The Canadian correspondent who wrote me about his week in chastity, has now followed up with this piece about his first meeting with the Master who required it of him.
I’m Squeaker and was given that nickname when I joined the BDSM community in Vancouver ages ago. Wearing leather and rubber became more and more my lifestyle choice (apart from clothes for my day job) and friends can tell I’m approaching by the squeaking sound my gear makes. That’s always satisfying, and I love the way skin-tight black gear looks on my body. My Viking looks, the bald head, red beard and copious amount of body hair that poke out of my garments give me a certain look folks admire. I also possess piercing blue eyes, have a “winning” smile and a laugh that’s quite infectious in a crowd.
But course I don’t just wear fetish clothes for the looks or the compliments. I wear black leather (or rubber) as a badge of honour, as black is a well-known power colour. Being a Leo I crave attention and also need to satisfy my deep sexual needs. The only problem is that I’m more passive than I look. That makes it easy to mistake me for a Sir when secretly I yearn for a domineering husky top to take me home, bind me tight, and have his way with me for hours (or days) on end. I crave being used and abused and owned by anyone who’d care to take me in, so long as I don’t receive any permanent marks (my only stipulation).
Last year I visited Montreal for the first time and found a great leather bar on Ste. Catherine street. Being a newbie made me attract plenty of attention from the locals. One rugged, tall, lean man dressed in head-to-toe leather complete with knee-high boots came over to me. He saw right through me and immediately chatted me up. “So, Boy, you’re from back West?” he growled. I told him I’d just arrived and was at the bar for a drink and to get my bearings. “You got a place to sleep?” he asked. I told him I might stay overnight at the sauna down the street. “Fuck that, you’re coming home to my place.”
Suddenly my heart skipped a beat, I could feel his dick pulsing in his tight pants as he pressed himself close to my body. The smell of our mutual leathers and his own man-scent was intoxicating.
After that, things moved rather quickly. I tried to engage in small talk while drinking my beer, stuff about my Squeaker moniker, what I did back home, etc. He hardly talked at all and instead his eyes bore on me intently; they were hypnotising. Eventually, my babbling started to slow down. I was curious to learn more about him and asked his name.
“You haven’t earned that privilege, Boy. I’m your Sir, at least for tonight. If you behave well, I’ll tell you more about myself in the morning.” And with that he grabbed my pint and chugged down the last. Then he produced leather cuffs, grabbed my wrists, twisted my arms behind my back and put them on me.
“I’m getting us a cab, so try to look normal and we’ll be back at my place in no time,” he said.
The driver seemed to know this stranger as they chatted a little before I entered the back seat. I had to be pushed onto the seat because it was difficult to get in with my hands behind my back. The driver chuckled at my awkward predicament, something I suspected he’d seen before. My new Sir took out his back hanky and quickly stuffed it into my mouth. “That’s just to keep you in line, I don’t want the neighbours to hear you yell out once we arrive.”
The drive didn’t take long and since it was my first time in Montreal I had absolutely no idea where I was. Fortunately, I had all my gear in my backpack and my new Sir was kind enough to haul it along in our journey back to his place. After we got out of the cab, I had to climb up some very narrow, steep stairs which wasn’t very easy, being slightly drunk, hands tied behind my back, and Sir pushing me upward.
“Not a sound, boy,” growled Sir, although with my mouth stuffed with his hanky, I easily obliged.
He pushed me through to the main room of his place. The lights were already on, though dimly lit. Maybe they were candles. There didn’t seem to be much furniture, all I noticed were a couple of plants and a large bed with restraints attached to the posts. I suddenly got excited. On the other hand, I was a bit shocked to discover there was someone else in the main room — a very large, bearded and shirtless guy. Hairy and menacing, and wearing an executioner’s hood, he stood near the bed with his arms crossed.
“Right, Boy. Here are the rules. I’m going to take this gag out and you are NOT to say a word to me, other than address me as SIR. That large fellow you see over there will not be talking as he’s under my control too. However, we will be putting you through your paces, and we’ll see if you can stand the kinds of depraved things we’re planning mainly for our own pleasure. I don’t give a fuck if you cum or not. But if I’m in a good mood and order you to shoot, then do NOT hold back. You won’t get a second chance, is that clear?” I muffled yes.
