How I Learned to Love My Hole

By Stu Hadley

Published on Oct 21, 2022

Gay

How I learned to stop worrying and love my hole Tan's 3rd letter


Tan gets intimately `acquainted' with some of his new colleagues and finds out why sucking cock is so important to the development of his hole.

Themes include cock worship, cock sucking and masturbation. Average reading time: about 10-15 minutes.


Okay, where was I? Just being led onto the foundry floor, dressed in painfully revealing and skin tight overalls, a huge plug wedged in my near cherry hole, and all topped off with a fresh load of cum drying on my face.

Speaking of loads, that last cock that interrupted my letter writing is a stark reminder of just what I've got myself in for. My mouth is always on-demand and part of the best employment loyalty scheme you can ever imagine? Who wouldn't stay around if you had access to this kind of service. Take this burly guy, he looked like he could get physical work anywhere. But here he could whip out his thick man meat (before I barely knew it, a slug of his precum spraying across my face) and rape a mouth as if he was possessed. His hands held the sides of my head, his dick thrusting in and out of my throat. I was gagging, I was choking and yet I fucking loved it. So much girth that it filled my entire mouth. Balls so heavy and low-hanging that they painfully slapped my chin. A load so thick that it completely clogged my throat. Every ounce of cum in his balls drained out.

Or at least what I thought was every ounce. He pulled out and shot two more streams across my face, one for each cheekbone. A fresh splash of man seed on each. This morning I would have wiped it away. This evening it was just what I needed, to be kept in my place. Besides, I like the smell of fresh jizz.

Anyway, I'm getting ahead of myself. Cutler gave me a full tour of the foundry, and I got to see sparks flying, cranes moving, machines colliding and steel being poured. It was all very hot, intense, dangerous, though I felt none of the exhibition was really for my benefit. In fact, I felt I was being shown off, not around.

I lost count of how many guys I was introduced to with knowing looks. My overalls did their work and I felt nothing more than an object on display. The stares ranged from big bears and daddies to jocks with muscles hard from laborious work. Everyone was grimy with sweat running down their faces. Rough as fuck, men with no time to shave. In comparison, I felt pristine. In fact, I felt imposter syndrome from wearing overalls as dirty as theirs that I didn't deserve. And deeply self-conscious from my brazen junk and the waddle in my ass. I was a marked man and I couldn't help but notice how many guys had the same style of sailor front zip as Cutler did. Not one had an arse zipper like mine though.

Slowly - after what seemed an age - I was taken to where I am now. The accountancy department almost felt at home, even if I was no longer dressed for it. However, this is an environment I'm used to and I almost felt happy being introduced to everyone. I saw a spare desk and thought that was where I'd be working but Cutler said no. I was led to a place at the back, a storeroom full of chemicals, industrial solvents, filing cabinets and row upon row of dusty boxes, papers spilling out of every one. I was told my job was to find the right docket, invoice or receipt and file it in the right cabinet. Jesus. Was this what I paid my accountancy exams for?

Cutler asked if I was all set? I nodded, this wasn't exactly going to be taxing work. Boring and repetitive, but not demanding. He reached for the door and said he'd pick me up at 7. Oh, and to not forget rule two. With that he left.

At the time, I wondered why he'd said that - maybe just reinforcing the morning's lesson? - but as I write this it's all become clear. Back then I was still surveying the scene though. There were dusty wooden shelves overflowing with all sorts of documents, some of them dating back decades, none of them in any kind of order. Still, I'm methodical and I was determined to make a start. Maybe work would help me stop thinking about the bung in my hole?

That's when the first man arrived. My first real job of the day.

`You the new cocksucker?' he announced before I realised he was even there. The sound shocked me as he hadn't entered through the finance room, evidently there must be a door directly from here to the factory floor.

Gobsmacked, I nodded. `Good, come here and suck this' he said, pulling down his crotch flap. His outfit was navy blue and had the same style of crotch zip as Cutler's. The logic behind the design finally made sense as his cock unfurled in one easy, swift motion. Evidently the higher-ups go commando. I guess he was in his late 40s with a grizzled face that showed a hard life, but his smooth shaft was as hard as a teenagers.

Remembering rule 2, I got down on my knees to suck. Never refuse a cock. As I went down on him I couldn't help but feel my mind wandering though. This was my second cock of the day and it wasn't even 11 o'clock yet. Was this my life from now on? And what exactly did this have to do with training my hole? Oh, and could I find a cushion as my knees were seriously hurting?

As my thoughts turned over, I noticed the grey hairs in this man's pubes and tuned in to hear him saying how his wife wouldn't go down on him and how lucky he was to be first in the queue as Cutler owed him a big favour.

Queue?

