Horny co-worker as my first at 29?

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Feel free to move to Adult Discussion if need be: Hello, my fellow Planeteers. In the past, I know I've sadposted like a lot of guys that are the bane of L+D's existence, asking for practical advice as a guy with very little dating practice. 6 months into trying my second stint online (OKCupid alone this time, but thinking of Plenty of Fish and a pay site too to expand options, prob Match.com or Zoosk), I've yet to see the one woman who's kept in touch consistently, though she made it clear when her course for work ends.

Meanwhile, as I try and access other "busy" people I meet through the site, an odd situation with a co-worker (who no longer works close to my cubicle because they're organizing people by shift and she works earlier) has emerged. We've had nice small talk about her dog though like everybody else at work, they're friendly at the job and don't hang out with me outside of it like some do with each other. Anyway, I comforted her like other work friends last night as she was sharing on Facebook one of her occasional anxiety/depression episodes, a challenge with her couple kids and the madhouse call center I work at. She thanked me and said my response (basically "I've been through similar," [actually had to see the psych about meds after a weird episode at work and at home talking with my harried Mom trying to work her own job] "message if you want," etc.) "meant a lot to her," and several others liked the post so clearly I'm not seen as out of place in making it.

Meanwhile, she whines on other public posts (weird individual but who am I to judge) about not having had sex in 6 months. She's done it several times, a little too much for the joke to not wear thin if it's that and a sign it's not getting her booty calls to solve the issue. She's not unattractive and occasionally discusses dates she's been on with others (not me, which would be either mean or a sign of seeing me as a brother friend zone type), so I'd have to assume it's business and her own mental issues. I'm on the spectrum and not the kind of guy that can get away with innuendoes, so I haven't responded in any way, but if she were to have a moment of weakness and proposition me at least for a date, I'm mulling over what I would do. On the one hand, it would be a good confidence boost to lose it for free to a woman whose sheer desperation could lead her to come before I do (unless I have really good self-control and can avoid the usual premature ejaculation from the shock) or maybe want more rounds (hopefully not more than I can handle LOL). On the other hand, there's all the worries of the context making it awkward and leading her to have second thoughts about "just getting it over with" and all the worries of what I could be accused of thus for taking advantage of her in her hour of need, to say nothing of the issues with seeing each other at work if we don't get along well enough to be friends with benefits, something I would kind of suspect simply because I don't even have really close friends as far as I can tell without benefits, of either gender (I'm hetero male). Really unlikely in any event, but is it a bad idea or a good one if she's game?

It's hard to say much not knowing her. In regard to what I quoted, I would say that judging can be good. I've rationalized bad behavior some others many times, and it only hurt me. Is she really worth the time? Others will come along.

Question to ask yourself:

If you did "hook up" with her, given that you work together, and your relationship "went south" and there was strife between you, how would you feel about it? Only you can answer that.

If you desire to throw caution to the wind, innuendo or an overt pass at someone in the workplace is now verboten. This may be Seinfeldian, but here's how I would play it if I was in your position (virgin and 29):

If I had a pleasant one on one conversation with her and the topic turned to dating, I'd say something innocently with perhaps just a hint of self deprecation: "I'm not one to ask in that department, I'm afraid, since I haven't had much luck, (shrugs shoulders). I guess being 29 and a virgin speaks for itself."

A seed is planted. She may find the thought of being your first intriguing. If she spreads the fact that you're a virgin around the office, she would rightly be viewed as betraying something very personal you shared with her in confidence.

You're obviously WAY ahead of yourself with thinking about specific details and outcomes about a sexual encounter that may never happen. No harm though, I understand. I'd try not to think about that too much. Even if you did ejaculate "prematurely", you're still fairly young; that and your probable hyper-arousal at the newness of your experience would most likely result in your refractory period (time between ejaculation and your next possible erection) being very short. With younger males overwhelmed hormonally, (ie teenagers, early twenties), the refractory period can be nearly nonexistent and repeatedly so with a sexual encounter ending instead from soreness and or fatigue. It's not until you get older and your hormone level significantly lowered, where physiology dictates that your refractory period can increase to the point where you have "one shot" and that's all she wrote. I wouldn't worry about that either at your age.

Good luck.

So did you do it or where you just thinking about doing it?

Just thinking about doing it. She doesn't contact me independently, like everyone else there, so it's probably unlikely to happen. Got to go on with my life as is anyway.