Sissy Piercing Stories

26,755 results
Orientation
Length
Source
Infinite Scroll

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...

Sparrows Caught and Caged

by nikisixx on Oct 6, 2020
Fetish

NOTE: This is a work of original fiction. All names, circumstances, or situations herein are purely fictional. They are not based upon either real people, governments, organizations, places, or real events. Should any parallels to real circumstances be drawn, historical or otherwise, they are purely coincidental. --------------------------------------------...

Caught in Her Panties Ch. 03

by Knightofround on Sep 16, 2017
Transsexuals & Crossdressers

As we walk down the street I wink at some of the men walking past us. Alex and Mary giggle as they see the men checking me out. I even smile at the women too. "You are such a tease Krystal!" Alex says noticing some of the women blush as I check them out. We find a nice sidewalk coffee shop and take out seats. As I sit, I feel someone smack my ass. I jump a...

Candi's Conversion Ch. 03

by CandiCumminz on Oct 3, 2018
Transsexuals & Crossdressers

Please read Parts 1 & 2 first. - Candi has had a long night and tomorrow she begins her sissy life properly. First thing? Shopping of course! - I hadn't slept well. I'd gone to bed horny and frustrated, and Lucy's screams of ecstasy in the other room weren't helping. Just as I'd got to sleep, a few hours after I'd crawled into bed, a loud phone notif...

Miss Guided

by MissMarianne on Mar 12, 2019
Transgender & Crossdressers

My name is Susan and my husband Charles, we are both 25 years old and have been married for one year. Recently Charles has been very depressed and He lost his job when the company moved to Malaysia. Lately his performance in bed has been sub-par and , in fact, he can't get it up most of the time. We feared he was becoming impotent but the doctor said the pro...

Abducted and Turned Out Ch. 03

by dawnib66 on Sep 12, 2017
Transsexuals & Crossdressers

...... So, he walked up and positioned himself at my cum soaked pussy and penetrated me, and as he did I couldn't help but moan and encourage him by saying, "Fuck my pussy". As he was pounding me relentlessly for the next few minutes, he began to tell me about himself. "I noticed you the day you moved in. I knew you were a slutty little sissy then, and I k...

Penis Shrinking from Chastity

by tinywhiteboi on Sep 19, 2017
BDSM

After losing my wife to her big dicked black lover I was pretty depressed. I knew that my 4 inch skinny penis was not big enough to satisfy any experienced women. Sure it was fine as a teenager fucking young girls, but in my mid thirties I figured pussy for me was likely to be rare. While reading pornography on the web I discovered stories about small penis...

Road Dog

by TwistedPanties on Mar 3, 2020
Erotic Horror

It all started with a bit of fun on his road trip. Bryan was en route to San Francisco to hang out with an old female work colleague, as "friends". She was a couple years older than him, 32 to his 29, and she had a great apartment downtown. Of course Bryan had wondered if she would let him put the moves on. It didn't matter if he got to hookup with her or n...

Sindys Undoing

by SindySuxALot on Sep 26, 2017
Transsexuals & Crossdressers

Lucy had been following Dr. Cornelius for months now. He had been one of the 20 endocrinologists in Orlando on her list when she started this quest, and he seemed to her to be the most likely candidate to help her with her goal. She had ruled out almost all of the others after delving into their backgrounds. From what she could tell in her research, Dr. Corn...

The Sexy Cuckold Couple Pt. 10b

by cuckcpl4play on Sep 19, 2017
Fetish

Precursor: This is part 10b of the series and it is about the fantasy we have as a cuckold couple. We have engaged in many acts of cuckoldry, but the story itself is fiction. If you are offended by this type of lifestyle than please don't read. It amazes me that we continue to get such negative comments to this series from people claiming that we are uneduca...