The Journey From Chastity To Cuckold
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A Soldier's Journey Through Chastity — Chapter 2 free porn video
When I woke up that Saturday morning, I made a bowl of cereal and opened up Grindr. The moment I did, I was yet again bombarded with messages and taps from several different guys who were clearly all soldiers. Half of the guys that messaged me sent dick pics (of course), and the other half acted like they just wanted to chat. Yeah, right.
Well, I figured I'd change my display name and make my profile picture a little more enticing. I took a picture I was certain wouldn't set off the mods, one mostly just showing off my surprisingly big ass, clothes in a jockstrap. I made my new display name "need keyholder" and left it at that.
My bio read something along the lines of, "I'm looking for an experienced keyholder/master to help guide me through chastity since I'm brand new to it. Serious, professional messages only. We can get dirty when I trust you more."
I sat and waited, and after a few minutes, I got a message. I opened the app up again and to my surprise, I think I may have found exactly what I was looking for. A real man's man, twenty-eight years old, six-foot-two, broad shoulders, chiseled muscles, tan skin, and oddly enough, his hair was greying prematurely— something I found quite attractive actually.
His message read as follows, and I quote:
"Hello. My name is Michael, I'm actually only a specialist and this is my first duty station too, since I just got out of AIT. I see you're looking for a master or a keyholder, and given my experience in BDSM, I think I can be both for you. I understand if you don't want any pictures yet, but I am quite hung if it matters to you. You'd be the third person I've helped guide through chastity, but I have the sneaking suspicion you might be the most memorable. May I ask your name and what limits you have in regards to BDSM?"
Well, Michael here seemed serious enough, so I figured I'd give it him a chance. I couldn't lie, I was curious to see what he was packing, but all in due time.
"Hey Michael, my name is Kai. Thank you for responding to my request. I'm actually pretty vanilla, and my biggest overall limit is bondage. I just can't do it. If that's a deal-breaker, I'm sorry for wasting your time, but that's the one thing I cannot compromise for both of our sakes. And while I would love to see what you have, I like the mystery of not knowing all the better. If you'd like to talk on a more stable platform, here's my Kakao."
I sent him a QR code of my Kakao account so he could message me. In Korea, given the KATUSAs (Koreans Augmented to US Army) used it so much, nearly all of the soldiers used KakaoTalk too.
Within a few moments, I had gotten a ping on Kakao and opened it up. "Hey Kai, it's Michael. I'm glad you're as interested as I am. And don't worry, bondage isn't for everyone and it's certainly not a deal-breaker. If you'd like to meet up, I'll be at the Dong-Jong-Ri gate at 1800, and we can walk down to a wonderful KBBQ place. Sound good?"
"Absolutely! You've made a good impression, so I'll see you there," I responded. I set my phone down, letting out a deep sigh, shaking my head. 'What am I getting in to?'
"Good. Bring all of your keys, or no deal. Your first step into this new world is to trust me. Answer with 'yes or no, sir.' If you choose to say 'no, sir,' explain yourself."
Woah. That was unbelievably forward, and my heart was suddenly pounding like a drum in my chest. I was unsure what to respond with, since I had my emergency in a locked box and a limited supply of plastic number locks. I texted back, "No, sir. I can't bring both keys. One is in a lockbox with a numbered lock, and that's for emergencies only. Do you want a pic?"
There was no response for a few minutes, and for every second that went by, my heart would beat harder and harder, and my prick would begin to swell inside of its prison. The anticipation was killing me, and I had no idea if I had just ruined my opportunity at finding the perfect first keyholder.
At last, my prayers were answered, and he said, "Yes. Send a pic now of the box and your cage. Tick tock." I jumped up from my recliner and bolted to my desk to snap a quick photo of the lockbox and sent it. Shit! The cage!! I held up my junk by the balls, my open palm supporting the hefty weight of my titanium dick and took the picture, sending it as fast as I could.
"You have good taste," he said simply, followed by, "My first pet had the same one. Titanium-gold, right? Good luck getting out of it. I'll see you at the gate. Don't forget your wallet/CAC. Gtg."
Whew… what a rush… I set down my floor, laying naked once more on my recliner, panting, trying to calm down my throbbing heart. I had no guarantees he'd even try to have sex on the first date, but honestly, I wasn't opposed to it after the thrill he'd given me in just the first few minutes of meeting him.
