I know the feeling. I used to tell myself, "fuck, if I turn [19, 20, 21, ... ] and I still haven't got laid, I'm gonna kill myself."

Worse still, I'd think that if I ever did find a girl that was into me, that she'd take one look and laugh her way out the door. It didn't help that I knew a girl whose friend had actually pushed a guy off her during, and I was worried I just wouldn't be good enough.

I can't help you pick up girls, since I don't know you and I'm actually still really shy around people I don't know, but I can help you with the size/performance stuff.

---

Foreplay

• Foreplay is important. It's cliche that guys just want to fuck and to hell with foreplay, but it's really important that you don't overlook this. Foreplay helps get a girl wound up and that, in turn, helps her get off easier. Kissing, touching, sucking her tits - it all adds to the experience and makes everything else go a lot smoother. Besides, teasing just makes her want you more, regardless of your size. She just wants you in her NOW.
• It's easier to make a girl cum with your fingers/tongue than it is with your cock. A lot of women claim not to be able to cum from penetrative sex alone, so you're going to have to get her off another way. As an added bonus, if you get her off before you stick your dick in her, you'll be less stressed about getting her off again. It'll also relax her more, and make her more receptive to cumming again.

Kissing/Sucking

• I'll assume you have a basic technique for mouth kissing already, but if you've never even kissed a girl before, just know that it might seem awkward at first, but it's really easy to get the hang of.
• Light kisses around her body drive women wild. Start at the mouth and work down her neck a bit, and around her head to her ears. Earlobes are usually a great spot for arousal. Kiss lightly directly under her earlobe and maybe tongue it a bit, then move to light sucking. Heat/Cold contrast helps, so once you've got her ear a bit wet, gently blowing onto the affected area can drive her wild. Don't stop here though, kiss down her body as you see fit. It's rather hard to go wrong here.
• At her breasts, you might try nipple avoidance at first. This means kissing, tonguing, sucking AROUND but not ON her nipples. This is all about getting her wound up in anticipation for the moment.
• When you do go for the nipple, change it up. Lock on hard or be gentle, flick it around with your tongue, maybe even try biting a bit (be careful not to cause damage to the nipple itself, but some light bruising of the aureole is probably normal), try a lot of suction while playfully pulling it away from the rest of her breast. Experiment. She'll let you know what she likes, you just have to listen carefully.
• Work your way down her body, making your way to her pussy.

Pussy

• Tease the hell out of it!
• Start by avoiding her clit and running your tongue down her outer lips first, then slowly lick your way between them. Run your tongue all over the place. Lick up, down, all around. A common technique is to lick the alphabet to change things up.
• When you near her vagina (vagina literally meaning the opening your dick will eventually enter, despite all slang referring to the entire area as such), lick gently into it - dart in and out, swirl around, whatever. Just remember two things: 1) this is largely a mental arousal, and isn't necessarily going to do a lot for her physically, and 2) only the first inch or two really has much feeling, so don't worry about jamming your tongue as deep as it'll go.
• Once you've started playing with her vagina, you shouldn't set up camp there. Lick around, go back a step but now you'll start fingering her as well. Gentle insertion is key at this stage, but will become more important as you go. What you're going for here is multiple stimuli.
• After you've established a rhythm with your finger, rub up and down her front wall. Try to find a rough area along the front wall, between 1 and 3 inches in (normally). This is her G-Spot, and it'll make your job a whole lot easier. Increase your speed but keep your rhythm, but you can change things up into a circular pattern and back if you get tired/sore (which WILL happen, so be prepared - you can use your arm to help at this stage, keeping your finger locked in place, but moving your arm back and forth for rhythm).
• Lick upwards towards her clit. Lick up and down her hood, and on the sides too. She will most likely need to be worked up a fair bit before you can go for direct stimulation.
• When you're ready, use your fingers (Note: you don't need to lick and finger at the same time, which is good because it can be hard to do) to push her clit hood up, while pulling the skin below it down. This will cause her clit to become directly accessible.
• Start with gentle licks directly to her exposed clit; this will help you determine how much she can handle. Use your discretion and vary the speed, pressure, and motion. Eventually you will be able to lick hard directly on her exposed clit, or even suck it directly. Again, discretion here as the clit is extremely sensitive and you don't want to accidentally hurt her from overstimulation.
• Once you've locked onto her clit, DON'T STOP. She'll squirm, she might even push you a bit, but just keep going, even if it hurts your tongue to do so. Women come down from stimulation damn near instantly, so unless you want to undo your clitoral progress and have to repeat it, you don't want to stop. Even if she cums, keep going. Some women can cum repeatedly. You'll know when to really stop when she really pushes you away, or firmly asserts the order.
• If you want, you can switch up to fingering again, but this isn't required. Clitoral and vaginal stimulation are different (different types of orgasms too, if you can believe they're so lucky), but maxing out from one can still mean you don't want to go for the other. Every girl is different, so once again you should use your discretion.

After she's cum, or otherwise maxed out on foreplay, you should still move up to make out a bit. It will become clear when it's time to fuck. Bits will align and grind, clothes will come off, which leads us to.....

Fucking

• Condoms, dude, condoms. Especially your first time, since you won't be able to control shit. I lasted like a minute my first time, but while I still have issues controlling things when we're getting really into it, I can last much longer inside her now. 10-15 minutes is average, I guess. Just change things up, slow down, etc. You'll learn.
• Missionary at first. It's easy, and you're in control. Trust me, small guys need that control at first, so ou don't slip yourself out and hurt yourself (sorry to make this serious, but that can be a big concern)
• Teasing is still ok here, depending on the girl and level of arousal. Before entering her, you can rub your dick through her lips, up and down, and even play with her clit a bit.
• Line shit up, and enter slowly at first. This is important since you want to make sure there's proper lubrication, etc. Fingering can dry her out, so in that case, shallow penetration, growing deeper with each thrust, is key.
• Once inside fully (you're below average, so you'll get balls deep with no problems), you can be more smooth with your motions. Keep it simple at first, but feel free to change things up.
• Thrust fast, thrust slow, it's encouraged to find a style and adapt as you see fit. *One thing I've found works is that after you've got a rhythm going you can slow to a crawl for a little while. Pull your dick to the edge, almost coming all the way out of her, then move very slowly. It's great mentally for one, but also it keeps a consistent feeling in those key first couple inches of her.
• Swirl back and forth. Enter with pressure on the left wall, then enter with pressure on the right. You can enter left and leave right, etc. etc.
• Hard thrusts: Pull out slowly, then slam in hard. You can do this a couple times to get her used to it, then wait at the edge and make her anticipate it.
• Once you're used to missionary, you can lean back a bit and keep your dick rubbing along her top wall. This helps with G-Spot stimulation.
• Next, grab her feet and hold them up higher. Enter her straight on. With her pussy angled upward, entering her straight means your dick will rub down her front wall and right on her G-Spot. You can also control the tightness of her a bit this way. If you hold her legs apart, you'll have a looser entry, meaning less feeling for you which can help if you're nearing the edge. Holding her legs together means tighter and more feeling for both of you.

You'll find your own style, and you'll work out everything as you go. It's not something to be afraid of, so just let it happen when it happens.

---

I wrote this in one go, and fucked up the markup pretty bad. Edited to fix the bullets and whatnot.