The Invisible Man

Right now I’m averaging one new and one existing date each month. The Husband’s work stresses have started to subside and he’s really enjoying my adventures. Me going out on a date and the prospect of getting pounded by a complete stranger has started to become an ordinary part of our relationship. For him, the normalisation has become a comforting and incredibly arousing thing. But for me, the often mundane and disappointing encounters can be challenging and I’ve started to become slightly detached, both from him and my dates. Our lives are really busy and while our sex life together is good, it primarily revolves around me regaling him with tales of my adventures, without us getting much time to properly re-connect ourselves.

There are so many issues at play, primarily around our own individual sexual hang-ups and insecurities. For me it’s the ongoing challenge of reprogramming decades of social conditioning. Where I want to indulge in my love of sex and intimacy as the strong, beautiful, sexually empowered woman that I am, years of being told that I’m a cheap, ugly, desperate slag are hard to break free from.

While my rational brain is all too aware of what’s going on, it doesn’t stop the emotional virtual blow to the stomach that I experience from rejection or regret, one which still has the power to turn me into a needy insecure wreck on a regular basis.

There has been an emotional connection missing in my most recent interactions. While each has provided a unique contribution to my voyage of sexual rediscovery, it’s all been about the physical act, rather than any particular mutual adoration and respect. For The Husband, this is the realisation of his slutty hotwife fantasies. For me, it’s not entirely satisfying and I feel like I’ve lost direction while I’ve been exploring my boundaries and preferences. My new friend marks a bit of a turning point.

He is so non-descript that I’m finding him difficult to describe. He’s recently divorced and lives a couple of hours away but stays in a city hotel for work during the week. The messaging isn’t particularly exciting but he’s persistent, enthusiastic and convenient. And largely due to procrastination from a work deadline, I agree to meet him for a quick coffee nearby.

I don’t feel any instant attraction or connection, but he’s not bad looking and seems pleasant, polite and easy company. It’s an incredibly quick coffee and I’m not madly moved, but messaging me afterwards he starts to win me over with enthusiastic compliments and invitations to dinner. Besides, having a clean, impersonal, convenient place to spontaneously fuck during the working week is an attractive prospect.

Me and The Husband had exciting plans with Easy Rider that night. It was all set up for him to drive me over to get reacquainted with my friend after a few month’s break. After Easy Rider was done with me, The Husband would be invited in to clean me up before we say our goodbyes and head off home. Fun times.

But Easy Rider cancelled around lunchtime. He was heading off on holiday the next day and couldn’t make the timing work. I’m pretty convinced that nerves may have played a role in the decision too, understandably.

So after a hot few days of build-up, we’re left hanging. And out of the blue, The Invisible Man appears with an empty diary, a convenient location, a pleasant personality, and a raging hard on. The Husband agrees, and I take up the offer of a drink after work.

He’s sat outside of the pub watching me walk across the square towards him with a big smile on his face. While he’s a man of few words, he’s warm and affectionate and gazes adoringly at me whilst plying me with wine. I like it a lot.

Soon enough, we’re quite drunk, ravenously hungry and increasingly horny. And as luck would have it, his hotel is just around the corner. Neither of us was convinced it would happen and I’m being almost coy as he gradually seduces me. When he spots his work colleagues in the hotel bar, we have no choice but to retire to his room before our date night is derailed. After a very encouraging snog and a grope, he orders pizza and disappears to get a bottle of wine. There’s no place for coyness now, and I shower and get into the bed naked before he comes back.

The spontaneity, excitement and affection is intoxicating. While his cock isn’t ginormous, we’re a good match physically and the sex is great fun. He has a previously unfulfilled passion for bum sex (again) and when I filthily tell him to cum in my tight little arse, he has the most ridiculously hard and long orgasm, proclaiming ‘where have you been all my life?!?’

And the aftermath of cuddling, pizza and TV is lovely too. So much so that even when I know The Husband is waiting outside to take me home, I jump straight back on and ride him till I orgasm.

Roman Holiday

It’s been a while. I’ve been taking a break – one which I’ll get around to writing about eventually, when I’ve recovered enough.

But in the meantime, I was keen to keep my posts chronological, if not in real time. And it’s taken me a while to get around to recounting the surreal and relatively spontaneous afternoon I spent with a stranger in a city hotel.

Disillusioned once more, I had given another sex dating site a go. I posted my most direct, straightforward and brazen profile to date and was enjoying a reassuring rush of excitement from the new and varied contacts.

He’s a cheeky, confident, experienced, and enthusiastic Italian who wastes no time in meeting. We both snatch a quick half hour from work and sit opposite each other in the coffee shop. I’m feeling decidedly flushed and uncharacteristically shy as he stares intensely into my eyes. It’s a quick introductory meeting and after we walk outside, I’m taken aback when he kisses me passionately in the middle of the busy street, in broad daylight, just around the corner from my work.

