The Shortest Question with the Longest Implications

I got this question the other day on Twitter:

@MissLagsalot does size matter?

Well. That's a hell of a simple question. But the answer is so not simple. And hey, if you ask ME a question do you REALLY expect it to have anything like a short answer? If so, you're sadly misled.

The answer depends on so many things, but let's get it down to two basic parts:

1) The person you;re asking, and what that person wants. If you're asking me personally, my answer is yes. Size does matter because--assuming we're talking about the male sexual organ, which I think we, are based on the way you asked the question--the size of the member vastly changes the experience you have with it. There is just no way that engaging with a long, thick something is going to feel the same as engaging with a short, slim something. They're different experiences. Just like sitting through a three-hour movie is different from watching an hour-and-ten-minute movie. They're just not the same. So of course size matters in that way.

But that isn't to say that one is inherently superior to the other. Not by a long shot. Again, if you're asking me personally, I'm a very delicate person physically, so big isn't always best for me. I get sore very easily, I'm teeny tiny, and I'm generally not made for big things. They look ludicrously huge next to me and it's kind of silly. So while a big ol' salami size can be fun, it's a lot more of a process to get it to work with my fragile frame. Sometimes smaller can be easier to manage, and present less of a challenge to giving me pleasure over pain. For isntance, I once dated a very "well-endowed" man, and it took me a full two months to even allow the thing near me when naked. I was terrified of it and what it might do to me if it were wielded incorrectly. In the meantime, he was good enough to learn how to please me orally, so that when we tried to get our down-belows together, I was more, shall we say, ready for it. Conversely, I've been with many guys who were more moderately sized and never had to go through the fearful phase, which was very nice indeed, and provided they were able to use their equipment to everyone's enjoyment, I had a great time with them.

And furthermore, as do many other people, I don't always find that the swizzle stick is the most important part of the experience. It's one of the items on the menu, but it certainly isn't always the main course. If you can use your hands and your mouth, sometimes the cock can be done without, or sampled as just part of the meal. So in that way, while the size makes a difference in the experience, it's just one of many variables that can add up to a good time. It's not the all-important ingredient that makes or breaks it.

As far as other people to whom you might put the question of size, I can't speak directly for them, but bear in mind that these answers are different for everyone. I know a woman who is so small and tight down below that she has serious trouble using tampons--her partner is on the small side, and thank goodness for that. She could never handle a bigger person.

But there are people who are built differently and who find bigger members suit them just fine, or in fact are all they're looking for. To each his or her or their own... cock. Impromptu rhyme: "Whether it's flesh or silicone, rubber or plastic/use what you like and you'll feel fantastic!"

....anyway. There are people who don't get sore easily, and for whom the phallus is the centerpiece of any sexual outing. There are others who are grossed out by phalluses and won't even touch them. It's a big world out there, and all sizes have a niche that works for them if they're willing to figure out which one that is. And personal preference is what it is--you can work with it, work against it, and try to change it, but it is what it is. People who like 'em big have their reasons, and vice versa.

2) The person whose "size" is under consideration is also a very important piece of how to answer this question in any particular situation. What does this person want from a partner? What does this person want for him/her/themselves? The truth is that for people who are smaller, wanting to be bigger is just not going to work out. Coveting a huge porno cock won't get anybody anywhere, because A) most guys who do porn are NOT normal. They do porn for many reasons, but one of those reasons is that big dicks sell more porn, so porn dudes have massive members that are way, way, way above average and would be really uncomfortable for your average woman to handle. That's why porn stars get paid to deal with them. And B) those pills they advertise online... they don't work. You've got what you've got, and wanting it to get bigger just won't help anything. So who's asking the question, and why? If they're curious as to how to use what they've got to please their partners, then that's utterly doable no matter what the dimensions of your diddler. It's all about knowing your own body and being communicative with the person or people you're using it with. Finding out what your partner wants and learning how to do it will always, always get you farther than just having a big battering ram and bashing away at it. 
Big dicks might give some people more instant gratification (if those people are built for larger logs), but instant isn't always the best kind, now is it? It's fun for those who like it, but I find that a lot of people--and women make up a large percentage of those people--are much more satisfied by a longer, slower buildup that isn't the result of merciless pounding by big boners, but rather the end climax of a long, drawn-out session with skilled and creative lover. In a way, I sometimes think that guys with large logs can actually get short-changed by their massive manhood. It's easy to get a loud verbal reaction out of a partner if you're stabbing them with a sizeable salami (sorry, the alliteration is just too easy to resist), but that shriek might be one of pain or overwhelming confusion about their insides being scrambled. A really good, really powerful orgasm can come after hours of foreplay, teasing, coaxing, and refined technique that people with massive schlongs might never feel they need to learn. But if they did, they'd be well served by their new skill set. So again, depends on the person whose size is being examined and what it is they want to get out of it.

So, here's the short answer to your question about whether size matters: it all depends who's asking, and who that person is asking. It's all relative, even rods.