Sissy Strapon Stories

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Orientation
Length
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Infinite Scroll

How I went from Domme to Slut Ch. 06

by Ms_Allison on Jun 26, 2018
BDSM

I would like to thank the darlin mymantoy999 for his editing and insight and in particular keeping my math and thought process straight while writing these! ***** As amber had suggested she and I settled into our new normal relatively quickly. Now on top of waitress duties every other week, house cleaning trips and the random frustration amber experienced...

Me & My Wife Are Sisters Now Ch. 02

by gayindia1980 on Sep 16, 2017
Transsexuals & Crossdressers

This story is in continuation of my last story Me & My Wife Are Sisters Now Ch. 01 ***** Next morning, we both slept quite late then our usual time, I don't know about Shivika but I was still feeling cum inside my ass. Last night my wife, Shivika was fucked by 2 sexy men in a 3some and then one of them fucked me really hard. Shivika woke up around 9:30 an...

Barbie's BBC Beginning

by jacki697 on Jun 9, 2020
Transgender & Crossdressers

I had always been curious about men. I had always wanted to experiment but alas I was way too scared of being "gay" to ever follow through on any of my urges. Chalk that one up to 18 years of living in a conservative Christian community. Instead I left my sexual urges to the alone time I had to indulge in my other fantasy of crossdressing. I loved the thrill...

Neighbourhood Sissy

by Abusedbyfuta on Feb 7, 2019
Fetish

Your a young man in his late teens. Average build, average height, brown hair, green eyes. You know the type never stood out in a crowd for your good looks but never scared children when you went to the store either. Having just finished high school ou decide to start doing odd jobs around the neighbourhood to raise some money. Maybe it was college, maybe it...

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A special Christmas

by Chuveiro on Dec 17, 2018
Fetish

It was already December and I was home alone. Mommy had gone shopping all things she would use on Chiristmas dinner, which would be at our house. I went to my room and got my clothes and toys. I was a sissy, but nobody in my family knew that. The only person who lived with me was mom but she was so old she couldn't notice anything. I dressed up and started t...

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My Girlfriend Made Me a Sissy Ch. 02

by libertinaXx on Sep 25, 2017
Transsexuals & Crossdressers

Thank you to everyone who sent me messages about the last story, I've tried to include things people wanted to see in the sequel. Hope you enjoy ---------------------------------------- I woke up, stretched out and smiled as I felt the familiar sensation of my girlfriend's panties rubbing on my cock. The feeling instantly brought back memories of the night...

Becoming More Feminine Pt. 02

by bottumguy84 on Feb 11, 2019
Transgender & Crossdressers

(Editor's note: This one isn't as long as my last story, the main character is getting a first name, and I'm going to incorporate a few requests from readers in the last story) *** Jason, Dan we're back. I barely was able to open my eyes when I heard Jen say, "Dan"? I finally woke up enough to realize what happen, Jason's arm was draped around my waist an...

My First Session with Her

by humbleslave on Sep 17, 2017
BDSM

Let me start out by describing who I was. I am 24 years old, 5'6" about 150 pounds, fair skin and short hair. I'd been cross-dressing for about seven years, and had quite a collection. I was living with a roommate, Jane, who had no idea about my hobby. In fact, I'm pretty sure she'd have been freaked out if she found out, so I'd kept it secret. I consider my...

Trixie's Chastity 02

by trixie47cd on Sep 13, 2017
Transsexuals & Crossdressers

Tammy, the maid took me away to shower quickly in an upstairs bathroom. I was only given about 3 minutes to scrub off the caked on sperm from the guests at the party, then Tammy helped towel me off and completely re-do my makeup. Goddess had packed a dark brown wavy wig that gave me a secretary or teacher look, but the navy pleated skirt was short enough t...

Fantasy to Reality

by CuckoldDesires on Sep 15, 2017
Transsexuals & Crossdressers

I faded in and out of consciousness. My body was numb and I waded through a sea of words and images that filled my mind, struggling to focus on anything specific. Slowly I began to wake but my eyes did not open and my body remained numb. I searched for my memory, I knew it was there but I couldn't reach it, I was entranced. My name and past eluded me as I s...