Despite the mild embarrassment, I skip back to work jauntily with a cheeky grin across my face. The short, smooth, swarthy, passionate, middle-aged Italian thing is the stuff of my adolescent fantasies, fuelled by a complete and enduring devotion to Al Pacino.

I tell my new friend that he can make the fantasies of my teenage years comes true. He enthusiastically obliges, setting plans in motion to meet the following day. Of course there always has to be a hitch involved when you’re trying to make fantasies come true, and the hitch this time is that he’s a 50-something year old man who lives with his parents. He dresses it up as being their carer. But let’s be honest, it’s still living at home with parents.

The other hitch is that he turns out to be a bit of a twat, a fact that only begins to emerge slowly at first. The first alarm bell sounds as we’re making plans through the message app in the morning. Instead of charming his way into my pants and reassuring a lone woman who’s about to turn up to a stranger’s hotel room, I detect a hint of irritation when he asks me to phone him to clarify. He’s rushing around doing chores and faffing over details in a decidedly unsexy manner. He even tells me later that he had gone to book the hotel in person rather than online, insisting on inspecting the room first.

I’d initially agreed to meet for a glass of wine and take it from there. But somehow the plans had quickly escalated to getting straight down to it. It’s a really hot day as I make my way sweatily from the train station and I’m increasingly nervous about walking brazenly through a hotel lobby like a woman up to no good. Bizarrely, it’s the logistics of finding the room without looking embarrassingly seedy that’s worrying me more than the naked shennanegins once I get inside.

I call to let him know when I’m nearby, and of course he’s faffing and running late. I head to the pub around the corner to grab a quick glass of prosecco to steady my nerves. Almost immediately, he calls to let me know the room number and I prepare to do the walk of shame past the reception. Unsurprisingly, no one bats an eyelid and I find the room easily, letting myself in as instructed. The blinds are drawn, the room is dark, and he’s sitting in an armchair. I think he’s going for some kind of enigmatic and dramatic mood. There’s absolutely no hint of irony and I stifle a giggle at his pretentiousness.

But the room is nice, the wine is chilled, and the whole daytime hotel vibe has a delightful seediness about it that excites me. We’re standing in the middle of the room and the snogging is fabulous and I’m getting into this already. Despite the hint of twattishness, he’s definitely got all of the attributes of my adolescent dreams – the accent, the confident demeanour, the hairy chest, and a reassuringly hard impressive dick.

Before I know it, I’m on my knees in my underwear with my mouth full and eyes watering.

The reasons behind his fussiness over the room specifics and layout soon become apparent when in another deft move, he positions me facing a floor length mirror, swiftly bending me over so that he can watch my face as he teases my pussy and slides into me.

I’m holding onto a chair on one side and a desk on the other, legs spread and wobbling, as he pounds me hard from behind, holding my hair back and watching my blissed out facial expressions as he tells me how well he’s going fuck me, intent on sending me home to tell The Husband how a real man fucks. This is working out tremendously well so far.

A year ago I would have felt ridiculously self-conscious fucking in front of a mirror. But right now I’m grinning wildly and looking delightfully disheveled – it is extremely hot.

And then it happens – a missed opportunity that I can’t help wishing I had grabbed with both sweaty, eager hands…. During my younger wild years, I had a random night of filthy passion with two men that I met in a pub. It was ultimate slut behaviour which I was pretty ashamed of for years. But equally, it was one of my hottest ever experiences and remains one of my most enduring fantasies, firmly embedded in my trusty wank-bank. And it’s an experience that I’m determined to re-visit on my current enlightened middle-aged voyage of sexual rediscovery.

Right in the midst of his porn-star sex talk, he drops the bombshell that his friend is on standby, waiting for the call to join in. It’s the kind of scenario I think up in the comfort of my own bed – he’s fucking me from behind, telling me what a delicious slut I am, and asking if I can handle more cock. But this is for real.

While I’m getting better at spontaneity, this was never even hinted at in our preliminary discussions. And having a surprise thrown at me when I’m in an already potentially vulnerable position does make me kind of nervous. I hesitate and tell him that I’m not sure… then spend the rest of the afternoon regretting my decision, half hoping that there would be a knock on the door anyway.

Nevertheless, there’s an enjoyable romp that ends somehow in a crumpled sweaty heap on the bed. I’m lounging, relaxed and hoping for some chilled and affectionate post-coital flirtatious banter to lead us into round two. He jumps up to fill my wine glass and proffers a Tupperware bowl of random sweets that he’s brought from home – he really has thought of everything.

But instead of playful bants, I get angry rants. He launches into one long interminably dull tirade about an ongoing problem with his neighbour’s fence. For ages. At one point, I even try responding with some encouraging and supportive comment to try and bring him back to the point at hand. But he’s in full flow and interjects crossly: ‘can I speak?!?’

So the decision is final – he is officially rude and arrogant, and pretty boring too. And I’m completely turned off the idea of having his penis inside me again.

