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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 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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The Boyfriend Experience

Me and The Mechanic have become a regular thing, getting together every other weekend when he has the house to himself. We’re quite smitten with each other, messaging regularly to break up the day with photos of my tits and compliments from him. But my previous visits have been time constrained for one reason for another, and now we’re finally planning a relaxed evening together. The plan involves him driving over to pick me up round the corner from my house in the afternoon, cooking me dinner, pouring me wine, fucking me senseless, then eventually dropping me home when he’s done.

I’m excited for date night and so is The Husband. He helps to douche my arse, and packs my preferred bottle of wine, waiting for me to leave before going for a run to burn off some of the nervous energy. I forgo my usual saucy stockinged look in favour of comfort befitting for a cosy night in and wait for him to message when he’s close by. As I get into his ute, I’m worried I might be spotted by someone I know, feeling seedy and nervous. And I haven’t seen him for a couple of weeks so the reality of the stout bald middle-aged bloke next to me is a bit jarring against the mysterious dark fantasy man conjured up throughout our saucy messaging.

We’ve been sharing sexual scenarios for the past couple of days and he’s taken his mission seriously. When we get to his place I’m standing next to the kitchen counter when he comes up behind me, moving my hair aside and kissing my neck. He caresses and undresses me slowly and any doubts are quickly put out of my head. He turns me around and before I know it, he has lifted me up onto the counter and spread my legs with each foot resting on a bar stool. The idea of being perched, half-naked, and legs splayed on a breakfast bar would normally fill me with panic and dread, but he achieves it with a surprising and reassuringly graceful manoeuvre, particularly for a woman of my age and stature!

He’s kneeling down and enthusiastically feasting on my pussy while I writhe and moan, amazed at my brazenness and trying to force concerns about food hygiene from my mind. He stands up to kiss me, with his hard cock rubbing against me and I’m desperate to feel him inside me. I lift myself up with my arms and lower myself onto him, grinding, grabbing, snogging and completely abandoned and unselfconscious. It’s a difficult position to sustain and I put one foot on the floor, one on the rung of the stool and he uses his fingers again, making me squirt all over his carpet. He then turns me round, bends me over and fucks my arse until he explodes. It’s absolute pornstar stuff – messy, sweaty and delicious.

We’re both sufficiently blown away by the intensity of it and head out to the garden with our drinks. There’s lots of affection as we lie together on the outdoor sofa getting drunker and eating pizza before giving it another, more relaxed go on the bed. We’re both getting more comfortable with each other, and therefore more confident.

Equally though, it’s tricky terrain. It’s a first for both of us in the intimacy stakes and we’re constantly having to discuss and renegotiate our boundaries. In one message exchange, I reiterate my expectations and he reveals his first signs of possessiveness: “So I have to treat you like a princess, use you like a whore in the bedroom, and be ok with sending you home to your husband?”

That is indeed the size of it. On the plus side, he gets amazing sex, intimacy, friendship, and no risk of a crazy chick moving in on his family and home. It’s a pretty good deal all round if you ask me.

Apart from the kitchen sex, my other favourite Mechanic episode involves a bottle of prosecco, slow cooked garlic lamb, and a bit of light bondage. Again, he picks me up from close to my house. But this time, I’m dressed up for filth, wearing stockings, heels, see-through blouse and black satin pencil skirt – the full saucy secretary look.

And he’s put a lot of effort into preparing the night’s proceedings too. We’re snogging as soon as we get through the door as he steers me to stand with my back towards the wall. I can tell that he’s got a plan from the cheeky glint in his eye. He gently ties my hands together and lifts them above my head to attach to a special hook he’s drilled into the wall. He’s kissing, licking and groping me all over and my legs are already getting pretty wobbly by the time he brings out a remote control vibrating toy he’d bought for the occasion.  It’s not long before I’m untied, bent over the sofa, and it’s me that he’s drilling – him in my arse and the toy in my pussy. It’s totally breathless, sweaty stuff.

More importantly, the intimacy is a first for me and The Husband. All along, I’ve been clear about wanting a regular boyfriend, but the reality of sharing me on that level is slightly more challenging than the idea. He would definitely prefer me to have a stream of casual encounters – for fetish reasons more than emotional ones. We talk it through incessantly, with me checking that it’s still working for him each time and him reassuring me that it is when I come home with a fresh load of cum for him to clean up. In addition, he’s protectively picking up on the possessiveness signals and is more aware than I am that I’ll reach my boredom threshold soon enough.

