My Day With Bree Olson.

Bree Olson
When I was in junior high, I had a Social Studies teacher who was a total hippy. He’d play records on one of those small turntables you’d get from the school’s A/V department, while we were working on whatever it was we were working on that day. One of his favorite records was “The Worst of Jefferson Airplane”, and I’d always wonder why anyone would name anything “The Worst of”…until now.

With all the Charlie Sheen hoopla right now, I thought I’d pull out some of my old Bree Olson posts. I dunno if you’ve seen Sheen’s twitter, but he just posted a pic of himself with “Rachel”…as apparently Bree has retired.

For now, anyway.

I’ve got some more Bree blogs laying around, and since I’ve had absolutely nothing to say in a long time, I’ll just go ahead and post some “worst of’s” featuring Bree and the teeny tiny bit of time I spent with her.

This blog’s original air date: October 4, 2006.

I had the day off today, so I decided to hang out with my old pal, Jimmy Hat. Jimmy invited me over to his studio to watch him shoot a brand new hottie named Bree Olson. So I made my way through Friday traffic on the 101, straight outta K Town and out to the middle of Porn Valley.

Fuck, Bree Olson is fuckin’ smoking hot.

What else can I say? That she got off the plane from the Midwest only hours before getting to Jimmy’s studio? That she’s still a teenager? That she’s only done a handful of scenes? That’s she’s a college frosh? Or maybe that, 1/2 way through her soft core solo stills, Bree was so excited about posing nude in front of two strangers that her pussy was dripping wet?


I shit you not. I don’t think I’ve ever seen a pussy drip like Bree’s. I think the only sexual cliche more abused than penis size (oh yea baby…mine’s at least 8 and 1/2 inches) is the dripping wet pussy.

Not too many 8 and 1/2 inch dicks out there (fact dick fact: 1 in 10,000 men have a penis bigger than 7 inches); and there’s not too many dripping wet pussies out in the real world, either.

Bree’s pussy was dripping wet. And it ran down her V-Jay, right into the crack of her butt, and then…on to the sofa.

That kind of dripping wet.

Oh, but it didn’t end there. Turns out Bree likes her men to be “in charge”, which perked up my ears. “What do you mean by being in charge?” I asked.

“Oh, you know. I like to be put in my place. I’m very submissive. I even like it when I’m having sex with a guy and he chokes me out.”

Out of nowhere Bree makes that kinda statement.

Out of nowhere.

Now, I’m not too much of an A Dog. Really, I’m not. Which is to say I can be an A Dog, and I can be a B Dog in my relationships with women. So I don’t know what got into me right then and there. I love women. Really, I do. I love everything about them. I love the way they smell, and the way they look, and the way they laugh, and the way they feel…but suddenly I was standing right next to Bree – my hand around her neck, slowly applying the pressure – just cause it was Friday, and I didn’t have to work, and Bree said she liked getting choked out by an assertive, aggressive guy, and did I mention that Bree is fucking hot?

So why not be that assertive, aggressive guy? At least for today?

What do you think she did? Did Bree pull away? Did Bree hit me? Or grab my hands? Or ask me to stop?

Her legs quivered, and her voice had that nervous jitter in it…the kind most of us get when we’re so totally turned on our voice jitters in that nervous, excited way.

Honestly – look at me. I’m a middle-aged chubby dude who likes to wear flannel PJ’s way too much. Am I really the kind of guy that would actually turn on a teenage hottie like Bree? Fuck no…and I don’t even have to answer that, do I? But there’s Bree – melting in my grip – and suddenly she’s got her hand on my dick, and she’s rubbing it, and she’s whispering things like oh God and I’m such a dirty whore.

I’m such a dirty whore.

With the quivering, jittery voice.

While her barely-legal hand is rubbing my dick. The same hand that would have landed me in the joint if we were engaged in this sort of activity just a year earlier.

What’s better? This, or, say…the winning lotto ticket? Well, the lotto ticket for sure, unless it’s just the 5 out of 6 winning lotto numbers for, like, 10 grand. Then I might take the pussy-drippin’ teenage whore who’s rubbing my dick while whispering filthy, nasty things in my ear. With a nervous, jittery voice.