At around 1600, I started getting ready, first by making sure I was clean-shaven, both on my face, and down below, crotch and pucker. After I washed away the shorn hairs and got out of the shower, I combed my hair up and put a light amount of modeling mud to give it a shape I found appealing.
I made sure to brush my teeth again for good measure, and picked out a fresh pair of near-new dark blue jeans, my favorite belt— a real leather belt adorned with three rows of steel pyramid studs— along with a nice blue polo shirt to compliment the pants. Just simple black tennis shoes, something practical in case I ever needed to run. I grabbed my rather fat wallet and stuffed it in my pocket.
I took a brief look at my Zippo, wondering if I should take it. It was the 2018 lighter of the year, the Golden Scroll. Real gold plating and beautiful ornamental engraving. It served well as both a lighter, and something to fidget with when my nerves grew out of control (although admittedly the ping could be quite annoying after a while to many people). I figured there was no harm and pocketed it, then grabbed my loose key and went out the door, waiting on a cab to pass by. Once my ride was secure, I just simply said, "Walk out gate," and the older Korean gentleman started the meter and began rolling.
It must've been a good five-minute ride from the 6000s barracks to the gate, and it cost 11000 won. Not much, really. Once I paid him, I got out, and saw Michael standing there, leaning against a pillar by the gate, grinning. He looked down at his watch, and I realized it he wore it the same way I did, with the face on the inside of the wrist.
"You have impeccable timing, pet. Come on, let's go. I've had a change of plans. I'm sure you've had enough of Korean barbecue, so how do you feel about Brazilian food? I know the perfect place."
"That sounds wonderful, sir," I said honestly. My stomach didn't care what kind of food it was fed, so long as it wasn't cottage cheese or something rotten and moldy.
"Excellent. By the way, I can see the outline of a lighter in your pocket, do you smoke?" What an odd combination of observation and inquiry…
"Well, no, sir, not strictly. I had a pack of cigarettes once in AIT, but I haven't really smoked since, and I don't ever breathe it in." I wasn't exactly opposed to smoking, even though I knew it was unhealthy. When you're an air traffic controller, sometimes things can get mind-numbingly stressful, so I understand why Sergeant Hopel and Staff Sergeant Olmen took so many smoke breaks (they were the most experienced controllers).
"Good, because there's a cigar place right above the restaurant, Miki-O's place. He mostly sells Davidoffs so it's a bit expensive, but I've got you covered since you're new to it."
"Th-thank you, sir," I said meekly as we walked out the revolving gate. We took a right turn, walked for a bit, then went left. April in South Korea was still a bit cold at night, and I was regretting not bringing my jacket. Michael noticed rather quickly when I shivered, and pulled off his coat, resting it on my shoulders as we walked. "S-sir, uh… thanks."
"Don't worry about. Next time, bring a coat, yeah?" I nodded, and he patted my shoulder. "Cutie." Well… forward as always. We might end up having sex sooner rather than later… We finally got to the restaurant, and took the elevator to the second floor to get to it. Once we were seated and had ordered our food, he leaned forward, weaving his fingers together, eyeing me like a predator. "Now… I trust you brought your key as ordered, yes?"
"Yes, sir."
"Give it to me," he demanded. No asking. No pleading. No formalities… and it immediately made my cock swell with blood and warmth inside the cage. I reached into my right pocket and pulled out the key, hesitantly setting it down on the table and sliding it to him, my hand still on top of it. He raised a brow somewhat impatiently, and I quickly retracted my right hand, leaving the key behind. "Good boy." God, it made me nearly shudder to hear him say that while we were in a public place, the kitchen not being that far from our table.
"Now, I want to explain something to you. First off, the safeword is… Zippo. Any time you say that word out of context, I will assume you are uncomfortable with what is happening, and I will immediately stop, and we'll talk over it, see if we can compromise or work around it. I encourage you to be as flexible as you possibly can, and to please, please try to endure what is to come. I won't lie, it'll be difficult, especially as time wears on, but I have confidence that you can do anything you put your mind to. So, I will ask you this: what is your ultimate fantasy when it comes to chastity, and what is your end goal for our relationship?"
