Sissy Bookstore Sex Stories

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Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...

The Booth in the Back

by mona215 on Sep 16, 2017
Transsexuals & Crossdressers

On my knees on the vinyl floor, the metal choke chain around my neck, one end of the chain under the pointed toe of her fuck-me heels, keeping me bent over so that my pantied ass is sticking up into the air. The sound of her crop slapping against my silky undies punctuating the mean things she says to me in a bored voice. "Real men don't wear girly panties...

Satan's Sissy

by nancyvasquez on Oct 15, 2017
Transsexuals & Crossdressers

Oh you stupid little faggot! You just had to go and get married to a woman! Why?? Why fuck up some poor girl's life like that? Was it because you crave humiliation, and subconsciously you knew it would be just a matter of time before you got caught, and you would be outed publicly? Outed as a pole smoking homosexual who was more at home in frilly skirts and...

Sissy for Satan!

by nancyvasquez on Jan 14, 2018
Transsexuals & Crossdressers

Oh you stupid little faggot! You just had to go and get married to a woman! Why?? Why fuck up some poor girl's life like that? Was it because you crave humiliation, and subconsciously you knew it would be just a matter of time before you got caught - and you would be outed publicly? Outed as a pole smoking homosexual who was more at home in frilly skirts and...

Straight Guy Gets Some "Strange"

by nancyvasquez on Oct 15, 2017
Interracial Love

The Negro saw the bright lights across the street advertising the adult bookstore. He felt a stirring in his groin and he pushed down on his cock. He could use a jerk off session, he hadn't cum in a few days. It was a very warm night, and the rain had stopped, leaving the smell of wet asphalt in the air He went to the counter. "How much to go in the back?"...

My Visit to the Adult Bookstore

by Sissy_Kimmie on Oct 3, 2018
Transsexuals & Crossdressers

My dom instructed me to write and post this true story. Since I had a Dr. appt at the end of the day, I knew it would be a good time to visit the bookstore. It's been several weeks since I've sucked a cock, so my Dom felt I needed to be fed today. We texted throughout the day, but he wouldn't be able to meet me. I also had been chatting with another local D...

Down The Path Ch. 03

by gbr2004 on Sep 14, 2017
Fetish

This story involves gay sex and forced fem, not your thing, move to another story. * I haven't been able to concentrate all day, didn't get anything done. All I can think about is having to go back to the bookstore tonight. I don't know if I can do it but if I don't I'm not sure what he might do. Maybe he just won't contact me anymore and I really don't w...

First Time Sissy at the Gloryhole

by Stephen_Heathcote on Sep 16, 2017
Transsexuals & Crossdressers

Once I realized that I liked to wear panties, I wanted to be seen in them. But I didn't want to be seen by anyone that I knew. That would be too embarrassing. I drove to the next city over and walked around with the satiny fabric caressing my cock beneath my clothes. I had dinner. I shopped. It was fun having a secret, but the excitement wore off quickly. I...

Sissy Keven Jeanne Bardot

by nancyvasquez on Sep 14, 2017
Erotic Couplings

After Jinky and I had been married about a year, she began to make gay references about me being gay. When I'd get mad, she'd laugh and say, "I'm only joking!" I remember she always used to squeeze my breasts, which were quite prominent, and say, "Wow, sweetie, nice development!" And then she'd laugh. My feminine breasts had been a source of embarrassment f...

Transition from Man to Lady

by nancyvasquez on Oct 10, 2017
Erotic Couplings

I was born male, but both physically and emotionally I was more female. I went out of my way to - just barely - avoid being regarded as a sissy by my peers growing up. But after I hit puberty I never really developed the physical characteristics associated with manliness. By age 18 I had reached my full height of 5',6", and was small boned and delicately bui...