He yanked the hanky out of my mouth. I asked for some water.
“How do you ask for that, Boy?” I’d forgotten the Sir part. I asked again, correctly.
“That’s better. Here you are. Now my buddy and I are going to have a little fun with you. Train you well. Right now you’re wearing way too many clothes, don’t you think, Frank?” and his accomplice, who I noticed was wearing a black jockstrap as well as the hood, nodded solemnly. “Do you think our boy here is trying to look tough with this gear? Don’t you think he needs to be put in his place?” and I heard a low chuckle from Frank who started to rub his hands together and flex his massive hairy arms.
I was shoved on the bed and my clothes were hastily stripped off me by Frank, right down to my jockstrap. “Well, at least you had the good sense to wear that,” said Sir, ripping it off. He affixed on me some massive cockring/ballsac device that instantly made my dick swell up and ache like a motherfucker.
“Excellent! Just what the doctor ordered,” chuckled Sir and Frank together, clearly a private joke. “Well boy, now that you’re dressed the way you should be, best get you comfy. Get his arms, Frank, I’ve got his legs.” They practically quartered me on the bed, restraining my hands to the bedposts above, and, spreading my legs, rope-tying my ankles to a long bar which they then attached to the lower part of the bed. I was fully spreadeagled, naked and vulnerable, and getting very turned on!
“I see your little friend between your legs likes the attention!” said Sir. My cock had grown with the excitement of me being strapped down tight. “Now where to begin. Ahh, those tasty tits of yours. They look positively virginal.” He twisted my nubs and I involuntarily yelped. “That’s pathetic. Frank, gag him with his sweaty sock, please.” Frank did what he was told and I was back to making muffled sounds again. “You’re not going to enjoy this, but I have these tit pump things and I’m going to make these little buttons of yours swell unbelievably over the next few hours.”
So saying, he lubed up my nipples and deftly clamped something tight on each of them. He then gave each device a turn which tingled pleasantly at first. My dick gave an involuntary jump. “Slap that dick, for me, Frank. It clearly thinks it’s supposed to have a good time.” And ouch! Frank did so with his bare hands. “Now let’s see how far we can go.” He gave another turn to the tit devices, and then another. Suddenly the pleasant feelings went away and pain replaced them. I started to agonize a bit. “You finding this painful Boy? Just a bit?” I nodded at least, “Good, that’s a start, fine.”
With that he left the room for what seemed like a very long time. Frank stayed behind and whispered that Sir was in the kitchen, getting set for the “main event.” Later I learned Sir was having a relaxing smoke break on the deck. Frank terrified me more than Sir, he was so enormous, with a bulging stomach that looked solid and muscular, as did his meaty arms and legs. He climbed on the bed between my spread legs and pressed down on my dick with his knee. I started to scream. He smiled broadly as he lay down and squashed me.
“Having fun with our little slaveboy, Frank? Ahh, you’re throwing your weight on him, great! Why don’t you just give him a big body bear hug, show him how we welcome strangers in Montreal.” Frank put all his body weight on me, crushing my legs, dick, chest, the tits in the pump things (and that really hurt the most!) and even his face came down on mine. He was licking my face all over like some animal tasting its prey. He licked everywhere: eyelids, ears, forehead, nose. He took out the sock gag and made me suck on his fabulously huge tongue. It was enormous and tasted very salty as it wormed its way almost down my throat.
“Let’s not get too friendly, Frank. Don’t forget, we have to show this smartass from Vancouver how boys in Montreal are supposed to behave. It’s only the right thing to do, since he doesn’t understand our ways. So, get off him, it’s time for me to have some fun.” The bed heaved as Frank rolled off me. Sir gave me a moment to recover, take a deep breath or two and let my tits feel somewhat more normal.
“Now look at you, having your way with another man without my permission. That won’t do.” Since I wasn’t gagged anymore, I tried to protest. “Boy, I’m pretty sure it’s me in charge here. If you want to see the morning light, you’ll do exactly as I say.”
Sir seemed genuinely angry, so I quickly hushed up. There was something a little threatening in his voice, and my dick liked that a lot.
