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…
18 Comments
I don’t comment often, but I feel like I should now, just to stay that you’re really a good writer. Thank you for blogging!
Thank you so much! That’s really kind of you to say, you’ve given me a skip in my step this evening =)
Your obvious gleeful-sorrow joy-horror at “MONSTER” made me laugh.
Though “years of training” sounds rather a delightful challenge. ;)
Haha well I have been chatting to my other half about this recently and I think he likes the idea of me doing some training/practice when I’m alone. Problem is I rarely ever have the time. Where would I find the time to play with butt plugs if he weren’t there to make me put my phone down?? Mystery =)
Yeah my first boyfriend wanted to try anal – he wanted to try anything. At that time in my life, i hadn’t.t seen many cocks but just knew he was not going to fit his in my arse. I was right – now I know he was pretty enormous. I used to have anal a lot but have cut back. I too love the “dirty girl” factor and watch it on porn. But who knows – maybe next week we will, i had an ex who kinda ruined it a little for me but thankfully there are lots of ways to be dirty ;-)
Great post, brilliant illustration (and tag! :)) x
Firstly I LOVE the illustration on this piece, there is just something about her that just looks so badass.
As for anal, I too am obsessed and we definitely don’t do it often enough either. Sometimes I wonder if it is just laziness or our part or if by abstaining we are actually making it all the more hotter when we do do it
Mollyx
I LOVE this one too! That horny look of determination on her face! *swoons*
x
Thanks for another great post, entertaining as always because who does not like to think about anal sex! I love it when my partner is in the mood. However your story has left me with more curiosity about how you came to see your friends penis. Clearly there is more to the story……please elaborate!
Probably not the most intriguing story, I’m afraid: I saw it because I had sex with him =)
Hi,
Thanks for the reply. You may have already written on the topic and I’ve missed it but I’d enjoy hearing more of your thoughts and feelings on sex with friends. Also how so you think penis size affects men’s personalities and inversely did finding out he had a large penis affect what and how you thought about him.
Best regards- An avid reader.
This is a fabulous post! I’m really thankyou you’ve written this. I used to have the same issue with a partner, especially the feeling like a failure, because of his size- and the last thing I wanted to do is come across all ‘woe is me, my partner’s cock is too big!’ I wondered for months if I was doing something wrong, not preparing myself adequately, or choosing the wrong position. However, I finally had to come to terms with the fact it just wasn’t going to happe (comfortably anyway).
Thanks for your insight, and honesty!
I almost want to say poor guy. A cock that big when you want to have anal is just a bummer. I’m very curious what got him on his quest. Did someone ask and then he became focused when it wasn’t successful? 🤔
I like that it’s a bit of a quest for you as well. Or something to be pursued occasionally at lease. With extra lube of course
I think he probably became more determined as a result of being unsuccessful! I know he also had a girlfriend at one point who was quite keen to try anal, so that might have added to his enthusiasm for doing it I suspect. But yeah, definitely a bummer =)
Love this post. I can fully relate to this. Although the reasons might be a little for my partner as she seems to have just gone off anal as well so she undoubtedly misses it less than me! Back in the early days though…Ahem! It is one of those things you do early on in the relationship (like golden showers or other kinky stuff) that becomes gradually more difficult when you live together. I think it might be that these things take a bit of planning (giving yourself an enema or, in the case of watersports, drinking enough water so that your pee doesn’t smell like sugar puffs) and are harder to plan when you’re both sitting on the sofa staring at your phone or the TV. And if you can plan them the element of spontaneity will be lost. Or giving yourself an enema might have seemed like a good idea but it’s actually put you off anal altogether. When you don’t live together you can whip round and do some prep and take more time but going from the couch to ‘can I fuck your ass, please’ is tricky ground to negotiate. Perhaps a subject for a future blog? How to get kinky when you’re living together whilst also avoiding the ‘light candles and play soft music’ cliches? Keep up the great work!
I just love that illustration, she’s me…determined as a terrier and unable to hide the facial expression that go with it *laughs
I get you on the lack of anal, I love it and used to do it all the time but now *tumbleweed moment* and yet I crave it so much.
I’m not sure if I’m a little more interested in anal than I was before or if I just want to watch some old Indiana Jones movies, but either way, it’s excellent. And yeah, i could see girth being an issue.
Great post! Girth could definitely be a huge issue (pun intended). I loved the intro describing your friend.