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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!

Q: I really enjoy my boyfriend, and we usually have a good time in bed. However, he's really *ahem* long, and I'm really not.

We've tried different positions to alleviate his being too long, but what would really help if there was a sex ring that we could put on his cock during sex to "take up some space" so he wouldn't have to concentrate on going to deep and hurting me.

Is there such a thing?
-Shorty

Not to worry, Shorty. :-) You can indeed get a stretchable cock ring, and have him wear it just around the base of his shaft (rather than around both penis and scrotum, like usual). If you pick out an extra wide cock ring, it should help "take up space" just fine … and if that ring doesn't do the trick, here's a 2 inch wide cock ring that might work even better.

Of course, depending on how hard he's thrusting it's possible that those rings, when stretched around him, won't be thick enough to stop penetration, so I was looking around for something thicker that could serve the same purpose. I found an adjustable cushion and strap set designed to be used with a penis enlargement gadget. Magnum Comfort Cushions look like they'd work perfectly! They're quite thick, and fit over an included adjustable strap.

Good luck, Shorty! :-)

threesomes…how? it just doesn't make sense to me.

Goodness, I wish you'd been more specific! So, I'll assume you're asking how a threesome (or ménage à trois) works physically. Considering you can have three women, three men, two men and a woman or two women and a man, the positions possible in all four combinations are … well, very very numerous.

I'll just try to do a basic, vague rundown of different ways a threesome could work … let's assume that any same sex participants are either bi or gay, and that strap-ons and other toys are acceptable to everyone involved …

• The participants can take turns having one-on-one sex, while the third person watches
• If a woman is involved the other two participants can penetrate her simultaneously vaginally and anally (double penetration, or DP, is hugely popular in porn movies)
• Person A can penetrate person B anally or vaginally, while person B performs oral sex on person C.
• Person A can perform oral sex on person B, while person B performs oral sex on person C, and person C can perform oral sex on person A … is your head spinning yet?
• All three people can give each other hand jobs.
• Person A can penetrate person B while person B penetrates person C
• Two people can simultaneously perform oral sex on the third person, while giving each other a hand job …

… and the list goes on. Really, the possibilities are probably only limited by your imagination and everyone's level of open-mindedness. If you're curious, and you're in a relationship, you could mention the idea to your partner and see if s/he might be interested in trying a threesome with you. If you're single, and interested, personal ads (both in newspapers and online) often feature ads from couples seeking a third partner.

Unfortunately, Adam & Eve discontinued Nina Hartleys "how to" videos about threesomes, which would be more entertaining for someone who's just curious, but not really intent on trying a ménage à troi. But if you're actually interested in trying a three-way, Amazon carries a couple of highly rated books on how to start, manage and enjoy three-partner sexual encounters. Threesomes: How to Fulfill Your Favorite Fantasy, which concentrates mostly on two woman/one man threesomes, and The Threesome Handbook: A Practical Guide to SLEEPING WITH THREE. Both books are written by people with experience with menage-a-trois sex and three-way relationships.

Q: What are some standing-up sex positions? I am a girl, and my boyfriend is strong enough to lift me up for long amounts of time…but I need some options, here.

Well, first I wrote down all the standing positions I could think of, and then I went looking for other sources, to see if I missed anything. I was hoping there were more standing sex positions than I'd come up with, but human anatomy has its limitations, and it seems my imagination was equal or better than any of the reference sites I found.

I'm pretty sure any other positions would involve serious contortionism, but if you do come up with any others that work, please leave a comment on this post and share them!

Naturally, any of these positions that involve both parties standing (hands or feet) on the ground will have issues with your height relative to one another. No worries though … if you have a staircase handy, or a small footstool or step ladder, most height problems can be resolved pretty easily!

So, without further ado: Four standing sex positions, with variations:

1. "Evolved Dog" or, Rear-Entry Probably the most obvious and perhaps most common of the standing sex positions, this one has a lot of different names. I like "evolved dog," because it's just doggy style standing on two legs … *cymbal crash* … Anyhow, the idea is that the woman stands with her back to the man, bends over to some degree, and he enters her from behind. Also works great for anal penetration.

   Variations: Put one leg up on a stair step, or stool, or chair, to change the angle of penetration. Lean over a counter top or kitchen appliance … or whatever else is handy. Lean against the wall. Don't lean on anything, and have the rear partner hold your hips, then reach back and hold his wrists.

