How I learned to stop worrying and love my hole Tan's 1st letter
An inexperienced big-dicked bottom learns to love himself... but only once he learns what his hole is truly capable of. Follow his descent and eventual ascent through sucking, fucking, fisting and lots of gear. Expect big cocks, big holes and big hands.
This chapter introduces the two main characters and centres around cocksucking and assfucking in a dive bar. Average reading time: 20 minutes.
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Hey, how's it going? My name is Tan and I'm nineteen. Five ten with a smooth swimmer's build and hair that turns blonde in the sun. Christ, it sounds like I'm writing a Tinder profile. I'm honestly not but Cutler has made it explicitly clear: write it how it is. That I have well developed pecs with big nips, a taut stomach and a fat prick that always, always shows.
Why would I reveal this to a bunch of complete internet strangers? Because Cutler wants to turn my fantasy - of being a completely degraded ffuckhole - into reality. Or is it his fantasy?
Damn, I'm getting ahead of myself. Let me start by explaining how all of this kicked off. For a while I've been over the vibe of the mainstream gay bars - the queens and the rumour merchants - yet its taken me an age to build up the confidence to try a different scene.
Last night, I finally crossed that bridge.
Oil Can Harry's is miles downtown and in an area way worse than I was expecting. Pawn shops and porn, basically. As I walked past the street hustlers and pushers I was glad of the long-sleeve tee I was wearing, somehow it made me feel less of a target. My jeans though? Had I made a mistake? Sure, they made the most of my butt but I have a lot to hide down there.
A surly bouncer let me in and I immediately found the noise and heat overwhelming. The hustle of heaving half-naked bodies, leather men in boots and harnesses, guys in sportswear with their cocks out on the dance floor? It was seriously intimidating and I almost did a complete 180, but I'd come this far and I couldn't back out now. Maybe I should've.
I jostled my way to the bar, rolling my sleeves up to try and fit in. That didn't mean I got any service though. I took in the view, feeling faintly ridiculous. How could I approach any of the men here? Did I even find them attractive?
That's when he appeared.
I'll be honest, I don't know what he saw in me - maybe my innocence? - but he announced his presence with a resounding slap on my arse. Shocked and startled, I turned around to find myself looking up at a tall man with a wolfish grin. He was a lot to take in and I felt my pulse race. Even in this crowd he had a body and face to stand out. His skin glistened with sweat, a shine that perfectly accentuated his broad shoulders and arms that bulged with muscles. He was wearing a worn out shredder vest, made taut by the size of his chest. Dark curly hairs spread out underneath, rising up to meet a thick growth of stubble that was crowned by a dense moustache.
It all looked so natural and effortless, exuding confidence from every pore. And that hand on my arse? It was still there. Cupping my cheek as if he was staking a claim. He scanned my face - seeing I wasn't going to complain - and his grin travelled to his eyes. He nodded at the bar keep and in seconds a round was in front of us.
He held up a shot of tequila and I was challenged. Was I up for this? I licked some salt and downed the harsh alcohol, feeling strangely at a distance. Was this really happening? But then he caught me off guard, squeezing a wedge of lime into his mouth and planting his lips on mine. Fuck! The sharp juice cut through my thoughts and all I could feel was his kiss and his big body pressing against mine. For such a big guy he was sensuous - such a damn good kisser - but cruelly urgent. I couldn't hold back and my crotch started to get uncomfortably tight.
Fuck. Why had I worn such tight jeans? As his hands roamed over my body I knew exactly why. It was because I'd wanted to show off my best assets - my butt - however, as he wandered towards my crotch I couldn't change things now. He was going to find it, and soon enough he did. He recoiled in shock, or was it delight? Was I for real? he asked. I am, I blushed, I most definitely am.
Without asking for permission, he led me to the dark rooms at the far end of the club to see for himself, his hand holding mine so I couldn't draw back. The scent of the dance floor - sweat and liquor - passed to a darker world of poppers, ass and cum. However, I was only paying attention to just how fucking broad his back was and how good his butt looked in his tight leather jeans. The single red handkerchief sticking out his back pocket was dangerous yet alluring, and even in the darkness I couldn't help but notice his jeans must have been custom made. Not just to fit so well, but also as there was no left pocket. Just one on his active side.
Hey, I may be nineteen, but the internet can teach you a lot!
