I Lost My Anal Virginity With A Male Sex Toy And This Is What Happened

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Warning: This article is about my anus. What you won’t learn about me during this article really isn’t worth knowing, but I feel as though it’s my duty to point out that if you have a prudish disposition, it’s probably best to turn away now. By saying this, nobody can say: ‘you could have at least warned me.’

I’d like to preface this article by pointing out that I went to a respectable university and achieved a respectable masters degree in journalism. At no point during that time did I ever think I’d be shoving things up my arse for a ‘story’, yet here I am doing precisely that.

But hey, like my experiences with this sex toy, life doesn’t always go as smoothly as you expect.

It’s all my fault, in my desire to deliver stellar public service journalism, I suggested the idea of doing a sex toy review and the whole thing snowballed.

I reached out to UberKinky, an online adult retailer who have every item for every sexual need, and they sent over the ‘O-Boy’ for me to play about with.

So let’s not beat around the bush – you’re all here for one reason, and one reason only – the story of how I lost my anal virginity.

My parents will be so proud…

For weeks I knew the time would come when I had to test this earth-shattering piece of kit out, which would in all likeliness turn my world upside down and inside out. I’ll be honest, it led to many a restless night; sometimes, when the daunting prospect of using it kept me up at night, I swear I could hear it faintly whispering my name from the wardrobe I’d imprisoned it in, patiently biding its time for the right moment to strike like some sort of pervert Grim Reaper.

I waited and waited and waited for the right moment to use it, mainly because I needed to build my confidence up, but also because I wanted to make sure everyone was out of the flat. The last thing I wanted was for someone to accidentally come into my room whilst I was sat there trying to squeeze the equivalent of a Cumberland sausage through a keyhole.

Eventually, a day came when I had the flat to myself, so I locked the front door, shut the curtains, cleaned my bum, and took the plunge into the art of self-prostate massaging. A few, brave girls had been in and around that area before, but this was a different kettle of fish all together. Those rare occasions were merely test runs – today was my Apollo 11 mission.

I opened the packaging with obvious trepidation; the last person to open a box this dangerous was Pandora, and look how that turned out.

In truth, the toy wasn’t much to look at, looking more like a rubber door handle in some sort of warped, carnival fun house than anything meant for sexual stimulation. I was careful not to underestimate its power though – complacency and naivety would be my biggest downfall – and I was wary that this was something that could (literally) come back to fuck me in the arse. No, like Mother Nature has taught us with the black widow spider, size and lethalness have no direct correlation, so this little contraption would be afforded my utmost respect.

Even though I glossed over them, the instructions made it explicitly clear that the toy wasn’t for the faint-hearted, and strongly advised users to apply copious amounts of lube, especially for first timers. This was no time to play the hero – I’m not being paid enough for that – so I proceeded to lube that motherfucker up for as smooth a first insertion as humanly possible.

I moved over to my sex pit, climbed onto my back, and cocked my legs in the air like a pregnant woman buckled into a pair of stirrups. I briefly pondered whether this was the most vulnerable position I’d ever been in, but this was far too pivotal a moment to contemplate such a thought.

In an attempt to get my sexual juices flowing, I decided to put some porn on, but in all honesty, it may as well have been Wanted Down Under for all the attention I was paying to it. There was only one ‘down under’ this dildo was concerned with: my down under, and it was not to be denied a date with destiny.

I began to bring the slimy toy towards my innocent little anus, inching closer and closer by the second until – at last -the first contact. Entry was not to be permitted that easily, however, with my rear end reluctant to relinquish a space it had inhabited for close to 25 years.

In a way I’m proud of my arse for not going down without a fight, I’d have been more worried if it had gone straight up without any resistance. It was tougher than I’d expected though, which is when I realised why lube was such an important ally in my quest for anal stimulation.

After a short while, I begin to have some success, wearing down my butt hole to the point where I could initiate the penetration phase. After minutes of wiggling the toy around and waiting for an opening, the tip of the dildo made its move, forcing its way in. This innocuous bit of rubber had already navigated previously unchartered waters; this must have been what Christopher Columbus or Neil Armstrong felt like when they ventured to places no man had ever gone before.

There was no time to ponder my place in human history though, adulation would come afterwards. For now, I still had work to do.

With a deep inhale, I thrust the toy further into myself, ignoring every fibre of my being screaming at me to stop. My arse, however, seemed to be embracing it. There was little to no resistance at all now, and in fact, it actually clenched around the toy like a baby joey holding onto its mother.

The sensation was undoubtedly a foreign one; uncomfortable at first, yes, but neither painful nor intolerable. In all honesty, it felt like I hadn’t finished a poo, but these were just dildo mind tricks I’d be warned about beforehand.

By now it was about half way in, and after several minutes spent refocusing and strategizing my plan of attack, I realised that I had no choice but to go in further. Quitting was not an option; stopping now would be like attempting an Everest expedition and bottling it at the base.

With one final push, it was fully inside, and like an aeroplane breaking through cloud cover, there was a brief tranquillity where nothing else mattered in the world apart from me, and this thing up my bum.

Sadly, this ecstasy lasted for about five seconds before I hit the roof. If the dildo was an aeroplane, I was experiencing severe turbulence.

It’s not like it was excruciatingly painful, it just felt weird. It’s hard to put it into words, but it felt like I was giving birth the wrong way around, and I felt nauseous from having something that big inside me. It was kind of like having a massive wasp on you; it doesn’t cause you any real discomfort, you just can’t settle or get rid of it quick enough, and you end up jumping around like a march hare until it’s gone.

