If you’re older than maybe 25 or so, you might remember the dark, dark days before internet porn. Staying up late to try and catch a staticky nipple on Skinemax, sneaking into the attic to thumb through your dad’s sticky old issues of Playboy (which he swears he keeps for the articles), or just having to revert to your childhood imagination to take you to the top during your earliest masterbatory moments. It’s an understatement to say that the internet’s changed everything. Now you can go to a central hub of nothing but pornography and search for any fetish you could imagine – and there will be almost infinite videos there for your pleasure.

So one rainy day when we were a little bored and a little antsy to skate, when none of the million and one videos of POV MILF BJ’s would do the trick, we took the leap and searched for “skateboarding” in one of our favorite porn tubes. Of course there were lots of results, and amongst leaked copies of Away Days and a video of a girl nulling her void with our Jenkem x Lakai shoe, there were a few that stood out in their own special way. We wanted to share and review some of our favorites with you so you too can satisfy your dual appetites for sex and skateboarding all at once – no helmet or protection necessary!

“Black experienced milf teaches white skateboarding teen a lesson”

Did you ever have that neighbor growing up that yelled at you for skating near their house? We called my skater-hater neighbor “Jaguar lady” because she would stand next to her new Jaguar S-type and just stare at us to make sure we didn’t “ride” her car. Her house was in front a bigger than average manhole that I would always try to kickflip. I would usually only get one try before she’d kick me out, threatening to call my mom.

In this interracial porn clip, Mrs. Meadows calls over Johnny because she has to have a talk with him. As it turns out, Johnny has been skateboarding non-stop in front of Mrs. Meadows house and she can’t get anything done because of it. “Watching your tight young ass roll up and down in front of my house makes me masturbate everyday watching you.” Mrs. Meadows then begins to tell Johnny that he’s the same age as her kids, and Johnny stands in disbelief for he knows he pushes mongo and that that is not sexy at all. Despite Johnny’s poserdom, Mrs. Meadow gives Johnny everything he desires. Once Johnny gives Mrs. Meadow his “ender,” she tells him exactly what every skater wants to hear, “You can skate here whenever you want.”

As it turns out, the angry neighbor really doesn’t hate the skater, but secretly fancies them. Maybe if there was more open communication between skaters and angry neighbors like this, we could have saved places like Love Park or EMB with just a friendly blowjob. After seeing this video, maybe I had it all wrong too. Maybe “Jaguar Lady” didn’t hate us, maybe she just wanted to fuck us.

Check it out here.

“Kiss the rail”

Every now and then a skate video comes around that changes the way people see and use their skateboards. In the skateboard-porn web browser world, that video is Kiss The Rail.

In many quick, somewhat blurry gonzo shots, a woman is spanked with a skateboard by a masked man. The starlet then allows the wheels to roll over her, from her chest to her butt crack, as she masturbates to the sounds of the shitty bearings. She climaxes while a wheel rolls over her clit.

While I was surprised to see no rail skating, rail humping, rail-lingus, or any actual rail kissing (like the title suggested), this video did not disappoint. Sometimes when making a film, it’s easy to go with what is trendy at the time, like no complies and MILFS. You know these will sell, but sometimes when you take a chance and go with your creative (beer) gut, you get greatness, like a Gou Miyagi part or this tasteful little indie flick.

Check it out here.

“Sick skater bangs some gnarly moves on GF’s stepmom”

Gavin and his girlfriend, Ariana, are innocently skating around Miami, when Gavin tries to impress her by pushing faster. Of course he falls and somehow busts his knee open in grass, but luckily Arianna’s stepmom doesn’t have a job and comes to the rescue to pick them up and help clean up Gavin. But when they get home Gavin has forgotten their boards and Arianna needs to go back to the park to get them, which leaves the stepmom and Gavin alone.

The stepmom can’t resist Gavin’s bloody knee, and before you know it she is on her knees sucking him off to aid in his recuperation. Arianna comes back and the sneaky stepmom convinces her to help fuck Gavin. Before you know it they’re all inside one another. Seems like Gavin the skateboarder is living the dream, right?

