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

Blackjack Cougar


There are nights when I expect to get laid. There are nights when I hope to get laid. And there are nights when I’d rather lose all my money to a gaudy casino than think about women. On this night, boners were for jackpots and free Coronas.

I drove to Vegas for the weekend to attend a Saturday morning writer’s workshop and hang out with Baba and McBride. McBride already had plans for Friday night, so Baba and I hit the strip alone. Since Baba had two cousins staying at the Bellagio for the night, we met them there around midnight. Having grown up in Jordan, their FOB factor was blatant. One of the cousins wore extra short orange Euro shorts, a small, tight shirt, and had a giant black camera dangling around his neck, yet he still did not think it odd or wrong to approach women in his get-up. Despite having John Stockton-like leg hair as well as poofy, uncombed hair that made it look like he’d just gotten out of a pool—which may have been true—he was all smiles, so we let him be. Since it was Baba’s cousins’ first time in Vegas (obviously), they decided on the agenda. Gambling was the choice. First it was craps, then roulette, and blackjack. Before long, we’d been at the tables for over three hours. Gambling has a funny way of eliminating the concept of time.

A little after two, the blackjack table was becoming stagnant. The dealer was depressed; the bozo next to me hit on a 15 when the dealer was showing 16; and there was a grumpy fellow three seats down who looked like Newman from Seinfeld.  I needed a change.

A couple tables down, I heard a group of women making up words and cheering uproariously. Curious, I examined the commotion. Jackpot. Four milfs had an entire table to themselves, and, as if destiny was calling, there was one open seat. I grabbed my chips and quickly walked over to their table, smiling mischievously at them as I sat down in first position.

The table:

Dealer: A smiley, quiet Asian guy.

First seat: Me, Captain Rimjob.

Second seat: A freckly forty-something blonde wearing a sky blue sundress that seemed two sizes too big. At least four more beers until she was up for consideration.

Third seat: A hot, busty, blonde forty-year-old birthday girl with a white top, nipples protruding through the material. Primary target.

Fourth seat: A cute brunette with ugly, short acrylic nails and facial features that disclosed that she hadn’t done much smiling in her lifetime. One more beer until consideration.

Fifth seat: A mediocre brunette with plain features, a flat, pancakey chest, and untoned arms that led to my immediate assumption that she had dumpy written all over her. She was the only one focused on her chip count. Sex appeal: N/A.

I was bombarded with questions immediately. I found out they were all in the medical field. Two were gynecologists; one was a nurse; and the hot one was a surgeon. When they discovered I was a teacher, they all complained to the dealer, “Teachers don’t make enough money; give this guy a blackjack.” It helped, and I began winning.

The busty one in Seat Three was stealing looks at me. I could sense it. When we made eye contact, I smiled. When we’d win, we’d all high five each other. Beneath the high ceilings of the Bellagio Casino, my expectations for the night took a sinister turn for the dark side. Sex was suddenly on the table.

The two gynecologists became concerned about me when I started getting up every twenty minutes to pee. “You may want to get your prostate checked out. Peeing that often could mean you have an enlarged prostate,” one said. They all watched me get up.

            “Don’t worry. I’m only twenty-eight. I pee because I never puke,” I said. Without another word, I walked to the bathroom, leaving them to wonder about the correlation between peeing and vomiting. I wish I were there to hear the probable discussion they had about my prostate/pee frequency/vomit factor/hotness/mysteriousness. If anyone is looking to become a millionaire, I recommend inventing a miniature-recording device that can be easily stuck underneath tables to record after-you-leave conversations. I would invent it myself, but I wouldn’t know where to find the Guy Who Approves of All New Inventions.
Update: I heard Skymall already invented my idea. Never mind.


Baba and his two cousins came over, but after two gross hookers snatched his cousins away, it was just Baba and me. The cousins would eventually wind up throwing the hookers out of their room for charging $1,000 for sex.

Good wingmen are plentiful, but great wingmen are rare. Two come to mind. The first is Pico. During spring break in Havasu, Pico walked around with me telling girls that I had a nine-inch cock (a lie), which resulted in me making out with over forty girls in a three-day period. The second is Baba. Girls see Baba’s soft features and sincere smile, and they are willing to tell him anything. So when Tera, the busty blonde in Seat Three, took a pee break, I sensed an opportunity.

            “Uh, dude, tell Tera that you’re going to take me away. See what she says,” I told Baba. It was a test to see how she’d react. Baba walked toward the bathroom to intercept Tera on the way out.

            A few minutes later, I saw the two of them walking together, smiling in the wake of their apparent conversation. Baba walked up to me. “‘You are not taking Dave away from me.’ That’s what she said.” Perfect. Now all I had to do was wait this out.

Half an hour later, Tera’s friends abruptly got up and retreated to their room. I looked at Tera. “You’re staying, right?” I asked. Seized by my conviction, she sat down next to me.

            “Yeah, I’ll play a little more,” she said.

The following fifteen minutes was filled with mindless chatter and a shitty string of 20s for the dealer. I watched my winnings hopelessly dwindle away. I got up, stuffed my remaining chips in my pocket, and waited to observe Tera’s post-blackjack body language. The signs were good—all smiles, and she stayed at my side, keeping the slightest bodily contact. When our faces were close we briefly kissed, but no tongue. “Not in public. I’m kind of old-fashioned,” she said.