I felt every single inch of it, and when I say every inch, I mean every inch. Alarm bells were ringing around my body telling me I was under attack from an unidentified object, so I instantly yanked it out, which incidentally, was a lot more uncomfortable than putting it up. Then again, I suppose mountaineers always say that the descent is more dangerous than the ascent, so I guess it’s a similar premise.

A red hot sensation came over me, like the feeling you get when you have a dodgy curry and suffer from explosive diarrhoea an hour or so after. When I was free of this little invader – for a minute – I actually thought I’d become incontinent and my dinner was leaking out of me like a gushing, chocolate waterfall. Fortunately, my mind – and my anus – were just playing tricks on me again.

I took several deep breaths, and reminded myself that I was doing this for you, the people. Many lesser men would have folded under the weight of expectation, but in a totally sadistic way, I was anxious to try it again.

I squirted the rest of the lube onto the toy so that it was so greased up I could almost see my bewildered reflection staring back at me in it. I prepared for take-off once again.

This time, I suffered none of the mishaps of the first effort: there was no struggle, no pain, just, bliss. I think the test run had been a shock to my system, but now my body had become acclimatised to the toy, the real fun could commence. Where I ended and the toy began became irrelevant; we had become one and the same, that black dildo the yin to my yang. It was a beautiful moment, as two opposite but equally balanced forces came together to create a perfect state of equilibrium.

Ahh, euphoria, you elusive and ethereal thing, you.

At this point, I was feeling adventurous (putting things up your bum will do that to a man) so I decided to put this little pleasure giver through its paces.

On the top of the handle was a small black button that I was growing more and more curious about. I hadn’t read the instructions properly so this next sequence was an unmistakably glorious, and welcome, surprise.

I pushed my thumb against it with the same recklessness that got me into this situation in the first place…

Exaltation, elation, jubilation: all synonyms for intense pleasure, but all considerably inadequate words to describe how good that button made me feel.

The first press resulted in a short, sharp burst of intense vibrations which were suddenly being omitted from this magical little toy. Oh, good lord, the vibrations. The rhythmic repetition sent me into a state of hypnosis, my body at the behest of this tiny little device.

My whole body was pulsating to the constant throb of the best sexual partner I’d ever been with. As my prostate was being gently massaged, the uncomfortableness I’d initially felt slowly subsided and was replaced by a level of satisfaction I’d never felt before.

I was completely entranced in some sort of pleasure paralysis, fixated on the toy’s hum like the ancient sailors enchanted by the mellifluous songs of the mythical sirens.

If I’d have died in that moment, I’d have died a happy man.

I began to hit the button several more times, experimenting with the various settings: slow, intermittent, fast. Slow was not going to cut it, only more vigorous paces would take me to where I needed to be.

At this point, the toy had almost disappeared completely, taking refuge in my anus for the foreseeable future. I was more than ok with it. It was almost piercing a lung – but I was past the point of no return – for all I cared it could stay there forever if it wanted to.

I began to try different positions, gyrating around my bed like some sort of possessed break dancer. After several failed position changes, I realised that back is best and returned to where I had started.

While all of this was going on, I was simultaneously masturbating, figuring that if I was going to have this experience I was going to do it properly. I managed to direct my attention to the porn that had been playing this whole time, and after about ten minutes of being overwhelmed with rapture, I was on the verge of something both familiar and unfamiliar.

It was the feeling of climax, but not in my penis like I’d experienced so many times before, but in my bum. I could feel it growing in intensity, steadily building momentum like a heavenly crescendo.

I’ve never had an out of body experience, but this was surely what one must feel like. For a few seconds, where time itself seemed to grind to a halt, I felt like I’d vacated my own needless, physical shell and become one with the metaphysical; my very soul looking down on this semi-paralysed human going through some sort of anal exorcism ritual.

At that moment, I came, which I never even realised you could do out of your anus. I have no idea what it was, or what it’s called, but for the purpose of this article, I’m going to call it a ‘bumgasm’. Just think of a normal orgasm and multiply it by 7000 and you get the idea.

I was in a complete state of shock, what the fuck had just happened?

I scrambled the packaging and toy together, threw them in my wardrobe and sat on the end of my bed, quivering and questioning whether I’d just dreamt the events of the past twenty minutes.

Don’t get me wrong, I was satisfied beyond comprehension, but I was also worried; worried that what I had experienced was so incredible that nothing would ever come close to it again. What if I became dependant on using it every time I wanted to wank, or even worse, every time I was about to have sex? What if it got to the point where I left it up there whilst I was at work?

As uncle Ben said: ‘With great power, comes great responsibility’. Perhaps I wasn’t ready for either.

For now, the toy lies dormant in my wardrobe, a miniature, sleeping volcano ready to burst into life at any given moment. Whether or not I use it again remains to be seen; I’m not convinced it’s right for mere mortals to have such divinely pleasurable instruments at their disposable.

Who am I kidding – it’s inevitable I will use it again at some point – how can one see the promised land with his own two eyes and not be tempted to visit its bountiful pastures one more time?

Reading the product, I noticed one thing that struck me: the O-Boy claims to put the ‘O’ in OMG. A pretty ironic slogan for something that will make you feel like you’ve been touched by the man above.

For showing me the light – to you, UberKinky – I am eternally grateful.

You can check out the full range of UberKinky’s amazing products here.

Alternatively, you can visit their Facebook page.

Images via GIPHY/Channel 4/Rocks-Off Ltd

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