“Did you go to Roosevelt?”
“Did you go to Beaverton High?” I shoot back, knowing damn well that he went to one of the many private schools for the rich. Could be Catholic. Could as easily be Jesuit or agnostic.
“Touché.” Drew sits back in his seat, teeth dragging across his bottom lip. Is this the part where I tell you that I wish those lips were dragging across my body right now? I wonder what he looks like without his shirt on. He keeps teasing me with those chest hairs, but is that all they are? A chesty tease? Or is he basically a giant hairy bear? I’ve been with both. I can deal with either. I definitely have my preference, though. Even if I decide to drag this man into my flurry of games, I would definitely give him some bonus points for being my exact type. “So you’re from North Portland. Yeah, I used to hang out around there a lot, too. Some of my buddies and I used to hang out in Cathedral Park after school. We’d cruise down Lombard.”
“You. Cathedral Park.” I can hardly imagine it. Especially when this guy would’ve been in high school. Cathedral Park is a nice place, especially if you live in the area. (Although you’re hard pressed to find a Portland park that isn’t filled with used needles and piles upon piles of garbage.) But it’s so far away from Beaverton, let alone far from the kind of place a young heir would hang out that I’m struggling to imagine a younger version of this man “cruising” down Lombard and drinking with his buddies inCathedral Park.
“Maybe I saw you around there,” he says with a generous sip of his wine. “We brought alotof girls through there.”
Is that supposed to impress me? I don’t want to hear about what a man-ho he is. I can see that for myself. Isn’t it so unbecoming for men to brag about how many girls they bagged as teenagers?
I’m not jealous. Why would I be jealous? Because so many women around here know what it’s like to be on the other end of his thrusts and I don’t? Yet.
Yet!I’m still thinking about it. Even if this doesn’t go anywhere, I might take him for a spin. Do you know how long it’s been since I had sex with a guy I’m actually into? I’m simply speaking physically. Let’s talk about true relationship compatibility.
“I think I would remember.” The cheese is almost gone. I had no idea I made such short work of it. God help me, am I eating without thinking? I only do that when I’m either so distracted that I need to put the chip bag down… or I’m off my game. And I meanoff my gameto the point I’m going home with a guy who has one over me. “I’ve heard of you, but before Friday night, we have never met.”
“You’re right. I would remember you, too.”
His wink is disgustingly diabolical. I might throw up. Then kiss him.
Usually, I know where I’m going with a potential mark halfway through our first real date. The end of our little meetup is where I either promise to call him again (and don’t) or I lay on the flirtationsextrathick, with the hopes of inspiring the man to whisk me away to a tropical island the next weekend. Or so he’ll attempt to promise me. Some of them only want to meet up at a hotel, or make a big showing of taking me up to Seattle. Classy guys suggest the opera for a second date, and that tells me they’re willing to spend some money on me – and I better make sure I’m worth spending money on, all right? New money men who come from lower class backgrounds love their lounges, pool halls, andhiking trips.Gag me with a spoon if I ever have to go on another hike on a second date. The guy has to be extraordinary for me to agree to that now. I can only hike through Multnomah Falls or Forest Park so many times before I’m bored to tears. And the weather! It can do anything!
Yet Drew is still a bit of a mystery. I don’t like that. I don’tlikemen I can’t read so easily I might as well be sifting through a slush pile. One minute this guy is trying to impress me with his money, and the next? Regaling me with tales of hanging out in Cathedral Park with his “buddies,” drinking cheap booze and hanging out with lower-class girls, like he’s one of them. I don’t doubt the veracity of his identity. I made sure of that before I came here, but guys who grew up like Drew either follow the Proper Trails blazed by their old money parents, or they rebel to the point of getting kicked out of the family. You don’t find many in between. Not around here. Your average rich upper-middle-classer often doesn’t understand they’re middle-class in Portland. Not when property values are so high that your two million dollars buys you a five-bedroom house in a “nice” neighborhood and not much else. The Bentons are worth a billion dollars, though. Maybe more, since God knows they’re not advertising the off-shore accounts and money pumped into whatever investment is lasting the longest these days. I don’t know how much of that Drew will have one day, but he’s both acting like he’s entitled to it… and that he never expects to get it.
Right now, my only motive for dating him is purely personal. He’s hot. He has a nice car. He knows how to blend into my kind of scenery. He’sapparentlygot a big dick. All things I can take advantage of for a while. Yet will it do me any good to have a “real” boyfriend if I can’t play him like the violin I pretend isn’t a fiddle?
It’s time for a test.
