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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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Flash Gordon

He is rich, arrogant, sexually confident, and very experienced on the swinging scene. We name him Flash Gordon.

It’s his way with words that first catches my eye. We message each other sporadically over a couple of weeks. I’m not sure if I’m particularly attracted to him and not even sure our preferences are compatible. But timing comes into it again – he’s single, articulate and forthcoming during a period where I’m being bombarded with unsolicited dick pics and irritating demands for immediate hook ups.

His adventures sound interesting, if somewhat embellished. I’m particularly drawn to his accounts of parties and group scenarios. But when he describes his current penchant for prostrate play and an increasing bi-curiousness, I realise I’m not ready to go down that particular avenue again just yet. I don’t want to get his hopes up, so make a point of clarifying my one-on-one exploration focus at the moment. And that I’m not in the least bit interested in his bumhole.

He remains enthusiastic and a quick drink goes much better than I had expected. Where the sex with Top Gun is relaxed, friendly, and ‘nice’, Flash Gordon may well be able to deliver on the nasty, sweaty, grunty elements that I’m equally interested in exploring. And I like his party stories too. When we meet for dinner the following week, he’s a bit more relaxed and dressed casually in a T-shirt and jeans, with good quality trainers that befit a 50-something year old man. I’m a sucker for nice trainers.

He’s still pretty arrogant though, and talks about himself incessantly. Rubbish listening skills and an apparent lack of interest in my life is rapidly becoming a common theme with these guys. I tackle them on it by offering to answer any questions they might have. While I don’t want them to know my address, the names of my children, or the specifics of my work, I figure a mutual interest in each other is essential for achieving the ‘friends’ status that makes the ‘benefits’ arrangement work. But there appears to be heaps of confusion about boundaries and what they figure they’re allowed to know about me. They all express the same concerns: not wanting to appear impolite while also wanting to insert their penis in me – maybe the age of chivalry is not dead after all.

Amongst his tales of expensive cars, property portfolios and world travel, I pick up on his undercurrent of nervousness. For me, sexual adventurousness in middle age is fraught with concerns about physical decay and uncontrollable bodily secretions. But it also has its liberating features. With advanced years comes greater insight into the human condition, particularly the realisation that everyone is as anxious and fucked up as each other.

By the end of dinner, and my second glass of wine, we’re both more relaxed and he asks me more about my sexual preferences, experiences and ambitions. We’re sitting closely, talking dirty, and he touches my hair. The nape of my neck is intensely erogenous, and I find hair touching incredibly erotic. When he asks me if I’m up for some light hair-pulling, it has the desired effect.

I’m also impressed by his gentlemanly manners as he holds the door open for me to get into his flashy car for him to drive me home. We even share a few laughs on the way. As we get near my suburb, he asks me about my orgasms and we clarify the need to avoid expectations. He reaches over and touches my breast as he drives along. And when we pull up near my street he leans in and we have a very promising snog. It’s not until I’ve got my hands down his pants that I remember him expressing a penchant for exhibitionism. Even though outdoors sex isn’t really my scene and I’m worryingly close to home, his tone is confident, persuasive and incredibly hot when he tells me to take out his hard cock for closer inspection.

I’m shocked at my compliance, and stop as soon as I’ve grabbed a quick feel. As I adjust my breasts and extricate myself from his car, I realise I’m looking forward to our next encounter.

But the stars aren’t aligning for this one. First I have to cancel, then he does. When we’re finally scheduled to meet, I text to confirm the night before. It had completely skipped his mind. Anything less than complete excitement and adoration doesn’t cut it for me – he misses out.

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All Quiet on the Western Front

I’m taking two weeks out. I’m unwell and not feeling in the least bit sexy.

It’s been a busy, exciting and adrenalin-fuelled few weeks so it’s a good opportunity to rest and recuperate. It gives me a chance to reflect, consolidate what I’ve learned so far, and work out if I want to continue, and what I want to do next.

That’s when I start writing it all down.

My focus on personality and connection means I’ve invested a lot of time and energy into building the right ‘relationships’, fine-tuning the dynamic and working out the practicalities. And then there’s my focus on The Husband too.