Thankfully, The Husband is waiting eagerly outside to take me home to my own bed, a sanctuary from rudeness, arrogance, and indifference. Instead there’s maximum affection, appreciation and excitement as I recount my exploits. When I get to the missed threesome opportunity though, he’s gobsmacked – ‘what were you thinking?!?’ I couldn’t have put it better myself.

A few months later, and with some exciting new opportunities on the horizon, I’m now actually relieved that I went with my gut feeling about the wrongness of his approach. Now I’m absolutely confident that it’s me who’s going to call the shots for setting up my ultimate group fantasy scenarios, and I’m looking forward to it very much indeed.

Rope

The date is set. It feels like the ideal way to celebrate the end of a stressful work contract. I’m so tired and preoccupied that I don’t have time to get too excited. But on the plus side, the crippling nerves don’t have chance to take too much of a hold either.

As the day arrives, I begin with the expected ‘Good morning, Sir’ message, and he responds with detailed instructions. I am to dress however I feel sexy and comfortable. But he specifies the need to shower and avoid overpowering perfume, leading me to wonder what manner of minger must have turned up at his door in the past.

At the agreed time, I am to let myself in through the front door where there will be a cushion and a blindfold set out in the hallway. The instructions involve removing my shoes, putting on the blindfold, and kneeling with hands folded and head bowed, patiently waiting for him to appear.

I do as I am told, swiftly and uncharacteristically unthinkingly. Despite a minor flutter of panic in case he was about to drop some previously undiscussed surprise on me, I realise that the usual gut-wrenching nerves are replaced with anticipation and excitement. He tells me later that while he was watching me waiting, I had an enormous grin on my face.

As the anticipation builds, I hear his footsteps as he comes to stand behind me and pull me up, wrapping his arms around me roughly. I am swiftly steered towards what I think is the main room, and once again I’m shoved to the floor while he sits on the end of a bed. I know that this kind of thing requires a degree of role playing seriousness but I really am struggling not to chuckle. I’m not taking the piss, I’m just nervously excited.

He restates the purpose of my visit, confirming my consent for what is about to happen, and testing me on the safe words. The smile is quickly wiped off my face when pushes my head down, instructing me to kiss his feet. I really wasn’t expecting that, and I’m not overly enthusiastic at all. Being used as a sex object is one thing, but worshipping the manky feet of a virtual stranger is a different matter altogether. But like any good sub would, I go with it.

Thankfully, it is only a brief moment. And the fun begins when he stands up, waving his rock hard dick at my face, making me seek it out with my eager mouth. He definitely has the attractive mix of encouraging words and authority that I find incredibly effective.

Eventually, I am pulled up and instructed to undress. Soon I am standing in the middle of a stranger’s dungeon, blindfolded and totally naked. Of all the elements that are intimidating about this particular scenario, bizarrely it’s the complete nakedness that’s bothering me the most. I’m feeling ridiculously vulnerable.

As he kisses me, I begin to relax again and feel the rope in his hands. He starts to wrap it around me slowly, whispering in my ear to ‘feel the rope’. My arms are folded behind my back, my hands gripping my forearms. He’s already explained that he’s no shibari expert, but it’s surprisingly comforting as the rope is wound around my upper body. In the back of my head, I still can’t help but think how ludicrous I must look with all my flabby bits hanging out and my boobs weirdly squished. But it’s clearly working for him and I force out the doubts and obediently kneel again, ready for him to fuck my throat.

I’m really liking the feeling of enclosure, like a big hug. And while balance getting up and down is tricky, he can use it like a carry handle to move me around wherever he pleases. I’m steered to the other side of the room, feeling the rubber mat under my feet, and bent over what I eventually realise is the odd shape banana chair. He’s instructing me all along but it’s still confusing, disconcerting and wobbly as he positions me face down with my arse in the air. It takes me a moment to realise that he has put on rubber gloves before he starts fingering my pussy – I’m mildly put out that it implies I’m some kind of skank. But at the same time, I’m reassured that he’s fastidious, particularly given his commitment to the lifestyle.

After a rough and not altogether pleasurable fingering, he puts on a condom and finally fucks me. I’m completely helpless and he’s grabbing my hair, pulling my head back. It’s rough, deep, noisy, and delicious.

He’s already regaled me with tales of his orgasm-control prowess, and espoused the virtues of loud, shouty, primal cumming. But I’m still surprised by the animalistic roar he emits as he shoots his load.

As ever, I’ve warned him that my orgasm is extremely unlikely. Any expectation has precisely the opposite effect on me. And besides, I prefer to cum with The Husband when I get home to my own comfortable bed. But of course he takes this as some kind of challenge and quickly recovers, eagerly returning to the task at hand. He pulls me upright by my convenient carry handle and I’m standing exposed once again as he considers his next move. I can tell from the flooring that I’m positioned near the frame and he starts attaching more rope to my arms. Eventually, I’m stood, legs spread, with my upper body secured by ropes and suspended to each of side of the frame.

