Chapter Seven — Callum
I have to say, I’m slightly disappointed. I expected more from Lola. I don’t know why, but I got a good vibe about her.
But when I met her in person, it was impossible to get a read on her. It seemed like I was walking into a fortress. She had a poker face on during the entire chess game and waited an extremely long time between moves.
The moves she made were good, but then again, I’d expect anybody above an ultra-beginner level to have been able to make them. Given how poorly I played, I basically dictated her moves.
So I couldn’t really get a read on her ability. The fact that she paused so long between turns, though, makes me think that she was either wrestling with self-doubt or just pretty inexperienced with chess. Which is fine, by the way. I’m used to that. I wouldn’t expect a woman to be good at chess.
I know, I know — that’s misogynistic of me. But what can I say? That’s been my experience. Still, I love it when a woman surprises me, and I guess deep down, part of me was hoping Lola would. But so far, she hasn’t.
I mean, she’s breathtakingly beautiful, which I already expected from the pictures she submitted on my website. Her answers to all the questions on my website were cryptic, which also got my hopes up. I love a good mystery.
What do you hope to get out of this? “A million dollars” was her answer. I can’t fault her for that. It makes sense. But it gives me no additional information about her: who she is, what motivates her, what her deepest desires are etc. Which made me even more curious.
And then there was her answer to the question: How would you describe your sexuality?
“Pass” she wrote. That intrigued me even more. I don’t think a woman’s ever written “Pass” on any question.
Pass. Is she shy? Nervous?
I have to say, I love shy girls. I love shining the spotlight on them and watching them squirm as they’re pushed outside of their comfort zone.
I love making them do things they’ve only dreamed about.
It’s probably the thing that turns me on more than anything, which is why I run these games in the first place.
Everyone thought it was insane when I told them. Granted, I haven’t told many people — only a few very close friends… friends who are as fucked up as I am.
And there aren’t too many of those.
My friends in healthy, loving marriages, who have vanilla sex with their wives twice a week …
well let’s just say I stick to talking about golf and stocks with them.
The friends I talk to about this kind of stuff are the friends who either dabble in other risky behaviors or are degenerates like me.
Even my craziest friend, one who had a stint as an adult actor, thought this was insane.
“You’re gonna give away a million dollars?” he asked me when I told him.
I remember shaking my head at him and laughing. “No.”
“But you’re promising —”
“If the girl wins, I give her a million dollars,” I said. “Emphasis on the if. But they never will win.”
“How do you know?”
“Trust me. I went to law school, remember? I wrote an ironclad contract here.”
Of course, what I failed to tell my friend — or the girls — is that a contract like this would probably be voided in court. These aren’t the kinds of things you can negotiate on and be held to, legally speaking. But the girls don’t know that.
And besides, how humiliating would it be for them to go up in front of a court or a judge and say, Your Honor, this man enticed me, promised me a million dollars if I submitted to his sexual games, fantasies, and punishments.
But one of the punishments was too much, so I opted out.
It’s unfair, and I would like him to compensate me.
No sane girl would ever do that. I doubt an insane one would either, to be honest.
I, on the other hand, would be willing to go up in court and defend myself. I’m shameless like that, and the girls all come to find that out very quickly. It doesn’t take long for them to realize that if they ever try to call my bluff, they’ll lose.
And besides, in the worst-case scenario, if a girl did somehow miraculously win, I could fork over a million dollars. It wouldn’t even mean that much to me. It would hurt a little bit, but it would mostly hurt my pride.
And that’s good. In fact, I want it to hurt a little.
I tossed around the idea of making the stakes less, 100k, something I wouldn’t bat an eye at losing.
But that didn’t feel exciting. I realized that I need to make the stakes high enough so that it feels important to me, like I could really lose something.
If I don’t, then it just becomes like another pointless game, like a game of strip poker.
And sure, strip poker might have been fun when I was sixteen, but as I’ve gotten older, the things that used to do it for me just don’t anymore.
So I’ve had to find ways to keep upping the stakes.
So here I am, at thirty-six years old, only fucking women who are willing to submit to the sick little games I like to play. It’s twisted. I know that.
And that’s why I like it, obviously.
And why I made the stakes at a million dollars.
It attracts a certain kind of woman. I know that. And I’m not quite sure if that’s a feature or a bug yet.
On one hand, it attracts a crazy kind of woman. Which is good in a way, because I like chaos. It’s fun, although it gets tiring after a while.
Deep down, though, I think I’ve always hoped that one day it would attract a smart woman. A woman who could actually challenge me. A woman who could give me a real run for my money. A woman who might actually win.
Of course, that’s never happened. Maybe that was a pipe dream to begin with. But still, a man has to have something to look forward to, some type of dream — no matter how far-fetched, right?
And maybe that’s why I’m slightly disappointed with Lola.
Because for some reason, there was something about her that made me think she might be that girl.
The girl that gave me a run for my money.
But I’m doubting that, now. The way she hesitated during our chess game told me she had no idea what she was doing.
Either that, or she was taking it extremely seriously. But I doubt that.
Unfortunately, her texts have only confirmed my hypothesis.
Namely, that she’s an idiot. I’ve noticed multiple misspellings and grammatical errors.
I’m tempted to scroll back to our earlier messages, because I swear she wasn’t always this inarticulate, but the earlier messages have been automatically deleted, as every text message of mine is after twenty-four hours.
It’s times like this that I wish I wasn’t such a hawk about security and privacy. Then again, you can’t blame me when I’ve basically made my entire fortune through online privacy.
