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how to play this situation.....?

Skel

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The situation...

I work with this milf, old enough to be a milf but not a mother. I call her a milf because shes older and i wanna bang her. Shes HOT too, about 40(im 26) and she works out so she has an incredible body.

Me and her have become friends working together for a few months and we have been talking. Shes always asking about todays dating scene/bare scene ETC because she hasnt gone out in a long time. I guess she thinks shes too old or unatractive or whatever. I told her that she wouldnt have a problem picking up a guy at a bar but she said shes been out of the loop for so long she wouldnt know what to do. I made her a deal. I told her i would go to a bar with her friday night and give her tips on how to get a guy to pick her up and basically be her moral support. I told her if I was unable to help her get a guy that night, that I would go home with her and be her one night stand for the night.

She laughed hysterically and then said " Ok, your on"

So here it is Wednesday, 2 days to go and I basically want to know how i can help her fail in her man hunt so I can fulfill my part of the bet, that is taking her home and banging the spit out of her. She is going to expect me to help her though, and I dont want to make it obvious that im setting her up to fail.

Any ideas?
 

DankNuggs

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She has no intention of picking up a guy......

You set this up perfectly...

There are a million reasons why she isn't going to pick up a guy infront of you......She has her one night stand taken care of....
 
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Walk this Way

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Yeah take her to the bar. And then start hitting on her. Not only do you manage do find her a guy that night, but you get to bang her too.
 

Don Juanabbe

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This one has dropped right in your lap. Always take advantage when opportunity knocks. Get her tipsy, go home with her and shag her rotten. She's 40, your 26, she'll love it, trust me.
 

squirrels

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That WAS a pretty smooth setup. Actually, a lot of guys (AFCs) will be chased away by the fact that she CAME there with YOU. Try to set her on the guys who are CUTE, but seem to be AFC-ish.

Bear in mind that you're there under the pretense of helping her get a man. You and her BOTH know it'll most likely be YOU, but you have to at least PLAY the game. Let me give you three simple rules that'll help you through this night. No matter what happens with any man she approaches, stick tight to these three rules:

1) Don't get jealous.
2) Don't get jealous
3) DO NOT GET JEALOUS!!!

You are the man, she belongs to you. Even if she goes home with some other guy, you KNOW she'll be thinking of YOU the whole time. YOU DON'T CARE. You are her pimp for the night. And at the end of the night, she'll be your ho. ;)
 

Skel

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thanks, god is it friday yet. Im so horny

I have to say that im actually nervous about this because I have never been with a woman older than me ever. Im probably over analyzing this but i dont want it to be too quick
 

PEACEDJ

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Hey, one mistake... you can't tell her you're going to help her out and then change it up with the mindset of actually banging her. If the woman expects you to help her, than that's what she will expect I don't think she'll go out with the idea of having sex with you. Why don't you instead of helping her, go to the bar and flirt with her, act really mature (Women at the age tend to like the settle calm guy over the ****y and funny ones)
 

Brasco

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Smooth move on your part Skel!!!! I have to remember that one.

I don't think you have to worry about her picking up, she is after you!!!!
 

mtllcanpssy

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ya like the above post act mature cause thats what the older women would probably want (i know this'll confuse u but they might want a ****y guy cause its typical of the younger guys and they like younger guys that way too) But my suggestion is that a lot of guys will be too scared to talk to her if you're there with her, don't look jealous and play it cool. But also prepare for what is gonna happen when ya'll come home for that night and how things will procede so you can bang her like a nail. Like maybe make her some kind of dinner and aphrodisiac dessert, (i know not all guys can cook so heres some websites for stuff. for dinnerhttp://www.angiesrealm.com/valentines_day/recipes/dinners.html ) for the dessert make choclate covered strawberries, but make sure she likes strawberries first so ask her at work about it but dont full out ask her u have to kept it secret so its a surprise when she gets there n trust me this will make her knees weak(which is a good thing for later ;) ;) ) ok well get the strawberries or watever fruit she likes, then get some choclate morsels or some choclate bars, melt them in a microwave, n then just dip and set them out to dry on wax paper or put them in a freezer, however i wud suggest to melt it right before u serve it to her cause it will make the seducing of her like 10x easier) and then be like since we werent able to find someone i guess i have to serve these to you and then seduce her with the dessert and make a move on her. then from there just get to a room and screw her like a nail. lol. sorry for making this long and reply back this weekend of wat happens with this woman. good luck young grasshopper.
 
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