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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.

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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.

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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.

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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.

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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’.

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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.

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Easy Rider

Years ago, when The Husband and I were on our painful break, I had a brief dalliance with the kink scene. A chick from work was being paid on the side for running a BBW chatroom. Chatrooms and message boards were all completely new to me, computers were the size of giant pumpkins, and I could have vacuumed the entire house in the time the dial up internet took to load a single page. But the possibilities for a 30-something working single mother to meet people without going out on the piss every night off were appealing. The work chick set up my computer, explained the basics, and sent me on my way. And before long, I had migrated to the BDSM arena, utterly fascinated and completely immersed in the chat about pain, restraint, humiliation and punishment.

Clearly, The Husband is extremely sexually submissive. And up to that point, I had taken on the role of Domme with style and enthusiasm. But I was equally drawn to his rough, assertive dominance and now I was keen to explore just how submissive I could be.

It was almost 20 years ago and he was my first internet date and my first proper Dom. He was a short, stout, rich, older arrogant bloke – all features which fit the profile. But he lacked the kindness, sensitivity and intelligence that I now understand are central to the whole thing working effectively. While I was fascinated by the lifestyle, I was ridiculously naive, heartbroken and damaged, and the whole episode makes me uncomfortable to think about even now. Basically, it was doomed for failure because neither of us actually liked each other, let alone ourselves.

On the other hand, I was able to explore some of my biggest fantasies and had some of my hottest adventures when he escorted me to some incredible parties, ones I would have been unlikely to find on my own and even less likely to ever been brave enough to go alone. The parties were pretty vanilla group sex affairs, and I adored them. The BDSM exploration was far more psychological and at first, I enjoyed the novelty of doing whatever I was told. I also enjoyed lightly exploring my pain threshold with nipple clamps, spanking, hot wax, and restraint. Obedience and pain were so deliciously different to my usual preferences.

While my exploration over 2 decades ago was merely toe dipping, the visible BDSM scene is now way more complex, and divided into an increasingly accessible and titillating array of specialist, nuanced sub scenes. I’ve said it before, the contrived amateur dramatics of the mainstream fetish scene does very little for me. I have no interest in drinking cheap wine and eating cocktail sausages with people dressed in ill-fitting latex and dog collars talking about the comparative size of their butt plugs. And while I’m aware that the club scene is more sophisticated nowadays, I’m feeling too old for clubbing right now and may well need to build up to that once I’ve met a suitable mentor.

But I still adore being sexually submissive. Being dominant at home, and a strong feisty woman in my everyday life, it is a delicious and welcome relief. The right combination of words, eye contact and sexual confidence turn me into a quivering wobbly mess. So it’s no surprise that I’ve been starting to explore this a bit more in my online discussions and in real life.

He is single, early 50s, reasonably fit looking, has a cheeky glint in his eye, and is a biker – we name him Easy Rider.

I’m not actively looking for a new friend when his message pops into my inbox. But he’s interesting, flirtatious, kinky, and can string a sentence together. And he has very particular tastes which he gets down to it pretty quickly, sending me pictures of his playroom. The décor is more 1980s suburban blokeyness than the classy chrome glamour of the movies. But the homemade St Andrew’s Cross, stocks, and horse, as well as the table laid out with an array of toys, butt plugs, whips and crops, shows an impressive degree of skill and imagination.

And he has a really great looking cock. I know it’s not supposed to matter, but it does – a fact that I am increasingly coming to realise on my current quest.

I’m heading out to see my friend’s band play and arrange to meet him beforehand. I would know too many people in the first pub he suggests, and there is an unusual amount of activity in the city that night, so by the time I manage to park up and meet him outside the third meeting place we agree on, we’re both a bit over it. But we eventually get a table in a notoriously shitty pub and get down to talking details. He’s a bit shorter than I had imagined but I like the cut of his jib and he’s wearing a lovely pair of cherry red Doc Marten boots.

