Article Thumbnail

The Milking Coach Is the Big Boss of Prostate Pleasure

When it comes to the slow, protracted dick and prostate stimulation known as ‘milking,’ there is no more qualified instructor

Have you ever been milked on camera?” 50-year-old porn creator Milking Coach asks a young, ripped stud e strokes his cock through the fabric of his flame-print jock strap. Wearing jeans, a black T-shirt and a matching baseball cap, Coach is comparatively dressed down. His short beard and glasses give the impression of an average, everyday guy, but as the clip trailer rolls on, it becomes evident that his jerking skills are anything but ordinary –– his subject writhes and moans with pleasure, panting “fuck yeah” as Coach massages his cock and oils up his butthole.

Clearly, they don’t call him “Coach” for nothing.

The nickname came around a decade ago, and it’s stuck with him ever since. “I was milking this guy who’s a couple of years older than me, and he started saying, “Yes daddy, yes daddy,” Coach tells me. “I said, ‘I’m not your daddy, you’re older than me!’ Without a beat, he said, ‘Sorry, Coach.’ That was the first anyone had called me that, and the name immediately fit. I was like, ‘Hell yeah, I am the Coach!’”

It’s hard to argue — in terms of the style of slow, steady masturbation known as “milking,” he’s a master. With 92,000 Twitter followers and a loyal subscriber base across OnlyFans and JustForFans, there are plenty of fascinated fans excited to watch him squeeze every last drop of cum out of his so-called “bulls.” (“Another milker taught me that term,” he says of the pet name he uses for his beloved milking clients.)

There are two types of milking that Coach specializes in: cock and prostate. “Cock milking is really slow, dedicated stroking — it’s not just jerking off,” he explains. “It’s about playing with different rhythms and different kinds of pressure.” It’s experimental in terms of positioning, too; in one video, Coach has a guy on all fours while he caresses his cock from behind, stopping and starting each time to ensure the guy doesn’t blow his load too quickly. Basically, milking is way more tantric than a regular jerk-off session; expect hours of edging, where Coach pushes guys to the brink of a cumshot and then stops them to drag it out longer.

Meanwhile, prostate milking involves stimulating the small, walnut-shaped gland found in the buttholes of people with penises (it’s sometimes known as the “P-spot”). “You don’t have to stick anything deep inside your butt to hit it, because the prostate is pretty close to the hole,” Coach tells me. “I like introducing prostate massage to straight guys, and then watching their faces as they get close to orgasm. There’s so much you can do to the prostate — rubbing it, flicking it, touching it and even pushing it.” Again, he’s a fan of the “all fours position”; in another video, he gently twists his thumb in and out of his bull’s butthole, applying pressure to the prostate while he slowly jerks him off.

Either way, in Coach’s hands, the results are always the same: With milking, the cum tends to dribble out slowly at first before intensifying into a thick spurt of hot jizz.

These skills have taken decades to master, but it all started when Coach moved from his home city of Atlanta to an all-boys boarding school in Upstate New York when he was 14. “I always got a huge rush from seducing the quote-unquote ‘straight’ guys,” he recalls. “I didn’t call it milking back then — I called it slow masturbation. I knew it was something their girlfriends would never do, so that’s how I would seduce these guys into it.” These formative years have clearly colored some of his fetishes today. “I can’t get enough of classic boxer shorts, because that’s what all the guys would wear between classes when they were hanging out in the halls.”

Even as a horny teenager, Coach was always a giver. “I enjoyed penetrative sex, but there was always something missing for me,” he explains. “I grew up in the 1980s with the fear of the AIDS crisis, so everyone was using condoms back then. I was a bottom, but I never liked the feeling of guys cumming inside me with protection. I enjoyed connections more with guys when I was the one controlling their pleasure and orgasms.” A dedicated voyeur, his arousal was perpetually higher, too, when he watched other guys reap the rewards of his milking hands.

Around 1997, he moved to L.A. with his long-term husband (they have an open marriage). Newly-installed in the porn capital of the world, he began practicing his milking skills on anyone who wanted to sign up –– and that meant jerking off numerous porn stars on their days off. “There are plenty of other milkers out there, but I definitely think in L.A. I became the ‘porn star milker,’” he jokes.

It was during this time that he also launched a small festival called “Milking Man,” basically “the milking version of Burning Man.” “My husband would go away and take the dogs with him, so I’d have the house to myself for the whole weekend,” he says. Keen to maximize this freedom, he started inviting his most trusted milking enthusiasts over for a weekend of no-holds-barred fun. “The Fridays were always pretty quiet,” he says. “You know how it is with events, people kind of forget that they’re on.” By Saturday though, every table, chair and bed in his house would have dudes sprawled across them, begging to be milked. “It was pretty simple: They come, I milk them, they leave,” he says nonchalantly.

Coach held five annual “Milking Man” festivals for his close friends, but word spread like wildfire; after the second year, he had to ask other milkers to come and help him out. “The last Milking Man before I moved, we milked 24 guys over a period of two and a half days,” he says. For context, these milking sessions can last “anywhere from half an hour to three hours” –– it depends how long the guy can last.

These festivals have been on hiatus since Coach left L.A. for Atlanta in 2017. When he arrived back in his home city, he couldn’t find work within his vanilla professions, no matter how hard he tried. He’d already sold a handful of milking clips on XTube, but in 2018, he decided to go full-time and launch his JustForFans and OnlyFans accounts. Since then, he’s racked up thousands of subscribers and fielded hundreds of messages from content creators begging to be milked by him. Even porn stars have flown out to be jerked off by him; earlier this year, he starred in a handful of studio films and recorded a sexy, milking clip for Himeros, the porn site of gay YouTuber Davey Wavey. “I used to go for older guys, but I milked a twink for the first time this year,” he tells me proudly of his Himeros scene.

There’s no telling how much of his fanbase is straight, but Coach is doing prostate-shy bros a solid by creating videos that are as educational as they are sexy. “For prostate massages, stools are the best for positioning,” he explains –– because they’re lower to the ground, they require a deeper squat and spread cheeks to sit on. “I just did a stool scene with this big hunk, and it was perfect. He couldn’t get enough; I needed more fingers!” 

The trick is to slowly slide your fingers inside your hole until you feel a small lump –– that’s your prostate. “Focus on your body and your breathing, and don’t pressure yourself,” says Coach when I ask for prostate-related tips. “It’s a bigger challenge to make a prostate orgasm happen.” If you’re using a sex toy, try one with a curve. “The curve is the key to nailing the prostate,” he continues.

Coach mainly produces and directs his own content and spreads it across different platforms: On JustForFans, he says, he can get away with “poppers and outdoor sex,” whereas the restrictions on OnlyFans are tighter. These subscription sites have become an outlet for his long-burning interest in film. “I took a directing class in NYU for a semester, and knew that’s what I wanted to do,” he recalls. “Now, filming as Milking Coach is starting to fulfill that desire: You know, I’m creating a film, editing it and putting it out. Granted, porn isn’t exactly what I thought I’d be doing, but I’m still getting that high from creating a film.”

As his follower count creeps up and his skillset diversifies, it seems the scope of his ambitions do, too. It’s too early to say what the future will hold, but no matter what happens, it’s safe to say he’ll milk it for every last drop.