First Time Bi-Experience

Tame as it may be here is my first time bi experience.

I was bi curious for a long time, years ago watched closely as my ex-wife sucked me and wondered how it must feel to have a cock in my mouth. We divorced when I was 39 and at that time gay porn was becoming more assessable online. I watched a lot of gay massage videos and loved when the guy giving the massage had an erection or noticeable bulge, knew that would be me. Also remember at that time testing my gag reflex using bananas. Discovered later sucking on her dildo while masturbating and staring into the mirror was incredibly hot. Watching that cock shaped dildo slide in and out of my mouth always got me hard and wondering what a real cock might felt like.

For the next ten years I suppressed my urges to physically be with a man and continued dating woman. I had sex with a few but most of the relationships ended after the first dinner date. Most of the woman in my age range were looking for long term romantic relationships. Seemed others were just on the dating site for a free movie and dinner. Courting the opposite sex became a chore and getting to sex was near impossible. To be totally honest I was searching for more of a fuck buddy.

My sex drive was still high as I approached 50 and was using gay chat rooms to discuss my bi sexual fantasies and jerk off . Also discovered I was not alone as there were lots of bi curious, mostly married, men in my age range looking for discreet sex. Most just wanting a clean hard cock to play with. When I discovered c2c private chats I was jerking off like a teenager again. Found watching and talking with real guys as we stroked together was incredibly exciting while still being safe. However the lack of physical sex over the past ten years was frustrating and I was growing tired of jerking off alone.

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.