My heart sank, and I had to take deep, focused breaths to keep myself calm. This was a lot to take in at once… safeword… endurance… fantasies…? I heaved a big sigh, and looked up at him, blinking a few times. Good God, my erection was coming back at full strength as I thought about my deepest fantasies…
"W-well, sir… I uh… I often fantasize about, uh… b-being locked up permanently… e-even though I know it's super dangerous and not something that should be tried lightly, I… I can't stop myself from thinking about it. It's been on my mind ever since I put on this, that arousing sort of fear that I could hand my key over to someone and never see it again, be trapped in this cage forever, and… well… I like to think I'd be just fine with that, but I really don't know for sure. I've only had a prostate orgasm like… once, and I gotta say, as awesome as it feels, it's not satisfying, as in I felt like I had to keep making it happen, and I still didn't feel truly satisfied until I jacked off."
I took a pause, another deep breath, thinking deeply. "Alright," he said with a soft, warm smile. "I definitely can understand why you fantasize about such things, and rest assured… I can help you orgasm, caged and hands-free, given enough time to learn the ins and outs of your body. Now. What's your goal?"
"Oh, right," I huffed. "My goal… my goal… uh… my goal, honestly, is not just to have a master and a keyholder, but someone to love. A boyfriend, too. A real, genuine, loving relationship, with a bit of extra spice to the sexual side of it."
"Ya know… that's fair, Kai," he said softly. "I've always believed the only way you can be truly invested in another person's pleasure is if you're willing to sacrifice your own. I've sacrificed enough in my lifetime, but… I want you to prove to me how dedicated you are to building a relationship with me. It's painfully obvious how attracted you are to me, just going off how much you're blushing."
'I'm blushing? Oh God… I'm such a cheese ball, giving myself away like that… this is soooo cliche…'
"So, when we're done with our dinner and cigars, I'd like to take you home with me. Make you mine. Be warned, though: You will most likely not experience any sort of climax, not without the right tools, of which I don't plan to use tonight. How does that sound?"
"I… I would very much like that, sir."
"Good. And look, our food is here. You ordered the lamb, no?" The servers carted out platters of kebabs, and before long we began to dig in.
We made various idle conversation, talking about our interests, seeing what we had in common and such. I found out he actually was in the same unit as me, but worked down in base ops, while I was up in the tower. He and I shared an appreciation for thrash metal as well as jazz and swing, and for a brief period, obsessed over guns. Big bad Texas boy, what could I do but admit my interest in firearms?
After about forty-five minutes into dinner, we were finished. He insisted that he would pay, causing me to get all flustered, feeling like I was being babied. "Don't worry about it, my pet. You don't make quite as much as I do, and since I left a kid behind with his mother, I'm also getting separation pay."
"W-wait… you have a kid?" I asked in surprise.
"Indeed I do, little Buck… not the name I would've chosen but whatever. Mothers… it was an out of wedlock sort of deal. I knocked up my girlfriend and after the baby was born she dumped me and now we have dual custody. She's taking care of him for now while I'm in Korea, but she's planning to give me full custody so she can focus on going to school full time."
"Oh… I'm sorry if it's a touchy subject," I said in a soft, somewhat embarrassed tone.
"Don't be. I figured you ought to know. It's part of that whole 'trust' thing, get it? Anyway. Come on, up the stairs. I said I was going to introduce you to cigars. It'll help your food settle and make you feel more relaxed."
He led me up the stairs to the cigar shop, and inside I was rather surprised at how cozy it felt. There was a propane-powered space heater in the center of the room, a minibar, and plenty of sofas and armchairs to lounge in. "Hey, Mik. Lemme get two doubles of Vat 69, and uh… I'm introducing him to cigars. We'll take the table over in the corner."
He then stepped into the glass humidor whilst Miki set up our table with an ashtray, clippers and a torch lighter. I followed Michael in the humidor and wowed at the massive selection. Yet, my soon to be master already had two sticks picked out, and gently pushed me along out of the box.
"Okee, two Churchill Late Hour… two double Vat 69… okee..." Miki said in his rather thick accent, punching in the numbers onto the register calculator. "100,000 won." Yikes… a hundred bucks for two cigars and some booze? Was Michael really going out of his way to make sure I got the best smoke possible? He pulled out a hundred thousand won bill like he already had known what it would cost, which was quite uncanny indeed.
