The Telemachus Story Archive

Diary of a Rent Boy
Part 1 - 2016
By Hooder
Email: ukhooder@gmail.com



Diary Of A Rent Boy

8 th December.

“How much for a hand job?”

I looked the guy up and down; sixties, balding, out of condition. Why is it always the others who get the young, cute ones? “Fifty quid.” It was ten more than I’d usually charge but looking at him I was not getting turned on.

“Ten.” He took a wad of notes out, counted off twenty, and then another hundred and waved it slowly in front of my face. “And an extra ten for every minute you can stop yourself from cumming, up to the hundred.”

I smiled. Stopping myself from cumming with an unnatractive guy like him would not be a problem. “Deal.” I forced the tenner into the pocket of my leather jeans (not easy when they’re as skintight as these) and we went back to his place.

“Strip please.”

That surprised me; guys who hire a spiky-haired blond punk boy in tight, ripped leathers usually want me to keep my gear on, at least for a bit. While I was stripping off he was mooching through a wardrobe full of what looked like rubber jeans. “What size waist are you?”

“Thirty.”

“Ah, a slim boy.” He moved slowly along the long row of gear and selected something. “Yes, these’ll be perfect. Put them on please.” He handed me a pair of shiny rubber jeans.

I held the jeans up; they were fairly thick rubber – and they were enormous. “You sure you got the right size mate?” They were at least five or six sizes too big.

“Yes. Put them on please.”

The loose rubber felt cold and very pervy on my legs as I pulled them on. They were about the right length for me, but the rest of them were huge. Far, far too big. I shook my head, takes all sorts, I thought.

He looked at me and smiled. “Perfect. You don’t mind being hogtied, I take it?”

I shook my head.

“Good. Ok. Lie down on there please.” There was a padded mat on the floor. He strapped my ankles together, then my wrists behind my back, and finally connected them with a rope. It was not a tight hogtie, but I certainly wasn’t going anywhwere. Then he took a hood and put it over my head. It was loose black rubber, and there were no eyeholes. I could get air with no problem, but it ballooned in and out with each breath and stuck closely to my face with each inhalation.

“Ok, let’s get you hard, then the time will start.” I felt him kneel down behind me, and then his hand on my legs. His fingers ran up and down, moving the loose rubber jeans over my skin. I’d worn rubber before many times, but never as loose as this, and it was a strange sensation: normally it feels tight, and quickly warms up to your body temperature so you don’t really feel the rubber itself, mainly just the pressure of it – but this was very different: because they were so loose, they stayed cool and I could feel the rubber intensely all over. There were folds and creases everywhere, and with the slightest movement they got into places that felt wonderful. It was very pervy indeed. I noticed my cock was already harder than it had been, and as his hands were slowly homing in on my crotch it wasn’t getting any softer.

He gripped it through the jeans and slid it about under the rubber, squeezing it and stroking it slowly. It slid smoothly from side to side. Then he pulled it downwards, held it there and wrapped his fingers round the shaft. His slow, gentle milking strokes – along with the way the rubber was moving around my balls and thighs - got me fully hard in seconds.

“Ok, the time starts now.” Suddenly I felt his hand force its way quickly between my thighs from behind. He gripped the end of my cock - the palm flat on the end of it and the fingers wrapped around the shaft. He started to milk me hard and fast through the rubber. Instinctively I struggled like fuck in my restraints to keep his hand out – it felt like I was being raped – and before I could do anything about it I was shooting my spunk into the rubber jeans under his gripping, milking fingers, and the rubber hood was pressing tight against my face. There was fuck-all I could do to stop it – I felt totally fucking helpless. I’d never felt anything as remotely horny as this and I’d never cum so quickly in my life. As his fingers worked on my cock the cold rubber jeans moved over my bare skin – it was as if they were milking me me as well.

I curled up into a tight ball as my spunk shot out into the smooth black, cold, creaking rubber and I yelled in frustration as the hundred quid disappeared in a puff of smoke. ‘You fucking idiot!’ I screamed at myself silently as my body jerked helpessly under his hands.

