Boi Pussy Stories

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Orientation
Length
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Infinite Scroll

A Virgin released from Chastity

by ronron1818 on Nov 16, 2020
Fetish

It was time to move on... I will be graduating today, 4 years after moving in with Ruth, and tomorrow, I will be moving out to start my life as a grown up. I already found a job in my home town, and rented a small apartment near the new office place. Ruth came with me and my parents to the graduation event. My parents liked her a lot. For them, it was lik...

Truth Or Dare Clusterfuck Ch. 02

by SEVERUSMAX on Jul 2, 2019
Interracial Love

"Oh, fuck ... yes ... fuck me now, Frank!" Emily screamed my name loud enough that the others could hear it over their own moans and groans. This was our second wind, as it were, some forty-five to fifty minutes after we finished up the last bit of fun. The sexy Southern beauty certainly had my number, taking me deeper and harder for every stroke as I pound...

Dear Matt

by cdtiffanymd on Oct 19, 2020
Transgender & Crossdressers

Dear Matt, I'm so sorry that I took so long to get back to you. Every time I tried to write to you these last few days my wife walked in to the room so I had to stop and hide what I was doing. But the other day I got her. We were in the car and she was driving so I started to daydream about us, We were driving around in your car together one night. Your ri...

Shattered

by kayla_femboi on Sep 16, 2017
Transsexuals & Crossdressers

The following story is mostly true. I changed the names for the sake of privacy and maybe spiced up the details a bit. A little background about me: my name is Brian, although when dressed i feminize me name to Brianna. I was a closet crossdressing sissy. I had always been effeminate growing up and a bit confused sexually. I never really dated girls. Inst...

House Rules Ch. 09

by EROTICbearscribe on Jan 22, 2020
Transgender & Crossdressers

AUTHOR'S NOTE: This story contains characters and references to events in two previous stories I have written: Just Across The Hall and PIXIE: Sissy Stripper. It is not necessary to have read these two story chains. This chapter of House Rules could stand on its own for entertainment purposes. If, however you want context, please read the other two stories f...

Gemini Triad: Prologue

by JordonLynn on Sep 13, 2017
Transsexuals & Crossdressers

Author’s acknowledgement and a short note… a plea, actually: First and foremost, I want to thank the Lit members who cast their votes and made Chapter 2 of Bigger Bites of Taboo Apples the Interracial Story of the Year. This is an honor I never expected to come my way when I first began posting my humble offerings. Even more, I want to personally thank al...

How To Be A Boi Bitch Lesson 06

by gothicboibitch on Sep 13, 2017
Fetish

You haven't been thinking about me all that much, have you? Since you and me fucked your wife, your girlfriend together. And in the beautiful glow of you two, lying together in your bed, you felt such peace. Maybe this was all you needed. To get the bitch out of your system. To get me out of your mind. Did you beg god for it? In that one moment? When I slid...

The Ventriloquist

by justincbenedict on Sep 16, 2017
Humor & Satire

THE VENTRILOQUIST (Or, "Which one's the Dummy?") Okay, like, I don't know why it happened, but it was fuckin' weird, man. I was sitting in the lounge of Texas Tommy's Boi-Toi Ranch, when they got an outcall for a "Big strong, hustler". As Mickie at the desk said, they wanted the biggest boy there, ALL OVER. Next to "Detroit Half-Smoke" Willard, who's...

A Natural Sissy Ch. 02

by harv069 on Sep 15, 2017
Transsexuals & Crossdressers

Author's note: This is a story about a woman who turns an older man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. You will need to read the previous chapter to see how we got where we are in this one. More will be added if comments...

Slave Ch. 11

by slaveheathen on Sep 25, 2017
Fetish

SLAVE Note: I have no idea if a resort like the one in this chapter actually exists, but damn I'd love to go if it did! If you haven't read the previous chapters, I'd suggest you do, as it would help to understand the characters better. This story is about a bisexual man who has completely submitted to his Mistress. It contains scenes where he has sex with...