I went and stayed with my dad this weekend because my little brother started Pop Warner (its his first year) and I wanted to go watch him play. I don't live with him obviously. I decided to spend the weekend down there to just be with the family.
I am 21 like a lot of you know. After my brothers game on Saturday, his coach asked the parents to come to this local sports bar where his band was going to play. My stepmom really wanted to go and my dad had his poker night, so she asked if I wanted to go with her and I said yeah because the beer was on her and she can throw some back.
Here is where it gets really interesting....
We are sitting in the bar having a good time and my cousin shows up with her fiance and another friend of theirs. Their friend is this really hot 40 year old woman. I have a thing for MILFs so I was flirting. She starts flirting back! No big deal, older women love attention from men especially young ones if you are middle-aged. As the night goes on she becomes more and more flirty and even starts touching me and rubbing my arm. She then started running her foot up my leg. At this point I didn't know what to do. If my stepmom wasn't there I would have taken this girl back to her place and had a grand ol time.
During our conversation she found out that I like Jazz and the Blues and suggested that we go to Palm Springs next weekend because they have some nice jazz bars. For those not in SoCal Palm Springs is about 1.5 hours away from OC and a few from LA.
She asks for my number and I give it to her, then when she left she hugged me and stuff and she went for a kiss and I turned away because my stepmom was there and I didn't know what to do, I just felt weird.
So about an hour after she left she calls me and asks if I want to come to her house and go swimming (she lives over an hour away from my dad's house). She then called me twice this afternoon and evening. At this point I am a little scared. She seems kinda obsessed. Last night I thought she was just drunk and by today she would be over it, but shes not.
I want to just take care of business and move on, but I am afraid shes crazy and I could be getting myself into more of a mess than I want to. I also know shes my cousin's friend and I may cross paths with her again.
Maybe she doesn't want to know about it but you stepmom probably wouldn't hold it against you. Make the date, feed her some drinks, and pay attention because you just might learn something!
Damn...first off, I ought to say thank you for letting me live the MILF dream vicariously. I'll be 25 soon, so I've still got some time, but the clock is ticking down to the moment when they stop being MILFs and start being peers.
The best advice has already been given. You need to strike while the MILF's hot. She might be obsessed, but whats the worst that could happen? And let's face it: if a 40-year-old woman is chasing a 21-year-old cousin of her friend, she might be after the same thing you're after - she may just want to hit it and quit it.
Also, pics would probably help us give better advice.
I had a date with a woman in her 40's when I was 21. It was fantastic - she asked me out on Valentine's Day. Saying yes was the best decision I ever made.
Things were awkward at work for the month or two afterward, but that shouldn't be an issue. Get to it, kid.
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by Phatferd » Mon Sep 12, 2005 2:16 am 
