I’m sitting here writing this with a butt plug up my arse; let me explain: I recently decided that I am at an age (26) where I should probably start to expand my anal repertoire and, therefore, quite literally, expand my anus.

I’ve never really done the anal sex toy thing; my history in that area probably just extends to a bit of experimentation as a young teen, like every pubescent boy, starting off with a felt tip and progressing to whatever root vegetable had a roughly phallic shape. Since then, the only butt tool I have owned was during my college years and was really a womans’ vibrator, bright pink and mail ordered. I never really used it and, in fact, it eventually went missing – I had my suspects!

So, apart from that, anything that’s been up there has been attached to a guy – some good looking, some not so good looking, but always a fully working, fully human cock.

Lately, however, I don’t know if it’s due to maturing (certainly in gay years) or familiarity breeding discontent, but I’ve started to enjoy harder gay porn – you know: bit of leather, boots, grunting, and guys in slings getting well and truly fisted. I’ve also started to fancy different types of guys too: older, built, shaved head and, shock horror, a few hairs on their chest. It is through watching all this more extreme porn that I got the urge to one day, maybe, be some macho guy’s glove puppet and I, therefore, decided to make a first step into a whole new hole universe and headed off to the local gay adult store to buy my first butt plug.

So, there I was, perusing the shelves in the backroom of the store (why is there always some trampy looking guy in an oversized coat, greasy hair and specs in these places carrying old shopping bags, and looking through the mags?). I was taken aback by the choice on offer: slim ones, traffic cone sized ones, black ones, silicone ones, jelly ones, vibrating ones, dual ones, triangular ones, ribbed ones, and ones that do all sorts of things to your prostate. I had already done my research on the Net and read all the safety tips (apparently it’s a bit of a myth about larger things leaving you slack and needing arse tampons in old age), and advice for beginners and I decided to start off with a medium thickness one, about 5.5 inches long and a good sturdy base – I wanted to be able to feel it, but not be too ambitious. I settled on a cheeky little latex number with a curved taper, out to about 15 inches circumference at its widest point – it looked okay to handle and certainly not wince inducing like some of the bigger ones; it even had a name: Jason – I once went out with a guy called Jason and he was an arsehole, so I’ll be renaming it. I was a bit confused by the picture of a porn model on the box – surely this shape wasn’t modelled on him? I hope so for his sake!

I was like a kid in a toy store, desperate to get my new plaything home and unbox it, but I still had to get out of the store and, wouldn’t you know it, there was nobody serving in this backroom and I had to bear the embarrassment of walking up to the main checkout in the regular, family(ish)-friendly part of the store and hand over my butt plug, attempting the casual expression of someone purchasing a CD. I thought being sized up and down by the bear serving me was as bad as it would get until he shouted out to his colleague “how much are the latex butt plugs?” The response came “Which size?” to which the bear replied “the medium one.”

After a detour to the chemist to bulk buy lube, I was home and ready to see if everything I had read about the amazing sensation and heightened pleasure of wanking with a butt plug inserted, of the satisfaction of being well and truly filled, and of the massaging of all those sensitive nerve endings was true. I took a shower, made sure everybody was out, locked my door and removed Jason from his box – I was surprised by how heavy he was. I laid back naked on my bed, rubbed my cock until it was hard, and started to lube up; one finger for a while, and then two. When the two fingers were easily sliding in and out I decided I was ready for Jason. I tried to relax fully and lubed him up; then slowly started to push him inside me, all the time relaxing and trying to open up, but he didn’t get very far before it felt uncomfortable and Jason had to come up for air. I tried again, and then again, and applied some more lube before trying yet again, but it seemed my arse has an aversion to Jason, just like I do, so I gave up and had a wank.

Now, I’m not one to give up easily and I woke up this morning determined not to be beaten by this latex devil – I might have been shafted by an arsehole called Jason once before, but this time my arsehole was going to get shafted by Jason! So I followed the same routine as before, but this time opened myself up even wider with my fingers, using three this time and lubing myself to the point where I could slide them up, barely touching the sides; I was ready for Jason. It still took a couple of attempts at inserting him, but on the third I gave a slow, determined push, and then whoosh! Suddenly the whole of him was sucked up there and my ringpiece closed around the narrow end, with just the base sticking out, and WOW! It felt fantastic, wasn’t quite the orgasm of excited nerve endings I had read about, but it felt good having something that shape inside me, filling me up nicely and well and truly wedged too (I had wondered about it dropping out once it was up there, with all the lube, but there’s no chance of that) which brings me up to the point of writing this post, sat in my chair with Jason happily lodged where the sun don’t shine – I have heard about people keeping one in all day while they go about their usual business, but I can’t imagine doing that; I’m just happy to leave him in for the moment, occasionally stroking my cock, building up to a fantastic wank, and learning to love the Jason!

It just leaves one question: where do I go from here?…