A Working Boy

I’ve been doing this since I was young. And I have zero regrets. None. I love it.

Some kids get a paper round, some work at the local store, some mow the lawn for folks down the street. Me? I realised early on that bending over and letting guys fuck me was a more enjoyable way of earning some cash and, my god, I earned more than if I’d had a fucking paper round!

These days I have my own streaming channel, regular customers, and a thriving little business. I’m not earning millions, but I earn enough to be very comfortable and do what the heck I like all day, every day. I’m not on anyone’s clock but my own, I don’t have to grovel (unless the guy pays extra, y’know?) and if I can keep doing this for maybe three or four more years, I’ll have enough that I won’t have to do any real work for the rest of my life. Not bad for a sweet, eighteen year old twink boy.

I was seeing a regular today. He was boring perhaps, but he paid well and he never took up much time. He was an older guy, like most of my customers.

I preferred older guys. They tended to treat me nicely, like I was precious. And they had more disposable income that I could tap into. And I liked the feeling I got when some older, bigger guy held me tight, squeezed me, did unspeakable things to me. I really liked those dad bodies. You know, a little paunch, the hairier the better. They were always so attentive.

My first guy was older, hairy, with a gut that hung over his belly. Any time I saw one of those guys it took right back and gave me the sweetest thrill. Unlike a lot of people I knew, I looked back fondly on my first time. I often jerked off thinking about it.

I had already cleaned out and I was finishing in the shower when my phone pinged. I stepped out of the cubicle, naked, and glanced at the screen. My guy was running ten minutes late. Really sorry. Lots of hearts and kisses. That was cool. I was late getting up and ready this morning anyway.

I brushed my teeth and lubed up. This guy preferred to get in and out, especially if he was running late, so it was better if I squirted some lube up there before he got here. I always tried to keep it inside and off my anus as loads of these guys liked to eat me out and a freshly lubed hole was aways a turnoff. Tricks of the trade, learned over five years of being a cum slut.

I selected some underwear. This guy liked jock straps. He wasn’t interested in my cock at all…. Just the ass. He wouldn’t remove the underwear, he’d just fuck. That suited me just fine. There was nothing like being held down and taken up my back passage in the late morning.

I shivered at the thought and my flesh came out in goosebumps. God, I was a so hot for it.

I tidied up and rearranged the cushions on the sofa, folded the blankets that I had wrapped around me last night as I sat watching movies. Anything to keep my mind off sex until he got here.

I grabbed the little watering can from the side in the kitchen and gave my pot plants some life. As I watered and looked the green foliage, it took me back to that first time.

I was in the woods, playing out. I was alone, because I was always alone. Other boys wanted to play stupid games and all that interested me was touching myself. I was physically more mature than most of the boys, but I was sexually lightyears ahead. I knew already that I didn’t like girls, not in that way. I didn’t like ass either, I liked cock. They fascinated me, and they made my hole itch like it was sending me a message even at this tender age. I often played in the woods. The trees and undergrowth and bushes offered up places to be private, to explore my body, and to wank myself silly. And it felt so naughty pulling down my pants out there. Naughty thrilled me more than just about anything.

The buzzer sounded three times. He was here. I placed the watering can down on the worktop and hurried to the door. I peeped first just to be sure, then I flung the door wide and jumped into his arms dressed only in the white jock with red piping along the elastic.

He grabbed me with big strong arms and kissed me, his stubble beard rough on my fresh face.

“Sorry I’m late. Fucking traffic in this part of town sucks!” He said through the kiss. His hands were already moving to my ass, sending waves of thrilling energy up my spine.

“It’s okay” I said. “I’m just glad you didn’t cancel on me. You on your way to the airport?”

“Yeah, flying out in a couple of hours. Just enough time to see my boy.”

I kissed him hard, both hands on his face and my tongue in his mouth. His hands were now cupping my bottom, holding me up, my legs wrapped around him.

“Will you take me, big man? You have time?” I said in a sultry, sex-fuelled voice. “Empty your big balls inside me so you’re not horny for the flight?”

The guy squeezed my ass, walked forward and kicked the door shut behind us. “Oh baby, I’m gonna fuck you. Yeah. You’re such a sweet thing. I’ll always make time for that.”