“You see, I’m really a nice guy at heart, especially when I’ve got a boy like you tied up.” As he spoke his hands were tracing my legs and my sides, and flicking my tits in the suction tubes. “That cock of yours is my property tonight, and with Frank’s assistance, I’m going to get you milked properly. Would you like that, boy?” I said that yes, I thought that would be fun. “Fun? FUN? Do you hear that Frank?” They both laughed heartily.
“Okay Squeaker, when did you cum last?” I had to think hard. Two nights ago, I said. “Then that’s two hours of edging as we work those tits to two full inches. And you will NOT be released until you shoot two times tonight. Once for Frank and once for me. You’ll also eat your sticky cum stuff. Do you agree, boy?”
What choice did I have? I nodded.
“Well, boy, looks like that got your dick at attention, good, nice cut meat with a big fat head. Perfect for apple-polishing! And oh, did it just twitch?”
Sir seemed very eager to deal with my aching hard-on. First, though, he removed the tit pumps, squeezed my tits hard—I involuntarily screamed out—and gave me a full mouth kiss, swallowing up my groans as he twisted. “That’s my boy,” he said. “So if you want a good time, you’ll shut up for the next two hours!” And with that, he stuffed my mouth with my piss-soaked jockstrap, slapped my dick hard, and then replaced the tit suction pumps.
Sir gave me a very long edging session by slowly stroking my cock with something soft for less friction. He stroked with a measured pace and at times stopped for what felt like minutes. At those times Frank roughly stroked my body with his gnarled hands. My face, my legs, my sides. At times he used his fingertips, which tickled and made me squirm. Sir returned to my dick with more and more repetitive motions, slow swipes upwards, pause, flick the tip at times, repeat.
My cock was aching with pleasure like nothing I’ve ever experienced before. My tits seemed to get harder. They began to really smart in a good way. I wasn’t aware that the sensations were attached to my dick, but every twitch of pain in my tits was met with spasms of pleasure in the head of my dick when Sir was good enough to stroke my cock.
Suddenly Frank blindfolded me with my tank top, twisted like a makeshift rope and tied around my head. They worked on me together. I squirmed harder and made muffled sounds. I was beginning to ache for release, but it was clear Sir was not going to let me do that for some time.
“Well, boy, you’ve been holding out great so far, not bad for an hour’s play. Now it’s time to get serious.” And with those words, he wrapped some string or rope around my balls, and connected the ends to my big toes. “Comfy, boy?” he asked with a grin in his voice. I groaned, but he ignored that. “Let’s see those tits, they’ve been under that thing for an hour. Ooh, almost two inches big, great! Hey, Frank, got those clothes pegs handy?” And with that, he practically ripped off the tit pumps and Frank obliged with the nastiest, tightest pegs my tits ever felt. I arched my back with the new intense pain, but strangely my dick remained hard as steel.
“Excellent, you’re training satisfactorily, boy.” And with that, Sir suddenly did something unexpected. He started to tickle my feet just a little, enough for my big toes to react and kick forwards, which tugged at my balls sharply. I gave out massive moans of pleasure/pain as I arched my back again; I was writhing side to side erratically. “Ha, ha, cute! You think you can just move about to ease the pain, nice try fucker.” Suddenly the clothes pegs were removed, and my tits roared with the fresh release. “Take ‘em, Frank.” And with that, Frank climbed on the bed and worked his teeth down on them hard. He also used a lot of tongue at the same time, so it was another delicious moment of pleasure and pain. “Tasty Frank?” Frank grumbled yes.
“Vibrator time for you, boy!” I felt fingers up my pussy hole with something sloppy and cold. Sir had a toy that vibrated like hell and he applied it to my balls, my shaft and my fraenum, then cupped it with a hand over my dickhead. the intensity was far more than I was prepared for. I yelped and tried to bend my back upwards to get him off me. No such luck. “Keep trying, boy. Now let’s see how this fits you.” He pressed the toy against my hole. “Breathe deeply, boy. Suck up this thing for your Sir.” I relaxed and breathed deeply and before I could believe it, I was impaled with the massive, vibrating gizmo.
Sir pressed the device upwards against my prostate and OMG did that feel incredible. I felt like pissing and cumming at the same time. “Ahh, I think my boy likes this toy, nice! Frank, why don’t you show him what you can do with your amazing tongue?”