By now we were surrounded by fornication and fellatio at every turn but he kept on walking. My mind was running at full speed. The sight of a guy on his knees sucking dick embarrassed rather than turned me on. What if the man leading me on doesn't like mine? Just like all the guys who had taunted me in the locker room? The beatings from my step-father to keep my unnatural junk hidden away? The queens who had shrieked and said they could never take `that'? I wanted to run but his grip got even tighter.
He led me to a quiet corner that was out of sight and reasonably hidden - evidently he'd been here before - and kissed me again. I felt the universe closing down and I forgot my fears. That's when he said he had - needed - to take a look. Sure, he'd felt me up but now it was time to see it for real. Soon my jeans were half down my legs and his reaction wasn't what I expected at all.
`Jee-sus! What a choad! Christ, how the fuck do you live with that much girth?'
He was simultaneously holding, groping and staring. I get it, I've always been hung, freakishly hung. On two goose egg sized balls sits an uncut cock the exact size and shape of a Coke can. Literally. It's the bane of my life - the object of ridicule and jealousy. It barely changes shape or size, flaccid or erect, just firmer. That's 2.5" thick and just under 5" long, I kid you not. A stubby shaft riddled with pencil thick veins and ending with an outrageously flared helmet and extremely wide piss-lips.
He had got to the heart of the matter though. I don't know how to live with this appendage. My size means I doubt I'm ever going to get properly sucked and certainly never get to fuck. Till now, anyone who's seen my dick either runs away or insists my future is only as a bottom. I honestly think it has warped my mind.
That meant his reaction was actually a relief. I couldn't believe how much tension I'd been holding in and it felt so good to let it out. This was the first time someone had actually appreciated my dick for what it was. Huge. He continued to squeeze and touch, seemingly fascinated and keeping up a running commentary that was only making me swell. `This must be a one in a million dick. I've never seen fatter. Christ, you could model a dildo right now. I bet all the hole-stretching queens are all over you...'
Yeah, if only.
His attention was making me seriously horny. This was why I was here, to meet a guy with enough experience to swallow at least some of my dick. The few guys I'd hooked up with had been so scared of my cock I'd always ended being the cocksucker myself. I desperately wanted to change that, to feel a hot mouth around my own, but that wasn't to be on the cards.
I couldn't help it, my thoughts turned to thinking about what he was packing. Under the shredder, under the leather, under the muscles... what did he have? I tried to wipe the darkest thoughts from my mind, surely I couldn't be that perverse--
-but that's when he opened his fly and hauled out his own meat. He had a nice fat basket and I was immediately, stunningly jealous. Half-flaccid and growing in his hands, his dick was fucking perfect! A long and thick shaft - in perfect proportion to his muscular body - smooth, uncut and his helmet still hooded. It was a cock of beauty, not a freak of nature like mine.
Even though I'd wanted his lips around my dick, my natural, innate instincts kicked in. I needed his cock and he knew it. In seconds he'd pushed me down to my knees, a place I was glad to be.
Up close I was staggered at just how hung he was. The size of his massive frame disguised it well because he was wrist thick and almost forearm long. He was now fully hard and I moved in, wanting to taste the clear nectar welling at its tip before it was wasted and dropped to the floor. He told me no, that I was to bury my face in his balls and start licking first. He'd been going commando and his leathers had obviously kept his sweat in. The smell of his manhood was soon filling my nostrils and I felt intoxicated and slightly dizzy.
I gently pulled his sack out to give me the full suite of options and was stunned at how heavy his bull nuts were. They must have been packed full of cum. Taking a risk, I kept one hand on his balls, the other on the base of his shaft and let my tongue slowly move up his shaft. He didn't seem to mind - not if his moans were any indication - and my mouth was soon at the tip. Christ, I must have been a foot away from his balls! How can any human being have a dick this fucking long and thick?
`That's it boy. Keep going. Peel my foreskin back and savour the flavour. I pack a lot under the hood and I want you to get it all.'
This was like nothing I'd even done before. I should have felt disgusted by the dickcheese but it turned me on even more. When his helmet was drenched in my salvia he said enough was enough and it was time to get my pussy mouth fully on his dick.
I know. Pussy mouth? Maybe I need to be treated more this way.
I opened as wide as I possibly could and did my best to take it all, however, his awesome size made me hesitate. Sensing my indecision, he grabbed the back of my head to steady it and slowly pushed himself forward.
`See how easy my horsecock slides down your throat? Fits nice and snug, doesn't it, cocksucker?'
