How I learned to stop worrying and love my hole Tan's 7th letter
Our boy Tan finally gets fucked by his master.
Themes include exhibitionism, fucking, dildos, porn and chastity. Average reading time: 15 minutes.
Shit guys, Cutler doesn't know how to remove my giant steel cuff either. Looks like I'm stuck with 2" of heavy metal stretching my balls for a while longer - he says he's asked around the factory but no-one's owned up. Surely someone must know who made it and has the key? My balls already look angry and purple. Any longer and the guys say they might drop off. That has to be a joke, right?
All the guys seem to love it though. It gives them something to grab onto - a hitching post if you will - and they really go for it. It's made everyone more aggressive. The downside is I swear its making my sack hang lower - I can't remember the bottom of my nuts ever hanging below the end of my dick before.
Of course, that's not been the only change to my body. Since I last wrote I've been back to Mike's to get my piercings stretched. Everything has gone up a size: my nose, nipples and my PA. My dick is definitely heavier but I have no idea just how big they're planning to get. Cutler was given a preview - the piercer showing him the progressively larger rings he's had custom made - but they're being kept a secret from me. Dicks.
Meanwhile, the sucking and dumphole duties are going ahead at pace. Its relentless and means I think about sex all the time. Not least as my extra curricular activities and training have all stepped up a gear. Cutler makes for an excellent PT and his home set-up is brilliant. My muscles have been getting bigger for months but he says I still have so much further to go if my body is going to be in proportion to my dick. Thick. He says that's the only way to attract guys who will want to fuck such a freak of nature as me.
However... the first time I tried cardio with my steel cuff was impossible. Remember, I have to be naked at all times in Cutler's house and the damn thing bounced up and down in time with my sack. It was fucking agonising and obvious that even with the best will in the world I couldn't complete a full workout.
Cutler told me to stay put and then came back with a complicated item of leather strapping - like a jockstrap on steroids. A close fitting pouch that holds my junk and the cuff firm to my body, connected to braces that go over my shoulders and down my back. He tightened the straps so my body took the weight of my balls and suddenly I could run on a treadmill again. I can't say it's easy, but at least it's possible.
Who has that type of gear lying around in their house though? Just standing by for a big nutted boy to wander by? It does make me wonder.
However, the nut slinger isn't the only item of clothing I'm now allowed to wear. Cutler has started taking me to bars and clubs at the weekends, including the place where we first met, Oil Can Harry's. It feels strange to be back and now looking the part.
My body is still small compared to his - I imagine I always will be - but now I have enough muscles to properly wear a shredder vest too. Actually, it's more of a crop top, one that shows off my firm abs and clearly outlines my swollen and pierced nips. Of course, my tops aren't plain like his. Mine have a vintage look, with slogans and logos like:
Kept Boy' Always Open' Load me up' Park Here' `Deep Hole National Park'
Oh, and they're also so threadbare as to be almost non-existent. One wash and I bet they'll disintegrate. Each is totally on the wrong side of innocence but they certainly seem to turn Cutler and his friends on. I've lost count of the number of times we've been out and he's gotten hard. Of course, he's not embarrassed by his big schlong, he just tells me to sink to my knees and hide his boner in my mouth.
He also seems to take great pride in loaning me out, showing off just how great my cocksucking skills are. Often his friends bet I won't be able to get them to shoot inside of a set time but I know all the tricks by now. I always win. And I always want the cum.
I guess so many guys come on to me because I look totally available. Below the crop top I wear a pair of denim shorts that's been made to Cutler's special requirements. They're honestly remarkable.
First, how low-rise the cut is. Any lower and you'd be able to see the root of my dick! As it is, the belt line is pulled down by the sheer weight of my junk and the massive steel cuff, meaning anyone looking can easily see the tiny, one inch thin trimmed patch of bush I've been allowed to keep.
(Did I not mention that? Cutler's started shaving me. I was sad to see my pubes go as it only makes my mule cock look even bigger but I can't complain...)
Being Culter, the low-rise isn't my only problem. The shorts are virtually hot pants, so high-rise on the thigh that the head of my dick is in constant danger of falling out of the leg holes. It's only how tight the fabric is that keeps me and my PA in.
Second, the design of the crotch. It's been tailored to give me just enough room for everything but there's no fly or zip.
No, the front perfectly contours to the shape of my junk without a break in the fabric, meaning everything I have is thrust forward into sharp relief (nuts, helmet, metal and all). Packing myself in is a nightmare and several times a night I get asked whether I'm for real as I look so unnaturally big.
Thirdly, how worn and thin the denim around my junk is. The fabric is so thin that I swear the dark tube of my cock flesh shows right through, but it's also so white and worn down that it makes it look like I can't stop stroking myself.
Finally, the zip that runs right up my crevice and gives easy access to any man who wants to tap my ass. To make things even easier, there are two straps of thick, red elastic attached to my outer thighs. They have big, U-shaped hooks at the end that can be used to pull apart my denim clad cheeks, revealing my bubble butt in all its glory.
