Barely Paralegal – Chap 1 by story442

It was the middle of my second week of work, and I think Linda was out running some errands or something, so it was just the two of us down in the basement. Mark and I were getting a fair amount of work done, but still shooting the shit like usual. But this afternoon, Mark decided to bring up a subject we hadn’t discussed before.

“So did you date a lot in high school?” he asks me.

First off, it’s weird hearing him refer to my high school experience in the past tense, but I guess that’s because the fact that I graduated still hasn’t sunk in yet.

“No, not really.” I answer him pretty generically, when really the most accurate answer would’ve been “not at all”.

“So are you a virgin?” Mark follows up with, clearly escalating this conversation rather quickly. To be honest, even in just the week plus of working for him, he’s had such a comfortable and honest way of chatting, that this extremely personal question doesn’t seem weird or even unexpected.

“Yeah, I am.” I answer. And then I figure I might as well save us both from the subsequent follow up questions, so I add, “I haven’t even kissed anyone yet.”

After saying this, I’m thinking holy shit, that’s not even something I’m comfortable saying out loud to my closest friends, even though they probably could guess at my total inexperience when it comes to girls. But here I am just admitting it to my dad’s friend, who’s also my boss? How weird is that.

“Don’t sweat that at all.” Mark says reassuringly. “Hell, I didn’t even have my first kiss until I was 19. Sophomore year of college. In fact I must’ve been almost 20 by then too, so I hope that’s not something you ever stress about, because you shouldn’t.”

To be honest, it WAS something I’m embarrassed about. I’m extremely curious about sex, as I’m sure most 18-year-old guys are. I definitely have watched my fair share of internet porn, and I want so badly to try all the different things I’ve seen in those videos, but at the same time I also know that eventually my time will come. Or at least that’s what I keep telling myself, to prevent me from getting too down about it. But suffice to say, it’s hard to imagine any 18-year-old, sexually active or not, who thinks about sex and the female anatomy more than I do.

Mark then looks at me and says, “I’m actually surprised. You’re not a bad looking kid. And I can tell you’re in great shape, that’s from running right? Aren’t you on the track team?”

“Yeah.” I answer. “Well, cross country actually. But close enough.”

It was certainly nice of Mark to feign surprise that I’m not currently attracting any attention from my female classmates, but I think he was being overly generous. While I technically am in good shape, I think the most appropriate term to describe my body would scrawny. Or maybe lanky. I’m 6’2″ and weigh 150 lbs, so you can do the math. I’ve always been self-conscious about being so skinny, and it even got to the point where I tried a daily protein shake regimen. But that didn’t work, as it just seems like no matter how much I eat or drink, I can’t ever build any muscle beyond my current frame.

Other than my skinny body, I guess I’m a decent looking guy. I keep my hair pretty short, and I try to dress nicely. But for whatever reason, I’ve never heard of or known of a single girl being interested in me. Just once, even if it was someone I wasn’t attracted to in the least, I’d love to hear that someone else had a crush on ME. It’d be such a cool feeling and confidence booster that maybe it would be the perfect catalyst to break the ice and lead me towards actually having a dating life.

But anyway, back to Mark and asking me about my sexual history. It was nice to hear that he too was a late bloomer and that it wasn’t THAT unusual for someone to reach their late teen years without so much as a kiss. Mark himself seemed like he was pretty well put together. He looked like he worked out a decent amount, even though he had kind of a large pot belly. In fact, he weirdly looked like he was both in shape and slightly overweight, all at the same time, if that makes any sense. He was completely bald, but had a well trimmed goatee. Overall, he and Linda seemed like a good match appearance wise, and they made a nice couple.

After giving me those initial complements about my own appearance, Mark then looks at me for a few seconds while appearing to contemplate what to say next. Then he finally says, “Let me give you two pieces of dating advice.”

I’m really interested in what he’s going to say here, as even in the short amount of time we’ve hung out, I’ve already built up quite a level of respect for him and his take on life.

“First off, don’t ever date someone because you think it’s who you’re supposed to date. Date the person that deep down you WANT to be with, no matter who that is.” Mark says this, but I don’t really get what he’s getting at. And then he continues, “The classic example is Prince Charles. Everyone else wanted him to be with Princess Di, but deep down he always loved that Camilla Parker Bowles lady. So what did he do? He married Diana. And they were both miserable.”

Now I’m completely lost. I’ve heard of Princess Di before, but all I really know about her is that she died young. And I know Prince Charles is Prince William and Harry’s father, but that’s about as far as my royal family knowledge goes. I guess I get the gist of what he’s trying to say though, in that you shouldn’t care what other people think of who you want to be with. I certainly wouldn’t argue with that idea, so I casually respond by nodding my head and saying, “That makes sense.”

And then Mark continues on, “And secondly… you should find someone who you can bare your entire soul to. And what I mean by that is, someone who you never have to filter who you are. Someone who you can truly be authentic with.”

That idea also makes sense, but it kind of seems similar to the first. Basically, I get the impression that he was telling me not to settle and to find my soul mate. I was kind of expecting something more specific when he prefaced his two main pieces of dating advice, but what do I know?

But Mark wasn’t done on this second topic of being able to bare his soul. In fact, this is the point where he takes the conversation into a pretty eye-opening new direction. Mark tells me, “Let me give you an example of what I mean about having no filter with the Misses. It was probably around 10 years ago… I was either in my late 30s or maybe early 40s, but regardless it was awhile ago. But we also had been married for awhile at this point.” Mark then noticeably pauses and takes a breath before continuing, “Linda was a little drunk one night, and we’re lying in bed, and she asks me… what’s my biggest fantasy? She says this totally out of the blue with no context.”

Ok, this is pretty interesting I’m thinking. He certainly has my full attention now.

Mark then continues, “Now we’ve always had a pretty decent sex life, and could talk about sex, but this question was still unusual for her to ask. Now, as decent as our communication was, there were still any number of things that I wasn’t quite comfortable sharing with Linda, even though she was my wife!”

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