Gay Cross Dresser Stories

3,450 results
Orientation
Length
Source
Infinite Scroll

Bathhouse Observations

by glory_first on May 12, 2020
Gay Male

The baths are undoubtedly the easiest place in a city to have male group sex, after allowing for individual circumstances during any single trip. After more than a hundred visits over the last few years, basically all of them involving satisfying sex with other men, often writing about the experiences afterwards, leads to a few general observations. Visitin...

Finding a Niche

by KeithD on Jun 9, 2020
Gay Male

I found quite early in my experience—and, eventually, career—that being able to bareback in sex with a man was a means to please him to the extent that he would commit to me—financially and with favor, if not romantically. I found that it took me to higher levels of satisfaction too. So, after initially letting myself be taken that way out of naivete, I rese...

Explorers

by T@nman on Apr 3, 2019
Gay Male

High school was a good time for me. I did o.k. on grades and I had a girl friend and some buddies. My girlfriend’s name was Lana. She wanted to be a journalist. She wrote for the school newspaper and she was on the school annual staff. She and I became friends when we both joined the Camera Club late in our Freshman year. She wanted to learn about photograph...

Found Ch. 06

by cowboi on Sep 26, 2017
Gay Male

Walking up the stairs, Melania heard her brother Lucas walking around his room. She wondered about his and Calen's outing to the property earlier. The expression she saw on Luke's face when Calen walked in during the meeting was priceless. She knew she HAD to bug him about it. "Hey can I come in?" Melania asked as she softly knocked on Luke's slightly opene...

Sissy Bottom Has a Nite Out

by lostsoul1974 on Sep 14, 2017
Gay Male

My wife had gone out of town on a weekend business trip, so I invited my Fuck-buddy Eric over for some fun. I met Eric a couple years ago when he passed me his business card through a Glory Hole after he had fucked my asshole raw. After I eventually called him, we hit it off and have been friends ever since. Of course, hot raunchy sex can really help cement...

Bathhouse Heaven Ch. 27

by glory_first on Feb 20, 2018
Gay Male

Having just finished a story from the end of the holidays, it is truth that intentions do not follow a schedule. I generally try to jot down what happened during a visit, but finishing the story takes a long time. In part because of the delay, as the glow of an extraordinary visit leads to more stroking instead of writing. Especially after enjoying some mo...

Truck Stop Trio

by Versatile2008 on Sep 19, 2017
Gay Male

I walked into the truck stop diner and was surprised to lay my eyes on an old truckin' buddy, Hank. I hadn't seen him for a couple of years. We both haul loads Coast to Coast, but rarely cross paths. "So, how you doin' good buddy?" he asked. "Not bad. Though I sure am looking forward to a night on a real bed. I haven't been getting much shuteye. I'm a big...

Putting Myself Through College Ch. 09

by RobXXX on Aug 31, 2017
Gay Male

My Spring Break assignments were not finished, just my time pretending to be someone I was not, well at least the sex I was not. I received a call from Kevin the day after the cross dressing assignment, he apologized a little bit for the previous day, then jumped right back into work. That night he had another client for me, this one he said was a known cl...

Nympho Discovery, Love of Cocks

by Alluring_Crimson_Shifter on Aug 31, 2017
Gay Male

Ricky was getting ready for his first sales convention with his new job. He hoped he would make a lot of valuable contacts. Looking in the mirror he straightened his tie, and practiced a charismatic smile. For a 19 year old he was confident and knew he would be successful in his new sales career. He had opted to postpone college and try making a successful c...

Button Down the Hatches

by Kenderson on Nov 27, 2017
Gay Male

Sitting at my desk that rainy, grey Thursday afternoon, I wondered what the point of it all was. I mean, really...how many times did this one short communication need to be tweaked before it was ready for publishing? A short memo about new parking passes had been back and forth for edits over 8 times at this point. Changes here, changes there. One more chang...