Frank obliged with an impressive tongue bath. He worked my head and every crevice, eyes, nose, ears, mouth, and then my chest and those swollen tits (he spent five minutes licking and sucking on those) then down my stomach, both sides. He only lightly touched my engorged dick, then swiftly worked below under my dick to my balls and to where the toy was protruding. Amazing sensations as his tongue worked alongside that thing, really making my pussy hole so sensitive. I moaned over and over.
“Okay, Frank, enough of being nice, let’s really give this Squeaker boy what he deserves.”
Sir undid the ropes attaching me to the four corners of the bed (as well as those attached to my balls). I felt a welcome relief for the chance to flex.
“Don’t get too comfy, boy.” And with that he roughly pushed me on my side, pulled my arms behind my back and tied them together. He then took my feet and folded them under me to meet my hands. I was hog-tied in no time, and raging hard.
“Now that’s the way I like my boys, totally incapacitated and at my mercy! Now let’s get those tits back in their little pump things. No gag this time, boy. I want to hear you moan, scream, laugh, whatever! And you must address me as Sir if you have to say anything at all. You understand?” I said yes SIR, of course.
Frank put the tit pumps on me and twisted them until they plumped up as big as before. At the same time, he pushed the butt toy further up my ass, using his knee. OMG I moaned so loud it made my Sir chuckle. “Very good, Frank, thanks! Let’s make this little piggy boy squeal all the way home.”
Sir returned to my dick to give it a full pumping workout using very wet lube. It felt so good to have my cock worked on again. It had become a bit soft, but got rock hard in no time. Suddenly he stopped. And then resumed for a few seconds and then abruptly stopped! He really was edging me hard now. Over and over, he repeated these actions: a few seconds on, a few seconds off — it was driving me crazy! The pain in my tits subsided every time he stroked my cock and when he stopped the pain raged through my chest again. Holy shit I was panting so hard and moaning so much. My ass was getting a lot of attention, too! I was growing delirious!
“Okay, boy, I’m taking this thing out of your ass,” and with those words, he pulled it out of me in one, swift motion. I gave a huge gasp.
“There, now let’s see how you can really take it. Your ass is still too tight boy, it needs proper training. I don’t give a crap if you cum or not, I want to really open you up, and give it to you harder. But we might have to wait for another time. You okay with that?” Like I had a choice. “I’ve still got a special treat to introduce your little hole to a little later on.” Oh, God, this sounds fabulous!
I asked my new Sir if I might be permitted to cum soon. My cock was aching so bad after almost two hours of this treatment.
“Well, boy, maybe we’ll let you blow a little steam after all. Frank, please suck off our guest. And boy, I permit you to shoot only a bit, no more! If you totally spill your seed, this whole scene is over, and you go back downtown to that sauna for the night, do you understand?”
I whimpered a “please Sir, let me cum Sir.” And with that, Frank obliged my cock with his fat, moist tongue. Jesus, it felt so good, my entire cock was in his huge mouth and his tongue extended to my tight balls too. He repeated this weird, twisting trick with his tongue along my cock head and slowly, ever so slowly, I could feel myself boil inside. “Careful boy, just a little now,” said Sir, who started to tickle my feet.
That made me go insane! I squirmed about on the bed. With my cock practically down this guy’s throat, me trying to avoid the nearly painful touch of Sir on my feet. I couldn’t get away from him. Sir played with my toes, the metatarsal and the sides, both feet at the same time but in different places. Jesus! I nearly shot my load, but not quite. Sir started to stroke my legs, reaching for the inside of my thighs, which put me close to coming again. He returned his attention to my feet. I was beginning to shake involuntarily. I finally gave a little gasp and screamed out, “No more!”
With that, I did cum, but as promised, just a little, and Frank’s mouth released my cock. At the same time Sir grabbed my tits, hard. My cock drooled some cum out. “Nice boy, not too much now.” Sir released his grip, and everything subsided. Frank rubbed my balls and taint and poked a thick finger up my hole. His other free hand caught my cum, and smeared it on my mouth and in my beard.
“Good man, Frank!”
