Sissy Prostate Stories

15,115 results
Orientation
Length
Source
Infinite Scroll

The Crimson King Ch. 10

by velvetpie on Sep 16, 2017
Romance

"Are you sure this is where she is?" The private detective Chambliss had hired shook his head as they sat in the limousine, staring at the huge mansion with its imposing dark windows. "My source says that the cameraman, Leon Antonidas, bought some maternity clothes and had them delivered here." "That doesn't necessarily mean that she's here." The detectiv...

Field Work Ch. 03

by kleve on Sep 25, 2017
NonHuman

Thanks to popular demand, the story of the trees continues: I had thought that my last bulletin on the subject of the trees would be the final word on the subject. But since then, there have been dramatic and disturbing developments, and we feel that the public needs to be informed. Gail and I had been continuing our research into the mysterious trees, exa...

My Father-In-Law's New Bride Ch. 03

by regina_allen55 on Sep 25, 2017
Transsexuals & Crossdressers

It had been almost two weeks since Tom had caught me wearing Donna's wedding dress and in that time I was well into my training as his new play thing. He had done everything to make me feel like the woman or the whore he wanted me to be from servicing both him and other men in the picture theatre, to where would take me out late at night to some clubs he kne...

Life Imitates Art

by Dual_Triode on Sep 15, 2017
Exhibitionist & Voyeur

A True Story. I doubt that Oscar Wilde had erotic literature in mind when he penned his famous aphorism. On the other hand, his self-described Socratic sexual identity certainly placed him at the fringe of Victorian morality. It is not so difficult to imagine carnal desires fueling his biting wit. This is not a story about Victorian era sexuality. This is...

Derek & Amy: Boys Night in

by Kalira on Sep 16, 2017
Transsexuals & Crossdressers

Tonight is the night Matt learns how to be a true lover. Before, he had his wife Amy to hold his hand when they played with Mistress Derek but tonight, he's all on his own. Before Mistress Derek arrives, Amy prepares Matt using the instructions she received from him. Matt is to be dressed in a sheer, pink babydoll top with fluffy breasts and matching panties...

The Sexy Domme Next Door Ch. 05

by rickiee_2002 on Sep 19, 2017
BDSM

I was stirred from my sleep by my doorbell ringing. I quickly got out of bed and hurried down the stairs. I hadn't thought about it until I was on my way down, but my diaper was soaking wet and weighed a lot. It was so wet that a little bit of pee was dripping down my inner thigh having escaped the elastic leg band of the diaper. I had on Miss Carissa's litt...

All Day Anal Adventure

by ILuvAnal on Sep 13, 2017
Anal

Ellen and I have been married for almost two years. It was a second marriage for both of us. She has two grown children and I have three. The youngest is 17, stays primarily with his mother and is pretty independent. That gives Ellen and I plenty of alone time. Before getting married, Ellen and I spent a good deal of time discussing what had gone wrong with...

My Horny Sister-in-Law Ch. 03

by Bluepen451 on Sep 26, 2017
Erotic Couplings

Following posting of Chapter 2 of this story a number of readers expressed dismay at not getting the details of what happened between June and Herman following the couples romp in the back yard. I hadn't planned to write another chapter, but for those who want to know, here is another chapter focused on June's "Film at 11." Film at 11! God I couldn't wait....

A Need To Experiment Ch. 02

by cmbhere on Sep 16, 2017
Anal

It was mid-morning when my cell phone rang. No greeting on the other end. Just a voice, "Linda wants to see you." I quickly wrapped up what I was working on and with nervous anticipation drove to Bob and Linda's house. I rang the doorbell, and Bob answered. He looked me up and down while opening the door wide. "Upstairs. Go to the bedroom." I entered the...

My (Im)perfect Mate Ch. 02

by grgy56 on Sep 14, 2017
Sci-Fi & Fantasy

Chapter 2 Cheryl takes control. It was morning. I laid in bed. My eyes were closed as my mind started stirring. I was thinking about what had just occurred. I just purchased Cheryl, a fully functional, sexy, robot maid to cook and clean with the added bonus of being the perfect bed mate. She was a refurbished model, returned due to a bug in her old prog...