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Older men

B

Benkf90

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Have a question. This does not include men who were forced/raped as boys by an older man. But if your first time or one of your first experiences was with a man many years older, what were your ages and was he a family friend , neighbor or hookup?
 
I was 20, he was... older late 30s early 40s. It was a hookup from like squirt or one of them things (it was only a few years ago and I can't remeber :P).

I like older guys (not exclusively) so that's why if you were wondering
 
I was 16 my first time and he was in his mid to late 40's - actually happened in a Sears dept store bathroom.
 
17 in a local large wooded park. I was honestly just there hiking etc. In a real wooded area a guy in his mid 50's asked me if I wanted a blow job he was nervous I got horny. I said what if someone sees us I do not want to get in trouble he pointed to a small cave opening in the rocks about 6 foot high 8 foot inside. He gave me my first rim job and sucked me off twice. Never saw him again unfortunately. I would find it hard to turn down a guy that just wanted to enjoy servicing e because he was older.
 
It wasn't one of my first times but when I was 23, I was not long out of a relationship of a few years. I remember it was pretty late at night and I was really horny and online on one of the sites, squirt or something, talking to a guy who was 43 or so. At the time, the thought of doing anything with anyone older than me just didn't turn me on at all. I think at that point, I'd only ever done anything with guys younger than me by a year or two. But I was also really horny and just wanted a blowjob so he invited me over and after some convincing, I finally agreed. I was really nervous because I didn't really do hookups often, I wasn't into the idea of doing anything with an older man, and I was about to go to a complete stranger's place.

So I got to his apartment, he invited me in. He was a bit shorter than me, thin, good looking. He was really nice, told me if I wasn't comfortable, I could leave whenever I wanted. But I made it that far so I figured why not. I especially remember he had a really deep voice. So I unzipped my pants, lid on his bed and let him take out my cock and suck me off. It felt so good! Probably the best bj I ever had at that point. I thanked him and left. I think we chatted once or twice more after that but I never saw him again.

After that, I started entertaining the idea of older men and since then I've explored it a lot more. Now, when I think about older men in a sexual context, 43 is too young.
 
That's where I want to take a young guy, since I'm the older man this time
 
first time when I was 19 hooked up with a 50 years old bear from manhunt. or one of the dating sites. Been dating my ex for last 5 years just before I turned 20. He was 62 when we broke up last year. He's still freaking smokin hot. Now seeing a new friend~ hot! hot! hot! he just turned 50. Although I'd love to get married and have a real relationship, just bad timing. got to leave again. and this time might be forever :( seize the day, boys~ seize the day~
 
I gave a BJ to a guy maybe 20 years older than me, not just once, but twice! It was great both times for both of us!…
 
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