The anticipation over meeting Leah this afternoon did not overwhelm me. I'd been thinking more about Audrey and Sunny. Even though Leah has her own apartment, her young age gave me pause. But we were meeting today, and I'd seen some pretty nice photographs to know that she was a very lovely girl. Being Sugar Daddy to a early 20s woman had some serious appeal for me.
I arrived a few minutes before our 4 pm meeting time. I picked the same neighborhood coffee bar where I'd met Arabia, Gia, Naira, Heather and Annette. The cooler weather ruled out a table on the outdoor patio, and the inside was very crowded, so I picked a table to avoid losing out on one once she arrived, and waited.
Leah showed up at about 4:05, so not too bad. I saw her enter from my vantage point. She had cut her dark, wavy hair, which in the pictures appeared to be well past her shoulders, but now it stopped right at her shoulders. She wore a light colored top and longer skirt. The top showed off her very beautiful breasts. Her dark eye makeup reminded me of someone (well, Hayden at first), and she had a vaguely middle-eastern vibe going. I liked her right away.
We stood in line and made some small talk. She was majoring in psychology, and is taking a winter break online course before returning to classes part time in two weeks. She's also interning once a week. Currently she has a lot of free time, but once she returns to school, she'll only have a couple of free days per week. No worries, I thought, I only needed one!
We found a different table, farther away from the door, a little less conspicuous. She excused herself to use the restroom but returned quickly. During her absence I sent a text to my friend, Exa, to say Leah was hot. She drank her coffee through a straw, which I found endearing and little quirky.
Continuing with the small talk, I said, "So, you grew up in (the adjacent) county?" "Yeah," she replied, "and [the town where I grew up]." "Wow," I said, "where'd you go to high school?" She mentioned a rival high school. Interesting, I said, "you're from my town. I went to [my high school]." "Really?" she said, "and you're [my age]?" "Yeah," I said. "Well, you might actually know my mom, because she's the same age as you." I asked her last name, but she wouldn't tell me. She then said, "You're [my real name, first and last], right?"
I sat up straighter and narrowed my eyes a bit, looking at her face to see a resemblance to anyone I might know. It didn't fully register that she'd known my full name, but I was surprised. I thought about her actual first name. When it hit me -- when I'd put two and two together -- my hand shot to my face and covered my gaping mouth. My eyes shot wide open. "Oh, my God, I do know your mom! Is she [mom's maiden name]?" Leah shook her head in denial, but the facial resemblance totally gave her away. "Your name is [her full name], isn't it? I know it's true, because you look exactly like your mom." Leah admitted it was true, and we both sat there and stammered, stunned, not knowing what to do next.
I briefly entertained the idea of leaving right then and there. After all, I actually knew her mom. I told Leah that her mom and I been in classes together, and we'd had crushes on each other.
Her mom had the most amazing tits I'd ever seen, and I couldn't help but stare at them whenever I talked to her. One day, late in the school year, I went to talk to her and never even bothered to look at her face, and went straight to her tits. She wore a dark brown polo shirt, unbuttoned to her cleavage. When my eyes had found their target, I saw a tiny little sign sticking out from between her breasts. On the sign was written one little word: "hi." I looked up at her face and she was smiling her cute little smile. Mortified, I turned and walked away, but not before a guy behind her started cracking up, saying, "You are so caught! You're so busted!" This makes for such a poignant story for me, because I haven't changed one fucking bit! When Leah had earlier taken off her jacket, I caught a glimpse of her cleavage and smiled to myself, and thought, wow, I'm still doing this, just like I did with [Leah's mom]! And I hadn't even yet made the family connection!
Granted, I hadn't seen her mom in many years, but we had gotten reacquainted on social media, and we communicated with each other once or twice a month. She had divorced Leah's dad, a total asshole, a long time ago and had remarried. But he was a full-blood middle eastern guy. I now understood how I'd picked up on Leah's look right away.
