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

Penthouse Letters

 I possess a secret pheromone that attracts women between the ages of thirty to forty-five. It’s true. I can walk up to the hottest milf/cougar at the bar, and, more often than not, hook up with her. I tend to confuse or anger younger girls, who ultimately accuse me of “being creepy.” But when it comes to older women, I have a magic potion. 


            Woody’s Wharf had emerged as my favorite bar. It wasn’t a huge bar, but it had a certain dynamic that made it perfect for my style. I loathe bars that are simply one giant room. The animal in me thinks it essential to hit on girls without the whole damn bar as witnesses. Woody’s was different; there were four separate areas where I could work: the hallway, the bar and table area, the dance floor, and the smoking area. Girls in any one area couldn’t observe the other areas. Hopping from one space to the next gave me a fresh start no matter how many times I got rejected. I wasn’t concerned whether my new target had seen me hit on the tall cougar in the smoking area moments before. 

Barb, forty-two, was not the hottest milf/cougar at the bar, but she had a cute face and large breasts. I poked her arm and she stopped to look at me. “What is that thing?” I asked, pointing to her bustier. Before she could answer, Ron whispered, “Dude, she’s pretty thick.” He was right. But this wasn’t the best of nights at Woody’s. I disregarded Ron’s warning and continued.
            Me: “Who are you here with?”
            Her: “My friends.”
            Me: “Ah…your skirt matches your bustier. Was that planned?”
            Her: “Yeah. I just bought this. I like it because it hides my fat.”
            Me: “You’re not fat. Wait a minute. Are you married?”
            Her: “Yes.”
            Me: “Oh, well that sucks. I was hoping to make out with you later.”
            Her: [laughing] “Maybe you can. You never know.”
            Me: “Yeah right. Well maybe I’ll find you later.”
            I walked off. I wanted no part of a married woman. I’m no home wrecker. Well, maybe. I circulated through the bar, hitting on chicks. More girls rejected me. One girl stopped talking to me because someone around us laid a grisly fart, creating a ten-second stink. I suspected she was the culprit. I carried on, eventually stumbling upon Barb sitting at a table with her girlfriend. She smiled when she saw me. I was still doubtful about the “married” thing. I leaned in and spoke into her ear.

            Me: “Are you really married?”
            Her: “Yes I am. But it’s an open marriage.”
            Me: “Are you serious? You both agreed on this?”
            Her: “Well yeah, hence the term ‘open marriage.’”
            Me: (My conscience cleared) “Oh yeah. Well, I think you need to tell your friend that I am going to buy you a drink, then walk with me toward the hallway so we can make out.”
            Her: “Good idea.”

            Barb whispered something to her friend and took my hand.

            She was a terrible kisser. I thought that by the time girls reached the age of forty-two they’d evolve into decent kissers. Her tongue was moving so fast that kissing her became more of a task than a pleasure. When I was in college, a girl told me coldly, “Okay, you know what? You suck at kissing! Slow down and stop moving your tongue so damn fast.” I was baffled because I seriously thought I was good because my first girlfriend had said so. Since that day, I had adjusted my tongue velocity, and now I receive compliments all the time. Obviously, Barb’s men had remained quiet and tolerated her poor kissing skills. Thanks, guys.

            We made out in corners and on the dance floor only when her friends weren’t looking. After an hour of this, Ron approached us. “Hey, dude. I’m out of here.” The three of us walked to a table and discussed our desires.

            Ron’s desire: Leave. Now.

            My desire: Fuck Barb.

            Barb’s desire: Party with her friends until the bar closed. Fuck me afterwards.

            We didn’t voice our actual thoughts, but after much negotiating, Barb decided she wanted to dance with her friends until the place closed—in forty-five minutes—then call and “meet up with me.” Perhaps I should have stayed with Barb, ditched my sure-thing ride home, and taken my chances. For whatever reason, I believed in her “phone call afterwards” thing. I’m no expert on open marriages, but when I was stealing my dad’s Penthouse Letters, half the articles in those magazines involved true open marriage stories. I understood that women in open marriages don’t toy with sex. They take what they want.     

            As Ron and I drove home, I became anxious. After last weekend’s blown opportunity, I didn’t want another repeat. I considered having Ron turn around. “I’ll turn around if you want, man,” he told me. “It’s up to you.” I thought about it, but in the end I put my faith in Barb’s phantom phone call.