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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.

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Dirty Rotten Scoundrels

It’s been an incredibly horny week, including my first proper full-on lesbian experience. I’m awash with hormones and buzzing with sexual energy. I have a couple of regular friends who are really doing it for me, I feel like my fanny is super-charged right now, and finally all of the faffing around seems to have been worth it.

I’ve been to a work thing in the morning before heading to see The Mechanic. I’m looking work-ready on the outside, wearing a frumpy black dress and flat shoes. But underneath, I have fancy new satin underwear, opaque black stockings and no knickers. No-one would know that I’m heading for an afternoon of filth.

He’s been messaging me his plans over the week. They involve him meeting me at the door in his underwear and ravishing me straight away. We barely even say hello before we’re snogging each other’s faces off and I’m standing in his hallway half naked. He’s rock hard and pushes me to my knees to take his cock in my mouth. Each time I see him I’m shocked at how thick it is.

When he pulls me up again, he stands behind me, grabbing my tits and kissing the back of my neck – a particular favourite of mine. My legs are shaking and I’m already gushing as he bends me over the back of the sofa to fuck me. He’s grabbing my arse with his big rough hands and fucking me hard. I haven’t been in the house for more than ten minutes and already I’m wobbly, wet, and whimpering.

He pulls out and moves round, to stick his cock in my mouth while I’m still bent over the sofa, getting me to suck it clean. He’s got a determined look on his face, like a man on a mission, and I like it a lot. He leads me to the bedroom where he gets to work on my bumhole with particular enthusiasm. I’m on my back, he’s licking my pussy and fingering my butt. This time, he’s confident and unhesitant, knowing how much I like it. And soon enough, he’s straight in there.

I’m clearly relaxing with this dude. We’ve had the safe sex discussion and worked out our boundaries and expectations. The result is that I’m getting more into it each time I see him, not getting hung up on what he thinks of me or what I look like, just enjoying the sheer sensuality, losing myself in the moment, and finally letting my inner slut reveal herself. Now he’s kneeling over me, holding my stockinged legs straight up together to one side while he thrusts hard. I actually ask him to shoot his load “into my tight fucking arsehole”. And obligingly, he explodes.

When he’s recovered, he makes us a cuppa and we lie in bed stroking each other and chatting intimately, regaining our strength. After a short tea break, we’re soon at it again. He’s playing with my pussy and watching my face intently as I get more and more turned on, writhing and gushing. I have a little go at riding his cock but I’m way too slow and steady for him, he’s much more vigorous and energetic. In fact, his stamina is so impressive for an old dude, that it’s me who has to tap out when he goes for my arse a second time. My legs are shaking, my bum is leaking, and I tell him I have to stop. In a very slick and gentlemanly fashion, he rolls me over and swiftly wipes my arse, waiting for me to get my breath back.

Eventually, I’m on my hands and knees at the edge of the bed with him stood up, fucking my fanny from behind. I’m groaning and actually shout that I want both my holes full of his cum. Again, he obliges.

I’m quite shocked at my vocal filth and by how abandoned I’ve been, and it’s all extremely promising. I’m also starving hungry and pretty exhausted from all the physical exertion and need to get home quickly, grabbing my clothes and dashing off. Even though it was only ever meant to be a quickie couple of hours, we’re both left feeling a bit unsure and awkward.

There is family stuff to do tonight, as well as me and The Husband indulging in the aftermath of my afternoon adventures. Amidst the chaos at home, we do manage to find some time make the most of my filthy ways, having a great deal of fun playing with my new monster dildo.

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That Awkward Moment

We live in a city. But it’s a relatively small city. And we know a lot of people.

With the amount of new friends I’m making, awkward encounters are becoming a reasonably regular occurrence. It’s a situation that’s further complicated by the fact that my early explorations into all this involved me making some impetuous and ill-considered moves on mutual acquaintances.

