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Home > Features > Cruising for Sex on a Skateboard

by Skaterboy Chris

Old T-shirts and baggy work pants draped over toned, tattooed or pierced, boxer clad bodies are good indicators that you've got a skater in your midst. He'll be wearing Airwalk sneakers, usually, and have either no hair at all or very shaggy (even long), messy hair. The skater craze is more than a sport or a fad, though. It's a lifestyle for many, and it's attracting guys and girls from almost every age group and educational background.

Everybody is mesmerized by the skater -- it's not just the fancy tricks on his board (some can hardly skate at all) -- it's attitude; his walk, his talk, the ultimate display of his boyish masculinity, fearing nothing that crosses his path. Simply put, the skater has replaced the gang-banger in many gay men's sexual fantasies. The 'rough-and-tumble' edge of the skaterboy make for the perfect 'wrestle me down' sexual experience. The question (more so the lustful desire) of the day is, "How do we get 'em?"

I've been skating since before it became a lifestyle. I've watched skating transform from a mode of transportation (I rode my board to school everyday for six years) to a competitive sport, and then to a complete lifestyle. I live amongst the skaters -- I carry my board with me almost everywhere I go, and I know I've always got other guys to thrash with anytime I want to take the edge off. Sometimes, though, I need more than to just take the edge off, skating around a parking lot -- I can rely on other skaters to release sexual tension, and so can anyone else who really gets into skaterboy like I do.


It's very important to first understand how to identify skaterboy; many gay men lump all guys who wear baggy clothes into the same lifestyle, but there are several subcultures that wear this type of clothing. Skaters do not always carry their boards with them -- some guys who carry boards around aren't even skaters, for that matter. You've got to identify the lifestyle of the skater to find him.

"'ll find that the majority of skaterboy are usually more than willing to play with other guys. Some of them will be very open to the notion; bisexuality is 'cool' to these guys."


True skaterboy are normally thin, and very agile. They're not carrying any extra weight in the muscle or fat departments, and the majority wear old, baggy, worn clothes purchased at thrift stores. Even the Airwalk sneakers they wear come straight out of thrift stores. These guys will not be materialistic, and may not own much more than you see them carrying around in backpacks. This lifestyle is the product of the 'Grunge' and 'Alternative Punk' lifestyles, and they don't wear anything flashy. Basically, the rule of thumb here is if you see a guy wearing something that looks like it's off the rack at Macy's or Nordstrom, you've got the wrong guy. A guy wearing newer, expensive designer garb will probably also be wearing fat tennis shoes (usually bright white) -- he's a 'raver,' and he will be sporting some type of trendy hair cut.

Once identified, you'll find that the majority of skaterboy are usually more than willing to play with other guys. Some of them will be very open to the notion; bisexuality is 'cool' to these guys.


The best way to hook yourself up with a skaterboy is to frequent the hangouts. Skaterboys normally don't have sex at the top of their lists when they're thrashing, and you won't find them out cruising very often, either. Skaters are not exactly sexual predators; coffee shops, book stores, and mall food courts are good starting points to meet and watch them work their magic. After the malls close, you'll find many in parking lots everywhere. Night time thrashing is best, because traffic is lighter and there's more space available.

You'll need to wear non-threatening clothing -- looking too 'preppy' or clean cut will surely strike you out. Don't rush right out to the nearest thrift store and buy a whole new wardrobe either; you'll just end up looking like a 'wannabe,' and get nothing more than a few scoffs from the boys on the boards.

The boys you'll have most luck with will normally be walking or sitting alone. If they're hanging out with several other skaters, chances are very slim that you'll find any real action (though you'll probably find many opportunities for serious eye contact). Groups of skaters go everywhere, including the restroom, together; it's usually difficult to single one out and get any vibes back from him.

Look for skaters walking along the road, waiting for a bus, or sitting at a coffee shop alone. If you're at the mall, look for singles at the food courts; most skaters already know that many gay men cruise public rest rooms. There isn't a skaterboy alive who won't at least give you a free peek at the urinal; they love being watched.

Another good way to attract a skaterboy attention is to slip a copy of Thrasher magazine (the best and most popular skater rag around) in your back pocket, and walk passed him. If you play your cards right, and slow down just in time, you'll end up eye-to-eye with the curious fellow. Sitting at an outdoor coffee shop table, reading this magazine is another way to spark some curiosity. He'll usually ask if you skate (assuming he noticed the magazine), and strike up a conversation from there. If he starts talking to you, there's really nothing you can say to lose his attention so remember to remain calm, relaxed and confident. If there's one thing all skaterboy like, it's other confident guys to hang with.

