Figuring out how to convince your girlfriend to do 69 isn't all that difficult (especially if you throw in a little alcohol.) But, in all seriousness, if you feel you're ready to take it there, it's not all that hard. For the uninitiated, read on.
- Have trust. Look, you're asking someone to stick their junk and ass in your face. Having complete and total trust in this situation is paramount. Work up to it. Don't just be like, “baby, I want your ass an inch away from my nose, let's 69.” That's a recipe for disaster and a lonely you for the rest of the night (and maybe for good.) Make sure you and your girl have been intimately acquainted enough to allow her to enjoy a good 69. If she feels uncomfortable, she won't be getting anything out of it, which means you won't be getting anything either.
- Strike while the iron is hot. Don't plan this one out. This is a spur of the moment kind of event. Work your lady up, get her all hot and bothered, and then, while she's completely sucked into the moment (pun intended,) flip her over and get to it. Sitting around talking about how to plan it all out not only will ruin the moment but will also guarantee you a night of the same old boring sex. (if you get any at all.)
- Drop hints. Again, don't be all full out, “baby, let's do 69!” As you get to know your girlfriend and as you progress in your sexual relationship, be a bit more open with what you want and encourage her to do the same. You can drop subtle hints over time, letting her know you're wanting to get a little more freaky in bed. Before you get all nervous, realize she will be doing the same. Pick up on her hints. She wants to try this stuff just as bad as you do, so pay attention. If she says things like, “I really like it when we are both receiving pleasure at the same time during sex,” recognize that as an opportunity to drop your own hints. You might suggest, “well, I really like going down on you and I really like it when you go down on me,” and then see what she says. Play the game, son!
- Have confidence. Look, we all know ladies like confidence (think about why you lost you last girlfriend.) Anytime you're planning on doing anything “unconventional” in bed, you have to be confident. If things go badly, oh well, so be it. You won't know until you've tried. The worst she can do is slap you and spread all kinds of horrible lies about you all over town (although, you'd probably benefit with other chicks as a result, so the glass is half full.) The payoff will be worth it, as you can enjoy the satisfaction of pleasuring each other at the same time, as well as the satisfaction of giving hive fives to your buddies when you tell them about how you did a 69 with your girlfriend last night. Won't they be jealous?