            When we got back to Ron’s place, I lay on the couch and dozed off. Ron has always had a slight apprehension about letting me crash at his pad. One time I had gotten so drunk that when I awoke in the middle of the night to take a leak, I didn’t know where I was. Although the bathroom was eight feet away from me, I went into the kitchen and opened every cabinet, trying to find a toilet. I eventually opened his front door and urinated in his condo hallway. The cabinet racket awakened Ron, and when he walked out to see what the commotion was, he saw me shaking out the last few drops in the hallway.

“Dave, what the fuck are you doing? I have a bathroom.” He wasn’t laughing.
            “Oh yeah,” I said, pulling up my zipper nonchalantly before going back to bed on the couch. Ron had to hose down the hallway. 
            For twenty-five minutes I was awake. No phone call. I had blown it again. All the “Penthouse Letters” reading had backfired. I passed out, endorphins unreleased.

            I awoke right away. It was Barb. I instantly reverted to bar mode, the brief doze merely a comma in the sentence of the night.


            “What’s up!” I made my voice sound wide-awake, ready to party.

            “Hey. I’m leaving now,” Barb announced.

            “Cool. I’m stuck.”

            “You’re stuck. What do you mean you’re stuck?”

            “It’s a long story. I’ll explain later. Just come pick me up. Exit Jamboree.”

            “Okay, but I can’t start my car until this fucking cop leaves. I’ve been waiting like seven minutes.”

            “Yeah, no hurry.”
            “So how do I get there?”
            I gave her directions and got up to take a leak—in the bathroom this time. I waited out front for her. It took Barb almost a half-hour. As soon as I opened her car door, she asked, “So what did you mean about being stuck?”

“I was stuck on the couch. I needed to find my bed. Thanks for saving me,” I said. She laughed. Off we went. 
            During the car ride to my house, Barb gave her anti-slut speech, “Okay, I’m just dropping you off.” Lame. For once, I would have liked a girl to cut the bullshit and tell me something like, “You better be good at sex,” or, “I’m going to fuck your brains out,” or “I’m going to drop you off, and then I’d like you to plow me.” Playing the part of the lying slut should be reserved for high school girls only.
            My room’s disarray was at an all-time low. It was so bad that I took her to the guest bedroom and tried to pretend it was my room. She complained it was too boring, so we used my room. She didn’t mind the mess. Clean rooms are overrated. My friends always ask, “Dude, how do you expect to get laid in this room?” The truth is: Most girls don’t give a shit about disorder the first time. It has yet to hinder a one-night-stand for me.

            Ron was wrong. Barb wasn’t “pretty thick.” She was fat. I hadn’t noticed it at Woody’s, but she was huge below the waist. While her fake breasts were gorgeous, her colossal ass actually made her waist look slim. Her legs were the size of a drinking fountain I once saw at a tennis court. I ignored it and fucked her anyway.

            As I nailed her from behind, her ass undulated like a tidal wave. I had never fucked anything like this girl. She had the loosest pussy of all time. The saying “throwing a hot dog down a hallway” wasn’t quite appropriate; it was more like throwing a flashlight into a Fun House. As I fucked her doggy style, a disgusting aroma permeated the room. I had noticed this smell, a combination of pussy and shit, on at least five different girls, all over the age of forty. It has only occurred while screwing older women from behind. I wondered what that’s all about.

My wise friend Axe later remarked, “Yep. That’s God’s way of telling them that they’re getting old.” 
           She left shortly after we finished, meaning I would have space on my bed to sleep in peace. Only if I plan on seeing them again do I actually want the girl to spend the night. If they’re insistent on staying, oftentimes I’ll actually lie and tell them I have a morning activity—parental visit, work, picking a friend up at the airport—at 7 a.m. If they’re shit-faced, I develop a conscience and make them stay. But Barb wasn’t shit-faced, and I definitely didn’t plan on seeing her again.


As Barb walked out, few words were said. She yelped as she nearly tripped over a duffel bag on her way out, her final words: “Well, I’m going to call my friends. I hope they’re at Denny’s.”

Twelve years ago I was the kid masturbating to Dad’s secret stash of porn. I lost my virginity in the passenger seat of my car nine years ago, and four years back marked my first rimjob.

             The older, wiser, sleazier me had an epiphany: I have become what I jerked off to. I am “Penthouse Letters.”

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