Spotting Skaters Who Want Sex

As much as it's cool to skaters to be bisexual, not every guy is into other guys. Keeping respect and good manners in mind, don't approach just any skater and expect him to drop his pants for you.

The majority of skaterboy do not suffer from any type of sexual identity crisis -- they're usually hard-core, tough guys who are willing to try almost anything once. Unfortunately, most men feel that skaters are unapproachable, because of this tough exterior. They assume that skaterboy are straight, and only fantasize about them. The truth is that skaters are driven by curiosity; they love to take things to the extreme and go to the limit in almost everything they do. The key is all in approach.

There is no etiquette to cruising skaterboy; that's the big secret, and the main reason men fail so often in finding any fun with them. Traditional cruising methods do not work with skaters, and should be immediately stored away while you're on the prowl. This is not the forum to use the familiar squeeze of the crotch, tap of the foot under the stall, or even the less conspicuous, "Do you have a smoke?" line. Trying any of these methods will leave you tapping your foot, groping yourself and smoking the whole day long.

Skaters expect to be approached, but don't want to be bothered with senseless conversation about the weather. They love compliments, and they shine for audiences. Sit back and enjoy their shows, listen to their conversations, and let yourself be noticed by them. If you sit too far away, you'll get nowhere.

By now, the overbearing question of the day is, "How do we know if a skaterboy is approachable?" The answer is that we don't. Skaters don't follow a code; they don't use labels very often, and they don't usually cruise for sex. Some skaters, however will sometimes take a liking to gay sex and find the local cruising spots for some fun. The bad news here is if you've got a taste for skaterboy, you've got your work cut out for you. There's just as much chance of scoring with a hitch hiker as there is with a skater; it's all in how you play your game.

Skaters are into eye contact, and they often check each other out. A typical sure sign of interest is when a skater makes eye contact, checks you, then makes eye contact again. The ritual usually starts from a ten to fifteen foot distance between you, so you won't have much time to ponder. This scene calls for quick judgment, but it's also nearly fool proof.

One final note on spotting. Discretion and caution should always be used when cruising any unknown territory. Remember, you're on a skater's turf; use your good judgment and respectfully bow away when it's appropriate. Don't make cruising your obvious reason for hanging out, staring at that one skater; you'll make him uncomfortable (and probably the butt of a few jokes from the other guys). Of course, always remember that there are homophobes and fag bashers in every subculture you'll encounter -- if he looks too tough for words, he probably is. Leave him alone.

How to Have Sex

Just like cruising, there is no etiquette to skater sex. Skaters are just as varied as any other guy you'd pick up in a bar. Obviously, you'll meet some skaterboy who have been around the block, so to speak, and other times you may find a guy who's trying it out for the first time. These guys will not have any hang-ups about you asking, if they don't just say what they like or don't like. If he's new at it, he'll just respond accordingly. The one thing to count on is that you'll almost always need to provide your own protection. Other than that, skater sex is your basic free-for-all.

The Down Side

Because of it's very nature, I haven't met any guy who was disappointed by any form of sex with a skater. Most men feel that skaters are so unapproachable that if and when they score with one, it's a great conquest, regardless of what they did together.

A looming disappointment, however is that you'll often find that you may expel much time and effort cruising a fine skaterboy, only to discover that he has no interest whatsoever. It's always recommended to determine early on whether there will be any sex. Remember, there isn't much need for beating around the bush with these guys.

Again, use caution when confronting any man for a sexual rendezvous. Skaters almost always require direct communication, but that can backfire. You don't want to risk your health and well-being for some afternoon dick. If you are doubtful for any reason, or feel that he may object, quickly depart from the subject or the situation entirely. Don't take any unwarranted risks.

You'll almost always need to provide all of the accommodations, as well. Skaters don't usually live alone, and if they did, wouldn't want just anyone knowing their address. They'd much rather sit back in your car or go back to your place. They won't be very concerned about cleaning up afterward, so you won't need to offer the use of your shower facilities, but they'll appreciate a ride back to meet up with their friends.


Rough, uninhibited, raw sex without any hang-ups or limitations.

Author's Notes

I've used the term, 'skaterboy' loosely throughout this article; let me assure you that in no way am I referring to boys under 18 years old. Skaters come in all ages, and races (though are generally white), but we are all skaterboy. In no way, should any reader assume that the author condones sex with minors. I'm a 24 year old skaterboy and writer in San Jose. I've been skating for 13 years, I love the thrasher lifestyle, and have been a writer for ten years. No part of this article is meant to belittle, insult or otherwise offend any individual, especially other skaterboy.

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