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!

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.

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.

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.)

Hmm. Well, I'd say the most important thing is to pay attention to your partner. It's pretty easy to get carried away with how things feel for you, and not always notice how she's reacting to what you're doing. While you may both still be having loads of fun, there's no substitute for knowing what she really enjoys, and there's no way to learn that without paying attention! Here's a few ideas:

• What kind of noises does she make when she gets close to orgasm? (Or does she get really quiet?) Listen when you change positions and see which ones seem to excite her most. It might also be a question of tempo; does she prefer it when you speed up or slow down? (You don't have to only do her most favorite things, but it's always good to know what they are so you can use them at the right time!)

• Is she forward enough to just tell you what she likes? If so, count yourself lucky! If she blurts out something like "Oh god yes, don't stop," you can safely take that as a hint.

• Read, read, read! There may be no substitute for hands-on experience, but book learning has its place too. A straightforward, well-researched book like "Our Bodies, Ourselves" will teach you a lot of solid fundamentals about female anatomy and sexual response. As much as sex is a matter of personal preference, knowing where nerve endings are particularly concentrated and having a good idea of what a lot of other women have to say about their own sexual experiences will give you a good idea of new things to try, and a better understanding of how it all works.

• If you talk about sex (and you should!), pay attention to how she reacts to different topics. She might be shy about saying no, but you'll definitely be able to tell if she's lukewarm about something. Go with the things that really interest her, don't push the things that don't, and you'll establish trust that may lead to more adventuresome activities in the future.

• Some women enjoy pornography or erotic literature, some don't. If she's open to that sort of thing, it's a great way to explore new ideas that interest you both. Again, just pay attention to what interests her most, and what seems to leave her cold.

There are very few things in life more fun than having a sex partner who's turned on by turning you on, and the more you can do to become that kind of partner for her, the more she's likely to do to return the favor.

Ooh, that's a tough one. I very much hate to frame any answer on this site according to "men" and "women" as general groups, because there is really no generalization you can make about either group that's going to be accurate across the board, except perhaps "both men and women have a large concentration of nerve endings in their genital areas." (Even an assertion as seemingly safe as "men have penises, women have vaginas" would raise some eyebrows in the transgender community.) That said, you asked, so I'll try to come up with a somewhat useful answer, and I do love making lists, so here goes …

1. Men Who Don't "Need" Directions … Some men I have met, who were numerically much more experienced than I was, had serious gaps in their understanding of women's sexual anatomy. A major pointer: The clitoris is outside the woman's vagina. Assuming you have no problem finding the vagina: If a woman is laying on her back, the clitoris is a rather obvious "bump" perhaps an inch above the vaginal opening. It is covered by a fold of skin, right where the inner labia join together. 3Dvulva.com has a nice diagram of the area.

2. Nice Girls Don't [insert sex act here] … Give blow jobs? Have anal sex? Enjoy sex in general? This is not a solely male misconception … sadly, a lot of women believe they either won't or shouldn't enjoy certain things, without having given themselves a chance to even try them first. Often times politically-minded "socially aware" men and women are as much at risk of this one as more stereotypically repressed religious folks. However, I have plenty of "nice" female friends who very much enjoy all sorts of sex acts. It can't hurt to ask, or suggest, something you'd like to try with your partner. (And if she leaves you for even suggesting it, well, perhaps she's not really the girl for you?)

3. Women Need Someone to Take Charge in the Bedroom … Well sure, some of us like that. Some of us don't. Some of us like that sometimes, and not other times. And some of us might like it very much, but only from men who don't go around making ridiculous overly-dominant assumptions about it beforehand. Not every girl wants to be swept off her feet and carried to Prince Charming's castle. Some of us would just as soon follow on our own horse, in case we decide we'd like to leave afterward. And we most assuredly do NOT "just need the right man to show us our place."

4. Women are naturally monogamous … This assumption is often backed up by a pseudo-scientific speech about cavemen, and how men "need" to spread their genetic material as far and wide as possible, while a woman will naturally try to attract and "keep" one man who can support and protect her and her offspring. This is crap. I personally like to think of monogamy as being a variable, individual thing, rather like the popular conception of hetero- and homo-sexuality being two points at opposite ends of a continuum of sexual preference. There are people (both men and women) who are like swans: pair bonded until death do they part. There are people (both men and women) who are like bonobos: Anything goes with anyone you like, whenever, where-ever, whatever. There are people who like one partner at a time, but not for very long. And people who like multiple partners as a "bonus" sort of thing to enjoy with their primary partner … and so on, and so forth.

5. If You "Keep it Up" Long Enough She Will Come … No, she very well may not. A woman not having an orgasm does not necessarily mean you're not big enough, or didn't last long enough. It may very well mean you need to go up and revisit item #1 on this list, and develop your technique beyond "in and out and in and out" though… I once knew a woman who claimed to have dozens of orgasms every time she had sex. I thought perhaps she didn't know what an orgasm was (or maybe that her boyfriend was Superman), until I talked to one of her former partners, who verified that she did indeed "seem like she had an orgasm every minute or so." So yes, some women are lucky enough to be able to orgasm from their partner's pelvic thrusting alone, but it's generally not the norm. My advice? Skip the Viagra and get creative.

As this question appears on pretty much every sex Q&A column I've ever read, it seems fitting it would be our first query here at Things You Can't Ask Mom. And the answer is, yes, it absolutely does. Of course it does! Men come in all different sizes, right? Well, newsflash folks: so do women. I fail to see where anyone gets off saying "no, size doesn't matter" … unless they're just not very experienced, or they have the vaginal muscle control of an advanced tantric master.

Yes, almost any woman can both give birth and keep a tampon in place inside her vagina, amazingly elastic, versatile things that they are. However, childbirth is not something most women would choose to do recreationally, and tampons are so small as to become unnoticeable to most women within a few seconds after insertion … neither of these extremes is something you want your penis compared to, I'd think.

But here's the deal: there is a great deal of latitude in the size range within which a penis will be perfectly capable of satisfying most women. Bigger is NOT always better. While I do I know one woman who dated a man with a 12" cock and said it was the most wonderful thing she'd ever had, that very same man, years later, dated another female acquaintance, and was physically unable to penetrate her more than half way. I have personally been with men with whom certain otherwise favorite positions were tragically off limits because it felt like they were trying to play billiards with my ovaries: not pleasant at all. Then there are some women who enjoy having their cervix bumped during sex, and other women who are so sensitive they'd rather be with a man who can't penetrate them fully.

In a way, men on the smaller end of the scale are actually the luckier ones. Even a very small man with an open minded partner might find that a combination of toys, anal sex and creative positions more than makes up for less-than-earth-shaking vaginal penetration. In my own experience, a smaller partner can accomplish great things with a combination of stamina and mutual flexibility! (Maybe someone should start couples yoga classes especially for 'petite' men and their partners?) A man who's partner can't fully accommodate him, on the other hand, is pretty much either stuck with never being able to stick it all the way in, or with finding another woman.

So, in short, yes. Size matters. But different sizes matter differently to different women, for different reasons. Looking at my ruler right now, I'm estimating a good 4" range between the lower and upper end of men who had no particular problem getting me off … the lower end involved a bit more acrobatics, and the upper end had to forgo doggie-style, but that still leaves a lot to be done in both cases. I'm wagering the vast majority of men aren't going to have much problem finding a woman who's personal size preferences are a perfect match.