Dildo Sissy Stories

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Caught en Femme

by RisqueRavisher on Sep 12, 2017
Transsexuals & Crossdressers

This is the very first story I've written and uploaded here. I'm sort of nervous because it's probably not the best. Don't forget to rate and whatnot. Give me feedback/tips on things to improve on. I'm always looking to improve. Anyway, enjoy xx ***** "I'm going to be home a little bit later, babe," my wife, Annie, called from the alcove. "I'm going out wi...

Cockland Island Pt. 06

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

I woke up and I was sucking that realistic dildo cock like a soother and it was so weird and right and made me smile as I pulled it out trying to make my lips do the pop you can do sometimes with suckers. I giggled and did it a few more times then pumped it in and out of my mouth trying to get that dick lips feeling going on. That's a sexy sissy trick, all...

Oh Jack!

by Gemsissy on Sep 15, 2017
Fetish

"Oh Jack! Can you come over and help me a minute?" I stopped in my tracks and looked over. Samantha lived in the condo next to mine and was very friendly. I'd introduced myself when she was moving in and ended up helping her all afternoon. We talked easily and I'd started thinking of asking her out. We'd even been flirting a little bit here and there. She w...

My Bestfriend's Girlfriend

by Shauna_Wood on Jul 9, 2019
Transgender & Crossdressers

When I was in my early 20's I used to play a lot of online video games. First person shooters, mostly. The Battlefield series, especially. I had started playing games online with a guy named Chris who had gone to high school with my ex-fiancé. He and I had met through her and had really hit it off. We had remained close even after she and I split. He lived u...

My Submission to a Real Man

by gbr2004 on Dec 28, 2017
BDSM

This is total fantasy and would never do many of the things I discuss. If not into really kinky play, humiliation, verbal abuse, and forced fem and strong discipline, please pass on this story. For all you other submissive boy and dominant men hope you like my fantasies. ***** MY SUBMISSION TO A REAL MAN It was our first actual meeting. We had emailed bac...

Card Shark

by Turned on Sep 14, 2017
Loving Wives

I returned to my hotel room from a poker tournament and realized I'd forgotten my key, so I knocked. After a few moments the door swung open and my pretty, young asian wife was waiting for me behind it. "Hi honey," she said, giving me a very strange look, "How did you do in your poker tournament?" "I did ok. Third place. I made a little money," I said, s...

Black Sissy For White Mistress

by Samuelx on Sep 16, 2017
Interracial Love

Right now, I'm lying in my king-sized bed. And I'm getting fucked in the ass. Picture this, if you will. A big and tall young Black man of Haitian descent getting fucked by a tiny, blonde-haired white chick wearing a strap-on dildo. My name is Stephen and this is actually my idea of heaven. I live in the Vanier sector of the City of Ottawa, Province of Ontar...

A Prom Queen Fantasy

by bluesbirds on Jul 15, 2020
Transgender & Crossdressers

"Aww, isn't this little blue number cute?" Tanya squealed from the other side of the rack. I flinched hearing her voice; we had been shopping for almost 3 hours without a break. This was the first time I had gone shopping with Tanya since she found out about my crossdressing fetish. "Come to this side - let me hold it up to you," she demanded. I meekly co...

Feminizing First Step Ch. 03

by antares34 on Oct 21, 2019
Transgender & Crossdressers

(All characters are age 18+) *** I felt like I was losing control. My body and mind were becoming less and less masculine with every passing day. And I was secretly ENJOYING it. I couldn't help myself. Every time I looked in the mirror, I found myself loving the ever-changing reflection. First, my dyed pixie haircut. Then, my bikinis. Then, my nose, ear, a...

Sissy Meets Master's Male Fiend

by sissysubTiffany on Apr 23, 2019
Transgender & Crossdressers

This is part 5 of my Master turning me into a sissy and his woman. *** Master Gene has now taught me that when I around him or his friends I will dress and act like a sissy girl thinking of being one for real. He now expects me to arrive at his house as Tiffany. No longer treated like a man I will only go by Tiffany and be his girl. I now spend every weeke...