We share a lot of the same music tastes and a disdain of the mainstream BDSM scene. It’s all going so well that I ask him outright about his politics. This is becoming a thing for me now – I’m sick of emotionally investing in a scenario only to find out that he’s a racist, homophobic, misogynistic prick. He deals extremely well with my interrogation, but as we walk towards his car I’m still unsure if there’s much sexual chemistry between us and detect a slight whiff of chippy defensiveness that is decidedly unattractive, especially when I’m looking for a sexually confident and dominant partner. My main reservation is whether I’m too feisty for him and whether his squeaky voice has the gravitas needed to pull off the patter effectively.

But the kiss goodbye is encouraging and the messaging over the next few days is increasingly hot. He regales me with tales of his ‘pussy pump’ and ‘anal hook’, toys that even a supposedly enlightened chick like me has never even heard of. And when he encourages me with the words ‘good girl’ he definitely has my attention.

The thought of him torturing and using me has also piqued the interest of The Husband, who is completely getting off on the prospect of being made to watch. I put the proposal to Easy Rider and he’s equally excited by the idea… all 3 of us are keen to explore the possibilities.

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Point Break

It’s a fruitful and exciting time, awash with sexual energy.

The Mechanic and The Girlfriend are my two main friendships and proving to be very promising indeed. But I’m on a roll and still addicted to the thrill of meeting new people. I’ve been chatting sporadically to one guy who hasn’t particularly wowed me with his wit and repartee, but his photography skills and hot surfer’s body have kept my attention.

The practicalities line up too. While my current friends have limited availability, the surfer dude lives alone in a convenient spot for impromptu visits on the way home from work or a night out. While there’s no particular banter, he’s laid back and experienced, and we seem to be after the same thing.

I’ve found that fitting in a quick date helps me fight the mundanity of the working week, treating it as a reward to motivate me to smash through deadlines. I’ve arranged to meet him for a late afternoon beer on my way back from a meeting and arrive at the pub a bit earlier than expected. When I message him to let him know I’m there whenever he’s free, he asks if I want to drive round to meet outside his house. When I point out how shabby that sounds, he backtracks, claiming that he’s feeling lazy. It’s not a particularly good sign – laid back is one thing, too lazy to walk round the corner is another.

But I’m there now, it’s a sunny afternoon, and I may as well finish my drink. When he arrives, he’s way more dishevelled than I expected, but in a windswept, outdoorsy, surfer kind of way. And he’s smiley, friendly and very easy going company. We spend a comfortable hour chatting, only distracted by the brassy blonde drunken old bird at the next table who’s wearing a short skirt and apparently no knickers as she flashes her minge to her fancy man. And I thought I was the disrespectable one around here.

Me and surfer dude have talked through our expectations and wish lists. While the lack of banter still worries me, his hot body, chilled attitude and easy availability continue to interest me. He walks me to my car and kisses me confidently before cheekily asking for a lift home. For such an active fella, he really doesn’t seem to like walking.

I feel awkward having him in my car, but even more awkward saying no, especially after the conversations we had been having. A couple of streets away, we both get out of the car to say goodbye and grab another snog. The results are sufficiently tingly for me to keep him on hold as a convenient booty call.

It only takes a couple of weeks before I’m calling on him to help me out during the ridiculously horny aftermath of my girlfriend experience and decide to pop over for a quick shag. In the relatively short period since I’ve been exploring new relationships, I am stunned by people’s different understandings of what it means to be a ‘friend’ with benefits. Surfer dude has said all of the right things in response to my comments about the importance of hanging out and having a laugh together. But his reality is completely different as he ushers me to his room to get straight down to it. It’s a dark, dingy, messy house and there isn’t even the offer of a drink let alone a smattering of small talk to break the ice.

To be honest, I’m that horny that it doesn’t even bother me at the time. The room looks like a 1980s student pad with bare floors and hippy wall-hangings and we’re stood next to the large futon snogging and quickly undressing. It takes me back to the fumbling one night stands of my teens – only this time I’m completely sober. He’s remarkably skilled at foreplay and I’m feeling extremely wet and wanton very quickly. While I’m not complaining, his moves are pretty rehearsed like he’s ticking off a well-timed checklist until he’s straddled over me announcing his intention to put on a condom and penetrate me. I’m absolutely gagging for it by the time he does and am completely lost in the fucking as we get into our good old missionary position rhythm. It’s surprisingly effective and I actually cum, something that I don’t even expect to happen with my most adored companions. He looks understandably pleased with his performance and shoots soon after, collapsing on his back next to me.

