By Pete Richards
Although technically illegal, there’s nothing better for the ego than a foray into prostitution.
Dabbling with the dark arts of pay-for-play and toying with the world’s oldest profession can certainly have its downside but if you plan it right and stick to your rules it can be a rewarding experience.
For your cock and your pocket.
Perhaps my story is slightly predictable. I was a ‘starving Bohemian student’ at the time of my dabble (well, in truth I was studying Philosophy at Durham).
Ok so I had no immediate need for the money but I had a burning curiosity. The seed was planted by a close friend who dabbled in many things…He sold his used underwear online for £30 each (£50 if he deposited some home grown love juice).
Immediately I thought of the potential cash cow squeezed in my undies drawer and all the wasted love juice over the years – Dragon’s Den here I cum!
Despite my entrepreneurial friend’s advice I wasn’t really excited by the idea of posting DNA samples across the world. To me it seemed to take a lot of planning and the queues at the post office were just a crusty pant too far.
I decided to leave the whoring idea to fester in the back of my mind until an opportunity presented itself. Which it did (or this article would be very short and slightly pointless).
I was cruising online [insert preferred site of choice] and doing some general man window shopping; the usual boring offers and one or two predictably scary ones – why oh why would anyone choose to ruin Ben and Jerry’s Chocolate Brownie for everyone?!
Anyway, one of the initial offers, which I eventually dismissed as too run-of-the-mill threw a spanner in the works, which got my turbines going (ok I’ll stop the metaphor now). The usual ‘you’re cute’, ‘what u into?’ became more intriguing with the later inclusion of ‘I’d love to trade a tenner for your t-shirt.’
Either he was insulting my quality of clothing and sense of fashion or he wanted to pay me to strip. ‘Go on…’ I replied.
‘I’d like to watch u slowly stripping for me and as an incentive I’ll put down more money’
‘How far do you want me to go?’
‘How far do you want to go?’
‘How much do you have?’ I was a professional already.
I wondered if it was possible to be pre-disposed to a certain field of employment. I did manage to dismiss the thought of it being in my blood due to the squeaking cleanliness of my heritage. Perhaps I was the rebel, that idea made me even more intrigued.
So he came round, let’s call him John, in true rent boy fashion. John was probably in his late thirties, had a shaven head, piercing blue eyes and a bit of dark stubble with flecks of grey (I do love a silver fox).
John was polite and well dressed, I wondered if his blue velvet blazer would fit me but then was distracted by wondering if that was how these transactions worked. Trying not to zone out as I envisaged myself in his jacket with his money, I was surprisingly comfortable.
Although I had not done this before I genuinely didn’t see anything wrong with it. Okay he could have turned out to be a mass murderer; he could still turn out to be one, but I had written his details down so the homicide police could always find it. Ok enough reality – back to the glamour!
He sat down in my favourite leather chair and looked delightfully regal and overlordy which excited me. I was relieved that my semi was on the way (everyone likes a dramatic reveal). Before I could ask how he wanted to structure the scenario (which would have probably killed the moment) he put ten pounds on the side table next to him:
‘The t-shirt’
I grinned and complied, peeling my tight t-shirt up from the waist and over my chest. I stood in front of him attempting to look coy (apparently this look doesn’t come naturally to me, as I’m sure you’ve guessed by now). Another ten was patted down onto the table.
‘The shoes and socks’
Although I thought he was getting a good deal I happily pulled off my boots and socks. I moved a little bit closer as I greedily wanted to increase the intensity even more. I resisted the temptation to giggle as he looked so smug, placing another ten pounds on the table.
‘Now your jeans’
I unbuttoned my fly and revealed the rim of my white briefs. White, as I thought this was the colour of choice for most porn, and because it shows off the definition more – always good when pleasing an audience. I kicked my jeans off and they landed between his feet.
His legs were wide apart and his big hands hung over the edge of the arm rests, his posture exuding confidence. I also felt incredibly assured and empowered, each time extending the time I took to comply.
‘Your pants. Take them off. Slowly.’
I raised an eyebrow cockily as his down payment hadn’t been deposited on the table. Working my thumbs under the rim of my underwear he rustled with a fiver from his wad of notes. I slid them lower, hovering just above the base of my increasingly hard cock.
I paused, sliding the thick white rim side to side over the start of my shaft, waiting. John plucked another five from his wad and placed it on the growing stack of cash. Flicking his eyes from the money to me, his mouth slightly open with anticipation, I pulled my briefs down and let them drop to the floor.
My cock sprung up, he licked his lips, we both grinned and I’m sure I must have blushed despite my best efforts to be ‘a pro.’
I broke eye contact with him and cast a glance over the money on the table. My maths is terrible but I reckoned there was about £50 there which I thought wasn’t bad for a one on one strip. After all, I’d shown more people the same for free at the nudist beach on holiday (more in my next installment…!)
