Road Trip with a Sissy - Day 03

"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 The shy virgin that had muffled her moans in the motel mattress as I deflowered her last night had been replaced by a cock-crazed slut whose screaming echoed in the silent forest.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 phone." 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 any thing 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 a song, 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 came 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.