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Thoughts/insight on first time sex with a guy

Discussion in 'Physical & Sexual Health' started by Mlh88, Aug 12, 2020.

  1. Mlh88

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    Hey everyone,

    So I’m just going to run down some thoughts I have, any advice or insight is appreciated.

    I’m in my early 30s and still a virgin, I haven’t even ever kissed a guy.

    I’ve tried some of the online dating apps but have had very little luck, a few dates but no sort of connection whatsoever and no follow up dates.

    Since I’ve not really had any luck connecting with someone on a relationship level, I’ve been considering a friends with benefits situation (whenever the pandemic allows), while I’d like to find the one eventually, I’m okay with being single, however, I would really like to have that experience of being with a guy, as clearly it’s something I’ve waited a long time for.

    Been chatting a little bit with a guy that I’m considering a friends with benefits type of thing with, obviously I have a little bit of nerves with the first time as I’m sure everyone does.

    I’d like to bottom, and I’ve tried to do research on it so I can be at least a bit prepared with that whenever it does happen.

    Any tips for first time bottoming? I’ve never even fingered myself or used any sort of toys, is that absolutely necessary to do beforehand? I don’t know if it sounds crazy, but I’m not really sure how to do that, and I feel like I’d just really be a lot more comfortable with him fingering me to loosen me up and going slowly and gently with me for first time penetration if that could still be really pleasant and comfortable for me. From what I’ve read online, it seems like as long as you use lots of lube and go gently and slowly with penetration, it shouldn’t be painful even if it is the first time.

    I guess because of how long I’ve waited for my first time, I think I’ve just put a lot of pressure on myself and built it up so much, but I also don’t know that I’m being very fair to myself to keep denying myself something that I really want and that experience just because I haven’t had any luck finding Prince Charming yet. I feel like I put in so much work in summoning up the courage to come out and be myself, and I haven’t even gotten to enjoy one of the most fun and exciting parts of that.

    Sorry for the long and probably rambling post lol. Thanks for any insight or thoughts anyone has.
     
  2. HM03

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    Lube and patience are definitely SUPER important. And yeah, a good guy will have no problem doing extended foreplay to get you ready - And I encourage it.

    However, I think you should really play around with fingers/toys beforehand. There's an "ahh, get it out" thought process the first several times because you're really not used to the sensation, and practicing beforehand can help your body be okay with something up there. I'd suggest using fingers and working yourself up to a realistically sized toy.
     
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  3. Nickw

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    I agree with @HM03

    Is there a reason why you haven’t tried some self anal play up to this point?

    As far as the first time with a guy. I guess I’m a little old fashioned with this. But, building a level of trust with your first time will be very beneficial. My first time, I had known the guy for awhile and we built slowly to intercourse. That made it one of the best experiences of my life because I trusted the guy.

    This isn’t something you need to consider “getting it over with” to be a gay man. There is no reason to rush this and there is every reason to savor this experience.

    From a practical standpoint, you should be comfortable enough with penetration and wearing protection, or being sure he is, before you go there with a guy. So, maybe when you find this guy you be sure that he is willing to take it slow and safe and that his number one priority is that you are safe and satisfied.

    Best luck!
     
    #3 Nickw, Aug 12, 2020
    Last edited: Aug 12, 2020
  4. PatrickUK

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  5. justinf

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    Is it necessary to experiment on your own? No. But I would still highly recommend that you do. As other people here have said, being on the receiving end of anal sex is an unusual sensation that really takes some getting used to. It helps to sort of know what to expect. And even then, learning to relax isn’t something that happens overnight (or at least it isn’t for most people).

    Lube and going slow are definitely important, but even with lots of lube and with the most patient guy, there’s no guarantee that you’ll get it right the first time. In fact, chances are you won’t. But you can increase the chances of it at least being a pleasurable experience by getting to know your body a little better and having realistic expectations as a result.

    Like Nickw, I’m also curious as to what’s holding you back from trying some anal play yourself? The first step in having good sex is knowing and being comfortable with your own body, so I don’t see the harm in a bit of self exploration?

    As for the sex itself: the only advice I can give you other than what’s already been said is to try and not overthink things. When I was about to have sex with a guy for the first time, I remember reading all kinds of articles, and checklists, and tips about anal sex, and I found it pretty overwhelming and confusing (sex with a guy sounded so difficult). In the end, instinct took over and it was nothing like how I though it would be.

    So in short: get to know your body on your own first, make sure the guy you’re with respects your boundaries, and then just let it happen without having too many expectations. And of course, use a condom if and when it comes to that.
     
  6. Mlh88

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    Hey everyone,

    Thanks for all the replies so far, I’ll try to answer some of the questions the best I can.

    As far as why I haven’t done any sort of self-exploration yet, I’ve thought about it before, but I guess it just comes down to being sort of nervous about it (which may sound sort of crazy lol). I just don’t really know what to do or if there is a good technique, I think that’s why I had a mindset a bit of maybe just jumping right in with a guy who was more experienced and would know how to do it better than I do.

    As far as some of the other questions, I think I did take sort of an old-fashioned approach at first as well about dating and finding someone and leading up to that, but I’ve tried meeting people various ways, via dating apps, friend groups, out to bars and other venues, etc, for the last 5 years or so, and I’ve only managed two dates, both of which were not great, so I don’t think it’s about “getting it over with” so to say, but I do really want very much to be able to have that experience with another guy (and hopefully on a somewhat regular basis too), and I just sort of feeling like I’m continuing to deny myself of an experience I really want just because I’ve had really bad luck in the dating world. I don’t want to be a virgin for years more if I continue to not really have good relationship/dating luck, if that makes sense.

    Anyway, I feel like I’m rambling again lol, but thanks for all of the advice, and maybe I will try the self-exploration.
     
  7. Nickw

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    I think you will figure it out on your own once you try a little bit of self exploration. There are some "appliances" available on the market that will help with this. I suggest purchasing a set of different sizes and avoid the ones that look like penises. There are products that are more ergonomically designed that let you start on a smaller size and build up. Use lots of lube, the smallest size, and take your time. You don't need to rush anything.

    I won't get too graphic. But, you can use these with a partner also. I did that because you can learn to build up trust and become less self conscious about anal play before going to intercourse.

    If you do hook up for this, remember that guys that you meet on a hookup app may not the best choices in a lover. That said, as a married bisexual, there were not a lot of options for me to meet other gay and bisexual men but the apps. But, I turned away dozens of guys before meeting with a few. And, I became friends with these guys and built up to intimacy. So, you don't have to jump into bed with a guy just cause you meet him. Do not feel obligated just because of the expectations that build up on these apps. Be really, really, careful.

    Above all, this should be fun! Make that the goal and you may find the whole process less stressful!
     
  8. Mlh88

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    Thanks Nick for all of that advice, I appreciate it. I’m not quite sure about toys at the moment, that seems a bit intimidating to me, but maybe exploring a bit with my fingers to start and seeing how that goes.

    Also potentially with the apps, I was thinking maybe just being open to a friend with benefits situation as well where we can start with some kissing/oral play and maybe some fingering from him, and then we can move onto penetration as I feel more comfortable, seems like it could be a good solution where I can still have some of the experiences I want without jumping straight into the deep end so to say.

    Again, thanks for all the advice/help and tips.