Let’s re-visit cross dressing shall we? Once in a while a meeting comes along which I feel compelled to share with y’all for two reasons, number one it was so friking horny, and number two to give encouragement to others who fantasize about these things yet continue to sit on the fence. Before we dive in, a word or two about the latter. I’ve written blogposts before about whether fantasies should remain just that, fantasies… however, if you find yourself erring towards taking action & making it happen I suggest you do it soon. Unless you’ve been living under a rock or you get all your news from main stream media, you won’t have failed to notice increasingly dark times, with individuals being crushed by the State. Starmer’s pledged to make digital ID mandatory. I hope you’re not one of those who pipes up ‘if you’re not a criminal then you’ve nothing to hide’. Why? Because even an eight year old can see where this is leading…Digital ID linked to tokenised money means you’re in a cage… no longer able to do WHAT YOU WANT, instead, only what’s deemed good and proper by the state aka Communism. I hadn’t realised until a couple of days ago that the UK is uniquely different to Europe in that we are able to do anything we like provided it’s not illegal, whereas across the channel its turned upon its head, meaning you are only allowed to do what the state expressly says you can do. For an eloquent explanation SEE THIS VIDEO. It remains to be seen whether UKLabour will be able to deliver digital ID given the poor track record of government implementation of IT projects, nevertheless the writing’s on the wall, which is the reason I implore you to not only #SayNoToDigitalID and spread the word, but also to act upon urges and DO THINGS NOW while you still can. Online Safety Act is another bone of contention…I’m being told by other escorts and massage therapists that bookings are down dramatically in recent weeks reason being a lot of guys refuse to age verify on platforms like AdultWork; #costoflivingcrisis with bills for essentials rising anywhere between 5 & 30% annually means there’s less discretionary spending too. We’re keeping going though, thankful we (Minx & Geeze) had the foresight to build independent websites to counter these kinds of setbacks.
Some clients follow us for YEARS before plucking up courage to pick up the phone. That’s a shame, because at the end of the day we’re just normal folk, like them, highly sexed and inclined to live life a little bit risqué, to see what’s out there instead of merely following the fold. Steph is one such guy, at age 30 way ahead of many of his peers, most of whom will not start to entertain thoughts of ‘alternative activities’ until they’re well into their fifties when sex has dried up (literally) at home. Steph’s a good communicator too, and that more than any other reason led to him booking an appointment. Why? Because he’d talked through his wants/needs/desires with his other half; not holding back, and get this: it was SHE who encouraged him to pick up the phone. A strong relationship for sure, and one I’m familiar with myself since the Minx empathises with me; we trust each other implicitly…and I have to say it took me 24 years of living a lie, and two broken marriages before I knew what to look for… and happiness. So hats off to Steph and his good lady… who I’m told has a few submissive desires herself. Men often tell me how lucky I am to be out as bisexual given 83% of bi men remain in the closet, mainly due to peer pressure. Remember me telling you bookings are down? Another reason for that is trickle down effect from the likes of Trump, Meloni & Milei. We’re supporters of all three and if that turns you off so be it…move on. Some might question how as escorts playing with subs sissies and people exploring their sexuality we can be onside with hard line Republicans/Christians/Holier Than Thou’s? To answer that question I’d turn to a tweet posted by A True Liberal on ‘X’ @MInthenow70635
‘I’m a gay man. I’m not LGBTQIA2S+.
There’s a big difference.
I’m a man that happens to be same sex attracted and the other is an extremist cult.
Please don’t associate us all with that cult.’
People like me (bi), and him (gay) have ALWAYS been out there. In Roman times man-on-man was a big thing… a badge of honour. Public acceptance/denial of such matters has ebbed and flowed like the tide, over thousands of years. Right now it’s ebbing fast but that doesn’t mean we won’t continue BEHIND CLOSED DOORS. The retreat means some men will rein back their desires and fantasies; the ‘approved narrative’ will have its desired effect and rub off on some of ’em…. ‘Be a man…’ ‘men don’t wear panties’,’men can’t ever feel feminine, it’s a mental illness’, ‘there are only two genders’ blah blah and we’re back to penis and vagina defining precisely where you fit in life. Another fascinating article I read recently explored the mismatch between right of centre people like me and subs who play with them (submissives tend to be left leaning); it reminded me of some gay men’s fascination with HIV… treating it as the ultimate master, weird I know, but understandable when you’ve been an observer & participant in their space for decades. But I digress. During the meeting’s ‘preamble’ Steph alluded to agreeing with me about the ‘trickle down’ effect, nevertheless he knew what he wanted deep down, it had been an itch aching to be scratched over many years and he was committed so here he was one weekday night recently, at my home in County Durham not knowing really what to expect… ‘not sure how far I’ll go’ was what he told me. To be fair that’s what I expected from someone who’d never been with an escort, never had an affair, and never played with another man EVER.
