Making sense of my adventures with women, one disaster at a time.

Birthday Buttfuck



I had one thing on my mind: Vegas. Every year my entourage, ranging from three to ten guys, will make a trip to what has become our playground, our backyard. There is no other place on Earth that satisfies every desire and fantasy life has to offer. From the ritzy hotels to the pools, bars, clubs, women, table games, shows, and even sidewalks, life becomes a nonstop roller coaster ride. Nothing compares.   

Kaygee, Ron, Punchline, Tiger, Axe, Baba, Corky, and I headed out to a new club called The Bank at the Bellagio, our hotel. I’ve never been a fan of paying an extra $300 to stay at the big hotels because it has the same size rooms as every other hotel. But Ron had never stayed at the Bellagio and was adamant about it. And we did get into the club for free, so we couldn’t complain.

McBride, a Vegas native, flaked and tended to his girlfriend. We openly discussed his lameness, directly texted him our disappointment, but secretly understood his situation.

Our texts:


“Weak sauce”

“Get your ass out here! Everyone’s waiting on you”


I’d think much more highly of “girlfriends” if they’d let their men have a couple nights out when their friends are in town. Unfortunately, that’s not the case in most relationships. Sadly, guys with girlfriends are taking over the solar system.

Our first impression of the club was a bad one. Fatty after fatty waded her way through our eight-man entourage. Within the first five minutes, a pale four-girl crew began talking to us. Only one was halfway cute. The rest were in ruins. One had frazzled hair and a tattered shirt, which made her look like an unwanted leftover from a Jimmy Buffet concert; one looked like a Keebler elf; and the last one had a mouth on the side of her face, making her look like the ghost from the movie “The Ring” had just killed her, leaving her mouth agape in ghastly dimensions. We moved on.

Twenty rejections later I ran into a cute thirty-seven-year-old with brownish-red hair. I was rather lazy all night with my creativity. Instead of mentioning something mysterious about each girl’s outfit or headband, my line for the night was, “Who are you?” Some of the answers I got:

“What do you mean?”

“Who am I? Who are you?”

Girls who looked at me and walked away.

            “I’m Brandi.”

“What kind of question is that?”

“Oh, so is that your line?”

It failed several times, but it worked with Brandi, a sporty woman in her late thirties with auburn hair and high cheekbones. She wore a black top, tight jeans, and within minutes made it known she was wearing a sports bra and proud of it. The sports bra thing had me hooked, with visions of screwing her on a tennis court venturing into my mind. Moments later we were making out. Then we began “make-out talk,” an art I have come to master. With every potential one-night stand, I will take breaks mid-make-out to build my attraction and sexiness. It’s a cheap way of developing “chemistry” and a sleazy way of earning a girl’s trust. Some of my scintillating questions:

            “How long are you in Vegas for?”
            “You’re staying at the Bellagio, right?”
            “Do you have beer in your room?”
            “Your hair smells good.”
            “We need to get out of here.”
            “OK, you know what? I’m going to fuck your brains out tonight.”

             She responded positively to it all. The exit sign to our left glowed red, goading us on.

Brandi had come with her friend, a hot blonde, who was making out with a 6’8” black guy. Maybe it’s just me, but every time a tall black guy walks into a club, I instinctively check to see if he’s famous. This guy wasn’t famous, I checked. The blonde, who I later found out was married, ditched the guy and we made our way up to their room.

When we got to their room, a miserable fat chick was sitting in a chair alone drinking whiskey. The girls laughed at her. I steered clear, never making eye contact. She had cockblock written all over her. The blonde inquired where we were going, to which my future fuck pal responded, “This guy’s going to fuck my brains out. I’ll be back.” No one reacted. Then she got her things, and we left.

On the way to the elevator, I realized she had brought a giant backpack. “What’s in the backpack?” I asked, confused.

            “Things,” she said, suddenly self-conscious.

            “What kind of things?”

             “Girl things.”

             I let it go. We got in the elevator and went down to my room, making out the whole way. Then I received a text.


“Oooooh, booty call!” Brandi exclaimed.
             “Nah, it’s probably my friends.”
            As we got off the elevator, we unlocked lips, and I checked the message once Brandi was far enough away from me. It wasn’t my friends. It was a hot gynecologist I had met earlier in the night and written off. But now she wanted to fuck, and upon remembering a conversation we’d had in which she’d admitted she loved staring at penises for lengthy periods of time, I was suddenly feeling a pang of “what if.”

            Shit. Since I was about to fuck a girl less hot, I would have preferred not receiving texts from the gynecologist. That way, the next day I’d assume she would have been a dead end, subsequently making me feel like I’d maximized my fucking for the night. When Brandi got naked, I forgot all about it. 

             We hopped on the bed where a blowjob ensued. After only five minutes, she lifted her head and said, “What about me?”

            “What about you?”

            “Do you go down on girls?”

            “Nope, not my thing.” (A half lie. Unless I have a girlfriend, or an eight or above—this girl was a seven—I never go down on chicks. Although I have made exceptions.)

            “Oh, well that sucks.” Then she lay down and tried to spoon me, indirectly communicating her frustration and disappointment.

