If you're new here, you may want to subscribe to my RSS feed ... or subscribe to new posts by email. Enjoy the site!

Q: So.. After a horrible, and embarrassing night with my new boyfriend, I come home to my laptop to solve my problems. I am a bigger girl, only have ever been with one guy.. Not very experienced. I love sex, but I am so damn insecure it's ridiculous. So tonight, the time comes when my boyfriend wants me to go on top. Now, again, I'm a bigger girl, and not much experience on top. So… now what? This is so embarrassing, but what do I do? I usually would just roll my hips or lift my self up and down, but it's always very slow. So what do I do? Bounce? Ugh.. big girl on top, bouncing… Cannot be very sexy. Help, please.

Aww honey. The first time a guy asked me to be on top, I was a skinny, skinny little thing, and I felt exactly the same way you do … what the hell do I do now?! I was sooo embarrassed. And then, god help me, after a couple minutes, he actually said I was boring him. So. That brings me to my first question: Did he do or say something rotten to make your night so horrible and embarrassing? Or was it one of those things where stuff doesn't go right and you're just embarrassed in your own mind? Because if he did something inconsiderate, he doesn't deserve the effort you're putting into this whole thing…

Now, if he didn't do anything rude, I've thankfully learned a few things since I was a skinny, embarassed girl—and I asked a couple friends for feedback too, from both the male and female perspective … because girl-on-top still isn't my fave position. ;-)

So, first off, keep this in mind: If he wants you to get on top, it's definitely partly because he likes looking at you. Never mind the movies and magazines, most guys like a woman with some curves! :-) So (even though I know it sounds impossible when you don't have much experience—and it sometimes is, even to skinny girls) try not to worry about how you look. He wants you up on top, remember? That means he wants to look at you! Also, try buying a sexy little teddy or babydoll to wear, if you're still worried about how you're going to look… it's amazing what a sexy little piece of lingerie can do for a girl's confidence.

Now, let's assume you're about to go ahead and give him his wish… If you enjoy giving blow jobs, kneel down between his legs and do that as soon as he rolls over on his back. He's gotta like that, and it gives you a chance to get him all hot and bothered before you have to take over the spotlight. ;-) Then, craaaaawl up his body, and rub his cock all over yourself on the way up. That'll keep him hot and bothered! Then, once you're up on top, tease him a little before you put him all the way inside. Grab his dick and rub it against yourself, or kneel just above him, and grab his hands and put them where you want them (or put them in a place you already know he likes to feel around), and make him wait for it a little.

Once you're actually into it, I've found it's really easy to get the guy to help you out. You don't have to just bounce and grind around while he lays there like a blow up doll. When girls do that, guys call them a "dead lay". Why let him get away with being a dead lay if you're not?! Grab his hands and hold them on your hips, and then grind into him a little … most guys will get the hint and start thrusting back. Then it's all just a matter of timing your bouncing, twisting or grinding to match his thrusting. Now he's doing at least half the work, and you don't feel like you're standing naked on stage while he watches!

After all that, if you're still not really comfortable, you can always switch things up a little. Instead of kneeling over him, you could try getting up on one foot and one knee, so you're kind of crouching (might be easier on the knees!). You could lean forward and kiss him for a minute, while you do some of that slow hip rolling you mentioned. Or, instead of him laying flat on his back the whole time, you could ask him to sit up too, so you're kind of sitting in his lap (if he crosses his legs, and you wrap your legs around behind his back, it can be seriously fantastic).

Most of all, try not to put so much pressure on yourself. Sometime when you're alone, try fantasizing about what being on top would be like if you were super confident and having a great time… then try doing some of the things you imagine. And I really hope some of this helps out!

Much thanks to Carnivalesq and Heiko for their assistance on this one!