Sensing I was distracted, he ordered me to keep my hands behind my back and hold my head perfectly steady. He then proceeded to fuck my mouth as if I wasn't even there. I swear he kept his eyes closed the entire time. As he got more into it he gripped my head tight, his bunny thrusts getting harder and harder. I could tell he was lost in his own world and thinking about what he couldn't get at home. `Take it Sheila, drain my balls bitch, swallow my load.' I grunted in reply to each of his strokes, pretending I really was Sheila and taking it against my will. That totally took him over the edge and he painted my tonsils with his seed. He really was a shooter.

Sheila doesn't know what she's missing.

Jim - that was his name - pulled his dick out of my mouth and went back to form, a polite man in his late 40s. He did his pouch up, thanked me and left, saying he'd no doubt see me again very soon.

After that, the barrage of cocks kept on coming. My new role was running a service train. I soon worked out that a fresh dick would arrive every half hour or so, giving me about 15 minutes between each one (depending on how fast they shot) and a lot of time to think about how quickly and dramatically my life had changed. All in the course of a weekend.

I couldn't believe it. Last week I was an accounting clerk with prospects, now I seem to be nothing more than a cum dump. A throat receptacle for sperm. I thank god at least that the overalls were padlocked as some of these guys obviously wanted to fuck me and I couldn't cope with that right now.

As I sucked I think I went through the full cycle of grief. Blaming Cutler. Getting angry. Mainly blaming myself though. For being horny and thinking with my dick. Watching too much porn and cursing my freakishly thick cock. Resenting everyone who had warped my mind enough to make me think I was only good enough to be fucked.

In the 8 hours before Cutler returned I took 15 cocks in all, 16 if you count the one I've just blown. No wonder my jaw hurts so much. They were all shapes and sizes, and attached to men of all types. Gay, straight, bi. White, Asian, Afro-American, Latin. I think I must have sucked the entire pride flag. Some dicks were thin, some fat. Some rank, some fresh. Loads were quick to arrive or took forever. Some watery, some rich and thick All I knew was that I had to keep on going... howeverI couldn't stop from comparing each dick to Cutler's massive piece. None of them came close to the impact he's had on me. So far... As the day went on I prided myself on doing a better and better job. Some guys wanted me to swallow or pull out and shoot across my face, but one thing was consistent. That it was good to see me, that it was a shame the last guy had `gotten worn out so fast'. I didn't - couldn't - believe that. Surely there can't be an asylum for retired porn performers or service whores? No one needs to be hooked up to a fuck machine for 20 hours a day unless they go crazy. That has to just be a joke, right?


As promised, Cutler came back around 7, his pristine overalls now dirty and sweaty. Despite all the men I'd serviced today he was still my vision of masculinity and I was immediately drawn to his massive basket. I'm that hungry for his meat. Apparently that wasn't on the menu though.

He asked me how my day had gone and I obviously had my own questions, not least why I needed to suck so much cock if it was my hole that needed training?

For starters, he said I needed to earn a living. Acme Steel works doesn't need another file clerk, that was just a cover story for the IRS. My real duties were employee servicing. In every way possible, starting with turning me out as a champion cocksucker. To do a good job on absolutely every single dick that came my way.

That's when he said I was obviously a natural, that he'd been hearing good reviews all day long, apparently the entire factory was buzzing. I blushed - if you could see that under the spunk glaze - and he leaned in and kissed me.

I was worried he'd recoil in disgust as I felt nothing more than an animal. I certainly smelt like one. Just what had become of me? And yet somehow I was proud. The layers of spunk on my face were evidence of what I'd had to endure. The earliest loads crusty, but most kept moist from constant and heavy replenishment.

Cutler though? He wasn't phased by it at all. His lips felt so good, like I was wanted and cherished, not just a service whore. As he licked my face I knew just how many factory loads he must be tasting. Somehow he was showing that whatever I'd done he'd been there before? Or he could take whatever he was expecting me to take? As I write this I'm honestly confused.

Anyway, he then pulled me up from the floor - wait, I wasn't going to get to suck him off? - and told me I was coming home with him. In fact, that's where I'm finishing this letter. The factory has emptied, the whistle has sounded, and I'm done for the day.


His place is seriously nice, way, way better than the hovel I was renting before. It's huge, open plan and filled with light.

He showed me around, not least his massive bedroom with a king sized bed. I asked where I would be sleeping and he said with him. Can I possibly explain how that made me feel? I'd taken 16 loads (no, 17 if we include the receptionist) and yet I still wanted more. I wanted to be as close to him as possible.

After the tour he told me it was time to get clean, leading me to a huge bathroom with a shower clearly built for two. He undid the padlocks and asked me to strip. God it felt good to roll those sweaty overalls off, even if getting them past my junk again was tough. I knew the secret now. He then told me to present and bend over so he could retrieve the plug. Damn, I'd almost forgotten it was there. Almost.

He gently eased it out, its exit way smoother than when it went in this morning. I guess it must have done good work? I still didn't get to see it though, I was simply allowed to go to the toilet whilst Cutler left the room. Once done I expected to be plugged again, not least as I felt empty, as if something was missing. I called out that I was ready.

