Gay Cross Dressing Stories

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Sissies love big black cock

by Yelawolf on Nov 16, 2017
Gay

Welcome to the story you crazy sissies and you strong aphla black males. This is from edithis and I want to bring here so you guys can write or read or for the real reason you're here to masturbate. Get your hand, dildos, lube, and whatever else you need to jerk it off. Time to begin the story up. (Thanks for all of the likes and support on this story. I jus...

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A Birthday Femboy's Night Out (Now Public)

by meris on Nov 4, 2016
Gay

My name is Samantha. I wake up in the morning feeling very excited, today is my Birthday and I have very special plans for celebration. I step out of bed and take a look in the mirror, my dark brown hair gone frizzy from yesterday’s antics. I can still feel that guy’s hand gripping a big handful of my hair as he railed me. I giggle musically to myself at the...

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First Experience With A Man Ch. 1

by girlboybootsie on Aug 18, 2017
Gay Male

I wasn't always attracted to men. In fact, until I was 18, I never felt confused about my sexual orientation. In terms of sex, I was only attracted to girls, especially sexy ones who dressed in provocative and sexy clothes. I was popular with girls, and had lost my virginity when I was 14. Without meaning to be immodest, I was, and am, a very good looking gu...

Sharing Secrets Pt. 05

by Showoff888 on Sep 14, 2017
Gay Male

I'm a shy, smallish, slightly pudgy from my waist down, a bit wider in the hips, butt and rounder legs, small delicate hands and feet. I think I'm a very passable nubile little Japanese girl, with shoulder length black hair, small nose, full lips, long lashes, and a tiny penis, and obviously flat chested. This summer, my Mom divorced my kinky Dad, for someon...

The Fraternity Party

by Dawns on Aug 18, 2017
Gay Male

The Lambda Delta Phi frat house at UCLA campus decided to have a party at the start of the school year. It would provide a chance for new students and members to get together and get to know each other. There might be thirty plus members there. I was just starting school as a freshman back then in September 1997. At the same time I was coming out. I knew si...

Turning Myself Gay Pt. 04

by bart_allen on Jun 25, 2018
Gay Male

Things changed slowly over the next half a year or so. Work was work, boring and uninteresting, but between that, my consistent aerobic gym work outs and keeping up with Danny took up the majority of my time. We saw each other every week or two, but sometimes he'd go days without texting me. He was definitely a bit of a bro, but he was always friendly and he...

Lust Never Sleeps Ch. 06

by ShelleyRunyon on Aug 31, 2017
Gay Male

Darryl opened his eyes to find himself looking directly into Sawyer's cinnamon gaze. "Morning, love." The chipper beauty smiled—Darryl melted. "Sleep well?" "Slept wonderfully," Darryl replied. "Me too." Sawyer placed his hand against the back of Darryl's dark head and pulled him closer, their lips meshing perfectly. I think I could easily get used to...

Cadogan Street Carpark

by PicturePainter on Sep 16, 2017
Gay Male

My name is Peter and I am 49 and married but a secret sissy cocksucker. I have a very dirty secret. The feel of women's lingerie against my skin makes my 6 cut cock harder than steel. And it's more than just the cross-dressing. I am bi sexual and I would love to submit to dominant older or younger men. I remember as a child my older sister Janette had the...

Winners and Losers Ch. 12

by bawdybloke on Sep 15, 2017
Gay Male

If you have missed the previous installments the premise of the story is that after a football match, the losing team must provide sexual relief for the victorious players; the narrator has recently admitted his bisexuality to himself, his team and his fiancée. Previous chapters for Winners and Losers are on Literotica * * * * * My "coming out" to my team...

The Dark Place Pt. 01-05

by DarrenAddams on Apr 14, 2020
Gay Male

1 I never expected to end up in this position. Cold, alone, desperate, I huddle beneath the overpass and try not to think of the things my parents had said no more than three hours beforehand. You're gay? they'd asked, then repeated it by saying, You're GAY? I'd wanted it all out in the open, so I could finally stop hiding from not only myself, but the...