‘Have you got any toys? I wanna see some ass play!’ the message read.
Oh dear.
This was part of the problem. Believe it or not, I’d never in my life owned a dildo, a vibrator, nor any other kind of sex-based toy. The best I’d been able to offer to my clientele up until now had been me jerking off my cock, rubbing myself in baby oil or flashing my arse, but clearly that wasn’t going to be enough in the long run, and now they were craving something more.
‘No toys sorry. But I’ve got a nice sized cucumber I could use,’ I replied, my cheeks flushing crimson red, even as I typed out the words.
I waited nervously for his response.
‘That’ll do perfectly,’ he said. ‘So Skype yeah? How much for a 30 minute show?’
I really had no idea what to reply. I didn’t want to throw out a figure that he’d refuse, but I felt embarrassed asking for anything more than £20. To some degree, even that seemed expensive. But I reasoned that 30 minutes was a fairly long time to be screwing my ass with a cucumber, and I’d surely be pretty worn out by the end of it, so I wasn’t prepared to do it for any less.
‘£20 is fine,’ he said. ‘Paypal?’
I shut down Cam4 and logged into my Skype account. After giving him my PayPal address, he transferred the money, and I scurried away to the kitchen fridge to grab a cucumber that looked a decent size.
That in itself was a problem.
There were only two available – one already slightly cut in to and so pathetically small I could probably have fit the damn thing up one of my nostrils – and as for the other? Well let’s just say it was rather beastly, both in length and girth, and I really, really, really didn’t wanna put it in me…
Too late though. The session had been paid for and as a man of my word; I had to keep up my end of the bargain. I wiped it down and then wrapped a condom around it for sanitary reasons, before returning to the living room – armed and ready to put on my first independent show.
Firstly, I balanced my laptop on a slightly rickety coffee table a metre or so away. I then got on my knees in the doggy-style position on the leather sofa, with my pre-lubed arse up in the air facing the computer. I waved the cucumber up so he could see it, and then covered it in as much baby oil (the only form of lubricant available) as I could. Having not been fucked in a fair few weeks, and without so much as a bottle of poppers to hand, I knew this was going to be potentially incredibly painful, but I put on a brave face, thought about the money and started to ease the condom-covered cucumber inside of me.
For the first 5 minutes or so I teased the client with just insertion of the very tip of the cucumber, which was painful enough in itself, but pausing for a moment to get close enough to the screen to read his messages, it was clear he wasn’t satisfied.
‘DEEPER!’ he’d typed.
‘Can’t you fit it all in?’
‘COME ON!’
I felt like a rabbit in the headlights. We were only 6 minutes in to a 30 minute session and already I was feeling the heat, and the pressure to perform.
“This ain’t no little cucumber here,” I said to him aloud with a nervous giggle. “It hurts ya know!”
‘Move cam closer,’ he responded. ‘Closer so I can see!’
I moved the table a few inches nearer and angled the screen so the webcam was focused more prominently on my arse. I then took a deep breath, tried to relax my sphincter muscles as best as I could without the aid of poppers, and pushed the object deeper and deeper inside myself.
“Argh!” I grunted. “Ah fuck.”
I turned my head to see what he’d typed out in response.
‘Better,’ he wrote. ‘Now fuck harder! Fuck that tight little ass!’
I did as he’d requested and tried to look like I was enjoying it, yet truly I just wanted it all to be over. My arse really wasn’t ready that particular evening to take such a hard pounding. I grabbed the bottle of baby oil from the side and smeared another handful of it around the rim of my hole, then covered the cucumber in another layer too – ready for further insertion.
I counted down in my head.
3, 2, 1
And in it slid. My arse was loosening up by this point, but the jagged end of the cucumber was pressing up against my insides in the way a regular penis wouldn’t, and the pain was intense.
Ironically, I have a tattoo on my inner right bicep that reads ‘Pain is Inevitable, Suffering is Optional’ – a quote with origins in Buddhism that I took an instant liking to. But it was hard in that moment not to think of myself as a victim, despite my agreement to carry out the show.
‘MOAN,’ the client wrote. ‘Moan louder!’
I was already screeching in pain, but it was close to 2am, and my family were upstairs sleeping. I turned up the volume on my microphone, so that my squeals could be heard more clearly without me having to scream the house down, and carried on till I was dripping in sweat, and physically couldn’t take a single second more.
We were 26 minutes in. That was as close to the 30 we’d agreed upon as far as I was concerned. I lit up a cigarette and chatted with the client for a further 4 minutes.
It turned out he’d enjoyed it (despite being so demanding about it all), and as I recall he became my first real Skype ‘regular’ – requesting similar shows each week.
As I shut off the cam and analysed the condom covered cucumber, I noticed for the first time that it was covered in blood. No wonder the session had been so painful! I’d pushed myself way too far and my body was now crying out in pain. £20 seemed like a pathetic sum of money when I actually sat down afterwards and thought about the intensity of the session, and what I’d just put myself through in the pursuit of it.
I felt like I’d cheapened myself, and there was little I could do but just pray that my arse would heal quick enough so that I could perform again soon, and hope that I hadn’t done any major damage to it.
Following my disastrous incident with the cucumber, I knew I needed to get at least one vibrator or anal toy to keep up with the competition. Next stop? Straight to Google, in search of just that…
For the most part, like my clothing, I buy my sex toys online. The first vibrator I ever owned was from Bondara.co.uk – in the picture and the description it was advertised as ‘Big Red’ and I chose it because it was on Sale. When it arrived I was disappointed to find that ‘Big Red’ didn’t quite live up to its name. It was more ‘hot pink’, and not really all that big or impressive looking. Other than that one particular vibrator though, I have to say that everything else I’ve bought from Bondara has been top notch, and always for a good price. They frequently have discount offers available, and if you order enough in one go you get free delivery along with it – so I usually try and stock up when I have the money to.
In total I now own both ankle and wrist restraints, a variety of cock rings, a leather gimp mask, nipple clamps, a flogger, two dildos, a blackout blindfold, a penis pump (which I almost didn’t buy, but happens to be one of my favourite toys to play with) and a ball gag. I also like to keep a clear plastic funnel to hand, which I brought from a general hardware store – it’s got multiple purposes in my shows but generally makes its appearance when the water sports (piss-play) fanatics are around.