June 6th, Las Vegas: I wake up in the Vegas house and immediately feel like I ate too much Korean food last night. I’m going to Los Angeles today for the Playboy mansion party, and I am told we should be dressing in all black. Apparently the kid coming with me, Andrew, has booked a hotel room with two beds and since I plan on leaving the next day I don’t even bother packing anything besides my laptop. I throw on my dark grey suit, my black shirt with French cuffs, then eat breakfast and call a cab.
I take a ride into the Strip and get dropped off at the Forum Shops at Caesar’s. I walk outside the hotel and see a cute brown haired girl walking my way with her friend. As she walks by me I tap her on the shoulder and say
“Hi, I know this is very forward of me but I saw you as I was walking down the strip and thought you were really cute and wanted to stop and say hi.”
Both girls immediately react very positively and we start talking about what they’re doing in Vegas, what I’m doing in Vegas, and how the hell it is I’m going to the Playboy mansion in Los Angeles tonight. I tell them I’ll be back tomorrow and ask what they’re doing that day
“Hanging out with you!” says the brunette, whose name is Gina (name changed.) I tell them to put their number in my phone and the friend quickly pulls out her card and tells me to add the cell number on there and that that’ll reach both of them. I add it and call her so she has my number, then I excuse myself and keep walking.
I walk over to the Fashion Show Mall across from Treasure Island and take a brief walk around. I go into Saks Fifth Avenue where I am greeted by Martin, who I’ve gone through for clothes in previous years and still remembers me. They are having a sale on suits and we start looking around for something black with pinstripes. We find the perfect one and he tells me we’ll do the alterations today but he won’t put the sale through until tomorrow when it goes further on mark down. I also pick out a couple of ties, including a dark one to go with my suit for the evening. I ask him to show me how to do the double Windsor knot because mine is rusty. He teaches me to tie one very well.
I take a cab over to the airport. I have no luggage to check in so I’m through security very quickly. I buy a copy of GQ at the magazine store and during my flight and learn that Christian Bale will always come off super intense in an interview even when he clearly wants not to.
We arrive without incident in Los Angeles and I walk out of the airport without having to worry about baggage claim. I take the $60 cab ride to the Roosevelt hotel in Hollywood. I guess people weren’t lying about this place being totally sprawled out. In the lobby I ask for the room of Andrew Voshage, the kid who won the contest run by www.rakebacknation.com to get the other ticket on the trip with me. Andrew comes down stairs and we hit it off immediately; he’s just a super chill and normal Midwest guy who is real easy to kick it with. We put my bag in his room and I find out there is only the single bed. Meh, I’ll just try very hard to wind up in someone else’s.
We go downstairs to the café to get some food. A guy Andrew met in his previous days in LA calls and tells him they’re going to meet us. Andrew warns me that the guy he’ll be bringing with him is the single biggest douchebag in the world. I don’t fully comprehend what he means by that until the two guys show up. The douchebag in question (I think his name was Brad?) is a very out of shape man in his late 30’s with a face that is comfortably less than chiseled. I attempt to be polite and nice and he is immediately casually condescending. This leads into constant bragging. At his pinnacle he reaches down and pulls out his iphone, which contains a picture of a hot blonde girl
“See her” he says “I kicked her out of bed on Thursday, ya know? She’ll be coming back for more though…”
He trails off for a moment and lowers his iphone
“Because she wants a ride in the car!” then raises his iphone again to show me a picture of a silver Ferrari. He is 100% serious about all of this. I am flabbergasted at the lack of social intuition.
“Nice ride dude” I reply after a moment with a gleam in my eye. I allow him to continue
“Yea this will be my sixth trip to the mansion, so you know it’s no big deal. I pretty much run the show over there. I can go into the house…” he pauses for a moment then points at me “You can’t…but I can just walk in there whenever I want.”
“Cool man, you’re the boss-man over there huh?”
“Yes I am”
“Well then I appreciate your showing us around tonight, good to have a man of experience running the show.”
He is satisfied with my gratitude and returns to eating his fries.
