Jonny,
I have a different opinion to offer. First off, though, I absolutely agree. Do NOT make an SD / SB proposition! No way, uh-uh, not a chance, where you work.
However, unless you have shared with her that you may get into pay for play (and if you have, then, yes, that's exactly what she's hinting about, so don't cross that line at work,) she may very well be just flat out flirting. The simple fact is, if you have money, in a comfortable amount, girls in situations where they have young, handsome, deadbeat boyfriends will see you as a potential long term escape, knowing that it'll probably come to nothing. If you're not uncomfortable with a work affair, that's something I've engaged in (with all of the consequent risks, of course,) but trust that you're probably in a position where this girl knows you, is interested in you, and imagines what life would be like with someone who can actually bring home the bacon.
Understand, she's not going to leave her boyfriend, and, if she does, she could make trouble for you, especially if she knows your home address. You'd be in a position to judge whether or not she'd keep quiet. But there is nothing at all outdated about a "mistress" role, and if she's volunteering, you can certainly test the boundaries.
In cases where I've done "vanilla" dating with someone of a very different tax bracket, I have a couple of simple rules: if she flat out asks me for money, the answer is no, and I'm done, no second chances. (I don't tell them this rule. It's my "no, I'm not an ATM" rule.) However, if she's providing you the kind of satisfaction that you enjoy, and she's CLEARLY in a position where she's living paycheck to paycheck, sometimes you can make things a little easier, like "hey, I'm worried about your car. I don't want you getting stranded. Let's drop it off with my mechanic (NOT the one you use with you or your spouse's vehicles, of course,) and let them take a look at it, while we go get dinner. " The trick here is to NEVER let her feel like you're doing pay for play. That's not what a mistress wants, but they absolutely want to be spoiled. It kind of amounts to the same thing, but it will ruin things instantly if you cross the line and make her feel like a * Even if that's what she's fantasizing, while she's with you.
Again, though, if she knows you do pay for play, the above can be entirely ignored. It's only useful if you haven't shared that side of your life.
When I was married, I had several very nice arrangements with girls who would never have said they were SBs, but who were (mostly) attached, and who were happy to put out regularly for a guy who could show them a better time than they were getting at home, even with no actual money exchanged. One of them who wasn't attached got a little crazy (I set her and her kid up in a cheap apartment, brought by groceries once a week, and hung out, and she made PLENTY of private time for me, several times a week, but started wanting to do more than just "play" house so I had to leave.) She never broke my cover, even a few months after I broke up with her, when she rented a room in a house less than a block away from the one I was living in with my spouse, so if you're willing to take the risk, a mistress is pretty cost effective, and can be a lot of fun, for a while. My earliest one still touches base once or twice a year, but she's gotten a LOT less cute than back in the good old days, 20 years ago, but her thing was just that if you actually took her out on dates and got a hotel, she was always DTF, despite her badass harley riding boyfriend, who was usually out (probably scoring on his own.).
Bottom line: if she doesn't know the p4 p side, and if you don't think she'd bust you, and if you're willing to risk being wrong about that, the world has few enough cute 23 yo blondes who come chasing after us, and it's a shame to let a good dessert go to waste.
[QUOTE=JonnyRockett;3532347]There's a girl I've worked with for about 2 years. She's about 23, blonde and cute. Her face is about a 7 and her body is a solid 8 or 9. We've had many opportunities to work alone together and over the years we've shared some things that I know I wouldn't share with other coworkers.
Lately, she's been telling me about her financial problems. Her BF quit his job about a month ago and still isn't working, so with her paying all of the bills, money is tight. She said she's not behind on anything but she doesn't have any money for anything else. At first, she didn't add much to what she was saying but lately she's been calling me a "baller" and commenting that I have nice things and a nice car. I really don't but I guess from her perspective. And she keeps adding to the end of it "if you only knew". I do have an idea but I'm not 100% certain. It could be wishful thinking on my part.
My big head is telling me it's a really bad idea to start a SB / SD relationship with someone I work with but my little head is telling me to go for it. With both of us having an SO, neither of us could host and I just see things getting really complicated.
So, what do you guys think? Is this girl trying to start something or am I imagining things? If she is interested in an arrangement, should I stay away? If I go for it, I'm not even sure how to breach the subject with her.[/QUOTE]
