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Update! I told her (M)27 (MIL)47
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So I’m happily reporting back! I did it! She’s right where I want her. MIL & I are now fwb for a lack of better terms. We always use to kiss on the cheek and eventually we got into kissing on the lips occasionally. Not all the time, only the times where people aren’t looking or when we are drunk. So having been doing this, me & MIL were alone in the car, I had picked her up from store and we were just chilling driving and we started talking about to sexual things and about her husband doesn’t fuck her and she hasn’t been fucked in 2 months etc etc. So me slowly assembling my game plan in my head, i say “how about then you give me a real kiss” and she leaned over the center counsel she kissed me! twice!! I had the opportunity so the second kiss, i stuck my hand underneath her leggings and grabbed her ass and some of her asshole as she kissed me. She got out and immediately texted me “see you tomorrow” I replied “you sure will” Second day came same thing she got in the car we make out and chat for a bit this time I got to the point where I was touching her tits while we drove. She asked me this time “How often do you have sex” I replied “at least once a day or when I can” she responds “oh really” I said “do you want to see?” She was shocked that I have video of me fucking her daughter, she fucking said “YES” I showed her and she watched the whole minute video of me beating the brakes off my wife and she was like “wow, you fuck really good” I was so turned on and said “next time you can join us” she looked up and chuckled. 3rd consecutive day (which is today as I write this) met us this time she gets in and only gives me a kiss on the cheek. She was playing hard to get and told her to lean over and kiss me. She did it. We parked and started making out like tongue biting etc. I’m already in her leggings rubbing her asshole, just cause I couldn’t reach over to far enough. I tell her take her tits. She lets them drop and they’re a perky C cups I know cause I asked. I started to slowly rub them and pinch her nipples. I bold asked her “I’ll suck them right now” and this is where I dropped the ball. She didn’t say anything just gave me a smirk 😏. I was so caught off guard and mesmerized by her tits that I couldn’t respond and just sat there. Anyways we are passed that and I’m slowly trying to take her pants off in the car. She wasn’t letting me, only got to see her underwear. I go ahead and open my pants and show her my bulge and tell her to feel. She leans over and starts rubbing my stomach and slowly trying to build up the courage to in my underwear to grab my cock. But she didn’t do it and wasn’t about to force her hand. I wanted it to be natural. So we make out some more and then say bye.
Now my question is. How should I proceed?

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1 year ago