By Omar Hassan

I am 23 years old, of medium-build, just under six feet tall, with broad shoulders, curly black hair, and a bit of stubble. My sexual forays — both in terms of my long-term relationships and with fleeting lovers — have found me constantly gravitating to younger, skinny, and smaller men, whom I would consider ‘natural bottoms’. However, with time, these men no longer inspired me, sexually speaking. What I really wanted was someone tall, big, hairy and unkempt, with musky armpits and speckled white hair — and, most importantly, to feel the full throttle of their bulky dick up my arse. I started lunging at every opportunity that presented itself to meet one of these guys.

It didn’t take long before I realised that I had a major problem: despite a Gaydar profile that reads ‘versatile’, the first and last time I explored bottoming was as an 18-year-old, when a 25-year-old American rammed himself so far up my derriere that it left me shell-shocked. I spent the next three days feeling as though I had been raped and decided then and there that such activity wasn’t really for me.

With my new conquests in mind, I figured I had to learn to loosen up. I turned to one of my dearest (non-fuck-buddy) friends, Philip, whom I’ve known to be a mid-weight top with a modest-sized penis. He agreed to ease the path for me one night, while over at his place. After some chitchat, we got undressed and he gently stuck one of his fingertips inside of me, before pushing me onto my stomach, and proceeding to carry out what I’d asked him to do. What abounded was a horrific, and unexpected, revulsion on my part, but my incessant shrieks didn’t seem to persuade Philip to slow down’. Luckily he wasn’t a man of stamina, and after he quickly finished up, I waltzed home, trying to bottle up my embarrassment.

But I wasn’t going to give up. Next I tried it with Adam, a tracksuit-sporting football fanatic who, despite his healthy girth and size, promised me that he was far gentler than he seemed. But when it came down to it, I panicked. I bailed by using the old-school tummy-ache excuse. We turned on the TV soon after, and before long he was snoring. Then there was Sandy, a builder. Sandy was dark, gruff, and complimentary. But when I unzipped his trousers (in the front seat of his car), I realized he was of mind-boggling size. After ten minutes of polite cock sucking, I asked to get home (‘I’ve got a deadline’), and with that disappointing cue, it was over.

In the midst of my despair, I wondered: was it simply a sense of control that I hankered for? Had I never really been taught to let go? Perhaps, if I could manage to control the penetration myself, I could develop the confidence to make it work with someone else?

I decided to take a trip to a local sex shop and get myself a beginner’s butt plug. I unwrapped my new toy at home and started massaging my tight entryway. I attempted every technique I could think of: lying on my back, from the side, sitting on it when I felt relaxed, all lubed up and intoxicated enough after numerous glasses of wine and snorts of poppers. But whatever I did, my new butt plug simply wouldn’t fit. I angrily went online to splash yet another 25 quid on a novel form of anal stimulation. This time, it was a discreet pencil-shaped vibrator that could be carried around everywhere. But since I was going to have to wait 48 hours before it would arrive, I ventured towards the kitchen, popped open the fridge and hornily started surveying any long, solid items that I could use to ease the way. A cucumber? Too much water involved, I thought. But a carrot should hold up. I picked one out and trimmed the edges until I felt the girth would be sufficiently painless. Back in the bedroom, I popped a Lucas Kazan porn flick into the DVD player, closed my eyes, and started thrusting the carrot in and out of my arse. Delightful, I thought. This was easy. But somehow the dudes in the film were having a much better time than I was. As much as I tried to imagine that the now flaccid carrot was a throbbing cock, the bounds of my imagination simply wouldn’t allow it.

My new toy arrived the next day in a subtle packaging. I have to admit it did everything it proclaimed it would do on the tin. But after about a week of agreeable yet inoffensive self-service, I started a process of righteous questioning. I was no more eager to seek the real than before. Certainly, the sex toy made the process of self-pleasuring a more full-body experience, but the act of using it lacked the spontaneity of real sex, and was perhaps even to stunt any future sexual adventures with men rather than toys. And it wasn’t going to make me a better lover, because in the real world, I knew, I would never have the option to choose the girth or length of my partner’s penis. And the more I developed a relationship with my vibrator, the less likely I was to find a proper man who could actually fuck me. In the end I was almost worse off than when I started.

A couple of months have passed now since I began these reflections, and in that time, I found myself in a relationship with a man called Brody, who seduced me by talking endlessly about how he would fuck the living daylights out of me. Yet, every time we got down to business, our heavy petting would end in embarrassing fits of laughter — his cock lingering somewhere in the ether, rarely making its way beyond the mildest penetration. When Brody would leave, I would return to self-pleasuring, one finger up my hole, wishfully deluding myself that he was inside of me. But he wasn’t, and he hasn’t managed to bring it home since then. Now, when I hear of my friends who manage to hold up both lifestyle choices, I find myself teeming with jealous confusion.

It seems that despite my trials with dildos, butt plugs, vegetables — and real guys — I am still not ready to become the bottom that I fancy being. I am still hopeful though that with the right timing, and the right fella, I will be able to turn things around. Until then, I carry on in my sexual rut — bouncing guys off the end of my cock, envious, and perplexed by the pleasure they seem to be getting out of the experience.