Boypussy Stories

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Caught In Lingerie

by hicutlover on Sep 26, 2017
Transsexuals & Crossdressers

I was driving home from work and all day I had been extremely horny. I had unbuttoned my pants and was stroking my cock in my purple nylon thong. I loved this thong. I could see the outline of my cock and the shape of my cock head in these panties. It was making me harder. All day I had been fantasizing about taking a cock in my boypussy and couldn't wait to...

Toni in the Park... Again

by Tonisshy on Sep 16, 2017
Anal

He held my head against the wall and struggling was futile. He had already overpowered me with relative ease and let me know if I screamed or tried to fight he would have to punish me. I listened as he was opening something that was wrapped in plastic. Then he spread my legs with a knee, lifted my pleated skirt and pulled my white lace panties to the side....

Alex, The Closet Sissy

by Areallysissyboy on Feb 11, 2019
Transgender & Crossdressers

My name is Alex, a closet crossdresser. 18 years old, never had a date. Too skinny, too weird, too feminine. I wore my hair long but not a hair on my body tho, not very athletic. Just a 5'3" skinny 125lb pale white boy with long black hair. Who loves dressing like a girl every since my older sister, Sam, moved out 1 years ago which left her old room unsuperv...

Jamie Gets Nailed in a Club

by Tonisshy on Nov 25, 2017
Transsexuals & Crossdressers

Sorry it's been awhile. I hope you like this as much as I did writing it!! ***** I've been at this club for over an hour, several men have hit on me but none that I wanted to hook up with. I finally took a seat at the bar, crossing my long tan legs and straightening my light blue chiffon mini skirt. Then a bald guy walks over and sits down. He orders a d...

The Journey Pt. 02

by MissYellowPanties on Sep 26, 2017
Transsexuals & Crossdressers

The Third Room. The Third room was a dormitory. On either side of the door was a line of four beds, the last two on each side were made up. These were soft feminine beds and bedding, not hard army bunks like school dorms have on TV. Between each bed was a chest of drawers, four drawers deep, each labeled from the top down; Bras and Panties, Nightwear, Toys...

Toni Gets Two Guys in the Park

by Tonisshy on Sep 13, 2017
Transsexuals & Crossdressers

He held my head against the wall and struggling was futile. He had already overpowered me with relative ease and let me know if I screamed or tried to fight he would have to punish me. I listened as he was opening something that was wrapped in plastic. Then he spread my legs with a knee, lifted my pleated skirt and pulled my white lace panties to the side....

James Explores Ch. 02: Daddy's Girl

by ShyBiSub on Sep 24, 2019
Transgender & Crossdressers

All Characters are over 18. The first part got wayy more views than I ever imagined so I decided to continue ;) Thank you *.*.*.*.*.*.*.*.*.*.*.*.*.*.*.*.*.*.*.*. Memories from Part 1 "Good girl. See you again next week, same time" He squeezed James' bottom in his hand. "Yes Daddy" The Crush James couldn't stop thinking of what happened that d...

Twice as Nice

by puzziboi on Mar 17, 2020
Transgender & Crossdressers

About ten Christmases ago, Lemar McCants had been shopping for gifts with his early tween daughter. On the list was his wife, his parents, and one of the middle school aged girl's classmates. He remembered the conversation. "Dad," Maryam beamed as she selected what appeared to be a tiny white rag doll with pink hair and a pink cat in the same box. "This is...

Adrian gets Morning Pounding

by Tonisshy on Dec 2, 2019
Transgender & Crossdressers

I am a crossdresser and I'm in my late twenties now but still get carded for cigarettes. My build is not masculine at all, I'm not quite 5'5 inches tall and I weigh 130. I have below the shoulder chestnut brown hair with some lighter highlights which frames my young baby face soft features. My body type is best described as slim with an amazing ass and lon...

Caught In Lingerie Ch. 02

by hicutlover on Mar 5, 2018
Transsexuals & Crossdressers

As I awoke, I found myself on my side, with Tim's arm wrapped around me. He too was sleeping. I looked at the clock and figured I was out for 30 minutes or so. My bed sheet was covering the two of us and all I had on was my bra and thigh highs. Tim was still naked. My sissy clitty was hard; my horniness woke me up and I wanted more cock in my boypussy, right...