Sir and Frank, one on either side of me, shared a steaming hot kiss right above my confined body, tongue and all for what seemed like a very long time. There were audible pleasure groans from them both. For the first time I saw the outline of Sir’s dick under his pants, saw it grow in there impressively. He rubbed it over my face before popping open his jeans. He was wearing boxers. His considerable cock poked through.
“Time to gag you properly, boy. Ready?”
He didn’t wait for an answer. He put his huge cock in my mouth, taking my breath away, while over me he and Frank continued to kiss.
Frank took charge for a brief spell. He pulled Sir away from my mouth and roughly jerked him off. His own enormous cock started to grow. I could finally relax, even if hogtied, for a few minutes, as I watched these two hot men work themselves off. Sir is an older chap, leaner and roughly shaved, while Frank is much younger, bald like me but a real bear. Both their cocks were out now, and they were manhandling each other, kissing wildly, eager to devour each other. My own dick flicked a bit watching them.
Eventually they took a break from their lovemaking and untied me. I stretched out for the first time in nearly two hours. I was told to relieve myself, to get myself some water and return in five minutes, no more. There would be consequences if I got back to my bed of pleasure/torture any later.
I found the bathroom where I flexed my tired muscles and rubbed my cock with the cock ring off to make sure everything was still working okay. There was a bottle of Scotch beside the tap, so I helped myself to a finger or two.
“If you drink my Scotch, boy, you’ll pay the price!” Sir shouted from the bedroom. But by then it was too late! I’d only drunk a little bit, but I was worried. “It’s time to get your ass back here if you know what’s good for you, boy!”
I scampered back and flopped on the bed. Sir smelled my breath. “Jeez! How much of that did you drink? Frank, wouldn’t you say our little guest here needs to be taught a lesson about pilfering booze when I didn’t offer it?” Frank nodded.
They tied my hands over my head to the bedposts and pulled my legs up and over my head, tying my ankles to the bedposts, too. “That looks nice, doesn’t it? Ass open for our pleasure.”
“See this?” Sir was holding a huge metal curved device with smooth, bulbous ends. It looked like a large letter C, and made me nervous. “It’s going up your butt, boy.” With a finger he started to lube up my hole, then worked his finger inside me. He hit my prostate and it felt incredible, making me feel like I was about to cum and piss at the same time, nice!
After a while he paused in his massaging. “Your pussy hole is too tight for my intimidating bit of hardware tonight. We’ll have to save it for another time. Frank use your hands on this boy’s sensitive parts. Tickle him without mercy while I work his pussy hole until he either explodes laughing or gets so fucking horny he doesn’t know which way is up.” Sir grabbed my dick with his free hand and started stroking me off at the same time that he extended his finger deeper into my hole, and pushed it upwards against my prostate.
Frank’s meaty hands proceeded to tickle my feet from toes to mid-section, over and over in little circles. There was no getting away from him. I began to laugh hard as my dick grew harder. The prostate massage was mind-blowing as were Sir’s very soft hands stroking me off. I was squirming in pleasure and screaming with laughter. After a while my voice started to crack. Frank went back and forth, tickling me beneath my knees and on my inner thighs, but always returning to my feet. I was going crazy.
Sir was enjoying himself. “That’s right, boy, scream away. You probably won’t be able to speak tomorrow, no loss.” He dug deep into my hole, paused to put a big gob of lube on his hand and then worked my dickhead. “This is called apple polishing, something you’ll really enjoy after you cum and I continue doing it.”
I lost all sense of time and even forgot where or who I was. I was just a thing of sensations that I wanted to stop and didn’t want to stop at the same time.
Sir retracted his finger and put something in my hole that I had never experienced before. It was like an electric knob. When he started up the charger, the throbbing inside me was incredible and delicious sensations went right through my bowels and lower regions. Meanwhile Frank’s crazy tickling never stopped. He was now lightly teasing my chest and my sides and along my neck too. That drove me totally wild, I was in ecstasy.
“I’ve been neglecting the boy’s cock, Frank. I’d better do something about that.”
Sir left the buzzing, throbbing thing in my ass and put another vibrator in a tight sleeve on my half-hard dick.