My early dalliance with a work colleague is a perfect example. While my work, family and social lives are reasonably compartmentalised, all clashed together on one potentially awkward evening. A mutual friend had invited Mad Max out to an event which The Husband and our kids were also attending! While I was uncomfortable, I was utterly amazed by how cool, calm and collected the men were. The Husband was charming and Mad Max equally un-phased. It was a triumph that could in some part be attributed to the fact that no-one in our circle of family and friends would have guessed in a million years that I would ever have had any kind of carnal dealings with the man in question.

Probably one of the most awkward encounters of my life happened on the train. I was with a friend who was visiting from overseas, and we were heading into the city for a day of sightseeing. Before I knew it, Rocky was sitting next to me.

Rocky had never been my type. He was an older guy who I had recruited as a bull for The Husband’s birthday celebrations. We’d had a pleasant enough time but he couldn’t get it up for more than a quick blow job.

And here he was, making polite conversation with me and my unknowing friend on the train. I managed to steer the conversation into safe, work-related territory. But as we neared the station, he mentioned getting together again, claiming that he’d been seeing a physiotherapist and nodding towards his crotch. It was excruciating. I put on my best poker face, said how nice that would be, and ushered my friend quickly through the station without any reference to the conversation at all.

The most personally confronting for me was the night that I came face to face with not one but two of the first fellas to knock back my advances. It had all started 6 months previously in my favourite pub, when I realised I wanted to snog the face off a mutual friend. It’s a pub that I usually go to with one or two friends, but this time we were all there, including The Husband. The mutual friend being there was no surprise, but I was still blown away by the fact that he, The Husband, and I were all stood at the bar having a completely regular conversation. The Husband even bought him a pint. And before long, everything was back to normal.

That is until Mad Max’s Brazilian bandmate walked in and started talking to me like we were long lost friends. A few months earlier, I had drunkenly flung myself at him at a party, proclaiming my newfound polyamorous status, and frightening the poor guy out of his wits.

While it started awkwardly, the night at the pub ended up being a positive and affirming experience. Being knocked back early on had been a massive blow to my fragile ego. But by that night, my confidence in myself and what I was doing had grown immeasurably. And I was looking particularly smoking hot. Where I had taken it as rejection, it was more apparent that they were scared and intimidated by such openness. Even though I was no longer interested in either of them, they were clearly interested in me. And it felt good.

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He’s Just Not That Into You

Rejection stings for anyone. Anyone with a degree of humility and empathy anyhow. But like I said, I find it particularly hard. I had a reasonably happy childhood, but intermittent bouts of therapy all come back the root cause of my birthfather leaving at an early age. No big surprises there. When I tracked him down decades later, he rejected me all over again. And my husband, the soulmate, walking out half way through our marriage didn’t help too much either.

Knowing the cause doesn’t always help resolve the problem. I have worked hard over the years to build my resilience and change my expectations of myself and other people. Putting myself out there and leaving myself open to ridicule and derision is a daily challenge – in my work life, social life, and now my sex life too. Quite often, it’s so much easier to hide away underneath the duvet in a darkened room.

You don’t need to be Sigmund Freud to work out the links between paternal abandonment and sexual promiscuity. I became sexually active and adventurous at a reasonably young age. It took me a long time, and a painful process of realisation, to understand that my behaviours didn’t always come from a positive place. While I liked to think I was empowered and in control, my exploits were linked to a desperate need for validation, acceptance and approval. And it led to some incredibly dangerous behaviours and self-destructive patterns.

What I’m aiming for here is different. I want to reclaim and rediscover my sexuality. It’s all about the self-validation and self-empowerment and I’m determined not to fall back into past negative patterns: from disrespected easy slut to self-respecting sex-positive vixen.

Awareness of my own rejection issues means that I’m sensitive about other people’s. Or maybe it’s just because I’m a nice person. I struggle with how to turn down some of my online contacts in a polite way. It’s easy when they’re rude and arrogant, or clearly don’t fit within the requested age, relationship, or geographic range – of which there are many. But if we’ve connected in some way on the message app, and then a face photo or preference doesn’t do it for me, it can be tricky.

I learn my most important let-down lesson when it first happens to me.

So far, I’ve been met with nothing but enthusiasm. And I make a point of providing enough information and photos to minimise the risk of unrealistic expectations before we meet.

He has a cute look, kind of hipster without the pretentiousness – beard, spectacles, tongue piercing and, of course, body hair. I like the cut of his jib and can easily see us out and about together. He’s recently single, and has moved into a new flat in a trendy and convenient location. His messages and pictures hit the right level of hot without being too creepy and persistent.