I started a cybersecurity company ten years ago and grew it into a multi-million-dollar company. I sold it for fifty million just last year. It’s hard to stop caring about security when it was basically your entire life for a decade.
My phone buzzes and I look down. It’s another text from her.
I’ve never played. Can u teach me?
I can’t help but notice that she spelled “you” as the letter u. I try not to judge, but I feel a small flash of contempt as I read the message.
Idiot, I think to myself as I scroll up to our earlier messages.
How about poker? my last text had said. I’d asked Lola what she would like for our second game. It’s what I always do. I recycle the same moves for most women. Lose the first game to get their confidence up. Let them pick the second game. Rinse and repeat.
Letting the girl pick the second game gives them a false sense of control.
It gives them the illusion that they could win.
I say “illusion” because I make sure I always win the second game.
On the off chance the girl picks a game I’m bad at, I’ll gently steer them her in another direction.
I think that’s only happened once or twice, though, because it’s rare for a girl to pick something she could actually beat me in.
So, I let the girl pick. Then, when I beat her at the game of her choosing, it throws her off balance.
Since she chose the game, she feels like she has the upper hand.
Then I snatch that away. In the few years that I’ve been doing this now, there’s only been one occasion where I turned down a girl’s request.
In that case, the girl suggested some kind of acrobatic competition, and she was a professional circus performer. Despite being quite athletic and quite flexible for a man my age, that’s not something I could compete with.
I suggested something more benign — either a 5K race or a handstand competition, I can’t quite remember. In either case, I won. As always. In fact, I’ve never lost the second competition. Not once against the twenty-nine girls I’ve done this with.
And I don’t plan for Lola to be the first. Although she has been the first so far who hasn’t even suggested something for the second game. She just threw the ball back at me.
I was distracted at the time, so I responded with the first thing I thought of: poker. Poker is also something I happen to be extremely good at, which is usually why I save it for later games — in the rare chance that I need to lock in some wins and scare the girl away.
But Lola doesn’t seem like she’ll be much of a challenge anyway, so who cares if I blow one of my easy games early?
One of my self-imposed rules, which is also articulated in the contract, is that each game can only be played once.
Without this rule, I could just play one game I like seven times, indefinitely, until the girl capitulates.
Which would strike the women as unfair.
Of course, they’re going to lose eventually. But they can’t know that. It would take away the fun if they thought there was no way they could win. If the women knew that there wasn’t a snowball’s chance in hell they could win, a lot of them wouldn’t even bother playing in the first place.
So I have to create the illusion of fairness, the possibility that they could win. It’s like the lottery: everyone knows you’re not really going to win, but theoretically, you could.
And that’s enough. As long as the hope is alive, that’s good enough.
Same with my games. I think most women knew, if they were being honest with themselves, that they weren’t going to win. But they need an excuse, plausible deniability, to engage in this crazy contract.
And my rules, combined with the bait of a million dollars, gives them that. And so we both get what we want: I get to humiliate them and use them, and they get to be humiliated and used under the guise of trying to make a million dollars.
If anybody questions them, or if they question themselves, they can point to the money. They don’t need to look inwards. They don’t need to excavate their own sick and twisted desires. They can just point at the money and wave away the cognitive dissonance like a pesky fly.
If only it were that easy for me.
All that said, I have these elaborate rules because I have to make things seem fair.
And on the surface, they are fair.
Under the surface? Not so much.
What’s really unfair, though, is that I’m just much better than most women at almost everything. I’m better than most men, too.
I also know how to push women to their limits. Half of this is about winning games. The other—and I would argue more important—half is about imposing escalating consequences. Consequences that become so harsh that the woman voluntarily quit.
There’s a skill to imposing these consequences. I don’t want the women to quit right away, because then I wouldn’t get to have any fun. I like to watch the women squirm. And the longer they squirm, the better.
In fact, it’s good when the women like the consequences at first. They’d never admit it, but that’s the ideal scenario.
I want the women to feel excited, like I might be their Prince Charming — their Fifty Shades of Grey version, at least. But then I keep ratcheting the pressure up, and, like a frog in boiling water, until eventually, they succumb.
At that point, the women realize that I’m too much for them, that what I want — my desires — can never be satiated.
Further, they realize they’ll never win, and I’ll never let them win.
And given my capacity for cruelness, which I slowly reveal to them over time, they realize they’ll never change me.
Despite the fact that many of them will fall in love with me at some point, they’ll all give in eventually.
They’ll realize it’s futile, that trying to change me, trying to soften me, trying to win me over will only make me want to punish them harder.
And many of them will say they can take it. They can take the punishment. They’ll lie to themselves and to me. But eventually, even the strongest among them will fall. Because everyone has a limit, and I’m prepared to push them to it.
Maybe that’s why I don’t respect most women — because I’ve seen too many of them fail. Maybe that’s on me, because I select women who fail. But I don’t know. I don’t think there are any women who wouldn’t fail. I’ve been waiting for one, and so far, no one’s even come close.
I look down at my phone. Oh well, I think to myself, remembering Lola’s shiny brown hair and soft skin. I remember the way those pretty hazel eyes of hers opened when she met me, eyelashes fluttering.
At the very least, it’ll be fun to break down another pretty girl. Sure, it won’t be interesting or particularly novel, but fun all the same.
Of course I’ll teach you, sweetheart, I text back. Saturday 1 p.m.
Barely thirty seconds pass before my phone buzzes.
Im in.
I can’t help but notice the lack of apostrophe. I heart the message and shut my phone, then close my eyes and plumb the recesses of my mind for the memory of the last girl I destroyed.