Boypussy Stories

107 results
Orientation
Length
Source
Infinite Scroll

The Alex Experiment

by Certeis on Aug 21, 2019
Transgender & Crossdressers

Alexa timidly set foot in the bar, and was immediately assailed with a sense that she didn't belong there, but she fought back against it. She really wanted to go out and have some fun, to have a nice night without some creepy guys hitting on her or groping her. Last week she'd even caught some weirdo trying to put something in her drink, and she was thoroug...

Am I Who I Think I Am? Ch. 02

by Clintdear on Sep 26, 2017
Transsexuals & Crossdressers

Well,I can't lay here all day and dream! I feel so good, so loved, so ravished. My smile is touching the pillow on both sides! I'm laying here daydreaming about my deflowering this morning. Inside me lives my lover's DNA, looking for a life to create. (Nice try little spermies, but you won't find it there!) I can still feel the gentle purring of my boy pussy...

John Meets Amy, Finally Pt. 02

by amygurl on Sep 15, 2017
Transsexuals & Crossdressers

After college, I moved to where I live now and got a job. After a short break of not going out, I resumed my casual lifestyle. Which brings us to the present. I had arranged to go to my brothers for the weekend to visit, we usually tried to visit at least every 3 months or so. During the first night, he was complaining about his girlfriend, they were fightin...

Transsexual Sex Slaves

by Otaku_Apologist on Jul 15, 2020
Transgender & Crossdressers

With a blank expression, she wept. The cock had a pulse. That pulse echoed from the hips to the shaft to the mushroom head and into her ass. She was a newborn dick girl, and she felt the soft, hard skin of her partner's cock dig into her cum-moist boypussy. Her tunnel was fully lubricated by sweat and foreign jizz. The erect arousal probing her stomach reach...

The Journey Pt. 03

by MissYellowPanties on Sep 14, 2017
Transsexuals & Crossdressers

Training It was an unusual feeling walking down the corridor, my sissyclit was hard with excitement and I had not yet adjusted to the feeling of the butt plug placed firmly in my boypussy. I still tried to move in a ladylike fashion, but the strange sensation was overwhelming and I stumbled suddenly out of time with Mistress Anna's gait. Mistress Anna...

Secrets of The New World Order Ch. 05

by bjmichaels on Sep 16, 2017
Sci-Fi & Fantasy

I was beginning to feel somewhat lightheaded. I wasn't sure if the second-hand smoke from the marijuana inside The Coral Reefer was affecting me, or whether my nerves were reacting to the fact I was about to meet a powerful man, perhaps someone I knew, who'd made an interesting bid on my virginity. There was a slight commotion at the podium. I looked and s...

Growing up Feminine

by Clintdear on Sep 26, 2017
Transsexuals & Crossdressers

Chapter One By the time I graduated, I was really beginning to appreciate the fact that I was attracting men now. I was interested in them too, but wary since not all of them were interested in me. Since I was only 5'4" and 110 lbs., they were much bigger than me, and there was always some odd urgency about them that warned me to be careful around them if t...

Mistress Jaz's Sissy Slut

by barbiboi on Aug 30, 2017
Fetish

Mistress Jaz had invited me over to give her a pedicure and provide sissy maid service. What I got was a mind blowing day of servitude I will never forget! I arrived in the morning and was greeted by a vision of beauty. I had seen pictured of Mistress Jaz before, but they paled in comparison to meeting this incredible Goddess in the flesh. Tall, curvy, wit...

Greta Fights Mommy Adriana

by Gretatv on Sep 16, 2017
Transsexuals & Crossdressers

Dear Readers, this is the second part of the Mommy Adriana series. I hope you enjoy the ride, there is more to come. * * * * * Mommy Adriana continued her assault on my boycunt with her 10 inch strap-on dildo stretching me to the hilt. Meanwhile Andrea, my wife, had gotten up from my face, leaving me drenched in her juices. She sat exhausted on the couch...

Being Jenny's Summer Boyfriend Ch. 03

by Lucas96 on Jan 21, 2020
Fetish

Disclaimer: this story involves cuckolding, humiliation, cross-dressing, and gay incest. *** I have to admit, it was difficult to contain my excitement as Jenny invited my dad and brother over to show them what a little sissy slut I'd become. To prepare, Jenny let me try on the outfit she'd had on when we'd come over to Andrew's house: a pink, tight-fitt...