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“Honey, can you do me a favor?” Margot asked over the phone. “My parents are going on vacation for a couple of weeks and they want Kieran to come stay with us until they come back. Can you give him a ride so they don’t have to spend money on a plane ticket?”
I suppressed a groan. Kieran was Margot’s little brother. He was a snot-nosed little punk who’d spent his whole life relying on his parents to handle every little thing, so I understood why they couldn’t trust him to be by himself, even if he was eighteen.
I hadn’t seen him since before Margot and I had moved halfway across the country for work (I was back home visiting my own family when Margot called to ask if Kieran could tag along on my drive home). Margot could tell right away that I wasn’t thrilled at the prospect of spending the better part of three days on the road with that whiny little shit.
“Babe,” she said with the voice she always used when she wanted something, “just do me this one favor and I’ll give you an extra special surprise when you get back.” My dick twitched ever so slightly because I knew she was implying something sexual.
Margot and I had been dating since our senior year of high school. We had a very healthy sex life, but there were still certain things she was unwilling to do, despite my best efforts to persuade her otherwise. Her promise of “an extra special surprise” could be one of any number of lewd acts I’d been trying to goad her into performing. If I played my cards right, this could be worth the effort after all.
I agreed to her proposition and swung by her parents’ house the following morning. Her folks greeted me at the door. They had always seen me as some wholesome young man that would make an honest woman of their daughter soon enough, not the sexual deviant that had snuck into their house at 2 in the morning to pop their baby girl’s cherry while they slept. While we chatted, Kieran made his way awkwardly downstairs with a duffel bag full of clothes.
He had hardly changed since the last time I’d seen him. He was still a bit short for his age, with a slender, almost feminine body. His dark hair was almost down to his shoulders now, and his skin was far too pale for this time of year. I wondered if he ever ventured outside his bedroom during the summer months except to eat and use the bathroom. When I was his age, I was already working full-time in the summer and was spending most of me free time dicking down his older sister. Kieran looked like he would instantaneously cream his shorts if a girl so much as glanced in his direction.
“Well, we’d better get going,” I said.
“Don’t give your sister or Jack too much trouble, Kieran,” his father said. The guy just rolled his eyes right at his parents. My old man would’ve knocked my ass out if I’d have given him that kind of attitude, but Kieran’s parents were always soft on him.
“Thanks again, Jack,” Kieran’s mom said. “This trip cost us quite enough to begin with.”
“It’s no problem, Mrs. Viola.” I headed out to my truck, with Kieran dragging his feet behind me. I tossed his bag into the toolbox mounted behind the cab and locked it, and we hit the road. The first several hours passed uneventfully. Kieran didn’t speak to me, I didn’t speak to him, and that’s the way I wanted to keep it.
We stopped for lunch (I paid since he was a free-loading punk barely out of high school), and afterwards I asked him to put gas in the tank while I went to take a piss. I should have known that was a waste of time, since I came back to find him sitting in the passenger seat, whining about how he doesn’t know how to pump gas. As politely as I could muster, I offered to show him how, but he just sneered at me. I could feel my blood boiling, but Margot’s sexy surprise offering kept me from dragging the little bastard out of the truck and beating the shit out of him.
After fueling the truck myself, I got back on the road and didn’t speak to Kieran until we pulled into the motel for the night. I ordered us a pizza that we ate in silence before I turned off the lights and went to sleep.
Several hours later, I got up to take a piss, but Kieran’s bed was empty and there was a light coming from the bathroom door. I waited for him to finish, but after fifteen minutes, he was still in there. I had had enough of this little bastard, so I rolled out of bed to hurry him along. As I neared the bathroom door (which I now noticed was cracked open), I heard Kieran’s voice speaking softly.
“Ooh, Jack,” I heard him moan, causing me to pause. Had he heard me coming? Then he continued, “Don’t fuck my ass! I’ll do anything you say!”
What the fuck! I thought. Slowly, I pushed the door open wider. What I saw was a real sight to behold. Kieran was standing in front of the mirror, his forearm resting on the sink. The only thing he was wearing was a pair of panties that were several sizes too big and bunched up just below his bare ass. He was reaching one arm back and while I watched, he slowly slid a finger into his own asshole.
