This is some damn fine advice!
[QUOTE=GoneForGood97;5958889]First off, hook up with the work girl as your first if possible.
The first time for me was also a girl from work. She came by my place to watch a movie (Pulp Fiction, still my favorite movie to this day). We're sitting on my sofa, and I put my arm around her shoulders and we're just watching the movie. Being the young (I think 22 or 23?) inexperience shy guy that I was, that was all I would do. She eventually pulled my hand down from her shoulder to her tit. At that point I knew this was going exactly where I was hoping. I started rubbing her tit, then we kissed, things took off from there.
If current me would give young me any advice, it's foreplay. Kiss for a minute. Once you get to the point where your undressing, ask her if she prefers sweet and romantic or dominant and rough (women your age will actually find your willingness to ask a big turn on). Now, if she says "rough and dominant" don't go too crazy. Since you're new, I'd keep things to a simply spanking on her ass and maybe pull her hair during the act. Don't try to get too rough when you're inexperience and when it's the first time the 2 of you are together. If she's into real rough stuff you can cross that bridge later. Just some hair pulling and spanking will do a lot of work. If she answers sweet and romantic, then kiss her longer, run your hands through her hair, kiss her neck, and whisper in her ear how beautiful she is.
Whether your being dominant or romantic, eventually pants will come off. This is the 2nd thing I wish I knew: foreplay is king, and cunnilingus your crown. Lick her clit with steady even strokes. If she moves your head, let her, and keep it where she puts it (she's trying to get your tongue where she enjoys it best). If she adjusts her hips, try to hold your head in place. Once she's enjoying things you'll know, and just keep a nice steady rhythm with your tongue. She may get vocal, start squirming, which will naturally make you excited, and you'll want to speed up. DON'T! IF WHAT YOU'RE DOING IS WORKING KEEP DOING IT JUST LIKE THAT! Don't speed up, don't change the angle, just nice and steady (trust me, she'll tell you if she wants it faster). If you feel confident enough, feel free to put one finger inside her and start fingering her (and for the love of all that's holy cut your fucking fingernails before the date. No chick wants to be figured by Wolverine's uglier cousin). If you're doing things right she'll get her first orgasm here. Or she may literally beg you to fuck her. If it's later, oblige her. If she orgasms first, give her time to recover, then ask her to return the favor. Assuming she gives you a nice BJ, enjoy it, but pull head up to you before you get close to finishing and tell her you want to be inside her. I'd recommend having her get on top facing you (cowgirl or cg). She'll put you in, then just do what feels right. With a condom you may have trouble finishing (and the nerves). That's ok. Just thrust and let her ride until you either finish or you can tell she's getting tired. If she's getting tired, you can switch to missionary or doggie, or ask her to finish you with her mouth. If she says "don't cum in my mouth" respect her wishes, and when you get lose give her a light "courtesy tap" on the top of her head and say "I'm so close" and she'll pull away and finish with her hand, or you finish with yours. Ask where she wants you to finish (if she's kinky she might ask for her face, otherwise just finish on her somewhere, it's easier to clean up, unless she says not to).
Good luck![/QUOTE]I wish someone had given me this tutorial back in the day! The only thing I would add is that since it's your first time, make sure you have an awareness of where the clit is. It's definitely higher up than where I originally imagined it. Google search an image so you have a good starting point. Otherwise, follow GoneForGood's advice, and you'll have a nice experience!