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A Girl's Guide to Screwing Older Men

What to wear when you're trying to be a little Lolita life-ruiner.
October 10, 2012, 12:30pm

Right. We're going to go ahead and assume that you're here because you want to know the joys of making love to a male member of the species who is much, much older than you. Spoiler alert: There aren't too many who are both available and particularly eligible – think plummeting libido, ailing prostates, pendulous moobs and – *shudder* – white back hair. It's cool though, availability isn't really an issue when all he can think about is getting balls-deep with you in his wife's bed and anyway, this is a judgement-free zone – if it's good enough for Frida Kahlo, Megan Stammers, Courtney Stodden and my high-school friend Bubu, it's good enough for anybody.


Plus it's important to remember at all times that those bitches ain't got nothing on you. As far as we're concerned, the only thing that stands between your heart and his dick moles is a bit of professional styling. Since you're most likely at an age where you can hardly support yourself, let alone afford to hire a stylist, we came up with this handy sartorial guide to help you rub up against that big bag of excess skin, nuclear family fall-out, 10CC records and #RealManMoney in no time. Trust us: Just like your crush's peen, we've got experience.


Clockwise from left: J.W. Anderson for Topshop V-Neck School Sweater, Sister Jane Flower Trousers, Vivienne Westwood Anglomania Lee Icon Denim Jacket, Urban Outfitters flask, Ralph by Ralph Lauren perfume, MAC Clear Lipglass, Oysho White Briefs, Vagabond Black Grace Heeled Loafers In my experience, people who want to sleep with their teacher attempt to do so by wearing strappy high heels, covering their eyelids in blue eyeshadow, and/or swearing a lot – i.e., they feel it's necessary to dress and act "like adults do". Sorry to break it to you girlfriend, but that's not at all what he wants. Every tick in the morning register reminds him of something he'll never do with his life, he already spends the whole of his lunchtime worrying about bills (you don't know what these are yet) and each crafty joint he smokes in the garage when his wife's gone to bed becomes in his mind an effigy of the menopause.

You see, teachers are essentially squishy, mushy romantics who derive satisfaction from imparting knowledge to kiddywinks. It's all pretty straighforward when you think about it; it's sort of like the urge to procreate in order to give your life meaning, except in this case sex = The Old Man and The Sea, and the baby is an essay. Oh god, that sounds dull. The point is: Take off the makeup, stop swearing all the time and allow him some space to be his pretentious self by asking loads of questions with wide eyes. Not too wide though, you don't wanna look overly innocent or you're gonna scare him away by reminding him of the fact that he is a paedo. This is the no.1 thing that you do not want to do. As such, balance is key: achieve it by pairing something floral that will accentuate your frailty with something not so floral, like a denim jacket. Or a pair of chunky loafers. Or maybe actually wear your school uniform but start getting hammered during breaks, drinking from one of those really cute patterned flasks they sell at Urban. Did anyone say hammer, cause I think we just nailed it! Whatever you do, keep the perfume musky and tomboy (you are bathed in floral as it is), the underwear white (because that's what mums AND toddlers wear), don't even think about waxing your pubic hair – and boom! You look old enough to have sex, but young enough to have no idea how to blow a penis.


Clockwise from left: Sandro Dress, Bumble & Bumble Brilliantine, Dr Martens Boots, Stoned London Necklace (99 Portobello Road), Illamasqua Lipstick in Howl, Army Surplus Beret, Cos Cable-knit Jumper, Flower by Kenzo perfume

Don't pretend you haven't thought about it. Even if you don't think he's hot, isn't there something so satisfying about the idea of messing around with your friend's dad after she borrowed your New Balance and "accidentally" took them on holiday? There are few things that are annoying enough to avenge trainers filled with sand, and one of them happens to be a quick fumble with Daddy in the linen cupboard. Or maybe your ex-boyfriend pissed you off so much that you're determined to ruin his life forever, and having sex with a family member is the most surefire way of letting him know you've withdrawn his Oyster privileges and now he's stuck forever in the friendzone. Whatever your reasons may be, getting together with this type of complex older man is all in the planning. Seduce him carefully, k? Avoid direct contact with cleavage: this will scare him off. (He has his own daughter that he's trying to protect from every brute in the world, remember? He's not going to fall for any old trick). Go for a little skirt and no tights, you're obviously kind of crazy anyway so your friend won't find it odd that you're rocking bare legs in October. Then whenever she's out of the room you can drop your iPhone down the back of the sofa and spend ages wriggling around trying to find it. Weirdly, dads also love it when you dress a bit like an aunt, so wear lots of layers and rings and maybe even some sort of hideous jaunty beret. This reminds them of the sexy, clever girl in their class at school that they were in love with for 12 years before their wife came along with longer hair and bigger breasts. Now the hair and breasts have lost their edge, and Daddy's yearning for some love that's been unrequited since before you were born. Most importantly, you need to win the trust of the man you're about to drown in a whirlpool of sexual fantasy, intense guilt and self-loathing. You need to employ tactics opposite to those you'd use on teacher – wear your hair down around your face, a matte russet lip and a really killer necklace. Lipstick is sexy, hair down is pretty and good jewellery is cool in a non-threatening way – he'll feel young again without it being creepy. Encourage him by talking about university life, smoke in the front room and ash your post-coital cigarettes into the Roy Lichtenstein mug you bought in the gift shop at the Tate. Finally, if you're lucky enough to know he smokes pot, use that as your final endeavour. Slightly stoned dads who miss being 22 are going to fall into your arms before you can even croon "tell me about O-levels". He might even secretly crymax. So cute.


