To me, it all depends based on the 24 years you've spent effort (assuming) on staying virgin. My wife and I "stayed virgin" until we were engaged (by virgin I mean only penetration, pretty much did plenty of everything else). Once we did we both very much felt silly for holding out like that, because now 13 years later it wouldn't have mattered at all if we screwed on the first date or not. Beyond that, I don't think culture puts the emphasis on virginity that it used to. I mean, people don't forever save the first bike they rode, putting it on a pedestal.

Don't fret about the "true love" side of it either. Odds are, whomever you start dating first, regardless of how much you love each other, won't be the person you stay with always. For example, you find someone, it's all perfect, you have your first sex. You even date long enough to get comfortable with each other and fulfill your fantasy. Then you find out he's a jerk or whatnot, and the relationship ends. Did that mean you lost your virginity with someone that doesn't love you?

Granted though, if you're saving it for your own reason, regardless of what anyone else thinks I wouldn't cast it away just solely for an experiment. Odds are the experiment will suck, because almost all first times suck. I know ours did, and we knew each others' minds and genitals inside and out from 6 years of dating. You didn't state the fantasy, but take it from me you'll be thinking "OMG OMG this is happening!" too much to pay attention to anything complicated.

If anything, spill the fantasy here, so we can better think it through from the outside in. :)

> But you knew that to fulfill it would mean having sex for the first time with someone who you knew didn't truly love you... Would you?

Ever hear of "FWB" {friends with benefits)? Does this sound like an arrangement the two of you could enter into? Because this other person is going to be party to this, ya better talk to her.

> Keep in mind, Im 24, a virgin, and have never had any sort of relationship that could really be called bf/gf.

Why haven't you been dating? An inquisitive mind wants to know.

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Would I? YES. Why do you ask?

A vrigin?? Whatever for?

Yes. In fact, I regret not having sex with the person I'm affectionately close with who was my bf at the time.

Honestly, there's nothing wrong with this.

What I'm curious about is just how "dark" this fantasy is.

I guess that it very much depends on your fantasy. If it involves hurting someone or puts you or your partner in danger then there is a good case for avoiding it.

You say "…with someone who you knew didn't truly love you." There is nothing wrong with "just a roll in the hay" as long as your partner is on that same wavelength. If, on the other hand, you are talking about paying for sex the issue becomes more complicated. Many "sex workers" are under coercion and your participation encourages that.