He untied me and removed the hood, then he winked at me.

Bastard. And cut-price too. Ten fucking quid.

“Do you do this a lot?” I asked as I put my leathers back on.

“Oh yes. I love making boys cum like that.” He wiped my spunk out of the jeans and hung them back in the wardrobe. “Are you into PVC?” He asked.

“No. Not at all.”

He smiled. “No? Good. Well, next time nothing down, but twenty quid for every minute I can’t make you cum in PVC jeans. What do you say?”

“You’re on,” I said.

That was something that I’d have no problem with, No problem at all.


14 th December

There I am, watching the traffic, hoping some punter will turn up before long, when I hear this little voice close to me.

“Fucking hell those jeans are tight.”

I glanced round and saw that I’d been joined at the railings by a kid. Sixteen, or seventeen at the most, slim, black hair, and cute. Cheap leather jacket, second-hand Dms, and stretch jeans that were tight, but in all the wrong places. “Yeah, I know they are.”

“You’re a rent boy, aren’tcha?”

“What makes you think that?”

“Cos you’re sexy. Fuckin’ sexy.”

I took a drag on my cigarette and returned my attention to the traffic. But I was smiling.

“Could ya make me cum?”

“What?”

“Rent boys are good at making guys cum. I know. Could you make me cum?”

“You’re too young. And anyway you couldn’t afford me. I charge for that sort of thing.”

“Nah – I’m not asking you to do it, I’m asking you if you could.”

“Of course I could.”

“Even if I didn’t want to?”

“Yep.”

“Even if I struggled to stop you?”

“Yep.”

“How could you do that? If I was struggling, like, resisting, trying to stop you?”

“I’d hold you down. Or tie you up.”

“But I’d yell for help.”

“So I’d gag you.”

“And I’d see what you were going to do and move out of your reach.”

“When you were tied up? Anyway I’d blindfold you so you couldn’t fucking see anything.”

There was a pause, then he said: “You’re the sexiest boy I’ve ever seen.”

I smiled again. “Keep looking at my crotch.”

I did something then that for some reason I’ve always been able to do: I willed myself to get hard. Gradually my cock swelled in my tight, thin leather jeans until it was fully erect. I knew without even taking my eyes off the traffic that the bulge between my legs was huge, and unmissable.

“Fuckin hell,” he said slowly.

I don’t know why, but talking to him was getting me horny, and I suddenly felt devilish. I turned towards him, leaned on the railings and rested my thumb in the pocket of my jeans, with the fingers lightly touching the bulge of my cock. Slowly, I said: “I’d hold you down and cuff your wrists behind your back. I’d force a tight black leather hood over your head so you couldn’t see to fight, strapped on so you couldn’t get it off. Then I’d grip your hard little cock through your jeans and wank you off – very, very slowly so that you could struggle and fight against it, feel yourself losing it - until you couldn’t stop yourself from shooting your spunk into them. Take about two minutes.“ I looked straight into his eyes, and whispered, “And there would be fuck-all you could do stop me. I’m a rent boy and I know how to make boys like you cum.”

A distant look came into his eyes, his legs buckled, and he came in his jeans right in front of me.

After a minute he looked at me. “Got a spare tenner, mate?”

I closed my eyes and laughed. Then I gave him ten quid and went back to staring at the traffic.


19 th December

Being invited to parties is not something that happens to me on a regular basis, but there was this one punter, Damien, who thought I was the most gorgeous boy he’d ever seen, and who was offering me a shitload of cash to pretend to be his loving slave at a pre-Christmas party. Now acting is not one of my most accomplished skills, but for the kind of money he was talking about I was certainly going to give it a go. The rules were simple: I was to look as prickteasing as possible, feel free to flirt like fuck with all and sundry, but if anyone got too close I was to make it quite clear that I was with Damien and that was that. Ok, I thought, I could do that.

One of the most annoying things is that I have no idea where the party was held – I was blindfolded in the car and couldn’t see where we were going. ‘You’re my slave, and you have to be in character’, he’d said. It didn’t occur to me to point out that he could have put the blindfold on me just before we went in.