`Ready for what?' he said, standing in the doorway.

My jaw dropped. He was completely naked. This was the first time I'd seen him in all his glory and man, was it a sight. It wasn't so much the size of his muscles - big as they were - but their firmness. The way his veins stood in stark relief. Nor just how hung he was, though I couldn't deny how awesome the size and shape of his dick was. It was the energy inside. Knowing what he wants to do to me. It's intoxicating.

`Ready for the next size' I gulped.

`Not so fast, we're going to take it steady. Cycles of stretching and relaxing make for a more resilient hole. I have you for a full year after all.'

(Fuck, 52 weeks, that's 260 working days at 16 cocks a day? That's over 4,000 loads!)

We entered the shower together and I got to do something I hope to get very familiar with. Washing and worshipping Cutler's body. It took a long time as there's so much of him. His muscles are superb but so is his dick. It stayed flaccid the entire time and I was amazed at just how heavy it is. He has so much self-control compared to my own wayward meat. I rose hard during our wash-off and I was desperate to unload. I sensed that wasn't to be though.

I was right. He turned the water off and we dried ourselves down. Cutler then grabbed a white terry cloth gown from the back of the bathroom door and slipped it on. I asked whether there was one for me.

`No. That's rule number 3. In this house, you will be naked at all times. The only exceptions will be when I specifically give you clothes to wear.'

WTF. I couldn't parade around the house naked all day and night! Even if this place was secluded.

His raised eyebrows were all it took for me to be quiet. I was learning fast (and my nipples were still angry from this morning, even after the hot water) so I knew not to argue.

Cutler told me it was so I could get comfortable with my body, to take pride in my cock and balls, to not be ashamed of it. If I learned to live with my dick then I could learn to take big dick. It was that simple.

However, that didn't stop me from feeling super self-conscious as we sat down for dinner. I guess that was the point but that still didn't explain why I'm expected to suck so much dick...

After eating, we moved to the living room, sitting opposite each other on comfortable leather chairs. Cutler said he'd tell me why, but only if I played with myself at the same time.

`You want me to wank in front of you?' I asked.

`Yup. I want you to be totally comfortable with your body' he replied. 'What's more, you're going to cum on my command. I know you're busting a gut to unload after the day you've just had. Don't lie to me boy, I can see your dick rising already. And if you don't cum, I won't let you shoot for a week. Don't think a chastity cage can't be made to fit your big meat.'

I have to admit this was pretty hot and I relished putting on a show for my man. I grabbed my shaft and quickly got myself to full hardness. That's when he started talking.

`I know you want to be fucked by a choad as big as your own. I know you want your hole to be stretched so big you can take it with ease. Loose and sloppy, just the way I like them. By the end of this year, there ain't going to be nothing you can't take. I know the thought scares and excites you, I can see it from how hard your dick is, but there's no backing out now. I've got you for a full year and you can be sure my horsecock is going to plough your hole into the ground to help stretch you out. It's going to be a lot of hard work, but it's going to be worth it... so worth it.

To get there, I need you to start thinking about dick differently - don't shoot now boy, there's still more to come! - I know you like cocksucking, christ, others would complain after a day like yours.Not you... but liking dick isn't enough. I want you to love it. To need it. To be dedicated to pleasing cock. By the end of the year I want you so hungry for dick that'll you do anything to get it. Hold it boy... almost, almost...

So hungry that you won't be able to live without it. We'll condition you to check out every cock you see, on every man you meet. Especially on a street or in a crowd, your head desperately trying to determine which cock is most deserving to serve. The correct answer, by the way, is all of them.

Your hunger will be so strong that if you're denied cock for long enough you'll go crazy. You'll do anything to get it. Epic dildo-riding sessions to distract yourself. Mammoth cunt stretching scenes until you're left permanently gaping. Your hole is never going to be the same again: big is never going to be big enough. I swear by the end you'll do anything to prove how worthy you are for dick. You're not going to feel alive unless you've got a cock or fist inside you. Now, shoot!'

FUUUUCCCCCCK! My dick erupted with cum! I had been on the edge for so fucking long and I couldn't have held out any longer. I felt like my entire body was orgasming as fat ropes of spunk endlessly pulsed out my balls. Christ, it was the best orgasm of my life. It was all just a fantasy though, right? He couldn't mean it? And if it was true then surely I wouldn't have been turned on so much?

Looking at the splatters of cum on the floor, Cutler said I wasn't going to let that go to waste, right? Embarrassed, I looked over to see he had that wolfish grin on his face again. I knew that look well enough. I licked my spunk off the floor, finished writing this letter and then joined him in his bedroom. It was time for me to show him just what I've learnt today...

Tan


Comments and suggestions are very welcome at stuhadley77@gmail.com For more of my stories, please check Nifty's prolific author page :)

Next: Chapter 4


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