So far, the effects on our marriage are even better than either of us could have hoped for. The prospect of me looking outside our relationship has made us face up to our problems, talk through our baggage, and consider how we can look after each other’s needs. Even if we had decided to stay monogamous, it’s forced us to have those conversations, and ultimately helped us to reconnect. And of course, there’s the sex. I’ve been complaining for years about not getting enough, and now we’re fucking twice before breakfast and barely leaving the bedroom on weekends.

It’s also given me a fun new interest, reinvigorated my social life and dragged me out of a rut, providing me with whole new opportunities for discovery.

Identifying and building the friendship with the right people is worth the extra effort. But it’s time-consuming. And it can be frustrating and demoralising, especially considering the fruits of my labour so far: one knockback, a few fumbles, and a grand total of two mildly satisfying episodes of actual penetrative sex.

I’m just relieved that I have a partner and am doing it as a hobby. I can’t begin to imagine how hideous the process would be if I were a 40-something single woman with a ticking body clock, desperate for a baby, and trying to find someone even vaguely suitable as husband and father material.

Although I’m not up for meeting anyone right now, I miss the Tamagotchi effect and realise that I’m addicted to the search, flirting and anticipation. Bored, I add my profile to a different dating site, one known for people explicitly looking for affairs and casual sex. It provides a whole new phase of distraction. Within minutes, I’m bombarded with messages and winks, so many that it takes me a few days to sift through, reply, and manage the new conversations on the message app.

The responses range from people interested in discrete daytime liaisons and specific BDSM scenarios to hooking up there and then for a quick shag, dirty messaging or camera sex. And then there’s my favourites, the single, independent ones who want a sexual relationship without the complications of an actual relationship.

The site is notorious for infidelity and I soon realise the need to clarify and expand on my preferences. I respond to one guy’s message explaining that I’m not interested in cheating husbands. He berates me with a tirade of abuse, accusing me of double standards and of posting a false profile. Clearly, the fact that I am happily married and have the freedom to play honestly and openly is beyond the comprehension of many.

The ones who pique my interest are invited to the message app. There’s also confusion when I ask for face photos. Instead, I’m bombarded with pics of dicks of all shapes, sizes and hues. I think it’s pretty straightforward that you need to get an idea of what someone looks like to know if you might fancy them. But apparently not.

Once I’ve connected with them, I cut to the chase and give them the full lowdown:

“Looking for a regular FWB arrangement with someone I get on with. Someone with their own place because mine is always busy. My turn-offs are sexist, racist, homophobic attitudes. My turn-ons are someone who makes me feel adored, dirty, & can make me laugh. I’m a strong independent woman in my everyday life so I like someone who can take control of me (not in any spanky kind of way, just confident & strong). Basically I want to go out, drink wine, have fun, have filthy pornstar sex, then go home feeling ravaged, tell my husband about it and start all over again”.

If they’ve indicated an interest in couples or kinkiness that’s caught my eye, then I also add The Husband dynamic:

“Involving my husband is also an option. He’s into the whole cuckold fetish, likes to be made to watch, allowed to help & clean up etc. I just like the 2 cocks at once possibilities. We work out a way to compromise”.

I’m developing more of an idea of what I’m looking for and how to express it. Clarifying early on works well – they’re either scared off or utterly into it.

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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.

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Sliding Doors

My first new friend used to be a pilot. He’s also short and charming. We name him Top Gun.

Chatting to multiple people online is time consuming and becomes a fabulously effective form of procrastination to avoid the other things I should really be doing. Each conversation has its own nuances and I have let it become too complex. I feel like I have a set of those Tamagotchi digital pet toys that I have to remember to feed and respond to.

His contact came when I was particularly busy with life and my patience was waning. It was a combination of convenient timing, his straightforwardness, and easy communication that led me to meet him quickly.

There is no fannying around with him. He sent me a naked body shot straight away, and there was nothing scary or irregular. His face pic is friendly, smiley and outdoorsy. He is also suitably enthusiastic about my photos and tells me I’m gorgeous. Being made to feel adored is a must. But it’s a difficult balance to achieve, being able to flatter sincerely without sounding creepy and stalky. He seemed pleasant enough, was going to be around when I finished work the next day. Job done.

