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Hi, I'm 17 and I've been dating the same girl for over a year now.For the past few months we've been pleasuring each other but never managed to have sex because we could never get enough time alone or didn't have contraception.I regularly masturbate, on average every 2 days, because we weren't able to have sex. I also have a heart problem which causes problems with blood flow (I couldn't do much PE in school and I have very little muscles).Recently we have gotten more time alone, so obviously we tried doing more things together. A few days ago, my girlfriend was attempting oral on me and I couldn't ejaculate and eventually went limp. She has performed oral before and I was able to maintain an erection for some time, but didn't ejaculate because someone returned home, and we had to stop or we would get caught (We were trying to avoid being caught at this point).So my first problem is that I couldn't maintain an erection/ejaculate during oral. My second problem is that today we tried to have sex. We used a condom and I kept losing my erection when trying to penetrate, only regaining it after some more foreplay, then losing it again trying to penetrate. I don't usually have problems maintaining an erection, but it takes a while to get one when masturbating.I told her I thought it was because of the condom that I kept losing my erection.What is causing me to lose my erection? Is it wearing a condom, my too-regular masturbating, my heart problem or some combination of those?

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Firstly, many (possibly most) guys, do not enjoy oral sex as much as they think they do. There's nothing wrong with that, but internet porn and school gossip seems to put pressure on young couples as boys think they have to enjoy it and girls think they have to do it. If you're not enjoying it that much you'll subconsciously become anxious about it and you'll lose your erection. This then makes the girl think she's unable to satisfy you which makes it more difficult to relax next time.

Secondly, if you're losing your erection before sex it's almost certainly because of anxiety. Condoms do decrease sensitivity and your heart problem cannot be that big a factor if you're able to get an erection to begin with. Masturbating twice a day is not going to help, so if you know you're going to see your girlfriend later that day don't masturbate.

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Thanks for the advice.
I didn't feel as much pleasure from oral as I would have expected. Yes I was feeling quite anxious about it... I think we both were really. We were both having a bit of foreplay today, more relaxed about it, and I was able to keep an erection this time, so I think it was more down to being anxious.

I've also tried cutting down on how much I masturbate, only twice in the past week since I posted.

Overall good and sound advice. I'll keep this in mind in the future!
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