I was out of action and not looking for sex at time. But the hotness of the messaging meant we were both keen to meet and figure out if it was likely to translate into real life as soon as possible. I’m on the way to a work thing when we grab a quick coffee together. We greet each other with a smile and hug. He’s exactly as I’d expected and reassuringly taller.

However, this guy is clearly working his way through a whole heap of emotional shit. Within the first five minutes, he tells me about his bitter breakup and ongoing battles to see his estranged son. Now I’m used to people opening up to me quickly – I’m a good listener and easy to talk to. But the alarm bells should be ringing a little louder.

Instead, I deftly steer the conversation away to more pleasant pastures and we talk music, football and travel before it’s time for me to dash off. The conversation isn’t particularly dazzling and I’m not sure how much more effort and alcohol I’ll need to uncover his sense of humour. But the first date is always a uniquely awkward situation, and all the other practicalities and sexual interests line up enough to suggest that we’ll at least go for a drink together. We part agreeing to see each other again.

Two days later I receive one lukewarm response. And then silence.

I’m confused – my radar is usually way more accurate and I had got this one completely wrong. The abrupt change doesn’t feel good. It’s not so much the fact that he is clearly immune to my charms, it’s more the waiting, worrying and ruminating as it fizzles out into nothingness.

With hindsight, his container-load of baggage may well have played a role in him deciding not to take it any further. And I am convinced it was a lucky escape. But at the time I’m just imagining him reeling from the trauma of witnessing the true extent of my wrinkly flabbiness in real life.

Experiencing the trials of wondering makes me a take a more direct approach with my contacts. I have been guilty of hanging on to them with a view to letting them down gently. And it feels as liberating for me as I’m sure it is for them: “Thanks for the message. Not what I’m looking for right now. Good luck with your adventures x”.

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Cock Lock and Two Smoking Barrels

There’s a busy flurry of activity with the specialist site and I’m averaging one prospective date and one sexual encounter a week at this point. I’m in the intense discovery stage and expecting it to calm down to monthly encounters eventually. Right now though, I know there are a couple of weeks where I won’t be able to get up to anything, so I line up a fun-filled Friday night last fling for a while.

The Husband has invested in a cock cage. We bought the most aesthetically pleasing one we could afford – they can cost a fortune. But it’s still an hilarious and ludicrous looking contraption. It’s a complex piece of engineering involving a clear plastic cover for his cock connected to a ring around his bollocks. There’s just enough room to breathe and pee, but not enough room for him to comfortably get a full erection. And absolutely no chance of masturbation. It takes him a while to adjust and fit it properly but he’s determined and enthusiastic. It has the desired effect of restricting and emasculating him, and he loves the total loss of external sensation. It’s secured with a tiny padlock and I have the keys. I wear one on a necklace which makes a delightful tinkling sound, and I keep it on whenever I’m out with other men.

I’ve become obsessed by the thought of Rocky’s enormous cock and need to find out if it lives up to his promise. I’ve also arranged to meet a girlfriend later on for a few drinks at our favourite pub, and the workmate with the hairy chest has let me know he’ll be out tonight too. All of my real life encounters so far have brought to mind some cheesy 80s film title. The workmate is Australian, determined, and a lone wolf. So in keeping with the theme, we name him Mad Max.

I arrange to meet Rocky in a nondescript pub between my suburb and his. He’s been pretty evasive about me coming over to his and so after the requisite small talk, I ask him who he lives with. Surprise, surprise – he’s married. He tells me how his wife hasn’t been able to have sex for seven long years and is aware that he gets his kicks elsewhere. I really should have spotted it earlier but hadn’t wanted to admit it to myself. I don’t know how to take it and need time to process the information. But the spectre of the ginormous cock is hanging over me.

He gives me a lift into town and we stop off in a quietish spot to make out like teenagers. It’s hilariously awkward as he leans the passenger seat back. And I’m absolutely terrified of anyone walking past – I really would be no good at dogging or outdoor sex! He’s been talking dirty to me the whole time he’s been driving, telling me what he’s been thinking about doing to me and what The Husband is going to see. By the time we park up, I’m already turned on and we snog hungrily. I’m eager to cut to the chase and quickly undo his jeans. It truly is a handful. But it’s slightly soft and not the rock hard mighty sword I’d been imagining. I know the conditions aren’t exactly conducive, but really? Again?!