You’ve osmaniye escort got to be kidding me, I thought, the little bastard is fantasizing about me fucking him in the ass! An idea suddenly popped into my head, and I quickly and quietly rushed back to the nightstand to grab my phone. By the time I got back, he’d started again.
“Oh God, Jack! I’m so glad my sister brought you home! You’re fucking my boi-pussy so good!” I had already started recording and figured that would be good enough.
“Can you repeat that last part?” I said. “I want to shoot it from a better angle.” Kieran spun around and nearly tripped over the panties that had slipped down around his knees. His dick, while fully erect, couldn’t have been more than four or five inches long. He panicked and struggled to pull his panties up while covering himself. That just made it more ridiculous, seeing him cowering in a motel bathroom wearing panties that were far too large for him (and now that I got a good look at them, were far too modest for doing anything erotic).
“J-J-Jack!” he stuttered, practically pissing himself as I continued to keep the camera focused on his face. “What the fuck are you doing in here?” He raised his voice, as if trying to sound authoritative, but it just made him sound shriller and more effeminate.
“I could ask you the same thing!” I said, my booming voice echoing in the tiny bathroom and causing him to cower even more. “Fantasizing about your big sister’s boyfriend and fingering your ass! And whose panties are those, Kieran?” I panned the camera down to get a good shot of the rapidly shrinking bulge beneath pale pink cotton.
“Stop!” Kieran shrieked, grabbing for the phone. I pulled it out of his reach and grasped his skinny wrist with my free hand. With little effort, I dragged him out of the bathroom. Just before I got to his bed, he took a swing at me with his other hand. I’d been expecting that, so I avoided his pitiful attempt at a punch and dragged him even more forcefully to the far side of the room.
I tossed the phone onto the bed nearest me so I could use both hands to drag Kieran forcefully to his feet. The little punk found himself pushed face-first into the corner.
“Place your hands on the wall!” I ordered. He continued to push back against me, so I swung my hand in a low arching sweep and caught him on the right ass cheek with the palm of my hand. I couldn’t hit him as forcefully as I wanted to, but he still squealed loudly and clenched his ass tightly to brace himself against any follow-up spanks.
“I said place your hands on the wall!” I barked directly in his ear. Any defiance he had left melted as he complied. “Now I’m gonna ask you one more time: whose panties are you wearing, Kieran?” He mumbled something incoherently, so I struck him even harder on the ass.
“My mom’s!” he yelled, taking his hands off the wall to clutch his sore backside. I gave him a slap on the other cheek and told him not to take his hands off the wall again. He reluctantly placed his hands on the wall, facing the corner. I took a step back to look him over. He looked even scrawnier without any clothes on. His pale skin was soft and virtually hairless, which only made him look even more feminine from behind.
“You little pervert! Raiding your mom’s underwear drawer! Fingering yourself in the bathroom while fantasizing about your sister’s boyfriend! What do you think they’re going to say when I tell them about this?”
“NOOO!” he yelled, almost turning around before he remembered what would happen if he did. “Please, Jack, don’t tell anyone! I’ll do anything!”
“Yeah, you said the same thing when you were begging me not to butt-fuck you! And don’t act like you didn’t, I recorded you saying it.” Kieran turned to look over his shoulder, a pleading look on his face. He was practically on the verge of tears. If he looked girly before, it was nothing to what he looked like now. I always thought I was straight as an arrow, but now I could feel my own dick starting to stiffen. I tried to push the thought from my head and get back to the task at hand.
“So, you’ll do anything? Ok, we’ll see about that.” I grabbed him by the hair and dragged him whimpering across the room to the bed, where I picked up the phone. “If you want me to delete this video, you’re going to do exactly as I say until we get home. Understand?”
“Yes,” Kieran said, his voice every bit as small and feeble as the rest of him.
“Good. First thing’s first, when I tell you to do something, it’s ‘Yes, sir’. Got it?”
“That’s a good boy. Now get moving!” I dragged him over to the other bed (the one I’d been sleeping on). “Put your hands on your head.” No sooner had he done so when I hooked both thumbs into the waistband of his oversized panties and swept them down past his knees. His cock had shriveled up during his time in the corner next to the air conditioner and was positively tiny. The boy tried to protest, but I effortlessly pulled him down over my osmaniye escort bayan knee, reached back and pulled the panties all the way off, tossing them over to the other bed.
