Anal - hookup

Absolutely I'd fuck with a stranger/hookup/one night stand, and I have on numerous occasions.

My question then is "Why would you not?!?" I mean, if you're having a hookup or one-night stand as opposed to someone you're aiming to woo as potential BF, what else are you expected to do? Unless time and/or location constraints indicate it should just be a quick blow job or jack off. But if you've planned this in the least or just picked up a guy in a bar or something, the idea is kinda in place that there will most probably be fucking.

And of course condoms would be involved.
 
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My question then is "Why would you not?!?" I mean, if you're having a hookup or one-night stand as opposed to someone you're aiming to woo as potential BF, what else are you expected to do? Unless time and/or location constraints indicate it should just be a quick blow job or jack off. But if you've planned this in the least or just picked up a guy in a bar or something, the idea is kinda in place that there will most probably be fucking.

I'm not sure if this was a rhetorical question or if you're actually wondering, but I'm leaning towards the latter. My answer is threefold:

1) I just don't do hookups generally speaking. I don't enjoy the extensive calculation of risk that one has to do with a hookup. The one time I had a proper hookup (had sex on first meeting from a hookup app) I failed to properly calculate and picked up something. And this was after being sexually active for nearly a decade, so it's not like I was totally green and naive. It also doesn't satisfy my preference for intimacy and I find it difficult to process emotionally. To top it off it's pretty awkward; I'm not one who's generally able to have comfortable interactions with new people.
2) I ascribe a very high degree of intimacy and "soul connection" to sexual intercourse. That doesn't mean that I refrain from engaging with it save for marriage, but it does mean that I shy away from it unless I know and trust someone and feel we have that connection.
3) Over 95% of my experiences of intercourse have been without a condom. That's because they've all been with my ex. We used them a few times starting out the relationship and then discarded them once trust was developed. I haven't had to use them hardly at all (there was one time after we broke up) in the past several years. And I remember them being pretty unpleasant, so I'm not eager to jump back into a situation where I have to. Not to say I wouldn't if it came to that, but it is another factor that's leading me to shy away from more casual anal sex opportunities.

So, with respect to #'s 2 and 3, even when I do occasionally fool around with a friend, so far I've avoided having it escalate to engaging in intercourse.
 
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It’s 50/50 for me.

I always get my cock sucked. But I don’t always fuck arse (ass)...

It depends mainly on my mood, I think.

It’s better than 50/50 when it’s a repeat meet with a guy I’ve used* before...

But the whole thing is about enjoyment, the meeting, “being with” the other man. Not so much a list of specific activities...


* I say “used” because I’m into bdsm, and am a dominant leather top, most of my meets. That’s just a language/style thing though - it’s really all consensual, and mutual despite the different perspectives.
 
It’s 50/50 for me.

I always get my cock sucked. But I don’t always fuck arse (ass)...

It depends mainly on my mood, I think.

It’s better than 50/50 when it’s a repeat meet with a guy I’ve used* before...

But the whole thing is about enjoyment, the meeting, “being with” the other man. Not so much a list of specific activities...


* I say “used” because I’m into bdsm, and am a dominant leather top, most of my meets. That’s just a language/style thing though - it’s really all consensual, and mutual despite the different perspectives.

Oye! You have me all excited now! :)
 
Yes, I have had random hookups, mostly from CL or sites like that. I like sex with women, but only Bottom with guys. So my hookups have always been me as the Bottom. I only play safe, so always with a Condom. Some of my random hookups have turned into regular things though.
In recently I discovered a woman with a pegging fetish on CL. She has more sex toys than anyone I have ever seen. And likes to use them on me. That random thing that turned into an Awesome regular thing now.
 
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