I don't think you'd believe just how much dick this has allowed me to take, or how the queues line up to tap my ass. What worries me more is how Cutler invariably slides a finger into my hole at the end of a long night and I turn into a complete sluice gate. Cum drains out of me like I'm a one dollar whore. Surely being this loose isn't healthy?
Of course, the real change is how my love and need for anal stimulation is only growing. I feel a constant itch and emptiness in my arse if I'm not being used. Is that normal?
I have no idea whether this is cause or effect. I do know it's no longer enough to just be fucked and have my body trained though. Dildo-riding sessions are now planned into my daily schedule.
It doesn't matter how many cocks I've taken at work (or how many I'll take when going out) Cutler wants to keep my hole fully occupied. He has me fucking my pussy for a minimum of 90 minutes a night, even after a heavy shift.
Before now I honestly didn't know that dildos came in such an extreme array of shapes and sizes (and new ones seem to arrive every week). I'm getting to appreciate them all though and how different they are from real cocks. Hard flared ridges. Thick veins. Fantasy animal shapes... Most of them really work my prostate and I end up oozing pre non-stop and making me always on the edge. This means I have to be really careful as rule 5 (not cumming without permission) always applies.
Sometimes Cutler fucks me with the toys himself, catching me by surprise and at my most vulnerable. An oversized rubber dildo protruding from my hole and then a giant hand coming crashing down on the base with extreme force. It forces the toy into my body and makes me gasp, all before he grabs the dildo and starts ploughing it in and out,
At the end of each training session he inspects my hole and claims I'm making good progress. Apparently I'm beginning to look like a pussy with thick ass lips that always bloom. However, all this time, he reminds me to keep my hole control up too. Strengthening the muscles to stay nicely tight. Aren't these two goals counter-intuitive?
Of course, this all begs the question of when I'll be fucked by him. I've taken so much cock recently I feel like I'm hanging on a cliff edge! Right now I'm on some weird sensory deprivation routine. I'm not allowed to watch any TV unless its a gay sex scenes. Or allowed online unless viewing the most hardcore fuck and suck scenes you can possibly imagine. My only reading material is twisted erotica that describes situations that can't possibly be believed. This means sex is constantly on my mind. Always.
He has me describing how I imagine the cock of every guy we meet looks. In addition - to keep me on edge - he makes me write long essays on dick sucking and ass fucking techniques. And insanely detailed porn reviews. He's even made me write a thesis proposing what his cock will feel like the first time it breaches the walls of my cunt.
This is unbearable. I now count myself as something of a dick expert and I can confidently say none of the factory workers come close to the thought of his foot long pole.
All the anal penetration, oral action and porn consumption has made me seriously hungry for Culter. Last night my perverted sex dependency broke me. We were getting ready for bed and I couldn't hold out any longer.
He'd stripped off his clothes and it was a sight that reminded me once again why he commands my every move. His body is so broad and muscular, dense hair covering him from stubble `tache down to his pecs and treasure trail. A trail that ends in the most magnificent dick I've ever seen. When humanity ends, history should be remembered by how handsome, thick and hung Cutler's penis is. Right now it was soft and swollen, gratefully arcing over his low hanging-sack and on total display.
It's like he's built to breed. A breeding I really needed.
Seeing him hang free made me so desperately horny that my flaccid cock started dripping pre on the floor. He noticed (of course) and asked what was up.
Please fuck me,' I begged. I've wanted to feel you inside of me for so long. I swear my hole is ready. Please, please, fuck me'
The most curious thing happened as I talked. My cock rose out of its slumber and I became painfully hard. The act of begging for his dick seriously turned me on. I have no idea what that makes me. Desperate? Submissive?
There's a good boy, that's the sign I've been waiting for' he replied, wolf-like. I knew if I didn't force it on you'd beg for it eventually. That's the secret to being a good pussy, following your most basic human needs. The time has come.'
My eyes must have gone blazingly wide. He was finally going to fuck me?
He laid back on the bed, spread-eagled and with his cock standing upright like a fucking fence pole. He told me to mount it, to show him just how much I wanted it.
His helmet was oozing a healthy stream of pre-fuck, nature's best lubricant. Still, I wasn't going to take any chances and I grabbed some lube from the bedside table. I greased his fuck slab, the heat and hardness hot in my hands. As I stroked, his thickly skinned hood pulled down, revealing his helmet in all its glory.
I straddled his body and lowered myself down. Soon the tip of his dick was touching my arse and I had a moment of self-doubt. For all my `warm-up' fucks (Akiro, the men on the line) his helmet felt like a blunt instrument against my hole. This was going to be a challenge.
I pressed my hips down whilst wiggling my ass in a slight semi-circular motion. His cock is so big that there was a surprising amount of resistance but soon my sphincter yielded and the huge head of Cutler's cock popped inside. It felt agonising but I was determined to show him I could take it all in one. I took a few more breaths and then forced myself down his girth, sinking down inch by long painful inch. Going balls deep felt almost impossible...
