Adult industry ‘pundits’ routinely proclaim ‘cuckold fantasy’ as one of THE MOST SEARCHED FOR TERMS when it comes to phone sex; other’s are ‘hypnosis’ and ‘therapists’ believe it or not. Phone sex is experiencing a revival. Why? Many reasons, including a backlash against OnlyFans (yesterday’s platform), a loneliness epidemic, and increasingly, a yearning for simpler times. People also seek reassurances through chatting with PSO’s (phone sex operators) that their kinks AREN’T as weird as they thought they were. All these things I’m familiar with, as an accomplished PSO over decades. Even so, I’ve been fascinated in recent years, working at the ‘sharp end of the business’ by the sheer numbers of *men* captivated by the cuckold lifestyle. Recently I had the good fortune to experience one of the hottest meets of my career courtesy of a gentleman we’ll call (for the purposes of this post) Shaun. It was a tad unusual, and horny AF, hence the reason I’m minded to share it with you…
Shaun’s a 64 year old corporate accountant from Brighton, successful, kind of ‘well worn’ but still good looking, and tanned. I’d describe his face as ‘sunny’ not from the colour of his skin, but from its disposition… verging on smarmy, defined as ‘polite, elegant and sophisticated in manner’. Yep, I’m happy with that… it fits our man to a ‘T’. Standing around six foot three with body proportionate, Shaun came across as the kinda guy who was ‘in charge’ CONSTANTLY, slightly dismissive but ‘tolerant’ of lesser mortals, and some-one you just knew was ‘going to be a handful’, at least until such time you’d gained the upper hand. In a word, challenging. I tend to thrive on clients like him. Always have done. They push my limits while I’m pushing theirs so it can be a win-win, but only if I’ve dome my homework beforehand. That’s why rates are what they are for professionals; and the reason why people like Shaun scour the length and breadth of Britain for service providers who (they perceive) stand a good chance of DELIVERING.
Shaun was obsessed with secrecy & paranoid about security breeches & the possibility of contracting STD’s; he’d NEVER seen an escort before, but had enjoyed several instances of swinging, including MFM threeways with a previous partner. He contacted me slightly distraught because in his words he ‘couldn’t get rid of a little seed in his mind however hard he tried, and he didn’t really know where it had come from….’ So, what was that seed? You guessed it… the ‘C’ scenario, as in cuckold fantasy, but not quite in the way you might think. Let me explain.
Shaun was on his third marriage and by the sounds of it, third time lucky. A bit like myself. He’d FINALLY struck gold. Even so, there was still a ‘but’. That being a reluctance on the wife’s part to share any of their kinky thoughts or habits with others or in public. Shaun was clearly still IN LOVE with his partner of nearly twenty years, but increasingly frustrated nonetheless as he couldn’t go that ONE STEP FURTHER with her. Shaun’s used to getting exactly what he wants from people one way or another, and yet, he’d all but given up on his cuckold fantasy, thinking there’s no way Elizabeth aka Libby (not her real name) was ever going to play ball.
Shaun, during his introductory call didn’t tell me too much about her, save for saying she was ‘a stunner’, and that he had a sexual fantasy (cuckold). Was I available for a three hour meeting where we could explore his ‘cuckold fantasy’ while talking about his partner? Elaborating further, he suggested he bring pictures, videos even, signing off by saying ‘I suspect this list of wants is unusual/odd and a bit pervy but I promise a cash bonus in addition to your normal fees.’
A good part of escorting is to expect and be prepared for the unexpected, so I wasn’t in the least bit fazed by Shaun’s request. Vanilla-ish people will often blow routine scenarios out of all proportion; what we were discussing here was nothing more than mutual admiration of a sexy woman culminating in Shaun getting off through sharing those images with another, given the unlikelihood of it ever happening for real. As far as I could see it was merely one step beyond watching cuckold fantasy clips played on porn sites.
A date was agreed, and around three weeks later there he was stood in reception, obviously nervous yet composed, courteous and probably horny, though there was nothing at this stage anyway to suggest the latter. In the week previous he’d fleshed out his scenario, sending me a carefully crafted screed, outlining his cuckold fantasy in detail. Because it was spaced, with bullet points and headings, I didn’t immediately pick up on his submissive tendencies, my bad. I should have, but it didn’t matter. Those traits soon became evident once he’d settled his tribute, and we’d proceeded to the office and then the playroom for PART 1, what he’d labelled ‘PREP & INTERROGATION’.
He’d driven all the way northeast from Brighton in a oner, so he needed to freshen up, and douche ready for what was to come. Once that was out the way, he came though to the playroom. Prior to that he’d asked to be ‘shown around’ and I got the impression he thought the office rather small; he didn’t know what that room had seen in its time, small can be beautiful, and intimate. Perched on a little black Belgravia style stool, I directed him to sit on the bondage bed, & proceeded to question him as per his cuckold fantasy script. I’ve commented before about roleplay, get it right and you can make it so real the recipient gets lost in the scene.
‘What did Libby look like?’
‘What was her bra size?’
‘What does she like in bed?’
‘Sexual fantasies, what are hers?’
‘What was Shaun’s ultimate fantasy?’
