F*cking a Dad of 8 Who Lost His Millions, Got Fat, and Can’t Look Women in the Eye… and It Was Damn Good Sex

He’s your typical Marin type: a hedge fund veteran with two ex-wives, a couple of $10 million properties, and a stiff, arthritic body that barely moves. But somehow, we still managed to fuck for hours. Now in his 60s, he’s still neck-deep in CEO deals, juggling three mortgages, and supporting eight kids with lavish North Beach lifestyles — the kind of pressure where he’s probably taking a hit of cocaine every day just to keep up with these little bloodsuckers.

Now he’s the kind of guy who’s been beaten down by life but still shows up. And for some reason, he thought it would be a good idea to show up for me.

I meet him at this shithole Thai place in Marin. We have a glass of wine, and right off the bat, he’s self-deprecating as hell. “I can’t believe someone as famous as you would show up for a date with a guy like me.” I had to laugh. I don’t think of myself as famous — I mean, I work hard at what I do, sure, but that’s just a label people stick on.

If I’m being honest, I had been working myself up into a fantasy about Santa Claus for two weeks after I walked through Target and saw the Christmas decorations starting to creep in. I’d sit there in my twin bed, playing with myself for hours, just imagining what it’d be like to get fucked by Santa Claus.

So, when this guy slid into my DMs a few weeks earlier, I thought, “Yeah, he knows who I am, but let’s play it cool.” I’m the best brainwasher on the planet, but I don’t need to reveal all that upfront. So I ask him, “What do you do?” and he gives me the usual, “I’m an investor for blah blah blah.” I nod, pretending to be impressed, but really, I’m just thinking about how this whole thing is going to play out.

And then I ask him, straight-faced: “Cool. But can you still get a hard on?”

Anyway, I’m thinking this guy’s probably racked up so many DUIs that he can’t drive anymore — he’s got a car service to take him everywhere. Happens a lot with these older guys.

We get to his massive house, and it’s practically empty — barely any furniture anywhere.

This is what two ex-wives can do to you — leave a once filthy rich investor with nothing but a bare mattress on the floor. Ivy League-educated, a top dog on Wall Street back in the ’80s and ’90s, the guy was on TV all the time, talking money and making deals. And now? Just a mattress on the floor.

I slip off my jeans, peel off my top, and my tits bounce as I stand there, already wet and aching. All I can think about is fucking this old man senseless.

Come on, play with your dick, get it nice and hard for me. Real hard. And, can you believe it? This guy actually got rock hard.

And I’m playing with it, and he looks a little like Santa, a lot like Santa okay. I’m closing my eyes and I’m thinking of Santa sliding down the Chimney, coming into my bed, and playing with me.

I’m stroking his cock, and I can’t help but notice — he looks a little like Santa. it’s a fantasy I’ve been craving for ages. He’s got his hands on my tits, his tongue teasing my ass, and I can’t take it anymore.

“Say it,” I whisper, grabbing his cheeks and holding them tight. “Say ‘ho ho ho’ while you fuck me. I want to feel your cock deep inside me as you say it. Say it.”

And just like that, he starts groaning, and as he’s thrusting, he lets out a breathless, “Ho ho ho,” right before he cums deep inside me.

I drift off to sleep, and soon he’s snoring beside me, the room filled with that low, rhythmic sound. When I wake up, he’s already stirring, full of this weird burst of energy. “I’ll make you coffee,” he says, like everything’s perfectly normal. So he heads to the kitchen, whistling like he’s hosting brunch instead of waking up from a night of wild, sweaty sex.

We sit down with our mugs, and out of nowhere, he says, “I’ll probably never see you again, will I?”

This man was genuinely sad, almost desperate. “Look, you can come over anytime,” he said, his voice soft and pleading. “This can be your house too. I’ll do anything you want — I’ll put a hot tub in the backyard, I’ll stock the fridge with all your favorite foods. I think I’m kind of in love with you already.”

I just sat there, thinking, I literally just met you. And yet, here he was, pouring his heart out, confessing this weird, sudden infatuation.

And all I could think was, damn it. This goddamn Santa Claus fetish of mine.

I smiled politely and said, “You know, this isn’t going to work the way you want. I’m a brainwasher, and brainwashers don’t do the whole marriage or boyfriend thing.”