Road Trip with a Sissy - Day 03

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 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 were 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." Priscilla kicked her feet, sending her flip-flops flying across the clearing. 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.

"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 wasn't 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.