While the sex was surprisingly good, the post-coital interaction was equally awkward. We congratulate each other on a job well done as if we’d just completed a particularly impressive gym workout. The conversation is stilted and there isn’t even the offer of a cuppa, just an overwhelming desire to move on. I quickly get dressed and he walks me to the door, telling me how super-keen he is to repeat the episode again soon. I head home feeling sexually satisfied, but also slightly dirty and used – and not entirely in the positive and empowered way that I’m aiming for.

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Snatch

I’m obsessing about the possibilities. Her curvy, tattooed, pinup look is the stuff of my fantasies, and she agrees that it’s the first time that she’s had an instant connection in ages too. She’s a single mother who only gets every other weekend off and we make a plan for the Saturday night. She drives over to get me so that I can drink and the messaging from both The Husband and The Lorry Driver becomes increasingly excitable as the day progresses.

The aesthetic of the two of us together is a stunning prospect, so we’re going for the whole pinup, seamed stockinged look. The Husband takes some hot photos of me as I prepare for my first full-on lesbian adventure of the new era.

I am ridiculously nervous, and think I’m going to vomit as the pickup time draws near. She messages me when she’s nearby and I head to her car armed with 2 bottles of prosecco for courage. She looks very cute in a dress very similar to one that I have at home, nude stockings with red seams, and red lipstick. But she’s distracted by her ex who is messing her around about childcare for the following morning. She chats away as we drive across town, but it’s friendly chat with no hint of sexual tension at all and I have no idea how this is going to work and how much of a dominant role I’m going to have to play.

Back at her house, the similarities in our taste continue and her vintage décor is freakily like my own. We crack open the wine and she gets out a cheese board – I wasn’t expecting to be fed too! It turns out that she’s been ridiculously nervous all day and is the same whenever she has a new adventure. We’re on opposite sides of the breakfast bar in the kitchen and she’s sharing all sorts of heavy shit with me about her life. It’s the kind of conversation I would have with a new friend, but really would not count as a preamble to hot lezza action.

Before I know it, we’ve finished the second bottle of wine and still haven’t made a move on each other. She’s frequently exchanging messages with The Lorry Driver too which is really disconcerting as I’m honestly not sure to what extent he’s instructing her, or to what extent she’s genuinely attracted to me. And her tales of extreme submission and risk-taking have intimidated me so much that I’m increasingly unlikely to make the first move no matter how much I want to snog her face off.

Eventually she comes round to stand in front of me while I’m perched on the bar stool with the tops of my stockings showing. We kiss and I grab her towards me between my legs. She whispers that she’ll do anything I want, and I’m reeling so much that I have no idea what I want first. Before I’ve had time to think, she’s got her hand up my dress pushing her fingers into my pussy as I stroke and kiss her tits. I just want her naked and in bed right now.

I go to the toilet and when I get to the bedroom, she’s turning the bed down, moving the table for my wine, and generally getting ready, more like a saucy chamber maid than a woman overcome by passion. I sit on the side of the bed pulling her towards me and moving my hand up her skirt. She swiftly moves away to take off her dress and I follow with mine. We’re snogging on the bed, a tangle of boobs, hands, stockings, and lipstick. It’s absolutely lush.

She’d already sent me photos, so I knew she had a pretty pussy, relieved that it didn’t look like a car crash. And my concerns about tasting it were equally unfounded. It’s official, I love eating pussy, well this one at least. I took to it immediately, munching away enthusiastically, and instinctively doing to her what I like done to me.

The highlights of the whole episode include her sitting on my face while I grabbed her voluptuous arse, and then watching her face as she looked into my eyes gently biting on the softest flesh of my tits, leaving delicious tiny bruises which lasted for days. While I was lost in the moment and decidedly dizzy from all the wine, her photography skills were impressive, often capturing a sneaky image to send to the boys and remember the night by. One photo in particular I’ll keep forever to remind me of the hottest moment by far. I had her bent over with her arse in the air, grabbing her hair and whispering that she was my slut while I gently played with her pussy. Kneeling between her legs I focused on getting my fingers into her wet cunt, fucking her harder and harder until I had most of my hand in her, while she moaned louder and louder, and eventually came. At some point, unbeknownst to me, she’d managed to get the camera underneath, capturing a fabulous shot of my arm in action and an extremely determined and filthy look on my face.