I’m bound, helpless and excited, waiting and listening as he paces around me. When the deafening trance music begins, I know that his orgasm mission has begun in earnest – a mission where he plans to take me out of my head until my body has no choice but to react. He warms me up by stroking a crop over me, building gradually to stinging whacks which leave my tits with impressive looking bruises for weeks. Next, a sharp spiky thing is run seductively from my neck down to my feet. I’m slowly losing myself, relaxing into a trance-like state. A vibrating wand is held firmly against my clit while he expertly manipulates my g-spot. My legs are wobbling and unrecognisable groany sounds are coming from my very own mouth. Above the music, he’s forcefully and loudly instructing me to shout and scream… until I have an unexpected and primal climax.

Through our detailed preparatory discussions, I’ve stressed the importance of effective aftercare – I’ve learned plenty from my dabblings with Easy Rider. He’s suitably attentive, untying me slowly and sensually removing the rope before finally removing the blindfold. Then he leads me over to the bed, lays me down and holds me in his arms while I recover.

The Dungeon Master

My occasional dalliances with Easy Rider have definitely reawakened my interest in further BDSM exploration. When a Dom contacts me through Tinder I’m immediately curious. He hosts a long running kink party and it turns out that he’s extremely experienced and quite renowned. The idea of socialising in the scene is still leaving me cold but the invitation to visit his dungeon is pretty hot.

I don’t know whether I fancy him and find his rubber clad profile picture mildly comical, but I admire his commitment to the cause and the range of his experience. And the opportunity to progress my experience from suburban playroom to full-on dungeon is increasingly fascinating.

We’ve had a brief but reasonably informative message exchange when I agree to pop in for an exploratory visit one afternoon when I’m working nearby. It’s been a stressful and intense work day, I’m not sure my head is in the right place, and I’m horribly nervous as I knock on the door of the sprawling old house. But he’s friendly as he welcomes me into the house, reassuringly taller than me, and good looking in an older, dom kind of way. We’re stood close together in his hallway when he asks if he can touch me. I nod in agreement and in one deft move he puts his arm around me affectionately and grabs my hair, roughly pulling my head back. He’s holding me firm and I sigh, feeling the tension drain from me.

In one move the mood is established. He releases me to give me the grand tour. It’s not fancy and has a bohemian vibe that sets me at ease quite quickly. But the leftover mess from the weekend looks decidedly seedy in the cold light of day, with boxes of tissues, crumpled sheets on multiple mattresses, and a nasty pair of high heeled shoes abandoned in the middle of the floor.

I’m already thinking the whole place could do with a going over with disinfectant wipes when he shows me the medical room. It’s reassuringly sterile and pretty hardcore as he explains the complexities of needle work. But hospitals make me anxious and I find the whole concept of medical play pretty horrific.

However, the chair in the middle of the room is a different matter altogether. It is vintage medical chair with arm and leg rests and multiple recliner settings and the thought of being restrained and sprawled in it is an enduringly exciting prospect.

In the big room, there’s a huge frame over a padded vinyl mat, pictures of intricate ropework, 2 beds, an interestingly shaped banana chair, and an impressive sound and lighting system – all adding up to quite the fun looking party venue.

The tour ends there and we’re stood awkwardly when he grabs me again and shoves me to the floor. He sits on the edge of a bed with me at his feet as we discuss preferences, expectations and boundaries. I’m still reeling at the speed of transition from high intensity work role to that of submissive slut, so keep the conversation practical, express my interest in further exploration, and leave with plans for the following week.

In preparation, he sends me a detailed questionnaire to complete. It’s a standard and sensible step that establishes boundaries for all concerned. It’s also a process which I enjoyed greatly, spending a very pleasurable afternoon reflecting and gaining insight into the nuances of my most intimate fantasies.

And surprisingly, trying out the questions on The Husband gave me more detailed insight into his brain too. Just when I thought we’d delved into every element possible of his complex fetishes and preferences, I learn that he gets a boner for swishy ponytails. It’s by no means the most bizarre or unexpected reveal, but I do find it fascinating that after almost 30 year of intimate exploration, we continue to discover new things about each other – and ourselves.

Grudge Match

The online dating site I’d been using is becoming a little feral. In almost a year of searching for single middle aged men in a relatively small city, I may well have exhausted that particular limited pool of opportunity for now.

Tinder has become a surprising and interesting distraction, swiping through the multitude of photos of men triumphantly holding fishes aloft and proudly polishing their throbbing midlife crisis motorbikes. It was a resource that I had previously avoided, assuming that it functioned purely for people looking for spontaneous hook ups. But I’m surprised to see the huge range of profiles, from people looking for soul mates, clandestine affairs, a quick shag, or anything in between.

The Fireman had been my first successful Tinder encounter, he had deciphered my message app username from my profile and contacted me directly like the smooth old pro he is at picking up middle aged chicks in need of attention. But apart from him, sifting through the many contacts becomes tedious pretty quickly, continually describing, explaining, and even justifying my lifestyle preferences and interests to numerous naive newbies. Clearly, I have become a little wiser and quite a bit more cynical over the past year of dating.

