Gay Cross Dresser Stories

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Orientation
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Infinite Scroll

Talking Him Through

by madamefielding on Aug 30, 2017
Gay Male

**Note- this was originally part of a novel I was writing, and there is a REASON why eighteen year old Antoine has never masturbated before: When he was very young, he witnessed the beating of a boy for being caught masturbating by the dormitory's deacon (Catholic school). The boy then had to tell his classmates what he did and was flogged again, naked befor...

Beach, Bed and Beyond Ch. 02

by paul81219 on Oct 6, 2020
Gay Male

I heard my name being called from the end of a long, dark corridor...or was I at the bottom of a deep well? "Paul. Paul." The voice got louder and the light brightened as I emerged from the deepest, soundest sleep I had ever experienced. "Wake up baby, I have to go and so do you. You've got half an hour." The voice was Daniel's, my 35-year-old lover who...

Cumslut Diaries -Intro

by bigal999 on Aug 18, 2017
Gay Male

I answered an ad in Craigslist: Male cumslut needed for evening. Email pic, no pic, no response. If I like the picture, you'll get another email. I answer a lot of ads, most never pan out, I'm kind of picky. I prefer married business types with nice dicks. My response to this ad was: I'm a married, white, 45 year old male, 170, 5'9", love to suck. I'm kind...

Aaron's Summer of '77 Ch. 18

by SDR2000 on Jan 23, 2019
Gay Male

Chapter 18 - A Year in the Life Of "Hi Dad." "Aaron son. How are you making out with school and did Adam make it back OK from Edmonton yet?" "School is finishing up this year OK. I just have to finish some working drawings for my store project and do a formal presentation of it. Then a couple of other small projects on colour theory and I think that shoul...

Back Stage

by RedTrickster on Aug 18, 2017
Gay Male

Jared sat in a corner of the greenroom off by himself going over the script once more. It helped him to get into character and smooth over any rough spots. He picked absently at the blue silk shirt that was part of his costume and turned the page. He was reading a part that had been giving him trouble recently and the director was getting tired of pointing i...

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...

Mikey and the Chickadee Ch. 08

by kidboise on Feb 5, 2018
Gay Male

I spent the first half of Friday judiciously hungover. Marie, Sloan and I ate sushi for lunch (our first meal of the day) at a place near to her condo in Celadon. The sky had remained solidly overcast throughout the night, trapping in a cradling warmth that now accompanied sunlight as the clouds began to part. We sat out on the restaurant's terrace along w...

Horns of a Dilemma Ch. 02

by dsl01302017 on Oct 8, 2019
Gay Male

Please read chapter 1 (it is titled "Horns of a Dilemma," but without a chapter number) before proceeding. This story contains non-consensual gay (M/M) sex and other things that may offend. ***** "Get ready for what's next, bitch." I was still on my knees with the awful taste of his cum in my mouth. I had planned to give my first blowjob tonight, but not...

Jake and Toby Ch. 08

by kmillerk1 on Sep 19, 2017
Gay Male

Hello Everyone, I want to thank my editor and proof reader. Hope everyone is having a wonderful New Year. It is not a typo Jake and Toby is only up to 2015. :o) As always, public and private comments are welcome. Thank you. Happy Valentine's Day in advance. ******* ***Jake*** Toby didn't have to work New Year's Day but I did. I asked him to wake me up ju...

Mattress Delivery

by skyscraper11 on Aug 18, 2017
Gay Male

This is a true story * I had been waiting for this day to come now for so long and it was finally here. Today was the day that I was getting rid of the old prison mattress that I had been sleeping on for so long. That is what at least my gf had been calling it because it felt like you were lying on an old prison bed. Both of my parents were at work on thi...