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I've been curious about going all the way with an older guy...
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So, I had a wild side about 15 years ago. I was single and just out of a terrible break up. I decided it was time for me to experiment and have fun. During that period, I slept with lots of girls, went to massage parlors and even did the casual encounters from Craigslist when they used to have personals. From there, I fucked Crossdressers, hooked up with transgenders together blowjobs and even met up with a few dudes who also serviced my cock. There was one guy that started it all for me and that was the first guy to ever blow me. It was fucking hot because of the risk of getting caught by my room mates. This guy was so good at sucking my dick, I would sneak him into my garage some times because it was worth it. He knew how to slobber and suck up my cock and cum. It's been years since he's last serviced me but I've been curious lately since a conversation I had with him recently. Out of the blue, last year, I discovered that he had a private account on an app I use on the downlow. I reached out to him and we chatted about the old days and how I missed them some times. I caved and asked if he wanted to meet in the future. He declined and told me why. I guess I am very selfish when it comes to getting pleases. I have never sucked a cock nor taken one from behind. I have always been the giver, not the receiver. If we were to ever meet again, I would have to take his cock both ways. When he told me this, I was hesitant but also very curious. He got me all excited but I was also scared. I've never sucked a cock before. It's been in my head for some time now. He would like to get a hotel so we can meet discreetly on one of my work days. I would come in, rinse down and he would do the same after. While he rinses down, I would get myself ready by laying out on the bed and turning out all the lights. When he gets out of the shower, that's when it would be game time. I would have him lay on the bed and play with his cock in my hands until I'm ready to take it in my mouth. I think I'll surprise him and let him cum in my mouth. After I suck him, he'll take care of my cock and then I'll give him my hole to eat out and play with. If I do this, I'm hoping we can play for hours until it's time for me to go. For now, I think I want this to be a one time thing... But we will see.

Let me know your thoughts. Should I go through with the meet up?

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2 months ago