I'm attracted to a hot older woman (MILF). How can I get a second chance with her?

Hey Dan & Jennifer:

My relationship with my girlfriend ended with her leaving me. She said that we could remain friends. This happened over a month ago. My ex-girlfriend and I have remained friends. She has a new boyfriend and she seems happy. I am happy for her. We still see each other as friends and I am still invited to her house. This question involves her single mother. From dating my ex-girlfriend I have gotten to know her mom well. She is a very nice woman and very attractive. The other night I was invited by my ex-girlfriend to a dinner at her house. She, her new boyfriend, myself, and her mother were there. Her mom cooked. It was a nice meal and a fun time. After the dinner my ex-girlfriend and her boyfriend left for their date. I offered to stay and help clean up. Her mother was happy for the help. After we got done cleaning up the kitchen from the meal I asked her if she would like a massage. She said “yes”. I gave her a good rub down. It seemed to relax her and she seemed to enjoy it very much. It also gave us a chance to talk more which I enjoyed. I also enjoyed the feeling of her warm and smooth skin. After it was over she thanked me with a passionate kiss I would really like to have sex with her.

Do you think there is a chance given the fact of the difference in our ages and the fact that I was a boyfriend of her daughter? How can I let her know of my desire? Perhaps asking if she would like another massage would give us a chance to talk about this. How can I make this request to her?

Looking forward to your reply. Regards, Jake

[Dan And Jennifer]

Dude, this may sound harsh, but you were there and you blew it...

A second time could be challenging – she may be having second thoughts, wondering what she was thinking…

To get another next time, maybe you can suggest another dinner (to the daughter?) – it’s safe, you’ve all been there before – not a date. But it's still weird.

Chalk this one up to a lesson learned and next time you get the opportunity you may want to take it.

But first...

Think about the long term implications of what you're doing. It could ruin your friendship with the daughter and it's highly unlikely to be a long term affair. So is it really worth it?

[Lance]

That's a pretty unusual situation. First off, I'd like to know how old you are to get an idea of your personal situation. Also, why did your gf dump you? What happened there? Obviously, the mother is going to know everything about what happened between you and your ex (ie her daughter), so an LTR or dating is probably out of the question. If the mother is a total cougar, like on the prowl, I would figure out a way to get her out with you on a quasi-date or another group dinner, then physically escalate (just like with the massage), and try to go all the way. Assuming the mother is single (is she??), she's probably horny and looking for it. All you have to do is close the deal.

D&J are right about the long term implications...if you value your friendship with the daughter, then sleeping with the mother will likely ruin that. Maybe not, but probably. I'm not going to lie here though...if it were me, I would try to sleep with the mother just to let my ex know what she's missing. Hey, don't hate. MILFs need lovin also.

[lisaq]

As an older woman who dates younger men and the mother of a 19 & 23 year old, I'd shoot you down. Not so much because of the age difference but because you dated my daughter. That really is dangerous territory.

Even if, as Lance suggests, she's a total cougar, she would probably still have reservations. Let's put it this way. If I had sex with my daughter's ex and she found out, it would seriously damaged our relationship. In my opinion, there's no sex out there that's worth that.

[Lance]

Have to agree with Lisaq on this one. Leave the MILF alone and go meet some other chicks.

[Dan And Jennifer]

Hey, just an update, we filmed a video on this and just got it up on Youtube...

MILF Fantasy - Should I Have Sex With My Ex's Mom?