We’d been at it for at least an hour and stopped for a breather around midnight, both aware that the boys would be waiting with baited breath to hear of our progress. Not without reason, The Husband had concerns about The Lorry Driver turning up unannounced for a piece of the action. And sure enough, she jumps up excitedly, announcing that “Daddy’s here”.

While unsurprised, I’m really not happy. This was never discussed and I let her know that I’m uncomfortable with it. She tries to reassure me that he just wants to say hello before heading to the door to let him in, and I immediately message The Husband to let him know that it’s time to come and get me.

Despite my uneasiness, I give him an enthusiastic hug when he enters the room, perhaps because he’s so much hotter than I had anticipated. Me and the chick are sitting on the bed, close to the end of the third bottle of wine and looking decidedly ravaged. He is sat in an armchair towards the end of the bed with a satisfied, confident and domineering look on his face. He’s dressed in a simple tshirt and jeans, has cropped hair and a fit body for a 40-something year old, and he has a real bad boy tattooed look about him. It had been really hard to gauge from the few photos he’d shared with me, ranging from the hotty sat before me to a decidedly paunchy Jehovah’s Witness look.

When he asks if we’ve had a nice time we both answer enthusiastically and she excitedly boasts that she made me squirt. As ever, her impressive ability to talk gets us through the 20 minutes until I can make my exit. When I get the message telling me that The Husband is waiting outside, I swiftly get my stuff together while they stand talking in the sitting room with his proprietary arm around her. I really have no idea what the etiquette is for this kind of awkward situation and head to the front door waving a cheery goodbye. She comes over, snogging me passionately and letting me know that I can see her any time I want.

I run enthusiastically to the waiting husband, buzzing from the adrenalin, excitement and incredible hotness of the whole episode. I am incredibly turned on by the success of my lesbian endeavours and now, by the prospect of what we could all do together too. I feel like I’ve only just scratched the surface with her, and am now equally intrigued by him too, thinking that my ultimate FFM fantasies are now a distinct and imminent possibility.

I’m still pretty drunk and The Husband has come up with a plan for us to indulge in some MDMA to make the most of the decadent episode. On the few occasions that I take it, I’m usually really anxious and nauseous at first, while he immediately throws himself into the effects becoming blissed out and horny just by looking at it. This time, I’m drunk, buzzing, and already on a high from my adventures, talking effusively about how hot it was, how hot they both are, and how I can’t wait to do it all over again, only more so. But he hasn’t had the build-up that I have and hasn’t had time to process what’s happened, so he ends up being the one who’s anxious and nauseous, hit by the whole reality of jealously instead of the warm, perverse glow of cuckoldry. But it’s only a brief wobble and within no time, we’re back on track, talking it through and completely loved up.

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Her Girl Friday

I’ve said it before, the most exciting and impressive experiences seem to come from the most unexpected sources. And my first girl-on-girl session is no exception.

I have listed myself as bisexual on my online dating profile but the amount of interest from women is disappointing. There are way more men on the dating site than women, and so us chicks don’t tend to become full members, and end up restricted to ‘winking’ at each other without actually connecting.

There are regular contacts from couples wanting me to join them, but the idea makes me nervous. Sex with a fella and another chick is one of my ultimate and most enduring fantasies. But my last experience years ago has made me super cautious about getting the dynamic right. It should have been great, but she was into me, I was into him, and he was into her – no one was into each other! Next time there has to be equal attraction, attention and satisfaction for everyone involved, in a completely egalitarian regime.

So I’ve decided to focus my attention on a one-on-one experiences first before developing a group scenario. My first message from a single woman is encouraging – she’s my age, newly separated, and a photographer with a cute face and amazing looking breasts. She’s also particularly kinky, extremely submissive, and very deep into the fetish scene.