My view that it is the home of timewasting amateurs is confirmed when I am stood up on my first date. My thinking is that if I am looking for great sex that’s based on friendship, then perhaps widening the net is a good way to connect with people on different levels. I definitely have a weakness for musicians, and I’m drawn to this guy for his creativity and tastes as well as his exotic looks. We make a last minute arrangement to meet for a quick drink one afternoon. Luckily, the combination of spontaneity and my current cynicism means that I don’t build my hopes up at all. I am pretty chilled as I choose my seat in the deserted bar. After 5 minutes he messages to say he’s delayed and I let him know I’ll wait. After 20 minutes, I leave, un-match him, and take myself out for a delicious lunch – and I’m convinced that the company was far more entertaining than originally planned.

I’m equally surprised to discover the number of familiar faces there too. My clumsy fingers are still getting used to the different swiping functions and in one very close call I accidentally ‘superlike’ someone I know through work and would never consider fucking – ever. He has constructed his profile expertly, to make him look far less of a toothless, withered, chaotic alcoholic than he is in real life. And I am convinced that he’ll recognise me, seeing through my thinly veiled glamorous disguise. Thankfully, he is characteristically unobservant and I quickly un-match when he responds.

Another match however turns out to be a briefly exciting prospect. We move in similar work and music circles, following each other on social media, sharing similar tastes, values, politics and creative interests. He’s not traditionally good looking, but I like his style, confidence and dry wit. And I know his ex-wife and mother of his young child…. It’s a small world. But on this occasion, I’m mildly hopeful things could line up well for a casual, non-traditional, friendship that fits well with the busy lives and responsibilities of all involved.

But ultimately, it’s too much of an odd set-up. After agreeing that the logistical opportunities are interesting and that we find each other attractive, the messages are minimal. We meet for coffee one day but seem to fall quickly into work-related gossip in a comfortable but non-flirtatious way, firmly rooted in the friendzone. We manage a slightly awkward hug and a peck on the cheek as we say goodbye and he even suggests a second date – one which unsurprisingly, never happens.

The Towering Inferno

What girl doesn’t love a fireman? And this one is funny, gentle, built, and hot too – he really is the stuff of fantasies. And he knows it.

He contacts me first, luring me in with pics of his smiley face, bulging biceps, and powerful thighs. He not only endures my multitude of cheesy unoriginal fireman puns, but completely joins in with it in a cute, flirtatious barrage of spraying hoses, shiny helmets, and greasy poles.

I haven’t been this excited for a date in a long long time. And when he walks into the bar, I’m decidedly dizzy.  He’s tall, muscly and friendly, and when his massive arms reach in for a hug, I weaken immediately. The flirtatious, cheeky, warm tone of the messages continues into real life and I giggle girlishly over our quick drink. While I know we’re getting on well, I’m not at all sure that he’s as into me, so I’m mildly taken aback when he leans in for a snog as we say goodbye outside.

It’s a soft, gentle, romantic kiss, and his huge stature wrapped around me is delightful.

On the way home, I’m immediately thrown into a spin of self-doubt and confusion in what is a typically me response to a very nice date indeed.

Of course it’s too good to be true when it turns out that his teenage daughter lives with him. Clearly I had been so carried away with the prospects of a muscly calendar-model of a fireman that I hadn’t paid as much attention to the details and logistics as I usually would before meeting in person.

But where there’s a will, there’s a way. And within the week, he lets me know that he has the place to himself for a few hours and I drive over to see if the reality lives up to the fantasy. He lives in a brand new development, above some commercial premises, and it takes me a while to find the carpark and doorway. So much so that I begin to think it’s all some kind of practical joke.

But sure enough, he sees my message when he gets out of the shower and greets me with his characteristic warmth. I stand awkwardly making small talk and drinking a glass of wine in the kitchen waiting for him to make the first move. When he does, it’s slow, soft, and romantic again and it makes a nice change from my more vigorous adventures of late.

Standing in the bedroom, he does the whole 80s music video style kissing my shoulders and slowly undressing me thing. I consciously have to stop myself from emitting an audible sigh of disappointment when I finally get my hands on his willy. But while it may be smaller than I had hoped, it is encouragingly hard and enthusiastic. And the fucking is intense, energetic, and much harder than the slow build up would suggest.

Eventually we collapse in a sweaty, panting, ravaged heap and feel surprisingly comfortable and relaxed together as he holds me in his lovely big arms and proclaims that we ‘fit well’.

But ultimately, I’m not convinced. His last minute booty calls and constantly changing plans quickly have me feeling insecure – after all, it doesn’t take much. He’s playing along with the boyfriend role but really just needs a convenient fuck buddy.

And while it’s not a deal-breaker, I’m mildly uncomfortable with his fixation with having his arse rimmed. I understand how hypocritical a position it is from someone who has written so much about loving arse play, but I’m just not the giving kind. If I’m going to shove my tongue into a fella’s poo hole, then it’s going to be The Husband – the man I love and whose butt I have neglected for almost 30 years!

