The Most Disturbing Conversation Ever

August 28, 2019

This is from my first book, I Hope They Serve Beer In Hell (book here) (audiobook here)

This story catalogs a Friday night that completely changed my life. It is divided into two parts for easier comprehension. The first part is a little slow, but be patient, the payoff at the end is WELL worth it:

Part 1: Tucker meets adoring fans, gets cock-blocked

Last Friday began rather innocuously enough at The Union, where we drank as much beer as we could pour into our faces, as it was $5 all-you-can-drink from 5-8. The highlight of the early part of the night was when I drunk-dialed one of the MTV producers, Serena [this was about a week before MTV was set to do a documentary about me]. She had made the mistake of giving me her personal cell phone number and telling me to call her "anytime you have any questions or anything." That's like Chamberlain telling Hitler he can have the Sudetenland. You give me an inch, I'm going to take the whole yard stick.

Tucker "So when you film me, are you going to follow me everywhere?"
Serena "Yeah, that's the plan."
Tucker "Well, what if I hook up and the condom breaks. Are you going to follow me to Walgreen's to get some Ru-486?"
Serena "We'll have to see about that."
Tucker "You have a sexy voice. What are you wearing?"
Serena "A moo-moo."
Tucker "What?"
Serena "Tucker, I'm like 250 pounds."
Tucker [Long, drunken pause] "MTV better send a different producer."

Thankfully, she is smart and has read enough of my site so she picked up on my drunk sarcasm. And more importantly, she is not even close to 250.

I was drinking at an alarming rate and was well on my way to breaking things and fornicating with hot girls, when some guy came up to me and said, "Aren't you Tucker Max?"

He was a huge fan, and was all excited about meeting the actual Tucker Max in person. I am not a big enough celebrity yet to be used to this, so of course I ignored everything else and basked in the glow of adulation as he introduced me to all his friends. Of course, that glow of adulation might have been the five tequila shots I had done in the past hour.

I can't remember what he and I talked about, but I'm sure it was exclusively about me and how awesome I am. The funniest part was when he was ready for the next round, asked if I wanted another one, then looked at my unfinished beer, and said, rather condescendingly "Oh. You're not finished." You gotta love it when your own fans are calling you out. I deserved it, and I would expect nothing less. Hey, if I can't take a joke, then fuck me.

Anyway, we were talking, about me of course, when this girl came up and basically wrapped herself around me and started almost making out with me. I chatted with her for about 20 minutes, when she said, "Let's go back to your place." A nod of ascent later and she took my hand and we headed to the door. I like my fans, but I am not passing up pussy for them, even though I am pretty sure that guy said to me as I was leaving, "Tucker, what are you doing? She's a high 2-star at best." I legitimately thought, at the time, that she was a 4-star, and we all know that in these matters, perception truly is reality.

Then came perhaps the greatest cock block I have ever seen. As we were leaving, her friends, seemingly on cue, descended on her from all different directions of the bar. I never even saw them coming. They herded her away from me and into a cab, then piled in after her. The last one turned to me and said, "Sorry, no more room in the cab." The last thing I heard from inside the cab was the girl saying, "But I want to have sex with him..."

The bait and no-switch was such a shocking and unexpected turn of events. I stood out there in the cold for awhile, staring at the taxi as it drove off down the street, before I eventually just went back inside and wandered around the bar like a lost vagrant. My mind was having trouble shifting back into "Pursue" mode after being in "Gonna get laid" mode. It was then that my cell phone rang, and part two of the story began...

Part 2: Tucker has the most disturbing conversation ever

I answered my phone, still in a daze from having eager vagina snatched away from me, and it was none other than Jez, the girl that used to have two vaginas.

"Hey what are you doing? Come up and meet us, we're at Felt. It's on Halsted, right north of Belmont." Everyone who lives in Chicago knows what's coming next.

I take a taxi and arrive to find a bar completely packed with dozens of the best-dressed, hottest guys I have ever seen, and hardly any girls. Oh, that's fucking great Jez, thanks for bringing me up here, how am I supposed to pick up a girl at this fucking sausage-fest...TWO GUYS ARE KISSING IN THE CORNER!!

Oh no...

Jez comes running over and gives me a big hug and a kiss. She is wasted. "Come meet my gay friends. One of them looks just like Christian Slater!"