Of course, I relaxed and opened up, just like I've been taught. But really it was Cutler's encouragement that carried me through. Relax your pussy, he said. Push it out for me, take my cockhead... loosen up those cuntlips.
His use of the `c' word triggered me. Like I was no longer a man but simply an aperture for another man's pleasure: Culter's. My mind leaped to a fantasy life of sexual servitude and it immediately did the trick, allowing me to sink right to his hilt. I've never felt so full in my entire life.
Good boy' he said, eyes twinkling. You were born to ride my dick. Now fuck the cum out of me.'
That was all the cue I needed and I rode that pole for all it was worth! I started slow (out of necessity - I still had to adjust to his mammoth impalement - but soon I was able to clench down and send ripples of pleasure through both of us. I was determined to prove that I wasn't just a fuckhole, that I could milk his cock like no other man. I saw his pleasure and my strokes got faster, a good thing too as my legs were honestly getting tired. No amount of gym squats prepared me for this workout.
As I internally massaged his dick I could tell he was getting ready to shoot. Me too. I hadn't touched my cock but I was hard and desperate to fire. It was like all my wanks and wet dreams had been building up to this one singular moment, this one moment in time. Riding this dick of destiny. Sensing my need (or my pain?), his breath fastened and he told me I had permission to cum.
FUCK! As he blasted my guts he created a chain reaction that meant I shot hands free, great ropes of my spunk firing over his hairy chest. Christ, it was the longest sustained and most intense orgasm of my entire life. And all because of the hottest top I can possibly imagine.
Elated, I rose off his dick with a squelch. I knew I had one important job left. Without being told, I cleaned Cutler's cock with my tongue and then licked my spunk-splashes off his body. I don't think I'll ever get tired of this shit!
Absolutely sated, I fell into bed alongside him to be his spoon for the night again. Big arms holding me tight, comforting me. And more importantly, I fell asleep with his load inside my arse for the very first time. Despite everything that was to happen, I still know a really important milestone has been broken.
I woke up in the morning with a hole that could still feel the imprint of his fuckslab, a massive grin on my face and a burning desire to visit the bathroom. Gently rolling away from Cutler, I left the bed and replayed the events of the night in my head. How I'd ridden his massive dick and how that surely meant I was now ready to take a freak cock as thick as my own.
The thought made my obscenely fat prick well and I couldn't hold back from wanking. I knew I was breaking a house rule but I was so excited I couldn't help myself. More fool me! Cutler must have a sixth sense as he burst into the bathroom and caught me right in the act.
Of course, I'm now totally fucked. He didn't shout or scream but his fury was quiet and all the more dangerous for it.
`How can you ruin it now, boy? Stop groping yourself and get!'
Chastised, my dick softening, I obediently followed.
He led me to a door I'd always thought was a closet, so unassuming I've never tried to open it. He pressed a thumb on a discrete panel that's the same colour as the wall. It must be a fingerprint scanner as the door smoothly unlocked and swung open.
I was overwhelmed by the dark space beyond, not least by the intense smell of leather and rubber that emanated from within. Cutler said it was his play space, a space he says I'm now going to become intimately familiar with. He beckoned me inside and I tried to take it all in. The sling, bench, chair. Walls adorned with hoods, mitts, straps, harnesses, whips, chains, paddles. Racks of dildos even bigger than the ones I've already taken.
Christ, I'm sure I'm missing stuff out. I've honestly never seen so much gear in my life, not even in the continuous porn films I'm forced to watch. Why should I be surprised though? Cutler's apartment is deluxe - a man of sophistication - why shouldn't his sex dungeon be any less considered?
He swept his arms across the room. `I have everything to make your life very painful. Or give you extreme pleasure... but that's for later, much later. Now it's time for your punishment.'
I can't deny it. I know I shouldn't but the thought of intense sex made my dick twitch. I wanted all of this. But not this...
He reached into a cabinet and pulled out a steel contraption the likes of which I've never seen. Hey, I'm only 19! He threw it into my hands and I was stunned by its weight and the quality of construction. And it's evil purpose. I know as I'm wearing it now.
Cutler explained it all. How this cold, hard metal was designed to keep everything in order. That he'd had it custom made to fit my oversized junk after reading my last letter (damn!). A thick hinged ring that fits snug around my cock and balls. It's connected to a long tube of steel that contains my flaccid cock. At its end? A urethral plug that replaces my Prince Albert and locks everything together. The perfect chastity cage. Apparently.
There is no way I can wank now. Or even get hard. The steel tube is studded with internal pressure spikes that can be individually extended or retracted at Cutler's exclusive command, making even the mere thought of an erection painful.
I tried to protest that this SERIOUSLY wasn't necessary. He explained it away, saying it was time I learned my hole was my primary sex organ. As it all clicked into place he said this kind of device has been proven to be an effective way of permanently turning any pussy boy like me into a total cock-hole whore.
Cutler's whim is now my only hope of release. I'm fucked and I can't possibly write any more.
Tan
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