Men wearing heels. In secret? Let me tell you, there’s never a dull moment when you work as a pro male dominant. The month of May has a tendency to be quiet in our trade; I’ve often wondered if it’s because there’s three Bank Holidays in quick succession, Easter May & Spring meaning your average punter has less ‘discretionary spending money’ what with ‘family obligations’, summer holidays to pay for, etc. There’s no doubt too that the UK economy is shrinking fast, and the sex trade is one of the first sectors to suffer as evidenced by the ‘Stripper Index’. It and the road transport industry are closely monitored by economists, why? In the case of the latter its because factories book haulage for ‘Goods Out’ and if UK Manufacturing ain’t making as much as they were, there’s a fall in traffic. It’s one of the first economic indicators to show. Both industries are ‘canaries in the coal mine’ so to speak. Remember when we used to mine coal? Probably not.
There’s another saying too; ‘Sell in May & Go away’ pertaining to the Stock Market. Some of y’all know that when I’m not working in the adult industry, I spend nearly all of my time studying charts, economics & politics aka ‘macro’ matters. You’re YAWNING right? Each to his own, but I’m forever driven, focused on staying ahead of the fold & building back bigger & better following the sale of the Darlington Dungeon. But I digress.
May 2025 has bucked the trend, for me anyway with a good number of sessions as a pro male dom, and a couple of hot male escort meets too. One client, during a consultation recently, confessed he was ‘fascinated by escorts’. He wondered how as a group we managed to deliver, to whoever, without even seeing as much as a photo beforehand. That’s a good measure in itself of a service provider’s experience in my opinion; if they ask you for a photo before meeting its a sign… they’re probably inexperienced & doing it ‘part time’ for cash in hand. I/we did it ourselves decades ago, before going professional. When you’re a pro, you learn to never judge a book by its cover…everyone HAS SOMETHING to offer, you just gotta be skilled enough to dig it out and capitalise on it. The client told me he could never meet ‘just anyone’ let alone have sexual activity with them. I shared with him snippets of info about ‘previous’ experience, including seriously obese guys, guys with micro penises (less than an inch hard in one case), all kindsa stuff. When you’re experienced you know what buttons to press to GET A RESULT, IE the client leaving satisfied and hungry for more. In our trade, you DO ‘kiss some frogs’ but on the flip side there are meetings that truly stand out for all the right reasons in that they’re smooth and erotic, & flow beautifully without being micro-managed; kind of instinctively natural. It’s why I’m hitting the keyboard, you can be a ‘fly on the wall’ so to speak, during a recent meet with a guy I’m gonna call Dave. (for the sake of anonymity)
Dave’s a fifty two year old estimator from Bristol, up in the North East working on some kind of contract at Teesport.
He’d come across me on X (formerly Twitter) and messaged me privately about men wearing heels. There’d been a couple of false starts, with his firm sending him to other places at short notice, but one day last week the stars aligned, with Dave calling me from a holding point, eager for directions. Now some guys have their brains in their pants.. understandably so… a mixture of excitement, fear, arousal what have you, causing them to instantly forget half the instructions & lose their bearings. They’ll routinely fly past the road end, calling back a little sheepishly to say they’re lost. Not so with Dave though. Right from the off he’d been a good communicator and in no time at all he was parked in the driveway. Commending him on how quickly he’d got there, he admitted to writing down directions on the pad I’d told him to bring with him, to ‘make things look business-like’ to neighbours. To be fair, most of the time said people are out at work, but you know how it is…’mushroom syndrome’…feed ’em shit and keep them in the dark. Its worked for me, over many years now.
Dave stood around six foot tall, slender, and tanned. For 52 he looked good. Very good. His job kept him on the move and it showed, with a healthy complexion & not an ounce of fat; pretty impressive for some-one forever travelling & having to eat out most of the time. I’ve seen three other guys in the last few weeks with similar jobs, all of them north of thirty stone in weight, due mostly (according to them) to sandwiches and pies snatched ‘on the hoof’. So *respect* to Dave.