Anyway, we arrived, the blindfold was removed, and we mingled. I suppose there were about twenty guys there, all of them in pervy gear of some sort. I hadn’t worn anything special – just the gear I use on the streets – and in fact this had been what Damien had specifically asked me to wear. My skintight, thin leather jeans with rips in them; bike boots; studded belt; tight white teeshirt; and a beat-up studded leather jacket. It did the job on the streets, and it looked like it was doing the job here too, because I was getting a lot of very admiring looks.

“Hi Damien. Wow, he’s hot!”

“Damien! Lovely to see you. You’ve brought us a sexy one this time...

“Dami… fucking hell!”

There was a lot of that sort of thing.

Drinks were consumed and spliffs shared. A few times I felt hands on my arse – or occasionally, my crotch – as guys walked past; and I was engaged in conversation often. Damien had introduced me as ‘Brad’ - it’s not my real name.

Most of the guys were your bog-standard leather types, who looked like they were wearing leather as fancy dress, but there was one guy in the corner who really knew how to wear it. His jeans fitted him like they were sprayed on, the collar was turned up on his leather jacket, and his thin leather cop gloves were skintight. He saw me looking at him and came over. “Hi.” he said.

“Hi. I’m Brad.”

He nodded. “Yes, I know.” A smile touched his lips. “See you later, pretty boy.”

I certainly hoped so, though how I could arrange that with Damien constantly breathing down my neck, I wasn’t sure. I decided to find some way of giving him my number before the evening was through.

However it did’t quite turn out like that.

I smiled and flirted, did my get-an-erection-on-command trick occasionally when Damien seemed to be particularly interested in showing me off to someone, and looked as hot as fuck for everyone who was looking - which was most of them, and most of the time.

Probably my first suspicion that things were not quite as they seemed was when a leather hood was forced over my head from behind, at exactly the same time as my arms were grabbed and cuffed behind me, and my ankles strapped together. As I fell over I was caught by many hands, and carried bodily into another room.

I was dumped on the floor, and the strap around my ankles unfastened. Unsteadily I stood up, still hooded and with my arms still restrained behind my back, and waited for some kind of explanation as to what was going on.

The explanation, when it came, was in the form of a hand on my crotch. It felt around, and when it found my cock it began to squeeze and rub. That hand was soon joined by another on my arse, more on my thighs and legs, and very soon I had hands and mouths all over me, feeling, fondling, stroking, kissing, and rubbing through my gear. In spite of everything I started to get hard (involuntarily this time), and my growing erection in my thin leather jeans provided an irresistible target.

I was pushed over and gently laid on the floor, and my wrists were released from the cuffs. Even though I was not restrained at all now, I couldn’t do anything – there were bodies all over me. If I’d been able to see anything I might have been able to escape, or fight them off, or at least avoid most of the attention - but they purposely hadn’t removed the hood, so that I couldn’t see who was where, or where their hands were going, or how to get away from them. Whenever - by chance – my arms found an opening, they were gripped and I was held down while that opening was closed, then released again. It was an infuriating feeling. And all the time uncounted fingers explored until they found my most sensitive and responsive places and worked on them. Very soon I was dangerously close to cumming.

After a while the crowd pulled back. I was lifted to my feet, and held tightly while my jacket, boots and jeans were taken off. I was led to another spot in the room, my arms lifted, and I felt my wrists being cuffed to restraint points. Likewise my feet were secured wide apart.

My hard cock disappeared into a hot, wet mouth. It started to suck and tease slowly. Then a lubed cock was carefuly pushed into my arse. I was slowly fucked and sucked like this, but though I was still very horny, I knew that was not going to make me cum – at least not for a while.

Then most of the crowd seemed to step back. A moment later I felt fingers on my arms. Light, gentle strokes teasing and tickling up to my shoulders; then underneath, up to my armpits. Now I am not ticklish at all normally, but this guy had the touch of an angel – or a devil. My skin tingled for half a minute in the wake of his touch, and the hairs on my arms stood on end. It felt wonderful. To be honest, as a rent boy, the sex I have is usually on the rough side, and I’m not very used to gentle, tactile stuff.

