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Road Trip with a Sissy: Day Three

"On the final day of their trip, Jack continues to push Kieran's sexual boundaries."

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I woke up Kieran early the following morning. He wanted to fool around, but as much as I would have wanted to, I still had to keep him in his place.

“Get dressed,” I ordered. He pouted, but did not dare disobey me. He donned the black panties, blue denim cutoff shorts and white crop top I’d bought for him yesterday. And with that, Kieran disappeared from my mind, replaced by Priscilla.

“Does my sissy want to cum?” I asked.

“Yes, sir!” Priscilla said, immediately perking right up.

“Slide those shorts and panties back down to your knees and lie on your back,” I ordered. Priscilla dropped her bottoms in half-a-heartbeat and fell back on the bed. She was already hard, but I paid that no mind. “Start rubbing your clitty.” Priscilla began stroking herself, moaning as she did so.

“Please, sir,” she begged, “fuck me like last night.”

“Aww, is my little sissy thinking about getting a good ass fucking as she plays with herself?”

“Yes, sir,” Prissy answered, “I loved it when you fucked my ass.”

“And did you love it when you sucked my dick?”

“Oh, yes! I love sucking your fat, juicy cock!” She was stroking even faster than before as she got more excited.

“And do you remember the first night when I came all over that slutty little face of yours?”

“Yes, sir! You can cum on my slutty little face anytime you want!”

“Good, but right now, you’re going to cum on your own face.” And with that, I grabbed her ankles and lifted her legs and hips up so that her tiny little dick was pointing at her face. “Keep stroking your clitty, Prissy. I want to see you cum all over your face.”

Priscilla kept stroking furiously in spite of the uncomfortable position I’d just forced her into without warning. In a matter of minutes, she worked herself to the point of orgasm. Her hips bucked as she came, the first shot almost hitting her directly in the eye. I held her tight until she stopped, several decent-sized globs of semen all over her face.

“Good girl,” I said, letting her legs down. “Now pull your pants back up and walk to the truck with cum all over your face.”

“But, sir,” she pleaded, “what if someone sees me like this?”

“Well, they’ll know you had a good time. You’re going to stay like that until I check us out of the motel.” It was still early, so the parking lot was deserted. It was a shame, really. I would have loved to watch Priscilla try to avoid being noticed by curious bystanders.

I unlocked the door to let Priscilla into the truck while I went to the front desk and turned in the room key. When I got back, she was sitting there, cum dripping down her face and getting dangerously close to falling onto her clothes.

“Good job, sissy,” I said. “Did anyone see you?”

“No, sir.”

“Oh, well. You might want to enjoy your treat before you end up wearing it.” Priscilla got the hint and scooped the cum into her mouth. She did miss a few spots, but I wasn’t about to tell her that.

“What about you, sir?” Priscilla asked, giving me her best attempt at a flirtatious look. “Don’t you want to cum, too?”

“Hmm, yes,” I said, “and does my sissy want to make me cum?”

“Oh yes, sir!” Priscilla said, sliding across the front seat. “Can I pull your cock out, sir?”

“Not just yet. Let’s find somewhere a little more appropriate.” I pulled the truck out of the parking lot and sped down the road until I found the perfect spot: a dingy alleyway between two stores on the main road of the town. “Let’s go, sissy.” I saw how nervous Priscilla was, but she followed me out of the truck just the same.

I led her into the alleyway until we were far enough from the street that we wouldn’t immediately attract any attention of someone passing by, but not so far that we were completely out of sight. Once I was satisfied, I ordered Priscilla to get down on her knees and pull my throbbing cock from my jeans. She obliged and in seconds, I felt the familiar sensation of her wet mouth wrapped around the head of my cock.

“Good girl,” I encouraged her. I have to admit, I was more than a little nervous myself. This was the first time I’d ever gotten a blowjob out in open, and the thrill was intoxicating. Priscilla was bobbing her head back and forward like the obedient, little slut I’d turned her into, taking almost the entire length in with every stroke. But she soon started slowing down until she eventually took my cock out of her mouth altogether.

“Sir, my knees hurt,” she whined. Granted, the brick alley was definitely less comfortable than the motel carpet or the front seat of my truck, but I hardly cared.

“Did I tell you to stop?” I demanded, slapping my cock across the side of her face. Then I gave it to her across the other cheek. “Did I?”

