You can't do that enough. Take it slow and let her guide you. Block off an afternoon so neither of you feel rushed. Actually, this is probably even more of an issue for her than you. If she starts the day off thinking "we're going to have sex today" that might make it hard for her to just relax and have a good time exploring. So I'd just make sure she knows you're happy to take a leisurely, exploratory pace if she wants to.
But be ready with protection. On the other hand, once she's turned on she may just want to get down to it, in which case, have fun! Oh, and I once heard some great advice on Dan Savage's podcast to a caller in the same position male with a twenty-something female virgin partner.
He pointed out that, while it is important not to push her, she may be one of the many women and men! So if she seems to be looking to you to take the lead, don't be afraid to do so, as long as you're checking for consent, excitement, etc. This was true for many of my friends I've talked to as well.
The second time less painful, but still not much fun. After that it was great. Use a lot of lube, take it slow, and don't expect it to be all that awesome for her right away. I think it would be a good idea to experiment a lot with oral and with your hands before trying any PIV, just so she knows that sex with you is fun, and can keep that in mind even if the penetrative stuff isn't so great at first.
Make this one special, because it can have a lasting effect on her sex life from here on out no pressure, right? Seriously, don't get wrapped up in performance. What have you done with women in the past that they enjoyed? Try that on her. Just take your time. Another thought-use lubrication along with protection. This being her first time, she will need to "acclimate" to the penetration. If you guys are dating, make it special!
Take her someplace romantic, start with a nice meal, etc Taking it slow, yes. One thing to try is exploring her with your finger. Lick your finger first, and then playfully slide it in. This will ease her into the experience. Ideally, you will bring her to orgasm, allow her time to recover and then start back up again.
Penetration should happen right before her second orgasm, when she is so turned on that she will put up with just about anything. You will meet up with resistance if her hymen is intact. Do not attempt penetration unless you are fully erect. Anything less will be painful for her.
Over the next couple weeks, using plenty of lube and time, get her used to two fingers, then three fingers. This will make make the penis more comfortable for her.
I know for some women it can be painful and a bit annoying. There's a lot of mythology wrapped up in women's first times so I'd just be prepared to roll with it and not get weird if there's a little blood, some pain, no pain at all, a lot of lube needed, no lube needed, towel needed, etc.
So many people get bent over not being "normal" sexually, that I think an important thing with people who haven't has as much experience is to stress that it's more or less all normal and that it should be at least somewhat fun.
Like more than just making out or the like? Hand-play, oral, etc, etc? What was most important for my first time I was in my teens was knowing that I was physically comfortable with my boyfriend and that I trusted him. We did LOTS of messing around before we had sex the first time, so I was familiar with the sensations of him touching me and me touching him, and what it felt like laying with him naked and how he reacted to certain things and how I reacted to certain things.
By the time we had actual penetrative sex it felt almost like an afterthought, or a by-product of what we were already doing. So if you hadn't gotten to that point, I would strive for that first. When it comes time for the actual deed, plan a whole afternoon or night or whatever because you may have a few false starts before she actually feels ready.
Laugh and be comfortable with each other first. But don't worry about that too much and take it slow. She's undoubtedly talked to a gazillion of her girlfriends about the possible pain and is probably prepared for it. Good luck and have fun.
And my sex life still ended up pretty amazing, and I even had decent sex with that same guy later. So really, it is okay if it goes horribly wrong. Being relaxed and willing to laugh is probably the number one thing, for both of you. If you're going to do lots of finger penetration, make sure your hands are CLEAN, and your nails are short and you have no weird hangnails.
Also, test lube on a non-inside part of her first to make sure she's not sensitive to it before you go putting it in hard-to-reach places. Don't ask me how I learned that one. She won't know how to guide you.
She won't know about, you know, guiding you in. She won't know about postures and hip angles or the right moment to put on the condom or how to touch your weenie or anything. You will have to take it slow and read her signals, yes, indeed, but you will also need to be the one who knows how to do stuff. If you can make sex fun for her a few times before penetration so much the better, if she's game for it maybe go down on her or use an egg or a vibe down there not so much for an orgasm so much as to get her feeling good and feeling sexual, though an orgasm is nice too.
Just because she's a virgin doesn't mean she hasn't experimented on her self, so asking her if there is anything she likes is also good. I remember my first time oh such a very long time ago, I vaguely remember dinosaurs still roaming the earth things I remember, being surprised that I had erogenous zones, up until then I assumed all the action happened below the waist, but hey boobies can be fun for everyone.
I don't know why but I didn't realise just how weird the angles actually were down there, I sort of thought it all just slotted together like Lego so you might have to gently guide her to the right angles, leg positions etc. Please don't keep going on and on and on the first time trying to finish off yourself inside her things get owie down there pretty fast, a little penetration and then maybe pull out and then back to sex play.
You don't have to promise undying love or anything, but be thoughtful of her. Oh and make sure you practice safe sex she might not be on any form of birth control so take care for both of you and have some condoms handy.
I think an important thing with people who haven't has as much experience is to stress that it's more or less all normal and that it should be at least somewhat fun. I've had sex with a fair number of virgins, and none of them ever bled at all; only some found it painful. The range of "normal" for first time sex is really large, and it's hard to generalize.
It sounds like you are doing the right things, and you are on the right path. Don't focus on trying to get her off - the last thing a girl needs is to feel like she's doing it wrong because she's not coming and you're obviously trying really really hard.
She's probably nervous about being crap in bed compared to your previous partners so if she's anything like me she'll be reassured by you clearly enjoying yourself. You might want to put a towel down just in case she does bleed so she doesn't worry about messing up the sheets.
That, and you should try to make sure that, if it's not likely to be all that pleasant for her pain sucks, and there's likely to be pain , that you do as much as you can to make the rest of the experience as pleasant as possible. Nice, clean, airy room, comfortable, lots of reassurance and cuddling before and after. You've already got the right idea, let her decide the pace. I hope things go well for the two of you.
Do your best to make it as pleasant as possible, but don't go into it with expectations. It takes a while to get to the point where it's fun, and it takes a while to get to know each other in the bedsense, too. I know it's not very romantic but urinary tract infections are not uncommon when women first start having sex see honeymoon cystitis and it's not a bad habit to get into for the long term anyway.
My first time was pretty uncomfortable so I'd agree that using fingers at first and lots of lube is a great idea. A cool compress and a Advil afterwards might help with any swelling or pain she might have. Basically, just relax and enjoy the wonder of the human body without obsessing about any end goal The world does not need to know or ask how it went afterwards.
Not that that happened to me ages ago or anything. It does not take a town to take virginity! So don't stress too much. And please, don't let it be you who makes a big deal over her being a virgin Follow her lead, all the way. Obviously, I'm letting her set the pace, and am not pushing her to do anything before she's comfortable I remember so clearly how frustrated I was with my first sexual partner trying so hard to be all respectful and not push my comfort level and take his cues from me in deference to my virginity.
While I appreciated that conceptually, it actually made me feel even more inexperienced and idiotic. Why the hell am I driving, I wasn't the one who had done this before? Sexual intimacy can be scary and kind of embarrassing, and all his careful tentativeness didn't exactly inspire my confidence or make me feel sexy.
So, here's my terrible first time story: Yes, yes, consent is very very important. This does not mean that pausing mid-thrust to make sure it's not hurting too much was the kind thing to do. I already said yes, and now I have to affirm again that this part here that hurts is what I want right now while we're in this awkward position and I have no idea what's normal or how it feels to keep going but we're going to only do whatever I say is okay now?
Uhhhhh, whhaaatt, I dunnooooo?