Category Archives: Boys I’ve had

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First time anal sex: how not to do it

Someone found my blog the other day by searching ‘first time anal.’ It’s quite common, this ‘first time’ thing, and it comes up a lot in search. ‘My first anal’ or ‘her first facefuck’, like someone’s researching an incredibly explicit series of picture books. Anyway, the search prompted me to think about first times, and it occurred to me that while there are a few first times in my book, I’ve not actually written about ‘my first anal fuck’ before. Mainly because… well… it wasn’t particularly sexy.

The first time I had anal sex was down to 50% curiosity (me) and 50% ‘you’re on your period so how about we…?’ (him). Please forgive him for this – we were both young and silly, and he was still getting over the slight horror that came from discovering that menstrual blood sometimes has chunks in. If I met a guy these days who assumed that buttsex was the only possible option while I was bleeding, I would kick him out on his arse, but back then it was not considered weird for him to ask, and I think he was bored of me practising blow jobs.

Besides, I was very keen on the idea. I was still in the kid-in-a-sweetshop phase of sex, wanting to try every new thing I’d heard of to see if it worked for me.

It didn’t.

Just writing that seems a bit strange, because now anal is one of my favourite things. So what went wrong?

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Diary extract: Utterly exhausting love

Sometimes I wonder if I’ve learned anything since I was at school, when I used to fall madly in love with any guy who showed a vague interest, before desperately wishing I knew how to act on it.

Then I remember how it was, and that being young was difficult, stressful, and quite, quite absurd.

I haven’t arranged a guest blog for this week – sorry about that. In lieu, please enjoy this extract from my own diary, circa 1998. In it, I am trying to explain the complex emotional dynamic in my group of slightly nerdy, oh-so-romantic friends.

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Reasons to masturbate

Because you’re bored. Because you’re horny. Because you caught a glimpse of one of those pop-up ads and you can’t get the image out of your head.

Because it’s Wednesday.

Because you have a day off work, and you don’t know when the cable engineer will arrive.

Because you got a new sex toy and you want to try it out, or an old favourite to get nostalgic with.

Because someone whispered a special trick to you and you need to see if it works, and then try it again – three times – just to make sure.

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I like to watch you flirt

“I think the barista fancies me,” he explained as we wandered towards the coffee shop. “She’s quite flirty, you know?”

Yeah. I know. I know a million guys who are convinced that the barista in their regular coffee shop fancies them. They pop in of a morning, freshly showered and ready for work, and order their usual from someone who knows how to make it. That loving ritual of giving and receiving hot drink adds an extra tinge of flirtiness to an otherwise mundane transaction. A simple ‘how are you?’ can be transformed into a declaration of playful lust.

“No, she doesn’t fancy you,” I told him, twattishly. “Everyone thinks the barista is flirting with them – they teach them how to do it in barista school.”

“Yeah,” a twitch of something that looks like relief on his face. “You’re probably right.”

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My other half

I’ve always hated the phrase ‘my other half’ – it implies a lack of completeness about me. That I, on my own, am never quite full or rounded. Not quite enough.

I hate ‘him indoors,’ which implies the kind of comfortable, settled domesticity that I’ve never really felt with anyone.

I’m ambivalent about ‘boyfriend’ and ‘partner’ feels too grown up.

I panic at the thought of a ‘husband.’

‘Boy’ is becoming tired, and not a natural descriptor for someone in their 30s.

Says ‘girl’ on the net. At the age of 30.

‘Mate’ is either too pally or too like an Attenborough documentary, depending on how you interpret it.

‘Lover’ makes me cringe.

Some days he’s my guy, my dude. That dickhead. And often he’s a twat.

But maybe my obsession with the lack of a proper word belies what the actual problem is with any of these statements: the ‘my’ that comes at the front of them.

No one is ever mine, of course.

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