After he paid, we went to sit down on the couch, and he wrapped one arm around me, hugging me close. I couldn't deny… it felt nice to be so close to someone. "Go ahead and open them, pet," he said softly, and I began fumbling with the cellophane wrappers, eventually succeeding in pulling the rather large cigars out of their packaging. "Alright, see right here, on this end?" He said, speaking in a calm voice as he pointed to the rounded end of the cigar. "That itty bitty, nearly invisible line, is the cap of the cigar. When you cut it, you want to cut it right on that line, or maybe a little bit higher, so you don't have to worry about it unraveling. Go ahead."
Hands trembling, I picked up the guillotine clipper, and closed one eye to line it up, aiming carefully. "Sharp, quick pressure. Go on." I slammed my fingers together, and with a snip! the cap was gone. "Not bad! That one'll be yours. Go ahead and cut mine, baby." I did as he said, cutting at the exact same spot as before, and he flashed his teeth, opening his jaws so I could stick the stogie between his teeth. "Right, now, here comes the most important part. I personally prefer to light my cigars with a match, but a butane torch is just as good. Never light it with a Zippo, you'll taint the flavor. Got it?" I nodded, mumbling a little yes sir, and he smiled. "Good."
He reached into his jacket chest pocket, the same jacket I was still borrowing, and grabbed a small box of 30 matches. "Watch and do as I do." He struck two together, and held the flame to the other end of the cigar, gently puffing, taking his arm off of me to rotate it 180 degrees, then kept at it, turning it little by little to give it a nice, even, toasty burn. He waved the matches out, tossing them on the ashtray, and handed me the matchbox. "Go ahead. Try."
I took out two matches, just as he did, and while holding my cigar in my mouth with my dominant, left hand, I struck the matches and brought them to the end of the cigar… little by little, just as he did, puff and a turn, puff and a turn… satisfied, I blew out the matches and placed them on the ashtray next to his burnt-out ones. "I must say," he mused, "you seem to be a much more gentle fellow than I, despite your zeal." Meekly, I nodded, smiling sheepishly as I really started to draw on my stogie.
I got hints of walnuts, scotch and vanilla, not at all unpleasant. I took a sip of my glass of whiskey, nodding, letting out a little "Hmm…"
"What is it?" he asked calmly.
"Well, sir… it's a rather relaxing experience… a-and… having you so close to me is also really nice…" To that, he wrapped his arm around me again, smiling proudly.
"Good. I'll warn you, in about thirty minutes you're probably going to feel light-headed from the nicotine and alcohol— mostly the nicotine. If you start to feel nauseous, get some water, take a break. I'll make sure your cigar doesn't start to burn unevenly. Last thing I want you doing is getting sick on me. By the way…" he ended that last bit with a pause. Odd. "Are you a virgin, little one?"
"Yes, sir." I lied. I had to lie. It just wasn't the right time, and besides… even after that I still basically was a virgin… right?
Michael raised a brow, eyeing me carefully, but shrugged. "Well, that's alright. Means I can give you all sorts of new experiences tonight, aside from just cigars…" I nodded along with him in agreement. This would be a night I wasn't soon to forget.
As I continued puffing on my cigar, time wore on, and all that Michael and I did was sit, cuddle, and blow out smoke. Honestly… it was wonderful, just having him hold me. After a while of smoking and drinking with him, I started to feel a bit dizzy, like the room was spinning, and I blinked slowly. I was nearly finished with my cigar, though, and had already taken off the labels. "You okay there, little guy?" Michael chuckled. "You look like a bit out of it." I nodded, trying to shake off the feeling of nicotine sickness, and managed to pull myself up, letting out a deep sigh.
"You wanna get outta here, bud?" Again, I nodded, and he grinned. "Splendid. Lemme walk you to the gate and we'll get a cab. You'll be staying at my place tonight."
"Mmf… okay," I said drowsily, standing up with him, using him to support my weight when I nearly fell over from getting up too fast. He didn't seem to mind.
The period from when we left the cigar bar to when we got to his room is a blur from there, but I do remember him kissing me quite thoroughly in the back of the cab. Poor taxi driver probably was not prepared to see that…
The next thing I knew, I was naked, laying on his bed, which was surprisingly large compared to mine. Later he explained that he managed to snag a room with one of the last double beds.
He whistled loud and long and low, evidently pleased with what he was seeing. "Good God, babe, you are adorable… look at you," he said, holding up my balls and caged cock in his palm. "Such a cute little package… and so drippy… I'm impressed."
