What sort of advice are you looking for?
Thanks for the honesty and the questions.
First thing I would say, sex is not about pleasing the women, it is about pleasing ourselves in a way that also brings pleasure to the woman and deepens the relationship.
If you are cool with the fact that you are a virgin, there is no reason why she shouldn't be as well.
If you want to have sex with her, you might tell her straight out that you are a virgin, and that you may well want to take your time with getting comfortable with her and the experience. I would think that a lot of women would be excited by this disclosure, as they will know that the experience could really means something special to you.
Like everyone, men and women a like, you have the right to have a good experience with sex, and to be able to take your time and explore pleasure and connection in a way that is compatible with your partner. I hope you have a good experience with it and that it inspires you for much more to come in the future.
Does she know of your virginity?
Alright, I'd start with that. I know girls who avoid virgins at all costs. I also know girls who seek them out specifically. If she's cool with it, then here we go;
Sex is the journey, not the destination. Your best bet is to let her know up front the status of your prowess, non existent, and she's going to need to be in the drivers seat for a while. She may dig that, she'll have a chance to create a lover specifically tailored to her wants, needs and desires. But, when you've got the mechanics down, don't be afraid to experiment. Like I said, it's the journey. Try everything once, if you like it, try it again. If you don't like it, try it again just to be sure.
To the specific mechanics; you can try long, slow, multi-day, multi-orgasmic tantric sex. Or, you can go for the porn standard; three positions, three minutes each, cum on her face. Most days you'll want to shoot for somewhere in between. A mention about porn positions, don't try them: A) you're not a professional, you will hurt yourself; B) they're designed for the viewer, not the participant.
To add on to what Jay said, don't be overcome with trying to please her. Certainly it's one of the goals, but not the only goal. Making her pleasure the goal can lead to a lot of resentment and deception, not the things we really want in bed, unless we're into that. Besides, as Deborah Jeane Palfrey said, Republicans are better in bed than Democrats, because Republicans DGAF.
If her pleasure is going to be the goal for a session, demand feedback. Male physiology allows for very clear evidence of satisfaction, female physiology not so much. Lack of feedback will also lead to resentment and deception.
You look pretty young in your pic, one thing you're going to have on your side is recovery time. Use it to your favor. After you blow your load in a second and a half, spend a considerable amount of time poking and prodding and licking and pinching and sucking and just exploring until you're ready to give it another try.
You're right--reply function not working..
We can all get caught up in worries if the woman is satisfied or not.... In my experience, that concern is certain death to good sex.
That is why I was suggesting you might tell her flat out that you are virgin and that you might want time to explore. For example, my first time lasted about, uh, two minutes. Probably not a lot of women would be satisfied with that type of endurance! But, if they appreciate that this is a guy's first time, the significance of that fact should outweight any endurance issues, I would think.
Also, you might consider that a lot of women really get off on foreplay and oral. You can have a lot of fun, and also build up sexual endurance, but prolonging these aspects as you develop the relationship with her.
I first had sex at 15, and was always good around girls. That said I was still intimidated when I first entered a sexual relationship about three years ago (I'm 20 now so I was 17), as until then sex was only ever a one off.
my advice would be:
learning to screws like learning anything else, practise practise practise, and if you wanna learn fast dive in.
if she is a good lass she'll be fine as long as you tell her at an appropriate time (NOT when shes putting a condom on with her mouth), and if your fully honest about being intimidated; if you can do that then have one three day weekend sex marathon you'll likely overcome any doubts about performance.
you might have a low sex drive, but you also might find you don't, and there's only one way to be sure...
Sex outside of marriage is overrated. If you start having sex with this girl because she wants it, and don't end spending your life with her, you'll feel like your heart has been ripped out and stomped on, and she'll likely feel the same or worse. I strongly urge you to either develop a caring, meaningful, sex-free relationship with her, and consider the idea of marriage, or stay single and enjoy your unadulterated youth.
The divorce rate in this country is somewhere around 50% because sex is cheap and people have little concept of what love is anymore.
Love is not a magical feeling that comes over you and never leaves if you've found "the one". Love is a choice/effort that has to be made constantly. That glorious initial affection will fade in any relationship, and each party must consciously choose to continue loving the other if there's to be any hope of a future for the couple.