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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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