After a bit of a pash and a fondle, it’s time for me to leave and I’m not convinced that he’s the right bull for the birthday scenario.

The pub is quiet when I arrive and I’ve just ordered my drink when Mad Max walks in. It’s the first time I’ve seen him since the party. We’ve texted a couple of times and agreed to pick up where we left off at some point. It’s all pretty laid back and as more of our friends arrive, we play it completely straight and everything is as it usually is.

But when Mad Max offers to drive me home, we both know we’re going to his flat. We’re our usual chatty flirty selves as I investigate his home. Once he’s lit a couple of candles, we kiss and he starts to undress me. It’s confronting for me, I’m not comfortable with being seen naked! I trust him so I go along with it.

Or maybe I’m beginning to give fewer fucks – now that I’m getting more fucks.

We’re both relatively sober this time and he’s nowhere near as assertive and dominant as he was at the party. But it’s not unpleasant at all. And his hairiness is still incredibly sexy. We head naked to the bedroom. He eats my pussy for a while and I suck on his cock. He manages to find a condom and he fucks me slowly on my back before flipping me over and taking me from behind. I even ride his cock and am surprisingly close to orgasm. It’s fucking great. Again, it’s the utter dirtiness of the whole thing that is doing it for me.

Neither of us cum. It’s too late and we’re too tired. But we both enjoy ourselves enormously and we chat comfortably as he drives me home.

Getting home is always my favourite part of the whole episode. The Husband is waiting up, and he kisses my feet while I tell him the story before he licks me to orgasm. It’s only then that I unlock the cock lock, unleash the beast, and let him fuck me.

I have purposely stayed sober because we have special plans for the next day. We’ve put the whole day and night aside to make the most of my adventures, have filthy sex, and focus on each other. In one short evening I have got off with three different men and fucked two of them. The only downside I can see so far relates to perils of spending so much time snogging – the beard rash is outrageous!

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Top Gun

Top Gun is intelligent, independent, and while he’s rebuilding himself after a difficult breakup, is refreshingly self-aware. We enjoy hanging out together and we’re definitely in ‘friends with benefits’ territory more than just ‘fuckbuddies’. The practicalities all stack up too. His house is clean and tidy, he has a nice bed, a housemate who is conveniently out a lot, good music, and plenty of wine. While he doesn’t understand The Husband’s angle on the situation, he’s suitably respectful and appreciative of it. And most importantly, he adores me.

So each time I’ve given up on him, he’s sent me a message that makes me smile and somehow manages to reel me in again. After a reasonable degree of flattery and assurance, I agree to drive over for a couple of hours one afternoon and ‘see what happens’. Besides, I left my favourite purple G-string there.

On the drive over there, I’m anything but enthusiastic. I am really wondering what the fuck I’m doing, heading to a strange guy’s house for an afternoon hook-up. Especially when I don’t even know if I’ll even get laid. He greets me with a hug and immediately picks up on my mood, noticing that I’m more nervous than last time. I highlight the lack of adrenalin and alcohol, and the whole bizarreness of the situation. We snog in the kitchen again and quickly head to the bedroom where he hands me my missing G-string. He ‘heads south’ again eagerly. His dick is really hard and I grip it really tight. I’m waiting enthusiastically as he puts on a condom, leans over me, and pushes inside me.

We have lift off!

He holds my legs back and fucks me fast, deep and hard. The reality of having another cock inside me is as exciting as I had hoped. I’m grinning like mad and getting off on the novelty and dirtiness of it all.

However, he doesn’t have much variation of speed or technique and we eventually take a break from all the frenzied exertion. And he won’t let me get on top because of a previous scary experience where his partner had almost broken his dick off. We discard the condom and suck on each other’s bits again. I’m keen not to waste the money-shot so encourage him to cum in my mouth. I’m sitting up and he’s kneeling over me when he shoots his load. There’s gallons of it, all in my mouth, over my face and tits and in my hair.

The potentially awkward post-coital interaction is reassuringly comfortable. We lie in each other’s arms and talk some more about how this is working out and what we both enjoy about it before I head home.