As I felt his fat shaft fill my mouth his words drove me on, even though by my reckoning I was completely stuffed and he wasn't even a third of the way in. I tried to pull back but he took complete control, slowly starting to do the work himself. Long, leisurely strokes in and out, going deeper each time. And holding himself inside for longer too. Soon I was desperately clinging onto his leather-clad thighs, gagging and struggling for breath. At the end of one particularly challenging stroke he pulled all the way out, released his hands from my head and told me to look up. There was that wolfish grin again. `Going to have to work on your cocksucking skills until you can throat this fucker without gagging, boy... get back on it. Time for you to work my load out.'
I took his cock back in my mouth, determined to make him shoot. I cupped his massive balls whilst furiously licking and sucking as much of his massive cock as I possibly could. He buried as much as he could inside my throat and I found it impossible to take a breath. His dick was fully filling my passage, not allowing room for air to get in. I could feel myself getting light headed as I gulped and gasped trying to get oxygen to my lungs. All he could say was how amazing it felt, like I was milking his meat.
Soon he was climbing the heights of an impending orgasm, grabbing my skull to pull me forcefully onto his dick and driving as much as he could into my throat. He said he was getting close, that he hadn't cummed in three days so this was going to be a gusher, that I wasn't to dare stop now. I felt his cock pulsating and I worked even harder. Suddenly his hands were back on my head and ropes of cum were filling my mouth. `Swallow it all kid! Don't miss a fucking drop.'
Christ, he wasn't lying about it being a big load! I struggled to keep up with the firehose in my mouth but I think I just about managed. Thank god I like the taste of spunk but this thick cum was like nothing else I'd ever experienced. I swear I could taste the potency.
He slowly withdrew, pausing for me to polish the tip. He then pulled his leathers open as far as he could before pushing his still turgid cock back inside. I noticed he didn't even try and hide it, and I envied that confidence. When you've got a foot of hard dripping meat in your pants there is no way to cover it up, so why try? He finished buttoning his fly and then pulled me up from the floor.
`You did good, boy. Let's get another drink'.
My own cock painfully unrelieved, I struggled to do up my jeans, feeling incredibly badly packaged and self-conscious as we went back to the bar. Both of us looked disheveled but me more than most. I could feel a damp patch spreading across my crotch - I've always been a big leaker - and I bet it could be seen by anyone who looked.
Back at the counter - another round in front of us - he introduced himself. Said his name was Culter and that I obviously have a passion for dick. After that performance I couldn't deny it. Ever been fucked, he casually asked. I kinda nodded, it was strictly true but I have some problems down there. He paused and asked whether I wanted to fuck?
I obviously misunderstood his question as he laughed at my reply. I said I'd like to, but I'd never met a guy who could take my size. He shook his head and said with all seriousness that I wasn't a top. After all, if I was a real top then I would have demanded to be sucked off, not start drooling at the thought of blowing him. He was smiling but there was steel behind his eyes. Not wanting to answer, I downed the shot in front of me.
`Besides, you're too embarrassed by that meatloaf you're packing. Not like me, I own my cock. You know, I bet what you really want is to be fucked by a dick just as thick as yours. Or bigger. What a head fuck that would be?' He leaned incredibly close towards me, the tip of his tongue suddenly darting into my ear. My entire body shivered with pleasure before he whispered to ask whether his guess was right.
Oh fuck, this was a slippery slope. I felt like a queer caught in the barracks and I couldn't turn away.
`Good. Let's fuck' he answered for both of us.
He must have seen my alarm but he completely misread it. `Oh don't worry about me boy, my balls reload in seconds. I'm ready to go again already.' That wasn't what worried me though. There was no way I could get fucked by him, not here, not now. It wasn't that I didn't want to, it's just that I'm super tight. The one or two times a guy has tried to fuck me had been super painful, and they'd been regular cocks, not a plough horse like him. Besides, how trashed would my hole have to be to take his girth? Or mine for that matter?! Did I really want that?
`Talk to me, don't clam up, not when you're so close.' A sternness in his voice I hadn't heard before.
I told him I was tight and lacked experience. I wanted it, I just couldn't take it. He sailed past that, just hooking onto that I was open to being fucked and for taking more. He said he could help me with that - that he was something of a specialist in this area and I was totally safe with him.
Fuck. That should have been a warning signal.
We railroaded another shot and he doubled down. Said my hesitancy meant it was even more important for him to have a test run to find out the severity of the situation. He was confident I could take him, I just had to trust myself.
Drunk on cum and tequila, horny from his attention and my dick painfully unrelieved, I stupidly thought what the hell. When else would I get such a perfect opportunity again?