“But it hurts, sir!” I knew she wouldn’t stop whining until I let her get into a more comfortable position, but she still needed to be reminded that I was in charge. So I grabbed a handful of hair and dragged her to her feet.

“Sit,” I commanded, pushing her back to the nearest wall. She sat with her back to the cold bricks and I shoved my cock back into her eager mouth. This time, instead of her doing all the work, I thrust my cock in and out of her mouth as she sat there with her back flat against the wall, helplessly taking the face-fucking.

“Is that better?” I asked. She didn’t answer, since she was too busy gagging on my cock. “Good.” I kept drilling her tonsils right there in the alley until I dumped a huge load down her throat. Apparently, she hadn’t been expecting it, because she nearly choked on it before she was able to swallow it all down.

“Thanks, Priscilla,” I said, zipping my jeans up. “I needed that. Now let’s get going before someone sees you. A sissy cocksucker like you would have men lined up around the corner to get a back-alley BJ.” I led her back to the truck and we began our journey for the day.

I phoned Margot to let her know that we might be a little late getting home that night. “Traffic jams on the highway,” I said. In truth, we were hauling ass all morning, but I was having too much fun with Priscilla. It didn’t take long for her to get all hot and bothered again, and soon she was begging me for more.

I pulled into a gas station and sent Priscilla into the store to get drinks while I fueled up the truck. As I waited, I scrolled through my phone and found the video of Kieran in the bathroom from the night before last. Honestly, I’d almost forgotten about it, even though it was the reason this whole thing got started.

The store had large windows in front, allowing me to quickly spot Priscilla near the refrigerators. I texted the video to her phone and waited to see her reaction. I guess she had the volume turned up high because she nearly dropped the phone in shock and began looking around wildly to see if anyone else heard it. In fact, I saw at least one other person turn their head in her direction.

Go to the bathroom,” I texted, “and text ‘Ready’ for further instructions.” She glanced in my direction nervously after reading the message, but quickly headed towards the back of the store without further protest.

Ready, sir,” came the reply a few minutes later. At least she remembered her manners, I thought.

Your ass looks good in those shorts,” I texted. “Why don’t you send me a picture of it?” A few moments later, Priscilla sent me a photo showing the now-familiar curves of her backside just barely hidden beneath tight denim.

That looks good. But I just realized I haven’t gotten a good look at you in your panties. Mind helping me out?” I pulled the truck away from the pump and parked in front of the store in time for a response. I was not disappointed. The low-cut briefs were stretched tight across her cheeks, the bottom of which was sticking out from the leg holes.

Not bad, but I think a thong would’ve suited you better. I know! Give yourself a wedgie and show me those cheeks!” She responded in less than a minute. I admired the smooth, plump mounds of flesh, her pale skin contrasted by the black panties wedged deep in her crack. Now it was time to take things to the next level.

Strip down naked. Using the mirror, give me 3 nudes. All different angles and poses. Make it hot!” As I sent the text, I walked into the store and stood outside the bathroom. The store was nearly empty now.

The pictures came one after the other. The first was as basic as it gets: just Priscilla standing with her back to the mirror, turning her upper body enough to snap the pic over her shoulder. Every 20-something wannabe model on Instagram has one of those. Photo #2 was more promising: the famed “one-finger challenge” where a girl faces the mirror and extends one hand so that her index finger covers the reflection of her crotch and the reflection of the finger covers the nipples. I’m genuinely impressed that she managed to pull it off. But the third picture was the real winner: Priscilla had stood with her back to the mirror and fully extended her arms so that she had taken a full-frontal shot with her ass reflected in the mirror behind her.

Good girl! You look stunning. Why don’t you send me a video of you playing with your clitty?” I checked to see that the coast was still clear. Just the cashier and a couple of people in line waiting to check out. I knocked firmly on the bathroom door. Inside, I could hear Priscilla fumbling around and pictured her trying to quickly get dressed.

“Someone’s in here,” came her panicked voice through the door.

Still waiting for the show to start, Priscilla,” I texted. “Everything ok in there?” I knocked even more firmly this time.

“I’ll be out in a little bit,” she called out, followed by a text to my phone: “Someone’s at the door!”

I know, I saw him follow you to the bathroom. I think he might suspect something’s up.” I waited for her to get the text before knocking louder still, double-checking that no one else in the store was coming to investigate.

OMG, what do I do? He won’t leave!

Let him in.

What?!