“I know your parents always preferred to coddle you, but I assure you I prefer to use a much firmer hand.” I slapped his bare ass with an open palm, bringing forth a yelp from Kieran. “That one was for stealing from your mom! When you get home, you better put those back and never touch her panty drawer again.”
“Yes, sir!” he whined. I gave him three more slaps, alternating cheeks with each blow. He tried to get away, but I had my left arm wrapped securely around his tiny waist, and all he could do was helplessly squirm on my lap.
“Where do you think you’re going? You’ve had this coming for a long time.” I began spanking him even harder, causing to writhe in pain as best as my firm grip would allow him. Even in the dim light given off by the bathroom light, I could tell that his ass was rapidly turning a bright shade of red. I had him crying in under a minute, and he stopped struggling soon after, all resistance completely beaten out of him.
I probably would have stopped right there if I didn’t suddenly feel something warm and wet on my leg. At first, I thought Kieran had pissed on me, but I quickly realized there wasn’t enough for that to be the case. Furious, I pushed him off me to the floor below. Sure enough, there was a large spot of white, sticky cum on my boxers and thigh.
Kieran was sniffling on the floor, tears streaming down his face and the last few drops of semen still clinging to the tip of his penis. I was so engaged in beating his ass, I hadn’t noticed his dick get hard until after he’d blown his load all over me. It took all the self-control I could not to kick the living shit out of him right there in the motel room. Instead, I dragged him to his feet by his hair and led him back to the corner.
“You like that, you little pansy?” I said, shoving him face-first into the corner. “First you dream about getting fucked in the ass, then you get off on me spanking you?” He said nothing in response, he just hung his head and continued to sniffle. I stripped off my boxers, using them to wipe the cum off my thigh.
“Open your mouth!” He opened his mouth slightly, so I forced it all the way open with one hand and crammed by jizz-soaked drawers inside with the other.
“Don’t you dare take those out or leave that corner until I get back!” I ordered. I turned around and walked to the bathroom to take a quick shower. When I returned, Kieran hadn’t moved an inch. His ass was bright red in contrast to the rest of his pasty skin.
My anger had subsided while I showered, and as I admired my handiwork, I could feel something stirring beneath my towel. Much as I hated to admit it, Kieran wasn’t the only one who’d been aroused by the night’s activities. His ass was as silky smooth and soft to the touch as Margot’s, and while not quite as plump as hers, it still had a girlish feel to it. From behind, he looked more like a young woman than a boy fresh out of high school.
“Get over here and get down on your knees,” I called to Kieran after taking a seat on the bed, my hotel towel still wrapped around my waist and just barely containing my throbbing hard-on. Kieran walked over and knelt in between the two beds, limping slightly from his sore backside, the boxers still wedged firmly in his mouth. He’d stopped crying now, though his eyes were still red.
“I think you can take those out now,” I added, indicating the boxers. After he’d withdrawn them from his mouth, I continued, “So, you’re gay?” I expected him to deny it immediately, but he just sort of shrugged his narrow shoulders without looking at me.
“I like girls,” he mumbled after a minute, “but- I don’t know- sometimes I would catch glimpses of the other guys in the locker room after gym and…” He started to trail off, blushing almost as bright red as his ass was.
“You saw something you liked?” I finished for him. “And why is it me you were imagining bending you over the sink earlier?”
“Back when Margot first brought you home, all I could think about that night was you. And then I heard her telling her friends about blowing you in your car, and how big your dick was.” With that, he quickly glanced at the bulge beneath my towel, the first time he’d looked at me since he left the corner. I pretended that I didn’t notice.
“So that’s what this is about?” I asked. “You got a crush on your big sister’s boyfriend? That’s why you were knuckle-deep in your own boi-pussy.” He cringed when I called it that, blushing harder than ever. His humiliation only made my own lust increase. “You want a dick in your ass, don’t you?”
“No!” he moaned, not entirely convincingly. “I-I just think about it sometimes when I masturbate. That doesn’t make me gay…does it?”
“I don’t know, I’ve never thought about taking it up the ass from another man. But you can’t stop looking at my cock, can escort osmaniye you?” I had just caught him glancing at my growing bulge as I started talking. Caught in the act, Kieran froze like a deer in the headlights. “You want to see it so bad? Here, take a good look!”