“Frank, our guest is getting noisy. Please kiss him hard and swallow any noises he makes for the next five or ten minutes. Don’t remove your mouth until you see or feel him shoot his cum.”
Frank engulfed my mouth, working his lips and pushing his tongue right down my throat. It felt amazing! My dick was at full attention, enjoying the pulsating sensations of the vibrator/sleeve thing. Sir was now pumping away crazily and he also upped the current on the butt device too. I was moaning and screaming, but my sounds were muffled by Franks massive mouth on mine.
“So then, next time you come to Montreal, you tell your new friends what kind of treatment you got from your Sir tonight. And one more thing: once you shoot, and you will, the stroking will not stop!”
Almost immediately I shot my load.
The pumping and vibrating sensations milked out tons of jism on my chest and all over Sir’s hands. He turned off the butt-plug and hastily drew it out of my body. Frank was pulled off me. I gasped for air.
“Frank, here’s some boycum, feed it to him.” And with those words, Frank slurped the cum off Sir’s hands (there was a lot!) and gave it back to me with one deep kiss.
Sir was still stroking me. Now that I had cum my dick was more sensitive than ever and I was also laughing, completely out of control! I wanted him to stop as I squirmed wildly with my legs still tied over my head. I couldn’t get any relief; I was totally out of my mind.
Sir stopped and whipped the vibrator thing off my dick letting it flop against my sticky wet chest. “There, there, boy, I can be a kind master once in a while.”
Things quieted down quite a bit after that. Sir and Frank released me from the ropes and they massaged my wrists and ankles which were pretty red. I noticed neither of them had shot and asked if they were going to add to my mess.
“Never mind, boy, it’s all about you tonight! This is how a true Montrealer who’s into BDSM welcomes new slaveboys like you! Did you enjoy yourself?” He rubbed a towel all over my chest, and particularly on my swollen and shrinking cock. I had enjoyed myself, of course, and told him so, thanking him for all the fantastic hours of pain and pleasure. Sir asked if I felt safe enough to sleep at his place tonight and enjoy breakfast in the morning. How could I refuse?
“Right. Frank, do one last thing before you leave. Put this cock cage on him, would you? I can’t see very well, and don’t want to injure his dick by mistake.” Frank put the chastity cage on me and locked it. Sir told him to take the key with him when he left. “This way even I won’t be able to free you until Frank comes by tomorrow.” My dick, now bound tight, suddenly expanded to the full inner dimensions of the cage and pressed hard against it.
“Now let’s see,” said Sir. “Here’s that leather sleep sack, perfect! Here, boy, hop inside and Frank and I will tuck you into bed. Wait. Do you need to pee? No? Good. Now just slide your arms down those inside sleeves. Good boy.”
The two of them zipped me up and used large belts to tightly encase the entire sleep sack. Only my head was exposed. I was totally immobile. It felt great. Sir added a pillow and asked if I slept on my side. The two of them fussed about until I was sort of in a normal sleeping position.
With that Frank and Sir enjoyed a very long, steamy kissing session in front of my eyes. They licked each other’s beards and grabbed each other’s cocks, and even felt up their chest and tits, all of which made me want more hot sex. “Okay Frank, that will do! Let’s continue in the morning when you come back with the key.” The toys and equipment were quickly put away, and I could hear Frank get his clothes on. He gave me one very long, hard kiss and patted me on the cheeks.
Once Frank left, Sir came back into the room and warmly rubbed my face with his hands and kissed me everywhere on my face. It was good to feel his stubbled beard against my skin. “You made me very happy tonight, boy. Don’t worry about my own cock, you’ll have a chance to enjoy that tomorrow once Frank comes back. And I’m sure a mouth like yours can service your Sir’s cock well, yes? Now I’ll dim the lights. I’ll come check on you every so often through the rest of the night. I might even tease your tits or cock a little more at times.”
That got me curious and excited! I felt very lucky to have met up with this stranger and to enjoy all these erotic pleasures. One last thing I asked him for was his name. “I’ll let that remain a mystery for a while. You can call me Sir and that’s enough for now. Sleep tight, and don’t get hard!” But his words were almost lost on me as I was falling fast asleep and very content indeed.
WOW! What a hot story!
Posted by: Jack | May 01, 2020 at 07:58 PM