He knows you’re in there doing something naughty. Show him the goods, he looks like he might be your type.” I pounded on the door now. “Hurry before he gets the cashier to unlock the door. He’ll definitely call the cops.”

“One minute, please,” Priscilla said and I heard her footsteps across the floor. The door unlocked and swung open. Priscilla stood there in just her flip-flops and panties, a look of fear quickly replaced by relief when she saw that it was just me.

“You naughty girl,” I said, “I didn’t tell you to get dressed. I ought to make you walk out of here like that.”

“But, sir,” she started to complain, but I cut her off.

“But nothing, sissy. Now get dressed and get your ass into the truck if you don’t want it spanked right here in the store.” Priscilla didn’t need to be told twice. I bought the drinks while she had her walk of shame out of the convenience store.

“I’m not going to lie,” I told Priscilla as we drove off, “your photos were much better than I was expecting.”

“Thank you, sir,” she said, blushing.

“But you’ve still got a spanking coming, though. The only question is when and where. Wait, I know just the spot!” Of course, that spot was still a few hours away, but I didn’t tell Priscilla that. It was better to keep her guessing, increasing the suspension as she awaited a punishment that could happen at any minute.

Finally, we arrived at my chosen destination: a state park that Margot and I had gone camping at the previous summer. Given it was a weekday, I doubted many people would be around, but the thrill of doing lewd things out in the open was still too good to pass up.

Margot had texted me while I was driving to see how far away we were. I gave her the name of a town we’d passed over an hour ago and mentioned that there was still a lot of traffic ahead of us. Fortunately, she didn’t ask any more questions. I led Priscilla down the trail for nearly a mile until we came to the same clearing Margot and I had camped at.

“All right, Prissy,” I said, taking a seat on a fallen tree, “drop them.” Priscilla looked around nervously as she unbuttoned her shorts and slid them down to her ankles with her panties. I barely noticed the erection when it sprung free from her panties. She stepped out of her bottoms and folded them neatly, placing them on the log next to me.

“Put your hands on top of your head and turn all the way around slowly,” I ordered. Priscilla complied, giving me an unobstructed view of everything. Satisfied, I beckoned her over and swept her over my knee in one swift motion.

“Well, here we are again, you naughty girl,” I said. “I keep spanking you, but you keep misbehaving. What do you have to say for yourself?”

“I’m sorry that I disobeyed you, sir,” Priscilla said. “Please punish me, I’ve been a very naughty girl.” SMACK! My large hand fell across her far cheek almost exactly as she finished speaking, causing her to audibly gasp in surprise. SMACK! I spanked the other cheek.

“Yes, you have, Priscilla,” I scolded. “Sucking dick in a back alley. Watching lewd videos in the store. Taking nude photos and playing with yourself in a public restroom. And that’s just this morning.”

Priscilla turned her head as if to protest, but I preemptively silenced her with a particularly hard spank. SMACK!

“Oh, I know that I told you to do all that,” I said. SMACK! “But you didn’t protest then, so why should you be allowed to now? I led you into that alley, but you willingly got on your knees and sucked my dick.” SMACK! “I sent you that video, but you opened it in the convenience store.” SMACK! “I asked you for nudes, but you stripped naked in a public restroom without a second thought.” SMACK! “Yes, Priscilla, you were very naughty before you chose to disobey me.” SMACK!

“Yes, sir,” Priscilla moaned. SMACK! “I deserved to be punished hard.” SMACK! “Thank you for disciplining me.” I gave her another dozen swats before ordering her back onto her feet. I could tell her ass was still tender from the belting I’d given her last night. There were tears in her eyes, but she wasn’t sobbing yet. I gave her a pocket knife and carefully supervised her in cutting a switch. I took a couple practice swings and, satisfied, ordered Priscilla into position.

“Spread your feet shoulder-width apart. Bend over and grab your ankles. Now, you don’t have to count these out loud or thank me for each stroke, you just have to stay in position and take them like a good girl. Remember, this is a punishment. You can cry, scream, piss yourself, it doesn’t matter. I’m not going to stop until I’m satisfied that you’ve learned your lesson.”

I took my position on Priscilla’s left side. I gave her bottom a few quick taps to let her know I was ready to start before raising my hand to shoulder height and bringing it back down in one swift motion. Compared to my hand and belt, the switch made almost no noise on impact, but I knew from personal experience that it more than made up for that in pain.

