An Ode To Prostate Milking

April 6 5 min read

If you type the term ‘milking’ into any porn site’s search bar, it’s likely you’ll find a deluge of busty, lactating MILFs with juice to spare. But scroll beyond these videos and you’ll find the occasional example of ‘prostate milking’, where guys slowly leak fluids as they play with their buttholes – or, in porn slang, ‘milk’ themselves. It’s a rarefied technique that dates back several centuries, but if you learn to do it well, it could change your sex life for good.


Even as our understandings of sex and our bodies are improving, there are still a few misconceptions surrounding what the prostate is and what it actually does.


Sometimes called ‘the male G-spot’, the prostate is a small, walnut-sized gland (part muscular tissue, part glandular tissue) which is basically there to secrete seminal fluids, which mix with sperm when guys cum. It grows as you age too, swelling gradually until it’s around the size of a plum. The Skene’s glands are sometimes called ‘the female prostate’ because research indicates they perform a similar function and create a different kind of orgasm when directly stimulated, but scientists are still on the fence – even in 2020, studies around female ejaculation are still pretty hotly-contested.


What we do know about the prostate – the male prostate, at least – is that it feels pretty damn good when stimulated. It’s hard to pin down their exact origins, but rumour has it that prostate massage techniques were first dreamed up by tantric sex masters across South and East Asia. These methods were thought to have all sorts of benefits: from preserving sexual energy and increasing libido to protecting physical and mental health, the prostate was treated as a one-stop gateway to wider fulfilment. 


The term trickled into Western medicine around the late 19th century, and doctors sometimes used it therapeutically to treat everything from erectile dysfunction to painful or difficult urination. This isn’t the case anymore, though – skepticism grew over time, so now it’s likely you’ll only get a prostate massage from an alternative medicine practitioner.


Naturally, the horniest of us aren’t just interested in the potential health benefits. Done right, a prostate massage can make you leak fluids for full minutes as opposed to the short, sharp release of a cum shot, and it basically feels like an ongoing orgasm – which, if you really nail it, can even be hands-free. It seems that most guys use prostate stimulation to mix up more conventional jerk-off sessions, but dedicating yourself solely to butt stuff can have incredible results, whether you’re using a toy, your fingers or a huge, phallic vegetable.


To find out how the experience differs amongst various guys, I compiled a kind of kinky, anonymous focus group. “Prostate orgasms are pretty freaking amazing,” one tells me. “It takes time and patience to learn how to do it properly, but it’s totally worth it. Plenty of straight guys enjoy prostate play, too – you only need to look at the vast number of strap-on and prostate toy offerings on adult toy sites to see how popular they are.”


He’s not wrong – in a recent Mashable article, writer Mark Hay recalls a marketing officer describing the ‘Great Prostate Rush of 2010’ as a turning point; as guys have gradually unlearned the shame and stigma around anal play, companies have increasingly popped up with more inventive, specialised new toys. Their sales have been steadily growing over the last ten years too, indicating that more guys are trying out prostate massage on their own terms.


These toys can be great when you get used to them, but if you prefer to keep it old-school, you can try it out manually. First, a few house-keeping rules: be sure to trim your fingernails, wash and dry your hands thoroughly and, if you really want, you can lightly douche first – it’s your body though, so do whatever feels comfortable. Slather your butthole and fingers generously with lube, and then slip your finger inside and out gradually, until you can feel yourself relax – a low stool can help with positioning. Soon you’ll be able to go from your first knuckle to your second and, finally, your third. This is when you should feel the walnut-sized holy grail, which is around four inches deep. 


When you finally reach your own personal lump of heaven, you’ll want to massage it carefully in either a circular or back-and-forth motion, whatever feels best. (Fun fact: the ‘milking’ refers not to the actual fluid, but to the action, which is likened to milking a cow!) Toys usually have vibration settings too, so experiment with what feels right to hit your own personal sweet spot. 


Patience is the key, especially if you aren’t jerking off, too – it can take a while to start leaking, but the whole process basically feels like a long, sustained orgasm. “I ‘unfortunately’ always got too horny and would jerk myself off before ‘letting myself go further down the rabbit hole’, so to speak,” another guy admits. The results are hot as fuck either way, but if you can stay the course, it’s well worth it. In fact, another kinky prostate fan tells me he once managed to get around 24ML fluids – nearly five teaspoons, if you need another measurement. Follow these tips and you’ll be wet in no time: if it’s good enough for ancient emperors, it’s good enough for you, too.

Jake Hall
« Jake Hall is a London-based freelance writer fascinated by everything from sex and sexuality to music and culture. » All posts →