Leah sat there, appearing to be fully composed, but then she said, "I really don't know what to do now. I got on the site thinking no one would ever know I was doing this, and here I am sitting with a high school friend of my mom's." (UPDATE: Having read this last sentence, it occurs to me that Leah absolutely knew who I was before she ever set foot in the door). We agreed that we'd have to process this huge surprise and really evaluate if we should just say goodbye and forget we'd ever met. I kept asking her how she felt about it, and she kept saying that she was processing it. She'd told me earlier that she'd found my pictures attractive, and now she was saying, "I think I'm even more attracted to you now knowing who you are." I couldn't lie to her; I found her unbelievably hot, and her being this woman's daughter just made her hotter to me. (What is it with me and ratcheting up the risk like this? Unprotected sex, public displays of affection, and now my friend's kid? Yikes.)
After a few minutes, we sort of calmed down and just started talking. Neither of us wanted any pressure, so we just moved past it. I reminisced about her mom, and her mom's best friend, to whom I'd lost my virginity. I also told her about one day when her mom, her friend, and I were at the friend's house enjoying the jacuzzi. I think we were about Leah's age at the time. After we got out and toweled off, we'd moved into the friends's bedroom and sat on the bed, just talking. I gave her mom a bit of a back rub, but nothing more. Her husband, Leah's dad, showed up about 15 minutes later, and when he saw the three of us emerging from the bedroom, I saw his face kind of fall and his demeanor immediately go from friendly to sullen. Apparently, he was not only an asshole, but a jealous asshole.
Most of the rest of our meeting is kind of a blur, because being in the coffee bar, it was actually a little difficult to talk about the arrangement stuff. I did, however, learn that Leah's last arrangement had lasted two years and was with a man her dad's age. I now understood her thing for older guys -- making things right with her asshole of a father). She also told me that her mom knew about her sugar activities. "She saw that I wasn't working, so she knew there must have been some way I was paying for school and my rent and my Audi. She thought I might actually be escorting, and she was relieved when I told her I just had one Sugar Daddy." No one else in her family knew.
After about 45 minutes, I decided that we needed to leave the coffee bar and start processing this meeting on our own time. She agreed and I walked her out to her car. When I got to her Audi (a white one, second time this week), we sort of grabbed each other and started kissing. A little at first, but she opened up her mouth and pulled me closer to her. It was so hot, but I suddenly became aware that I was in a public parking lot, kissing a young woman, wearing my wedding ring! Idiot! I broke free, kissed her cheek, and said I'd talk to her later.
After a few minutes in my car, I sent her a text: "I'm absolutely sure that I want you." Her reply: "I want you too." I called her and we chatted some more. Felt better to talk this way, safely in our cars with no prying eyes or ears around. It was clear, I told her, that the attraction between us was very strong, and she agreed. "I'm so attracted to you, Porter." I mentioned concern that I had about what would happen if things ended badly between us. "I mean, we both have a lot at stake, and we've been in these situations before, but let's remember that we're also human and not immune to making errors in judgment." She was puzzled that I was playing the end of things before they even began. "No, that's not what I'm doing," I said. "I'm just sharing with you what's in my head. In my gut, I believe we'd be discreet, safe, and mature about this. You're very mature for your age." "Actually," she said, "I'm three years older." "Huge relief!" I laughed. "Why did you lie about your age?" "Well, men like younger girls." "Listen," I started, "for a guy my age, a really young girl is just too fucking young!" I told her my rule about dating women at least Hayden's age. "So," I said, "should we give it a try? See how things work out? Maybe stay non-committal about it until we've satisfied our curiosity and checked what's in our guts?" "You mean, like, just one time?" "I dunno," I said, "maybe a couple, three times, and if things feel awkward and uncomfortable we can just say goodbye and good luck." We agreed that this would allow us to satisfy our attraction for one another and determine if we both possessed the maturity to hold things together.
So, dear readers, a WCSD Journal First! I am going to have a mutually beneficial arrangement with the daughter of a high school friend. I have no idea what I'm doing. I'm a little scared about it. I'm going to be very careful, but I'm absolutely going to fuck this beautiful woman.