“Excuse me,” I say, picking up my purse. “I need to use the restroom.” It’s partially true. I haven’t “gone” in about two hours, and I’ve been drinking wine. A little tinkle is on the docket.
It’s also the perfect excuse to see how he reacts to a few things.
Let’s start with how I get up and sashay – yes,sashay– toward the ladies’ room. These heels do amazing things for my legs. Behold as my ass hypnotically swishes my baggy pant legs. This jumper may not show off my thighs, but Drew is getting an eyeful of promises, promises,promises.I toss my hair behind my shoulder, exposing the white of my throat as I pretend to be checking my phone. I catch a glance of his face before I turn the corner. Sure enough, he’s watching after me, lust attracting the attention of every other woman in this room.
Oh, good. We’ve established that he still wants to fuck me. Now, let’s wait agoodten minutes to see how he feels when I come back out fixing my bra and smelling like my floral hand lotion.
Either he’ll be so famished for my presence that he chokes on his own spit to see me reemerge, or his boredom will be as plain as day because I’ve made him wait so long. At least then I’ll have an idea toward whether I should go for a second date. I don’t have time for men who mess with my head and are bored with me. If I decide to pursue Drew Benton because he tickles my fancy – instead of my wallet – then I better feel like it’s worth it. I could be giving up other prospects to spend some time with him.
Although I’m sure that time would be… well, you get the idea. We would be busy.
He’s writing something in a palm-size notebook when I reemerge from the women’s restroom. I smell like flowers and walk like I’ve dispatched a giant weight. (He’s not disgusted by a woman’s natural body functions, is he? Let’s find out.) When I sit down, he kindly looks up and puts the notebook and pen away. I’m greeted with a friendly smile. He’s put out that I took so long, but he doesn’t say anything. Nor does he act like he’s been setting up a date with another woman.
“I’m sorry I took so long,” I say. “There was an important phone call while I was in the other room, and…”
“No worries.”
No worries, hm? Who was worrying? Him? Me? The poor server who keeps looking at him like she’d want to eat him for dinner? Or that obviously gay guy on the other side of the room who isalsolooking at Drew like he’d eat him for dinner? Don’t think I don’t know I could be the one with the honors tonight. I bet if I performed a trick with a cube of cheese he’d be begging me to go home with him. Think I’ll keep him waiting. Make him think about thepotentialof Cher, the perfect girlfriend. That will give me more time to figure out who his perfect girlfriend is.
Does he want a girlfriend who “isn’t like the others?” One who has a blowjob ready for him every day? One who happens to hate being eaten out, whoopie for him? How about a girlfriend who works for her own money, or one that wants to be babied all day? A cultured woman he can take anywhere without fear of her embarrassing him around the locals? Or a girl who will act like Montreal is the most foreign place on Earth? Maybe he wants a woman who reads Chaucer and Psychology Today. We’ll discuss the latest research into global warming over Thai at the corner restaurant. Or I’ll let him be the smartest man in the room. One who can lecture me about whatever strikes his fancy. Whatever he wants to talk about, I’ll be completely ignorant toward. That’s the beauty of being a chameleon who is only in it for the benefits and not for love. I can be anyone. I can be anything.I’ll be his personal blowup doll if it means a million dollars to my name by the end of the year. Why, yes, Drew, youcanstick your big dick in my ass on the first date! I really don’t know why other girls say no. Come on my face? Choke me a little? Handcuff me, though I barely know you? Oh, those other girls areso prudish,aren’t they? I would love to play out your porn fantasies! Because I’m a cool girl. I get that your addiction and misconceptions about real sex are a silly thing to think about. We can have all the threesomes with other girls that you want. Why, I wouldloveto finger another hot girl if that gets your wallet out.
What, are you sickened? Appalled? Do you think I’m “nothing but a slut” now? You haven’t been paying very good attention if you’re only now starting to get it.
Because I get it.
Drew Benton wants acoolgirlfriend. One who turns her nose up to other women who totally aren’t like her. Because I understand his love of beer, video games, cars, and porn. All his jokes are hilarious, and all the ones I make are at the expense of my womanhood and intelligence. I’ll play his game of “dibs” whenever we’re surrounded by other women.“Oh, Drew, I would love to claim that one, if you don’t mind.”I’m bisexual when it comes to threesomes and super straight when it comes to his dick. Igetit, don’t you see?
Hmph. No. Neither do I. Guys looking for a “cool” girlfriend are often the most disingenuous and sometimes the most dangerous to get into bed with, but I know how to play it well. One might say it’s my most natural inclination. Geez, says a lot about my own dating history and how I ended up here today.