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When Thinking You’re Going To Bang Your Friend’s Stepmom Goes Horribly Wrong

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When Thinking You're Going To Bang Your Friend's Step-Mom Goes Horribly Wrong

As a parent, Mrs. Carlson was about as attentive as Casey Anthony. She was wife number two, a goddess of silicone and jewels, with the sort of carefree attitude that only an infant child and lack of prenup can afford a former mistress. She was my dream conquest, though the wife of a “diamond” salesman (though his “diamonds” made more widows and orphans than wives and families, I’ve heard) and the stepmother of a former slam I’d jackhammer fingered as if Pornhub “romance” was how real girls like to get plucked.

But things had changed. I was tier I now, a college graduate of my freshman year. I had fucked, horribly disappointed, and bought plan B for a bevy of women, probably totaling at least an hour of total intercourse. In my mind, I was ready to tackle my first cougar, and I was hunting trophy game.

Lord of War was a major problem, though, as he refused to let us pillage his castle, his daughters, and, of course, his wife. Even throughout high school, the mecca of opulence that is their penthouse remained untouched — not a single party, not even a dip in the rooftop pool. So when Kara (step-daughter) texted me she was “having people over to the upper east side house” I knew pops was somewhere in the Middle East wearing a Burka.

While I realized I had absolutely no shot (or so I thought) of mounting Mrs. Carlson, the swinging dick delusion a couple shots of vodka incites from your virgin liver to your near virgin balls transported me back to a world of totally unwarranted optimism. I had been working out, I thought. She was married to a guy with an AARP card — I could do this. Or at least I’d go full James Deen on the stepdaughter.

I made my way uptown with a Dasani bottle filled with vodka tonic acting as literal fuel to my fire of arrogance. I finished the bottle, threw security a wave (which absolutely did not work, so I sat in the lobby waiting for a girl to come down and get me), and made my way to what must have been a set from the Wolf of Wall Street. Paintings, antiques, and crystal chandeliers. I knew war paid, but not this fucking well.

Sadly, the apartment was the sexiest thing at the party. In horror, I realized the “freshman fifteen” was not Bigfoot, the abominable snowman, “Nessy,” or the stuff of legend — it is very real. While the women at the party seemed to be midway through their first trimester, I saw Mrs. Carlson by the pool with a martini and a cigarette. Like the glowing eyes of Dr. TJ Eckleberg, she watched us, though in my mind solely me, all night, drinking and smoking and probably contemplating what it’s like to finish a blow job with a load of dust in her throat.

At this point, my substance-induced delusion had served to not only inflate my self-confidence to a level of total irresponsibility, but paradoxically lowered my standards. The bloated beauties in front of me now just had “bigger boobs,” “were probably freaks,” and “actually might look better now.” In my heart, I knew none of this was true, because as this year’s SI Swimsuit cover showed: bigger is definitely not better.

But it was late, options were slim, and two weeks away from the frat castle had me questioning the legitimacy of my imagined sexual prowess. I stalled until I was at a point my drunkenness relieved all insecurity, or concern of consequences to my reputation, and I was ready to make a move.

Just then, I noticed Mrs. Carlson motioning for me to come outside. In shock, I approached the door to the pool area.

“Hi, can I help you?” sounding like the mongoloid who opens the door for you at Target was the best I could muster.

She smiled, took a sip of her drink and said, “Come out here.”

I was convinced this was my Stiffler’s mom moment. I was hammered and she had drowned herself in enough Dom and straight martinis to paralyze the judgment of even the most convicted alcoholic. I sat down with my heart pulsing in my chest and pants.

“I need your help,” she said. “I don’t know who these kids are they invited here, but it’s late and I want them out. You can stay, and a few others. Use the pool if you want. I don’t care. But tell Kara and Katie to get everyone out.”

That’s fucking it? I thought. Fine — I’ll endear myself to this gold digging curmudgeon. I went inside and cleared out the population.

Within 20 minutes or so, it was down to a handful of us, but inexperienced drinking (I thought the fact that I drank my Smirnoff with coke made it a “good mixed drink”) led to illness and the sort of uneventful night I probably should have expected. I was about to leave when I noticed her motioning me to the pool deck again.

I sat down across from her, swaying from what had morphed into a spin-induced nausea.

“Have you ever had a real martini?” she asked.

I lied and said yes.

She poured me a glass straight from the shaker and took another puff of her cigarette.

“So how’d you like your first year in (city removed to protect anonymity)?”

“I loved it, great school.” I struggled to formulate sentences.

“I bet you met a lot of girls out there,” she said. “You’re cute.” She took a sip of her drink as I tucked the raging flagpole safely in the waistband of my pants.

“I met a couple.”

She stood up. “I’m going to go for a swim. Tell the others they can use the pool. I don’t know why you guys have been inside. It’s a beautiful night.” She put out her cigarette and slid off her cover up, unleashing a bikini so far up her ass I doubt she’d even notice me inside of it.

“I don’t have a bathing suit.” I idiotically proclaimed.

“Suit yourself,” she said as she walks in.

This was a watershed moment in my life, to say the least. The others were asleep or dry humping somewhere in the palace. It was just the two of us. I knew I had black boxer briefs on, that I was raging hard, and, in reality, there was no way the Duchess of Diamonds would risk her life of opulence for 17 seconds of me. I needed to just go home, pull up the hub, and move on. It was not the fun thing to do, but it was the right move.

And, of course, I slid my pants off and stumbled my way toward the pool instead.

“I won’t look!” she laughed turning away jokingly.

Once I was in the water I knew there was no turning back. Her flotation devices wet and glistening in the starlight, I moved closer to her. She lit a cigarette by the pool stairs and I continued lurking like a shark, somehow forgetting my reality as a minnow.

I slid next to her on the wall and asked for a cigarette. She laughed. “Are you even 18?”

“I’m actually almost 20,” I said.

“Oh, so you can handle yourself with one of these then?” she asked, handing me one.

“Yeah,” I responded, sliding my hand between her legs, “and one of these too.”

Now here is where I’d like to tell you I put her on the side of the pool stairs and railed her the only way I knew how: hard, fast, and in missionary or doggy, how she gave the best head I ever had, her reconstructed vagina was like a wonderland and her dot sized nipples expanded like push pops while I rained all over them.

But that would be a lie. “What the fuck are you doing!?” she screeched, simultaneously removing my hand and slapping me worse than the “pledge paddle” ever could. Her handprint branding me like the scarlet letter I deserved, she jumped out of the pool screaming profanities and threatening to call my mother. “Get the fuck out!” she screamed as she entered the house.

There I was, alone on the roof with my traumatized frock retreating like the French at the first sign of war. I had taken my shot, stepped up to the plate with my veiny bat, and struck the fuck out.

I blame the “you miss every shot you don’t take” poster we had in the house.

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Siblings of Mark Wahlberg

Sorry Mom & Dad. Follow me to prevent my suicide: @SiblingsOfTFM

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