Performance Anxiety?

History of me:
I'm a male, 17 years old. History of sexual activity, little to none.
I think it's important to say that I figured out how to masturbate at the age of 12 and I never really stopped doing it. It was very frequent at most maybe 7-10 times a day but on average around 3-5.
I'm uncircumcised as well and I was unaware until recently of certain things you have to do to your foreskin and head if they are an issue. My foreskin is not entirely stretched out maybe 90%, so there is still pain and discomfort when I'm erect and I attempt to pull back the foreskin to entirely unsheath the head. Additionally, any kind of touch to the head of my penis is uncomfortable and in a way very slightly painful, like a stinging.
I never really abstained from masturbating so I thought of it as an addiction, because I really never stopped, it felt good.
I've chilled down from the whole 7-10 times a day and I'm around 3 now, and I've learned it's pretty common for guys to masturbate so it's not really an addiction.
I've always used porn to masturbate, and for awhile it seemed that it was most of what I looked at in day.
But recently my life went for a flip and my interaction with females became almost none, to actually quite a few. I know a lot about sexual acts and what they are, but I have no experience doing them.

The issue:
So this is the issue. I have a friend who has quite a bit more experience than me. She's had sex 3 or 4 times. Me and her have a very close friendship, we're best friends and we'd probably be going out if it wasn't for significant reasons that she couldn't. But irregardless to that, she wants to in a way "teach" me and try things out for not only her benefit but mine too because I've always wanted to learn. I am entirely attracted to her in every way, and I do have deep feelings for her, so to me there is no reason to say no! I'm not going to back down from a opportunity given like this.

I've tried having sex with her twice already. The first time I had had a drink before I went, and I could barely get hard. (I found out later that alcohol is not good). Although I did get hard once, but as soon as I put on the condom I lost it.
The second time around I had abstained from masturbating for a couple days, I had no medication or alcohol and I was able to get erect in foreplay but as soon as I put the condom on I lost it again. More foreplay was able to get me erect again, with the condom on, and then when I tried penetrating I wasn't hard enough to put it in and I lost my erection again. I'm lucky that she is very patient and understanding and I've been doing research to why this is happening. So far, the best results are performance anxiety but if this is true, how do I become less anxious?

Don't try so hard... no pun intended.
You're mind fuc*ing yourself. You're getting all excited and anticipating the event that's about to happen and hoping you'll be able to do what needs to be done... and you're focused on "the act".

I say... just chill. Step back, slow down and cool off.

There's nothing like just holding and cuddling and touching in a non-sexual way. Perhaps you can give her a whole body massage and let her give you one. Get familiar with her body and let her get familiar with yours. Take a short nap with her if the two of you feel like it. There's nothing like a good massage to relax you enough for a quick snooze. Stop thinking about what you've got between your legs... and certainly stop thinking about her equipment. There's plenty of time for that...

Touch... play... caress... focus on giving her pleasure... keep it relaxed, humorous and light. If you're concerned about performing, or more accurately, NOT performing, just remember, there is a whole universe of ways to please a woman without having sexual intercourse with her. If you aren't sure about what she might want, or what to do, just ask her. I'm sure she'd be happy to teach you "the fine art of pleasing a woman". You said she wanted to teach you. Well, there ya go.

Take plenty of time for long and sensual foreplay... do everything slowly and gently... there is no rush. When you're both ready to do the deed, you'll know whether you're ready or not. You should be calm yet aroused, mindful of what you're doing and relaxed about it. Make putting on the condom a game with her participating... and not something you've got to quickly put on so you can put it to good use. Nope. Slow and easy with no rush and no pressure. Trust me, there is a time for fast and rough and heated, but this isn't that time.

In MY world, something like this whole glorious event shouldn't take anything less than two hours... minimum.

Anyway, I probably said WAY too much here, so that's all I gotz to say 'bout that!

Dan

My boyfriend is uncircumcised and I know condoms were something he hated when he was younger. I think since you are uncut, they may decrease your sensitivity a bit. I also know that if we've had lots and lots of sex, his penis will get sore too.

Insofar as to your nerves, I'd take it slow. Make your session something that goes from kissing to touching to grinding and the sex. What I'm saying is, if you make it about the intimacy between the two of you, and less about just sex, you can lessen your nerves.

Sex is learning experience, don't put the pressure of being the best ever on yourself. If your sexual relationship continues, you'll learn more of what each other likes.

Sent from my SPH-D710 using Tapatalk

Between Angel and Dan, there's little to add. I would wager near anything that your problem is pretty much solely nerves. That is, of course, quite understandable...the first time is typically a huge first step, and this is something new to you. Nerves are pretty understandable here.

Take it slowly...don't rush into sex. Explain to your friend that you're just nervous due to the newness of it all, and take things slowly...get comfortable with cuddling/kissing, then more intimate touching, and then, finally, sex. Don't walk before you crawl.

Good luck and hugs,
Harley