I am dragged over to the faux Christian Slater and the rest of the gay friends, and introduced as such, "This is my straight friend Tucker. Isn't he so cute!!" They all readily agree, and I desperately feel the need for an alcoholic drink. I tell the bartender to just bring me anything strong. That short-sighted comment is immediately rewarded with a raspberry long island iced tea. I suppress the urge to throw the drink in his face, and then pay him $10 for it. I guess I'm gonna get fucked one way or another.

Having cut my clubbing teeth in South Beach at clubs like Twist and Swirl, I am used to hanging out around gay guys, and thus am completely comfortable around them, but this was a totally different experience. In South Beach, the coolest clubs are the "gay clubs," but it's usually pretty obvious who is gay and who is not. The gay guys are flamboyant and entertaining, real thin, drink bright colored drinks, and wear dazzling, shiny clothes. The straight guys wear tight shirts and hang out in packs, waiting for opportunities to hit on the numerous hot girls that go to those clubs "just to dance."

Not in Chicago. In Chicago, the gay guys look and act just like straight guys, except they accessorize and dress better. And suck dick.

I was at the table with a girl and three guys, each of which on first or even second glance looked and acted just like any of my other friends, except my friends don't want to push in my stool. But after I got used to it, I was actually thankful to be hanging out with these great looking guys, all of which are gay, because it just means less competition for me. Ask any of the 40 or so straight guys who have attended Vassar over the past decade; having lots of gay guys around means the girls will be desperate. Unfortunately, there were no girls around except for the obligatory fag hags, which did not tickle my loins.

So being bored, I couldn't resist the temptation to start quizzing these guys. There are just so many questions. I started off by throwing one out to the table:

"Alright guys, seriously, what is it about sucking dick that you like so much?"

They went on to explain that sucking dick is all about imagining it to be your own dick, "You just treat it like a little version of you." They also told me that getting your dick sucked by a guy is much better than by a woman, because, "We know what we want. Women don't have dicks, they don't really know how to deal with them like we do."

It turned out that two of the three guys had been with multiple girls; Christian Slater had been with like 10 or so, and Adam had been with about 8, so they had a reasonable basis for comparison. I guess. I'm just going to have to take their word for it.

We leave Felt and decide to go to Manhole. Just by the name, you should be able to discern some things about Manhole. But let me be clear for the stupid readers, like my cousin: Manhole is a famous gay club, and it is famous for a reason, namely, lots of gay "things" go on there.

On the way there, Adam expresses concern for me, "Tucker are sure you want to go here? This place is"

Bitch please. I'm not about to avoid such great story potential just because of some swinging dicks, "Dude, I grew up in South Beach. There is nothing in there that could shock or disturb me."

He was right. I wasn't prepared. Let me attempt to describe this place: The club opened into a huge room, and ended in a tunnel that led to another huge back room. The front room had a large, star-shaped bar in the center of it. The ceiling was ringed with dozens of TV's, much like your average sports bar. Unlike your average sports bar however, the TV's were not featuring athletic competition. That is unless you consider vigorous and explicit gay sex between men hung like Tijuana mules to be a sport. The walls were a dark, dingy brown. I stayed at least two feet from them at all times. And my favorite part: Every guy had his shirt off. Except me. And it was going to stay that way.

Jez and I get in line for the bathroom, and every guy in line immediately pushes her to the front. She asks why, and they say, "Because you actually have to go." The door opens and three guys come out of the one-room bathroom together. The last one stops, says, "Oh wait, I have to pee," and heads back into the bathroom.

Jez and I decide to go in the bathroom together. We walk in, and I make her close the door handle, because I don't want to touch it. I have never been more disgusted in my life. The walls, which were originally some shade of orange, were now an oily brown, having been re-painted with splooge stains. Some of the stains were like 10 feet high on the wall. Who was fucking in here, Peter North? I pee in the sink and quickly exit, refusing to touch any surface.

We meet up with three other gay guys who are friends with Adam. One of them, Lloyd, takes Jez and I on a tour of the rest of the club. The back room was the dance area, and it was packed with hundreds of shirtless guys. The room smelled like some horrible combination of Isaac Mizrahi, sweat and gay sex. As Lloyd took us through the throngs of dancing Sodomites, he got into a sort of scuffle with one of them, an obvious flamer (instead of the more masculine ones we had been hanging out with). The confrontation was quickly diffused, but I couldn't stop laughing at the flamer when, as we were walking away, he said in his best Nathan Lane voice from Birdcage, "OHHH, I JUST WANNA BEAT HIM UP!!"