He led me back to the dark rooms, no hands this time, just the occasional look to beckon me on. In that moment he was so fucking powerful. He had muscles but he didn't need to use them. Just his sultry smile and the call of his dick.
I was expecting to return to our previous spot but this time he stopped at the sling hanging at the apex of the maze. It was empty - a break in the proceedings I guess - and he guided me in. It all felt so surreal. If I wasn't so drunk there was no way I could have done it. I had to undress, my rigid cock betraying my desire, and then lay back. The feel of leather was unfamiliar yet reassuring at the same time, although my wrists and ankles being threaded through some hanging loops freaked me out. I felt trapped and on display but he simply told me to relax. That it would all be fine.
He then got on his knees to inspect my arse. My rigid pole is so thick that I actually had to look around it to see his face. That worried me as I could see how concerned he looked. He was holding my cheeks wide and staring intently. `Christ, you're right. Your hole is as tightly puckered as a balloon knot. I've never seen a hole so tight. Are you sure you're not cherry?'
I was embarrassed but there was no point denying it, he'd find out soon enough. I nodded and he did a half-wolf. So much more tension released from my body. He then did something no one has ever done to me before. He put his face between my arse cheeks and licked my hole. He started slowly but as I relaxed I swore I could feel his tongue working his way inside of me. Christ, it felt so fucking good that I didn't want it to end. Even the feel of his stubble drove me wild. Between mouthfuls he said he loved eating out a hole, making a pussy wet for a nice long fuck.
Those words kinda scared me but I had no time to think as things suddenly changed and I asked what he was doing. It didn't feel right anymore.
`I'm just trying to open your hole to see what I've got to work with.'
I realised he'd worked a finger from each hand inside of me and was pulling me apart. I winced, leaning forward in confusion and pain. He shook his head in dismay but then his demeanour changed. He withdrew and told me to stay put. Like I could go anywhere? His back retreated into the darkness and I couldn't help but feel lost. Was it over?
Long moments later he returned with a tall and lithe black guy. The man was older than Cutler and totally naked except for a blue jock that was threadbare and badly stretched. Glances were exchanged - from my arse and back again - and there were nods of acceptance. The black guy spoke: 'Yeah, he'll do. But only if I fuck bare, you know I don't get wrapped up.'
Wait, no way! This guy had been bought over to fuck me? And raw? Fuck no!
Culter turned to me, telling me we needed to do this. That there was no way my hole could take his big prick the way it was now. That was a fact. But Marcus was a `special' friend that could lay the groundwork. In fact, given the state of my hole, I was actually lucky to be fucked by him.
Writing this in the cold light of the morning, I still can't believe this has happened. To say I was scared is an understatement - I was right to be. I tried to escape but Culter held me steady as Marcus pulled off his jock. Fuck! Even half soft, his was the longest and thinnest cock I've ever seen in my life. He must have to tuck it between his sack and back towards his crack every day. Maybe I'm not the only one with dick problems?
By now crowds had started to gather, as if they knew a big show was coming up. Marcus's dick hardened without him even touching it and words spun in my ear again. How this guy was famous for having an arrow shaped cockhead that meant no hole had ever denied him entry. I looked over and it was true. His helmet was honest to god pointed, turning his cock into a spear. A spear for opening guys up.
I found out later that his nickname is Holesplitter. That's exactly what he did. Split my tight arse in two, all whilst being watched. Marcus grabbed some grease (though not too much, he wanted me to feel it) and lined himself up. He then pressed his cockhead against my hole and pushed. The pressure was gentle at first and I thought I could resist but I'd never experienced a cock so hard or so V-shaped. Christ, I felt fire in my hole! I tried to complain but that wasn't going to stop him. Culter even stuffed his jock in my mouth to keep me quiet whilst he kept on boring down.
When my hole finally relented and let him in, the crowd cheered. I felt strangely proud even though I'd never felt such pain before. His rock hard shaft now took full advantage to plough further in. I couldn't believe it when he got balls deep - I had finally been fucked! Maybe there was hope for me after all.
I hate to say it, but all that pain soon turned to pleasure. His long, thin cock had obviously found its home. Just like I'd been told it would. He kept telling me how much he loved the feeling of my tight pussy wrapped around his dick, how the friction was turning him on. That couldn't be true, right?
Soon he was slamming in with deep hard strokes that took the air right out of me. Culter half-heartedly tried to calm him down, but Marcus took it in his stride, saying he'd been asked to open me up and that was exactly what he was doing. I can remember thinking that the sooner I made this guy cum the better and I instinctively gripped my arse muscles and didn't let go. Soon enough I could see his face change and with one final thrust he dropped his load. Thank god. He pulled out at the same time as Culter removed the jock from my mouth (along with a good slug of saliva) and told me I was a good pig. Pig?
