How would you pull this off?

[S. Pryor]

There’s this woman at my school that I’ve taken a liking too and I don’t really know her feelings for me. I met her one day at the school (she works there) and we had a brief chat. I didn’t know she worked there because she was dressed more casual then what she usually wears. Her attire was great but she usually wears a pants suit. As time went on I saw her more and more and every time we saw each other she seemed to take a genuine interest in me. Almost as if she cared about me to an extent. She even gave me her business card and told me to call her anytime. Now I don’t know if it’s just me being over analytical but if there’s a way I can find an “in”, I’m all for it. Here’s the kicker: She’s a 40 something and I’m an early 20 something. She’s divorced and has two “kids” that are a little older than me. Now I know a relationship is completely out of the question but she’s a cool, attractive woman and I would like to have sex with her. She’s all professional at school but she looks like she would shed all of that in the bedroom. I wanna see how great her pussy most likely is but she looks like the type that’ll be like “young man that’s inappropriate” if I even tried to ask her out for “coffee“ as they say. How would you find your way in despite these circumstances?

 

[S. Pryor]

Any advice at all? Anybody?

 

[King Turi]

Man, seriously, what have you got to lose by calling her "anytime" and getting her to meet up with you somewhere?

The worst that could happen is you don't get t bang her, it's not like you are her best friend or anything awkward.

 

[Die Hard]

....every time we saw each other she seemed to take a genuine interest in me. Almost as if she cared about me to an extent. She even gave me her business card and told me to call her anytime.

As if she CARED for you? I get the idea that this woman has never given you any signs of sexual interest but she HAS given you signs of caring about you. I don't mean to be rude, but somehow I get the idea that you're still quite the AFC (takes one to know one ). AFC's have the habit of building a "connection" with women, getting close to them, not in a sexual way but more in a "caring" way. Basically they hope that establishing this "connection" will be their way in (to her heart, to her pvssy, whatever). Seriously, do you remember the moment she gave you her business card? What were the two of you talking about before she gave it to you? Were you exchanging signs of sexual interest? Or were you exchanging signs of emotional bonding? The kind that could be described as: "we understand each other", "I know what you've been through", "there is a connection between us" or whatever.

I could be totally wrong here, so forgive me if I am...it's just a hunch!

 

[S. Pryor]

In all fairness, the woman was AT WORK. You think she's gonna be talking some freaky **** at WORK of all places? I can't tell her let's meet up and such and such place cause the number she gave me is her line at the school. Like I said "it would be inappropriate". And I also said, I don't know if I'm being over analytical which you are attempting to prove to be true. Of course that's just my opinion...I could be wrong...