We’d had a brief phone chat a couple of weeks before so I had some idea of where he was coming from, and body shape, nonetheless when I first saw him I was pleasantly surprised… in this job you kiss some frogs, its part of the territory (in reality nearly anyone has SOMETHING to offer, you just gotta find it… sex isn’t just about looks though looks can help for sure). Steph was slightly built, around 5 foot ten tall, with a ‘fresh face’… they told me that at school in a sneering way, implying I was boyish & immature. Many of my fellow pupils were ‘OH! so mature… and capable’… wonder what they’re like now! I heard one (the form bully who was shaving at 12 suffered chronic illness before he was thirty) The great thing about being boyish in complexion is it’s a pointer to later life… most punters place me at an age fifteen years or more younger than what I am for real… regular heavy sex and exercise helps too!
During the preamble I discovered we had several things in common, interest wise as well as sexually. I could empathise with him easily. As a switch I’m totally familiar with the feelings cross dressing can generate. Some men have a pantyhose fetish or they like stockings… they like the sheer feeling, at the bottom end of the ‘dressing’ scale I’d say but not to be scoffed at! They’re they and I’m me… different strokes for different folks. Some stay as men who like to wear panties, others are on a journey… finding themselves doing things they’d never have contemplated a few years ago, such is life. I’d include myself in that group. Unusally, Steph, my client, had never before tried any of it… cross dressing was nothing more than a ‘kinky thought’. Most guys we see have messed around when alone, and one thing leads to another, but none of that was true of Steph. This was a FIRST. I felt honoured, and pleased, because I knew I could deliver one hundred per cent. People who know me know I’m an all or nothing guy, and inclined to do everything at 100 miles per hour… Minx will confirm that but invariably qualifies it by adding ‘he’s got all the time & patience in the World when it comes to sex’…ha! For me, sexwork is a vocation, a calling. OOOPS! Calling to me means something higher than work. The word comes from the Greek kaleo and vocation comes from the Latin vox, meaning voice. Each was intended by Protestant Reformers to point to an entire life lived in response to the voice, or call, of God. ‘Work’ & ‘vocation’ commonly these days (it wasn’t always like this) refer to one and the same thing. The problem with ‘calling’ for me is its religious connotations as I’m a non believer. I referred before to a RENEWAL of Christian values on the back of Trump, Meloni, Milei…’work’ as defined by Christian faith should be ‘the full expression of the worker’s faculties, the thing in which he finds spiritual, mental and bodily satisfaction, and the medium in which he offers himself to..’ and I’ll leave off the G word and replace it with ‘my client’. That truly defines where I am with sexwork.
So I was very comfortable quizzing Steph on his true feelings, and sharing with him resources like the Bemsex test & Klein Sexuality grid, so he’d know he was perfectly normal, and on the same page as MILLIONS of others which reminds me, this week was Bi Visibility Week! (I wonder if that had sparked the conversation with his wife which led to him taking action?!)
I’d offered him iced water on his arrival…to calm nerves and a dry mouth, but he soon appeared to be more at ease. We got the tribute out the way and then I led him to the changing area, telling him to strip off and we’d get him dressed. The nerves came back… clearly he was apprehensive now at the prospect of revealing all, choosing to keep his boxers on with his hands held together in front of them, shielding the ‘crown jewels’ or any semblance of them from view.
‘Don’t be shy!’ I told him, but let him keep them on while we rummaged for hold ups and stockings… I’ve a huge collection of hosiery/lingerie/footwear/wigs/makeup…trying hosiery for size took his mind off the impending nudity…. so once we got the holdups on, I encouraged him once more to drop his boxers. He’d told me he wanted a dominant male; to a degree he knew he had to be forced to do what he’d secretly only fantasized about up until this moment. I knew it was a stepping stone, and by taking it slowly & sensually, with lots of reassurance on the way, there’d be a strong chance he’d go well beyond what he expected. I gave him a lacey thong to put on to partially conceal his *man*hood which TBF looked impressive. I told him that in time I’d teach him to masturbate like a woman… next up was a suspender belt. He preferred black, but the first one we tried, a six strap item proved difficult to fasten so we opted for a skimpier piece with bigger brass fasteners…. they worked a treat. While fitting him I brushed against his cock, steadily growing but kept in check by the tight lace thong… was it my imagination or was he wet? And sticky? He looked like he was pre-cumming….‘Sorry’ he murmured….
