Gay Cross Dressing Stories

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Infinite Scroll

I Thought I Wanted It Rough... Ch. 02

by LonelyVirgin on Sep 14, 2017
Gay Male

I had just been fucked for the first time. I couldn't believe what I had just done. Some stranger had just used my ass for their own pleasure. Someone had stuck their dick INSIDE me. What was I doing? What kind of slut would do something like this? I didn't even know this guy, and I agreed to meet him, and let him pound my virgin hole. Before I had made up...

Our Preference for Black Pt. 02

by eviltwin52 on Sep 19, 2017
Gay Male

This is dedicated to the all anonymous commenters. Bring on the hating... and then go fuck yourselves. LOL. ***** Our role reversals had come about quickly. Surprisingly, it didn't bother me that in our small town it became public knowledge that Cheryl had a black lover and that I was more than accepting of it. That so many people who once respected me, no...

The Joy of Submitting

by loneguy01 on Aug 21, 2019
Gay Male

I had recently answered an ad seeking a submissive cocksucker. I am a total bottom and had experimented with cross-dressing but never really got into the dom-sub thing. However, the ad intrigued me and I submitted myself to a hung black man in his hotel room. The experience was exhilarating and I yearned for more despite being apprehensive about the possible...

Cheating on Our Wives

by StephanieSeymour93 on Jul 15, 2020
Gay Male

The moment my cock slipped inside his asshole I knew it was the real deal. We were going bareback. Neither of us gave a fuck, and we were both married anyway, so the risk was low. He was on his stomach on the bed where he fucked his wife a night earlier. Now it was my turn, and I wasn't holding anything back. I was on top, pumping him. He wore his wife's lac...

I am not a slut, yet!

by stevensinner on Apr 21, 2020
Gay Male

I typically buy my marijuana from Dennis, my friends much older, gay uncle but this day he wasn't home or answering his phone. I knew that his neighbor, Greg, sold weed for him sometimes so despite not knowing him well I went to his door and knocked. "How can I help you?" Greg asked while sizing me up. I am a very petite, 18-year-old male at only 115 poun...

The Warden

by TheGoodSick on Sep 14, 2017
Gay Male

Bryan walked away for a moment and left me standing in the shower. I dried off like he told me to and sat down on a three-legged stool. Only a few minutes had gone by when he came back through the door. My massaging had me relaxed and content, but the sudden loud jerking of the door startled me. Bryan carried a box over and put it down on the desk with a thu...

Turning Myself Gay Pt. 03

by bart_allen on May 29, 2018
Gay Male

To my mutual humiliation and arousal, the next morning at work, Marie could instantly tell. Truth was, I could see why: Nathan had fucked me three god damn times, and I my ass was sore as hell. Sure, he'd been tender as well at times, but one look at me and she knew. She just rolled her eyes at me, causing me to blush. She wanted to know what he looked like,...

First Bisexual Experience

by rogue2 on Aug 18, 2017
Gay Male

This is the true story of my first bisexual experience. See I am a 30 years old bisexual male and have been that way for about 10 years. I am 5'10" 175 lbs. nice ass and tight bas athletic muscular build and go to the gym 6 times a week. It started when I was in college when I first got a computer and was exposed to the internet. I began looking at female p...

I Make Believe I'm a Cuckold Ch. 04

by donaldelliott11 on Feb 10, 2020
Gay Male

This is the fourth and final chapter. You should read the others first. This chapter contains a scene of incest between two adults. [Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either. Comments help me improve my writing; ratings help other readers find what they most will enjoy reading. Ra...

Cross-Country with My Uncle Ch. 09

by John Hill on Sep 14, 2017
Gay Male

Mikey, a studly 18-year old finds himself intimate for the first time with Mike, his namesake 24-year old uncle whom he's idolized all his life during a cross-country drive. Steve is the 20-year old collegiate gymnast who hitches a ride with them. As he lay between my legs, Steve and I were still grasping each other's arms. His arms were extended over his h...