“You’re a sweet little thing” the man in the wood had said to me, all that time ago. Ever since then being called sweet made me think of him. He must have thought all his Christmases had come at once, stumbling across me laying there, my shorts and Spiderman briefs pulled down to my knees, my t-shirt pulled up to my nipples, little teen boy cock in hand.

I sniggered.

“What’s funny, baby?” My client asked.

“I was just thinking about what that kink in your dick does to my insides” I lied and I kissed him again. He growled in appreciation.

“You must see so many men. I’m amazed you can remember the details” he said. What was this, a pang of jealousy perhaps? I could cure that.

“I don’t see that many. And I remember my favourites.” I said with a sweet smile and big eyes.

He put me down gently on the sofa and I knew that he’d quickly moved on from questions about who else I got with. He looked down on me with ravenous eyes. I loved that look.

The guy in the woods had that look too. That’s how I knew I wasn’t in trouble having been found in a compromising position by an adult. The look said everything. It was hunger and lust, like he couldn’t look away and had to drink in everything that was in front of him. I remember the intense thrill I got in my balls that first time with the realisation that my semi-naked body had caused such a reaction.

I lay back on the cushions and bit my lip seductively. This was a huge sofa, with comfortable deep cushions, a low back and low, comfortable arms at either end. I had chosen it especially. It was long enough to lay down full length, deep enough to roll around, the the back and arms were perfect to be bent over. It was easy to clean, too, although I’d had to have it reupholstered twice. Cum can be a bitch to get out, you know?

He leaned over me, cupped my face with his hand. I loved these big guys bearing down over me. It made me feel so small and helpless at it constantly reminded me of the early days.

That guy had leaned down over me too. He’d dropped down to one knee and leaned right over me, gently pushing me back to get me to lie flat on my back in the undergrowth. My pulse had been racing back then, my body flooded with new sensations that I found fascinating. I guess some boys would have been scared, but not me. I welcomed all of it and I invited more. The butterflies in my tummy, the fizzing sensation behind my scrotum, the flush of colour and goosebumps, and of course the thudding of my heart as it pumped blood around my body like never before.

My client reached down to my hips and gently turned me over. I put my head into the cushions and waited. He’d get undressed now. I loved the sound of that. The jangle of a real man’s belt buckle and the gentle hissing sound of clothing on skin as pants and shirts were removed. That thrilled me. It heightened the anticipation.

Back in the woods, the man reach for his belt and that’s when I first head that sound. As I lay there I knew what it heralded. He was going to remove his adult penis from his pants. He was going to show me his, because I was here showing him mine. My eyes went wide as he pushed his jeans down, taking his boxers with them. There it was, a huge dick hanging down over his balls. Hairy and mature. I couldn’t tear my eyes away. I wanted to see him every bit as much as he wanted to see me. He placed a big warm hand on my hip and pulled me toward him, turning me onto my side so that my head - my mouth - was closer to his manhood.

I didn’t need any further encouragement. I opened wide like a baby bird and I engulfed his flaccid penis. I could feel his pulse on my tongue, feel the blood pumping to engorge him as I ran my tongue around his growing purple head. His hand squeezed my hip and I wondered if he would touch me back there. I longed for it. I wanted to be touched where no-one had ever touched me. It was awesome when I touched myself; how wonderful would it be when someone else did it?

My client placed both hands on my ass. They were big and warm and surprisingly rough for a businessman. I pushed up a little, giving my back a tiny arch. His hands spread my cheeks and he spent a few seconds looking down at my hole. I know he loved it. He liked to look, this one. And I liked to show off.

I thought back to my first time. The guy in the woods. He liked to look, too. He caressed my face and ran his fingers through my hair as I sucked him. I loved that. It was like being told that I was a good boy by touch alone. It encouraged me to suck all the harder. I brought a hand up to touch him, to feel his thick shaft and hairy balls. I started to taste a saltiness from his pee hole and I knew it was precum. I’d tasted my own, of course, and I wondered if I could get him to shoot into my mouth.

He’d pulled away from me though, causing me a momentary pang of disappointment that melted away quickly though when he said “can I…. Can I touch you…..?” in tentative tones.

