Oh modern day sugaring. The places you go…the people you’ll meet! It’s like a box of chocolates…you never know what you’re going to get. Here’s the general gist of typical first dates.
The ‘Let’s meet for a coffee to see if we connect.’
There’s something that feels sort of inherently wrong about meeting a daddy for the first time in broad daylight. And with absolutely zero alcohol in the mix.
You head to the Chelsea coffee shop in your smart casual fit and barely there makeup look and as you walk in you try as subtly as you possibly can to figure out which suited, booted, slightly overweighted silver fox is yours. Ah, there he is perched in the corner.
He looks up from the news app he’s pretending to read and gives you a beaming grin. You order an espresso to look chic and try not to focus too hard on his nostril hairs peaking out of his nose, so stark in the light of day!
Together you stumble through conversation, he’s new to all of this, you pretend that you are too. He tentatively asks what sort of ‘arrangement’ you’re looking for, and you go for the ole mutually beneficial, genuine connection, someone I can go to art galleries with (!) bullshit and he nods enthusiastically.
In a quieter tone, he explains that ‘physical intimacy’ isn’t the most important part of this for him; in the same breath he explains that he’s booking a hotel for your next meet. You smile and nod and try to look cute. It’s tough to be sexy when to your right there’s a family of five listening to every word and and to your left there’s an elderly lady listening to every word.
As you leave the cafe together, you pretend to be going in the opposite direction to him so that you don’t have to engage in the awkward rounding off conversation about your plans for the rest of day or worse, the weather forecast.
The ‘Let’s have dinner and see what happens..’
We all know what ‘see what happens..’ means. Possibly the roughest sex you’ve ever had in your entire life. This is always a fun one because of the tension that slowly builds over dinner. And the setup of sex being a possibility but not a guarantee.
It’s all up in the air. You’re obvs wearing a sleek LBD and your lips are just ever so slightly stained. As you head inside the lights are dimmed and you’re already getting turned on.
He’s in the bar area relaxed into his seat with his martini trying to look like James Bond or something. It half works to be fair. You order an elegant cocktail and definitely not a pornstar and try to look mysterious and a little bit sinister.
You feign interest in the menu but you know he’s probably going to order for you both because he’s an entitled little control freak. Oh well, it’s kind of hot.
The waitress knows what’s up, plus everybody else in the restaurant but who cares because it’s London and it’s night time and they’ve seen it all before. You take itty bitty bites of your food like a fucking mouse and every time you look up from your plate you give bedroom eyes like never before.
He’s in business, but he’s careful not to say too much, incase you use the information to blackmail him and ruin his entire life. Once you’re both pleasantly drunk and way over the small talk stage, he puts his hand on your leg and in five minutes you’re Ubering back to his.
The No Frills
He’s ‘very busy’ and values his discretion so there’s no time to be meeting for silly little lunches. He’s booked a hotel for 2pm. It’s never anything nicer than a Hilton or Malmaison and at worse you’re in for a Travelodge. He arrives before you and stows his wedding ring in the bedside table draw.
He takes the wine out of the minibar and pours himself a glass. You receive his text telling you the room number. You storm past reception avoiding their eye like the plague and slip into the lift. He opens the door for you with a smile and kisses you on the cheek.
He’s switched the TV on to a music channel and you try very hard not to cringe. You perch on the edge of the bed wondering whether to remove your shoes as he pours you a glass of wine. He draws the curtains hiding the view that looks out onto the car park. God this is depressing, you think to yourself. You actually feel quite sorry for the guy, let alone yourself.
As you’re about two sips into your wine, he comes and perches next to you placing an awkward hand on your leg. He asks if he can kiss you and you lean in. He gently pushes you back onto the bed and removes your shoes.
You reach for one more sip of wine. He’s very horny. After about three thrusts he comes with a little whimper. Well that was easy, you think to yourself. Together you cuddle and talk about nothing in particular in the soulless hotel room. It’s kind of nice- in a weird, lonely way.
He pops an envelope of cash on the table and makes a point of ‘not wanting it to feel transactional’. Once he leaves, you turn the music up and dance in the mirror, take a shower and eat some shit from the minibar before getting the hell out of there.
The Booty Call
It’s kind of a spontaneous affair. It’s a Saturday night and you have no plans. You’ve been messaging back and forth and you’re kind of feeling it. ‘Come over to my place’, he says. You hurriedly get ready and drink a white claw, before jumping into the Uber he’s ordered for you.
You ask the driver if you can connect your music, you need to get pumped for this. As the car pulls up to a secluded apartment, you wonder if you’ve finally pushed it too far and tonight is the night that you will finally be ferociously murdered. As he opens the door and lets you in, you joke about this to him.
He doesn’t laugh. He’s kind of young for a daddy. As he heads to his extensive alcohol supply to make you a drink, you stand in the stark white lighting and look at the one and only piece of art on the wall: a hipster print of portobello road. You wonder how somebody who supposedly has so much money can have so little taste.
He comes back with your drink and you notice his bare feet and awful toes. You force yourself not to get the ick. You sit on his sofa together and talk about your sugarbaby experience. He’s actually pretty fit. 15 minutes in and you’re all over each other. You push him off to go to the bathroom where you realise you’re way drunker than you thought.
You laugh with yourself in the mirror at your crazy idiotic life and send your friend your location just incase. Before you know it he’s fucking you from behind as the framed photo of his son on his bedside table stares you straight in the eye. Nice.
The Walk in the Park
Oh yeah, the Covid19 special. Not as common anymore but during lockdowns this was the go to first date.
You exchange a few banterous texts about these unprecedented times (har har) and agree to a friendly walk around Hyde Park. He’s waiting for you at the gate wearing a Barbour jacket and a cashmere scarf.
You’ve forgotten how to dress yourself so you’re wearing some bizarre getup but he’s a gent so he doesn’t say anything. You stroll along and pretend that he isn’t the first person you’ve seen for two weeks and that you haven’t forgotten how to interact with another human being. It’s all quite wholesome. At one point, his hand brushes yours and you almost orgasm at the touch of another living soul.
You converse in subtle competition over who is more Covid conscious before agreeing to meet next week and fuck the living daylights out of one another.
Iso
Iso is a writer and filmmaker based in East London. She is passionate about all things erotic and leads a sexy, shame-free life in hope that she can inspire others to do the same. Originally from a Northern seaside town, she is naturally drawn to the best things in life: candyfloss, trashy karaoke bars and heart-shaped sunglasses.
