Sissy Ass In The Woods Stories

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High School Dilemma Ch. 01

by LaurenWestley on Sep 15, 2017
Transsexuals & Crossdressers

I should have known better. It was such a stupid thing and it didn't even work out. Here I was graduating from High School. I had just turned eighteen and it was the last week of school. How could I have done it? Why did I take the chance? Kelly was probably the prettiest girl in school. Her hair was long and blond. Not much different then mine. Actually we...

Bitch

by Dennis_St_John on Sep 19, 2017
Transsexuals & Crossdressers

'I am ready, Sir.' I texted on my cell phone. 'Room 28.' A few moments later, the cell phone pinged and a return message appeared. 'You know what to do -- I'll be there very soon.' I took a shuddering breath and looked at myself in the bathroom mirror. An angry frown marred the soft made up sissy face looking back at me, framed as it was by dark straight h...

Making a Sissy Jock Pt. 02

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

I stared at Robin's card for an hour sitting in my truck completely freaked out and every time I touched my lips I felt that friction of Robin's cock. I tasted him. I got slammed with the realization I drank his cum and it was inside of me. I sucked cock and drank cum and just like the sissy porn stuff said I liked it. I was beyond freaked in going to th...

Appointment by Card Only Ch. 01

by Sputnik57 on Sep 17, 2017
BDSM

She had always been so vulnerable, growing up with the other boys it was so obvious she was not like them. Now in their late teens as adulthood announced itself to the others by adorning them with bodily hair and a developing musculature, they laughed at the soft hairless form of the one who was well known to them, but only from an external perspective. The...

Dry Valley Ch. 20

by RedHairedandFriendly on Sep 18, 2017
Chain Stories

Finishing Touches Three days had gone by since the break-in and attack on Jessica and Bailey. The women had been moved to the Walker Ranch, much to Missus O's soft muttering. But she knew the ranch was the place the girls needed to be to recuperate, she was however out there every day just to ease the burden on her friend Sissy, though Sissy didn't find it...

I Am Sissy

on Apr 29, 2025

Hi boys, my name is Eli but I now go by Eve. I finally decided to come out of my inner closet and allow myself to be what I really want to be… a pretty sissy boi that craves cocks, lots of cocks everywhere in or on me. I have always been a small and slender boy, even in high school before I graduated, I looked like I was younger, I even had some of my teache...

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A New Spin on Role Playing Games

by shawnavinyltv on Sep 18, 2017
Transsexuals & Crossdressers

I've always been something of a geek. I love sci-fi and fantasy books and movies; I can recite countless bits of useless trivia back to you about all kinds of movies. So, it was no real surprise that I took to role-playing games, or RPGs, as we like to call them. You know the kinds, Dungeons and Whatnots, all that kind of Tolkien-esque stuff. I had a couple...

The Dominatrix Order Pt. 02 Ch. 02 - Cuckold

by Jwwsmith on Jan 29, 2019
Transgender & Crossdressers

And so the days and nights passed at Johanna's home. With Sissy Slut gone, there were no slaves remaining who possessed any culinary skills. So Pomona took it upon herself to cook a fine breakfast every morning for Johanna, as a way to repay her for her hospitality. Pomona would wake early each day, fire up the wood stove, and cook a delectable meal of bacon...

Cock Sucking Jail Whore

by RobinTVDaniels on Sep 15, 2017
Transsexuals & Crossdressers

I've always known that I was not meant to be a guy. Being sexual curious I would look at porn mags like any one does. At first it was just magazines with pictures of naked woment. It was when I ran across my first Hustler magazine that my life was changed forever. Seeing pictures of studly guys with big hard dicks and women on their knees about to suck or be...

Thailand Sissy

by Xxxdollxxx21 on Apr 22, 2025

I really just wanted a vacation away from my ex wife that I was divorcing, from my dead end job, and my annoying ass boss. This trip was supposed to be fun. Site seeing across Thailand, their rich, beautiful locations and religious temples. The beautiful scenery I had seen after I got off the flight and rode to my resort had vanished into these deep woods. T...

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