It’s been a long day, it’s raining, and I’m grumpy and tired. I’ve also agreed to meet in a business district wine bar for some reason, not my usual habitat at all. I like to arrive early and pick my vantage spot myself, so that I’m not looking aimlessly around the room trying to recognise my date. I order a glass of wine, choose my seat and immerse myself in my phone. The place is relatively empty as it reaches our meeting time, there’s only one single guy there. It doesn’t look like him but I send a message just in case. There’s no response and no guy. I wait for exactly ten minutes, then walk out and head home.

Being dicked about comes with this territory. It’s no surprise to me. But I’m still cross, disappointed and deflated. The Husband comes to pick me up and all is right with the world once more.

I ignore the first two apologies. Apparently he was stuck in traffic and had left his phone at home. He’d missed me by five minutes. He made the point that there was still wine in my glass that backed up his story. Against my best judgement, and amidst plenty of jokes about route planning and map co-ordinates, I agreed to meet him the following week.

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House Party

I have a friend through work who I bump into every few months. He’s absolutely not my type – short and wiry, with long hair thinning on top. But we always get along well, talk music, laugh lots and flirt outrageously. He has fallen into unrequited love with an Amazonian goddess of a woman and is completely smitten, and we’ve been hanging out a bit more lately.

His penchant for the BDSM scene means he is knowledgeable and non-judgemental about unconventional sexual relationships and he’s aware that I’m interested in exploring polyamory. Most importantly, he knows that I am interested in his 40 year old, Brazilian, recently divorced, musician friend who I had briefly met once before.

When the Amazonian goddess throws a house party, it provides an ideal opportunity for exploration. The Husband and I already have another thing to go to that night and where we would usually be drinking, dancing and having fun with our mates, we are completely distracted by the idea of me going off to a party to potentially get off with a guy I’ve had my eye on. I make my excuses to head off earlier than I normally would. The Husband is shaking with the excitement and incredibly affectionate as he puts me in the cab with words of encouragement.

When I arrive at the party, it’s pretty empty and the few people there are already stoned and caning the tequila shots. I’m met with enthusiasm and the Brazilian dude kisses my hand and sings me a song with his guitar. I am way too sober and quickly drink way too much wine. So much wine that I end up scaring the poor guy out of his wits. When he asks if I’m single, I tell him in no uncertain terms that I’m married, have an arrangement with my husband, and am interested in pursuing things with him further. I act like a sex-crazed madwoman and I’m mortified the next morning. My approach is clearly way too forthright for him and he consequently passes out asleep.

I sit on the sofa with my workmate and share my woes. Somehow he ends up giving me a foot massage. Anyone who’s seen Pulp Fiction knows where this is heading. He kneels between my legs, grabs my thighs and pulls me towards him for a kiss. It completely takes me by surprise and I’m blown away by his confidence, moves and technique.

I had honestly never fancied him and there I am, getting off with him. We head off to one of the other rooms for privacy. He takes off his top and I’m stunned. He’s a drummer with an impressive six pack, and he’s covered in a thick layer of hair all over his torso and arms. I feel compelled to run my toes across his stomach as he stands over me. It’s an incredibly erotic sight, an image that has stayed with me.

His cock is rock hard, straining out of the top of his jeans, and I can’t help but take it in my mouth. We kiss roughly and he eagerly eats my pussy. He gropes and sucks on my tits, it makes a delightful change as The Husband hardly notices them at all. My gentle and unassuming friend turns out to be strong, assertive and even bitey. It’s all really hot. But it’s also weird and unexpected. And we’re both really drunk and in someone else’s house. I’m not ready for this to be my first extra-marital fuck of the new era, so we stop.

It’s late when I get home and The Husband looks crestfallen when I tell him that nothing happened with the Brazilian. I get into bed and tell him the rest of the story. The big reveal is incredibly effective and he’s massively turned on. But I’m way too tired from my exertions and quickly fall asleep, prolonging his torment till the morning.