Agreed, but in a way that doesn't lead to a conclusion or even decision. "You know, it's sometimes tough being best friends with you. In a different situation I'd be asking you out. Do you ever feel that way?" might be a good opener.

I have an online friend (no, not that kind) which whom I can discuss how wide-rantingly amazing people are, and that includes sexuality. We keep saying we're gonna write a porn epic together along the lines you describe - everyone's nekkid, greased up, happy, and finding new ways to get even happier - but keep saying…

Agreed, but the ending was so sentimental - almost shockingly so - that it kept it from being straight-up Literotica for hundreds of pages. I'm a sucker for writers with straight-up chops, which Baker has in spades, and that helped me, too.

I guess if the one on top is shorter, so the geometry works out… I'm trying to think. Maybe I need to be more flexible. Receiving a hand job whilst eating ass is nice. Kind of piquant mix of raunchy and cuddly.

That's gotta be a challenging one. I've dated women who admitted to a liking for that ,and also for rape fantasy. The two are not related, I know, except that both go so heavily against what we Nice Considerate Guys have been raised to think that I just can't engage in either. Totally great if it's someone's thing,…

(Checks cost of airfare to Seoul)

Hands are so under appreciated. So many nerve endings, so much control and flexibility. This is kind of corny but if my partner and I both reach down to touch fingers, the sensation of bodies in motion, connected, with fingertips touching, is really nice.

You've got to be a physical perfect match, or have necks like giraffes, no? I will say the surprise of a mutual digital rectal exam 69 was a fun surprise.

Testify. Not to sound like a Puritan, but why is porn/erotica usually Cheerful Happy People Doing Things I Already Do, or Scary Angry People Doing Hot Stuff?

Yeah, but they'll put you through three rounds of phone interviews, and in the end you have to sleep with the recruiter.

My dear Sir:

Have you had sex while camping? Tent sex is a nice way of adding some daring while still being quite covered up. Then you try with the tent unzipped, then move up to "on the edge of the pond" and "just off the Appalachian Trail" (fun but maybe that was a little risky, legally.)

Weirdly, Missus Rickster and I had really great sex when she was Great With Child. I think there is something very primal about the creation of new life that plays a part. Obviously if it's the bedridden, morning sickness kind of pregnancy the hawt is lessened.

You might enjoy The Fermata by Nicholson Baker. The premise is a variation of your fantasy, and it's really well-written literature, with a surprising amount of heart.
And loads of kink.

I like to cut Dan a lot of slack, but I agree that reply was not up to par. He clearly is young and trying to identify just what his wants are. Bi-curious, darned right. But a guy can be straight and enjoy having his bum filled, and it seems to me he wanted that physical sensation, not to be a with a man. There is a…

Yeah, I have to file him under Things I'm Told I Should Like But Don't. Right between Wilco and anal sex.

I expect to know if a celebrity is MY bed!

Miller: "John Wayne was a f**."

In my experience, most people like having a stranger say something positive. We're usually so beaten down from work or such. But I'm in the south, and pretty social, so my compass may be askew.

That's a tough but well-put question. Punk (and others) have great answers below, and I'll just add a little that may help.