Eventually the two guys leave. Andrew and I immediately go berserk over the biggest douchebag in the world interaction.
“I told you dude! He’s the worst ever” he says
“I mean Jesus, I thought you were serious but good fucking God that dude is unreal”
“And get this, his friend told me that the girl in the picture is in fact an escort and Playboy girl madam who found him so intolerable she left without fucking him on Thursday.”
“So epic. So predictable.”
After we finish our food we go into the front of the hotel and meet up with a number of other 2+2’ers including ‘Wandigo’ and ‘Bkice’. We wait around for quite a while as the Absolute Poker people wait for two people who are missing. They never show and we take the huge ass Hummer limo with a group of about eight:
(And one with just Andrew and I because he’s the shit)
We start slamming down the bottles of liquor and juice in the cooler. Some guy in the front asks anyone if they want some free weed “You sir are truly a king among men, to give away something as precious as weed” I tell him. We finish all the bottles. ‘Bkice’ suggest I bust out a “Gray Poupon” on someone and I immediately agree. I roll down the window and watch LA go by as I patiently await my opportunity. Finally we pull up to some 30ish looking dude in a sports car.
“EXCUSE ME SIR!” I yell in an absurd British accent, causing him to look up
“DO YOU HAVE ANY GRAY POUPON!?” then I start slowly sliding down and putting the window up laughing “HA HA HA HA HA!” loudly in the same slow absurd accent. The car bursts into enormous laughter and I am rolling on the ground.
“Jesus he’s so pissed! That guy is so angry!” they are all yelling.
“What the fuck for?” I ask “I’d be dying if someone did that to me. That shit doesn’t happen every day. I mean shit, when was the last time nailed you with a Gray Poupon?”
We continue on our long journey until we finally arrive at the gates of the mansion. They drive us to the front of the Mansion and allow us to bypass the line because apparently Absolute Poker has sprung for a cabana. The hostess lady escorts us over and I am immediately attempting to chat her up. In the cabana she explains that we’ll have two servers and bottle service all night. Both service girls are really hot. I immediately turn to Andrew
“We need to go get girls, right now!”
“Easy there man, let’s grab a drink first.”
“Alright but let’s make this very quick, as far as I’m concerned this is the Super Bowl of pick up and I’m not gonna waste a single second. I mean look at this fucking place.” We glance around the room; it is absolutely packed with hot girls dressed in either lingerie or nothing
And those hot girls, they’ve brought Oompa Loompa’s with them.
We quickly make our drinks and immediately after I walk onto the party floor and approach the first two hot girls I see
“Hi girls, how’s it going tonight?”
“Good! You?” they say enthusiastically
“Going quite well for me, where’s your girls boys tonight?”
“We haven’t met many yet”
“Well I’ve got a ton of awesome guys you should come meet in the cabana, I can promise you they’re considerably more outgoing and direct than I am too.”
I walk the two girls into the cabana and introduce them around. I start chatting up the tall brunette one. She says she’s from New York City and her name is Lisa (name changed.) I tell her I’m coming to New York in July. She suggests a helicopter ride. I tell her it’s a date and to put her number in my phone. She does so. Eventually the two girls excuse themselves to go wander around the party.
Andrew and I decide to wander around the party just taking in the sights. He also needs to use the bathroom. There is even a cute girl who has to man the port-o-poties and I start talking to her about how her night is going. It is immediately clear that she is used to being ignored at these parties and I guess considering she’s dressed plainly next to a bunch of naked women that’s not shocking. I ask her if any guys ever bring her drinks. She says very rarely. I tell her we got a bunch of bottles some quasi legitimate poker site bought us and I’ll bring her one. She asks for a screwdriver.
I walk back towards the cabana with Andrew. In the moving crowd I pass a girl in blue lingerie and say
“Blue is really your color, you look gorgeous tonight.”
“Thanks, I like your accent!” she says back
“Then we’ll have to talk later.”