            Since she was good at blowjobs, I had an idea. “What about this?” I reasoned, “Let’s 69.”

            “Okay,” she whispered, smiling jubilantly.

             I got on top of her, on all fours, made my manhood perpendicular to her face, and started fucking her mouth. I chose the on-top-69 for two reasons: 1) I had control over the situation; and 2) It increased my chances of a rimjob. I wasn’t planning on 69ing her. Instead, I fingered her a little, sporadically licking her clit to make it seem like I was working.

My roommate, Kaygee, has an uncle who was once asked to help move boxes into Kaygee’s new house. The uncle reluctantly agreed, but when it came down to doing the actual work, the uncle moved very slowly, grabbing the lightest box he could find, grunting and panting the entire way as if he were in extreme pain. We later made fun of him. But when it comes to 69ing chicks like Brandi, I am Kaygee’s uncle.

Rimjobs were a no-go. She later said that rimjobs cause E coli poisoning. Right. Because I had no intention of ever seeing this girl again, I tested the waters. “Do you like looking at my ass?” I asked.

            “Not really,” she said, taking a split-second break from my penis.

I looked back at her. It was an odd sight. My penis was in her mouth, her eyes were closed, and her head was at an angle I didn’t know was feasible for vertebrates. She had put herself in the shape of a human S just to avoid the sight of my butthole. This was bad. My conscience took over. I got off her.

            “Well that was fun,” she lied. Inducing lies from people is never pleasant. But whatever, my fake 69ing had worked.

Sex followed. She was silent the whole time, barely going through the motions. After ten minutes of silent sex, I became bored. “Do you like anal?” I asked. First rule in negotiation: He who never asks, never gets. (I made that up.) It’s true; my students always ask for extra credit, and occasionally I’ll see their reasoning and cave.  

“Yeah. But we’ll need some lube,” she said, in doggie position, ass in the air.

            “OK, there’s some in the bathroom,” I said. I got up, penis flopping, and scurried to the bathroom completely unaware if we had any lube-like liquids. Shampoo…no. Bar of soap…no. Shave gel…no. Hand and body lotion…oh man! I grabbed it, giving it an unnecessary squeeze, and showed it to Brandi.

            “No, this won’t work. Check again,” she said, ass still in the air.




Probably the gynecologist. Pfff! I’m having butt sex.


There were no other lube possibilities, so I brought out the same hotel lotion bottle as before and said, “OK, got some,” squeezed it on my hands, wiped her ass, squished my wiener in, and began fucking.    

Silence. She didn’t even let out a pant, which caused me to become briefly insecure about my penis size. The insecurity faded once I realized how good the butt sex felt. After a few different positions, I finished on her chest and face.

We collapsed on the bed.



I suddenly saw the hot gynecologist as an option again. It was past 4:30, my privates were worn out, but I was up for anything. I tried to herd the girl out quickly, but she insisted on “talking.”  

I found out she was “happily married.”

            “What!” I exclaimed, “Does your husband know you’re going out having sex with guys like me?”


            “Well, does he have sex with other girls?” I almost said it condescendingly but adjusted my tone at the end.

            “No. At least I hope not.”

            “Oh my God.” No wonder the sex was silent; her hubby must have had a bigger dick than mine. Either that, or, she didn’t even like sex and was only having it just to be cool.

After ten more adulterous minutes of conversation, she grabbed her backpack—which went untouched until now—and returned to her room.

             I had work to do. Immediately after closing the door, I called the gynecologist—who had texted me three times, the last one reading “Very Disappointing.” She picked up on the third ring.

                Her: “Hello?”
Me: “Hey. I just got your texts.”
Her: “You are a disappointment.”
                Me: “You are. You left.”
                Her: “Well, we’re going to crash. We’re on our way to my friend’s house.”
                Me: “Lame. I just woke up. Let’s party.”
                Her: “No. We’re done for the night.”
                Me: “OK. We’ll talk tomorrow.”

                I hung up and went to bed. Twenty minutes later I was awakened by Ron, Kaygee, Tiger, and Punchline—the other guys were staying at Caesar’s. In a room with only two beds, one guy always gets assed out and has to sleep on the floor. The rule: the last person to get home has to sleep on the floor. Since I was first, no one was happy to see me. After hearing my butt sex story, the guys were even more furious. Not only did I fuck, but I also got a bed. And no one wanted to sleep with me. Tiger and Kaygee immediately hopped on the other bed. Punchline didn’t care, finding a spot on the floor. Ron was angry; he had booked the room, and was looking forward to staying at the Bellagio. Now he was going to have to spend his first night on a bed that likely had poop particles on it. He put on his hooded sweatshirt, thought about putting on a condom for extra safety, and then lay down next to me. When he found a mysterious brown smudge on his comforter, and he retreated to the floor. I was laughing the whole time. I had the bed to myself.     


   The next day began on the Strip and ended in the wee hours of the morning at the Casino Royale craps tables. The gynecologist and I were texting back and forth all day, but by the time I was finally able to see her that night, she had a dude draped over her, which sent me back to the craps tables.

   It would be nice to know what would have happened had I pursued the hot gynecologist the first night. But that’s the annoying thing about life; there are some backpacks I’ll never get to open.  




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