OK, crazy update time!
I went to the bar where Ashely works last night at around 9 or so, and she was working. First thing I checked on was the teacher bit; she’s apparently aspiring to be a teacher, so that kind of solves that mystery. She asked me to draw a portrait of her, and I did. She was done with work by 10:30 or so, and I had the portrait ready by then. She loved the drawing, and gave me a hug and a quick kiss; not a lover’s kiss, no tongue or anything, but also not on the cheek either. She sat with me while she ate her after-work meal. We made small talk, and while she was eating, guess who texted me? Yep, the aforementioned hookup from a little while ago; we can call her Laura.
Laura wanted to know if I was out and about and where I was. I told her. Ashley had to get going, as she needed to get up early for some reason, so she gave me a hug and another quick kiss and left. About ten or fifteen minutes later, Laura showed up. Here’s the background on Laura; she’s 31, divorced, has two little girls aged 6 and 4, and recently quit her job (without another job lined up…ouch.) Ashely is relatively tall (maybe 5’10" or so), blonde, and maybe 20 or so pounds overweight; in contrast, Laura is about 5’6", a redhead and very petite. There was, as you might expect, a marked difference in the interaction with Laura versus Ashley.
With Laura, there was a lot more physical interaction, as in her touching my shoulder or thigh as she talked…and if she wanted to whisper something to me, the touch would often go from top of thigh to about 6 inches away from YESYESYES territory. She stayed with me until close and we talked about a lot of things, most of it being light conversation with a lot of humor. Conversation drifted from our crazy ideas about opening a restaurant/hotel combo chain to the sensitivity of nipples (long story) and when she was ready to leave, I got another kiss; this also on the lips, also not open-mouthed, tongue searching level, but she lingered a bit longer, and gave me a playful slap on the ass as she left.
One of the bartenders cut right to the chase and asked me outright; “What’s up with you and those two?” To which I could only say, “I really am not sure.”
Pros with Ashley:
Young, pretty, smart girl. Well-read and ambitious.
Cons with Ashely:
Intelligent but not experienced and still needing education in certain areas. Age difference could be a barrier no matter how you slice it.
**
Pros with Laura:**
Relatively close in age, intelligent, well-read plus I’ve always had a thing for redheads. Also not shy when it comes to talking about her nipples. I gotta count that as a pro.
Cons with Laura:
Two kids, a divorce, and currently no job; pretty much every red flag in my head is saying she’s looking for a sugar daddy.
I do enjoy my time with her and find her attractive, and of course the age difference isn’t that much…but I’m skeptical of her motives, moreso than I am of Ashely’s motives. She has kids and she really wants to provide for them, so maybe she’s looking for someone to take care of her and her kids more than seeking some deep connection to someone in a romantic sense.
So far, no sex; hell, the kisses are kinda tame, too. More investigation warranted.