Sissy Piercing Stories

26,755 results
Orientation
Length
Source
Infinite Scroll

Chrysalis of Kirsten Ch. 03

by kirstensubts on May 7, 2019
Transgender & Crossdressers

My name is Steven aka Kirsten. This story is about how I went from a closet cross dresser to becoming a full time transgender slave. This story is mostly true, based on my journals with dramatic license to make it more exciting and readable. Names have been changed. This is who I am. A special thanks to Shy Girl Whore for her help with polishing this story!...

Jerry becomes Jill Pt. 05: July 4th

by gasissynora on Apr 27, 2020
Transgender & Crossdressers

Jerry becomes Jill: Part 5: July 4th Week End This is the fifth part of my story about how I became Jill. After having started female hormones, Jill is introduced to group play by Mistress Rikki. The Fourth of July is on Monday and that Thursday evening at dinner Mistress gives me some information about the holiday weekend. She says, "Tomorrow you are done...

Truth or Dare Takes a Turn Pt. 01

by Cutiepie183 on Sep 14, 2020
Transgender & Crossdressers

I'm sitting at home on summer break, just a few weeks after graduating high school. I hear my phone buzz and glance over to take a look. I can't believe what I'm reading! "Luke Elwood has invited you to his event: graduation celebration party tonight at 8pm." You see I was never really one of the cool kids in high school - I never really had any friends but...

The Wedding Ch. 09

by betamale08 on Apr 1, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 9 – Coerced, Consumed and Consummated... After wrestling my Uncle John out of his suit and laying him out on his back, I knew his passed-out routine was all a farce as he looked to me winking with a smile before going back into his pretend-coma... Faking it in front of Patti and no doubt doing so in the want of stay...

Mistress Emma's Revenge

by sissymissyct on Oct 15, 2017
Fetish

Hi I'm Ken. Well I was, now I'm called Brenda. Here's a bit of my story for you. I hope you don't make the same mistakes I did. Because until I got caught misbehaving by my mistress, life was pretty good. At 38, I had a great job as an office manager in charge of 25 or so employees, mostly women, a really good salary, a nice office and plenty of job securit...

Pierced Desperation

by justincbenedict on Sep 25, 2019
BDSM

Ervin felt his cock, bouncing on the leaden testicles, as he got out of his car. It was such a funny old house that Isely lived in... She charged by the hour, claiming on her taxes that she appraised antiques. But her credit card "charger" was next to her bed... It had been quite a week, Ervin reflected as he climbed the steps onto Isely's porch. The Pr...

Opening Him Up Ch. 02

by humbleboy on Sep 12, 2017
BDSM

Amy was looking down on her husband, watching the large life like phallus enter into his mouth. She got the strap-on in four inches and then Tim started to choke. "Relax my little bitch and try to think of swallowing my cock." Tim tried and he eventually gained another inch, but for fear of this new sensation he wouldn't go all the way. "Don't worry, I'm goi...

A Sissy (S)exercise Fantasy

by darkheathyr on Sep 16, 2017
Transsexuals & Crossdressers

The following tale of sexual depravity contains adult material. If you are under the legal age for your area (generally 18 or 21), or object to explicit sex, stop reading NOW. Otherwise, if erotic situations and taboo acts turn you on, then please enjoy yourself. The characters and situations are, of course, completely fictitious. Feel free to post or archi...

On Your Knees Ch. 05

by JinkiesFarie on Sep 16, 2017
BDSM

He grabbed his shaft as he sat in his office, shame burned in his cheeks. This was his place of work, but the thoughts of Nicole were so powerful, so overwhelming--he couldn't help himself. During his lunch period, he had locked himself in there instead of taking the usual route into the school's cafeteria. Nicole penetrated his thoughts. In his little fan...

Sissy Stretching for Princess T Pt. 02

by Subboi23 on May 12, 2020
Fetish

Once I get home, I practically run to my room. Sitting in the car has pressed my plug deep into my ass and now my running causes it to wiggle around while still deep inside me. "Home Princess," I text as soon as I close and lock the door to my room. I quickly peel all my clothes off except for my panties and get on my knees. My toy is retrieved from a draw...