That One Night, 24 Hours.
By all accounts, I was your average college student, a young 20 year old Asian guy who probably could stand to put on a few pounds, but never seemed to no matter how much I ate. My body stayed somewhat slim but toned, thanks to some combination of childhood soccer and swimming in high school. I had always thought that I was into guys, and that wasn't cemented until the first time I entered a locker room and my best friend came up to me, his penis swinging between his legs and hugged me for making it onto the swim team with him. Yes, I actually did eventually get to... experience... his penis, but drunken stories are ones that we promised not to share... for his girlfriend's sake.
Anyway, this story's a little different from the other periods of my life, it was the summer break of my 2nd year in college, I had finally gotten settled in my apartment, and despite subscribing to the "personal" boards of my city, I had always taken a dirty pleasure in reading the ads taken where a man looked for a "boy" to have for the night. This time though, a particular ad caught my eye.
"Boy wanted for 24 hour session" it said, the finer details, I don't remember, but the rest of the ad promised a good time for anyone who was willing to commit to a whole day's worth of "play" though I do remember it was quite vague. I messaged the ad's listed email and described myself to the guy, and even just through our emails, I felt as if he were towering over me and already having a grasp on me.
At that time, I had just tinged my hair a slight shade of brown after a failed dying experiment, black hair like mine... does not take well to dying. I had my light brown eyes, a sharp jawline with just a soft rounded chin, and a preference for wearing my glasses, even though I could function perfectly find without them.
He, of course, was less interested in my looks and was a bit more interested in things like: Bdsm? Yes. Chastity? Maybe. Spanking? Yes. Insertion and Stretching?
I paused at this mention, and feared for a moment if this was one of those men who would throw me into a sling and shove a fist in me. My body had taken, very painfully, a large dildo before, but I wasn't sure that I was into it. Yet, before I could answer his response was
"It doesn't matter, you'll do it anyway." And he was right.
The next morning I woke up at 9AM, the previous night's efforts to shave and trim myself looked neat now in the bathroom mirror as I got out of the shower and proceeded to towel myself dry. My abs were still soft and I wondered if they'd ever fully come in, but for now this was enough.
I threw on a pair of basketball shorts and a t-shirt like he had instructed, and began my drive, about 15 minutes away from my campus apartments. The whole ride, I was very aware that the sheer fabric of my shorts rubbed against my dick, going commando was something I hadn't really ever done, underwear just seemed a natural thing to throw on without thought. I felt my heart race as I got closer and closer, and had to steel myself for a moment before I parked in front of what seemed to be a relatively large house.
As he had said, the door had been left unlocked, and I walked in to find a nice foyer with a center table on it. A quickly written note welcomed me, and instructed me to go to the back and "get in".
I didn't quite understand what it meant until I looked into the backyard and noticed a pool and a small heated hot tub that had been started. Its bubbling waters and a small tray of drinks indicated I was probably supposed to get into the tub, but... that pool seemed so cool and refreshing...
"You can swim laps if you'd like." A voice came from behind me and I jumped. "S-Sorry." I said reflexively. "Ah... you're a cute one... " he smiled, an older guy, probably in his early 30s, he had a built body, well rounded but not quite "buff". "I don't have trunks to change into." I said, stupidly. "After what we're going to do... do you think modesty is a thing you need to worry about?" He smirked as he poured some water from a pitcher and drink it down.
I didn't quite understand what he meant until it clicked and my face turned a crimson red, he was right. I took off my shirt now, and looked at the pool before putting my hands around my waist. Slowly, I tugged at my shorts and the moment they slipped past my hips I felt them go, the rest of my body coming into view. I could almost feel his eyes scanning me, and he made no pretenses to hide he was doing so. I hopped into the cool crystal blue waters and for a moment felt in my element as I swam laps back and forth, almost completely forgetting that I was in fact, completely nude.
When I had finished and was resting on the steps, my breath ragged from the exercise, I felt him come up behind me, and put his hands on my shoulders.
"Come." He said, in a quiet, but stern voice.
