Can not figure out if my flirting is working?

[mattm84]

Here is the situation, I am 21 years old and I have know this woman for about 5 years. I have only recently started flirting with her or telling her that she is sexy etc. She is older than me though 55. We have a lot in common. Here is my current status I work with her and to work she wears these capri pants, the tight pants that go to about the thigh area. Anyway they are very tight,very revealing, literally I can see her underwear Anyway, she does touch me whenever she can and sometimes when she talks to me she keeps her hand on my arm for more than a few seconds. Ways that I have showed that I am sexually attracted to her is by standing real close to her when I talk to her, I mean holding hands distance or closer. I have also spanked her twice today, I told her she was a bad girl for helping a co-worker with a job that they did when she wasnt suppose to. She laughed or didnt almost didnt respond. Also I think when she knows Im watching her she either reaches to do something or bends over, not 100% sure on that though. How do I make SURE she is attracted to me? How should I go further, should I make a move? PLEASE HELP! Shes driving me nuts!

[asdf]

No idea. I never wooed a 55 year old before

[Shidoshi]

If you're already comfortable enough to be "spanking" her I would say its safe to assume you can ask her out. Have you tried that? Also....damn...she's 55? How old does she look to you? I have seen some fine older women who take care of themselves, but 55? Well...hey if she's driving you nuts you need to do something about it! She's probably a little flattered that a 21 y/o is sexually attracted to her anyway, you may get lucky!

[RandomAdvisor]

No idea. I never wooed a 55 year old before

 

Yeah that's a tricky one. I'm assuming this woman isn't married, right? Divorced maybe? With that big an age difference she might think you're just being cute and not serious. Flirting might not work, you might want to just be very blunt and tell her you're interested.

[tabytha]

sounds like she's attracted but I'd pull back if I were you. She may simply be an older woman flatter that a younger person is attracted to her. She may simply need the ego boost and not really reciprocate your feelings.

 

My advice though is to take it out of the work place. Ask her out for chummy work drinks as a cover if you must, but be aware that sometimes playful flirting can be misconstrued as sexual harrasment, and even if you and your lady friend are not offend it may offend those around you and they (sadly ) have the right to complain. Arse slapping though fun can get you in trouble at work.

 

So take her for a drink after work and see if you can work your magick there

[mattm84]

she looks 30 at the most, I like older woman anyways I think I am past the asking her out for a drink stage. We have hung out and went shopping and crap many times. I think this would be a more friends with benefits situation, more if she wanted. And the sexual harassment issue isnt an issue. Its only me and her when working. I need to know if i should make a move, or something, what signs would I get that she WANTS IT?

[asdf]

i don't know. she may have an old fashioned way of flirting, and she'd also be very much more experienced

[pandorasbox]

dude u outta ur mind? she's ur granny's age for pete's sake