The fingers slid under my armpits, which caused me reflexively to try to pull my arms to my body, but of course they were restrained. The fingers lingered there for a moment, tickling gently, and then made their way down my sides. Just above my hip bones, they suddenly and unexpectedly dug in. I screamed into the hood. I think that was the very first time in my life I’d ever experienced unbearable ticklishness.

The mouth was still sucking my cock (rather inexpertly, it has to be said) but the tickler must have come to some arrangement with its owner, as it – and the cock behind me – were withdrawn. The tickler stood in front of me and I felt his leather jeans against my bare legs. I’m not sure how I knew, but I did know, straight away, that the tickler was the horny guy in the corner I’d seen earlier. This realisation made my cock spring back to instant, and full, erection. He placed it between his leather thighs and closed his legs on it. Then his fingers went back to tickling me.

I have no idea how long it went on, but by turns I laughed, screamed, cried, begged, pleaded, or threatened, depending on whether he was stroking my sensitive spots lightly and erotically, or torturing me by digging his fingers or thumbs deeply into my muscles and nerve centres. And he knew every fucking one of them.

The worst was when he stood close behind me, his leathers pressing into my back and legs, reached around under my arms to embrace me, crossed his arms over my chest, and dug his fingers into my sides. As I struggled and fought against him, the tight black leather hood and the feel of his jeans and jacket – along with the unendurable ticklishness – conspired to get me to the very edge of cumming. And the bastard knew it, because he reached down with one leather-gloved hand, gave my cock just a couple of strokes, and I was jetting spunk all over the place. My legs gave way and he held me in his leather-jacketed arms as I came and came and came.

Ha! I said that was the worst, but it wasn’t. The worst was that the fucker didn’t release me, didn’t stop – but started again immediately. And this time, having only just that moment cum, and without any horniness to help me, my nervous system was defenceless against the tickling – and hypersensitive to it. And it was pure, pure torture . Imagine someone continuing to work on your naked cock when you’ve just cum, and not being able to stop it – the tickling was like that, though indescribably more intense.

A tiny part of my mind registered laughter (and possibly the sound of guys wanking off as they watched) from the asembled onlookers, but mostly my brain was busy trying to remember to breathe, and processing the unbearable stimulation as I was sadistically and mercilessly tickle-tortured.

He made me cum three more times, and after each he set about me with renewed intensity. Each time it got more unendurable. I screamed myself hoarse. The last time was a dry cum, but even then he didn’t stop. And at that point I pissed myself, and then I fainted.

I came to in the first room, lying on the settee. I was dressed again in my gear, and my arms were again cuffed behind my back. Damien smiled at me. “A nice performance. Thank you.” Then he took a length of duct tape and pressed it carefully over my eyes. I was guided out (more hands on the crotch and arse), and into the car.

Damien’s last words were: “There’s a blade to cut the plasticuffs off on the ground close to you. Don’t cut yourself.” With that I heard the car drive away. It took me a few minutes to find the blade and by the time I’d ripped the tape off my eyes Damien was long gone. I was in a car park in town at three in the morning and had to walk home.

Note to self: get the fucking money first next time.


22 nd December

I’m keeping a low profile and nursing a black eye at the moment. Yesterday a girl wanted to suck me off. I told her I’m guys-only. Five minutes later her brother arrived and beat the shit out of me.

But I nicked his wallet :)


26 th December - Boxing Day.

Christmas Day was a total farce this year. My flatmate, Vomit (she’s also a punk and an occasional lay) gave me a radio-controlled vibrator for a present yesterday morning. Well, she said it was a vibrator - and it could indeed vibrate - but it could do other things too. She didn’t tell me about those.

She tied me to the bed and tried to edge me with it, but the thing felt delicious and I came far too soon. ‘No, keep it on,’ She said afterwards, and sent me down to the corner shop to get some cigs. I’m just passing the bananas when a pair of pincers grabs me round the balls and squeezes. Fuck did that hurt! The cow hadn’t told me the thing could deliver electric shocks as well. I must have lashed out cos the next thing I know I’m writhing on the floor under an avalanche of fresh fruit. Bitch.