Priscilla yelped in shock as the switch left a bright pink stripe across her ass cheek. Her whole body shuddered as though she had instinctively tried to move out of the line of fire while simultaneously forcing herself to stay in position. I waited a few seconds before delivering the next stroke. My parents had always given the switch and belt in this way: a slow, deliberate pace that forced you to feel every blow. When they used their hands or my mother’s hairbrush, they delivered them at such a fast pace that all the blows seemed to blur together.

After the fifth or sixth stroke, Priscilla was sobbing openly, crying out with each subsequent strike across her backside. I gave her about twenty before switching over to the other side to ensure an even punishment. By the time I finished, her ass was covered with bright red striping and I’d drawn blood in a few spots. Priscilla’s legs were shaking as she wept.

“Put your feet together,” I ordered. After she obeyed, I continued, “I’m going to give you six strokes across the back of each thigh. After that, we’re done.” Beginning again on her left side, I began whipping her thigh and sit spots with sharp, deliberate strikes. She howled in pain with each blow, her voice echoing in the silent forest. Even I paused to make sure she wasn’t attracting any unwanted attention.

After six agonizing strikes had been dealt to the back of Priscilla’s left thigh, I moved around to give the right leg the same. Priscilla took the rest of her punishment as best as she could. When I finished, I told her to stay in that position while I admired my handiwork. Her backside was a mess, and I knew she’d have the marks for days. I pulled out my phone and started recording.

“Ok, Priscilla,” I narrated as the camera lingered on her punished ass, “Stand up straight with your hands on top of your head, and spread your feet shoulder-width apart.” She complied and I walked around her, keeping the camera trained low. Her erection had shriveled up to something resembling a dried-out cocktail weinie.

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“Aww, look at your little clitty,” I teased. “It’s so cute!” Really, it was anything but that. Priscilla was still sniffling, tears streaming down her face as I panned up to get a good look at her. She stared directly at it, giving me the most pitiful face imaginable. I reassured her that no one would see this video but me, and let finally let her move around.

I checked the time. Nearly noon. Margot was expecting us back until after dark, much longer than it would take to actually get there. The blowjob seemed so long ago, and Priscilla had already proven herself an eager, little slut. Besides, I’d always wanted to have sex in the great outdoors.

“Priscilla, come over here,” I called. She hobbled over as fast as her sore bottom would allow. Clearly, she had some idea of what I wanted, so I pushed her down to her knees and pulled my cock out without another word. Priscilla opened her mouth and I stuck it in. She started sucking my dick like she wanted to taste my cum more than anything else in the world. I started recording again, ordering Prissy to look up at the camera as she blew me.

“Well, here we are again, Prissy,” I said. “What is this, the fifth or sixth time you’ve blown me in the past two days. You must really love sucking dick, huh? Let me hear you say it out loud.”

Priscilla took my cock out of her mouth and proudly declared, “I love to suck dicks!” without breaking eye contact with the camera.

“I don’t believe you. If you really love sucking dick, let me hear you say it with the dick still in your mouth.”

“I uhv oo suh diss,” she managed to mumble through a mouthful of man-meat.

“Louder!”

“I UFF OO SUGH DIGGS!” I pulled my cock out and stepped back. Priscilla nearly fell over trying to reach for it with her mouth.

“Yes, you do,” I chuckled. “And what about anal? Did you love it while I drilled your boi-pussy last night?” Her eyes lit up like a Christmas tree.

“Yes, sir,” Priscilla said, speaking fast as though I might change my mind any second. “I loved it when you fucked my boi-pussy! I came so hard! Please fuck me again, sir! I want to feel you cum deep inside me!” God, what I wouldn’t give for Margot to be half the slut I’d turned her brother into. Priscilla was grinning ear to ear when I pulled out the bottle of anal lube from my pocket.

“Turn around, Prissy,” I said, “then bend over and show me that boi-pussy.” She wasted no time getting into the desired position, and I squeezed a healthy amount of lube on her exposed asshole. She moaned as I used two fingers to push the lube deep inside of her. Then, I rubbed some on my raging hard-on before I stuck the head in Priscilla’s ass.

She wasn’t nearly as tight as last night, but it still took quite a bit of effort to stick it all the way in. I gave Priscilla a few moments to become accustomed to my girth before I pulled it out to the head and slammed it back in all the way to the base. Priscilla gasped as my hips crashed into her striped ass. I could feel the warmth radiating off each cheek from her recent spanking. As I thrust in and out of her, I gave Prissy the occasional slap on the ass to remind her of what a naughty slut she was.