‘Don’t apologise’ I replied, secretly pleased that he was getting aroused.
‘Okay, skirt yeah? Little black denim or tartan?’. I’ve got dresses and skirts in all shapes sizes and materials but I already knew what would suit him best for this first occasion…. a promiscuous sixth former or uni student in a skirt barely concealing her bottom kinda look, with sexy heels and a wig we’d experiment with once we’d got *her* dressed. I’ve a couple of tartan skirts, one’s a halter neck… the material’s very soft & I chose that one. She had a hairy chest, so it wasn’t ideal, but the fit was good… if there’s a next time and I hope there will be, I’ll kit her out with a lace top and a bomber jacket. Anyway, the tartan looked good, fitting perfectly. As I tied it around her neck I turned to the shoe box. Red suede heels were too big, she was an 8; I rummaged again, and found a black pair of stilettos with gold accents, quite close fitting but they turned out to be a good choice. Unlike many newbies she managed to walk in them with ease; I do believe she was totally new to all of this still, and not had practice beforehand… nevertheless, I briefed her on safe management of the stairs while wearing them. I knew that a domestic setting to begin with would be preferable to the full blown BDSM playroom…it would put her at ease, and she could walk around & look at herself in the big wall mirror… there are comfy leather sofas too. I thought we could talk more and ‘get to know each other’ better down there. We still had a wig to sort though. I tried a black bob on her…it looked good, the ‘boyish’ face was now looking more feminine under the guise of the wig, but I thought she’d benefit from a bit more in the way of length (mmmmmmm ha!) All the wigs are pristine; I showed her how to put them on. She kinda liked the longer one too; it’s a parted shoulder length brunette piece…. I spent some time straightening it, setting it, and brushing it out. Clearly she was enjoying it, and beginning to relax. Cocky had grown more, prompting me to tell her to conceal it with the thong, and yes…you guessed it, the precum was now more evident, warm and slimy, begging to be rubbed in & massaged…. Steering her toward the big floor mirror I encouraged her to think woman, think flirty, show off those legs…I asked her if she was feeling it in her tits? She confessed she didn’t really know if her nipples were sensitive or not. WOW! You don’t know? Nipple sensitivity is like a ‘litmus test’ for bisexuality/gay sexuality… she was fit with a good body…including breasts…not ugly man tits, more ‘barely forming but nevertheless noticeable breasts’. I enlightened her about nipple creams and tablets you can buy which increase sensitivity and/or enhance shape and size. I rubbed her nipples and teased them, drawing her close to me. She was smiling now, and I got behind her, reached around to her thong and showed her how to frig herself off using the flats of two fingers… yes… it’s possible to orgasm like that when you’re not even hard. As I’ve told you many times before in previous blogs, the brains the biggest sex organ. It will bring you to orgasm if its temporarily programmed as a woman especially if its focused with strong conviction; climax will happen and you will get MASSIVE relief the likes of which you might not have experienced before trust me. Another way you can do it is with a vibrator and no hand contact…WILD and FEROCIOUS is how I would describe it
‘Would you like to go downstairs?’
‘Yes’ she replied. I asked her if she’d like a drink… I’ve alcohol free beer which tastes almost like regular lager (she was driving). To my delight she accepted… it was like she was now on a date with a man, for the first time. It was what she’d dreamed about for so long. This wasn’t silly games, this was real…. no longer was she Stephen, she was Stephi, the horny promiscuous little tart always on the lookout for sex, & heavy sex at that. You see a lotta folk seeking roleplay… all kinds of scenarios. Get roleplay right and it can become frightening real, so much so that some scenes develop to such an extent its difficult for the players to revert back to reality…advanced kink if you like. (common with puppy play, pony play but can apply to cross dressing too). I’ve been involved before with some pretty hard cases playing out kidnap scenarios, and do you know what? Some crumbled under the illusion. Fascinating stuff.
