Sissy Thong Stories

50,082 results
Orientation
Length
Source
Infinite Scroll

Sissy Boy Secretary Ch. 07

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine and Tammy had been friends before the unfortunate divorce and still now maintained a good friendship. After all, it was Elaine that helped her get a job as an executive secretary during all of her school breaks, including throughout the summer break. Tammy had known that the company Elaine got her the job at was also Elaine's biggest competitor in the...

Brittany's First Time Out

by LindseyAntoinette on Nov 26, 2019
Transgender & Crossdressers

"Ugh, I messed it up again," I groaned as I tried, once again, to apply a bright shade of red to my lips. My manicured hands had been shaking all night as I got myself ready. I finished off my cherry red lips with a layer of gloss and took a step back from the mirror to review my handiwork. My grey smoky eyes and red lips shone against my pale freshly shaven...

The Challenge - Wear a Thong

by taraterry on Oct 11, 2017
Transsexuals & Crossdressers

There is something deliciously naughty about a boy wearing women's thong panties for a day, after all, the first time you wear a thong all day long, especially on a week day, you will be going about your normal routine. Whether it be to class, to work, or whatever you normally do, you will have it on all day, even when you're not fully sexually aroused. Why...

A BDSM Sissy finds Daddy Ch. 01

by Secret_sissy712 on Jul 13, 2020
Transgender & Crossdressers

As I walked back to my van after finishing up the apartment complex two men pulled up in a van and park a few spaces away. As I open my door and I take my tool belt off my shirt rides up just enough for them to get a sneak peak at the red satin thong panties popping out the top of my jeans. The fact that they do is no mistake. I wear them high and the jeans...

Pat's Panty Slave Ch. 01

by Sissyfreak on Sep 12, 2017
Transsexuals & Crossdressers

This is a fantasy story of mine. I am a 35 year old man with a wife and 2 kids who, for some reason or other, feels the need to dress up once in a while, in my wife's sexy underwear. Whilst "dressed up" I tend to fantasise about numerous things, one of which I will share now. It starts with me returning home one day after dropping my wife and the children...

Sissy Boy Secretary Ch. 04

by Hotenuf4u on Sep 19, 2017
Fetish

Arriving at the office 15 minutes early, walking past three of the other secretaries, noticing them smiling and giggling when they glanced my way. Elaine must have told them of my secret desire to wear panties. Today's choice was the white lace thong pair, which felt good as they rubbed against me as I walked. Feeling my face turning red, I walked faster to...

The Sexy Cuckold Couple Pt. 13

by cuckcpl4play on Sep 19, 2017
Fetish

Part 13 Vegas Arrival We quickly departed the plane and as expected, Master had a limousine waiting for all of us. Getting into the limo, Master asked his slut / my wife loudly enough for all of us to hear, "Is that stretched out pussy already tender and sore?" My wife immediately responded that it was hoping that Master might express some niceties or co...

Ian's New Job

by SatinSlip on Nov 26, 2018
Fetish

Authors note- this story includes non-consensual, rough, and coerced sex. As well as straight and bi-sexual sex. ************ Wendy moaned as her husband slowly licked around her pussy. She grabbed the sheets in her ecstasy. An orgasm rising excruciatingly slowly in her. Ian was great at cunnilingus. He practiced often on his wife. Delighting in the way...

Sissy Masochist

by _pdy_ on Sep 24, 2019
Transgender & Crossdressers

I'm writing this because, personally, I really enjoy writing about my sexual desires and turn ons. I find it very taboo to express these secret thoughts for strangers on the internet to see, and to be completely honest, I have a massive hard on as I write this. Well, not massive, quite the opposite actually, but you get the point. Reflecting on my previous...

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...