This is an excerpt of a conversation I had with a friend on a subject that can be an integral part of our young lives.
DancetheOrange: okay, well... where do you want me to start?
Curious Young Man: how bout just some quick pointers?
DancetheOrange: alright: 1) playing around with where/how fast/how hard you do it is cool in the beginning, but when it comes to the point that you're specifically trying to get her to orgasm, a steady rhythm is key. If you change it up too much she'll lose some of the build up and it will take longer.
Curious Young Man: is this in regards to fingering and oral?
Curious Young Man: emphasis on and
DancetheOrange: AH! yes that was the second point, is that you need to have two fingers inside of her while you're doing it [oral]
Curious Young Man: always?
Curious Young Man: which two?
DancetheOrange: well, once she's wet enough to accomodate
DancetheOrange: index and middle? I don't think it matters (though those are the ones you'll have the most control over)
Curious Young Man: and how should they be positioned? vertically or horizontally?
DancetheOrange: whatever is more comfortable for you, it doesn't matter. THOUGH, if you want to be getting her g-spot at the same time then they'll need to be horizontal with the pads of your fingers facing up
Curious Young Man: got it
Curious Young Man: steady rhythm, two fingers, horizontal, pads up
Those seem like pretty basic points, but there are some guys out there that seriously have no idea. Some things that are good that I didn't mention to my friend:
-Kissing and lightly biting the stomach and hips, gradually working your way closer... This is playful and strangely arousing (can also be done on the thighs, but the stomach is more sensitive)
-Going down, coming up for some kissing, going back down... This I'm sure varies by person, but it can be really erotic to kiss someone when they're slippery and smell like you (sorry if that's too gross for some people, I'm just trying to be helpful)
-Scratching. This isn't unique to oral; from simply making out up to fucking like monkeys it's applicable. In the case of oral, however, it's best to scratch with moderate weight (not so light as to tickle, but not so hard as to draw blood) around her stomach and hips and buttocks (ie what you can reach) with your free hand. It adds to the sensations, and can make her more aware of the rest of her body and thus have more of a body orgasm than just a uterine one. Not that anything is wrong with a uterine one, but... sometimes it's a special occasion and that calls for something a little more special.
With any sexual maneuver, the level of enjoyment it gives can vary greatly from person to person, and if the girl doesn't seem to respond positively (or flat out asks you to stop), don't do it again unless she directs you to. Everyone is different, and while it can be exciting to try new things, pushing them on someone who isn't as into it can be a huge turn off for that person.
Alright, I think that's a good start for anyone. If you still manage to mess it up... don't blame me, I gave it the ol' college try.