Gay Caught Cross Dressing Stories

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Co-worker's Man Ch. 27

by rmdexter on Sep 14, 2017
Gay Male

My alarm stirred me out of my sleep and I awoke with the feeling of Lori's silky panties lying across my cheek. Mmmmmmm, I moaned into them as I listened to the news and thought about Mr. Wolfe's offer of a "banana cream" breakfast. It sure sounded appetizing, especially the offer of two helpings! I had to get my stuff together to go with Frank right after w...

The Trip Ch. 01

by CE300 on Aug 30, 2017
Gay Male

Dear Reader, This story is kind of long and has lots of detail. It's also emotional and not much XXX in this section. I look forward to your votes and please feel free to leave me comments. All feedback is welcomed whether it is good or bad. I would also like to greatly thank sfseeker71 for looking over my work and helping me with it! Thanks, CE300 ****...

Assuming the Position Ch. 01

by bi golly on Sep 25, 2017
Gay Male

I had been playing with my ass before I even learned to jack off. Playing with my anus felt good and I liked it. When I learned to jack off, I did that for a while, but soon added anus play and fantasized about being fucked. First it was that I was going to get tricked into getting fucked, but then I was honest with myself. If a guy I could trust ever wanted...

The Summer of 2004 Ch. 02

by NYCSTUD on Sep 1, 2017
Gay Male

It was a gorgeous, late June day, 70 degrees and going to climb to 82 by mid-afternoon. "Easy day," I thought. I arrived early and as I walked up to Robert’s door, I heard some loud Led Zeppelin music down by the boat house, so I followed it. Robert was on the grass doing exercises. He looked so sexy. “Hey Robert, what’s going on, man?” I offered as my morni...

Carl Be Mine, My Special Valentine

by SuperHeroRalph on Aug 17, 2017
Gay Male

This is a Valentine's Day contest story. Please vote. * A man asks his best friend to be his Valentine I poured myself a glass of wine and sat nervously on the couch to survey all that I had done. Nearly up all night, I had all the Valentine's Day gifts on the coffee table staged, as if they were ready to wrap. Suddenly, knowing he'd be home any minute, I...

Homeward Bound Ch. 02

by sr71plt on Aug 31, 2017
Gay Male

When the scheme first got started, it seemed to be no big deal, really. By then there wasn't anything to protect and after the first time as part of the boarding house service there wasn't that much to be embarrassed about either. My family came to Asheville when I was just ten. For me, it was an improvement over the dreary coal mining towns of western Penn...

James and Carl in Vegas Pt. 03

by sj_53 on Sep 14, 2017
Gay Male

Hi, I'm James. I want to tell you about what happened on the Wednesday of my week in Vegas with Carl. At the end of part 2 of the story, I had just discovered that Carl was vacationing in Vegas for the rest of the week and that my boss had figured out what Carl and I had been up to. Surprisingly, my boss wanted me to make sure Carl had a good time and would...

Joy of Jonathan Pt. 04

by Showoff888 on Aug 18, 2017
Gay Male

My names is David a white thirty three year old who is enjoy being an exhibitionist, enjoys masturbating, edging, the scent and feel of cum, and I have to confess, the scent and feel of piss. It's all his fault. Jonathan, just saying his name conjures up his image, tall solid built dancer slash swimmer's slash gymnasts gorgeous dark echolocate black body....

A Timeless Place Ch. 07

by windstormy on Sep 14, 2017
Gay Male

The limo pulled up the long cement driveway to the mansion that sat back of the property. The front was a desert oasis with its many live cacti, shrubs, and what flowering plants would bloom in Arizona, ponds and running streams over which the driveway led on wooden arches. Some ponds were graced with different sized waterfalls; each one differed from the ot...

The State of Being Gay

by chuckster67 on Aug 18, 2017
Gay Male

CHAPTER ONE Giggles surrounded me as I slung an arm around a cute brunette, whispering sweet nothings into her ear. It was almost like a dream, being surrounded by such beautiful women, tending to my every need. As I leaned down to tuck a hibiscus behind her ear, some annoying insect buzzed around my face. I tried to swat it away, but to no avail. "This fuc...