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Hello. I'm a 30 year old guy in a big city. Coming out of a long-time relationship. Have only ever been with women. Have literally never had anything even close to a sexual experience with another guy. However, I've found myself watching an increasing amount of gay porn and I'm kicking around the idea of acting on the curiosity. If I do make that leap, how would you recommend I go about it in a safe (on a few levels) and enjoyable way?

I'm a good looking, successful guy (to the extent that is relevant). This is all untested but I'd like to meet a twinky guy.

Thanks in advance
 
I have no first hand advice. I'm straight, not in a committed relationship, and have only been curious with my BFF for a couple of kisses then bolting. We're talking about it. I've got a couple of gay friends who've offered to "help" without pressuring me. I think I'm saving my cherry for my Bro. I did Grindr for some straight hookups don't think I could do a random dude. That's on me.
JUB is the perfect place to figure yourself out. JUB is EPIC.
 
Hello. I'm a 30 year old guy in a big city. Coming out of a long-time relationship. Have only ever been with women. Have literally never had anything even close to a sexual experience with another guy. However, I've found myself watching an increasing amount of gay porn and I'm kicking around the idea of acting on the curiosity. If I do make that leap, how would you recommend I go about it in a safe (on a few levels) and enjoyable way?

I'm a good looking, successful guy (to the extent that is relevant). This is all untested but I'd like to meet a twinky guy.

Thanks in advance

Among other things, it kinda sorta depends on where you live, I used to live in SO CA (OC) and there was no shortage of opportunities when it came to meeting other guys. Now I live in a very small rural town, so the pickings are very slim. In the "OC" I used to go to private house parties and hotel parties at least once a month. Almost a sure-fire way to meet and hook up, in a safe atmosphere. BUT something tells me you're not ready yet for any "Same Sex, Sex".
 
Well, you've already got a huge advantage: you live in a big city! Any big city will have a gay area, and have more gay guys in general no matter where you roam. Go to gay bars, even if you don't drink. And don't be turned off because you didn't like (or score) at the first bar you went to, there are all types of gay bars, just as there are all types of gay guys. Join a gay gym. Go online. There are all kinds of social groups too. The more you put yourself out there, the better your chances of finding a guy (or guys!). If you only want sex, try sex clubs, bath houses, glory holes.
You sound like the type of guy who is willing to wait until you find the right guy to experiment with. There's nothing wrong with being choosy or cautious of strangers.....especially in a big city! I prefer to become friends with a guy before I whip it out, which worked out well, I'm in a relationship with a guy I know well.
My best advice is to do what makes you feel comfortable, at your own pace. Who knows, you might decide after having sex with a guy that the fantasy was better than the reality....although that seldom happens. Usually guys that are curious love it. Sex is like pizza: even when it's bad, it's still pretty good.
If you think you want to try bottoming, do yourself a huge favor and train yourself before you let a guy bone you. Buy a dildo preferably a vibrating one, and go fuck yourself over and over until you get the hang of it. You don't want your first time getting fucked ending up with you screaming for your top to stop because of the pain.
 
I wish you the best luck, I have tried online to find someone and most are hard and wanting to do it right now.. Ive never been that way even with females i have always wanted to get to know the person before anything sexual happened. So i have had zero luck on line,but maybe some of the clubs and stuff others suggested would be better. Far as i know there are no gay clubs in my town but not sure i would be able to do it or not. I mean I have been in a gay strip club before but it was with my 2 gay friends for there party before got married. it was interesting and I wish now i would had hooked up with them. ( they always liked adding a 3rd in the bedroom) I watch guy on guy porn all the time, and i love guy on guy with a female when there all sharing. I would do what Moaningmike said get a dildo I suggest to get a suction cup dildo and fuck it, I love riding mine and my gal sometimes gets me with a strap on. My fantasy is to have a guy join in with us and for him to do me while i go down on her.
 
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