Sissy Thong Stories

50,082 results
Orientation
Length
Source
Infinite Scroll

Center of Attention Ch. 02

by Seethru57 on Sep 16, 2017
Group Sex

Disclaimer: All characters in this fictional story are 18 years or older, and all names are ficticious. This is a continuation series. Debbie Ross was sitting on her bed, writing in her diary about the events of the previous night. She wanted to keep those memories, and hoped to add new ones to the lusty events at Mr. Collin's home. Her thoughts were interr...

Caught In Lingerie

by hicutlover on Sep 26, 2017
Transsexuals & Crossdressers

I was driving home from work and all day I had been extremely horny. I had unbuttoned my pants and was stroking my cock in my purple nylon thong. I loved this thong. I could see the outline of my cock and the shape of my cock head in these panties. It was making me harder. All day I had been fantasizing about taking a cock in my boypussy and couldn't wait to...

Second Meeting with Master Gene

by sissysubTiffany on Jun 19, 2018
Transsexuals & Crossdressers

Friday evening comes finally as this was the slowest week of my life waiting for this day to get here as so looking forward to tonight even though I am still a little leery about becoming a sissy submissive of Master Gene's. I have shaved my entire body and sent pictures for proof as he demanded and now sitting in a pair of my pink with lavender lace bikini...

Finally Found Her Ch. 02

by hyperpress on Aug 18, 2017
Fetish

Switching from "you" to "she" for effect. She moved from the vanity chair to the bed. I've covered the bed with pillows and the room is lit with candles. "You're such a good little girl, now go get us a bottle of wine," she is lovely on the bed. I'm standing at the bedside and your mouth is irresistible and I bend at the waste to kiss you. Softly we kiss a...

Another Submissive Slut Ch. 08

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

I had hurried home from the porn shop only to run into Derrick in the lobby of the building. Lucky for me his mother emerged from a hallway and he could only cast me evil looks. His mother however took the opportunity to lay into me about my behavior and image. I realized as I slunk away from the verbal abuse that the chain around my waist was probably visib...

The Awakening of a Sissy Pt. 03

by sissyjolie4u on Jan 20, 2020
Transgender & Crossdressers

As i was watching the video of Mistress and I for the 3rd or 4th time, my phone rang. "Hello my sweet Joey, how are you doing? I so enjoyed spending our time together, I'm so proud of you and the progress you are making. Are you still in your pink bra and pantie? That is such a sexy look for you, it makes you look so soft and feminine. Tomorrow we will build...

Discovering Amber Ch. 08

by Ms_Allison on Apr 23, 2019
Transgender & Crossdressers

Mistress notes: After 8 or so months of going to the club twice a month amber became a welcome regular and a great dancer. Actually, she danced better in 5" heels than in men's dress shoes, which I obviously teased her about often. I also made sure to keep her embracing her comfort level with being groped while dancing. Her dance partners soon learned her li...

Jasmine - Sissy Slut Transformation Pt. 01

by BillyBaroo4you on Jun 1, 2020
Transgender & Crossdressers

A Sissy Cumslut Transformation Part I - The First Taste (of cum) Nervousness crept into his mind like a snake, slithering its way down toward his stomach. He felt scared, worried about the night ahead, worried about how this one night would change his young life forever. His gentle hands began to tremble as he applied the hot pink nail polish to his finger...

Sissy for the Family

by sissyboi4daddy on Aug 21, 2018
Transsexuals & Crossdressers

Hi, my name is Isaac. I'm 21 years old, Asian and a child of divorce. My father decided he wanted nothing to do with me the moment I was born, and my mother held 2 jobs to raise me. When I was 18, she decided she had enough of the hard life and remarried. She remarried Jack. Jack was a white, bordering on obese man, who was 12 years older than my 42-year-o...

Creating Ginger Ch. 04

by Ms_Allison on Jun 8, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into, cuckoldry, dominance and submission. If these are not topics you are interested in, then please move along. In the below story I refer to the male character several ways but try to maintain a consiste...