“Whose ass is this?” I demanded with a sharp smack.

“It’s your ass, sir,” Priscilla answered breathlessly. For someone who could barely take a single finger up their ass a few nights ago, she’d quickly gotten used to the real thing. She moaned and gasped like a pornstar as I drilled her from behind. Now it was time to see how eager she really was.

“Bitch, I’m tired of doing all the work,” I said, as I stopped thrusting. “If you really want it, back that ass up on it and fuck yourself.” Priscilla did as she was told without hesitation, rocking her hips back and forth to take my dick. But she was no power bottom. She wasn’t taking it as fast or as deep as when I was thrusting, and she slowed to a near stop in a few minutes, too tired to do anything.

“That-“ SMACK! “-was-“ SMACK! “-pathetic!” SMACK! Priscilla squealed from the fresh spanks across her raw backside. I pulled out and ordered Priscilla to her feet. I leaned against the fallen log, midway between sitting and standing. My dick pointed upwards like a rocket about to take off, and Priscilla couldn’t help but stare at it longingly, wishing it were back inside her.

“Priscilla, don’t just stare at it! Sit on it!” Prissy had to stand on her tip-toes just to get her ass high enough. I helped by lining up my dick with her asshole until she managed to impale herself on my shaft. Once she managed to lower herself all the way on it, I grabbed her just behind the knees and lifted her feet off the ground. She cried out in shock as my cock was driven even deeper into her by her own bodyweight.

“Oh, fuck!” she moaned. I lifted her up and started thrusting upwards into her ass. I could feel and hear my fat, meaty balls slapping against her smaller ones.

“Yes!” I hissed in Priscilla’s ear. “That’s the fucking spot! Bounce on that Alpha Male cock you little fuck toy!”

“Oh my god,” Priscilla purred. “Oh, fuck yes! Fuck me like the little bitch I am. Oh gawd, it’s soooo deep!” All modesty had been fucked out of her. The shy virgin that had muffled her moans in the motel mattress as I deflowered her last night had been replaced by a cock-crazed slut whose screaming echoed in the silent forest.

“Careful, sissy,” I said, “people might hear you and come to watch.”

“I don’t care!” Priscilla screamed. “I don’t care who hears me! I don’t care who sees me! I just want to ride your cock until I cum!” She soon got her wish, shooting her load in high-arching spurts. I finished a few seconds later, filling her with hot, sticky cum. Once I was done, I lifted Priscilla off my dick and set her back down on her feet. She staggered across the clearing like a newborn pony, either from the spanking or the fucking (if not both).

I used a large wad of camping toilet paper from my pocket to clean off my dick before pulling my boxers and jeans all the way up. Priscilla reached for her panties and shorts, but I stopped her.

“Oh, I’ll carry those for you,” I told her. “You can walk back like that. After all, you said you didn’t care if anyone saw you.” Now that she’d cum, her opinion on the matter had definitely changed, though she knew better than to protest now.

The walk back was miserable for Priscilla. She wasn’t used to walking that far to begin with, and the switching made it all worse, every step aggravating the welts across her ass and thighs. Cum seeped out of her ass and ran down her legs as she walked. Twice, she had to duck off the trail to avoid a hiker walking the opposite way down the trail.

Finally, we made it back to the truck. I gave her toilet paper to clean herself up with, and laid down a towel for her to sit in, in case she had any more cum inside her. Her panties and shorts were set on the floor by her feet. Priscilla didn’t question or protest this. She had just resigned herself to anything I had planned for her.

I stopped at a drive-thru for lunch. The truck was just high enough (and the cashier short enough) for Priscilla to avoid flashing her. I spent most of the afternoon amusing myself by pulling alongside 18-wheelers so the truckers had an unobstructed view of Priscilla’s privates. She later told me that at least one of them had caught a glimpse of her.

Late in the afternoon, I started asking Priscilla what kind of fantasies she had. After all, this whole thing started when I caught her indulging in one fantasy in the motel bathroom and I was curious to see what other dirty thoughts were floating around her head.

“I don’t know,” she said, shrugging her shoulders awkwardly. “I just see things in videos and think, 'I want to try that.'”

“Like what?”