Today, however, was bizarre in a completely different way. I don’t actually spend much of my time on the streets looking for trade – most of my clients contact me through the net – and this one sounded strange, but interesting. He’d said that he wanted me to be the main attraction at a Boxing Day rubber gathering he was holding in a ‘special complex’. The fee was particularly good, and so I agreed.

I was met at the front door of a building in an industrial estate by a guy in full black rubber and a gasmask, led into a locker room and told to strip. He reappeared ten minutes later, and took me into another room. This looked like some kind of extraterrestrial laboratory: there were strange machines standing around; corrugated rubber tubes snaking across the floor; and the walls were all mirrored. I was led to a long, thin table padded with black rubber. It looked odd: there was a drainage channel running around the edge, and a hinged plastic cover of some sort - I couldn’t see exactly what it was - hanging down the other side. He told me to lie down, and restrained me with my arms slightly away from my sides, with some kind of cuffs and straps that clicked into place. I could hear the sounds of conversation and the clinking of glasses coming from another room.

He fitted a rubber anaesthetic mask over my nose and mouth, pulling the straps tight behind my head. “You’re going to enjoy this,” he said. Then he took a huge container of lube, and covered me with the stuff from the neck down. Every inch of me was swimming in it. He placed a squeeze bottle in the corner by my left foot, then went round to the other side and swung the hinged cover into place.

Have you ever heard of a ‘glove box’? It’s a thing scientists use to manipulate dangerous substances; it’s a box with a strong plastic cover with pairs of holes in the sides. There’s a long black rubber glove sealed to each hole, and they put their arms into these from the outside to handle whatever it is they want to work on. Well I was in one of those. A big one. There were two pairs of empty rubber gauntlets hanging down limply on each side – one at my crotch level, the other by my chest – and another pair at the foot end of the box. The guy locked the cover down and then went off, presumably to tell the others that I was ready.

A couple of minutes later I saw people coming in. There was a large operating theatre light array directly over me, and the illumination in the rest of the room had been dimmed, so I could only see vague shapes through the plastic – but everyone was in full black rubber, and as far as I could see they were all masked. I breathed slowly, the mask over my face smelling of rubber. I tell you, it was a bit scary.

They looked at me for a while, chatting and nodding to each other, and then, one by one, the rubber gloves started to fill out as people put their arms into them – it was like they were coming to life on their own. Shiny black rubber fingers flexed alarmingly in my direction. And then they were touching me, the shiny, smooth rubber gliding on the thick film of lube over my skin.

It felt amazing. There were hands everywhere – running over my arms, into my armpits, down my sides, across my chest and stomach, down my legs, over my feet – but they seemed to be avoiding my erogenous zones for the moment, Even so, I started to get hard – a fact that didn’t go unnoticed by the crowd.

Suddenly I was aware of poppers: they were feeding it to me through my facemask. Poppers have always had a strong effect on me, and today was no exception. A few seconds later my world began to revolve and close in, and at the centre of that closing circle was my cock. It was as if a mental magnifying glass were being slowly moved down from my head to my crotch, and I began to feel very enthusiastic indeed about what those rubber hands were doing.

One of the figures moved towards my head; he was holding something in his hands. Even though he was masked I could tell that he was grinning as he lowered it towards me – it was a complicated black rubber hood with tubes attached to it. He gently lifted my head and – with sadistic slowness, he pulled the hood down over my face. It had clearly been designed to accommodate the anaesthetic mask, as it fitted perfectly, with straps that tightened it over my eyes and around my neck. That hood, along with the effect of the poppers, made me feel intensely helpless. The instant his hands left the hood, the focus of my consciousness returned to my body – and then to my cock. I was fully hard now, and the rubber hands were homing in on my responsive areas. The upper ones were sliding over my nipples or getting into my armpits; there was a hand gliding up my cock shaft and over the head; another was exploring my balls; a finger had parted my buttocks and found my arsehole – it said hello to my sphincter and then worked its way gently but unstoppably inside; and the bottom pair of hands was sliding smoothly over my feet – across the soles, between my toes... I had never felt anything like this before in my life. I felt myself building up to orgasm – but then, of course, the hand on my cock stopped. It stayed motionless, just holding the shaft gently.