The thrill that shot up my spine has never been repeated and I guess it will never be. I seemed to lose all ability to control my muscles as he pulled the hand that was on my hip, rolling me over onto my front. His hand snaked around to the small of my back and he ran two fingers down into the gap between my ass cheeks. I gasped as he touched my tiny pink hole. It was as good as I thought it would be, an electric shock of sexual thrill that had me arching my back like a pro and pushing my bottom up to meet his fingers.

He sniggered. He pressed against my bud. I moaned. “You like that…..” He said.

My client’s tongue swiped from the back of my balls, across my hole to the base of my spine. I shuddered with barely concealed excitement. One thing about this otherwise unremarkable guy was his tongue. It was big, wide, hot and wet. And boy, did he know how to use it. I took a deep breath and let myself sink into the pleasure of it as he ate my hole.

The stranger dribbled spit into my crack. I felt it spatter just below my anus, felt his thumb collect the saliva and push it to my hole, rub it around, making me slick. I felt as the tip of his thumb pushed gently at first, opening my ring until the tip was through. I was breathing heavily. I had never felt so sexy, never felt so much like I wanted more of something than I did right then. My face was buried in my jacket that I’d been using as a pillow. My knees were scraping on the dirt and there was something about that which made me even hornier. I pushed back some more, pushing my ring around his thumb and trying to relax enough so that more of it would enter me.

He snorted in a way that told me he liked it. I started to wonder if he might go further. Was this a fumble and then he’d get scared and run off, or would he overlook my youth and try to push that big, hairy dick of his inside me. Oh god, please push it inside….

“What’s that?” My client asked around tonguing at my hole.

“I said please, daddy… please push it inside me” I silently admonished myself for speaking my thoughts out loud, vocalising my daydream. Now he’d stop with that wonderful tongue action. I wanted the cock, of course, but I was always down for laying here while a talented tongue explored my ass.

There was some pressure and the thumb pushed right in, right past the knuckle. I flinched, but immediately pushed up to meet it. It was amazing. I’d shoved all manner of crap up there, but nothing had ever felt as wonderful as this guy’s thumb. I bit down on my jacket.

The stranger thumbed and fingered me for a while, his face close to the action so he could see my ring split open as I allowed his digits to work me loose. I pushed back, I breathed heavily, and I let my pulse go wild. My little dick was soft but dripping with salty goo. It was just incredible.

My client used both hands to line up his dick. He was rock hard like always. He rubbed the head of it around down there, getting himself wet and sticky, watching his manhood rubbing against my pink anus. He liked that. I could tell. He pushed and I made ready, my eyes shut as I savoured that feeling of a man’s hard penis sliding into me. I hoped to god this feeling never got old, because life wouldn’t be worth living if I ever got bored of it. I was tight, but it went in easily.

My first time wasn’t so easy, but it was thrilling nonetheless. The stranger took his hands away and paused for a long time, just watching and I guess assessing the situation. I heard him playing with himself, maybe thinking about whether he could go all the way. Then, moving swiftly all of a sudden, he shifted his position. He was bearing down on me, his body longwise along mine. I felt his big hard dick sliding along my crack and the thought of what was coming took my breath away in the best way possible.

He leaned to one side, awkwardly fumbling with one hand between his legs, trying to line the head of his dick up with my hole. I tried to shift position, to make it easier. He got there eventually and I gasped as I felt it pushing it the right place.

He was rough, the stranger in the woods. Having decided to go for it, he made the decision to take what he wanted before anyone could stumble upon us, before he changed his mind. Before I did. I didn’t care though. All that mattered was that he did it. That he ripped my virginity away and showed me what it could be like.

He thrust hard and the head of his dick tore into me. I bit down on my jacket and kept quiet despite the pain. I tried to relax, to push back up. For a minute - maybe less in reality - some stuff back there didn’t feel right, like he wasn’t in properly or something. Then, with a suddenness that surprised me, something kind of clicked into place. His penis was half-way inside me and the pain was quickly fading, the pleasure sensations quickly building.

Stranger, one. Virginity, nil.

I smiled, then grinned. I couldn’t stop it. This was it. My fantasies and dreams faded in comparison to this reality.

“Is it good?” He asked, an urgent whisper. I waste sure he cared. Maybe he just wanted confirmation that I wasn’t crying or something.