“Like, I saw this one video where a girl humped a pillow until she came, so I started humping my pillow when I masturbate. Or I read this story about a girl who’s a nudist, so I like stripping down naked when I’m in my room. Sometimes, when I’m home alone or at night when my parents are sleeping, I walk around the house naked. I think the risk of getting caught makes it that much hotter.”

“What about sex?” I asked. Priscilla shrugged again.

“Normal sex videos always made me feel weird because I was a virgin. I started off mostly watching lesbian porn. Then, I started watching MILF porn because my friend Jake has a really hot mom. Then one day, I stumbled on this video where this really hot girl started fucking a guy with a strap-on.”

“You mean pegging?”

“Yeah,” she answered, “I’d never heard of it before. I’d seen girls fuck other girls with strap-ons, but I never thought a girl could fuck a guy with one. The first video made me cum in less than a minute. For the next week, that’s all I would watch. Then one night-” she stopped and looked away guiltily.

“What?”

“I was walking naked through the house one night when I passed Margot’s room and heard you and her having sex.”

“You were eavesdropping on us?” I demanded to know. I was pissed for the first time since Kieran had cum on my leg. Priscilla could sense danger and began talking fast.

“No, I would never…Margot’s my sister! I don’t want to know what she does. When I realized what was happening, I hurried back to my room and tried to forget the whole thing. But I couldn’t!”

“Why not?”

“All of my fantasies are about being dominated. And you just always seemed like the most dominant person in the room. That’s why I couldn’t stop thinking about it. It wasn’t Margot that I pictured getting fucked. It was me.”

Suddenly, everything made sense. That was why Kieran had moaned my name as he fingered his own asshole. That was why he came as I spanked him. Why he sucked my cock with no objection. Why he eagerly spread his ass cheeks as soon as I ordered him to bend over. This whole time, I thought I’d been indulging my own fantasies, never expecting that I’d been fulfilling his.

I looked over at Priscilla, but she wasn’t there. Instead, Kieran sat beside me, a tight crop top hugging his slender frame, his undersized cock fully erect beneath the seat belt. I ordered him to put his panties and shorts back on so I didn’t have to look at it.

Neither of us spoke until after sunset. A few miles from home, I pulled into a small parking lot and walked across the street to a nearby public park. It was closed after dark, but I knew that the cops rarely checked for loiterers, especially on a weeknight. As long as we didn’t draw any attention to ourselves, nobody would bother us. I brought Kieran’s normal clothes since he needed to change before we got home. I texted Margot and told her that we would be there in about an hour.

“Ok, Prissy,” I said, reverting to Kieran’s sissy name as I led him into one of the dugouts at the baseball field. “You and I need to straighten out some things before we get home. But first, hand me your home.” I took it and erased every shred of evidence of the last two days; all of the pictures from this morning, the text messages we’d sent, the video from the first night. Then I did the same thing with my own phone.

“Ok, now that that’s taken care of, here’s how the rest of this trip will go. After we leave here, you will not call me ‘sir’, you will not mention the name ‘Priscilla’, and you won’t make any mention about anything we did the past few days. If Margot or your parents ask about the trip, just tell them how long and boring it was.”

“Yes sir,” Priscilla said.

“Good. The clothes are yours. Do what you want with them. Throw them out or keep them, I don’t care, but you will not wear them at our house. And I don’t want you walking around naked in the middle of the night either. You’re staying in the guest bedroom, and I expect you to handle your business in there.”

“Should I change now?” she asked.

“One second,” I said, pulling out my phone. “You’re going to give me a little show first.” I started playing music, one of those raunchy hip-hop songs you’d hear at any strip club. “Come on Prissy, show me your best striptease.”

It was trash, I won’t even try to defend it. She had no sense of rhythm, gyrating in a way she must have thought was provocative. I had to slow her down so she didn’t strip off all her clothes in the first minute of the song. Any idea of a lap dance went out the window for fear that she’d just sit directly on my balls without a second thought. Finally, it was over.

“How was that?” she asked, fully nude outdoors for the first time in her life.

“Well, I don’t think anyone would have made it rain for that show. Come on and get dressed, we’d better get going.” Just as I expected, she was thoroughly disappointed.

“But sir,” she said, “can’t we have fun just one last time?” I hadn’t had any intention of doing anything after our romp in the woods this morning. I’d already come twice today and had a lonely girlfriend waiting at home. I’ve never cum more than three times in one day before, and thought that four might be too tall a task, even for a stud like me. But I still liked to lead Priscilla on.