I became aware of a sound – a tone like a low whistle. It had been steadily climbing in pitch, but now was staying at the same frequency – and then, gradually, it started to descend again. A horrible thought crossed my mind.

The hand on my cock began its teasing, gentle work again, this time concentrating on my cock head. The tone began to rise, rather more rapidly this time, and I knew then that my fears were right: they had some kind of biofeedback monitor connected to me, and it was telling them how close to orgasm I was. This was confirmed when the hands stopped a moment later, leaving me closer to orgasm than I’d been so far.

The guys (perhaps some of them were women) were clearly capable of learning, as their experimentation was telling them which spots on my body were most responsive, and also what techniques were most effective on me. Soon they were pushing every one of my buttons, and playing me like a fucking musical instrument. The tone rose higher each time as they brought me ever closer to orgasm before stopping before I could actually cum. Every few minutes I got a blast of poppers through the mask, and whenever that happened I became intensely conscious of the rubber hood making me helpless, the mask over my face, the straps over my body and arms holding me down, and of course the slippery rubber fingers working on me. Now and again someone would pick up the squeeze bottle and pour even more lube over me.

I have no idea how long this went on – I lost count of the number of times I was brought to the edge but prevented from cumming. And each time that tone reached a higher pitch. The fingers continually became more skilful, more effective on me: now just a touch or a stroke on various parts of my anatomy would have me desperate for orgasm. And they were keeping me on the edge for longer each time too – at those points, balanced on the knife-edge of cumming, I was beside myself with the need for release – I would fight the restraints, trying desperately to get my hand to my cock to finish myself off, or to get their rubber fingers to do it; I was capable of thinking of nothing else but my indescribably urgent, compelling need to cum. But always, always, they stopped. I could have killed the fuckers.

Then, suddenly, several things happened at once: there was a ‘click’ and I felt the straps over my body release. My wrists were still restrained, but the rest of me was free inside the box. I heard – and felt – a pressure change inside the hood, and the rubber sucked in, clinging tightly to my face. I got a huge blast of poppers, and then my air was cut off completely and I couldn’t breathe. The rubber hands started to work on me faster. Reflexively I started to struggle – whether to get away from the hands or to try to make them make me cum I don’t know – but I struggled like fuck inside the glove box. This was insanely frustrating because the thick plastic cover prevented me from curling up and there was no way I could get away from those fiendish rubber gloves. They followed me wherever I moved, sliding on my lubed body, teasing, tickling, working on me. The finger inside me was fucking me hard; I’d got a rubber glove clamped between my thighs, the fingers milking my cock-head irresistably. I couldn’t breathe, I was high on a poppers rush, I was desperate to cum, and I was totally, absolutely fucking helpless.

To say that I came is an understatement: I exploded. I felt the first gob of spunk shoot out of my cock like a bullet – it must have made a fucking dent in the plastic cover of that box. There were rubber hands all over me, and the one on my cock-head continued to extract my spunk methodically and relentlessly. I was being comprehensively milked and I was in absolute rubber heaven.

As my orgasm subsided and then stopped, air returned and I could breathe again, the pressure in the hood returned to normal, and the rubber hands retracted. Moments later the hood was removed and a masked face looked down at me. “I think we made you cum,” he said.

The crowd went back to the other room, and the guy released me. “There’s a shower in the locker room. When you’ve got dressed come next door for drinks”.

When I entered, a cheer went up, and I was plied with intoxicating liquor for the next half-hour. I was the only one not wearing a mask of some sort. I was propositioned by a few people (I was right, some of them were women), and consequently I have a number of new clients on my list.

So, a strange Christmas, but fun.

And to think that I get paid for this...

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