24 year old virgin male: lose virginity to cougar?

So here is the situation: I am a 24 year old white male. I am tall, athletic/muscular, went to a good university and have a good job now. Overall I'd say I've done quite well in life and I've got my future sorted. There is however one thing that my life lacks: women. I didn't go on my first date until just a few months ago, got my first kiss there as well. And thats pretty much all I've done with a girl, kissing (not even really making out) and holding hands. The two girls I've dated (one of which lasted almost 2 months) both dumped me for the same reason: I lack confidence and experience and they didn't want to be the ones guiding me along, holding my hand as I learn the tricks of the trade. A lot of it was also due to my lack of knowledge of how to physically escalate. What this boils down to is that I need more experience and confidence with women in order to truly get a girlfriend (which is the end goal, not necessarily to screw around a lot, though I wouldn't say no to that either). I have been recommended one option by several sources and I am seriously considering it (whether I am able to materialize it is another matter, but lets assume I am for the sake of discussion): Find a more experienced woman, a "cougar" to show me the ropes a bit. Why? 1) Well firstly its every guy's fantasy to be with an attractive older woman but thats beside the point. 2) As I've been dumped because of my lack of experience so far, perhaps I can use her as training so that I would face less dumping in the future because of that. 3) Gain confidence and experience around a woman physically, know what to do in bed because assuming I am not an undercover sex god, the first few times will probably suck for the girl. I'd rather make the times that I am with a girl I really care for better. Counterpoints: Do I really want to lose my virginity to a woman I don't care about and will probably never see again? I don't know, I used to think of it being important who you had your first time with but I just don't care that much any more after years and years of absolutely no female action just pass me by. Sure, it would be nice if the first time was with a special girl but its not that big of a deal for me. Questions: 1) Has anyone used this approach, had their first time with a cougar? And if so, was it "helpful"? 2) Has losing your virginity given you more confidence around girls? 3) What do you think of losing your virginity to an experienced woman?

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