The episode ends with me getting a bit over excited about the prospect of us spending a public holiday in bed together while his daughter is away. I cancel all existing plans, organise transport, get my nails did, and shave my minge, ready for an afternoon of filth and wine. But sure enough, he cancels at the last minute. The first time was disappointing, the second time was rude, and the third time just isn’t going to happen.

In a bizarre turn of events a couple of months later, I learn that the fireman’s flat has burned down. And no, it wasn’t me. Sitting watching the news one night, we recognise his apartment block in some spectacular fire footage. The whole building is destroyed, miraculously with no serious injuries, and 3 teenagers arrested for arson. In a brief message exchange he tells me that they lost everything and I send him well wishes and support, strongly resisting the urge to draw attention to the irony – even I recognise that it’s way too soon.

Dirty Grandpa

I’m getting slightly better at knowing what I want. Or maybe I’m just getting better at projecting my desired qualities onto unknowing and unwitting partners. Whichever way, it doesn’t always work out well and the run of misfits continues.

I’m not sure if I’m physically attracted to him, but his messages are cheeky, charming, and deviant. And he’s older, single, lives alone, and experienced in the swinging scene. It’s an attractive combination, particularly during a current dry spell.

I’ve been sick again and out of action. The bleeding during sex that had been hampering my sexual adventures has been put down to a polyp which has been successfully removed. At the same time, I’ve had a proper clear out and a IUD contraceptive device fitted, both for added protection and to help with my peri-menopausal symptoms. The upside is that my womb is sorted and ready for action. The downside is that I’m feeling exhausted, hormonal, bloated and decidedly unattractive. Perhaps some dating adoration is just what I need to start feeling fabulous again.

He’s the supervisor on a huge building site in the city. I arrange to meet him for a quick drink round the corner from his work on the way to meet a friend. He’s in the whole construction worker gear, complete with flouro vest, big dirty boots, and an impressive shiny helmet. While he’s not traditionally good looking, he’s got the whole rugged thing going on. And he’s cheeky, charming, and confident – I like him. To the extent that I feel an intense tingling when he tells me how much he wants to take me back to his site office and bend me over his desk there and then. In an uncharacteristically sensible move, I politely decline and agree to visit his place the following week.

But when I see him standing by his ute (again!) waiting to pick me up near my house, I wonder what the hell I was thinking and consider running away. He looks completely different in his own nasty jeans and cheap trainers with a cigarette hanging out of his mouth. Without the fantasy construction worker think happening, he just looks like a shabby, unkempt, dirty old man.

Everything is lined up though, it’s been a while since I had an adventure, and The Husband is excited about picking me up on his way home from work for an evening of our own. I decide to go with it.

His house is reassuringly clean and he has a beautiful if slightly scary dog. Both are factors that help me to relax reasonably quickly, especially combined with the large amount of wine that I quickly knock back for courage. The place is clearly set up for his sexually deviant lifestyle, complete with large recliner sofas and huge television with surround sound. The screen is still showing his last porn category and I point out to him that displaying a preference for teen porn probably isn’t the wisest move when trying to seduce a mature woman. We share a drink, a cigarette, and a laugh, and before long, he has his face buried between my legs.

He knows that I’m way out of his league, which makes him extra enthusiastic and appreciative, and makes me feel like an absolute porn star. It’s extremely hot. Soon we’re energetically fucking on his massive leather sofa – until he gets his leg stuck and we have to take a break.

Honestly, I’m not always as responsible about using condoms as I should be, particularly when I have a good idea about who I’m with and their sexual history. But this time I am extra careful. His sexual deviancy may be attractive on one level, but from what he’s revealed to me tonight concerning his occasional hiring of sex services and meth-fueled orgies with neighbours, his bare cock is definitely not going anywhere near me.

I’m increasingly drunk and end up on his bed with my legs in the air with him shouting ‘yummo’ and proclaiming that all his christmasses had come at once. When The Husband arrives, I head to the car in a slightly wobbly state to regale him with my tales of debauchery and we carry on the fucking into the night. The whole episode has a uniquely dirty quality to it. But it’s not one that I’m keen to repeat again in a hurry. And nor is my liver.

The Misfits

Of course I end up fucking the strangler dude. It’s been a particularly busy work week and I’m thinking that a few hours of rough sex could be just what I need to relax in time to spend a couple of days off with The Husband.

I’m exhausted, but excited enough to get dressed up in my corset and stockings, black dress and favourite leopard print coat. He picks me up around the corner from my house to take me to where he’s staying – a trailer park. It may be described as a ‘luxury’ holiday village, but it is still a trailer park. It appears to sum up the dirty shabby nature of the whole episode. But not in a totally wrong way.

He’s attentive, funny and flirtatious on the way there, and acts the gentlemen opening the door for me to climb out of the ute. But that’s where it ends. I’m used to a glass of wine and some gentle foreplay to ease me into a submissive state, but straight away he has me bent over the table spanking my arse – really hard. No niceties, just straight into the brutal play as he shoves me to my knees and tries to ram his pathetic cock into my mouth. I’m a bit stunned to be honest. We’ve chatted about different scenarios for a few weeks, but now I’m thinking that I really should have been more proactive in establishing boundaries and expectations for the visit.