Fuck. I can't believe I've just written that? Pig? What am I becoming?
Culter then announced it was his turn. By now his dick was standing proud of his open fly again and it looked no less impressive, no less scary. Could I really take a cock so big, even after Marcus opened me up? Without him attempting it I could feel that my newly inaugurated fuck-chute was seriously tender.
My thoughts were broken by a cry of amazement. Culter was looking at my hole and muttering that I looked just as tight as before. That by any rights Marcus's load should be freely leaking out of me right now. In disbelief, he leaned forward to push a finger inside. Damn, that hurt! He said he didn't fucking believe it. That my hole had squeezed so tightly shut that all of Marcus's slime must be trapped deep in my guts. That meant there was no natural lube to slick the path of his giant cock, that I must have the kind of hole that snapbacks after every fuck. He said it was going to take a serious amount of dick - each fuck as painful as the first - for my ring to be stretched wide and sloppy enough to take a cock his size.
Dejected, his cock deflated in front of my eyes and he packed it away in his jeans. I tried to get him to give it a go, but he wasn't having it. He simply helped me get down as the crowds dispersed, disappointed to not see the fuck they'd expected. Just one more crushing failure to think about.
I got dressed and found Culter sitting at the bar. It was the very fag end of the night and the only guys left were the desperate and needy, scanning the room and ready to make bad choices. I know how they felt.
He handed me another shot, by now I'd lost count. Crestfallen, he said that I was right, that I'd likely never have a hole big enough to be fucked by a dick my size. Or his. It was obvious I didn't want it. He shouldn't have even tried.
I begged him to try again. I'd had such a hot night with him that I wanted to feel this again, to lick and suck his cock again. And I desperately wanted him to fuck me.
He shook his head, saying I had no idea just how much work it would be. That I didn't have the commitment.
Of course, as I'm writing this, you know I persuaded him. Or he persuaded me? He'd lit a fire inside of me and I told him I'd do anything to take his dick with ease.
Deep down, I knew my darkest truth. That if there was a bottom out there that could take a cock my size then I wouldn't be a freak.
And if I were the bottom - if my hole was big enough to take my mammoth girth - then I could prove it could be done. Then I could stand tall and proud. I could be myself.
Yeah, I know. it's fucked up.
The rest of the night is a bit hazy but I remember him brightening up at my acceptance considerably. That I was lucky he was looking for a new project. That he liked helping guys like me. Giving back to the community. All I had to do was follow his instructions to the letter. Something about stretching, plugging and modifying my body to attract the right kind of guys?
I do remember the subject of fisting coming up and how it could help prepare me for cock. I said taking a fist was a big no-no, but he counted by saying I was so tight that without an intervention I'd be at least 30 before I could be fucked with ease. Is that what I wanted?
Fuck. 30? That's a lifetime away! I think I drunkenly shook my head at the enormity of it all whilst saying I couldn't wait that long. And maybe if I wanted a big hole I simply had to accept my fate?
`You'd have to let me help you though, come live and work for me. The first rule is following my instructions without question.'
Yet another shot and we left the bar. The cold night air should have woken me up, but it just made me cling to Cutler's heat. Deep down I knew this was all wrong - it couldn't possibly be true - but I was swept away.
The alarm bells should have really sounded when we walked into a 24 hour notary and bailiff - it was that kind of neighbourhood - and the man behind the desk (his friend, apparently) had a contract on hand. I heard the terms but I didn't hear them. So high on the idea and so unrelieved of cum that I couldn't help but sign it, an illicit thrill running through my entire body, especially when he told me to simply trust him. That only he knows what's best.
What the fuck have I let myself in for?
Why am I even writing this letter? It's all part of the deal. Culter will look after me, provide for me, service me for a year. He guarantees that by the end my hole will be big enough to take a dick as big as my own with ease. All in exchange for working at his factory and writing these missives. I can't say I'm happy about that. I'm a junior accountant with good prospects but working in the finance division for Acme Steel Works is a dead end job. An industry on its way out, and at a company that has a seriously bad reputation.
My hole is still painful from Marcus's arrow shaped dick and I swear I can still feel his cum sloshing about inside of me. Is this what my life is going to be? And the fisting? That has to be a joke, right? `Degraded fuckhole' can't possibly be a legal term, can it? And yet...
This is going to be interesting.
Tan
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