Although I’ve been reassured over and over again by the internet and various male friends, I can’t help but feel there’s something a bit odd about thinking of someone you know when you masturbate. Obviously there are scales of strangeness: thinking of your parents is very very wrong, thinking of your boss is debatable, and your boyfriend is probably quite reasonable. However for years I just couldn’t do it. Whenever I shut my eyes and tried to imagine someone I knew getting filthy with me, in a variety of athletic positions, I got coy, and felt embarrassed about the whole thing. Maybe it was because as a kid my mum told me your ear would ring if people were thinking or talking about you, and the last thing I wanted to do was wake someone up at 1am because I was trying to involve them in a sexy version of Eyes Wide Shut.
No matter how hot I found someone or how fun a time we’d spent together it was just impossible to imagine doing anything further than holding hands. I could say the words out loud, feel the feeling of wanting someone horribly bad, maybe even relive a fumble while daydreaming on the bus, but making up new situations was behind a brick wall I couldn’t scale. That isn’t to say I was wanking over disembodied robots or just shutting my eyes and giving it a rub with nothing in my head at all. In fact it was the complete opposite. My fantasies were full of people, characters I held over from scenario to scenario, with names and back stories, and specific personality traits who just waited to be called into service as the guy who held the bullwhip, or the one who wore a nice suit and took me to dinners in fancy restaurants where they turned out the lights and… well, I’m sure you can guess the gist of that one.
Then recently I got bored of making up elaborate scenarios with interchangeable players. So in the interests of keeping it fresh I threw in someone I was crushing on and it was surprisingly enjoyable. Then I assembled a cast of people I knew and fancied, mixed with celebrities who seemed kind of dishy, and it was great! It was I imagine even better than fucking half of those people because they didn’t complain and were totally ameanable to all my wishes. “Put this here? Why of course! I’ve always wanted to!” That sort of thing.
It does, as I figured it would, feel kind of odd seeing people who you’ve wanked about sometimes. It’s a bit like when you’re in crush with someone and you daydream about your whole life together and then when you see them you feel this super deep connection and they don’t. But less deep, obviously. I’m still hazy about the ‘telling them’ thing, because if you’re not dating them it could seem invasive and creepy, and if you are it just seems desperate and lame. Like “Hey, I’m crazy and wild and when I think about you I touch myself…” WINK. WINK. SUGGESTIVE LIP LICK. WINK. It’s not like you can ask someone else if they’ve been thinking about you either. Really if you’re seeing them on the regular they should just say yes to shut you up, but when in the past I have asked (of course I’ve asked, I’m vain ok?), I’ve found the answer is generally no. One time the answer was “Only when you’re with your best friend” which wasn’t half as flattering as I think he meant it.
The best course of action seems to be think about people, put them in any goddamn position you want, but keep schtum unless asked so as not to seem like some kind of greasy Austin Powers wannabe or a sex offender. So er, if you’re reading this (Hi!) and you think that I might be thinking about you if that’s something that you think might happen then well, er, cough, well, you’ll just have to ask, if you want to know. If you don’t think that’s likely to be happening, then, well, don’t ask because then it’ll get all awkward and surely you don’t want that? I’ll just shut up now.
Pictures from Playboy by Russ Meyer (Yvette Vickers aka Miss July 1959) and an illustration from a 40s issue of Esquire via Vintage Gal’s Tumblr



















