Boipussy Stories

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PIXIE Sissy Stripper Ch. 04

by EROTICbearscribe on Jan 20, 2020
Transgender & Crossdressers

Author's Note: There is a category switch in this chapter. The beginning chapters can be found in GAY MALE. Seeing as what happens in this chapter, the new category is TRANSGENDER & CROSSDRESSERS. ***** THE PINK BOY was located in the warehouse district across town in an eclectic area known for its nightclubs and specialty bars. Within a six block radi...

Rosie Finally Meets Jessica

by DoesAnyNameWorkOnHere on Aug 6, 2019
Transgender & Crossdressers

It was cold. Bitter cold. January always brought negative temperatures and more snow than I care to see. It's the kind of cold that gets into your bones and you can feel it for hours after being in a warm place. Not even a hot shower can soothe the chill you have inside. Short days and long nights made the month long and depressing. My only respite from the...

The Succubus 'n The Yogi Ch. 01

by Ashesh9 on Sep 2, 2017
Erotic Horror

I was attacked last night as I sat in the Padmasana pose meditating on my Squeezed Lingam's Svadisthana chakra! My attacker was a female Creature from Hell: a succubus I believe the Western civilization's Legends call It!?! But she, of course didn't know I was an accomplished Vedantist & when immersed in Adaivtya Vedanta/ Absolute Reality am beyond the gra...

Sissy Cristal Used by Mistress

by mistressandpussyboy on Jan 8, 2019
Transgender & Crossdressers

This is a real life story, another day in my life with my Mistress. We were ready to go out to run some errands, when Mistress addressed me. "Plans are canceled. I want to bang a hooker: get dressed for me." No sooner said than done, I was getting naked, opening my sissy suitcase. I put on a pretty panty, black stockings, a miniskirt and my high heels. M...

My Master

by SissyKaty on Mar 26, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** I pulled into the driveway to my house and I was disappointed to see my future mother-in-law's car in the driveway. "Oh great" I think sarcastically. I'm not looking forward to interacting with her so soon after getting off work. I had just come from a long day working in IT for...

A Sissy's New Daddy

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

Walking in the door the Friday after my eighteenth birthday, everything seemed great. My parents had gone out of town for the weekend and I was for the first time a truly free man. My older brother had decided not to come home for Labor Day holiday which I was kind of bummed about, we didn't get alone all that well but I still looked up to him. He was one of...

Daddy at the Truckstop Pt. 01

by StaceyDeprave on Sep 15, 2017
Transsexuals & Crossdressers

This was an encounter that almost happened with a Daddy a while back. We talked about doing this for a first meet to make up for other times that didn't work out, and while talking about it with him was undeniably hot, it ended up not happening for a few reasons, chief among them safety. I think about how hot it would have been to smash a lot of my boundarie...

That's What Friends Are For Ch. 02

by TurningintoCD on Sep 13, 2017
Transsexuals & Crossdressers

I woke up in the morning both loving and hating what had taken place the previous night when my best friend David made me dress up in panties and a bra for him and promise that I will dress up as a girl for him on Halloween. All I wanted to do was please him. He wanted to see nail polish on my toes, so that's what I was going to have to do. I happened to ha...

Caged!

by yvetteinpanties on Jun 19, 2018
Transsexuals & Crossdressers

I was a late blooming sissy. Like most sissies-to-be, I had early incidents of trying on my sisters clothes and enjoying the way they felt, but I always viewed myself as a heterosexual who just liked to imagine stroking a nubile female underneath the lingerie I was wearing. It was much later in life that I took the serious turn from being a heterosexual cros...

Her First Time

by edm_amanda1 on Sep 16, 2017
Transsexuals & Crossdressers

Here is my very true story of the first time he came inside of me and marked me forever as his. Will and I had been seeing each other for several years. He had always accepted me for my inner woman and treated me like a goddess but I felt distant from him. I had always dreamed about having him cum inside of me but it was never the right time and I wanted it...