Quote:
You can do it.
Just make sure she's not batshit crazy. Then if you have a little tact you're all good.
This.
Also OP, I love how the story is about you talking about SEX...... at WORK...... to your BOSS and in front of your FEMALE COWORKER..... yet now we're talking about what's PROFESSIONAL. Lol. Now, if she had gone to HR and said she felt uncomfortable she'd be in the right. If your workplace is this chill that you can do that, you probably have nothing to worry about it. If you really are concerned about being professional and not losing your job, keep those conversations out of the workplace.
Now, that hypocrisy out of the way....if you sleep with a chick at work and dump her, she's not going to go to HR and say "Steve was fucking me...fire him." She can't, plus girls are smart and not going to mess their own shit up. If your workplace has a policy against dating coworkers, then don't. If you plan to fuck over this woman, then don't. Even so, you could get with this woman, abuse her, dump her, and most likely she still wont go to managers about that shit because most women prefer to avoid conflict.
There can be awkwardness if things end, and thats up to you if you can live with that. But for me, personally, I don't care. There's awkwardness when I date the bartender at my favorite bar for a few months and I see her there every time I go. There's awkwardness when I see an ex out. There's awkwardness when I ask the drive thru chicks out and I go to McDonalds for breakfast and see them again. I've banged many chicks at work, and see them almost every day...it's not awkward because I never led them on or acted lovey dovey when I wasn't. Also, I don't know about you guys, but I'm active in my career, as are the women at work. In a year, I may not be in the same department and probably promoted again. I may move to a better position oustide the company. She may get promoted. She may go back to school. I really dont care about the awkwardness because its not like I'm going to around the same woman for 2 years anyway at a company.
Anyways, if your workplace is so lax that you can talk about sex like that to your boss, and have a coworker near orgasm...relax. And if it's not that laid back, then don't have that conversation again. I can say, I WON'T have had that conversation with my boss in the open, and if I did in earshot of a female, he'd probably tell me wtf I was doing talking about sex in a female coworker's vicinity.