Picked her up as agreed, she was on time and looked smoking hot. She didn't dress slutty or provocatively, I don't think that's her style. But her natural beauty, slim body and well-portioned curves under as simple black blouse and slacks we on point for anyone who likes demure babes.
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Off to my place as planned since all inside dining is currently closed (Thank you, Gov. N!) and we chat for a bit on the sofa before I order Italian food from an upscale place through a delivery app. She sat next to me as I checked out so I know she could see the total was around $75. My guess is that based on her modest earnings, and her living status, she probably spends less than $15 on a meal.
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As we wait 35-45 mins for the food, I pop open the 1st wine, a French rose for her first tasting lesson. She's a good study and seems to have a good, though still young, palette. As we nurse the rose, the discussion turns to the site, and what she was hoping to accomplish there, before she decided to lave that path. I mention that I have deactivated my profile for now (actually I just hid it from the dashboard/search) and I'm not pursuing any new arrangements for the time being... this leads to some discussion of our new friendship and her deepening interest in learning about wine, plus her desire for career mentoring. I casually say the arrangement path is still available if she is interested, and BINGO! she says she may be. (Note: At this point, word choice in these conversations is critical - I deliberately use "arrangement" rather than "sugar," and I stay away from transactional modes as well.)
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We talk about the difference between a casual friendship and a sugar relationship (i.e.: add sex + financial help) and then talk about possible schedules, sexual preferences, testing, building trust as a critical foundation, and privacy & discretion needs. She mentions she broke up with her BF three months ago - 25 yrs old and "successful" - but in a mistaken attempt at mentoring he was pushing her hard to go to nursing school due to the high pay. She has zero interest in that and was annoyed he did not "get it." Also, in the context of this part of our convo she says she's been tested since they broke up, but not active.
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Aside: So she's horny, hungry to learn, doesn't tolerate rudeness, appreciates and values mutual respect and she likes nice things. As long as I'm not a total dick, I'm hopeful she will eventually talk herself into a commitment.
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We move on to related areas, she is on birth control with an IUD but laments that without health care coverage, she is reliant on Planed Parenthood for birth control service and they cannot provide IUD support. I bring up ACA plans for California, and take that opportunity to suggest that I would be happy to help her select a plan and could, as an example of support, pay the monthly fees and co-payments when needed. She seems to like this idea... but she's not committed yet. She has yet to ask about, nor have I offered, any specific allowance amounts. If I can set up a $150-$300 a month auto-pay for her insurance plan and she's happy with that along with the wine and mentoring, I'll score a major jackpot.
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If!
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The food arrives. I open the next bottle, a Cline Cellars Sonoma Zin, and we tuck into our Caesar salad and pasta. She loves the zin, and I ask her to take the rest of the bottle home if she likes. She likes.
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After dinner, she says she's tired after a long day of work and I offer to drive her home. Off we go. She gets the bottle from my trunk and we exchange a hug and kiss on the cheek.
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Today she texted me with a cheese and wine pairing question. And she closed with "see you soon!".
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Life is good
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The Cat 