped in the Hood

by Stephisissycd on Sep 11, 2017
Group Sex

After Black Mike made me his bitch, showing up at motels all over town dressed like a street hooker, he sent me a text one day. "Hey bitch. I need you to dress really slutty, get smooth and totally clean, and meet me at the motel at 6th and Los Angeles st." I knew where that was, right by skid row. My pussy started to throb thinking about what black mike h...