The Man in Me

Honestly, I only chose this title to see if I could give TroubleTide‘s gaydar a jolt. Once again, I’m falling behind in posting. Life has gotten extra busy recently. Wife took a part time job so I’m putting extra time in baby care and housework. So, forgive me if my posts are just stupid reports about me utterly failing at finding a new affair partner.

I had a date this morning, a relatively normal coffee date with a mid-forties lady, we’ll call her ‘Samantha’. She answered one of my ads and seemed particularly interested in me, but I’m having difficulty feeling my way with this one. To be honest, I am slightly intimidated trying to bed an older woman, particularly one that is a decade and a half my senior, and has a daughter that is only 3 years younger than myself. Yes, this lady has kids, and grand kids, and she has a fiance to boot. She isn’t quite getting what she wants out of her existing relationship, particularly in terms of affection and sex. Anyways, the date went ok. We met at a coffee shop that Sierra and I had frequented, it would generally be sparsely populated, but today there were a few patrons, and Samantha, having grown up in town, was concerned about someone recognizing her so we walked a block down and stopped into a little restaurant to get some coffee. I could tell she was really uncomfortable with the whole situation, I did my best to put her at ease and just talked normally, we shared pictures of her kids and grandkids and my kid, talked about work, interests, relationships. To be honest, this has been the only date I’ve been on in over seven years, and before that I’d only dated two women before my wife, and by dated I mean I took them out, utterly failed to be romantic and ended up in the friend’s zone. I wasn’t sure how to play it, I’m good at getting a hug, so that wasn’t a problem, so I think I bridged the awkward physical contact barrier successfully on a couple of occasions, but beyond that I wasn’t sure how to promote any level of intimacy. I can’t quite put my finger on it, but something didn’t seem quite right. Could be that I’m just really bad at this, or it could be that there just isn’t chemistry, or could just be she was too uncomfortable with the whole thing. To be fair, I’m always guarded, I didn’t reveal where I work, just the basics of what I do, where I went to school, how I met my wife, that kind of thing. I remember that when dating my wife I felt it was easy, I flirted with her effortlessly, but even then it was over two weeks of hanging out before I made a move and we kissed and became boyfriend/girlfriend officially. I’m not sure how much my inexperience showed. In any case, I didn’t feel particularly uncomfortable at least, but I was kind of unsure how to proceed, so I just kept being friendly, flirting a little here and there, tried to gauge her, and looked for openings. Finally, I needed to be getting back to work, so had a parting hug, she suggested we have lunch sometime and left. In hindsight, I should have offered to walk her to her car, but she did seem somewhat uncomfortable with someone seeing her, but all the same, that was a missed opportunity. She’s an attractive enough lady, but I’ve also been spoiled with more attractive girls meeting me just to have sex with me on a couple of occasions. At that level, I’m not sure about how much I’m willing to pursue a dating relationship with Samantha. I really just don’t have the time, finances, or desire for regular dates. It was a bit different with Sierra, we planned to have sex our first meeting, which flopped, but we did succeed on the second occasion, and then it was more of a desire to spend time with her and ‘date’ her from there on out. We had fun together and I just wanted to be with her. It really was an ideal situation since everything was up front, there was not a substantial investment and risk taken and our relationship was almost immediately rewarding (a bit of an understatement for the most mind-blowing sex I’ve ever had). It could just be that Samantha and I just don’t have much in common, conversation with her wasn’t bad, but it was superficial and I didn’t detect much connection. Thus in hindsight, I don’t think she would be someone I’d like to date, since we really didn’t seem to hit it off. Could just be that she was uncomfortable. I’d like to try having a sexual relationship with her, but sounds like she wants something more than that if she is pushing for dating at this time. Perhaps I’m just too impatient. So, I’ll have to wait to see what happens with this one. I may try one more date, but given how little spark there was, I’m not holding out too much hope. May just want to hold out for either booty calls/hook-ups or more dateable prospects.

On the booty call end, Elle has been in continual contact with me, but we are still going round in circles. She’ll text me, ask me what I’m up to, she’ll tell me she is at home alone, she wants me to come over, but then she can’t seem to work up the courage to give me her address. She asks me what we’ll do, and I just tell her we’ll hang out and see where things go, and she then usually proceeds to flirting her way till we are talking dirty to each other, then tells me she is too horny and anxious to have me over. It is quite comical really, the whole process starts over the next day. Reminds me a bit of where I am at with Minda. We still text from time to time, I’ll ask her what she is up to, we’ll text a bit, she’ll want me to come over, but always seems to get busy. I feel like I’m in an endless orbit around these girls. I guess the only thing that keeps me in communication with them is that it doesn’t take too much effort to do a little texting from time to time, and the slim possibility that something could happen. I should just call this the ‘Sierra’ effect. By all rights, the only sign I got from my communication with Sierra initially was that she was flaky and blowing me off and that nothing would happen between us, then somehow something happened. So, keep all these irons in the fire I figure is probably worth it for the effort it takes, you do never know after all.

I’m optimistic about my hook-up scheduled for this Friday, Lisa, who is cheating on her fiance. No reason not to be I suppose, but I still won’t be surprised if she doesn’t show.


8 thoughts on “The Man in Me

  1. I agree with troubledtide. If you meet somewhere more private you might have better luck. I know if I’m out in public locally, I worry about being seen by people that know X. That’s what I’m glad I can just go over Raoul’s and have our fun. Good times. It took me a good while to find Raoul. Been doing this for about 2 years. You’ll get there. =]

    Liked by 3 people

    1. Sounds like you have it made with Raoul. It took me a year to find my first AP, but she was only able to host every once in a while, now I haven’t heard from Anne in a while, and we all know what happened with Sierra. It would be nice to find a good, go-to AP.

      Liked by 1 person

    1. I have repeatedly said that I’m open to an older woman, lol, and this isn’t the first I’ve pursued. At least you were of legal age by the sound of it by the time you were making babies, not with this gal and her daughters 😉

      Liked by 1 person

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