• 1 week ago
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I’m a man in my 50’s. I have a 20-something female friend, we chat now and then. I’m kind of like her dad, in a way, because her dad’s been out of her life since she was a young child. So she likes to talk to me and unload her thoughts. I give her what advice I can. There’s a part of me that wants to make the relationship sexual, but I’ve kept those thoughts to myself. Not that she would be interested, but she mentioned something once, about how she’s very open minded about sex… it was like she was hinting, but I didn’t follow up. I think it’s better this way, but sometimes I regret not following that line of conversation with her.

All Comments

  • I’m 56 and my friend is 29 this Friday. She always tells me how nice I look. We go to dinner, we go driving, we go to rock concerts, we work out, we go for frozen yogurt. She is my BFF. She wouldn’t turn me down, but do I really want to be sleeping with her? There goes the friendship. Her legs and ass are to fucking die for, though.

    Anonymous July 11, 2018 5:44 pm Reply
    • I have a friend that is 29, I’m 47 and married, we’ve talk ,our relationship is just taking off. But she told me she was very much into older men, and we are the ones who need to lead. She said she wouldn’t initiate , but if I did, she would follow and not turn me down , but I agree with you, might you sacrifice the great thing you have now ,for a possible disaster? I guess the thing you
      Need to look for are the suttle hints. Is she giving any? Does she touch you? Is your eye contact longer than usual! They say your pupils dilate when your with someone you like!
      But like you would hate to ruin a good thing!
      Tough choices good luck!

      Anonymous July 11, 2018 5:59 pm Reply
  • Don’t ruin a good thing! Forget the sex thing .you’ve moved on from that.it’s sounds like its become a nice relationship ,safe. Dont spoil it. Let the relationship develope more , was she looking for a father figure or something more? The sex thing Is thin ice! Watch it .

    Anonymous July 11, 2018 6:05 pm Reply
  • Keep it cool sir

    Anonymous July 11, 2018 6:09 pm Reply
  • Just follow your instincts. You might regret not doing what you honestly want in the first place 😉. Just let it be sexual if it is or if it’s going to be.

    Anonymous July 11, 2018 9:03 pm Reply
  • Use lube

    Anonymous July 11, 2018 9:07 pm Reply

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