Sissy Piercing Stories

26,755 results
Orientation
Length
Source
Infinite Scroll

Brittany's First Time Out

by LindseyAntoinette on Nov 26, 2019
Transgender & Crossdressers

"Ugh, I messed it up again," I groaned as I tried, once again, to apply a bright shade of red to my lips. My manicured hands had been shaking all night as I got myself ready. I finished off my cherry red lips with a layer of gloss and took a step back from the mirror to review my handiwork. My grey smoky eyes and red lips shone against my pale freshly shaven...

Neighbourhood Terror to Sissy Pt. 22

by Fibaro on Jul 6, 2020
Transgender & Crossdressers

Chapter 24 "Okay Marcy, now get back up and Minthe back to the vanity table. Jutht like it'th important to know how to apply makeup, it'th important to know how to remove it ath well. After all we don't want you developing a bad thkin cauthe of all the makeup you're uthing." Stephanie ordered not even giving Marcy a few minutes to deal with what had just ha...

How Friday Got A Reputation

by alice247 on May 11, 2020
Erotic Couplings

How Friday got a reputation "Oh, my fucking God!" Sissy McDowell gasped as she reached into my boxer shorts. "That's all you?" I pulled my face back from her neck and straightened up. "Yes. What's the matter?" I responded defensively, certainly unsure of myself and her reaction now that I had my hand on first base. "You're fucking huge!" She exclaimed wit...

Her Male Wife

by Zippeduptight on Nov 6, 2018
Transgender & Crossdressers

Sometimes I wonder how I got into this mess. The answer is obvious but it usually comes during the day when I pee. Carla's orders are to sit when I pee. I lift up my skirt, and tuck the exposed chastity device down, and relieve myself. Just like now. The shiny pink pvc sissy maid outfit she bought for me is locked on at the neck. I stand up and flush walking...

Driving Her Home

by bored_doe on Sep 16, 2017
BDSM

Alan smiled at the perky blonde college student in the passenger seat of his sedan. "So Catelyn, have you figured out what your major is going to be yet?" "Mister Denny, are you wearing makeup?" It wasn't a question, it was a challenge. Her brown eyes watched him without flinching, waiting to see how he'd respond. The question was so unexpected, it knifed...

Girl's Night Pt. 09

by DifferentBreed on Sep 14, 2017
Fetish

*author's note* To the fans of this series I appreciate your patience as the chapters have been a long time coming. I am having difficulty fleshing out the club scenes that were to follow. I wrote this brief interlude which takes place immediately after the couple leaves the mall. Hope you will enjoy it. Thank you all for the positive encouragement and the...

Becoming a Sissy Slave

by mikhaylacumme on Sep 16, 2017
Transsexuals & Crossdressers

He gave me the choice. He had programmed me for a week and knew which way I would probably choose, but he gave me the choice. I could get out. Or I could continue. It was up to me. On my knees or out the door. It was that easy. Now I had to choose. I guess I should backtrack, first. You might be scratching your head saying 'what choice?' Let me start...

Girl's Night Pt. 04

by DifferentBreed on Sep 14, 2017
Fetish

"You want to cum too, don't you bitch?" Sophie said. "But pleasure is only reserved for Mistresses and Dommes. Not sissy whores like you." Sophie looked down at him, grinning evilly, turned on by the lips descending her body and the sight of him kneeling there in sexual servitude and agony. She let her hand fall lightly on the back of Jenny's head as she fel...

Penetrated by a Woman

by Xavier_271 on Sep 12, 2017
BDSM

With a smirk she forces a ball gag into my mouth and secures my wrists and ankles tightly in restraints that are anchored between the doorframe and door in such a way that I am entirely helpless and exposed. I am a 23-year-old lean, athletic, blond-haired male who is going to school in Boston. I have been interested in bondage and submission for some time, a...

Auntie knows

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

You are in a converted loft as a shiver ran through your skinny, hairless body. You survey the pretty maids outfit lying majestically on the guest bed. Made of a sensible black polyester with short, puffed sleeves trimmed with white lace, dainty yoke neck, tailored Basque type top, nipped waist with a bottom skimming short lacy skirt. Your pulse quickens as...