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Relationship is great, but the sex is a struggle

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So I didn't know exactly which thread to write this under, but it all stems from relationship stuff so I figured I'd go with this one.

I've been dating this guy for almost four months, and everything is absolutely perfect. We met through a mutual friend at school; I just turned 23 and am in my fifth year in college, and he just turned 19 and is a Freshmen. The age gap was a bit funny at first, but now it's not a big issue. Our relationship is so easy, fun, simple, no-pressure and no negatives. We just GET each other. It's hard to explain without making it sound like a fairy tale. And trust me, though I've only been in a few relationships before, I feel like this one is on a totally different level.

Anyways, the reason I am posting is because I am really nervous about our sex life. Now, we've moved slowly with our sexcapades, and we just let things take their natural course. We are both very comfortable with each other, but a few things have concerned me. First off, although it's never specifically come up, I am very much under the impression that he is a virgin. He's told me he's had experiences with a guy or two, but has never mentioned actual anal sex. Now, the problem for me is that I am not a gay guy who's into anal. And if it has ever come to that, I've always bottomed. I'm Asian, and so I unfortunately am not well endowed at all and that is why I gravitated to being a bottom. Definitely a confidence killer, but that's another story. So my main question regarding him being a virgin is, how do I let him explore whether he likes to bottom or top without it being awkward? Especially because of my size, I'm not really capable of topping. Should I get a penis sheath extender if he wants to experience bottoming? Should I have a specific conversation with him about anal sex and just be an open book?

Secondly, I cannot seem to cum when I am with him. Like, the research I've done seems to suggest that I might be suffering from sexual performance anxiety, which I can certainly pinpoint various moments in my past that would perhaps lead to this issue. I think in the past, too, I've put myself in degrading sexual situations and have always wanted to focus on the pleasure of the other guy and not me. With my boyfriend, I have so much fun and am certainly turned on when we are being sexual together. I just can't seem to finish. I have a very sensitive penis, and so blow jobs and hand jobs are sometimes more irritating and painful than pleasurable. But even when I jack myself off with him, I can't finish. When I am alone, though, I have no problem cumming buckets. Is it because I am just used to getting off alone? Should I tell him to maybe try sucking me differently, or stroking me more gently? I don't want to be rude or seem like I'm not grateful.

All of this hasn't caused any tension in our relationship. I just don't want it to get in the way as we move forward. We both want to have a very open and communicative relationship, but is there no way to bring these topics up without it being awkward? Thanks for any suggestions; I've been so nervous and really needed to get this off my chest.
 
I think the biggest thing is that you are happy together. If you are really concerned about sex with him, you should talk to him about it. Communication is the key to every relationship. If he really cares about you and wishes to pursue a serious relationship he will be understanding, and willing, to talk about sex. Sex is important but its not EVERYTHING in a relationship.
 
Continue doing whatever is fun and brings enjoyment. Talk about absolutely everything. Be clear on what is pleasurable and what isn't. Teach each other how you each like to be pleased. Try mastubating less alone so you're more horny than usual when you're together. I also wouldn't give up on topping. Keep experimenting. Your anxiety should lessen once you stop having expectations related to mechanics. All that matters is you you both feel good. Best wishes.
 
Ive had similar problems in the past. It sounds like you have a great man in your life. Good start. I think you need to re-program your thinking patterns around sex and just enjoy each other. Let him pleasure you as much as you want to pleasure him. Relax. Have plenty of foreplay. Communication is also very important. Tell him what turns you on.
 
Calm down, take a deep breath and relax. You're putting too much pressure on yourself and worrying about things that you don't need to worry about. You have a good relationship with someone that cares about you. You are creating stress and anxiety over the size of your penis. Dude. You can't change it so enjoy it. Judging by what you've written your bf doesn't seem to have an issue with it. Your feeling inadequate and you aren't allowing yourself to enjoy sex. In other words you have penis envy. You didn't say how big your penis is but I'd be willing to bet you are average. Even if your penis is less than average there isn't any reason you can't top if you or your bf wants. As long as your dick gets hard, it works. Anyone that doesn't want to be with you because of the size of your penis isn't worth being with.

