Girl on the Net

Most of my sex fantasies include some anal fucking somewhere: pushing back against someone’s cock to slide it all the way in… being told I’m a ‘good girl’ for taking something bigger than I usually would… or just being told to lube up and brace myself. Unnngh… hot. And yet despite this I can’t remember the last time I actually had anal sex.

I used to know a guy who chased anal like Indiana Jones going after the Ark of the Covenant. He was a good friend, who I used to talk to about sex a lot, and he’d frequently sigh with envy when I’d tell him about my anal adventures.

“I just can’t,” he’d explain. “I’ve tried, and tried again, and it just never works with any of the women I’m fucking.”

“Why not?”

“Well, I think I’m just a little bit too big,” he’d tell me. They’d slather a tonne of lube onto his cock, test out myriad different positions, take it reeeeeeally slowly… you know, all the top tips. And he still couldn’t get it in. Too much girth, you see. So I’d pass on the tips that I’d picked up (‘have you tried it with her on top, sliding down, so she can control the speed and angle?’), wish him luck, and hope that one day he and his partner could find a way that worked for them.

I was rooting so hard for him to succeed, so he could experience this thing that he wanted – and I loved – so much.

Then I saw his cock.

It was a MONSTER. We’re talking almost comically huge: long as well as thick. I don’t know what it was like when flaccid, but erect you could have used it to hammer in fence posts or defend yourself against a zombie attack.

The second I saw it I realised that all my advice and sympathy had been for nought: there was no way on this earth his dick was getting inside someone’s ass unless they’d been in training for years. It had nothing to do with lube, or speed, or how gently he tried to slide it in: to take a cock this massive you’d need to work up from something small, through something medium, through something huge, eventually culminating your anal training regime with a montage of giant butt plugs, each one a fearful horror story on its own.

Maybe one day he’ll meet that person, but it wasn’t looking hopeful for him back in 2009 or so.

Anal fucking: girth and ambition

It would be easy, I think, for me to say that my current problem with anal sex is girth. I’ve been with guys in the past with whom anal was a breeze – they had slim cocks that slid neatly inside without needing much warm-up and certainly without causing my eyes to water. But my current partner is thicker. If we’re doing anal fucking we need to get into the easiest anal sex position for me, slather on enough lube to drown an elephant, and even then it’s sometimes a struggle. I whimper and wriggle and bite my lip and often end up saying ‘I just don’t think I can.’ Then I feel like a failure, and I get sad that this thing which I used to love is somehow now not possible.

But it’s not just about girth. My partner’s cock hasn’t grown bigger or thicker since we started shagging (or has it? No, no, it hasn’t. That’s not how it works). And we used to do anal fucking all the time! One of my favourite sex memories with him comes from super early in our relationship, when I was trying to show him just how filthy I would like him to be with me. I went on top, faced away from him, and slid his lubed-up cock into my ass so he could watch it sliding in and out while I rode him. I can’t remember how long it took him to come, but it was somewhere between ‘immediately’ and ‘about the length of a Countdown conundrum.’

That’s one of the things I like – liked – about anal: the filth factor, and the rarity, meant that I could pull out a quick anal fuck as a special trick when what I wanted was to see his face contort in hot surprise, and feel his cock pulse with an orgasm so quick it made me feel like a sexual goddess.

And OK, maybe once or twice I overdid it – enthusiastically taking the full length and girth of him and only realising afterwards that I should have been more careful. But those one-or-two times that ended in bleeding and soreness were worth every second of the teasing, throbbing way he used to roll me onto my stomach and pin me down with the head of his dick at the entrance to my ass. Lubed-up and ready to slide in, he’d make me whimper and beg for it, warning me that he was going to fuck me good and hard so I’d best be prepared…

Sigh. Perhaps the problem is ambition, then. Whereas before my top priority was impressing this hot guy by showing him just how much of him I could take, really hard in the ass, I’ve now ticked that goal off the list. Putting in all that work just to show him something he already knows seems unnecessary. What’s more, I think the appeal for him has worn off a little too. Too many nights spent trying and failing, or too much awareness of the fact that I’ll sometimes push myself further than I should has left him nervous to because he can’t rely on me to be self-aware enough to say ‘stop’ at the right time.

This went from ‘hot’ to ‘depressing’ quite quickly here, didn’t it? But it’s not all bad news: the fact that we rarely do anal now has some pretty decent benefits. It means that the act of brutal anal fucking gets to keep its place in my hierarchy of filth – a special thing that we only pull out of the bag when we’re both feeling particularly deviant. And it also means that – like Indy searching for the Ark of the Covenant – I can enjoy the fun of the occasional challenging quest. Find the right mood, the best position, the ideal lube, and if I manage to succeed in the challenge, I’ll get rewarded with his filthy growl of lust – “good girrrl” – as I slide back nicely onto his lubed-up cock and show that I haven’t lost the knack for anal – or the love for it – just yet.

This post is written for Kink of the Week, where this week sex writers are tackling the topic of anal. And because anal is my obsession, I couldn’t resist joining in. Click on the lips below to read other people’s entries…