Hi there,

I don't where to start but I do want to keep this brief without going into my life story...

I have had a sheltered, strong Christian background where the Christian teaching of no sex before marriage was something that was really cemented into my mind from early on. I would be really shocked when I heard other Christians or anyone else for that matter who would having sex. The actual sexual intercourse act represents a huge thing in my mind, always has done. Even though I did have had serious relationships and a few flings as well where I did get the opportunity to have intercourse, I held back almost every time, because I felt it was the wrong thing to do. So I have done "other stuff" but just not the actual act of penetration. But now at almost 30 now and still not married, to be honest I am starting to lose my patience...

The first time when I was 19, I ended up being overwhelmed by guilt and fear since it was something terrible and withdrew at the last minute.
Then I didn't try again for many years until this year... 10 years later now.

But I FAILED, miserably. Tried on two occasions and both occasions I failed.

Both times, I was fairly hard to begin with whilst making out with my last girlfriend and then went to get a condom but as soon as this happened I noticed how I felt that wave of anxiety come over me. My heart started to beat faster as I knew OK this might be it, I’m finally going to have sex for the first time. Tried putting it on and struggled to get it on and as a result it went soft again. Now at that moment, along with anxiety came the frustration and self pity. I was like inside "here we go again, I still can’t do this" "not again" Eventually I managed to get it on despite it being flaccid and it wasn't getting hard anymore and I had to actually touch myself in order to get it hard again. But I noticed how it wasn't really all that hard and in the end I just stopped and gave up. I didn't actually look where I was placing my penis and just thought I'll get it in the general area and it should just slide in. But I couldn't actually get it in, I don't know maybe I was nowhere near the actual area, anyway it just didn’t happen. It just seemed like a difficult task. I guess after masturbating for so many years, the idea of intercourse might seem slightly alien perhaps?

I should also mention that me and my girlfriend were having some serious issues (non sexual) literally less than 24 hours before so I wondered if that affected things too. But I also believe my Christian beliefs and conviction and being celibate has now had a hugely NEGATIVE impact on me, myself esteem and my overall well being. I feel I deserve better than this after waiting for so long. As I've got older, I'm starting to become frustrated which no doubt leads to anxiety and probably makes this entire act into such a big deal.

I’m not sure where to go from here. I'm torn. Part of me still wants to wait until marriage, as I have waited for so long now I might as well... but when will that be! Then the other part of me wants to finally experience this so I can finally just say I've done it and prove to myself that I can do it. I suppose right now, it's affecting my entire self esteem figuring out whether I can actually have sex!

SO I guess I would like to ask... how can I know for sure that I can actually do this! I thought maybe getting a fleshlight or some kind of makeshift vagina? I know you can create a home made vagina but how accurate is this? Obviously I know a real person is the only way to know for sure... but as that's not possible at the moment, what other ways could there be? Health wise, I'd say my diet could definitely be better (I should less sweets and sugar) but I don't smoke or drink at all and I exercise say 1-2 times a week. Also I do get morning erections from time to time, like little while ago I was getting them every morning for about 2 weeks.

I JUST NEED TO KNOW IN MY MIND THAT I AM CAPABLE OF DOING THIS!

I fully empathize with you, having grown up in the same atmosphere. My parents believed sex before marriage was an instant ticket to Hell. And, to top it off, my father was our church's pastor and reminded me frequently that I was the role model and shining light for all the parish's youth..

My question to you is, will you be able to perform on your wedding night? Will a wedding ceremony and marriage certificate be the magic that will allow you to perform successfully with your bride?

My suggestion is to find a good therapist who deals in men's sexuality.

No, the plastic or make believe ones are not the same, they are just a fancy way to masturbate if that is what you like.

And 30 is not the end of the world, men are still having sex for many more years, And having sex has nothing to do with self esteem, it means your penis can stay hard and you have a willing women.

Should you wait, that is your choice, some men do, others do not. It is a matter of what your conscience believes and wants. If you do, will there be guilt, you can not undo it, once done.

I would focus more on 'why haven't I found the right girl' and finding the right girl. I know and can relate to the cemented into me thing. But the Bible also says about if you lust (after a girl) then you have already committed the act and you say you did up to the act sooooo. Not condemning you just sayin' you need another approach and praying and seeking for the right girl in your life. Hooking up with the wrong ones in life gives you some life lessons but at the same time it really holds you back from getting where God wants you to be. So again find the right girl. If you are having a hard time finding the girl for you look deep in yourself and see if there is anything you are doing wrong. Like my grown son has never found a girlfriend because he wants the right one (and Lord knows I never enforced that in any of my kids). I told him the other day, when he met a girl at the church he started going to, that he needs to solve some unresolved bitterness in his life that makes him blow up before God is going to bless him with a girlfriend. If he doesn't it will just fall apart. God is opening his eyes and doing a work in him so I think it could work if the girl is interested in him. Your worries are nothing more than worries you will do fine