I know I can stop at any time and that The Husband will be waiting outside shortly, so I go with it. His under-performing penis is clearly something he works with on a regular basis as he arrogantly mansplains female sexual pleasure to me while vigorously using his fingers to make me squirt all over the bed. He jumps up with a triumphant smile on his face, heading to the kitchenette in just his socks to fetch a can of rancid beer to thrust into my hand.

The mood becomes far more affectionate and chilled as we relax over our beers. And I’m sure that the squirting has given him a much needed boost to his sexual confidence. The afternoon culminates in him cumming over my face. I walk to the car park past the holiday makers looking like a hooker from a 1960s British film, complete with my leopard print coat, disheveled hair, and a dirty grin on my face.

He was enthusiastic about seeing me again but there was something missing for me. And it wasn’t just the lack of a big hard cock. Maybe if he’d have lived nearby I would have invested more time into exploring the potential. But then again, maybe I wouldn’t have. It was just a little cold and flat.

The continual chatting with prospective guys and juggling coffee dates is pretty intense. It’s often hard to work out what does and doesn’t do it for me. And as with anything, it comes in waves of nothing or all at once.

During a particularly lean time and a rare day off to myself, I spontaneously agree to meet a local man for coffee. The alarm bells should have rung when he sent me an unsolicited video of him fucking a fleshlight attached to his kitchen counter. While I’ve seen worse, it did seem an odd thing to send straight away, and I reminded myself that whatever came of it I should never let him cook for me.

The coffee shop was really busy and he’d already ordered his to take away before I arrived. He didn’t offer to buy mine or even wait with me, instead telling me he was heading outside. While he was reasonably good looking, he had a distinct lack of charm or even personality. As we walked along the seafront with our coffee, I felt like I was an unwilling participant in a job interview as he listed off his CV of sexual conquests. He appeared completely disinterested in me, not asking a single question, and at one point even interrupting me to hold a full-on conversation with the volunteers who were out cleaning the beach. I have never felt a more striking example of mutual incompatibility. And yet he was seemingly totally unaware, bizarrely pestering me to come to his flat for days after until he finally took on board my definitive ‘no’.

The Strangler

This quest is an emotional rollercoaster, and right now I’m struggling. Not only am I disillusioned but The Husband isn’t getting the most out of it either. He’s having a tough time at work and his head isn’t really in the right place. Before each date I annoyingly nag him incessantly to make sure he’s happy for me to go, adamant that I will stop the moment he becomes uncomfortable. But while he enthusiastically reassures me that my adventures are still making his dick hard, I’m not convinced that he has the emotional energy to process it fully.

And me and The Mechanic have finally run our course. After the initial excitement, he’d started to get complacent, expecting me to drive over whenever he had a night off, and not even bothering to feed me. On my last visit, ‘forgetting’ to order pizza when we’d already organised to have dinner was the final straw.  There were other complicated reasons that led to a mutual agreement to stop seeing each other. But essentially, the magic gradually dissolved. The quietness that I’d initially interpreted as dark, brooding and mysterious ultimately revealed itself as moody, petulant and selfish.

He was my first real boyfriend experience and I really really enjoyed the whole hanging out, chatting and cuddling on the sofa part of it. And of course the sex. The size and angle of his cock seemed to have some kind of magical powers that made me squirt every time, becoming such an issue that I wouldn’t get on the bed without putting a towel down first.

I know it’s time to move on, I want to feel comfortable not continually second guessing and taken for granted. But I’m also pretty down and disillusioned about it all.

It’s forced me to reflect on what it is that I’m really looking for and what works in our relationship. The Husband is way ahead of the game than me on the research and I catch up listening to podcasts and reading my new self-help bible, The Ethical Slut. Both are showing me a vast range of positive and non-conventional options and variations for experiencing sexual relationships. Most importantly, it’s giving me a new language to process and understand the feelings, experiences and preferences I already had.

While The Husband is a monogamous fetishist, I definitely lean more towards the polyamorous end of the spectrum. I really enjoy getting to know someone, developing a relationship, and falling for them just a little bit. I’m officially addicted to the excitement of ‘new relationship energy’ and absolutely adore the romantic feels of a ‘limerence’ rush. But it is equally the biggest downside – I’m opening myself up to new people and making myself emotionally vulnerable in the process.  It’s exhausting.

I’ve continued chatting to people online even if I haven’t been actively looking. But the amount of fugly, illiterate, dull, morons is so disheartening. Who knew it was so difficult to find an open, honest, clean, sexually confident, politically enlightened, mildly attractive, interesting person to hang out with was so fucking difficult?! I don’t think I’m particularly high maintenance, I just want someone to make me laugh, order the pizza, pour the wine, and fuck me into next week before sending me home to The Husband.

I think it’s a pretty straightforward offer, but right now it appears to be the holy grail.

