Pantyboy Stories

87 results
Orientation
Length
Source
Infinite Scroll

Business Trip - Day 01

by pantywriter on Dec 16, 2019
Transgender & Crossdressers

Day 1 At four-thirty in the morning, when you and your girlfriend are both up and screaming at each other to find this and that, because you both have flights leaving the airport within ten minutes of each other, and within ten minutes from six, sex is the very last thing on your mind. We woke on time and were generally getting along well but Emma was havin...

Casey's Submissive Journey Pt. 14

by corduroysissy on Aug 7, 2018
Transsexuals & Crossdressers

"Come over here princess, it's time for you to be my husband's little fuck-bunny." The time had come. He obediently walked over and she instructed him to drape himself over the stacked pillows, then bury his face in the corduroy pants on the other pillow. He did, and between the pillows, the bedspread and Susan's pants his whole body was now rubbing agai...

Out of Gas Ch. 02

by Pantyboy1204 on Sep 13, 2017
Transsexuals & Crossdressers

Pt. 2: Heather I had just been through quite an ordeal, accepting help from a stranger had not gone at all like I thought it would and now here I was in a strange city being held by one of the men who had just gave me a serious fucking while wearing baby pink silky boy shorts with pink lace all over them waiting for a girl that was supposedly going to he...

Jennifer Monroe & the Ladies Ch. 03

by corduroysissy on Jan 31, 2018
Transsexuals & Crossdressers

Debbie gave Miss Jennifer's boot one last kiss, took a few seconds to straighten out his dress, then walked over and knelt submissively next to Patty in front of Miss Marsha. She let Patricia continue to suck her dick and lit a cigarette, she didn't even look at him, in fact she totally ignored him for several minutes. She did however blow smoke in his face...

Madam Molly Pt. 02

by corduroysissy on Feb 11, 2019
Transgender & Crossdressers

Molly & Jessie's conversation lasted about twenty minutes, and by the time it was over she'd made it quite clear that when it came to obedience her expectation were very high. She then informed him he was going to be her little slave-boy and amuse her for a while. When she was ready to get laid she'd summon her cuck Tracy back and Jesse would resume his boyf...

Casey's Submissive Journey Pt. 02

by corduroysissy on Dec 14, 2017
BDSM

Debbie's eyes bulged when he looked up at Angelina, and his best friend smiled back at him. "This is my Angie, Debbie, he wanted to watch you cream his jeans." Looking through the make-up and wig he could barely make out the face of his young buddy. Casey was blown away by how good Jamie looked as a girl, he was pretty as all hell. The make-up looked perf...

Behavior Modification Institute Ch. 03

by NancyPan on Sep 12, 2017
Fetish

I had often looked for panties just like the ones I had found as a teenager in mother's dresser drawer. But nothing just like them seemed to be made these days. I had even looked at vintage panty sites on eBay without any luck. So to see this pair, so similar, so alike, so silky, sooo...of course I wanted to put them on. I was in a bit of a quandary at the m...

Chastity Keyholder Sexting

by her_pantyboy on Aug 31, 2017
Fetish

This morning my Keyholder was at work and i was 1200 miles away locked in a CB6000s chastity cage with a plastic numbered lock (485807). i was telling Her how much i missed Her and we were just talking about everyday life, when in the background i heard one of Her male coworkers bring Her a cup of coffee. As he gave it to Her, She said, "thanks bitchboy". i...

A Look Into My Mind: Uncle Sissyboy Ch. 04

by rickiee_2002 on Sep 25, 2017
Fetish

I couldn't believe it ... I was finally going to be able to have sex with my niece. She is so gorgeous and sexy. She is everything I could want. Young, thin, tall, beautiful, full pubic busy, sexy ... WOW. I leaned forward and touched the tip of my tongue to her super wet pubic bush and then the tender small lips of her pussy. There was a white liquid oozin...

Panty Posers

by EROTICbearscribe on Jun 1, 2020
Transgender & Crossdressers

PRIVATE PANTY SESSIONS Ch. 01 "Wait! What? Say that again." Doug, my roommate of two years, closed his eyes and took a deep breath. Tension hung heavy in the air. I allowed him to take all the time he needed to explain even though my mind was racing the way it does when your entire world has been turned upside down. I could see he was struggling. It look...