Pantyboy Stories

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Kitty's PantyBoy PrickTease Pt. 02

by KittyZateez on Feb 6, 2018
Fetish

Kitty's PantyBoy has been naughty. Very, very naughty! And now, her PantyBoy will be punished with a nice, yummy prick tease. Now then...first a little recap. Where did we leave off? Oh yes, right here: me, your very own busty blonde Barbie-doll girlfriend, all dressed up as a tantalizing cock teaser in a black vinyl dominatrix outfit. I've got shiny blac...

The Pantysissy Diaries Ch. 01

by JPantyboyVSL on Sep 2, 2017
Fetish

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. ***** Jay was on his way back to New York from a weeklong work conference in Chicago. He decided to take Amtrak back to NYC. He got on the train in Chicago and noticed a hot young blonde woman in her 20s s...

Panty Boy Halloween

by pantyboy4mistress on Sep 11, 2017
Transsexuals & Crossdressers

Part One An Invitation of Sorts It had been seven months since he had met his Mistress. What started as 'just a job' had turned into a life-altering adventure. Everything he did now was controlled by the woman he called 'Mistress.' Everything. He had always been fascinated by panties. Mistress told him that all men are, that all men are jealous of the pr...

Kitten: A Pantyboy Story

by pantyboy4mistress on Sep 13, 2017
Transsexuals & Crossdressers

It's easy now to look back and play armchair psychiatrist and see where my fetish for school uniforms and cute cotton panties started, but it wasn't until I met MISTRESS that I realized exactly how deep that fetish was ingrained in my mind and soul. Mistress knew I was a pantyboy after the first few seconds we met. Or so she likes to remind me. She didn't n...

Ms. Choi Trains Pt. 01

by chenwanli on Sep 12, 2017
Fetish

Sunday morning began as every morning over the last month did. The light snapped on and Michael awoke- exhausted, deliriously horny and frazzled from his perpetually light sleep, his body pulling against the ankle and wrist cuffs securing him to the double bed as the vibrating butt plug finally stopped its relentless stimulation of his prostate. Ms. Choi rem...

Kitty's PantyBoy PrickTease Pt. 01

by KittyZateez on Feb 6, 2018
Fetish

So, tell me - would you like to be my PantyBoy tonight? Would my PantyBoy enjoy a nice, fabulously erotic prick tease session with me? Hmmm?? If so, perhaps it would help your decision if I dressed up in the black vinyl dominatrix outfit I described in my "Kitty's Sensual Prickteasing" story...would you like to see me all sexied up like that? All righty th...

The Bet Ch. 04

by ssnatch on Sep 19, 2017
Fetish

I closed the door to our hotel room and latched the lock. Sarah ordered me to strip down to just the undergarments that she had provided me. "Lay down on the bed, on your back," Sarah instructed. I quickly complied, eager to please her. Whatever she had planned, I was more than ready at this point. She reached into her luggage, and pulled out a blindfold ma...

Sissy Panty Handjob

by CrossdresserCaitlyn on Jun 19, 2018
Transsexuals & Crossdressers

When I woke up in the morning I saw my girlfriend getting ready for work. She sees me awake and reaches out and rubs my penis outside my panties. While rubbing me she tells me if the house was spotless when she got home sissy would get a special treat tonight. She let's go of my dick, smiles and leaves for work. Still hard I jumped out of bed immediately a...

The Bet Ch. 03

by ssnatch on Sep 19, 2017
Fetish

We arrived in New York, and after gathering our luggage, we hailed a cab, and made our way into the city. Sarah had booked us a room at nice boutique hotel in mid-town. When we got into the room, Sarah ordered me to strip down to my panties. I stood in the middle of the room, in front of the king sized bed as she walked slowly around me, looking me over. She...

Operation Pucks and Panties Pt. 01

by JPantyboyVSL on Aug 18, 2017
Fetish

I grew up a hockey fan. I've always loved the sport, and I've always had a fetish interest in being a woman, as well as serving women. I've always wanted to dress like a woman (more specifically, I have a fetish interest in wearing women's nail polish and wearing women's underwear). Everytime I buy the SI Swimsuit, issue I picture myself wearing those gorge...