I've (30M) had a couple gay sexual experiences in my past (got a little coerced while drunk to hook up with an acquaintance and went to a bath house another time) but since 24 have been cross dressing on occasion to take photos for the internet, have on and off been fucked myself with toys, and jerk off maybe 70% of the time to gay/sissy porn.
I was recently on a business trip in a semi-big city and had a hotel room to myself. After too many drinks, I downloaded Grindr at midnight started chatting with a 36 year old guy who was within a couple blocks. I only had a body pic in my profile to limit exposure. He was discreet, had some profile pictures that showed his clothed body and side of his head that indicated he was a HWP black guy. After chatting briefly and letting him know I was only in town for one night, I decided tonight would be the night I acted on my impulses and I invited him to meet up in front of the hotel with the possibility of going up to my room. After he accepted and said he'd meet me there in 15 minutes I hopped in the shower to freshen up and fingered myself a little bit to make sure I was clean just in case.
Met him outside the hotel and he was super hot with pretty eyes, a nice smile and looked fit in his tee shirt and jeans. We introduced ourselves and exchanges short pleasantries before I invited him up to my room. Since it was very late I didn't expect to see any coworkers in the lobby or elevator but the threat was there which made me feel even more nervous. He asked some more questions about myself that I was unable to cohesively answer due to the nerves and apologized saying this is my first Grindr encounter so I was very nervous.
The nerves faded when we got to my room and, after I asked him if I looked alright enough for a hookup and he said yes, I leaned in and started kissing his soft lips and running my hands along his back underneath his shirt while standing next to the bed. After a couple minutes of this, I asked if he wanted to lay in the bed. Once in the bed (still clothed) I straddled him and began grinding on his crotch, making out and kissing his neck and earlobe. Another few minutes pass like this before I take off my shirt and shorts, prompting him to do the same. Both of us in our boxer briefs, we continued to kiss and while I grinded on him. His hands moved up and down my body gripping my ass and guiding my hips. This time I was able to feel him getting hard since there were only millimeters of fabric in the way...