I have coached my friend for 2 years who now works for me as a coach. We get on well and it's not uncommon for her to tell me about her sex life or that of her friends - kind of with flirty overtones. I'm not sure if she is telling me this as a way of initiating intimacy or merely as conversation. Let's face it, we're never going to have a relationship but I would love to sleep with her. I'm a little hesitant to take my flirting with her further considering (a) her age, and (b) the dynamics of our relationship.
So, should I put it out to her that I'm interested? Advice from women would be well appreciated.
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I wouldn't be surprised if she is impressed with your degree of sophistication, which she finds lacking with people of her age group (including herself). But that only means she has a desire to learn and seek continous improvements, which is a positive trait.
That being said, when it comes to "Does that desire to learn includes learning about what it is like having sex, or getting into an intimate relationship with someone significantly older than you ?", it is a lot more complicated. Even if she is honest and says that what she is after (with you), and you are being honest about why you find her attractive (innocence, smooth skins, bright, ...etc.), I would consider other factors, such as the consequences of such a relationship on both parties.
If you two meet at a bar, and find each other attractive, and both know what both want is a one night stand, or some casual sex, then it would be like a business transaction, "I get what I want from you, and you get what you want from me"; it is none of anyone's business (not even the police's), except yours', literally.
Given your work circumstances, that's not the case. There is a chance that she gets emotionally involved and hurt when things go "sour". Not only does that affect your working relationship, you will leave behind some permanent scars.
If you want to have sex with young girls, and you 'must' do it, it is far better to pay for it, and do it with "professionals" who "know what they are doing", and upon completion of the transaction, leaves no scars or trauma.0