He was booked in for ninety minutes, so after a brief consultation we headed to the bathroom next to the play suite. He needed to douche so he could relax and enjoy anal play with no nasty surprises. He’d told me he had a huge high heel fetish and wanted to wear stockings. I’d got him down as a sissy slut, but that wasn’t really what he was. He was a man with a heel and stocking fetish. ‘Men wearing stockings’ I hear you ask? Jump on Google and you’ll find 169 million others ask the same ‘Why do some men like wearing stockings?’ Twenty Six million others want to know ‘why do some men like to wear heels in secret’. It’s a complex and very interesting subject in itself and not for the reasons you might think, find out more in the footnote.
Once he’d prepped, I introduced him to Public Enemy… a shiny black electro cock cage I’ve only had a month but already proven a BIG HIT with clients. It’s quite a sturdy piece, let down by a flimsy pin which secures the ring, so care has to be taken fitting it. Clearly Dave was excited by the prospect of being locked up, evidenced by his cock swelling… he appeared to be a big boy. If it grew anymore it would be problematic for sure in that he wouldn’t fit in the body of the cage, however first things first. Patience is the name of the game when it comes to chastity devices of any kind. Too many guys throw a hissy fit and give up; knowing this I fore-warned Dave… his cock WOULD FIT, all we needed to do was take time, maybe use a little talc and not too much lube. Once you get lube all over the shop you’re bound to struggle. Pretty soon he had the ring around his scrotum and in place ready to be latched, then it was on with the top cover and insertion of the pin. Still, his cock was WAY too big for the cage itself; I told him if it got any bigger I’d beat it, then relented a little, telling him to ‘hang fire’. Grabbing some ice cubes from the waters in reception I rolled them over his bellend, enough to shrink it to fit. Voila! Caged in chastity. Next, I showed him a range of heels I’d got lined up, silver ones, a couple in patent leather, another pair in plain black, but none were deemed high enough. So I rummaged further, and brought him some five inch Oxford’s. 
They met with his approval. In truth, they’re MY faves, normally ‘reserved’ for when I’m in SWITCH MODE. I don’t always make them available not least because few *men* can walk in them! We’re (Tees Valley Mistress and myself) always adding to our collection, so it isn’t often we come up short. I had another pair of brand new size 10’s stashed away, they’ll be for next time. Once I’d helped him on with them and laced them up, I suddenly remembered ‘STOCKINGS!!!’ Doahhhhhhhhh! Forgotten! No matter; it just took a couple of minutes to remove the shoes, roll the holdups on and refasten and we were good to go.
I ordered him to stand tall and reach for the chain loops hanging from the frame of the bondage bed. He’d told me he wanted to be collared so I secured him with a camouflaged item from COLT, attached to a chain leash. I allowed it to hang loose, while I inspected him from a distance, probing his naked body now and then with a cane, lifting his balls with it, trailing it across his backside and around his crack. Then, getting up close and personal from behind, I reached around to his nipples, twisting them quite hard, before gently rubbing them until they were erect. Nipple sensitivity is like a litmus test for sexuality… always a good sign if a guy’s nips are sensitive and he knows it. It’s an indication of latent ‘bi-ness’ and an open mind forever pushing boundaries & hungry for exploration, with the ultimate goal likely of ‘see how far I can go’ culminating in (for a lucky few) a FULL BODY ORGASM. I say ‘few’ because its like everything else in life worth striving for…it requires practise, and work. You can call me crazy, I’m just sharing observations of men now running well into four figures over thirteen years. Interestingly, just this week, I saw similar notes from someone else, regarding patterns in fingers and hands pointing to a person’s sexuality.
Dave appeared relaxed…
‘Gas mask?’ I asked him
‘Yes please’ he replied.
Reaching for the Cold War military gas mask hung from the fucking bench, I remembered to remove the blanking plate and unscrew the bottle attached to the hose; it feeds p*ppers direct to the face mask via a pressurized line operated by a hand pump. Pouring some Fist Fuck onto a rag, I inserted it into the jar, screwed the lid on, then fitted the mask. Dave’s head was average size so there was no problem fitting it, the straps snapped shut with ease… ‘You okay Davina?’ I figured it appropriate to ‘feminise’ him at this stage. He’d told me while we were prepping that ‘heels felt good‘ & ‘they made him horny’. He particularly liked the feeling in his thighs & knew that was one reason why women wore them; I could relate to that too.
‘Yeah’ he replied, muffled by the mask….
‘Yes what?’
‘Yes Master!’
‘That’s better. P*ppers, are you getting ’em?’
