Erection issue when putting in

This is so embarrassing even if I am just typing it. But here it goes. Before I had a wonderful GF. The problem was she is so religious she doesnt want to have sex with me up until we get married. Although we had sex before but that was just an oral sex really and uh you could say humping? Ive never cheated on her but then We broke up a year and a half ago because of some reasons that I wont mention here. I also never force her to put it in. I respected her belief. Here is the problem now. A couple of months ago, I tried to have sex with other girl. At first I acted though as if I knew what I was doing which is if you think about it I already had sex experience with my gf but not on lets say putting it in on her vagina. when she wants me to put it in, thats when my erection problem arise. At first I tried putting it in( I was using a comdom) but I wasnt sure if it has gotten inside of her. I felt warm on the tip of my penis but then I wasnt sure if it had gotten inside or was it only the tip of the vagina my penis is touching. I dont know what to do. I was so embarrass to look if it has gotten in. I tried moving my hips back and forth but I cant feel anything. Also I was not really sure if I was doing it right. or was I moving my hips in a correct way cause I am not that flexible. Ive gotten nervous and then before I know it my penis has gotten soft. I cant make it hard anymore. It was so damn embarrassing thinking about it makes me wanna bang my head against the wall. Also I am already 24, I should know how to put it in but I failed. its one of the reason also why I was so stress that time. I was worried about my performance. I was thinking if shell be satisfied. PLEASE HELP! What should I do? I really dont want to tell her I have no experience on sex cause clearly I do have but not on putting it in. Any PROs out there? PLease

Well, I'm not a 'pro', but I do know that when you start to worry about these things, it can start a vicious circle.

Sex is not a performance. You shouldn't feel under pressure to do everything absolutely perfectly. When this sort of anxiety creeps in, you start thinking about what you're doing instead of going with the flow.

It's clichéd, but the only answer is to take more time over foreplay, and keep your focus on your partner rather than how you're 'performing'.

I'm not a pro either. But a couple of things that partners have mine have done in this situation. Include just asking. I didn't think any less of them for not knowing! I was too focused on what we were doing to be picky like that.

And also, I've noticed men touching themselves and me down there. And yes, that could be checking the condom is OK. Or moving a stray hair. Etc. But now that you mention it, I strongly suspect it's for this reason. And all of these have been men who've had sex numerous times before. Sometimes it just plain IS hard to tell. Because depending on the position, the cock can be quite tightly held. Even if it's not in. There's nothing wrong with you and this isn't something you should "magically" know.

Graveyard's really right about not stressing about it, though. And in terms of performance, try not to guess too much. Better just to ask. "Is that good?" "Is that fast / slow enough?" "What else do you want me to do?" And so on.