Sissy Tattoo Stories

17,774 results
Orientation
Length
Source
Infinite Scroll

Scorned Bitch

by lyzunchik on Sep 16, 2017
Transsexuals & Crossdressers

"I'm assuming this is not entirely business," I asked Rod when I meet him for drinks after work. He's a fellow businessperson and we collaborate on some projects. I provide technical and consulting services that augment his contracts with various businesses and government agencies. "No, not really, but I thought it an appropriate segue to get you here fo...

The Trap Ch. 05: A Proposal

by Paulateevee on Apr 13, 2020
Transgender & Crossdressers

Paula's old life crumbles but there might be light at the end of the tunnel. This is a transition story, taking our main character to the next stage of their life. As such there is no real sex in this chapter, sorry but it's required to set the scene for the next part. The usual disclaimer applied. Everyone is (well!) above the age of consent. This story...

Afro Stress Relief Ch. 02

by llts1970 on Apr 18, 2018
Transsexuals & Crossdressers

In the morning I was very nervous, what if my black co-workers had seen me in my outfit and also seen me doing those things with the other black studs, "Don't be worried Tina, it's unlikely they'd recognise you in the lighting of the club and your make-up. Even if they did I don't think you should be concerned, as I've said before it's not unusual for Afro-m...

Compromised Pt. 03

by HorribleHenry on Oct 5, 2020
Transgender & Crossdressers

COMPROMISED PART THREE CHAPTER EIGHT Park Green Private Hospital specialised, and probably still does, in mending wealthy people, particularly those with kinks. There was nothing that people did to themselves, or each other, that fazed the dedicated staff of the hospital. A patient with a torn arsehole caused by anal sex was very low down on their list of...

White Gurl Pimped in the Hood

by Stephisissycd on Sep 11, 2017
Group Sex

After Black Mike made me his bitch, showing up at motels all over town dressed like a street hooker, he sent me a text one day. "Hey bitch. I need you to dress really slutty, get smooth and totally clean, and meet me at the motel at 6th and Los Angeles st." I knew where that was, right by skid row. My pussy started to throb thinking about what black mike h...

Girl's Night Pt. 03

by DifferentBreed on Sep 14, 2017
Fetish

Fisher climbed the stairs slowly, wary of the quiet that hung over the upstairs. As he hit the landing a soft moan emanated from the bedroom and his heart raced as he entered the doorway. There, framed in the soft light of the bedroom lamps, was Sophie kissing another woman. Her crisp white shirt was unbuttoned, exposing the top of her supple breasts, and gi...

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...

The Journey Pt. 01

by MissYellowPanties on Sep 13, 2017
Transsexuals & Crossdressers

Part 1 The Journey. I sat in the back seat of the car, my legs stretched in front of me and crossed at the ankles, the short skirt I wore barley covered my panties, and I could feel the cool leather of the seat press against my legs. I smiled at the reflection of the drivers hungry eyes in the rear view mirror, longing, lust, and power, mixed together in...

Slut Sisters Say Hello

by Nellie_Kay on Sep 14, 2017
BDSM

So, my Mistress had summoned me to her office. This was unusual; I was normally called to her cellar where all the tools that she needed to correct me were readily available. Also, in the dungeon were the clothes that she made me wear. The nylon, pink baby doll nightie, the blue gingham pinafore and ,of course, the collar that she made me wear during my puni...

Jesse's Journey Down a Rabbit Hole Ch. 15

by sadkins116 on Sep 14, 2017
Illustrated

I want to thank everyone for reading, voting and commenting on our story. I submitted the first six chapters, and Rebeccasm submitted chapter 6 through 12. I will be submitting chapters 12 through 18. We have both worked hard on this series and as such both deserve to share the postings. Hopefully you will visit both of us and enjoy the series. As I mention...