I smile as I walk in the front door and The Husband looks so excited that I’m worried he’ll have an aneurism – we’re not as young as we once were. He kisses my feet while I tell him all about it. When I get to the part about the money-shot, he kisses me softly all over my spunky mouth, face and tits.

I was never expecting to cum with Top Gun. That happens when I get home, and The Husband licks my cunt clean until I orgasm so hard that I think it’s me who’ll have the aneurism.

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To Have and Have Not

This time, I arrange to meet Top Gun on my side of town, and I pick the venue carefully. It needs to be close and convenient as I have busy day. But also, I don’t want to risk bumping into anyone I know while I’m on a date.

We’re both heading towards the door of the pub from opposite directions when we spot each other, recognise each other immediately, and smile. We hug and it’s comfortable. He’s taller than me, not by much, but taller. He smells nice, clean and with a subtle hint of aftershave. He’s dressed casually in black and grey, and we look like regular mates who are meeting for a drink. All good signs.

It’s not the most ordinary of situations but the conversation flows as steadily as can be expected. I pick up on his nervousness and make a conscious effort to make him feel at ease. I’m a good listener and make people feel comfortable. I’m beginning to realise that the skills I use every day in my professional life are both transferrable and extremely helpful in the world of dating and casual sex.

I’ve only scheduled an hour and a half and the time goes quickly. We talk about hilariously unsuccessful dating stories, music and travel, and bond over our 90s raving experiences. He tells me again how gorgeous I am. And most importantly, he makes me laugh.

He has already printed out a copy of his work shifts for me to let me know when he’s available – obviously keen and with good organisational skills. As he walks me to my car, we make plans to have a drink over his side of town and ‘see what happens’. He seems nervous so I’m the one who suggests a kiss. It is tentative but promising.

It’s exciting, I can finally see this happening. The Husband describes me as purring when I get home and tell him all about it. For some reason, I feel more comfortable arranging a meeting for when The Husband is otherwise occupied. I just don’t like the idea of him anxiously waiting at home while I get off with some random guy from the internet.

The timing all lines up for the following Sunday when The Husband is at a football match. He is suitably excited and so is Top Gun. I want to be able to drink, and the arrangement involves some complex logistics, public transport and my trusty taxi app for the way home.

He meets me at the agreed bus stop, we hug, and I get into his car. Let’s just take a moment to digest that…. I get into his car. A stranger I know through a sex website, who I’ve only briefly met once before, we’re on the other side of town, I don’t know where I’m going, and I don’t even know his real name. I’ve just spent two hours planning and negotiating public transport because drinking and driving is dangerous. And yet I get into a stranger’s car without thinking twice. Who am I?

We drop the car at his house, I text the address to The Husband, and we head to the pub. It’s a cute pub and it feels like a regular date. We talk freely and by the second beer I veer into political territory. It’s what I do, I can’t help myself. I try to avoid it, aware that nothing will turn me off more quickly and severely than a reactionary, racist, sexist, homophobic wanker. It’s such a big deal for me that I’ve since incorporated it into my early contacts with people to avoid any awkward passion-killing arguments.

My instincts were right, he still seems to be a decent human being and we head back to his house. We’re hitting it off as friends and we’ve been touching hands so far, but not much indication of sexual energy. He shows me his house, pours the wine, and we snog in the kitchen. It’s lush, I love snogging, and he’s a good kisser.

We drink more wine, fondle on the sofa, talk, and drink more wine. Too much wine. By the time we get to the bedroom it’s all a bit of a blur. He gets naked and I’m wearing my favourite new purple slip and matching G-string. It’s not my usual underwear of choice, preferring big comfortable knickers to buttcrack chafing, but I recognise the appeal in this situation. We snog lots and feel each other’s bits. It’s slightly awkward and I distinctly remember shuddering at the cheeziness when he exclaimed that he was ‘heading south’ as he went down on me. It was good though. I was completely getting off on the newness and naughtiness of it all. But penises are unpredictable and contrary things, especially when mixed with wine, middle age, and first night performance anxiety. He couldn’t stay hard and he couldn’t cum.

After a break and a final fling of fellatio, we called it a day and I dashed out to my cab. After a great start, it all ended awkwardly and I went home disappointed, grumpy and determined not to bother again.