Sissy Thong Stories

50,082 results
Orientation
Length
Source
Infinite Scroll

Pat's Panty Slave Ch. 03

by Sissyfreak on Sep 16, 2017
Transsexuals & Crossdressers

Having been humiliated for a second time, I thought things couldn't get any worse, how wrong could I be! I was sat at home one day, kids at school, Wife out shopping, when there was a knock at the front door. Jo was standing there with a carrier bag. She threw the bag to me and ordered me to put on the items within, then come to her house next door. I looked...

Auntie Jean Drummond Lloyd

by Sissy Adele Howells on Aug 31, 2017
Fetish

I had been caught red handed. My kinky secret was now known by the stewardess of my local club. At 45 years of age, without a girlfriend, my world was about to change. Of course this was a fantasy dream, but everything was so real. Stewardess Jean Drummond Lloyd was 58 years of age. Sixteen stone of obesity, with short, blonde, curly hair. This was going gr...

Feminizing First Step Ch. 07

by antares34 on Aug 24, 2020
Transgender & Crossdressers

I was meeting my internet "daddy" for the first time today. His last text message to me had been very clear: tie myself to the motel bed and wait for him to arrive. I stared at the antique bed with its black metal frame and headboard, wondering to myself if this was such a good idea. This rundown motel had been hard enough to find. I had never been to this...

Total Drama Island

by Yelawolf on Oct 12, 2019
Fan Fiction

(Every character in this story is 18+) You step off the boat last. You see all of your competition. Most of the chicks looked pretty damn hot. Especially the cool goth chick. The guys mostly seem like idiots besides a tough-looking dude with green hair and piercings. You walk on the dock seeing the poor condition of the island for the first time. You didn't...

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A Big Surprise!

by rj1774 on Jul 6, 2020
Transgender & Crossdressers

As a man's sexual desires come to light this story features, femdom, pegging, crossdressing, and dating a TS woman. Please share any constructive criticism or where to take a next chapter. I hope you enjoy! **************** My sweet, caring, brilliant girlfriend, Stephanie, and I have been dating for a few months and we decided to plan a long weekend get a...

Feminized by My Girlfriend Ch. 02

by Trinni69 on Sep 25, 2017
Transsexuals & Crossdressers

I followed Brook and Linda out of the spa onto the sidewalk and I looked around for the limo but it was no where to be found. As the girls started walking down the street and talking to each other, I asked where the limo was. Neither of them responded and just kept walking. I followed behind as closely as I could and hoped no one would notice me. Luckily it...

Jacki's Journey into Sissyhood Pt. 03

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

This is the 3rd installment of the Jacki's Journey series. I'd like to thank those who were nice enough to add comments and feedback on the proceeding stories. I'll try and keep them cumming. ***** I had a couple days to evaluate Steve and Laura's offer and I was no closer to a decision than I had been. I went back and forth on the verdict. How was I goin...

Sissy Boy Secretary Ch. 03

by Hotenuf4u on Sep 19, 2017
Fetish

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you! After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in...

Sissy Hotel Play

by elliotsconfessed on Dec 24, 2018
Fetish

It was a Friday afternoon and I was feeling a little bored and some what curious... I had spent the last hour or so watching porn, but not just the usual straight type of porn I'd usually watch... For some reason I had an urge to watch men fuck other men and have guys dress up as girls and fuck themselves with toys! I was so turned on and a little confus...

Submitting to Dominance Ch. 02

by _pdy_ on Sep 28, 2020
Transgender & Crossdressers

This is chapter 2 in the Submitting to Dominance series where our heroine Perry has some alone time with the man who will take her for himself. I welcome all comments, criticisms, suggestions, and feedback, but in general I just write these stories for fun so please take that into consideration. Thanks and I hope you enjoy! --- The drive to Perry's was ex...