(WARNING-Guys Thoughs! Do not stray into this dangerous and previously thought to be non-existent territory without consulting a psychologist (or your cat which gives much better answers anyhow).
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Does size matter? Yes. All things being equal in the talent and skills, yes. As someone once said so dearly 'you can't make butter with a toothpick!' and ladies, if you are too distracted by the oversized invader (or lack there-of) then yes, you are going to be too distracted to turn into a nicely quivering purring mass of butter. (Yet another odd analogy from an odd guy).
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(Warning #2, for those who have very limited amounts of self esteem, you may want to consult Fairy Godmother before reading. Wait, Shrek nuked her.. Well, talk to friends about this)
Secondly, the size thing goes BOTH WAYS!!! 
<GASP!> "You mean?" Yes ladies, that's correct. You girls come in sizes as well and I'm not talking about the height to width ratio or whether or not that wedding dress is going to fit you come vow day. I'm talking about the internal plumbing sizes and one size certainly does not fit all guys. I am not, shall we say, inexperianced nor do I think I fall into the player category (or I'd not be here getting married) but I have delt with the size issue on a few occasions. As such, here are some things I ran into:
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All girls are built differently and all girls have different angles. Yes, weird, but hey, everyone is unique, just like everyone else. Right? The angles have a lot to do with the depth of penetration a guy has in any given position (along with her basic figure). This apparently has nothing to do with the body-type as well. IE: Heavy or light, tall or short, the angles have a mind of their own.
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Every girl has a certain amount of depth to work with before you are trying to knock her cervix and anything else attached somewhere up past her tonsils. This is what I refer to the Ouch Point (more affectionately known as when she gets ready to grab you by the testicles and throw you out the 3rd floor...when you live in the basement) No guy I can think of would deliberately hit this point as it is the female equivalent to getting kicked in the nuts. Not fun. In fact, very, very, not fun. Back on the topic at hand. There are some girls who's depth is, shall we say, cavernous, and from what I gather most girls expect to be 'filled to capacity'. As such, Lady of the Caverns can be left feeling as though she has tackled an inadequate guy when the same guy could go to another girl and be bumping the cervix, getting thrown out the window, and having to look for his pants in the morning.
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There are also width/girth issues for ladies as well as guys. For instance, there was a post a few messages up where she referenced the guys head as being roughly the size of, say, a horse, while he had a stack of quarters to back it up. Or you could simply call it rose-shaped if you prefer to keep it all nice and clean. The lad has girth, but the girl may not. She may find the shaft lacking but the head is going to cause some problems. This is something I have actually never experianced so I'm going to let her explain (preferably in detail for our amusement) what she did to get around that. What I have experianced is that there are a few that just don't have the tightness/limited girth to get decent friction and thus the guy is left feeling either inadequate or (with the self defense mechanism) that she's huge or (less flattering) has a LOT of previous experiance. This effect can be compounded by the frequency of sex with the same person. If you are together a lot in a short period of time like virgins who discovered how much fun it can be or what have you, then the girth factor is going to change a bit as your body grows to accomodate this new play toy. Take a shrot time off and it tends to contract a bit. There is also the other end of the spectrum; the young lady who is essentially so tight that it can hurt both of you. (Having experianced this I highly recommend lots of foreplay, massage oils, Enigma in the background, and plenty of time. It's worth it!) This could be the female inversed equivalent of Bam (see your local adult toy supplier for a hands-on reference item).
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Options? Well, if the guy is huge I'd suggest the massage oil/serious foreplay/relax and work with it if you can route. If that fails and you are getting married suggest a 2nd or even 4th circumcision. You never know.. If he is small there is another route. (another warning, you may read something that could offend a skittish person from some small island in Tahiti). Try a cock-ring. Yes. There, I said it. Cock-ring. Not a wedding ring (that one can shrink the guy even further if you aren't careful), but a cock-ring. Depending on the ring construction (never start off with a metal one. EVER. Even I won't go near those) and the guys age/physiology, he can go up AND out anywhere from 10% to 35%! Yes, instant Big Boy, just add ring. How does this do this? it essentially puts pressure on the artery that allows the blood to flow back out while letting the vein that flows in to keep pumping. Hmm.. Pumping, appropriate word that.. well, anyhow, the ring has other side effects. Not only will he tend to be huge, it will also force his testicles to grow somewhat appropriately and pushes them forward. (Editors note: if you don't know what one is or how to use it, feel free to e-mail me. I was 32 when I figured it out!) The side effect of this is that they get to put pleasant pressures/tickles/teasing and generally rubbing on various parts that most girls find very very good. In fact, it's a fast way to turn a girl into the aforementioned puddling quivering toe-curling, back-arching.. well, you get the idea. <sigh> "This is great, Myk! But how do I sell it to him?" Ahh, there-in lies the rub. (no pun intended). It has a few side effects for him as well. Ego-wise, the first time he discovers what it's like to have an adult size he is going to be rather proud of it. In fact, be careful that he doesn't dash out to find a yard stick. Secondly, it seriously enhances the nerves and feeling as the skin is stretched an those all enjoyable nerves are now that much closer to you. The extra girth to go along with the sex means he has that much more pressure/friction. This can have the side effect that the first couple times it's such an intenstly purrrrrrrrfect feeling that he may not last long. Just so you know, it's not him failing, but that his body finds you that much more intensely satisfying. You will certainly feel a difference in each pulse, throb, or quiver it makes especially at orgasm. The word intense has been used and is among the more socially acceptable of the happy phrases that has been uttered as a result.
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The ring is also much better than the 'add an inch' toys mentioned above. Those are pretty detrimental to a guys self esteem and lord knows I can't imagine him buying one from anything short of mail-order. It also pretty much covers the main nerves that bring him to orgasm. This can be good if the guy is an instant milk kinda guy, but bad for most anything else.
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So to end my long-winded male point of view (limited to mine and occasionally the cats) and hopefully shed some light without intent to gross out, that's my take on the size issue. This is a very short take. For the long winded you can e-mail me via the link from my name. It get's weird from there. :)
Btw, for the female size issue: remember, you can give birth through there so we have to be big enough to at least be felt for it to be much fun for you. As for the skills a guy has, if you can't or won't talk to him and TELL him specifically what makes you happy, he won't know. Don't rely on an extra grunt or groan or whimper or scream to clue him in. He's male, remember? Actually, this would make an excellent thread on it's own. 
and didn't have much of a sex drive. Ask your friend if his name is Chris?...lol So I would ask myself if this is something I could live with . Well needless to say I lost interest in him anyway. So I didn't have to think about that anymore. He has got to satisfy her. Bottem line if he don't move on . 