Some random events over the next few minutes:

-One guy asked me if I liked football, and he said his favorite teams were the Packers and the Titans, though he liked them better as the Oilers. I'm just going to pause here and let you insert your own joke.

-I asked the only girl in the place other than Jez if I could feel her tits. She said sure, and I gave them a good slapping. It was awesome. She loved it because she thought I was gay and thus safe, and I loved it because I am straight and she had great tits. Everybody wins!

Jez and I took a spot next to the front bar, and her gay friends immediately surrounded us. Jez was mostly talking to Adam and Christian Slater, while the other guys, Lloyd, Dave and Mike talked to me.

The three of them were right up on me, each with their shirts off. They began asking me about the gay porn showing in the TV screens, and whether that offended me or made me uncomfortable.

"No, not really. Porn is porn; I've seen so much in my life I've become inured to it. Most of the shots are up close, too. You can't even tell if it's a male ass or a female ass getting fucked until they pan out."

After they realized I was not averse to discussing gay topics and was relatively comfortable in a gay environment, the fucking floodgates opened.

The first subject was something I knew nothing about, and was actually kind of interested in, in a sort of clinical, sociological kind of way: How do gay guys decide who fucks who? I mean, when two guys go home, do they flip a coin? Play rock, paper, scissors? How does that work?

They explained that there are two types of gay guys: Tops and Bottoms. Tops are the ones that like to do the fucking, the pitchers, if you will, and the bottoms are the ones that like to get fucked, the catchers. Most gay guys have a preference, but can go either way, though there are a certain percentage that are only one way or the other. So if two Strict Bottoms go home together, then no one gets fucked, though there is still the oral sex option.

This really was remarkable info to me. I just assumed that when you went home with a guy, you fucked him and then he fucked you, but apparently that is rarely if ever the case.

One of the TV screens was showcasing a gay guy tossing another guy's salad, and we began discussing the finer aspects of such activity [ed note: tossing salad means to eat out someone's asshole].

I admitted that I had never eaten out a girl's ass, but that I had had girls do it to me, and that yes, I liked it, especially when the girl jacked me off as she was doing it. They started telling me all these trade secrets about tossing salad and the various ways that one could improve it. They even asked me whether I washed my ass before I had my girlfriend go down there. I told them that I was courteous and did indeed clean myself beforehand. Dave told me I was "well trained," because "there is nothing worse than going down there and finding it all grainy."

Then it got a little weird.

Dave started testing my limits. It is apparently a big thing for a gay guy to fuck a straight guy, and he really wanted to break me in:

Dave "So, would you ever let a guy eat out your ass."
Tucker "No, I'm not gay. And that would be weird."
Dave "Right, but if you aren't looking you'd never know if it's a girl or guy."
Tucker "I don't know about you, but I usually look at the people who put their tongue in my ass."
Dave "What if your girlfriend started it out, but then a guy moved in and finished. You would never know."
Tucker "I mean, I don't know, I guess...but...what kind of girl would...look, I'm not gay."
Dave "You know, gay guys give the best head. We teach female porn stars how to do it."
Tucker "I don't doubt that, but it doesn't change the fact that I'm not gay. I don't like dick. Except for mine, of course."
Dave "I like yours too."
Tucker "That's pleasant."

From that point on, it became a game of advance and retreat with these guys. They would test my sexuality with questions like that, and I would have fun talking to them about it, but would always draw the line before they suggested we head into the bathroom. The funny thing was, I had probably three of the hottest guys in there hitting on me, especially Dave. That guy could get so much pussy if he was straight [Duke Law inside joke: he was hotter than Malkin].

It was a very unique feeling, to be so actively and aggressively pursued by guys. Now I know what hot girls feel like, being hounded by multiple guys at once. On one hand it is a flattering feeling because of the attention and the obvious desire for you, but it kind of leaves a mildly annoying and hollow tang, because you know that all the guys really want to do is fuck, and they only care about you because of what you represent to them, not who you are as a person.


[WARNING TO ALL GUYS: You might want to stop reading here. The ensuing conversation I am about to recount prevented me from sleeping for a full two days, and has permanently and irreversibly scarred me. Save your psyche while you still can. Females have nothing to fear.]