“Please don’t stop” I said. It was all I could manage. But it was enough. The stranger pushed down on me and I felt his hot cock slide fully into me, a feeling I loved then and I still love today. It filled me up with heat, with a new energy, and it sent wave upon wave of sexual thrill arcing through every inch of my young body.

“Oh what are you doing to me…..” I whimpered. I don’t even know where that came from. It just came out.

“I won’t be long. Lie still” he said, misinterpreting my words but not willing, not now at least, to stop. He thrust, fucking faster and faster. I quickly got the hang of it, of relaxing and gripping and making it feel awesome. I wanted it to go on. I wanted time to remove my shorts and underwear so I could spread my legs open for him. Maybe I could go on top and bounce up and down like I’d seen on the internet. I really wanted to try that.

But that was not to be. Not this time.

My client was thrusting away, happy as a kid in a sandbox. He had a way of thrusting with his buttocks which, I must admit, felt nice. It was a one-trick show however, so I simply lay there and focussed on that glorious sensation of a man’s flesh sliding across my threshold, sawing away, creating heat and melting my spine with electric current.

This guy was good, but never the most exciting or inventive fuck. I’d had far worse. He’d finish in a minute. He never lasted long when he was looking down at his dick sliding into my pussy.

The stranger pulled out before I could try all the things that my young mind had conjured up for us. I felt the head pull out of my sphincter. I felt myself close up, but not all the way. I sensed him jacking off behind me and I heard him grunt, felt the heat of his cum spatter over my hole. Then I felt him push against me again as he used just the tip to push his juices into me. I whimpered. My first experience with another man’s cum.

My client pulled out just in time. He shot his load over my cheeks and up my back. He always had a lot of spunk to give and I loved the heat of the little drops that cooled so quickly. He was always loud when he came, too, grunting like a bear. I enjoyed knowing that he’d cum for me, because of me. It was one of the most satisfying things for me about sex. You couldn’t fake that.

One of these days I’d convince him to sow his seed inside me. I loved that, the feeling of a big man’s dick pulsating right up in my rectum. Anything that toyed with my ass was welcome.

The stranger fingered my sticky hole, looking all the time. He turned me over and touched my dick, soft and small and shrunken away but dripping in a way I’d never seen before. At his soft caress I got hard, but he didn’t finish me off. He looked down on me from his knees, assessing what he’d done.

“Okay?” He said.

I nodded. I smiled too. Don’t worry about me, pal.

“You can’t tell anyone about this” he said, his voice low and urgent.

“I won’t.” I said quickly and with passion. I needed him to believe that. “Will you do that again?”

He looked at me with big, wide eyes. “Maybe. When?” He asked.

“You know the place where the little stream bends back on itself, about a mile from here? I usually go there in the evenings. I like to….play around down there. No-one ever goes there. No-one will see.”

“Tomorrow?” He asked and his voice seemed insistent.

“Yeah, around seven?” I said. I got another thrill. If he showed up tomorrow I’d be naked and ready. Fuck I’d be ready.

“Be there waiting, then. I’ll try to come. But on your own. No-one can know because I could get into a lot of trouble....”

“I know” I interrupted him. “I won’t tell. I want it. Honest.” I said. I wanted to say something so he knew I how much I wanted it again but all I could manage was “I liked it. We’re not doing anything wrong.”

He ran his hands over me, looking and touching one last time before he got up, pulled up his pants and hurried away through the woods. I lay back, my hand down there, my fingers exploring. I could feel his cock still, almost like it was still inside me. And my hole was still not quite closed. I took hold of my dick with the other hand and jerked off, shooting more cum over me that I’d ever managed to produce before. It left me breathless.

“Man I love that tight passage. Such a fucking sweetie” my client exclaimed. I giggled for him and he lightly slapped my ass. “Hey you mind if I wash up?”

“Of course not” I said “You know where everything is, daddy.” He smiled at me. He liked it when I called him that. The trick was not to overuse the word. He disappeared, his big dick bouncing about as he walked away.

There are two types of client: those who wanted to keep hold of the moment for as long as they can, and those who shoot and go. The first type usually want to be sucked clean after. They hang around and touch and kiss and want to be touched in return. This guy was the latter. Once his balls were empty, he was finished, no longer interested. I swung between the two, but today I was okay with being screwed and abandoned. I had a late lunch date to get ready for, so it was cool.

