I guess at my age, (50) all of my recent sexual encounters are surprising. But, I will share two encounters from my youth.
When I was about 18 and going to college, I was really into photography, and was just starting to make a few bucks with it. I took all of my film to a local professional lab and since I was a regular customer, everyone knew me well. There was a 45 year old school teacher that worked there after school to supplement her income. She was off the charts hot! She literally could have been a mature model. Pristine from head to toe.
I was a pretty good looking young man in those days, but still lacked confidence and had very little "game." I flirted with her as best I could with my limited skills, and in retrospect, she couldn't have been more receptive to my advances. Poor gal, she must have thought, "Do I have to hit this fucking kid in the head with a brick to get through to him?"
One day I finally got my well deserved brick. She handed me a folded up piece of paper with little hearts and kisses all over it. It was almost as juvenile as something you would get from your Jr. High sweetheart. She told me how attracted she was to me and how much she looked forward to seeing me. The only difference between this letter and something you would expect to get in Jr. High is that she wanted to know if I would be willing to come by her home and take naughty pictures of her? Would I be willing? Fucking right I would! Long story short, took numerous naughty pictures of her, and nailed her every chance I got for the next six months or so.
Sad thing is, a few years later my new wife made me get rid of all my nude pictures from my youth. I swear I would give a thousand bucks today to have the pictures I took of her back! On another note, I ran into her about twenty years later while grocery shopping. Yep, she was sixtyfive-ish and certainly looked like someone's grandmother, but still had a little sexual appeal. Hate to admit to this, but while we shared a little conversation, she kept touching my arm and still made my dick hard!
On another occasion, maybe a couple of years later, I walked into an almost empty popular bar. This bar was almost packed to capacity every night, but on this particular night, it had been raining hard for hours and flooding was taking place all over town. Again, the bar was almost empty, probably only a dozen people there. I grabbed a beer and looked around to see if there were any single girls there. As I recall, there was only one single girl available, so I got my drink and headed her direction. The closer I got, the better she looked. She was in her mid thirties, very attractive, wearing a tiny little mini skirt, and had legs for days. I still didn't have a hell of a lot of game at that age, but I had gained enough confidence by then to at least take a shot at her. Nothing ventured, nothing gained. Naturally, I can't remember the exact conversation, but I do remember it going almost this quickly.
Me: "So what brought you out on such a shitty night?"
Her: "I was here to meet my coworkers, but apparently nobody else is going to show." "Would you like to follow me to my place as soon as I finish this drink?"
I swear it was that brief! I so wish all encounters were that quick and easy!
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