I came across your site a couple months ago, and I’ve been a pretty big
fan since. I’m 18 and a freshman in college in North Carolina. I have a
dilemma, and I figured I would copy the entry I wrote about it in my blog
and send it to you. I don’t know who to talk to about this, but I would
like feedback from someone who doesn’t know me personally.

“Crossroads. And that’s an understatement.”

So…I never thought I would be so speechless.

But I am.

Utterly…speechless.

So I figured I knew him, and that there weren’t any more curve balls he
could throw me. I mean, he’s my best guy friend and we’ve already done
the whole “relationship attempt” thing, so I figured, what’s left for
us to worry about?

Holy hell, did I figure wrong.

So last night, we were talking…nothing out of the ordinary, really.
Lately, we’ve been fairly open with each other in talking about things
related to sex. I know what you’re thinking, but believe me, we’ve been
mature in our talks. It’s been honest question and answer kind of
things devoid of any lude or crude comments. Seems far-fetched, but
somehow, we made it work.

So he’s been talking lately of recurring thoughts he’s had about
wanting to understand women and their arousal and how we “deal with it”
and such. I’ve learned not to jump to any conclusions with this boy for
fear of falling flat on my face, so I didn’t make any insinuations from
it. Well of course the one time I don’t, he means for me to.

See, this whole situation is so surreal to me that I don’t know how to
write it out. Basically, I’ve been…um…”propositioned.” He wants me,
as his closest female friend who he trusts more than almost anyone
else, to help him come to understand the female body and its
complexities. He means this purely as an “educational endevour.” I
don’t think he’s actually looking for intimacy or a relationship.
That’s one conclusion I refuse to jump to anymore, ‘cause the bruises
from falling on my face the first time haven’t healed yet.

So where’s the choice in all this, you might ask? Why am I even
considering what seems to be such an immoral and
promiscuous choice to make?

Well you didn’t hear how he set this up. This wasn’t just a random idea
he thought of as a way to get some “action.” He honestly thought about
this for a good while, and came up with a number of reasons why he
thought it wouldn’t work. But his ultimate reason for asking me, he
told me, was that until he asked, he would never know how I feel about
the idea.

He was also honest in that he didn’t want this to happen if he thought
for an instant that it would compromise our friendship. In fact, that
was a large part of why he never brought it up. He values our
friendship so much, as do I, that he didn’t want to risk it for
anything.

He told me straight up that he would respect whatever decision I make.
And the thing is, I know that he means that. He’s such a security
blanket kind of friend that I know that if I chose to go through with
this, he would totally respect all of my feelings and take the utmost
care in everything he would do. Knowing that, it makes me look at this
situation from a different perspective. It makes me realize that should
I choose to do this, I would be in good hands. Trustworthy hands. Who,
given the chance, wouldn’t want their first intimate experiences to be
with someone they know and trust?

Now, though I hate this part, I want to make it absolutely clear that
he isn’t wanting to have sex. He’s not asking me to “do him,” or
anything of that sort. He wants to gain knowledge about women. If you
can’t get the point that I’m trying to make here, I really don’t know
how to say this any differently to you. He wants to gain experience in
how to please a woman.

So now I’m stuck at this crossroads. I don’t really know who to talk to
about this, because I’m mainly afraid that it’s a situation only he and
I can comprehend. Because no one else can really understand this, I
don’t really want to bring it up because I don’t want my friends to
look at me differently. I’ve never been faced with a decision remotely
close to this, and I’m not about to decide rashly.

So given all of the facts, you tell me. What would you do? Don’t decide
rashly. Think on it, and really put yourself in my shoes.

Because right now I’m standing at that crossroads, and I’m being pulled
both directions. I’m lost, and I’m afraid there aren’t many maps out
there for this one.
~~~~~~~~

So there you have it. I feel confused and lost, and I don’t know who
to talk to about this. Any thoughts? I would appreciate any feedback
right now.

Thanks for taking the time to read this. I appreciate it more than you
know.