I throw myself back into the online dating game with a slightly jaded degree of gusto. When in doubt, follow the wise words of the goddess Peaches, and ‘fuck the pain away’.

While I still know what works for me and how I want to feel with someone, I’m learning that I need to be a bit more flexible in my expectations. After all, I didn’t have butterflies when I met The Mechanic – that came after he snogged me and threw me onto his bed. Nevertheless, there needs to be an initial hook that gets me interested, whether it’s a cheeky glint in their eye, a saucy comment, their enthusiastic appreciation of my ample assets, or just an impressive dick pic. Ideally, all of the above!

So I have tried being a little less rigid and going with the flow more. My new approach has led to a couple of interesting encounters and I’m clearly developing a preference for rough and ready tradie types. Right now I’m surprised if a date doesn’t turn up in a ute.

I’m keen to get back on the horse but end up making a few impetuous decisions that lead to a couple of mildly unsatisfactory encounters. The first comes after an unsolicited late night message from a dude looking for a hookup while he’s in town overnight for work. I explain that it’s not my style and wish him well with his search. But he hooks me in with some cheeky banter and I’m home alone and bored, so we chat late into the night. He’s going to be in town regularly over the next couple of months and our sexual interests are definitely aligning as he tells me all the things he wants to do to me.

He’s a tall, bald, bearded bear of a man, with an impressive line in dominant sex talk. The enthusiastic messaging continues the next morning and I agree to meet him for coffee before he heads back home. It’s the quickest meet yet.

Physically he’s definitely my type and there’s a really attractive mix of humour, flirtation and sexual intensity as we drink our coffee. I’m so into him that I make the uncharacteristically risky decision to accept his offer of a lift home just so I can snog his face off. I get into his impressively big shiny ute and we drive to a popular picnic spot where we get down to kissing each other. He does all the things that make me weak – kissing my neck, whispering filth in my ear, and gently putting his hand around my throat. But he is a big and powerful physical presence and as his grip tightens, I have the briefest intense wave of panic, shocked by my own vulnerability and wondering what the fuck I was thinking.

It’s still incredibly hot, but reality rears its head again when he unleashes his disappointingly small penis in a state of flaccidness which in no way reflects his otherwise enthusiastic demeanour. I repeatedly refuse his requests for me to wank him off until he reluctantly agrees to drive me home. He gives me one last aggressive kiss and neck squeeze before I jump out of the car slightly stunned and with promises to get it on next time he’s in town.

Diamonds are Forever

So the exploratory date with Easy Rider was quite the success.

The shtick with him is a far cry from my usual search for emotional connection and affection, but it was definitely fun. I’m left feeling a bit shell shocked and confused at first, trying to work out how to process a totally new kind of ‘relationship’ that basically involves me heading to his house for a quick glass of wine, an exchange of pleasantries, and straight down to hot play and brutal sex before heading home an hour later.

It’s the equivalent of a mid-week therapy session – in fact, half an hour spent bending over in stocks feels just like I’ve completed a particularly tough yoga class. And the timing works well for The Husband too. I’m home in plenty of time to carry on the fun with him, and we even get to have dinner together.

I enjoy his creativity and enthusiasm, and the prospects for exploration are very promising indeed. Now that we know we’re sexually compatible, we exchange increasingly detailed messages on ideas and preferences. This involves my love of cum, and his enthusiasm extends to him heading straight out for a blood test and the all-clear.

On the second visit, my nervousness is dramatically reduced but the excitement isn’t. After the perfunctory glass of wine and a quick snog, I’m chained to the cross and grinning with anticipation as he lurks next to his table of implements deciding what to do first. My grin soon shifts when he starts to test my reactions to the flogger, paddle and crop.

It’s all going swimmingly as he releases my wrists and shoves me on my knees, fucking my mouth and turning me into an gagging, eye-watering, drooling mess. I am continually surprised how much I enjoy it.

Eventually bending over the horse, he introduces me to his vibrating butt plug. It’s ingenious and absolutely delightful. So much so that while he fucks me hard and increases it’s intensity in my bumhole, I very nearly cum standing up – no mean feat. The session ends with me on my knees and him cumming all over my face before taking a photo for The Husband.

It’s a unique set up that lasts way longer than any of my other friendships. Primarily because it’s only an occasional thing. But also because it’s a very straightforward arrangement. The boundaries needed to be worked out initially, especially while I reconcile the fact that this one is not going to involve date nights with pizza and cuddling – just two people who like each other indulging in brutal, depraved sex.

My boundaries are further tested on one particular session which puts me off returning to his playroom for a while. And it’s not even his sadistic creativity which pushes me to my limits. It’s my own aging, broken body! I’m bent over with my legs spread and neck and wrists locked into the handmade stocks. Apart from the impressive array of anal toys, the enduring memory is of the toil it took on my aging knees and hips to stay in that position for a prolonged period of time. My reward is being sent home to The Husband with a bum full of cum contained by a very pretty diamante butt plug.