Yes, I think it’s safe to say that at this particular junction of my life I would take that to a 10 thousand dollar pay day.

But it gets better. Just let me know when I should stop…cause I’m afraid today’s entry is going to turn into more of a bullshit egotistical act of bravado than a simple story, and no one likes a cocky piece of shit, do they?

I dragged Bree around that apartment by her hair. I made her perform oral delights. I choked her till her eyes rolled into the back of her head. I bent her over the sink and stuck my wee-wee in her, then I pulled it out and dropped her back to her knees, just so she could taste her own delightful juices off it.

Then, I’d make her beg for another round.

And beg she did, while loving every minute of it.

Jimmy H. did not. He was trying to work, and of course I didn’t act like this from the time of her startling admission till the end of the day. I’d be all sneaky about it. Jimmy would finish a set, and send her into the dressing room to change, and I’d follow her in – all creepy and weird – and she’d giggle and then I’d wipe that giggle off her face with a choke session and that’s when she’d moan and her legs would quiver.

Really loud moans. Really shaky quivers.


She’d whisper in my ear, “he’s mad,” and I’d whisper back things like “so what”, which made her quiver some more.



I’m done. Really, I am. Enough of all this silly bullshit. I’m embarrassing myself now. Anyway, after we wrapped I took Bree out to dinner, and on the way I apologized for my behavior, and said things like “that’s not really me” and she’d laugh and say “but I liked it, I really did,” and right then and there she told me she’s even had guys go pee right in her mouth.

That’s right — in her cute, barely-legal mouth.

I forget to ask if she drank it, or if it simply just ran down her cheeks. And suddenly, at that point – right after she’d admitted to being a human toilet – I didn’t feel bad for dragging Bree around by her hair and making her say and do naughty things.

At dinner she told me about her boyfriend. She found him on mySpace, and she searched specifically for dudes in her area that made more that 250K a year. I had no idea mySpace offered such a wonderful service as allowing a user to find their ideal mate by an income tax bracket, but apparently they do. Bree found one man in her small, Midwestern town that fit the bill, and sure enough they’re dating, and sure enough he’s fallen in love, and sure enough she’s ready for more, and sure enough when she’s done with school she’ll divorce him, and take 1/2 of his stuff, cause that’s her plan.

She didn’t mince words, either.

“Why would you do that to him, Bree?”

“Cause I want nice things while I’m in school. Like a Mercedes.”

“What kind of Mercedes?”

“Oh, any kind. I don’t care.”

“How about you live in a dorm room and have a roomie and eat Top Ramen and be poor and enjoy your time being a young starving student so you’ll enjoy things even more when you earn them, later in life, yourself?”

“You’re a pornographer. You’re no better than me.”

“But I don’t deceive people. I mean you know exactly what you’re getting yourself into when you come spend a day with me. What if this guy walks off a bridge after you divorce him cause he loved you so much? What then? I mean how would you feel?”

“He won’t do that. And if he did I’d go to his funeral with some flowers. Besides, it’s not like it hasn’t happened to him before. He’s already been divorced once.”

“Well, just be honest with him. Tell him you want a Sugar Daddy. If he dumps you, trust me, you’ll find a guy that’ll be happy to be your Sugar Daddy. You know? And then you can live with yourself cause it’s the right thing to do.”

Bree looked at me for a long second, and then down at her food. Like most of the porno chicks I’ve had dinner with, she really didn’t eat a thing. “Hey, what are these little green thingys in my food?”

“Those are called capers.”

“Well, I don’t like them. Capers ruined my meal.”

William T. Vollmann once wrote that prostitution is the most honest form of love. I used to think Bill was a hateful dude who holed himself into fleabag hotels and wrote endless novels cause that’s about all he could ever do: hate and write. And as I walked Bree out to my car, the only thing I kinda wished I woulda done earlier that day is make a Number 1 in her mouth, too.

8 thoughts on “My Day With Bree Olson.”

  1. Quite sad that today’s youth think that wealth = income. People with real money (old money) don’t even care about income, and wouldn’t even have it listed on Myspace.

  2. @Mark G –

    Old money wouldn’t bother to have a myspace (or any other kind of social media) page at all.

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