He’d told me to be mildly dominant, and to include spanking should he be reluctant to answer a query.
I discovered Libby was five foot four, a size 14, with 34H breasts, long blonde hair, fifteen years his junior and she adored anal sex. Couldn’t get enough of it apparently. While questioning him I got him to remove his bath robe, revealing an average cock, big balls and moderate pubic hair. Though he’d had his fair share of sexual encounters, some of them illicit, he came across as a bit naive in discussion relating to the finer points of female stimulation. I wondered if when he was younger he’d been an ‘alpha male’, the ‘God’s gift to women type’ we sometimes suffer when working as an escort couple. Had he come full circle, and a realization in later life that HER needs were paramount, not his. What struck me most was his unshakable conviction that ‘she’ would never consider any of his fantasies, EVER. Seemingly he knew that FOR CERTAIN. She was a ‘good girl’, not even a career woman, but a housewife and a respectable one at that. They’d first met at a ramblers club apparently, and got talking. Two weeks later he was bedding her; a little while after that and he’d moved in with her at Brighton. A big house close to London’s South Bank he retained for investment purposes, for business trips and occasional ‘jollies’ surrounding ‘society’ and the high life.
I was curious. In most things, especially sex and politics you never say NEVER. Because you don’t know what’s around the corner. Sexy people can be caught off guard, seduced sometimes in ways they could never have previously imagined…but he was adamant… she would not be a party to any of the things he craved. I asked if he’d got pictures of her on his phone or laptop. He’d come in with a carry case slung across his shoulder and I’d assumed there to be a computer in there somewhere. Had he ever videoed her? I made him tell me what they showed, then goaded him to show me them. Hesitant at first, he finally relented… after I’d tapped his shriveled cock with a riding crop then encouraged him a bit more with a thwack across his balls
‘Alright alright I’ll show you!’ he stammered.
‘Good. I was hoping you would…..now, in there’ ushering him towards the office.
There’s an eight foot long desk, a big 32 inch TV converted into a monitor sat in the window over and above another 26 inch screen connected to a keyboard, and two tower computers driving the things. One way or another we’d get to see Libby in all her naked glory on screen. He’d put the content onto a memory stick, so in no time at all I was opening the files; there were HUNDREDS of images listed, more than I could count. I clicked OPEN and voila there she was, a decent looking blonde in a zebra print dress, black stockings and three inch heels, pouting for the cameraman. She looked promising.
Opening the file was akin to flicking a switch as far as Shaun’s cock was concerned. Springing to attention it quickly hardened to around six inches; very thick and veiny too. Shaun started sighing. In hindsight I admit I can relate to that…. sexy pictures of your partner or even yourself can be a turn on. They remind you of HIGH’s past & prompt you to picture times in the future, the very reason he was with me in the first place.
In the cuckold fantasy missive he’d suggested we ‘touch ourselves whilst I talked dirty about her body, what I’d like to do to her, and what he’d like to see me doing’
The images were in order; she’d agreed to a photo shoot for his Christmas treat, provided he always kept them private. Initially refusing him she’d changed her mind, surprising him on Christmas Eve. Fortunately there was no tinsel, Santa outfit or cheap red lingerie… she was way more classy, choosing a black basque trimmed in lace, seamed black stockings and patent style heels. The only baubles were the two adorning her chest, and quite remarkable they were too in that they appeared firm, rounded, like she worked out; I never asked if they were real, they looked it, and top notch too for a forty nine year old. Her nipples could be seen too, pressed up against the black bustier. What caught my eye though was pic number 14, which showed her still in knickers, but the tell tale ‘camel toe’ clearly discernable… a case of ‘less is more’. The Minx always tells me clothed is sexier than naked, and I agree (about 40% of the time anyway heehee) In my view you just can’t beat a nicely proportioned naked ass big or small… that would come later. Pic 14 worked its magic in that I felt stirrings, encouraging me to undo my fly. I was wearing black jeans, boots, and a fun-five-0 t-shirt which depicts a sexy couple with a tagline referring to ‘sextoys for sex positive men and male-female couples’. The fun-five-o website is suspended for now, until we manage to activate a payment gateway which has fiat currency/crypto interoperability. [not an easy task]
Under the jeans I wore a black wetlook thong from MALEPOWER. Shaun kept handling his cock, and talking about what I would do with Libby. I told him I’d tie him to a chair similar to the one he sat in and force him to watch, as I took his sexy partner every which way she wanted, no holes barred. Talking of which, slide #20 revealed all… her part bottom bent over revealing both her holes open, legs taut, head visible between her legs, gloss pink lippie reflecting a pin point of light from somewhere behind the camera…. gloriously explicit. It got me hard, noticeably so..
‘Can I touch it’ ventured Shaun
‘Course…I’m so fucking horny now’
Reaching over I held his swollen dick, stretching across, he rubbed mine through the wetlook material…
‘Do you wanna see it out Shaun?’
