So My 40+ yr old married boss wants it, and Im 24, how to proceed?

[Benwin]

So, my boss is over an entire region of my company. I went out with her last week and flirted a bit, then she started passing me notes, the conversation quickly escalated to include sexual innuendo. I did not know if she was just playing around then so I decide to retest the waters and go a little further. So, I did so, and she is hella open to my advances. She is into martial arts and has that "up for anything" you only live once mentality, which is cool. I cleverly brought my digital camera to the bar we went to and pre-uploaded a bunch of pictures with me taking photos with hot girls from the past. Worked like a charm when she asked to look at the pictures I took of her, gotta love social proof. So, she's like you're so popular, you can have any girl you want. Why me? I proceeded to tell her how she was mature, intriguing and a kindred spirit and I never met anyone like her, dadada. She is buying it hardcore. After the bar, I called her, as we were driving off in the same direction. She seems to be really paranoid about my advances, thinking someone else put me up to trying to **** her. She's like i could get so fired, what if someone finds out, ive been here for 20+ years. Then she says music to my ears, "Well, I guess I'll have to get over it" meaning she is definitely open to ****ing around. This happened Wed night, but today at work, a lady that had worked in the same office for years, suddenly died, so I dont know how much time if any I should give her. She didnt seem really affected by her death, she was just her boss, never really did anything outside of work with her. How soon is appropriate for me to restart the advances? Should I suggest a hotel since we both live with others, her with her husband and kids and me with the 'rents.

 

[PoloBlue]

I would stay away from her, since she has a husband and kids, your asking for trouble.

 

[Helter Skelter]

If your both going to the funeral for this employee make arrangements to see her afterwards at your place.

Bang her there.

Funerals can bring out emotional and physical longings.

 

[NewMan]

I hope you don't value your job.


So, keep doing what your doing. It will figure itself out.

 

[ShortTimer]

Originally posted by PoloBlue
I would stay away from her, since she has a husband and kids, your asking for trouble.

If that doesn't make your **** go limp how about this one:

husband + shotgun = you dead foo!

 

[Desdinova]

Don't stick your d1nk in the company ink.

 

[Benwin]

heh, but its so taboo its intriguing!

 

[Benwin]

Originally posted by NewMan
I hope you don't value your job.


So, keep doing what your doing. It will figure itself out.

actually the job is fairly temporary, not a huge deal. They need me more than I need them and they dont pay me enough, might as well get something from it.

 

[Juggernaut82]

yup

 

[Rob]

Walden said it best: "if you want the pizza, eat the pizza!"

 

[Alpine]

Ok, fvck her and when she sacks you when you call it off, claim the unfair dismissal compo, or does it not work like that the other way round?

 

[Ricky]

This sounds exactly like a situation I got in even the ages are similar. The woman made advances toward me, which regrettably after alot of thought I took action on.

It is the worst thing you could ever do to sleep with a married woman. I strongly advise you avoid her. Women her age will do everything they can to sleep with you once they've justified it as being OK in their mind.

 

[Benwin]

im the agressor, she was all worried, but im slowly but surely re-assuring her. it was funny, i just got back from the office, apparently her husband and kids are supposed to visit her and we are talking about the groundwork of an affair and she's like "omg did you lock the door" and she assured me after this next target is met in like a week, we will be able to have fun. By the time im done with her, ill have her eating outta my hand.

 

[SamePendo]

So, the lesson to be learned is:

To bang a MILF, you must get her to trust you, and make her see there is nothing wrong with banging you.

(I'm still preparing to do a thread about how to bang a MILF... takes time though.. learning through experience).

 

[Ricky]

I think the big thing is to just become friends with her. The reason the women went after me is that we were pretty good friends already and I also seriously had no thoughts about doing her until she brought it up. She knew that I was single and hadn't been dating for a month or two after a breakup of a relationship I was in. I had told her I was sexually frustrated, but when I told her that I didn't have any thought of her being the answer for it.

