Let's call my coworker who has the vagina 'Clarice.' As in the FBI agent from the film The Silence of the Lambs.

She is 22, I am 28. She has two really young kids (twins) by a baby daddy who sounds like a shady retard. They are not together. I just found out that she is kind of seeing a much older dude, but I'm not sure how serious that is.

Basically I just want to hump her vagina as stated in my title. This is not someone I'd like to date seriously, although a friendly hangout sesh a few times might be fun.

The problems I see involve leading her on that I want to be a provider for her and her kids or serious boyfriend guy, the potentially serious relationship with this older dude that I don't necessarily want to encroach upon, and the social ramifications of messy post-sexy times at work.

HERE ARE SOME DETAILS OF MY 'PROGRESS TO HIT THE PUSSY' THUS FAR::::::

I work for a small company cleaning houses. Daily routine is usually one-on-one with another employee driving from job to job with fairly minimal interaction during the cleaning times. I have worked with Clarice 4 times.

First time was my first day on the job and it was Clarice, another girl, and myself. No really memorable interactions. At one point I lied and said I was 'really nervous' even though I was not just to see what the reaction would be. Reaction was predictably unmemorable.

Second time was a lot of fun. We worked well together, flirted, had fun, hit it off and had good conversation the whole day long. Can't really remember a good example because I am kind of drunk and this was like three weeks ago.

Third day sucked. She was sick the whole day, kinda cranky, not much fun to talk to. I mostly just left her alone but expressed a bit of sympathy. Finally told her to go home and finished the last job by myself.

Fourth day was okay. I was in a kinda bad mood but we teased each other back and forth most of the day and had sort of fun together. At some points it seemed like the tension between us was more antagonistic than playful but at other times it seemed like she was giving me really warm, flirty smiles, signs, whatever. Also, with little context, she told me that several other employees said they really liked working with me. And then said that she was the exception. But it sounded like a joke.

Major down side was learning about her much older 'boyfriend' and her out of the blue saying she thought I was gay at first until she heard me talking about girls. I get this a lot, even from girls I have hooked up with (including exes). I guess it's a mannerism thing and I over-pronounce words and don't act like a bro very often and look sorta clean cut and wear my hair short and have anal sex publicly. Really I consider myself mostly straight with some gay interest but at the time it was easier just to say 'no' when Clarice asked.

At the end of the day, I asked her what she was doing and she said going to hang out with her mom and kids but maybe she'd see me later that evening when we returned to pick up paychecks. Think I got kind of a flirty smile there but hard to tell (drinking, memory)

Didn't see her but it's not like we agree on a time to meet up either.

So yeah!!!!!!!!!!!!!!!!!!!!!!!!!!!! HELP ME FUUUUUUUUUUUUUUUUUUUCK. Rip me to shreds, sexperts. Should I go for it? Wait to see if she maybe gets this job at a hospital so things aren't awkward at work post-coitus (most other employees are uptight Christians) or find out how serious her older man is or just go for it and throw caution to the wind????????

Been a little out of practice lately and any feedback would be appreciated.