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Another first time  

Corotl2004 42M
2 posts
6/24/2019 3:24 pm
Another first time


So, in my last post I shared about my first time with another guy doing the oral stuff and my first taste into guy on guy oral sex. It was fun and interesting and while I mostly identify as a heterosexual guy in public as I couldn’t see myself in a relationship with anyone but a girl, when it comes to sex, I do enjoy an occasional cock but mostly again into girls.

A few years ago I decided after my first experience 20ish years ago that I would seek out a guy for some fun. I had played with the thought of bottoming for a guy but that’s all it had ever been. So, back with Craigslist was allowing personal casual encounter posts, I put a post out there and got a ton of responses. There was one older gentleman that seemed nice and intelligent enough to have a conversation and I thought, what the heck.

After about a week of conversation I got the nerve to meet him. He could host but it was about a 40 minute drive which I was okay with. After pulling up I was about as nervous as you can imagine as I really couldn’t believe I was going through with all of this. So he invited me in and we made small talk for maybe a few minutes and then we moved to his bedroom where we removed our pants and underwear and started to touch each other’s cocks. Just like 20 years before, I was like wow, feeling another guy’s cock is totally different. Then he started to go down on me and while I’m not a stranger to recieving oral, this was very good. I let him work my cock for a few minutes and then he asked if I wanted to<b> switch </font></b>in which I said of course. His cock was just about 1/2 inch longer at 6 1/2 inches and maybe just a little more girth but about the same. So after a couple minutes we started to 69 each other which lasted a couple more minutes until he announced he was going to cum. I just kept sucking his cock and he came. I don’t know if it’s because he is in his mid 60s, but he didn’t cum much but at any rate, he did cum. He sorta lost interest after he came so I had to take care of myself which sorta sucked it was what it was. After that, I left.

So, a week or so later I ended back at his house. He asked me if I ever though about getting fucked and I said that I would probably be willing to try it but for him to be gentle. After a few minutes of oral between both of us, he asked if I was ready. After putting on a condom and some lube, I got on my hands and knees and he tried to push in to no avail. Finally after a minute of that he asked me to lay on my back on the edge of the bed and he was going to try it that way. After a minute or so it happened, he put his cock head on my hole and it just popped in and holy shit, it definitely hurt. I realize now why guys breathe the way they do on porn, it’s because it takes a few minutes to get used to it. I asked him to stop and just hold still while he was most of the way in me and when his cock throbbed it about took my breathe away. Honestly, after a few minutes he slowly fucked my ass and while I don’t think it ever felt super great, I knew he was enjoying himself. He didn’t last a minute and was cumming which was sorta a downer.

To this day I occasionally do stuff with him and while bottoming has gotten better and actually feels pretty good now, I’d really rather find a guy my age to enjoy this with. Nothing against older people because I know my time is coming but after several times where he doesn’t ever really focus on me getting off I believe I’m about done with it.

I hope you liked my second first time, well, okay, first time with anal. As always, thank you for taking the time to read and while I’m not an elegant writer I hope you enjoyed.

HAMONMAN 64M
13128 posts
6/24/2019 4:45 pm


Everyone has a first time right


wrMercury 46M
1570 posts
6/24/2019 6:49 pm

Too bad you aren't closer


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