But she apparently did. She tried to seduce me one night when we all went out as friends. I was a bit surprised about it. I turned it down that night and a couple of other nights. Then finally I didn't turn it down again anymore.

We continued for over a year and a half. She was good, but the guilt was horrible. We finally got caught when I called her and the phone rang just enough times to go to the answering machine. She picked up the phone and our conversation was recorded. She was yelling at me because I wasn't seeing her as much anymore (This was what I feared, was that she was hooked on me and wanted something more like a real relationship and to leave her husband). She made a comment about how rude I was treating her for someone I've been having sex with for a year and a half.

After that the husband finally found out who I was. I was living with the parents so he told them all about it. Fortunately I was never around when he stopped by. Finally after a solid month of dodging him (I stayed with friends in another town), he got me on the phone at my work. We talked but I wouldn't admit to anything for fear of him recording it for a court trial.

I kept looking over my shoulder for several months. It was a horrible experience. One time about 6 months after it was found out, I noticed a car following me at some distance. I got a weird feeling about it. I started making some turns from where I was headed and the car followed. Finally it got close enough that I saw it was both of them.

They followed me around a mall and kept following me. I sped up but my car isn't all that fast. Finally I thought of going right to the police station. That kept him away. I was really scared.

The next day I thought seriously about buying a gun or something else.

That was the last I saw of them a few years ago.

TAKE MY ADVICE IT IS NEVER WORTH IT.

 

[Benwin]

ok guys, I need some advice. Things are gettin pretty thick. So the boss likes me and so does this co-worker's daughter. The co-worker's daughter keeps saying like "i heard you like someone else" and crap, i try playing it off. I am flirting with her and made plans with her to try and quell this discussion. Then she proceeds to tell me that her mom and my boss are best friends and they talk about everything together, including me. so now I dunno wtf to do. Confront my boss about it and break the co-workers's daughter's confidence to try and get her to keep her mouth sealed so I dont have to go after the daugher as a diversionary tactic. I am not sure what to do, but i did not want too many people to know. Now like 2 people know/are suspicious about my intentions toward the boss. Ahhh how the plot thickens....bah

 

[Sexy_Malibu]

I always say don't **** where you eat... and don't **** around with someone else's SO (especially when there are kids involved). It's also kind of ****ed up to make her risk her job which she actually cares about and has been at for 20 years, just because you don't give a **** about your own.

But you seem to not care, so whatever.

As for the young single co-worker vs. the older married boss... who do you want? You can't have both, so choose. I'd say choose the one your age, who's not married. Seems like common sense to me...


But if you're still wondering about the boss thing here's a little anecdotal advice from the infamous Tucker Max:

[background: he had the opportunity to sleep with a very important married/with kids female partner. He for some reason that even he can't figure out, passed it up. Then he did some stupid drunk antics at a charity auction... and then...]

Wednesday comes, and around 4:30 John Steele asks me to come to his office. I stroll up there and notice my key card, which you have to have to operate the elevators or doors, isn’t working. This means only one thing…

I get into his office, and he’s in there with some other lady I've never seen before. John introduces her, some HR lady, and then proceeds to tell me that I have an option to either voluntarily withdraw from the firm or get fired. He cited certain things I had done that led them to this course of action, like my “porn line” comment and some other stuff like that, but said nothing about the really bad stuff I did. If I withdraw, he tells me they will pay me a large separation sum, pay my rent for the summer, and pay the for the item I “won” at the charity auction. In total, this is close to $20,000, plus I get to keep what I’ve already made in the not quite four weeks I was there. If I get fired, I get nothing.

I’m a little bit in shock, but not really; one of the associates at the firm, who is no longer there, heard about this, and gave me a heads up the day before. I took the money, thanked them, and headed out. It all went rather pleasantly, considering.