Out of courtesy I remained where I was until he had washed his dick and dressed himself. I was his until he left and he wasn’t paying to see me get up and get dressed. He wanted to know I was well-fucked and could hardly move.

He looked handsome in his slacks and shoes and business shirt. He looked relaxed now, too. Ready for his long-haul flight. I felt I had achieved something.

He rolled me over and kissed me. I felt him slide some notes under my ass. That was unusual as this guy paid via a bank transfer. I didn’t always allow that, of course, but like I said: this guy was a regular.

“A tip” he said to my unspoken question. I raised an eyebrow. “You tell me the sweetest lies and I appreciate that. You’re the only boy I see any more and I figured I should show some appreciation.”

I made myself go misty-eyed and gave my bottom lip a wobble. I took his face in both hands and kissed him again, deeply. My emotional state might have been a well-rehearsed act, but I genuinely appreciated what he was doing here. I charged enough that men didn’t need to tip.

“Thank you so much” I enthused. You really don’t have to, you know…..” Always play it cool, but only after you said thanks. Then it’s harder to take back.

He pushed me away and smiled broadly at me. “Enjoy the money. I’ll be thinking about you constantly, until next time.” He said. He kissed my forehead and got up to leave. “Thanks. You look after yourself kid. See you soon.”

“Your PA will text me with a time?” I called after him as he strode to my front door.

“Yeah, the usual. Couple of weeks I guess. Gotta get this Europe trip out of the way first.”

I nodded sagely. Yep, gotta get Europe outta the way…. He opened the door, turned back and blew me a kiss, and then he was gone. He didn’t even wait to see me catch it.

I reached back and brought the cash up. A couple of hundred. Nice. That was a damn good tip for a straightforward screw. I got up and put the money in my jar, then showered again, jerking off before I got out and got dressed. I often had to look after myself, but I didn’t mind that. It was the fucking I enjoyed.

I grabbed my keys and moved the pot plant back to where it should be. I smiled, thinking back again to the woods of my youth.

The next day had taught me everything. The guy had come back, trying to sneak into my little camp, trying to be sure I was alone. He found me naked, laying face down on a blanket I’d brought from home with my legs spread wide for him. I’ d thought about this all night and all day and I was overjoyed when I realised he’d come back.

That evening he ate my ass and he sucked my cock. Those things alone were enough to turn me into jelly, but then he lay me back down and stuffed me full of his hairy dick again. It was just wonderful, all the more so now that I was naked and able to spread wide for him.

What really did it for me was when he made get on my hands and knees. He got behind me and grabbed my hips and then he really went to town. It hurt, but it was the best hurt I’d ever had. I felt used and dirty and and my hole felt hot, and these were, I swear, the best feelings I had ever experienced.

I sucked him clean. He didn’t ask me to, I just did it because I wanted to taste it and I was till feeling as horny as hell. He came down my throat and he asked me to dribble it out of my mouth and down myself. I obliged, of course. He really liked that. I liked it too: it felt slutty.

He gave me a twenty after we’d finished. “If you keep your mouth shut, we can do that and you can earn a little. How does that sound?”

I sucked him off again for that. Twenty....? And fucking....? Oh my!

He fingered my wet hole before he eventually came again and this time I swallowed it down.

We met like that once or twice a week for a few months. I built up quite a stash of money in that time, but it was the sex I enjoyed most. Then he just stopped turning up and I never knew why.

I glanced at my phone. Two messages. One from my friend telling which restaurant we were meeting at. The other was from a potential new client.

I smiled. This guy was unsure, hadn’t done anything like this before. I walked into the bathroom and took a photo of the jockstrap that I’ d left laying on the floor and sent it to him.

“I’m free Thursday. Tell me what time. We can fool around and if it works, that’s great. If not, that’s ok too. No pressure. It’s all cool…. But someone needs to take these off me.” I typed, adding a little winking emoji at the end.

He put a little heart on the photo. There was a pause and then he replied. “Ok. Around 3pm? Does it have to be an exact time? I can get off work early before I go home.”

“Somewhere near 3pm is great” I typed and I added a heart, too. I sent my address in another text message. Then I sent a third: “Come though, won’t you? I’m excited to meet you now. I promise we’ll have fun!”

Another pause. Then a smiley.

I grinned. I loved breaking in a new client. But that would be for another day....