Self Degrading Sissy Fuckboy 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...

BitchBoy

by GothVix on Sep 15, 2017
Interracial Love

I sit at my local spot at the café; sipping my mocha and watching the time pass me by in colors. It won't be long before the closing time hits and I'll be forced to leave my chair and find another spot to brood and grumble. I haven't received the financial aid that was promised me in weeks. I can honestly say, as a black woman of pride, I need that money....

Self Sucking College Boy

by cockwhores on Sep 25, 2017
Fetish

When our new next door neighbors said their nephew was going to stay with them this summer, I didn't realize it was May and that he was in graduate school. I also didn't realize they were going to be out of town most of the summer and that Drew was such a stallion stud. I saw him the day he moved in. He had a great, tight toned body, long dark hair and a gor...

Absurdly Slutty Hand Job

by cc_cummings on Jul 9, 2019
Exhibitionist & Voyeur

I am not a particularly nihilistic slut. By this I mean the stupid whorish things I do tend to be meaningful to the dumb hot people I impose upon. Consider yesterday: In the call it early afternoon, this cis gentleman who I coerced with pizza into bringing me home the evening prior woke up from a nap to hear his roommate and her mom arriving home. I had be...

The Descent

by pantywriter on Sep 28, 2020
Transgender & Crossdressers

It had to be too good to be true, I thought. No woman had ever come on to me like that before. She was pushy and for all intents and purposes, demanded that I escort her to this dinner date in the city. Sure, it was Valentine's Day, and she did admit earlier in the night that being mid-50s and single on this day agitated her; hence, she demanded my presence....

An Orc's Slave Ch. 11

by simmaster on Sep 14, 2017
Sci-Fi & Fantasy

This is the first time I try my hand at switching perspectives. I prefer not to do that, but for this chapter it felt inevitable. ***** As I put another bag of silver on the carriage, it was finally full. Ebba and I had been going back and forth several times to get as much silver as my poor horse Maggie could drag. Now there was finally no room for more....

Jock Princess Ch. 02

by Sissyhalo on Sep 15, 2017
Transsexuals & Crossdressers

My brain trembled with my body. I could feel it, my insides all those nooks, crannies, all those muscles inside me trembling inside from being fucked so hard and so deep. All mirroring my brain and the shock of getting fucked too and how much I loved it. And I did love it, more than I should, more than any jock guy ever should. If there was a part of me t...

Husband Is a Fuckboy

by cockwhores on Sep 12, 2017
Fetish

I told you how my husband worships my bald pussy and loves to suck and lick my asshole. And how, when we got our sex toys, it turned us both into cockwhores. After that great fuckfest and me coming 5 times with my husband, we had another hot sex fest. The next day was Saturday so we had the whole weekend to play. In the morning we took a shower together. I...

Cockwhores Sexfest

by cockwhores on Sep 16, 2017
Loving Wives

I love turning my husband into a fuckboy. He's always been a great fuck with a thick, 9 inch cock. But he's turned into a great ass and pussy worshipper and also a wonderful cockwhore. He worships my bald pussy and loves to suck and lick my asshole. We love sex. He also loves cock. It started with dildos and strap-ons and cum squirting rubber cocks. Now he...

Sissy's Decline into a Slut Pt. 03

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Five: Oh, Oh, Things Look to Begin to Radically Change for Chantel. Well another week has passed by, it's Friday evening and tonight I have to go back to the rest area to hook up with Barry and Ralph as they instructed from last Friday after having me suck their cocks. They promised me that they will fuck me tonight and share me with even more men....