‘Mmmmmmmmmm’ was all he could manage between slow deepening breaths, as he inhaled, helped by me pumping the bulb. Leading him away from the bed a couple of feet gave me room to sit down, and start playing with the 2B connected to the chastity cage. He was steady on his feet, giving me confidence to start twirling the knobs of the electrostim unit. He was feeling it. Time to get more comfy. Helping him onto the f*cking bench, I got him on his back, positioned a cushion under his head, then threaded his legs through the stirrups so the backs of his knees were supported by them… putting tension on his body, allowing his ass to overhang the bench, always a good place to be when stimming. Next I returned to his teats, fastening a couple of heavy duty suckers to them, then turning the screw anticlockwise two full turns until the nipples were pulled well up into the glass, like mini tits.
Picture him if you will, high heels, legs in lacey topped holdups bent at the knee and supported by the stirrups, chastity cage on, gas mask tight but fumes from the ahem ‘leather cleaner’ drifting into the room, his hands secured by purple cuffs to the base of the bench but cross chained too so he couldn’t fiddle with them, well and truly secure, at my mercy. Mindful of Google’s policies, I’m reluctant to post pictures on this site, preferring to keep it fairly ‘vanilla’; if you’re on X take a look. While you’re at it please like, follow, retweet and enjoy! With the 2B now resting on his torso I upped the power incrementally, notch by notch in between massaging his hole through gloved & lubed fingers. He wasn’t especially tight, but probably not loose enough to take a cock; he was an anal virgin apparently. It seemed his experience with other men was fairly limited. He later identified himself as ‘bicurious’. Master likes to hit the spot aka the prostate. Many men have never been there. I derive satisfaction from coaxing pleasurable feelings in the recipient the likes of which he may never have previously experienced. Often, its the cock that does the talking, in the form of dribbling precum, in Dave’s case a thread which never grew beyond around four inches, gradually thickening, but not so much to lengthen. There it stayed, even when I started to fuck him more deeply with increasingly bigger dildos. I’ve several, made of glass and steel; the ones men seem to like the best are the big beady ones. The trick is to gently ease in and out at the point where there’s a change in circumference. The feeling can be VERY intense prompting some men to beg to be fucked. But that was not to be in Dave’s case. I had other things in mind. Remember at the start I said how the meeting flowed and how it felt so natural. Intuition is the ability to understand something instinctively, without any need for conscious reasoning or explanation. One thing just led to another… Unfastening him from the bench, I pulled him up, spun him around and got him to lay on his tummy back on the bench, supported by a cushion under his chest. Still wired to the estim unit I placed it on the bed, removed the gas mask and replaced it with a satin hood. It has two eyelets for the nostrils and a zipped mouth, which I opened ready…for you know what. Holding the p*pper bottle now in my hand, I encouraged him to breathe in deeply while removing my leather trousers. Underneath I wore a black satin thong. Turning his head to one side, I pulled it towards the bulge, curious as to his reaction. He didn’t shrink away… to be honest there wasn’t much there at this point. I’d been so focused on him I’d little chance to get aroused much myself. The bench is a heavy duty unit, with an extra overhanging section I specified when new. It enables me to get on the bench WITH the client, facing him, hanging on to the stirrups with my hands, legs around him, my cock close to his face but still covered. Encouraging him to muzzle his head into the cloth he felt me harden. ‘Mmmmmm, master loves it this way, loves to have his cock sucked……here…..’
Pulling the thong down exposed my still flaccid member, no more than three inches in length. When it’s floppy, its quite fun to maneuver it towards and into a subby’s mouth. The guy has no clue if ‘that’s it’ or what…prompting me to mark them out of ten on their ability in the fellatio department. Inexperienced guys usually go headlong into it, sucking strongly with no finesse at all. The scoring focuses them though… they strive to go from a five to six; pretty soon they get the message, encouraged as they get marked up higher and higher. Simultaneously my cock is extending, beyond their expectations in most cases, and so it was with Dave. To be honest, it surprised me too. It got really big for me anyway. Months pass sometimes & I/we seldom see anything much more than 5 inches hard. I was nudging seven and totally turned on…to the point of wanting to cum hard…..
I asked him ‘Do you wanna taste Master’s seed?’