The crowd keeps moving and we’re separated. Andrew and I reenter the cabana and find out the bottles of Cristal are about to be opened. I decide to take a brief break from hitting on women to drink some of the pretentious alcohol. “I don’t know, it tastes pretty good to me Miles” I loudly state to see if anyone can catch a Sideways reference.
As I’m drinking a glass the girl in the blue lingerie walks past our cabana. I quickly walk over to her and say “Hey I’m supposed to talk to you.” We hit it off immediately and I invite her and her friend in pink lingerie into our cabana. I introduce them around and Andrew starts wingmaning with the girl in pink.
Turns out the girl in blue and I have a considerable amount in common and she has a really easy going sense of humor. We take the two of them out onto the dance floor and we start grinding. After a while we see actor Crispin Glover hanging at a table and we go over to ask for a picture. He briefly poses for us then immediately goes back to chatting up his blonde.
We look over at a cabana that is packed with people behind a rope and many camera men. Peering inside we catch a brief glimpse of Hugh Hefner, though gaining access to him so I could say something totally absurd (I’d hoped to tell him I think he’s a homosexual looking for the best possible cover up to stay in the closet) is unfortunately impossible
While looking in the cabana she remarks “Don’t you think it’s gross how much older he is than his girlfriends?” She had told me she’s 23 earlier. “Well you wouldn’t like me then, at 24 I’m a lecherous old man next to you. Stay away from me.” I playfully push her away from me.
We return to the cabana and the lingerie clad girls we are hanging with tell us they’re going to go off and look around the party and be back later. I made sure to get the girl in blue’s number. I tell Andrew it’s time to go looking for more girls. I pour a drink for the girl working the port-o-poties and we walk to the bathrooms. I give her the drink and tell her it’ll cost a kiss on the cheek. She’s completely shocked I remembered and quickly kisses me then tells me I’ll be getting a ton of them tonight because I’m so sweet. “We’re certainly gonna try” I tell her.
Andrew and I wander back through the party. We hit on some girls; not very much happens. I walk past a woman holding a pink umbrella sitting down
“Nice parasol” I say to her
“Thanks but it’s actually an umbrella”
“Yes I noticed, and quite pink”
I start chatting up Brandi “like the alcohol”, who tells me she is a stripper in Las Vegas. I tell her that’s something we have in common and we get into the business of my work. I keep teasing her.
“Do you know why men wear ties to parties Brandi like the alcohol?” I ask
“No why’s that?”
I hold up my tie to her and say “Hold this”. She does. “Now pull in” I say. She does, and as she inevitably drags me close I lean in and start making out with her. It’s the called “The tie trick” and I developed it while out half drunk one night in Madison. It’s why I wear ties on the weekend now.
Brandi and I make out for quite a while, with her jamming her tongue down my throat. I tell her to put her number in my phone. I tell her I’m entering her name “Brandi like the alcohol. Okay, now for more” then lean in and start making out with her again. “See ya around, call ya soon!”
I go back towards the cabana and pour myself another drink. I walk back onto the floor and start chatting to two girls near the dance floor. They engage me, but also tell me they are lesbians.
“I call bullshit! Make out right now!” I half yell at them. They immediately start hardcore making out and groping each other. “Boo yah!” I exclaim while watching. I start dancing with both of them and they grind me for a while until some random Euro trash guy shows up and pulls one of them off. Fucking Euro trash ruining my fun. At some point the song ends and I tell my girl I’ll take her and her girlfriend to the cabana, and they ditch the Euro.
In the cabana I start asking a shit ton of questions about their relationship. Eventually we get on the subject of sex. I ask if they ever get a guy involved. They say sometimes they do, but they’re almost always unsatisfactory and too brief
“Oh that shit wouldn’t happen with me, I can handle all that shit. I go forever!”
“That’s what all the guys say!”
“Fuck that shit! I am the fucking man for that job!” The alcohol is starting to take hold.
