Sissy Tattoo Stories

17,774 results
Orientation
Length
Source
Infinite Scroll

Not Enough Rum in the World

by Fauxarcher on Sep 17, 2017
Mature

"Tomorrow is National Nude Day. " "Yeah, right. You're just a perverted old slob who hopes to get a peak at my cooder after midnight. And the way we're drinking, you just might. ....Ooh look. There's Jeff. He just bought a Harley and I've always wanted to ride a Fat Boy. See ya." It was a typical conversation between me and one of the younger women at the...

Quenching Thirst Ch. 02

by PutItInMyMouth420 on Jul 10, 2018
Transsexuals & Crossdressers

So there I was covered in Black mans jizz and piss, handcuffed to a handrail in a gay strip club. I was hard as a rock at this point and had realized in the midst of my humiliation that the sexiest part of all of this degrading shit was my lust for Mr. Warden. I wanted to know how it felt to truly give myself to a real man. Even though my ass was virgin, i w...

The Feminisation Initiative Ch. 02

by Slipperylock on Oct 30, 2018
Transgender & Crossdressers

The room was quiet and dark - the only illumination spilled from the Observation Room window over the eight beds and their occupants. The only sound in the room was the whirring of the machines, and the occasional muffled moan. In the Observation Room booth, the Director of the F-center fiddled with the control panel nervously and jogged her leg. The Presid...

Danny to Danielle - Beverly Awakened Pt. 03

by Deviana on Apr 13, 2020
Transgender & Crossdressers

Chapter 6 Three days had passed since that night. A few business meetings went by with little issue and most all of home life had returned to some level of normalcy. Beverly slept with me.. or, I guess I should say, I was allowed into her bed. We had our normal morning coffee and small talk about 'stuff'- work, the kids (all grown), chores around the house...

Almost Damsel Almost in Distress Ch. 03

by shawnavinyltv on Aug 24, 2020
Transgender & Crossdressers

I felt Alex moving around the bed, I figured he was going to pee, and sure enough, he came back a few moments later and snuggled back into me. I did really want to ask him about last night's adventure and if he was my mystery lover or not. Though I was pretty sure it was him, the thrill of not knowing, made me wonder who else it might have been. The thought...

My First Session with Her

by humbleslave on Sep 17, 2017
BDSM

Let me start out by describing who I was. I am 24 years old, 5'6" about 150 pounds, fair skin and short hair. I'd been cross-dressing for about seven years, and had quite a collection. I was living with a roommate, Jane, who had no idea about my hobby. In fact, I'm pretty sure she'd have been freaked out if she found out, so I'd kept it secret. I consider my...

Making Francesca Ch. 02

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

While slowly beginning to come to, Frank heard low voices somewhere off in the distance, but was unable to make out what was being said. As the grogginess began to wear off, a flood of memories came rushing into his mind; getting drunk at the bar and being caught wearing panties, being Tazed on his front porch, waking up chained to a wall in an S&M dungeon w...

My First Crossdressing Ad

by NerdySissyHippie on Dec 8, 2017
Transsexuals & Crossdressers

Growing up, I had always been a weird, lanky nerdy with long hair and a quiet demeanor. Even when I signed up to play sports in middle school, I was never what anyone would consider to be masculine and preferred hanging out and talking with my female friends than getting rough and dirty with the other boys. That's not to say I was particular effeminate eithe...

High School Dilemma Ch. 02

by LaurenWestley on Sep 15, 2017
Transsexuals & Crossdressers

Authoress's note: of course all disclaimers are still in place regarding characters etc. This particular episode is very XXX with pee scenes etc. I suggest those who don't like this kind of story not to read on. I know I make both grammatical and punctuation mistakes. I promise all of you I will try harder every time to get it right. Hey what else can a subm...

Sissification 101: Ch. 06

by silkstockingslover on Sep 28, 2020
Interracial Love

Sissification 101 Ch 06 Summary: Eric gets fucked by BBC for the first time; Joan gets black pussy. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose watching hypno-sissy porn by...