Dave shook his head…and that was fair enough; I wasn’t even sure if he’d ever sucked a real cock before now, besides time was flying by at a rate of knots. Unbelievably an hour had already passed. Pulling on my leathers, I got behind him again, upping the power on the 2B. He wanted the milking machine but I told him he wouldn’t be going on it unless the precum touched the floor. So much has gone on this week I didn’t find time to list on Notepad the precise sequence of events for this part of the meet, it’s a little blurred. Suffice to say, Dave’s level of arousal continued to grow, and with it that sticky thread, until it touched down at floor level. I commended him for his effort, as it began to pool on the laminate, signaling the time had cum to be milked for real.
I’d positioned the SeriousKit penis milking tubes and gone through the checks before he’d arrived. Clearing the bed, I got him spreadeagled and secured tightly in cuffs. Firing up the pump, I told him not to panic as the machine proceeded to draw him in. We weren’t sure if he was ‘between sizes’ and needing the bigger tube, but the 40mm SPT seemed just right. His cock filled around 50% of the height of the tube initially, but the moment I increased the suction, it grew another 25% or more, almost filling the tube. I’ve found little to moderate vacuum with pulsation adjusted to a level just shy of stroking, ideal for initial stimulation. The recipient has to get used to the feeling, and if it comes and goes so much the better, because each cycle is a step higher. Moving to Dave’s side I began to work on his nipples, with fingers, and a pinwheel as well. Offering him p*ppers just before I switched things up a bit got him even more ‘wanting’. I moved back to his bum, thrusting into it back and forth with the bulbous glass dong faster and faster… ‘Milk me MASTER!’
‘What was that?’
‘MILK ME MASTER!’ he repeated, a note of desperation in his voice….
The machine kept going; Dave started to cry out. I never know whether they’ve cum or not…occasionally you see the explosion through the Perspex other times it just get’s whipped away such by now is the strength of the suction.
I carried on regardless….hopeful I’d get him to a second climax. He must have softened quite quickly though because the tube broke loose, spilling lube over his balls and the pvc sheet placed beneath him… ‘I’m done’ he cried before I could get him sucked in again….
And that was it! Sadly. We warmed down briefly before he got showered & dressed, regained his composure and bid farewell, another happy Chappy! A couple of days later he texted, thanking me, & I told him I’d be writing about the meeting, hence this post. He seemed pleased. I hope to see him again. He has masses of potential. It was the fifth meeting in as many days.
Perhaps you can see now why there’s never a dull moment working as a male pro dom, who’s next?
But there’s more….
What is a fetish?
And is it normal for guys to wear heels, in public or in secret?
Why do some men like wearing stockings?
I’m forever studying sexuality, not least in an effort to dig deeper into ‘what makes my clients tick?’ & to use that acquired knowledge to better deliver upon their expectations. If I can do that there’s a better chance of them becoming repeat clients right? Clients are PRECIOUS and becoming more so, why? Because there’s a ‘trickle down’ effect re ‘social norms’. What do I mean by that? For the last ten years we’ve seen increasing liberalisation of issues associated with sexuality, not least gender. Until the pendulum swung too far, in that it became weaponsied. Now we’re seeing pushback with some suggesting we might be returning to the ‘dark ages’ pre 2013 or heaven forbid 1967. As an escort couple (fun50couple where I’m the male half) we’ve done very well catering to ‘sex positive’ open minded men keen on exploring their sexuality. Their numbers have grown year on year in tandem with relaxed attitudes. We’re already seeing signs though of a reduction in numbers of ‘bi-curious’ clients. All of a sudden it seems many of ’em, who latterly would have plucked up the courage, thought to themselves ‘I’m me, WTF, life’s short let’s do it’ now seem more reluctant, fearful even, of doing so. Reason being is toxic masculinity’s taking hold again, so instead of being ‘relaxed & open minded’ the same guys are being influenced (subtly without him even being 100% conscious of it) to think more ‘Man up!, Forget that shit’.