Wrong. Despite the video being titled “Skateboarder bangs GF’s stepmom,” after watching this you realize that Gavin isn’t really a skater… Ariana is the true shredder.

The first minute thirty of skating in the video is pretty much all Arianna cruising, and then Gavin comes in and immediately busts his ass like a poser. It is Gavin who forgets the boards at the park that Arianna has to go back to. Arianna probably wants to stay at the skatepark and work on her lines, but she knows her slutty stepmom can’t keep her hands to herself. And even when Arianna gets convinced to have a threesome with her stepmom and Gavin, you can tell by the look in her eyes she’s just thinking, “Dammit Gavin, just cum already, I wanna get back to the park!” Even in porn, female skaters are not getting the credit they deserve!

Check it out here.

“Skater Fucks Blonde MILF”

This is one of the worst generic porno plot lines I’ve ever cum across, and Peter is one of the worst generic skateboarder characters to ever be created. He is dressed in early 2000’s “wigger-wear,” knee pads that are on his shins, shitty athletic adidas sneakers, an old-school (pre-Welcome) shaped board, and one single wrist guard which he keeps on during sex (I’m assuming from a terrible benihana fly-out injury). All this plus that terrible generic porn acting where Peter goes from being a virgin seeing boobs for the first time to going down on her like a pro to laying some serious pipe on his best friend’s AARP gold member certified mom. After the cum shot, the milf tells Peter his is now a man and the screen fades to black.

Despite the aforementioned issues, I was surprisingly left wanting more. I was there with my dick in my hand wondering about the inner lives of the fuckers I just watched. Will Peter continue to skateboard? Will he ever drain that pool? I can’t believe he can actually kickflip! And where the hell is this George they keep talking about, is he banging Peter’s mom? I can’t answer these questions, but I can only hope that Peter is now George’s step-dad and that they skate that pool everyday.

Check it out here.

“A Skateboard gets more action than me”

There is a slow growing trend of videos of girls who sit on skateboards and just masturbate. Some do it shirtless, some do it completely naked, and some do it completely clothed. Most skaters know that a board is not something that is very comfortable to sit on for a period of time, nonetheless masturbate on it! Like, who was the first person to say, “I want your barebutt on some Mob grip while you’re flicking that bean towards my direction, baby! I got tokens coming your way!” But for what these videos lack in creativity they make up for in novelty. I mean, they’re literally taking the skateboard to places never considered enjoyable before.

In “A skateboard gets more action than me,” a fully clothed woman gives herself a controlled “credit card” outside while trying to to enjoy having the razor tail of her board jabbed into her crotch. While some skaters dread the accidental gooch swipe, this woman seems to enjoy it, inviting all 9 plies right in to her moist and sweaty swath. Whilst I don’t know how big this trend will get, I do know that this girl is breaking barriers and finding new ways to work with your board, even when the board doesn’t want to work with you.

Check it out here.

“PUNK SKATEBOARDER LATINA NAMED DIANA DELGADO GETTING HER TIGHT…”

In this video, the cameraman finds a girl at a skatepark where she is practicing her ollies, half cabs, and fakie front shuvs. After some convincing in what I assume is spanish, we find her naked behind the skatepark banging a stranger. In the middle of the video, she takes a piss on the floor and then gets back to doing it.

While I was watching this, I wasn’t thinking about how I would love to date a skater girl, or how there should be more pornos that start with someone picking up a girl at a skatepark. I didn’t even wonder why she peed on the ground in the middle of the video. Instead, I began to wonder when the tables would turn? Will the male dominated skate world ever become equally dominated by women? And how will this change porn with skateboarding in it?

Maybe in future pornos, roles will be reversed and girls with backwards caps and Nike SB t-shirts will be on the prowl for guys. They’ll pull up to a skatepark where there’s a Team Handsome member skating and say something like, “Hey shrimp dick, let me see a kickflip.” After offering to show him PJ Ladd’s unreleased Plan B part in their bus, the guy will get on only to find out there is no such part. Then the ladies will have their way with him, and when they’re done, they’ll kick him off and yell, “I’d rather watch Gino push than fuck you again!” right before driving off into the sunset. That’d be a nice change…

Check it out here.

Words/Research: Russell “the Intern” Dolan
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