I must have taken a few moments to register what he wanted me to do, so instead of waiting he put his hands under my arms and practically lifted me up. He moved over to the hot tub and I got into it. The warm waters brought back all the feeling in my tired legs and I sunk until the warmth enveloped my body. He began taking off his clothes, and when he reached his pants, I could see a bulge in his crotch area, one that seemed to pulse slightly, and strain against the fabric of his underwear now. He stripped off his underwear and I stared at the massive monster between his legs, the bulge in his pants did nothing to prepare me for his cock.
"Don't worry, you'll feel it soon enough." He grinned as he got into the water and sat down at one of the chairs along the side wall.
"Come." He gestured next to him, but as I made my way over he grabbed me instead and sat me down in his lap, his arms clutched around me and he kissed the back of my neck as I turned to jelly in his arms.
"You're such a beautiful boy." He said softly, his hands exploring every inch of my body. I moaned as he tweaked a nipple, and cringed a little as his other hand tickled my side on its way down.
"How big is my little boy?" He asked softly as his hand grasped my cock, which I hadn't even noticed had become rock hard.
"F-fi.. Five and a half..." I whispered, and he nodded knowingly. My attention had focused now on the growing sensation behind me. His cock had steadily been getting hard and now sat pressed between my back and his body.
"You're mine to do whatever I want in the next 24 hours..." He whispered, and I nodded. He caressed me for another few moments, as if to size me up, or dare me into chickening out. I felt like such a slut then, sitting there on his lap, naked, as I let his hands explore the smallest crevaces my body had to offer. It was then that he offered me a glass of champagne to toast our fun, and I gratefully drank it, anything to help take some edge off.
I think at this point I had blacked out, something in the drink made me incredibly sleepy and I remember falling back into him, my head resting against his shoulder. But now, I was in his bed, naked, and I could feel the soft sheets beneath me as they glided along my naked body when I moved. Except, I couldn't move very far.. there were cuffs attached to my wrists and ankles now, and he came back into the room now, grinning as I realized my predicament.
"You're going to be mine tonight boy..." He smiled as he leaned in and gave me a kiss.
"Do you know.. that drugs are an amazing thing now...?" He said as he went to the small drawer next to the bed.
When he had turned back around, I got to see that he was holding a pill and before I could ask what it was he popped it into my mouth and held it shut. Instead of choking on it, I quickly swallowed with what little saliva I had.
"Some like those pain meds are meant to make you feel less, but this one... is made to make you feel more..." He grinned as he pulled out another item. A smaller metal device that seemed to have a tube and a ring...
"Tonight, you wont really need this..." He laughed as he got onto the bed between my legs and began to fondle my penis.
In a few deft motions he put the ring on me, and I finally understood what it was. A chastity device. It almost felt too small, he put it on and happily announced it was a perfect fit. Hearing that, sparked my now locked anatomy to rise, and instead of freedom, it was hampered now, hugged tightly by the cage and I whimpered as the coolness of the cage seemed into my pores and I cringed against. The soft bedding now seemed to send tingles up my spine as I moved and I whimpered again. My every nerve seemed to tingle now as the smallest motions seemed to radiate across my body. I felt a soft heat spreading inside me and I couldn't help but pant as I tried to rub every inch of me to get more of that feeling.
"Yes... you'll love it." He chuckled as he pinched my nipple and I cried out.
What followed seemed like endless hours of agony, my sensitive nipples under his careful hand became such a source of pleasure, and I cried and begged for him to play with them, to send that sensation all through me, and yet all the while I was very aware of my cock, rendered useless now, straining in the cage. He left me to my own devices on the bed as he stepped out to "prepare." I felt that warmth spreading through me now, my body thrust upward in the air, trying to lessen the stimulation from the bedsheets, but the air that wafted over my body was worse... so much worse.
I remember feeling as if my entire body were tingling and that feeling got more and more intense the longer I lay there. The sheets rubbed against me and sent vibrations through my body, and my exposed body felt every breeze caress me and the chill made me tremble.
It what was probably about ten minutes, I felt as if I had gone through hours of torture. My captor came back and smiled as he declared that the medicine was now in full effect. He had brought back a small pouch that I didn't quite recognize, and my eyes must have shown my wonder as he assured me we would be playing with it soon enough.