2. "Tango" or, Face-to-Face, supported The basic position here is a couple standing facing each other, the woman's arms around the man's shoulders/torso, with one of the woman's legs raised, to facilitate penetration. Great for couples who want to hug and kiss during sex … or listen to tango music.

   Variations: The man can stand in front of a chair or ladder, so the woman can support her leg by resting her foot on it. The man can lift the woman's leg for her, by hooking his arm under the crook of her knee (generally also resting his hand on her buttocks … or could be manually stimulating her anus). The woman could stand with her back to the wall, bend her leg sharply, and brace her foot on the wall. The woman could stand on a stair step or small platform, and wrap her leg behind the man's leg (since raising the leg wouldn't be necessary).

3. "Carrier" or, Face-to-Face, suspended This is probably the group of positions you were thinking of when you mentioned the fact your boyfriend could hold you up. The basic position is facing each other, with the woman's arms around the man's shoulders, and her legs around his waist. The man helps support the woman with his hands under her buttocks.

   Variations: Resting the woman's back against a wall can help support her weight. If the man stands in front of a wall, the woman can brace her feet on the wall to help with thrusting. The man can hook his elbows under the woman's knees to change the angle of penetration. If the man's arms start getting tired, he can move to where the woman can sit on a counter-top or table, while he remains standing. Flexible women might be able to rest their legs on their partner's shoulders, for maximum penetration depth.

4. "Wheelbarrow" or, some kind of fucked-up handstand Remember the "wheelbarrow" game when you were a kid? One kid had their hands on the ground, and the other kid picked up their legs at the knees, like wheelbarrow handles, and walked them around on their arms. Fast forward (quite) a few years, take off your clothes, and get the person holding up your legs to take a step or two further forward, and you have the Wheelbarrow standing sex position. Your arms are in push-up position, and your man stands behind you, holding you up by the hips, while you wrap your legs around his lower back. Sort of a modified standing position, since he's the only one on his feet, but there you go.

   Variations: The woman could rest her elbows on a bed, couch, etc. The man could kneel on the bed, with the woman on the floor in front of him. Both partners could move up onto the bed, with the man kneeling and the woman resting on her elbows, or laying on her chest. The woman could lay on her back, resting on her shoulders, on the bed, while the man stood next to the bed, holding up her hips.

Honorable Mention: Vertical 69 Just what it sounds like … the woman wraps her legs around the man's shoulders, and her arms around his hips. He holds her up by wrapping his arms around her waist. They perform oral sex on each other. Or at least they try to, for as long as the woman can hold on without blacking out or getting a serious headache.

Q: I just can't seem to get the girl-on-top position right…how would you go about doing it and not getting tired out?

I must admit, "female superior" has never been one of my favorite positions … but every so often, it has been really great. And there are some definite differences between "meh" and "mindblowing," technique-wise. Assuming you're starting from a kneeling position, here are a few tips for making things a little easier for yourself:

Have him sit up. If he's sitting up against the wall, or a pile of pillows, you can lean on him. Wrap your arms around his shoulders, so you can use your upper body strength to keep your balance and lift yourself up.

Rock back and forth. You don't have to bounce up and down the whole time … try sliding your hips back and forth, or side to side, or whichever direction you like, while letting most of your weight rest on his hips. It'll give your knees and thigh muscles a break.

Rest on your hands. Bend forward and put the palms of your hands on his chest, or on either side of his body, and hold yourself up that way for a while. (Or lean back and rest your hands on his legs …) This works really well in conjunction with the "sliding your hips back and forth" maneuver.

Hold hands. Grab hold of his hands, palm to palm, and hold them up in front of you … then lean on them a little, or pull against them to make lifting yourself up a little easier. So long as he doesn't go spaghetti-arms on you, this can be surprisingly helpful.

Get him to do some of the work! Really now, when he's on top, you don't just lay there like a blow-up doll, do you? I'm rather surprised how many men do just lay there like lumps while the woman's on top. Try putting his hands on your hips, and see if he's not suddenly inspired to help out a little more. Once he gets his hips moving a little, you can sync yourself to his movements, and use him like a springboard. ;-) (Works even better if he gets a little lifting action going with his hands.)