We meet for coffee at the botanical gardens. It’s a sunny day and a beautiful spot. But in real life she’s way more frumpy than I expected with a decidedly mumsy, art-teacher kind of look. As we hug, there is absolutely zero sexual chemistry. We hang out for a really pleasant couple of hours, swapping notes on our adventures so far and even finding out that we’d been chatting to the same guy at one point. When he went quiet on me, it turns out that he had entered into a full-on dom situation with her. I underestimated the degree to how committed she is to her new found fetish freedom and at times she strikes me as slightly manic. While I’m not madly into scene stuff, and don’t fancy her at all, just being able to talk to another chick about sex-positive lifestyle choices is a welcome change and we agree to stay in touch.

But as ever, as one scenario fizzles, another opportunity is round the corner.

At the same time, I had started chatting briefly and intermittently to a long distance lorry driver. I wasn’t sure that we had much in common and I couldn’t really tell if I fancied him from his photos. But I was intrigued by his kinkiness and dominant streak – not in a cheesy dress-up roleplay kind of way, but a deeper commitment to exploration, including a particular obsession with double penetration.

Just as I am beginning to lose interest, he mentions a bisexual female friend who he thinks I’ll hit it off with. This is just the first sign of his masterminding filthy planning skills. He asks if he can share pictures and sure enough, we look like an ideal match. He definitely has skills.

She is a couple of years younger than me, and a shorter, cuter, lighter-shade version of me. Where I’m into the saucy black pinup look, she is the fluffy pink version. And she’s curvy, tattooed and dirty. I adore her style and sassiness and am completely hooked. The whole aesthetic appeal of the two of us together is intense – I definitely would pay good money to see that movie.

She too is submissive and it turns out that The Lorry Driver is her ‘daddy dom’, facilitating, organising, preparing and watching her sexual adventures. He’s the caring protector, a role that isn’t a million miles away from that of The Husband, it’s just the mental stimulation angle that’s slightly different.

As I’m the sexually dominant one at home, I much prefer to be submissive when I play away. But the idea of being in control with her is an increasingly attractive prospect. Where I’ve never exchanged flirty, dirty messaging with a chick, I’m surprised at my skills. The messages and the photos escalate quickly and we agree to meet within a few days, incredibly hot for each other.

I’m super-nervous about our coffee date. I already know that I fancy her but have absolutely no idea how to flirt with a chick, let alone what I would do if we actually got down to it. I had got off with a few women in my younger years, but they tended to be drunken or drug-fuelled fumblings that usually involved waking up with my face in a half eaten kebab and trying to piece together the details. I know that I’m visually attracted to women, and relish the thought of getting my face buried into some lovely soft boobs. But I’m really not sure how I’ll take to the realities of eating pussy, and my fantasies always involve a dick at some point in the proceedings.

I get to the cafe early and when she arrives, it’s like having coffee with an old friend. She’s not as glam in real life, but then again, neither am I. We talk parenting, travel and her work. She does most of the talking and sharing but I put it down to nerves. After an hour, she looks around for a toilet and there doesn’t appear to be one, so I suggest moving over the road to the pub, surprising myself with my smooth moves.

We’re sat at right angles to each other on the banquette seating but I’m still struggling to pick up on sexual signals and really not sure if she fancies me or not. But we’re enjoying each other’s company and having fun sharing our lifestyle and dating stories. In fact, her adventurousness blows me away and I reckon she is literally the most dirty woman I have ever knowingly met. She describes one particular scenario which the daddy dom had set up for her, involving 3 complete strangers from Craigslist arriving at her front door to fuck her repeatedly while sending photos back to him on his travels. It’s intimidating to meet a woman filthier than me, but also incredibly hot.

When it’s time to go, I head to the toilet and she joins me. We’re in adjacent cubicles and once we’re done there’s a moment at the door where we both hesitate. Days later, she tells me that she hadn’t needed to piss, but had been playing with herself instead. And that she had wanted to snog my face off at the door. We hug goodbye in the street, and it’s soft and lingering. We agree to see each other again soon, and within a week we’re in bed together.