"I just want you to enjoy yourself... as I enjoy you..." He said in a mock-creepy tone before smiling and running a single finger down the center of my chest, tracing my muscles and making me cringe from the sensation.
"P-pplease..." I gasped as he began tracing the small cervices of my abs.
I hadn't even noticed until now that his other hand was slithering down against the cage that I was still straining against. His hand grazed against my balls and I nearly screamed as I felt a faint feeling of wetness... except... I could feel it... come from me...
"Look at you messy little boy... " He smiled as he caressed me again, my body writhed and in doing so sent me into another spiral of sensations.
I had somehow managed to piece together enough of myself to look at my body and I noticed a pool of what looked like cum... dripping out of me. An impressive amount only possible from the week of abstaining from jerking off he had requested I do.
His hand must have grown tired of playing with me and decided to step it up. He pushed down on the cage, and I groaned as the now warm metal forced my failed erection downwards and I felt that straining sensation send me to new heights. A hand slid further down until he pushed open my legs and his finger rested on just the outside of my rosebud. He expertly ran circles, tickling me almost, and I was suddenly very aware as he pushed ever so slightly, and instead of penetrating me, moved his finger in circles, pulling me with him.
"Your dirty little hole is so hungry isn't it?" He asked, as I felt the finger suddenly become wet and slick.
No motions for any lube came from him, and I realized, he was using the cum that had dripped out of me. My cock strained harder if that was even possible against my cage, his free hand ran up my body and stuck itself on my face, a single finger pulling my mouth open as guttural moans escaped me the moment his finger went in.
Very... very... slowly... he pulled it in and out of me. He knew how to take advantage of this... whatever he drugged me with. A single finger did nothing to stretch me or make me feel full... but just the sensation of his finger gliding along my hole made me scream in pleasure.
"Shhhh..." He whispered as he kissed me, and continued exploring with his hand.
Another finger slipped in now and I felt that huge wave that I had been riding for the last eternity suddenly crash as I climaxed again and felt that warm wetness coat my locked cock again.
"Oh... look at that... you've still got so much cum in you" He teased before scooping some of it up and packing it into me, burying it further with every thrust of his fingers.
"I.. I c-cant..." I panted, but he paid me no attention.
Another finger entered me now, he drove them as deep as he could in one go and I cringed as an intense wave of sensations rammed through my body and reverberated in my brain.
"You know, I always think a boy is best when he's being milked, and his hole is full. I love seeing a boy who knows how to wreck his own little boy pussy." He said, giving me a small kiss on the cheek before getting up and leaving the bed. I should have watched him, but my body was so tense from the last few minutes that this small reprieve from any sensations left me exhausted.
He came back a few minutes later and set up a machine at the foot of the bed. Without any warning the cuffs around my legs were undone from the bedposts and redone to stretched straps around the top of the bed, making me lift my legs and exposing my butt. Shivers ran over me as the cool air ran across my now very sensitive hole.
"What... are y-" I stopped as I realized he was mounting a dildo on a pole, it was a decently sized toy, but it wasn't necessarily the size that worried me. From what I could see, it was a long, roughly seven inch dildo, with a decent diameter and a nice thick head... but was fitted with alternating regions of studs and ribs all along its shaft.
"N-No, please.. that'll rip me up..." I started to plead. "Oh no boy... you'll love it..." He smiled as he pushed the lubed head up against me. I whimpered to myself and shut my eyes, but nothing ever came. He instead positioned himself beside me and smiled gently as he kissed me again and put something in my hand. "I know that you really want this to destroy you don't you boy? You love the feeling of being fucked until you cum don't you?" He smiled and nodded as I realized he had handed me the remote to the machine, he wanted me to start it on myself...
My caged dick strained as I knew he would wait until I had worked up the nerve to push the button and my mind raced before I tensed up and I pushed the button in my hand and I felt the head slowly edge its way into me, opening me up. The large head dropped off finally as I felt the first section of ribs and then studs, he had set the speed to be slow... so painfully slow, but the dildo glided casually in and out of me.