            I smiled. “That’s cool. Let’s walk.”

We walked toward the lobby. I felt bad for Baba, who had been ready to go and had stayed up an extra hour just to see if things would play out for me. It was now 5:30 a.m. I had to act.

            Baba lingered around the fringe waiting for us to figure things out. So I acted. “We need to party. Can we party in your room?” I asked Tera.

            She smiled. “No. My roommates are there.” 

            “Hmm. Well, we need to get a room then.”

            “We do?”

            “Yes. We need to get some beer, too.”

            “Okay.” Still smiling.

I motioned to Baba. “Alright dude, we’re going to party h—“

            “–Alright, cool…have a fun night. I’ll see you tomorrow, dude,” Baba interrupted, not wanting to spoil my chances with any unnecessary awkwardness. Baba gave me quick directions to the morning workshop, and he left. I was in Tera’s hands now, and she knew this. 

For whatever reason, there was an inexplicable fifteen-person line at the check-in. Sensing it as a threat to her patience, I slyly led her to the front, cutting in the process. Champions find a way to win. Two guys, who I had already judged as the non-confrontational type, noticed but didn’t say anything. Tera and I walked up to the desk.

“We only have smoking available,” said the desk lady.

Tera frowned. “How much is that?”


Tera hesitated. I took out my wallet, prepared to split the cost. Tera had other ideas. “Is there anything else available just for tonight?” Tera asked.

“That’s it, unless you want to get a suite. That would be $450.”

Whoa,” I said. There was no way I was splitting that. 
            Tera ignored me. “That’s fine.” She handed the lady her credit card.

“Four hundred and fifty dollars? Are you sure? Let’s just get the smoking room,” I said, feeling a pang of guilt.

“No. I hate smoke. And besides, it’s my birthday. This is my gift to myself.” 

The lady handed her back her card. “Check out is at noon.” The room was booked for a whopping six hours. Tera had just paid $450 to fuck me in a room that had a rate of $1.25 per minute. If I couldn’t deliver, I’d go down as the biggest rip-off of her life. The fourteen Coronas I’d had maybe weren’t such a good idea.

The “suite” was a major disappointment. The room was maybe twenty more square feet than a standard room. There was a half living room and a large bathroom. Other than that, I didn’t see how this room cost $300 more than a regular room. Nevertheless, we got down to business immediately.

Mid-make-out she stopped me and said, “Okay, you have no idea. I’ve never done this before.”

            “You’ve never been with a guy?”

            She laughed. “No, I’ve never had a one-night stand.” She brought her hand up to her forehead, smiling.

            “Well that’s hard to believe, but okay,” I said, kissing her neck, not believing her. “So why am I so special?”

            “I don’t know. I feel comfortable around you. Well, that and you’re fucking hot.”

We laughed. Then we got naked. Her blowjob skills were well-refined, not a single tooth. And after another twenty minutes of foreplay, we fucked. Unfortunately, the mandatory $450-suite foreplay action, combined with my fourteen Coronas, had withered my hard-on down to seventy-five percent. To top things off, she was abominable at sex. She lay there like a starfish, eliminating any opportunity at developing a rhythm. After five minutes of starfish sex, she said, “I don’t know. This feels so impersonal.”

            “Okay.” Sick of trying so hard for so little, I got off her and lay down.

            “Whoa. I didn’t expect you to give up so easy.”

            I forced a smile. I was drunk and tired. But I was still horny. “Let’s take a shower,” I said, insistent on milking whatever we could out of this ritzy occasion.

She blew me in the shower. After the shower, she blew me on the bed, finishing things in her mouth. I could sense her disappointment. After lying down for a few minutes, she whined about how she regretted taking a shower because her hair was “all curly” now. I said, “Oh,” and then I rolled over and passed out.

My alarm went off three hours later. I awoke to find her wide-awake, naked, lying next to me. She was still hot. Upon seeing me rustle awake, she said, “I didn’t sleep at all last night.”

            “Really? That sucks.” I got up to go pee. “How come?”

            She waited until I got back. “I don’t know. I just…never do this.”

            “Well it was fun, right?”

            “Yeah.” She brought her hand up to her forehead again. She wasn’t smiling this time. 

I took a $12 cab to the workshop, just making it in time. I was, by far, the biggest dirtbag in the building. I was unshaven; my hair was unkempt; and my shirt was all wrinkly from accidentally sleeping on top of it. I found the hottest girl in the workshop and sat one seat over from her, but after a five-minute break, she was mysteriously sitting on the other side of the room.

I dozed off frequently, my mind often drifting back to poor Tera. After our pathetic attempt at $450 fortieth-birthday sex, I highly doubt she’d be having any more one-night stands for a while. I felt like the #1 draft pick who got paid millions of dollars, only to be a catastrophic bust, disappointing an entire city of hopeful fans. But that’s the good thing about one-night stands; they’re only for one night. I don’t have to hear her whine the next day for making the experience “impersonal.” I don’t have to hear her gripe about not going down on her enough. I don’t have to absorb glares from her judgmental friends. And most of all, no one ever finds out if I disappoint in bed. Well, except all of you.  





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