The "When" and "How" Question

With hormones raging and the constant curiosity about what sex is like, I often ask myself the infamous question: when and how will I lose my virginity?

And so my imagination begins to wander: The lights are dim. Candles are lit. We look at each other embarrassingly as the moment to slip on that condom becomes increasingly awkward. Finally, it is securely wrapped around his penis and we get in the old fashioned missionary position. He pokes and prods in my area for a while until his missile finally finds my target. The initial entrance is one of struggle and slight pain, but we adjust the motions accordingly until the discomfort ebbs away and off we go!

My requirements for this ideal situation goes as follows:
1) Also a virgin
2) Someone I love

As I evaluate my (short) list, I have come to the realization that I have the mindset and standards of a 14-16 year old. In fact, being 20 going on 21, it's becoming virtually impossible to find fellow virgins within my age range to copulate with. In fact, a slight double standard sets in, and I'll actually think something is wrong with you if you're a guy over 20 who has yet to lose your virginity.

Yes, none of this seems to make much common sense, but the truth is my list is starting to look a little more like this:
1) Someone I love
2) Good looking

I at least want to be able to look back and recall that my first time was with an incredibly handsome, lean, cut, and well endowed young man. Although I've eliminated the virgin requirement in order to keep up with the times, I'd like to avoid the stigma of being "just another number," particularly if that number extends beyond 1 or 2.

But ultimately, it comes down to one requirement that I am willing to overlook anything else for:
1) I will not regret it

It seems that the only guarantee this will happen is if I wait for marriage. And well, let's be honest here, I don't intend on marrying anyone anytime soon and waiting to have sex when I'm near or past my thirties just REALLY seems impractical (and loserish). So ultimately, I have come to the realization that my one and only requirement is something that cannot be fulfilled. I think underneath it all, I already knew this subconsciously, which is probably one of the reasons why I've held back, especially for so long now.

And so I wait for the inevitable day where I just get sick of waiting and just start fucking.

It's the broken dream of a girl.

Pouty Lips

Sometimes the first thing you notice on the opposite sex is their eyes. Occasionally it's something else, say breasts. Or an ass. Recently, I've discovered my infatuation: pouty lips.

I don't mean the Angelina Jolie type, but the ones that protrude ever so slightly to form the shape of something I'd devour in a second.

Case A: Elijah Wood

Albeit the fact that he is a hobbit and a little grungy and bloodied up here, those are the lips. Yum.

Case B: Matsuyama Kenichi

Japanese actor I stumbled upon that really kicked off this infatuation. He's got the lips and really fucking knows how to use them too.

Can I get a hallelujah?