Road Trip with a Sissy: Day One

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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 Kieron 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 two 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 my 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 Büyükçekmece escort 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 afterward, 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 got to be kidding me, I Çatalca escort bayan 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 Escort Esenler 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? Okay, 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?”“Yes, sir!”“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 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.”

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