I got the drinks, then took my place next to her & up close on the sofa. There’s a rich zebra print throw over the back, I lit candles too, the flames combining into a multi colour prism as they reflected back into the room off a redundant television screen mounted on the wall behind. As for me, I was wearing leather trousers and my leather chain waistcoat, skimpy sheer black thong under, and heavy boots…as you might expect from a male pro dominant. She could see my torso; groomed, muscular(ish), no belly, erect nipples. I asked her if she was wondering what was down below. She nodded. I placed her hand on my belt… it is black leather with a rose gold buckle sourced in Jupiter Florida believe it or not… I undid it; she slowly unzipped me. She was in no hurry… I think she was savoring the moment and not quite believing she was ACTUALLY doing it. I sensed this, & told her I can still clearly remember the excitement I felt doing the same thing as a youngster AT SCHOOL I kid you not, so indelibly etched into my mind are those early sexperiences. I suppose that’s one reason I felt compelled to write this post…. everything about the meet screamed EMPATHY and HOT, not least because Steph was well endowed.. I asked if she’d like photos. She said yes, so I took several… telling her to conceal her cock and to act womanly, crossing her legs, looking suggestive…that kind of thing. Some of them turned out good, the best being a shot I took about 20 minutes after, by which time she was well INTO ME. She marveled at how hard I was, and unsurprising too… here I was entwined with for all intents and purposes a hot sexy shemale with a decent body, impressive tackle and a brain, what was there not TO LOVE? We kissed too, like naturally. There was no play acting, porn star DFK over the top stuff…just mutual attraction stepping up incrementally as time passed, prompting ever more intimate contact. I suggested we go upstairs to the bed. As I said, we were entwined, but I was only able to handle her while she fellated me. I desperately wanted to suck her, to deep throat her and to feel her skin against mine. She’d been so incredibly gentle and sensual on the sofa I was turned on to the max and then some. In the playroom I turned the floor lights to red.. enough light to see by, and a warm look too. Within moments we were 69ing, swapping places, frotting together, kissing, I had her legs open wide and pushed back, it got VERY intense. At one point I felt her whole body go goosebumps… ‘you’re turned on aren’t you?’
‘Yes’ she breathed. Going head to toe again I told her to put her leg over my body as I sucked her, then moving to her balls I sucked & licked them too….I got the vibe that that wasn’t the top of her list (attention to the balls) but it didn’t matter. I was so turned on I wanted to really get into her and to taste her, while she gorged on my cock, intermittently wanking it.
‘Its alright’ I assured her ‘Be rough go on I like it rough’ in contrast to her supreme sensitivity. Unsurprising too since it was her first time, but my zillionth, over decades! But this meeting felt so erotic. It had me lit. Tonging her taint, I went for her pussy but couldn’t reach it. Wrenching her pert bottom down while simultaneously prising her lily white cheeks apart, her hole got revealed. Now I could reach it. I wanted her, I needed to taste her, I wanted to taste her as deep as I could go… in no way was I inhibited…. probing, licking, I knew it was doing it for her too because she let out a gasp, followed by several more. I fingered her, then we swapped back to facing one another…
You liked me tonging you didn’t you’
‘Yes’ she replied, we were close, my hard penis rubbing against hers, then down to her balls, before diving underneath teasing her; in truth I wanted to fuck her. I told her, but added ‘next time perhaps…..’. The last thing I wanted for her was ‘too far too quick’.
‘I’m nearly cumming’ I cried for the umpteenth time….
‘Go on I want it’ she countered, sucking on me furiously, handling me too…
‘No hands!’ then rising to a kneeling position I let her fellate me while I grasped the steel mesh of the bondage bed. For all the meet’s eroticism I wasn’t quite there. Yet. That’s the problem when you’re an escort…the bar gets raised higher and higher. Fifteen years ago I’d have cum half an hour ago and then again. I needed more FIRE. So I went back beneath her, knowing her butt would do the trick…it was so sexy and alluring; to me anyway. The sight of her tight perfectly formed hole, her pert butt, big balls and hard 8 inch cock pulled down and in my face, all that stimuli combined, taking me over the edge. Wanking me now by hand I gave her no warning. I knew I didn’t need to. Letting go I exploded here there and everywhere, most of it hitting her chest. She wasted no time in rubbing it with her fingers and putting them to her mouth. We kissed more. Then it was warm down time.
‘Was that good Stephi?’
‘YEAAAAAAH’
‘For me too….’
And that my friends is a true account of a recent meeting with a newbie cross dresser. It’s a tough job but someone gotta do it lol! Who’s next?
NOTE: SORRY NO IMAGES OF STEPH to preserve anonymity