A
male
age
30-35,
anonymous
writes:I'm 24. There's a woman I work with who's in her late 40's, divorced, still pretty attractive, and friendly with me. I've never been with a woman that much older than me before. I'd be interested to experience sex with her. Her oldest son is almost my age. how should l proceed? Would she be interested in sex with a younger man?
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female
reader, aunt honesty  +, writes (21 December 2016):
 Dangerous territory when it is someone you work with. Plus she is probably old enough to not want a quick hook up with someone so young. I could be wrong, but usually older women want something more.
A
female
reader, Andie's Thoughts  +, writes (17 December 2016):
 Firstly, and most importantly, women are not sexual objects, so I think you need to rewire your attitude a little.
Secondly, many women go for younger men when hooking up.... *HOWEVER* most older women aren't looking for hook ups, especially when they are the same age as their child.
Thirdly, "don't crap where you eat" is a real issue - if this goes wrong, you may get fired or (at the very least) become an outcast because people see you as disrespectful and almost predator-like.
OP, I really think you should give this a miss and hook up with people in your age bracket, who are actively looking for one night stands or FWBs.
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A
male
reader, anonymous, writes (17 December 2016): You say you are friendly with her already so show more interest in her like getting her her coffee,helping her, showing her you care, compliment her, you know,find ways to show her you are interested and you would like to know her better. Dont be crude as you have already come out in your post. If she is interested in you in that way she will find a way to let you know.
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A
reader, anonymous, writes (17 December 2016): Dude! Seriously?!! How about wanting to get to know the lady, and wanting something other than just sex with her. And you wonder why women have such a negative attitude towards men and the way we approach them?
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A
female
reader, anonymous, writes (17 December 2016): I am in my late 40's, very attractive, and I would not be interested in having sex with a guy your age. I prefer older men. Why? Because older men are more experienced, patient, mature and know how to please a woman. Young guys in general just want to get off. And have no idea how to make love to a woman. I guess it comes down to experience vs. stamina. I prefer experience. An older guy makes me feel cherished, special, young and loved. And he knows how to please me and knows my body and how to pleasure every part. I want a man who knows what to do. Not a man I have to teach. I am all for being aggressive and I am but the thought of a kid young enough to be my son is a turn off for me personally. Also, just because she is being friendly does not mean she wants to fuck you. I am friendly with plenty of people, younger guys included. It does not mean I am interested in them sexually. Sometimes I take a motherly interest and that is all. So, tread very lightly here. You could risk offending her and being reported to human resources. It is a dangerous game to play in the work place. So think with your big head and not your little head to avoid being put into a dangerous position at the place you earn your living and where SHE earns her living too.Certainly I can understand the attraction but make sure you are not trying to impose your own fantasies on a person who is not on the same page. Sometimes our beautiful fantasies are better kept to ourselves. Also, do you know for sure she is not seeing someone or has a boyfriend? Some people keep these things private and do not talk about them.I can tell you one thing. IF she is interested in you sexually, she WILL make a move. So, if I were you, I would sit back and let her take the lead. She will give you plenty of clues over time to lead you in that direction. If you don't see them, then hang back. You will risk rejection and loss of your job. So, be careful. But I caution you to be careful with workplace dalliances as often they will end. Sometimes badly and then you must continue to see this person everyday. So, think about if things did go sour if you did get together. Also, think about this. Many older women who DO get involved sexually with young guys are looking for a bit of fun. They are into the young guy's stamina and enthusiasm. They are not interested in a relationship with him. So, even if it go down this road and you had sex and continued to have sex, beware.... and try to contain any feelings you might have about her or any delusions of it becoming more. Because it won't. And the possibility is there that once she is done experiencing your "novelty" she will leave you behind. Could you handle that? Or conversely, what if she became hooked on you? And you discovered that the sex wasn't all that good or she might be the one to become too attached, could you break it off? Knowing she might become bitter? Try to get revenge? Become even more aggressive and not want to let you go? Cause you a whole shitload of headaches at work and your personal life in general?Hope I have given you some food for thought.Our choices HAVE consequences.
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A
female
reader, Youcannotbeserious + ♥, writes (17 December 2016):
 I suspect that, at her age, she has enough sense to only want sex in a committed relationship. She is highly unlikely to want to be used by someone who just wants the experience of sex with an older woman. However, it is always possible that she would be happy to have a no-strings hook up with you, especially if she is feeling a bit lonely and in need of human contact.As long as you don't lead her on or lie to her about what you are offering, you are two free adults and there is no reason you should not hook up for the experience - as long as both parties are fully aware what is on offer.
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A
female
reader, anonymous, writes (17 December 2016): Good grief. You're looking at this woman as a piece of meat. You want to have sex with her. You're not interested in her as a person, you don't want to find out if you and she would get on, if you have similar interests and outlooks and values. You don't want to share a meal, drinks, fun times out together? You just want to stick your penis in her vagina. Charming. What do you think she is? A prostitute?If you're actually going to proceed and act as if this woman was put on this earth for your pleasure, then I have no idea how you would go about it. Speaking as an older woman who has had plenty of much younger men interested in her and has never entertained a single one of them, I wish you good luck. I knew what they were after. You never know, she MIGHT have the same values and outlook as yourself and say yes. THEN you are taking the risks that come alongside a sexual liaison with people in the workplace. She might start to think it meant more than a quick poke to satisfy your curiosity. Then where are you? Up shit creek without a paddle. Exactly where you belong.
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A
male
reader, anonymous, writes (17 December 2016): 1. You can and cant approach an older women like this. Some want to fuck. Others want a romantic connection. Older women aren't meant for conquest and they will shut down your games. Get to know her and show her why you stand out from all other guys she been with. Also, let her know what you want but not to aggressive and especially in public show her you want her, kiss her neck, hold her hand, grab her ass, and etc. If you want her feel like you are embarrassed by her, then you are screwed. Take it as it is a learning experience Good Luck and above all HAVE FUN!
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