My body twisted in pleasure as every rib brushed and pushed that one special button inside me, and I felt more cum leak out of me.
"You're such a good boy... you know what you need.." He smiled as he positioned himself near my head and nudged the head of his rock hard erection against my lips. At this point, those carnal desires had long overrode any senses I had and my mouth automatically opened and took him in. I had a hunger for his cock, the thing that would soon invade me and the one way I could so please the man who was going to utterly destroy me. His shaft was thick and I could feel the pulsing within his length as he got excited. I worked as hard as I could on his cock, hoping that maybe he'd speed up the dildo inside me, but he looked unconcerned, gently caressing my cheek. After a few minutes I felt his dick swell inside my mouth as I was fed my first load of the night.
"Good boy, didn't waste a single drop." He grinned and got up off the bed. "P-Please... faster..." I breathlessly moaned and he smiled as he took the remote that I had dropped and turned up the dial until the dildo thrust in and out of me at a brisk pace. I cried and screamed as all the ridges forced my hole open and the studs massaged my insides.
"I think Ill go take a quick break... but we'll just leave you like this for a bit... should be fun..." he grinned as he got up and left, leaving the door open so that he could hear me cry.
When I was alone in the room, I was suddenly so aware of the dildo running in and out of me. My body involuntarily twitched and twisted as my overly sensitive hole started to protest all the stimulation. My eyes squeezed tight as I felt the building of another climax deep inside me. I could feel it building and ebbing, and building and ebbing... slowly and then I realized, I had become a bit desensitized to the size of it... that feeling of fullness wasn't there anymore and I knew that I wouldn't be able to cum without it, he had loosened me up with this monster of a dildo...
As if on cue, after this realization my tormentor returned and smiled as he stopped the machine and made motions to remove the monstrous cock that was on it. Again, without much ceremony he pulled a second, larger dildo out of what I guessed was a bag at the foot of the bed and fastened it onto the pole. My new toy was even larger, a thick bulbous nine inch again with a thick head but this time with a shaft that looked like greatly exaggerated anal beads.
"N-No!" I thrashed slightly as I felt the much bigger head against me. His firm hand pushed down on my caged dick and held me in place as I yelped from feeling the sudden pressure on my balls. I felt the first nub enter me and my hole collapsing around the first skinny section before opening again for the next bulb.
I mewled in pain and pleasure as the teasing wave inside me began to build again and build.... Very deliberately he slowly inched up the dial on the machine, and the bulbs went to work destroying what control over my hole I had left. In short order I screamed as the sensations all came crashing down on me and I felt yet another load be pushed out of me. The volume looked smaller now, but the sensations were so intense I felt myself get light headed.
"Such a good boy" He grinned as he pushed a button on the machine and I felt it push all the way inside me, impaling me on the dildo. He left it there for a bit as he started licking and lapping up all the cum on my stomach. His warm mouth against my cool skin make me tremble, and those small motions rubbed the toy inside me, a combination that made me delirious. He appeared in front of me now and kissed me deeply, I felt him motion beside me and before I could look to see what it was, I heard the machine react and pull the whole length of my invader out of me in one motion. The sudden motion coupled with my already on edge body make me shoot again, and before I had time to process things, a warmth surrounded my caged cock and I felt his mouth suck what little cum had come out of me. Now, he pressed his mouth against mine, I couldn't make a sound but I was aware that as he kissed me, he deposited all of my cum back into my mouth and I swallowed it all.
"It's so much sweeter when he comes from the source." He grinned as he undid the restraints, honestly he didn't need them, my entire body was too racked with exhaustion to put up much of any fight. Now I felt him sit me up, and he grinned as he pulled out a pair of small claps connected by a single thin chain. In the center of the chain sat a single small bell and I whimpered as he kissed my neck and teasingly ran the cool teeth against my nipples.
"N-No!" I yelped as the first and the second clap bit into my sensitive skin and he toyed with them.
"I love to hear my boys when I wreck them..." He whispered and pulled me back, his muscles made easy work of lifting my tired body and I felt myself sink onto the pole beneath me that was his cock. It slid in perfectly after his punishments and I moaned as my stretched out hole still managed a weak grip on him.