Clockwise from top left: Kiehls Musk Oil, Aspinal PVC Shopper, American Apparel Skirt, Benefit Benetint, pop socks by Wolford, Rick Owens top, MYLA Bra. This one might seem cliché, but seducing your boss can be a really fun way to pass the time when you're stuck at work with no afternoon cocktails and nothing to look forward to. Sex in the stationary cupboard or the disabled toilets is not gonna work and never has, chances are your office is open plan so it's impossible and your life isn't a Jennifer Aniston film. Instead, exploit the new and exciting avenues for sexual improvisation that the internet provides – spend the entire day talk-fucking the big man on instant messenger so that his little guy spends the entire day headbutting the underside of his desk; post oblique messages on Facebook and Twitter that only he will understand; turn his balls into a meme.

Fashion-wise, although you might assume that taking the sexy secretary route is too obvious, there's really no better way of going about this than a hint of lingerie and a pencil skirt. What's the point in jeopardising your career if you don't get to emotionally blackmail somebody? And that's no fun if you're wearing a tracksuit or a summery blouse. Yawn. You're meant to be super-hot and super-crazy, so make a fucking effort. Before you get the wrong end of the stick and snap up a satin effect blazer and tie, remember that the only way to make work-wear sexy while it still being remotely appropriate, is to hint at the twisted nymphomaniac that lies beneath. Start with the skirt, it needs to be long enough to make your knees look teeny and your booty look poppin' (avoid any kind of awful ruffle detailing, or this will immediately translate into steampunk).


Up top, something pale and long-sleeved will hug your figure without being embarrassingly costume-y, like a button up shirt would be. A dark top would look better, but you can't glimpse a black bra under a black top. See where I'm going with this? After that, you've got a couple of easy decisions: fishnets are awful, but pop-socks are amazing; lipstick is overkill but lip-stain is vampy. Finally, you need a scent that's dark and musky enough to entice without giving away your gameplan to the whole office, a bag big enough to fit all of your whips and a fully-charged video camera. Job's a good 'un!


Clockwise from top left: ASOS ATHENA Ankle Boots, Topshop Black Lace Briefs, Sheer Luxe Cut-Out Pantyhose American Apparel, J.W. Anderson for Topshop Striped Cotton Dress, Utopia by Elena K. Gold Leaf Necklace, MAC Marilyn Monroe Penultimate Eye Liner, Cos Trousers, Topshop Bra, Topshop Suspenders The only reason I can think of that anyone would want to have sex with a policeman is to either avoid getting arrested or because they promised they'd elope with you back to your home country, and you are a 54-year-old Moldovan nanny named Vera. (Vera, if you are reading this, I still haven't forgiven you for slapping me when I was six, but I'm sorry Panos never turned up at the airport.) Anyway, I'm going to go with the first option and try to warn you that even though this may seem like the easiest of our cases, it is also the trickiest. If you've just been arrested, the time and space you have in which to fuck is limited: your parents are already on their way and if he's alone, he's probably on a bike. In practical terms, it also means that you're probably going to have to go out planning to break the law quite often, and not only do you have to contend with the chance that the person who picks you up will either be gay, a woman or very happily married, you also need to make sure you are breaking the law while wearing something that would sexually appeal to a policeman. Luckily, the last of those criteria… well, it ain't hard. Guys that go into law enforcement either have some sort of autistic need to keep things in order or a hard-on for chaos. Sartorially, these two boil down to the same thing: You need to be a mess so that he can straighten you out. Not that the whole "having-just-been-arrested" thing you've already got going on won't help, but looking a little dishevelled while you're getting cuffed could help nudge uniformed penises your way. Make sure to cry fast and furiously rub your face with your hands so that you achieve that irresistible "lipstick-on-the-lids" effect, and while he's not looking, cut a massive hole in your tights. When it comes to the clothing, keep the underwear mismatched and slightly swanky, and, on the off chance you are wearing something striped or of value (see prisoner, see thief), well girl, you just won a one-way ticket to the grossest sex of your life. Oh, and before you light that pilly-spliff or skip scanning that orange at Sainsbury's self-service, make sure you put on a tube skirt that you can roll up, or a shirt that you can unbutton in times of need. Practical! Never both, though: You might be a criminal, but you are still a (very young) lady. Good luck!

Follow Bertie and Elektra on Twitter: @bertiebrandes / @elektrakotsoni More on girls becoming women:

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Why Girls Should Never Have Anal Sex

All Grown Up: Sexing Up the Internet With The Daily Mail