My alarm went off way too soon. Last night’s festivities had seriously cut into my sleep time and I was exhausted. Much as I wanted to sleep in, we still had a lot of miles to go today. I only had a couple quick stops I had to make before we hit the open road.

I got up to see Kieran asleep on the other bed. He was lying on top of the covers, still completely naked from the night before. The spanking I’d given him had left his ass too sore to sleep on his back, so the sight of his bare, pink ass was the first thing that greeted me. I gave his backside a hearty slap. He woke up with a start and looked up to see my erect penis hovering nearby. As he stared hungrily at it, I ordered him to get dressed and in the truck in five minutes.

I stopped by a coffee shop and got us breakfast, though Kieran had already fallen back asleep in the passenger seat. With him preoccupied, I drove to the nearest Wal-Mart to pick up a few “supplies” for the rest of our trip. Even though I was in a mostly empty store hundreds of miles from home, I opted for the self-checkout line to avoid any strange looks I might get.

Back at the truck, I woke Kieran up and ordered him to get out of the car. Even if I didn’t have the video, I knew he didn’t have the spine to stick up to me after the spanking I’d given him the night before.

“I bought you a new outfit,” I said, handing him one of the bags (the other bag was for later). “Why don’t you try it on?” Kieran knew that it wasn’t really a request, but he still balked as he pulled the clothes out. I had bought him a white crop top, denim short-shorts, black bikini briefs, and pink flip-flops. He tried to protest that he didn’t want to wear them, but I told him he could wear them with or without another ass-whupping right there in the parking lot. He tried to get back into the truck to change there, but I shut the door and locked him out.

Kieran begged me to let him change inside the truck, but I refused to let him, telling him that I had parked in a remote part of the parking lot and there was nobody in the immediate vicinity. He was still unconvinced, but I told him that the longer he waited, the more people would start to arrive and the more likely it was that someone would see him. Defeated, he began kicking off his shoes. He stripped off his T-shirt and immediately replaced it with the crop top. With one last quick look around, he dropped his jeans, revealing that he’d gone commando after I had prohibited him from wearing his mother’s panties again. He slipped the panties up around his hips, then pulled up the shorts. I took his clothes and locked them up with our luggage.

Before I let him get into the van, I had him turn around to get a complete look at him. He really did look like a girl now that he was dressed up like one. Except for his lack of boobs and his slimmer hips, he could have passed for a younger version of his sister. Satisfied, I unlocked the door and we drove off. Now that he was out of the open, he began to relax again. I noticed him glancing over at the bulge in my own jeans that had developed watching him change.

“Still drooling over my dick?” I asked. He blushed a little bit, but to my surprise, he actually nodded.

“Yes, sir,” he cooed, “I want to suck your dick again.” After last night, I thought his curiosity for cock-sucking had been satisfied, especially as he cringed while I coated his face with cum. But apparently I’d only whetted his appetite.

“Such a naughty girl!” I said. “If you want it so bad, you have to beg me for it.” I never would have dared make Margot beg me for anything sexual, but Kieran was so eager that I could demand anything from him.

“Please, sir! Let me suck your cock again.”

“I will, but only if I cum in your mouth this time.”

“Yes, sir,” he replied, as if he hadn’t been the least bit squeamish when I’d nutted across his face last night.

“And you better swallow every…last…drop,” I told him, deliberately punctuating the last three words so he knew that it was non-negotiable. I guess he hadn’t expected that, since he paused before speaking again.

“I will, sir,” he said.

“Good, because I won’t have you spilling any jizz on my seat.” His eyes widened in surprise.

“You want me to suck you off in your truck? I thought we were going to wait until we got to the motel.”

“That’s still a long way away. I don’t think a little sissy cocksucker like you could wait that long.”

“But what if someone sees?”

“So?” I asked bluntly. “No one’s going to be staring into my truck while they’re doing 80 down the interstate. Even if they did, it’s high enough off the ground most people wouldn’t be able to see you as long as you keep your head down.” That was enough to convince him. He laid down across the front seat and reached for my belt. Immediately, I grabbed a handful of his dark hair and pulled upwards, causing Kieran to squeal in pain.

“What?” he whined.

“I didn’t give you permission to take it out. Don’t ever forget who’s in charge here.”

“I’m sorry, sir,” he said, “may I please take it out?”

“Yes, you may.” He didn’t need to be told twice, as he undid my belt, unzipped my jeans and pulled my throbbing cock out of my boxers. If he was in awe of it in a dimly lit motel room, it was nothing to how he stared at it in the light of day.

“Your cock is amazing!” he said. “Can I suck it now, sir?”

“Go ahead, sissy.” He leaned forward and took the head into his mouth. “That’s it. You were born to be a cocksucker.”