"You're so loose now boy... I must have done something right..." He grinned as he forced me up and down on him, making the bell between my nipples jingle as it flung in the air and hit my chest. I could feel my caged cock strain again as he knelt behind me, pulling me back and resting my head against his shoulder. In front of me sat a mirror that he had probably set up for this exact purpose. I could see myself, completely naked, covered in remnants of my own cum and a small caged cock that seemed to bounce in time with the bell on my chest. I felt so... ashamed and yet so turned on as the man behind me was thrusting away into my utterly destroyed hole.
I was delirious by the time he came, and I didn't even remember much of it, other than the feeling of being so full. He fucked me over and over again, putting load after load deep inside me. I cried as the clamps were pulled off me during the 6th and final time for the night. His body lifted me up now, and held me up as he pistoned himself in and out of my very sore "boy pussy" as he called it. I was completely at his mercy as he lifted me up and down to make the motions faster, I could feel his muscles tighten against me as he slammed me down onto his hips and his cock buried another load inside me. For a moment he held me tightly as my grip around his shoulders weakened and when I let go he let me fall back onto the bed spent and his cock ripped from my now slightly gaping hole.
"You're one of the most beautiful boys I've ever seen..." He smiled as I barely protested the introduction of a thick plug he put in to keep me open and of course keep his loads inside me for the night.
I fell asleep quickly and I briefly remember waking up in the middle of the night as when he played with my balls and brushed my cage slightly with his hands.
The next morning I whined loudly as my morning erection pushed against the cage so strongly I felt as if my balls were going to burst. He was there immediately, grinning as he shushed me and assured me that it would go away soon, but the cage wasn't coming off yet.
He carried me to the bathroom and let me do my business before laying me into a bathtub, he seemed to know exactly how I was feeling, and I was grateful he carried me everywhere because my legs didn't seem to want to support me anymore.
Out came the plug and I grimaced as he got into the tub and without much ceremony sunk me onto his pole again. I watched as he adjusted the knobs and soon filled the tub with warm water. He went on to clean me off, and scrub me down all while he was buried deep inside me. It was such a bizarre feeling knowing he was invading me, and that I could feel the small flares of tension in his dick whenever he was particularly aroused like when I moaned as he flicked my nipples. When we finished he drained the water and slowly pushed me off of him, a part of me wanted to protest now, the minute I felt him leaving me I felt empty... and perhaps that was his plan all along...
After my bath I felt a lot better and smiled as he offered to towel me off, I could stand now and I felt him search every crevice of my body with that towel. He kissed me again and gave me back my clothes. In all this time, I hadn't been paying attention to the clock. I had woken up so late from my exhaustion that we were about 10 minutes away from the full 24 hours.
"Did you have fun boy?" He asked as he stood behind me now, his erection pushing against my butt, daring me to say no.
I could only nod as he wrapped his arms around me now, and I felt the cage around my cock finally unlock and work its way off. My erection sprang to life again, finally free from its small prison and I moaned as he gave it a few quick jerks.
Very slowly he knelt down and wrapped his mouth around my length and I felt weak at the knees as my long ignored dick embraced every inch of his mouth he gave. I felt him flick the underside of my cock and my legs buckled but he pushed me up against the wall in time to save myself. I felt that all too familiar surge inside me again as wave after wave built and finally....
He stopped.
"I hope you had a fun time... " He grinned as the clock signaled the end of our time
"Please..." I begged
"I never said I'd let you cum... you can do that yourself..." He smirked as he gave my cock head a kiss and left the room.
Suffice it to say, the minute I made it home I took matters into my own hands... I teased myself over and edged myself over and over again replaying the night and the feelings I had experienced. That afternoon I blew the biggest load of my life and I fell asleep with it covering me.
Since then I've always been on the lookout for ads from him marked "24 hours" but they never appeared.
Until one day on the month of my graduation it was there again, from his same username "Boy wanted for 24 hour session"
Click.
Author: Thanks for reading my story! I love hearing from you all and if you have any suggestions or comments, please feel free to let me know at Keito.Nakagawa@gmail.com.
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