‘Yes, I do’ he replied
He’s a straight guy remember, and the threeways he’d experienced in the past were MFM’s not MMF’s, this was his first time ever interacting sexually with another man…
‘Oh God’
I’d risen from the swivel chair and was now wanking slowly, describing graphically to Shaun how I would fuck the love of his life, in front of him. Prior to that I’d briefly sucked him, taking him to the absolute edge and very nearly beyond what he could control. I could sense his mind was close to being overwhelmed. At times he turned his head like it was shrinking away from the unfolding scene, before snapping back for more. I’d got hold of his dick again… while stretching the skin way back on mine showing off my swollen glans all shiny with a tinge of purple; it was a horny scene, the likes of which you don’t get to experience very often not even as an escort; it seemed unlikely but there you go…. pic #20 was good but 21 was even better. Turning the knurled knob on the wireless mouse I zoomed in to view Libby’s cunt and asshole in fine detail… the photo was sharp, and professional, it was like she was there for real. Shaun let go big time. Waves of heavy semen flowed from his bell end, over our fingers and down to his balls. ‘AGHHHHHHHHHH!’ he cried, clearly shocked. Stupefied even. For a moment he appeared utterly bewildered… Eager to keep the fire burning, I repeated what he’d told me earlier about his ‘party piece’; a capacity to easily cum twice in a short session. That was probably him harking back to his swinging days.
His email had included explicit instructions, for example [verbatim] ‘Make me suck you’ and ‘I don’t know if you kiss clients (or will feel like doing that to me) but if you do, tell me you’re feeling so horny you need to fuck and you want to show me what you want to do with my wife. If you do, start by showing me how you’d kiss her’
‘Slide your hand up my leg and show me how you’d finger her’
After I’d read his message I wasted no time confirming I could deliver EVERYTHING on the menu. I don’t know whether he’d had his time wasted before by others, because his reply implied he’d tip me generously if I could perform. There’s a hashtag out there pertaining to sex workers; it says #sexworkisrealwork and I often refer to it. It’s not the sex that’s hard, its the timewasters and the dreamers; they drain you. A good many of the jobs drain you too, but in a good way ha! And this was one of ’em. He’d regained his composure. As he relaxed in the basketweave chair once more, I straddled him. Cupping his head in my hands I challenged him ‘you wanna see how I’d kiss Libby? Well do you? Purse your tongue and let me suck it like a cock…’
Doing as he was told he opened his mouth, leaned towards me and took my kiss. Sucking on his tongue hard then planting my lips firmly against his I snogged him forcefully. Passionately. You could feel the heat, the lust, it was all he hoped for and more, I was sure of that. We’d got well passed the ‘gentle exploration’ stage. I was on fire and best of all he was keeping up. Two full hours had passed and we’d got no further than the fortieth image; there were videos to go through…. what about the fingering I hear you ask? That too…. ordering him to open his legs, he complied, willingly, spreading them wide supported by the pine desk. As he raised his ass from the chair, my hand wandered…. higher and higher, eventually finding his mancunt, the focus of his desire….. ‘how does Libby feel when you fuck her ass?’ he demanded to know.
‘You’re gonna find out!’
Surely it would be even better for him with the prostate ‘up there’; that sacred spot populated by hundreds of nerve endings. Stimulated correctly it could induce earth shattering orgasms…. I found it, but only just; he’d not positioned himself the best… not his fault, and not a cause for worry since we still had the remainder of Cuckold Fantasy Part 3 and all of Part 4 to play out yet.
The final act had bullet points:
‘Get me to start the second video then go on all fours so we can both watch the clip’
‘Take me from behind while talking dirty about my wife and what you want to do to her’
‘Go through all the positions you’d like to fuck her in’
‘If you cum while fucking, take the condom off………..’ and more. Much more, which I’m not going to divulge. The fingering combined with close examination of Image Number 42 as I spouted yet more dirty filth got him off again. This time there was seed all over the place, over his belly, his legs, even some on the table, he was so CHARGED…
‘I’m done’
‘REALLY????????’ I murmured, slightly disappointed.
I still hadn’t cum; nearly, but I’d chosen to save it. I was programmed to fuck, anticipating another full hour of play. But it was not to be.
I’m left wondering if he’ll return. I hope he will. After all, there’s still Act 2, scenes 3 & 4 of his Cuckold Fantasy to play out. He conceded to sensory overload and I did my best to re-assure him, thinking back to the many times I’ve witnessed men freak out when they ‘realise what they’ve just done’ immediately AFTER they’ve cum. Some you don’t see again as they NEVER repeat the experience; it’s a bucket list thing. Others are in denial, then call for a second appointment weeks, months or even years later. For a tiny percentage it’s the beginning of an exciting new journey, a realization that life’s indeed short & not much harm can come of it. It’s about looking after Number One (you), your wants, your needs & desires, and not like you’re having an affair.
So dear reader, with that said, do you have a cuckold fantasy? Are you drawn to the cuckold lifestyle for real OR as a mental image based on conscious or unconscious desire? I’d love to know what you think. Email me at sessions@northernmaster.co.uk.
Best
Geeze
PS: A true account as are ALL fun50geeze, Northern Master, and NEWS VIEWS & SCREWS posts. Only names & appearances have been changed to preserve anonymity. Who’s next?
Origin of the word ‘cuckold’ courtesy of etymonline.com :