At one point during a lull in the conversation, a random gay guy got involved in our conversation, and figured out that I was straight and they were trying to get me to have a homosexual experience. He dropped possibly the biggest, most disturbing conversation bomb EVER DROPPED ON ANYONE EVER:

Him "I bet you've already slept with a man."
Tucker "Alright, come on man--I invented Tucker Max Drunk, but not even Tucker Max Drunk makes you switch teams."
Him "How many women have you been with?"
Tucker "I don't know, about [number]."
Him "Oh yeah, I bet you've fucked a man."
Tucker [Getting obviously frustrated] "How??"
Him "I have three words for you: Post Op Transsexual."

It took three seconds for the full meaning and significance of that statement to filter through my drunken brain. Then came the first stage of loss: Denial.

Tucker "What? Get the fuck out of here. I've never fucked one of those."
Him "You wouldn't know."
Tucker "Man, give me some credit."
Him "Have you ever slept with a woman who told you she couldn't naturally lubricate, that she had to use KY?"

Oh no.

Tucker "Well...yeah...two, actually."
Him "Uh-huh."
Tucker "No. No way. Stacey was one, I went to college with her, she was definitely a woman. Everything about her was woman. And she was like 17 when we fucked. You can't be post-op that young."
Him "Probably not. What about the other one?"

Please no...

Tucker "Uhhh, I met her in Miami..."
Him "What did she do?"
Tucker "She was a stripper."
Him "Did she have fake tits?"
Tucker "Yes."

This isn't happening. He is fucking with me.

Tucker "No, man, she was not a fucking man. She didn't have an Adams apple."
Him "That is a two hour outpatient surgery. Easily done. Cheap too."
Tucker "But it was...she had a pussy. IT FELT LIKE A PUSSY."
Him "Surgery is amazing these days. She probably even had a clit."


Tucker "But she was soft. Her skin I mean. She felt like a girl."
Him "You're smart. You know what large amounts of estrogen do to the male body, don't you?"
Tucker "But what about her voice? She didn't sound like those absurd trannies on Springer."
Him "Estrogen. And maybe even vocal chord surgery. It would make sense if she has a lucrative stripping or escorting gig to protect."

I just stood there, too shocked to move, trying to recall every detail about her to refute his argument.

Tucker "Wait, wait, wait..."
Him "She gave great head, didn't she?"
Tucker "She was a stripper! They give head for a living!"


Him "Was she tall? Taller than you?"
Tucker "Yeah, but I've dated lots of girls who were taller than me."
Him "But I bet none of them had hands as big as hers."


Him "Did you have anal sex with her?"
Tucker "Yeah."
Him "You ever had anal sex with other girls?"
Tucker "Yeah."
Him "Felt a little different with her, didn't it?"

Oh dear merciful Jesus.

He was right. I distinctly remember that.

Him "I think you did."
Him "Don't feel bad, this happens to lots of guys. You'd be shocked."

I was in SHOCK. I could not sleep or function for the next two days, as I went over every detail I could remember about this "girl." I am still undecided about her. Yes, he made good points, but everything about her I recall as being feminine. The way she smelled, her touch, her appearance, everything. And it was a nice strip club where I met her, Rachel's in West Palm Beach. Don't they check for these things?

He went on to explain that some post-op transsexuals will go to the bathroom before sex, and put the KY in without even telling the guy. Others don't even have fake breasts, because the elevated estrogen levels can give them B cups. He said she might not have been the only one. My brain was completely fried after that conversation. I still don't know what to think.

Gentlemen, all I can say is don't spend too much time cataloging your ex-hook-ups because it will drive you nuts. Just pretend you never read this and move on. You wish you had heeded that warning now, don't you?

Tucker Max

Tucker Max is the co-founder of Scribe Media, a company that helps you write, publish, and market your book.  

He's written four New York Times Best Sellers (three hit #1), which have sold over 4.5 million copies worldwide. He's credited with being the originator of the literary genre, “fratire,” and is only the fourth writer (including Malcolm Gladwell, Michael Lewis and Brene Brown) to ever have three books on the New York Times Nonfiction Best Seller List at one time. He was nominated to the Time Magazine 100 Most Influential List in 2009.

He received his BA from the University of Chicago in 1998, and his JD from Duke Law School in 2001. He currently lives in Austin, Texas, with his wife Veronica and three children.

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