You may be reading this thinking that’s rubbish. But one of the advantages of blogging over many years (since 2016) is that you’ve a published record of feelings & observations. At the time of Trump’s first election I aired misgivings about what the future held with regard to liberalism, which never really came to fruition. Then, we had the Biden administration which ramped up DEI, and all that helped us, through the trickle down effect. You have to remember I’m working every day at the sharp end of human sexuality…men’s’ wants/needs/desires/expectations/hopes/fears/emotional/psychological issues…these things MATTER. The ‘gender’ subject has touched me in other ways too, with a relation born as a biological female, transitioning to male since THE AGE OF SEVEN. Couple all that to experiences with genuine sufferers of gender dysphoria I have as clients, time spent with cross dressers and submissives and you’ll understand why I feel the need to keep my finger on the pulse of the niche within ‘our industry’.
So what was intended to be a light hearted footnote fleshing out why ‘men like to wear heels too!’ triggered a deep dark journey, down a rabbit hole…. a space I’d been meaning to explore further for several months, IE the “Let’s just destroy gender” argument, especially since the furore surrounding Rowling and the Supreme Court Ruling defining what is and what is not a woman, which I’m not 100% comfortable with.
I’ll likely post about that sometime in the future.
What is a fetish then? Answer: a form of sexual desire in which gratification is strongly linked to a particular object or activity or a part of the body other than the sexual organs. In Dave’s case it was first & foremost heels. But why? Again, it gets blurred. Heels affect posture and accentuate the body. There’s a cultural symbolism to high heels too.. with connotations of confidence, allure, status and power. Wearing heels pulls the shoulders back, tautens the upper legs and enhances the hips and bum…reasons why women wear them & men are attracted to them on a woman. They’re a form of self expression, and there lies the key… When men like Dave put on a pair of heels they’re doing it for all the reasons above, but also to step away from societal pressures and ‘wear what truly feels like me’, embracing the person he is without worrying about judgment.
You see, there are guys out there, millions of them living a lie IN PUBLIC. They feel neither strongly masculine or strongly feminine, somewhere IN BETWEEN male and female if you will. Some of these individuals want to ‘nurture’ that element of femininity, to treasure it, rather than bury it; They recognise it’s PART OF THEM, its what makes THEM tick. I refer to it in some of my advertising, reaching out to men with ‘the little seed in their head that steadfastly refuses to go away’ unless they address it. Attempting to dismiss it results in stress and mental torture, a HEAVY LOAD of baggage dragging on their daily lives. The Courts decreed what was a man and what was a woman, but what are male and female anyway? You’re born with a penis or a vagina (in most cases) & assigned gender male or gender female, but those genders are nothing more than social categories defined by what society expects of the people who are assigned to them forged over time by history and politics.
In the 17th century men routinely wore heels. Which men? Kings, aristocrats, the rich and powerful. The fashion of high heels for men came to Europe from Persia where heeled shoes were worn by the cavalry since the 10th century. With the heel wedged into the stirrup, a rider could rise and wield his sword more effectively.
The period between the 17th & 18th centuries was known as the period of Enlightenment, which radically shifted ideas around humanity.
The closing years of the 18th Century witnessed a profound reframing of Western masculine dress known as the “Great Male Renunciation” period. During this period there was a widening gender divide; men were defined as being active (workers, providers, fighters), while women were seen as decorative (child bearers, homemakers) “It’s these very coded and deeply embedded concepts of gender that we still feel today” suggests Elizabeth Semmelhack, senior curator of the Bata Shoe Museum in Toronto, which houses the largest collection of footwear in the world, dating back 4,500 years. History doesn’t usually repeat but it rhymes for sure. Couple of hundred years time will society be looking back at the first 50 years of the 21st Century as a period of narrowing the divide between genders? Time will tell.
By the 20th century high heels represented femininity; Semmelhack goes on to say ‘height and masculinity had not yet become entwined, but women became their sole wearers due to “a new standard of female beauty, which was small feet”. “The high heel becomes a tool within women’s fashion to lift the bulk of women’s feet up and under their skirts to make their feet look as small as possible, and the placement of the heel is very pushed forward, allowing them to leave very small footprints behind.”
Once leather-covered heels disappeared from men’s fashion, they didn’t return except briefly in the Seventies (think rock bands) and more recently in ‘alternative fashion’ though they HAVE endured in Wild West/cowboy/American culture as a kind of sub category. So there you have it guys… a brief history of ‘men wearing heels’
Stay tuned for an upcoming blog post featuring an outdoor liaison with a VERY kinky submissive, wearing heels, #ComingSoon to NEWS VIEWS & SCREWS