New Relationship - Can't Stay Hard

Hi!


So I don't know if I am posting this in the right spot but I would really like to see what people think! I don't want to give a whole life story but I guess I could explain that my sexual history includes three drunken hookups and one longer term boyfriend that I didn't really like. Yeah, sounds great, I know. But the point is, I am not super sexually experienced, but they men were always hard enough for intercourse.

Well I am with someone right now that I like and feel sexually attracted to and want to have fun with. I don't expect us to spend our lives together or be soulmates or anything but I haven't quite been able to get how to handle him. Well, he told me he was a virgin, and of course I didn't really care, I kind of figured it actually. He doesn't have much experience dating and doesn't really know too much about women. He is kind of socially awkward and doesn't always know the proper behaviours and actions in certain situations. No big deal. A lot of people are like that. I can look past it actually.

We started dating two months ago and went through quite a few dates before anything got heavy. He seemed to have a lot of passion. Well the first time our clothes came off and we started exploring he asked me if I wanted to make love. I was a little hesitant but said yes. Well, of course, he didn't know what he was doing really and I got kind of embarrased. Needless to say, no penetration happenend. I offered to give him a little oral pleasure because he got hard again but then he started getting soft even when I was touching and kissing him. He felt "bad" like "something was wrong with him." I said it was okay and we ended the night with really good backrubs.

Well we "tried" having intercourse two more times and things have gotten a little bit better. He now knows what position will work but he can't stay hard long enough to get it in! The second time I didn't mind again and told him I liked being with him and that it takes time to feel comfortable with someone. Well the next time we initiated sex again and we were raring to go and he kept "trying" to stay hard and I am laying there and we are so close to "making it" but nothing is going in. At this point I just want to be f*cked (to say it nicely). He keeps trying but we just can't do it.

I have never brought him to orgasm manually or orally so maybe I should try that next time? I don't know if I am doing something wrong or making him uncomfortable. I also don't want to ruin his first experience with a woman and make him feel inadequate. He has already lived his life with confidence issues. He thinks that he has to try and be worthy of me and doesn't want to disappoint me.

Now, the other question is, I am not devoted to being with him forever and don't know how much I should "help him along" and make our relationship feel uncomfortable. I don't want to dump him because he can't perform either. I don't want every encounter to go the way it has gone though. We need to change things up a bit. I don't want to put a lot of pressure on him.

Also, could some sort of diagnosed or undiagnosed mental condition have a role in this (depression etc.?) I mean the man is 23 years old so its not like he is a teenager or something. Is he really this nervous about having sex with a woman? I don't know that much about men but I thought they would be able to at least want to get off if a woman offered. Maybe he just can't express his desires to me. He thinks wayyy too much about things.

Let me know what you all think!

Thanks.

 

Men are visual, make yourself look completely hawt the next time you two go for it and see what happens. If he's on any blood pressure or anti depressant meds it wreaks havoc on a guys erections. He could be really nervous too, I've had that one happen to me once and it was with my one and only true love. Slip the homie some Viagra wtf, it couldn't hurt.