“Ok, I’ll make a deal with you. You see this baseball diamond? The distance from home plate to the right foul pole, around the outside of the outfield fence, and back to home plate is roughly a quarter mile. If you can run that in under two minutes, we can fuck one more time.” Priscilla wasn’t exactly athletic, so it seemed like a safe bet, yet not so much that she couldn’t keep it interesting.

“And one more thing,” I added, “you’ll have to run the whole thing naked.”

“Barefoot, too?”

“No, that wouldn’t be very sporting, would it? You can put your shoes on.” Priscilla donned her sneakers and I led her to home plate. Once there, I brought up the stopwatch app on my phone. “Ok, Prissy, on your mark. Get set. Go!”

Priscilla took off down the first base line much faster than I was expecting. I guess good dick could motivate even the laziest of sluts. She started to slow down as she rounded the foul pole and began running around the outfield fence. At first I thought she was out of breath, but then I noticed a slight limp in her stride. This morning’s switching was still taking its toll. Finally, she made it around the other foul pole, leaving just the straight shot to home.

“Fifteen seconds!” I called as she hobbled towards third. With all the effort she could muster, Priscilla broke into a sprint. As her foot touched home plate, I stopped the clock. One minute and fifty-seven seconds. Well, I guess I could spare one more load tonight.

“Good job, sissy,” I said, walking over to where she stood, hunched over and panting heavily. Even after seeing her time, it took a moment for it to register that she’d succeeded. By then, I’d already pulled my dick out and lubed it up.

We had little time for sex, so I skipped the fooling around and got straight down to business. I grabbed Priscilla by the back of the neck and pushed her over to the chain-link fence behind home plate.

“Turn around and grab the fence,” I demanded. “Spread your fucking legs like the slut you are.” Priscilla did so and I took my place behind her. I stuck the head of my dick inside her ass, giving her just a moment to get used to it before I began pumping away.

“Oh, fuck!” Priscilla gasped.

“Shut the fuck up, slut,” I hissed in her ear. “You worked so hard to get fucked, now you’re gonna get fucked just as hard!” This wasn’t about sex; this was about one Alpha male putting a beta cocksucker in their place. Priscilla had the fence in a death grip, her body pressed tight against it as I pounded her ass mercilessly.

As I fucked her, Priscilla was moaning like we weren’t in the middle of a public park. I took one hand off her hips and covered her mouth, muffling the noises.

“We-are-in-public!” I said, punctuating each word with an extra firm thrust. “But that’s what you want, isn’t it? You want someone to see you like this, getting railed out like a cheap prostitute in the middle of town. Imagine it, sissy. Imagine all of these bleachers filled with people, all here to see you get ass-blasted by a real man!”

I got to admit, the thought of that had me almost as aroused as Priscilla was. She panted faster and harder as I fucked her faster and harder, until I could feel her spasming beneath me. Her sphincter tightened around my dick as she orgasmed, gripping my shaft tightly. That sent me over the edge and I once again filled her ass to full capacity with my seed.

As we both came down from our orgasmic bliss, I directed Priscilla to get dressed quickly. We’d already been there longer (and made a lot more noise) than I intended. Within minutes, Priscilla was gone, replaced by Kieran. He picked up the girly clothes he’d been wearing the past two days and followed me as I led him out of the park through a side gate. Sure enough, as we walked up the hill, I could see a cop car pull in through the main gate to investigate the disturbance the neighbors had reported.

I drove us to the house and we went inside. Margot greeted us at the door wearing sweatpants and one of my t-shirts, having been taking a nap since the last time I called her. She hugged me and her brother in turn and asked us how our trip was.

“Boring as hell,” I lied.

“Same,” Kieran agreed.

Since I’d literally just gotten done drilling her brother minutes earlier, I told Margot that I needed a shower after my long trip. To my horror, she decided to join me. The whole bathroom smelled like sex once I’d stripped down naked, but Margot didn’t seem to notice. Later, I managed to set a new personal record for virility when I made love to Margot like I hadn’t been laid in weeks.

Kieran was the perfect guest for the next few days, just like I wanted. He spent most of his time in the guest bedroom with the door shut. Margot made the obvious jokes about him masturbating in there and I laughed along, knowing that she had no idea what kind of depravity he was really up to. With Margot around, I never fucked him again, though I managed to get one last blowjob out of him when I drove him to the airport to send him back home while Margot was at work. But that’s a story for another time.

Published 
Written by MarkSunset
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