We’d chatted online before he came over and I’d agreed to let him suck me off but wasn’t sure how to get to that or if each step would be more money (although I hoped it would). I stood there, my cock hanging between my legs, waiting for his next move.
I could see he was staring at it as well and the pause seemed endless and a little bit awkward but I was determined to wait and not ‘break character’ as such. He snapped out of it and asked me to lay down as he put another ten on the stack. I slid into bed, placing my hands behind my head expectantly.
‘Can I come over?’
He seemed to lose a bit of his bravado as it was time to approach me. I cheekily glanced at the side table, perhaps subconsciously, perhaps to suggest that would cost him. Either way, he placed another ten and removed his coat (I hoped it would fall behind the chair and be lost to me forever, but he folded it gently and placed it on his seat).
Sliding into bed, the wad of cash flapping in his back pocket, he ran his hands up my legs and towards my cock. Grasping the shaft he slowly worked it up and down, his hands warm but slightly unsure. It felt good and I told him to keep going, feeling a need to suddenly reassure him.
‘How much for me to suck it?’
‘Um, I dunno, shall we take it step by step and see how far we get?’
I’d become accustomed to our new system: £10 for each escalation. Although in hindsight I should probably have quoted some amount as they next step was to put my dick in his mouth. On placing this ten he ran his wet warm tongue over my cock’s head and down each side of the shaft like he was peeling a skin banana with his tongue.
Although this felt good, it also felt as though he had researched how to suck cock and was being very methodical. I began to wonder how many times he had done this, if he had done this, if I was as good as the last blow job whore. All this thinking culminated in me deciding that he was probably married with kids and that I was the worst whore ever but at least my cock stayed hard and he didn’t seem to notice my inner turmoil.
He stopped and slid over to the table, placing two twenties on the piles of lesser notes. Placing his index finger on the stack and spinning it coyly he asked if I would fuck his face until I came. I thought this was a reasonable request and smiled as I has been waiting to cum all morning.
He removed his shirt and lay back in bed. I straddled his copiously hairy chest, which was in stark contrast with his smooth head. He apologised for his hirsuteness but I kinda liked it (although I was relieved that he was laying on his back as I imagined the body-pubes spread across that manscape too).
As I straddled his broad chest and slid my cock into his mouth I tried to peer round to find a wedding ring. Although I couldn’t see one this idea was beginning to bug me as I really did not want to be helping a married man cheat on his wife, or partner, not being sure which was worse. I pulled my cock out of his mouth with a pop and had to ask:
‘Sorry if this is a random question but are you married?’
He looked stunned and even a bit annoyed. I was worried.
‘What? No. I’m not married. Now can I just suck your beautiful cock?’
The compliment didn’t even register and I still felt awkward which was affecting my, shall we say, turgidity. I sat back on his chest and his hair tickled my cheeks.
‘I’m really sorry about this but I can’t cum if I’m distracted’
Realising that he may not have got such a sweet deal after all (I’ve had friends who have charged more) he propped himself up with his elbows and confessed.
‘I have a partner but we don’t talk about what we do, you know, with other guys.’
‘So you’re allowed?’
‘Yes. Happy?’
Although I detected a faint hint of annoyance I decided to let it go as I still wanted the money and didn’t want to throw him out for being a bit arsey. I fluffed my cock a bit and shoved it in his mouth. I decided I would be slightly rougher with him now for being so oblivious to my feelings.
Again in hindsight this was not punishment at all as the harder I thrusted and the more he gagged, the greater his clear enjoyment. As I ploughed his mouth he hurriedly undid his trousers and pulled out his cock, wanking furiously.
‘I want you to cum in my mouth’
‘What, now?’
‘Yes. Hard!’
I braced my hand on the wall and drove my cock in and out of his mouth. I’ve always been good at shooting on request as I like to edge for that greater final orgasm. Fucking his mouth, I shot my load inside as he came across his stomach and chest, a drop even reaching my butt cheeks.
He continued to suck me and seemed to relish every drop. I smiled and climbed off, grabbing some tissues from beside the bed.
‘Thanks for that’
‘No problem, sorry about the married thing. What can I say, I’m a whore with principles.’
‘Ha, not a problem. Was fun.’
With that he dressed quickly, making polite conversation about my studies. He wafted past the pile of money on the table, dipped into his pocket and put two more twenties on the table.
‘For the great load.’ And he left.
He had regained his bravado and confidence. Funnily, it was that one line that made me squirm and laugh out loud as I could hear him leaving the building. I diligently changed the sheets, did some laundry and genuinely forgot about the £140 sat on my side table.
I remembered it later and decided to splurge on a new shirt and a round of drinks for my friends. I told them all it was my whore money and no one seemed to mind. Well, until I told them it was my great load that paid for their Creamy Orgasm cocktails…