Eventually I lose track of the lesbians in the sea of nudity and booze that is the party. I go walk around the outside area and chat up random women. I wind up making out with two of them (I can’t remember how that shit happened, probably the tie trick) and collect three numbers, including a girl I chatted up for 30 seconds. The truth is; random numbers you collect during drunken moments at parties are pretty much pointless. No way that girl ever remembers you, and certainly not after a 30 second interaction. I walk over to the dance floor and pass Tom Green on my way. On the dance floor I start grinding with some random girl and then suddenly Snoop Dogg jumps on stage and starts rapping his ass off.
I try to get girls to dance with me during the performance but they are all so totally zoned in on Snoop that I get shot down almost every time. That’s what I get for trying to compete with a pimp like that.
At some point I wind up back in the cabana. The girls in lingerie come by and say they were looking for us. We start rebuilding the attraction with them and I quickly remember how easy it was to get along with her. I am flirting heavily. I ask her if she knows why guys wear ties at parties. We are lightly kissing seconds later. Someone suggests we all go to the grotto. I don’t have any swim suit but the girl in blue lingerie wants to go so I’m fucking going. Besides, this could be my only chance to swim in the Playboy mansion grotto, so passing it up seems like a terrible idea. As we’re walking towards it Snoop Dogg is walking through the crowd and the girl in blue says she really wants a picture with him. I immediately step right in front of his entourage and loudly say
“HEY SNOOP! My girl is a huge fan dude, can you take a picture with her?”
“Yea sure man” he replies.
I try to put my arm around him in the picture, and his enormous bodyguard behind me immediately pushes my arm off.
The group walks into the cave like area that is the grotto and many of us strip down to our underwear and jump in. The grotto is filled with men in underwear, girls in underwear, and just flat out naked girls. Someone says a couple is having sex in the corner. I don’t bother checking because I’m too busy hitting it off with the girl in blue.
Meanwhile, somewhere else in the party, 2+2’er Wandigo was busy being the fucking man:
After hanging out in the grotto for a long time security comes and tells us we all have to leave as the party is over. I have trouble finding all the pieces of my clothing on the mats, and it takes a while to get fully dressed. Outside the cave the four of us have to line up to wait for a ride in the shuttle. I’m talking to the girl in blue the entire time and we’re finding out that we have a ton in common. She is shivering. I give her my jacket and tell her to not even try to refuse it. We’re both fitness nuts and discuss how we’d love to have a first date where we went for a run instead of the normal cliché things. I tell her if she makes her way to Vegas we’ll have that run and I’ll cook dinner afterward. She tells me she’ll seriously consider coming. Boo yah.
It takes half an hour to get to the shuttles. When we board I sit down next to the girl in blue and we spend the whole ride home talking. I feel pretty sober. We are getting on very well. Behind me Andrew has really hit it off with her friend in pink, and she seems really into him. The girl in blue tells me she is absolutely shocked that she kissed me at the party, that she never does things like that.
When we get off the shuttle at the parking lot the two of us couples stand around talking. They say they need to be getting home, that it’s an hour drive. We invite them to the hotel. They decline because of the long drive. I can tell that the girl in blue is pretty conservative but it really seems like the one in pink wants to jump Andrew. Each couple kisses a few more times and then they leave.
On the corner we run into another guy from the party. We discuss how we’re going to get home. Andrew is texting with the girl in pink. He says they’re willing to give us a ride to the hotel. Sweet.
They pick us up in their SUV and drive us half an hour over to the hotel, in what I think was in the opposite direction of what they were going, which is very nice of them. At the hotel they again decline Andrew’s invitation to hang out for a while. We say our goodbyes and the three of us get out of the car.
In the lobby we hear about the after party going on up in a suite, but apparently nobody else is being allowed in. Andrew and I decide to go get a hamburger at the café next door instead (end result of that after party was numerous guys getting action and Wandigo winding up with Ron Jeremy in his hotel room.)
After we finish our food we go back to Andrew’s room. It’s past 4am and we’re both exhausted. There’s no rooms left downstairs and I ask if he cares if I crash on the other side of the huge bed. He does not. We strip down and get into bed, lying back to back. I went to the Playboy mansion and wind up sleeping next to a man; I think the gay guy from Friday was right about me.