On a sudden whim, I stood up, discarding my towel as I did so. My cock sprung to attention less than a foot from Kieran’s face. If he was looking before, he was outright staring in awe at it now. I twisted my hips ever so slightly, making my dick swing back and forth. Kieran never took his eyes off of it. I leaned forward until my dick was inches from his face, laughing as Kieran went cross-eyed trying to keep his eyes on it.
“Yeah, you love dick,” I told him. For the first time since I’d caught him in the bathroom, he turned to look me directly in the face.
“It’s just so…big!” he said. Not to brag, but he was right. My dick was a solid 9 inches long when fully erect and was so thick that Margot couldn’t wrap her fingers all the way around it when she jerked me off. Kieran must have read my mind, because the next thing he said was, “Can I touch it?” I hadn’t expected this, but it didn’t take long for me to come to a decision.
“Admit you love cocks and you can touch it.”
“I love cocks,” Kieran mumbled.
“Like you mean it!” I barked.
“I love cocks!” I nodded my approval and he reached up and gently took my penis in his hand. I sighed. It had been nearly two weeks since I’d had any release and his hand was every bit as soft and delicate as his sister’s. Without having to be told, he began slowly stroking my cock. As he did so, he briefly looked up at me to gauge my reaction.
“Hmm, someone’s eager,” I said. He gave me a nervous smile. “That’s it, nice and slow. Fuck, that feels good!” Kieran was staring lustily at my cock now as he jerked me off. Slowly, he moved his head closer to the tip of my penis, and bent down to kiss the tip. As much as I liked his enthusiasm, I felt the need to keep control of the situation.
“Hold it! I told you that you could touch it, that’s all!” He stopped immediately, scared of whatever retribution might befall him for disobeying me (just like I hoped he would). “Put your hand down and lean forward.” He did so, and I slapped my dick across each cheek. “Never-do-something-without-my-permission!” I ordered, each word punctuated by another slap of my meat across his slutty face. “If you want something, you better beg me for it!”
“Please, sir,” Kieran pleaded. “May I give your cock a kiss? And…” Kieran paused, as if willing himself to say what he really wanted. “May I suck your cock?” I held my cock up to his mouth.
“You want it, slut?” I said, “It’s all yours. But you are going to finish anything you start, understand?”
“Yes, sir.” Kieran bent down and kissed the head of my dick. Then, he stuck out his tongue and slowly licked the tip. Damn, I was so horny that I almost crammed my cock down his open mouth right there, but I restrained myself and let him go at his own pace. For now, anyway. Finally, after a moment’s hesitation, he took the first few inches of my dick into his virgin mouth.
“Fuck yeah,” I moaned as he started sucking, “that’s good.” It was actually kind of a sloppy job, but after two weeks without any release, it felt amazing. It reminded me a lot of the first time Margot had gone down on me, how little I cared about her lack of experience because I was just a horny teenager at the time. Kieran bobbed his head up and down, taking more and more of my cock as he did so, though nowhere near to downing the full nine inches.
“Take it out and lick up and down the shaft,” I ordered, and he did so. “That’s better. Now don’t forget the balls.” He took each of my swollen testicles into his mouth in turn and sucked on them. “That’s a good little slut! You learn quickly, don’t you?” He blushed, whether from embarrassment at being called a slut or pride at being complimented, I neither knew nor cared. I just wanted my shaft back in his mouth.
“Let’s see how much of it you can take,” I said, guiding the head of my dick back to his eager mouth. He downed a little over half of it before he tried to pull out. He was so focused on my cock, he hadn’t noticed that I reached around to grab the back of his head until I pushed his head forward as I thrusted my dick further down his throat. He gagged and I let him come back up for air.
We repeated this process several more times until he finally managed to down the entire length of my shaft, my balls slapping against his chin. Damn, I thought, I wish Margot had been this eager the first time.
I told Kieran to work his tongue around the tip and he did, licking the precum off it like it was an ice cream cone. Then I had him wrap one hand around the base and jerk me off while he sucked on the tip. He was eagerly following my every command, desperate to please me.
“Look up at me while you suck me off, slut,” I ordered. He did so, and his watery brown eyes gazed up at me with a look of pure lust. Kieran looked almost exactly like his sister from that angle, and I could rapidly feel my orgasm approaching. I pulled my cock out of his mouth and started stroking it. “Don’t you dare fucking move!” Kieran just sat there on his knees, staring at my cock like he was looking down the barrel of a loaded gun.
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