If it's really causing you that much stress talk to your bf about it. If you get along with him as well as it sounds he will tell you you're worrying about nothing. Enjoy your sex life. The problem isn't your penis. It's your emotions.

Steven.
 
It's like you both need to talk and reinvent your sex life, spice it up do in diff- places, times, outside, weekend getaway. My honey and I have been together for 28-1/2 yrs and ous sex life is better now than at first, and we always keep it spicy and just try all kinds of things, things you never have done but always wanted to.

We know each others wants and needs now, how to realy get each other off, or surprise each other with something.

But always communicating is important, and leads to a healthier LTR. And fun too.
 
I would also recommend telling your boy about your fears. You will be surprised at how supporting he is likely to be.

Agreed. I cannot emphasize this enough. Communication is key and avoiding the issue is only going to exacerbate it. You say that you both "GET" each other. If so, then simply talking about it may quell your fears and anxieties...and open you up to a whole new horizon. Good luck!
 
All of this hasn't caused any tension in our relationship. I just don't want it to get in the way as we move forward. We both want to have a very open and communicative relationship, but is there no way to bring these topics up without it being awkward? Thanks for any suggestions; I've been so nervous and really needed to get this off my chest.

Look- bluntly stated, if you're adult enough to be having sex, you're adult enough to have a conversation about sex with your partner. Yes, it's awkward to have the conversation the first couple of times but it is any more awkward that seeing each other naked?

Over in the Health & Wellbeing forum, there are a group of stickies at the top of the forum where other members have asked about these same questions. It is very common for guys to have trouble coming with a new partner or when they have a lot of anxiety about sex issues.

And forget about wanting to have a big dick. A big imagination is going to get you much further in bed.

You're going to find that if you get these things off your chest by having that discussion, a lot of these anxieties will go away and that's going to make sex better for both of you.
 
Thank you all for your comments! I can't tell you how much I appreciated the encouragement and suggestions. Just to update you, my boyfriend and I had an amazing talk a few nights ago, and that has led to us opening up even more in just the past few days alone. Last night we went all the way for the first time, and my boyfriend is no longer a virgin! It was by far the most erotic, romantic, and loving night that we've ever had together, and certainly the best night and most wonderful experience I've ever had. Topping for the first time was so much fun and really, really exciting, and my boyfriend came just by me fucking him. I guess that would be a good omen? :D

The only drawback was that although I was close to cumming at least three different times, I still wasn't able to "get over the edge." While it was obviously a bit frustrating, I was hard the entire three hours we made love and I was very careful about letting my nerves get in the way. And you know what? Throughout this all, my boyfriend has been so sweet, encouraging and considerate and is not at all offended in any sense that I've yet to finish. I thoroughly enjoyed myself and am much more confident that I am slowly making some personal headway on my anxiety.
 
No - do not get a penis sheath extender. Here's why: you may THINK you are small but if you use such a thing HE may think you are because he may think "wow...why would he need that" "why isn't he confident enough in himself" etc.

As the old adage goes: "Comparisons are odious" and focusing on your size in comparison to others means you will not be exuding self-confidence ...You need to focus on all your attributes and be proud of who you are physically and non-physically and present yourself to others with pride and self-confidence. Not easy I know especially in the younger years but the sooner this is addressed.

If he's a virgin then you have a wonderful opportunity to be the "experienced" guy and show him what you know too. In any case, it's a great process of discovery and should be enjoyable not so stressful. Focusing on the journey or process of sex not the result (orgasm) may help. There was a book a long time ago about whole body orgasms or "Becoming Orgasmic" and that was part of the theme - NOT to focus jsut on the cumming.

Well, hope some of that helps.
GL and keep us posted/
the better.
The second issue of not being able to cum with him is more a matter of trying different positions. it's easy to cum when alone because you likely have that all worked out what works best and so on. But with another it is more complex and takes communication to figure out what his needs are too and focusing on that may get you what you want instead of just focusing on your self and your need to cum.
 
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