I couldn't really think of what I wanted the appropriate title of this thread to be... I just know I need to write this out for myself as it's been randomly bugging me.
A few years ago I met this MILF off POF. She was like 38 at the time with two kids and divorced. Her ex husband cheated on her with someone he worked closely with. They tried counselling etc.. but ended up splitting where she has the house and I think he gets the kids every other weekend and maybe one day during the week? Another important thing to note is that her ex husband has a powerful societal position, I'll leave it at just that.
So anyway we met for drinks a few years ago and she was into me. Smiled big when she saw me, sat close, had multiple drinks etc... These are all signs I've found are IOIs in my dating experience. I had another date that same night with a girl I already hooked up with and liked more so I kind of ended this one short. I walked her to her car, it was raining but she let me kiss her, albeit a very short one which I stopped because it was raining.
-An important note to mention is I don't live near her but she was under the impression I was moving to her area.
Anyway she ends up texting me the same night saying she had a nice time and hope I got home ok. I text her back something similar and said something about hoping the kiss was worth getting wet from the rain to which she responded back definitely.
So we end up meeting again for drinks maybe a month or later. This time it was not a good date. She seemed a bit more standoffish and didn't really order additional drinks etc.. I was not having a good evening with her at all so I eventually ended the date. I figured she wasn't into me or something but to my surprise that same evening she texts me with "hey you seemed mad tonight" or something like that. I responded back saying I wasn't mad just disappointed, I said she was acting aloof etc.... She responded back with something along the lines of that she didn't mean to etc... we had some back and forth texts and she basically suggested we should see each other again which I agreed.
Ok so this is all like close to two years ago at this point... I have someone that I've been with for years so finding time for side play is difficult at times. Also the fact that her ex husband in a position of power I often thought pursuing this woman might be more trouble than its worth so I backed off
Several months later she texts me out of the blue saying hey its me I thought of you hope you are doing well. I responded and traded a few texts back and forth and that was it. Over the next year we both would randomly text each other but never made plans to see each other again.
So COVID hits.... we still text now and again but I basically used that as an excuse to why me moving by her got delayed. But anyway I was working near her this past April and the COVID situation was better with establishments being opened etc... Plus we both are vaccinated so I decide to make plans with her.
We met at this bar and had a few drinks, it was going well although there were some silent pauses I noticed she held eye contact with me for a few seconds even during some pauses. All in all we did have good conversation she did order an additional drink. At the end I walk with her to her car and I have her drive me to mine since I was parked in a different lot. I have her pull next to mine and I go in for the kiss..... well we start making out hardcore both of us not wanting to stop.... I was just letting my desire and sexuality take over with the kissing/carssing etc... I started kissing her neck too etc.... She started putting her hands under my shirt and rubbing my chest.... Eventually on her own she unzips my pants, caresses my nut sack and then proceeds to jerk me off while we are passionately making out..... Honestly that's one of my favorite things to do with a girl... make out while she strokes me.... it felt so good and I eventually blew my load all over hand and it got on my shirt lol
Well we end up departing and she texts me the next day saying she had a great time and that she usually doesn't hook up in parking lots but she was so caught up in the moment with me. I texted her back saying some nice crap too so she didn't feel like a slut and it was good. Then we both went silent for a bit but did the usual random texts weeks/months later.
So at this point I was back to the same dilemma... should I try to pursue banging her at least once or would it just be more trouble than it's worth given potential issues her or her ex could cause me. For example if she somehow I found out I am with someone I'd be toast! So I continue wavering back and forth and don't really text her much nor does she....
So like two weeks ago on a Friday I text her in the morning saying Happy Friday or something.... She usually always responds to my texts but this time did not.... So in the evening I texted something else "well hopefully it is lol" She then responded back pretty quickly saying "happy Friday (some emoji which she likes to use), I'm on vacation with my family" I responded back with "I wish I was on vacation lol" She didn't respond at all....
So I think maybe a week later which was last week I texted her something random like "sounds like you had a great summer" She did not respond at all....
So a few days later I texted her "hey you don't seem as talkative lately, I hope everything is ok" She did not respond
So that's where I am now.... Do I look at this as a victory getting that hand job experience from her and not getting in trouble? Maybe it's a blessing in disguise..... or should I try to find out why she suddenly ghosted? My guess is she probably started getting serious with some other guy who is in her area... should I try to find that out just for knowledge?
I keep going back and forth about this and it's bugging me.
