Reading the man-seeking-man dating profiles always got me hard thinking of the possibilities and eventually created my own. A recently divorced, bi curious, very nervous guy contacted me. Our stories leading to this point were very similar, even our age and first name. For weeks we jerked off together on cam and traded emails sharing our secret fantasies. Mine of course was to give a naked body massage with happy ending and he wanted to dress up. I'm not really into guys dressed like woman but after trading emails for so long felt he was safe and did not want regrets later in life. Being nervous first timers we planned to meet but only for mutual hand jobs, no kissing, no oral and definitely no anal. With heart pounding I drove past his place 3 times before finding the nerve to finally stop.
The initial meeting was awkward we talked about nothing and everything for about 20 minutes while eyeballing each other. He was a normal looking average guy but I knew this from all the time we spent on cam together. I was anxious wondering if my cock would rise to the occasion because I didn't feel anything stirring below. Suddenly he stood up and said I'll go get dressed, came out of the bedroom wearing heels, stockings, blouse and a skirt. We started to grind together with our hands running all over and by the time I found panties under the skirt my cock was rock hard. He told me later how much he enjoyed when I pushed him up against the wall to dry hump him harder. We didn't speak for what seemed like a long time until finally he said lets go to the bedroom.
He lay on his stomach and I straddled his back. I undressed both of us gradually during the massage till we were nearly naked. I had watched enough videos to somewhat know how to give a decent massage. Took my time rubbing his back, legs, arms, feet and panty covered ass. I enjoyed the naked body contact and could tell he also liked feeling my oily hard cock sliding between his ass cheeks cause he was pushing back on it moaning and squirming. It was a little disappointing when he rolled onto his back because I barely touched his cock and he started cumming. I suppressed the urge to put my mouth over the head to finally feel a cock spurt warm thick cum in my mouth.
I finished myself off soon after. When jerking off alone cum oozes out of my cock but my first bi-sexual experience ended with cum spurting out across his bed. It was so hot! Got dressed and out of there quickly, driving home my mind was spinning with what just happened but knew I wanted to continue exploring my bi urges. Our second meet was more relaxed and much hotter but that's another story.