He lay down in front of me, his head between my legs… and through the slit and side holes of the cage, he started pushing his tongue, teasing me, oh so cruelly tormenting me, making me arch my back as I whimpered in desperation. He began to chuckle, and then started gently suckling on my plump nuts, swollen full of seed I'd never get to spill. "Look at you… so drippy… pent up… aching to be let out… do you want to be let out, pet?"
I started to moan and nod my head fervently, and with that, he clicked his tongue, shaking his head. "Oh, no, no, no, we can't have that… you know better. You've been locked up for all of, what, a day? And you already want to be let out of your cage? Silly boy…" Michael climbed up on top of me, holding himself up, staring down at me like a hungry predator. "Forget about it. Locking yourself up is the smartest thing you ever did." To that, I let out a whimpering mewl, grinding up against him, already beginning to shed a tear.
He wiped it up, and just shook his head, still holding a smile. "Now… turn over for me." I did as I was told, laying on my belly now, ass up as I assumed he'd want, face in the pillows.
"Ever tried poppers before, pet?" I shook my head no. Poppers? What on earth those were, I had no idea. "Alright… well… this'll help you relax and make things easier for both of us. I'm going to put it up to your nose, and I want you to inhale nice and deep, one nostril at a time. Ready?" I nodded and lifted my body up, getting on all fours. He put the little vial up to my left nostril, and I took a big, deep whiff of what smelled like alcohol.
Next was the right nostril, and almost immediately, my face felt hot and flushed, and I collapsed forward, already feeling dizzy again. "Easy buddy… easy…" Everything felt so hot… it was like being drunk, sorta… I have no idea how to describe it.
Then he started lining himself up. I don't even remember him lubing up, but I assumed he must've if he was getting ready to get started. Ever so slowly he pushed forward, and my eyes went wide, my jaw fell open. My god was he thick… and as he kept pushing forward, it was like his cock never ended, endless inch after inch jamming its way into me… god, I felt so full! My old dildo never felt as big as the monster that was now throbbing inside of me, and Michael began to chuckle like a hungry beast that had caught his prey at last… and I was the rabbit in his paws.
"You're so fucking tight, even with the poppers… you really must be a virgin…"
He didn't say anything else after that, to my memory. He started to pull his hips back, then pushed back forward, pulled back, pushed forward, rocking to and fro, steadily increasing his pace and thrusting strength, and all the while, I found myself moaning out like the little bitch I am, my face pressed against the headboard, as if the dick was just too good, as if my body couldn't handle how amazing it felt to have him stuffed inside me…
He kept going harder, faster, over and over again, endlessly breeding me, no mercy at all. Each and every time he'd bottom out, I could feel him throbbing against my prostate. All of these new sensations were things I'd never felt before. It all felt too great to hold it in, and I began to scream out. Loud enough that he felt the need to shove my face in the pillows as he went to town on me so as to not risk waking up his roommate.
At last, with one final snort, it was over. He pistoned his hips forward one last time, grunting and panting, and I felt a sticky warmth beginning to flood my insides. Without a doubt, he was blowing a load deep in me. After a few minutes of panting and trying to catch his breath, he at last pulled out, smacking my ass for good measure before reaching into his nightstand. I felt something small but thick shoved into my abused little hole, and he grunted.
"There. You're gonna sleep with that plug in. Now… come here, little one." He turned me over and pulled me against his chest, throwing an arm over me, letting out a sigh. "Gonna need to keep you," he declared.
As we lay quiet for several minutes, one question kept burning in my mind. At last, I gained the courage to speak up. "Sir?"
"Yes, pet?" he answered after a brief silence.
"Have you ever measured how big you are? Down there I mean?"
"Yes, actually… little one, I'm actually quite impressed you were able to handle ten inches, especially when this was your first time… you certainly were clenching unbelievably tight… probably why I came so quickly. Rest assured I'll last a lot longer most times." That last bit had me a bit worried. I felt like I was going to explode with how rough he'd been, and there was no way that was his full strength… now I imagined having to endure even more, for longer periods of time… "Don't worry, pet. We'll work you up to it. Go to sleep now."
I didn't dare disobey him, not so long as he had my key. So I closed my eyes, and with my energy all but gone, I quickly drifted off without another peep.
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