Granted, I had acted a little reckless, but I was nonetheless confused. I figured I wasn't getting an offer, but I didn’t think I was going to get fired, and the reasons he gave me for them letting me go were bull****. They had plenty of reasons, don’t misunderstand, but the ones John named were not a reason to fire a summer associate.

The next day, I got two calls, both from associates at the firm. One talked to me on the phone, the other met me for lunch a few days later. They both thought I had been dealt with the wrong way, and independently found out what really happened behind the scenes, and both told me basically the same thing: I got canned mainly because of the Sally incident, and not because of the charity auction. The one who met me for lunch told me that he had talked to a “very important partner” in the firm, and he was told that, given my track record of outlandish behavior, the firm was scared I was going to eventually sleep with Sally, or even do something worse than that, which would make me either a huge liability (if I, say, got drunk and set the building on fire) or invincible (if I slept with Sally). Why would it make me invincible? Because if she slept with me, and they didn’t give me an offer, then they could be liable for a sexual harassment suit. Not that I would ever sue them if that happened, but considering my behavior that summer, I can understand why they viewed me as a liability.

To me, the most delicious irony is that, ultimately, because I didn’t sleep with Sally the firm was able to get me out. Can you believe that? Because I didn’t **** her, I ****ed myself.

For the whole story (and some laughs) go to: The true story behind "The Now Infamous Tucker Max Charity Auction Debacle" email
at Tuckermax.com

 

[Benwin]

Originally posted by Sexy_Malibu
I always say don't **** where you eat... and don't **** around with someone else's SO (especially when there are kids involved). It's also kind of ****ed up to make her risk her job which she actually cares about and has been at for 20 years, just because you don't give a **** about your own.

But you seem to not care, so whatever.

As for the young single co-worker vs. the older married boss... who do you want? You can't have both, so choose. I'd say choose the one your age, who's not married. Seems like common sense to me...


But if you're still wondering about the boss thing here's a little anecdotal advice from the infamous Tucker Max:

[background: he had the opportunity to sleep with a very important married/with kids female partner. He for some reason that even he can't figure out, passed it up. Then he did some stupid drunk antics at a charity auction... and then...]



For the whole story (and some laughs) go to: The true story behind "The Now Infamous Tucker Max Charity Auction Debacle" email
at Tuckermax.com

well, the boss is a lot more attractive than the young single co-worker and I know i could get her(single girl) easily, so there is no thrill or attraction there for me.

 

[Falcon Eye]

I call troll on this one

Originally posted by Benwin
ok guys, I need some advice. Things are gettin pretty thick. So the boss likes me and so does this co-worker's daughter. The co-worker's daughter keeps saying like "i heard you like someone else" and crap, i try playing it off. I am flirting with her and made plans with her to try and quell this discussion. Then she proceeds to tell me that her mom and my boss are best friends and they talk about everything together, including me. so now I dunno wtf to do. Confront my boss about it and break the co-workers's daughter's confidence to try and get her to keep her mouth sealed so I dont have to go after the daugher as a diversionary tactic. I am not sure what to do, but i did not want too many people to know. Now like 2 people know/are suspicious about my intentions toward the boss. Ahhh how the plot thickens....bah

Yep, you're forty year old married boss wants you, a 24 year old, to screw her brains out and talks about it with some one else. This someone else just happens to have a daughter that has the hots for you and her mother has passed on all this information that her "best friend" told her in confidence.

Sorry pal, the plot here has thickened to soap opera proportions. I no longer believe a word you're saying.

 

[Benwin]

dude, i have no reason to lie, this is the truth, the daughter is not that attractive. Shes actually kinda chunky, also, chicks become more attracted to you when they find out other chicks like you, now how is this so far fetched? Also, I rarely post here, 100+ posts over 3+ years. I really have time to come here and indulge in and perpetuate fantasies. I think not. Believe it or not, all of what I have said is true and I come here for genuine advice on my situation. Haven't you ever heard the phrase "Truth Is Stranger Than Fiction"? Well it holds true if you are exposed to enough.