Boipussy Stories

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Husband Turned Fuck Hole

by Sjen451 on May 2, 2018
Transsexuals & Crossdressers

I'll share a sexual story with you. I'm in my early 30s now and have spent years exploring myself, especially my boipussy. Now it's even more exciting and pleasurable for me to fuck my ass than it is to masturbate with my cock. But that's not really something you can tell anyone, so I'd buy sex toys when I went out of town for work, had wonderful fun in...

How I Got My Sissy Name

by allourdesires on Jun 5, 2019
Transgender & Crossdressers

The thing was that He had presented me with the earrings, on my birthday, in front of my wife and innocently enough I had accepted them with embarrassingly gushing sissy enthusiasm, being my first pair that weren't clip-on. The very next day she dragged me along to the local mall, where all of my friends and neighbours shopped, to get my ears pierced at a ce...

Yesterday Afternoon

by allourdesires on Jun 10, 2019
Transgender & Crossdressers

A lunchtime call; I was to leave work immediately. Once home I would find everything laid out on the bed: nightie, bralette, cotton panties, hold-ups, lipstick, silver choker and...a blindfold? When I was ready I rang her as ordered, covered my eyes and began to toy with my nipples in anticipation of what was to come. My little clitty jumped inside my panti...

Mrs. Henderson Emasculates An Ex

by skriblur on Sep 16, 2017
Transsexuals & Crossdressers

The elevator doors slide shut and Sissy Kimmi taps the special access code into the keypad. Then she presses the "PH" button. In few seconds, she'll be at Mrs. Henderson's place on the top floor. Mrs. Henderson is not the type of woman who sends invitations to sissies. She's the type who tells 'guests' where to be and when to be there. Her handwritten summo...

Special Delivery

by edm_amanda1 on Sep 14, 2017
Transsexuals & Crossdressers

Another story that actually happened to me. It's a bit long but I think it's worth it, enjoy. I was 22 and had just moved into my first place by myself a few months before. It was so liberating having my own space to be my true self without distractions or interruptions. Every day I came home I immediately transformed into Amanda and loved the freedom she g...

Just This Once Ch. 03

by SecretRaptor on May 20, 2019
Transgender & Crossdressers

Click. The clock on Max's wall continued around its cycle. "3 pm" I say out loud to myself. Two and a half hours before my lover comes home from work. Not soon enough to begin cooking dinner. Click. I shift in my seat. My limp, shaven clit pushes uncomfortably on the tiny pink chastity cage. I am in desperate need for release, as Max and I didn't have...

The School Tramp

by tawnysuede on Sep 19, 2017
Transsexuals & Crossdressers

(From "Boy" to " Boy oh Boy!!") Chapter 1 - The School Tramp I was a virgin. I did not want to be a virgin. I asked my sister for help, and that was a mistake. Well, at the time I thought it was a mistake, but it turned out to be the best mistake that I ever made. I was nineteen years old at the time and entering my junior year of high school. Yes, my ju...

Strapon Dream Cum True

by AfroerotiK on Sep 13, 2017
Fetish

Edward sat at his computer screen, staring at his monitor until his eyes started to close from exhaustion. Every once in a while, he would get so horny, so desperate to experience his fantasy he would stay up all night just stroking himself and looking at porn, desperate to feel . . . it. He had pretty much resigned himself to the fact that he was never goi...

Dena Goes for the Stars Ch. 02

by daisyboi_sissy on Sep 16, 2017
Transsexuals & Crossdressers

This is a work of fiction and everyone included would be over 18 years old and responsible for their own actions. * When I opened my email, there were a few messages from Mr. Lane with links to various websites. One was rather interesting in that it was dedicated to the idea of very androgynous young people and their work as models in advertising. I was in...

White Boy Swagg

by puzziboi on Mar 23, 2020
Transgender & Crossdressers

"Y'all tell Gigi and Big Dad bye," instructed the thirty-one year old father of two. "Bye, bye," said the older one - a girl of four. The younger kid, a boy aged two, began to pout. "Come on now, Maverick. Stop actin'. You know you're goin' to a birthday party,' ' Josh Myers reminded his son. "It's okay, Mav! Gigi will come see you later," Lori Myers att...