I am in my 40’s in a sexless marriage. It’s been 2 years since my wife and I had sex. I do construction work and handyman stuff. From time to time, I do work for a woman in her 70’s who was widowed around ten years ago. I always catch her checking me out, looking at my crotch, butt, and the rest of me like she’s interested and horny. I know her pretty well and so far haven’t said anything. Now I am thinking of having a fling with her. She’s lonely. I feel bad for her and we get along great. She moves around like someone ten years younger. I’m thinking I could give her one-time fun, and we could both get something we miss.  But despite her checking me out, I’m not sure if she’d be open to a fling with me. She knows my wife, which is why I think she hasn’t dropped a major hint. How can I let her know I’d be interested?

Responses

  • Michael Castleman says:

    Fantasy is easy. Reality is more difficult. Your fantasy is that you have a quick fling with your older widowed client and that nothing else changes—neither your professional relationship with this woman, nor your marriage. That’s possible, but so are complications. What if your wife found out? What if your widow wants more than one roll in the hay? What if discord with her torpedoes your working for her? Before going forward, I urge you to to consider all the possible problems that might develop.

    But assuming that you’re prepared to deal with the consequences, whatever they may be, you need to decide how you feel most comfortable approaching her—face- to-face or some other way. If you opt for face-to -ace, you could pitch her the next time you’re working for her. But then you’re in work clothes and sweaty, maybe not the way you want to appear when you pick up a date. In addition, a face-to-face pitch means you have to spit out the words, “Hey, want to have a fling?” Can you do that comfortably? And could you then say, “But I only want to do this once….”

    The other way would be to send her flowers and a note. The flowers would imply that she’s more than just a client to you, and you could take your time crafting the note so it says what you want to say. You could also say that you’d be happy to take her out to lunch and discuss things further. If I were you, I’d go the flowers-note-lunch route.

    If she says yes, then I hope you understand that many women their 70s have an issue with vaginal dryness that can make intercourse uncomfortable or impossible. For some, a commercial lubricant resolves things and allows comfortable intercourse. But for others, even well-lubricated intercourse feels uncomfortable, and those women usually prefer hand jobs and oral. If things get that far, I urge you to discuss this with her, and to ask if she has any other sexual issues you should know about, for example, many older women feel reluctant for lovers to see them naked….

    Also, if she says yes and you enjoy the fling, it’s quite possible that she, or you, or both of you might want to get together repeatedly. That would involve more negotiations with the possibility of more reality intruding. Like I said, it’s easy to fantasize a fling, but more complicated to consummate it and come out the other end feeling good about it. Good luck.

    • toll94 says:

      Great advice and things to think about. I am glad I asked and I don’t know if telling her in those would be the way I would feel comfortable. I think if anybody went to a woman of her age asked bluntly I would be slapped to the face. Flower, lunch, note could work but I think this might send wrong message of romance more than a sexual encounter. I guess what I was looking for is that I want her to know without going over the line I am available if she decided to go to that extent. Now most likely it never happen but if I want her to know that I be willing at any second to have a fling. If developed any more than one time then at that point I think we would both understand the consent of the other and respect both are boundaries. As far as sexual side of things if it ever happened I wouldn’t force anything and if she just wanted mutual masterbation, handjob or oral and no intercourse I would respect that. Point I am trying to make is she would be control of her desires and wants. If nothing ever happens then so be it. Question remains is how do I tell a woman of her age indirectly that I be interested in sexual foreplay or more?

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