Since I was preoccupied with driving, I let him do as he pleased for the most part, only taking my eyes off the road for a few seconds at a time to watch his head bob up and down in my lap. Fortunately, he remembered most of the instructions I’d given him last night and didn’t need too much supervision.

Kieran had one dainty hand wrapped around the base of my cock, stroking everything that his mouth couldn’t reach. He started sucking on each of my balls in turn, then ran his tongue up the length of my shaft before taking it all in his mouth again.

Meanwhile, I was in heaven. It had taken forever for me to convince Margot to go down on me (and much longer for her to actually get good at it), and she’d never do it while I was driving, for fear of me crashing or someone seeing her. But here was her younger brother, giving me road head like a pro without the slightest concern. That’s when I realized that my plan for Kieran was making him to do all the things that Margot would never do. After all, why else would a straight man want another man sucking him off?

“Such a good sissy,” I praised, nearly breathless. “Hey, I just had a thought. My sissy needs a name. What should I call you, sissy?” Kieran didn’t answer, he just kept at it like the good little cocksucker he was. “What about Kiera? No, too obvious. I know! Your name can be Priscilla! Prissy the Sissy! Do you like that name?”

“Yes, sir,” he said, taking his mouth off my cock just long enough to answer before going right back to work.

“I want to hear you say it,” I ordered. “What’s your name, sissy?”

“My name is Priscilla.”

“Good girl,” I said, pushing “her” head down. Like the naughty slut she’d become, Priscilla wrapped her pretty lips around the head of my dick, stroking the shaft with one hand and cupping my balls with the other. As she worked her tongue around my knob, I could feel myself approaching orgasm.

“Remember what I said, Prissy,” I said breathlessly, “you swallow every drop or I’ll whup your ass raw.”

“Yes sir,” she replied, continuing to stroke even as she took her mouth off my cock for a split second. She was barely able to get her lips tight around the head before I started erupting in her mouth. Priscilla gulped down the jizz as fast as she could, nearly choking and spitting it back up before she was able to down it all. It was a good thing I’d nutted the night before; there was no way she’d have been able to swallow that much cum at once her first time.

“Wow, you’re salty,” Priscilla said, making a face as she got the last of it down. She grabbed the coffee I’d bought her for breakfast hours again and gulped down a mouthful. I’ll take it as a compliment that she gagged harder from the coffee than she did from my semen sliding down her throat.

“That ought to hold you over for a few hours,” I said. “If you’re done with it, put it away.” Gently, Priscilla tucked my now-flaccid cock back in my boxers, though not before taking a few more seconds to stare at it.

“Even when it’s soft, yours is bigger than mine,” she said, a mixture of admiration and envy. Prissy zipped up my jeans and slid back into the passenger’s seat. Even as aroused as she was, the bulge in her own jeans was barely noticeable. I ignored it and we drove on in silence for the next few hours.

“Sir,” Prissy said suddenly, “I need to use the bathroom.”

“We just passed a rest stop a few miles back,” I said, irritated. “The next stop is about 30 miles up the road.” She groaned.

“I really need to go!” She gave me the same sad, puppy-dog eyes that her sister always used when she wanted something. I rolled my eyes and pulled off onto the shoulder.

“Make it quick,” I said, not wanting to lose any more time than necessary.

“Right here, on the side of the road?” she asked.

“Just squat next to the car, no one will see you.” Priscilla just looked at me in disgust, so I added, “If you think you can hold it until the next stop, fine. But if you piss yourself in here, I’m going to beat your ass on the side of the road and post it online.”

She hopped out of the truck in a split second and slid her shorts and panties down past her knees, squatting down just out of sight to take care of her business. When she got back into the truck a few minutes later, she was blushing a deep shade of crimson.

“Thank you, sir,” she said, not even looking at me. I wasted no time getting back on the road, and we road for nearly another hour before Priscilla spoke up again. “Sir, would you really spank me again?”

“You want to try me?” I replied. She shrugged and waited a minute before continuing.

“Actually, I was kind of hoping you would,” she said, averting my eyes the way she always did when she was embarrassed by what she was saying.

“What?”

“I mean, it really hurt, but after a while, I started to enjoy it.”

No shit, I thought, remembering how Kieran had busted a nut while over my knee the night before. Still, it was surprising that the little sissy would find getting her ass beat to be enjoyable. Margot liked it when I slapped her on the ass, but nowhere near as hard as I was giving it to her brother last night.

“If I spank you,” I said, “it’s definitely going to hurt like hell. You better be really sure that’s what you want because once I start, I’m not going to stop until I decide you’ve had enough.”

“I’m sure, sir. I want you to spank me again.”

“Well, it’s gonna have to wait until we stop for the night. And don’t even think about changing your mind, because you asked for it and you’re going to get it good and hard.”

Just talking about it had my dick starting to get hard once again. I needed to stop to get gas anyway, so I pulled into a gas station and parked in the most isolated part of the parking lot.

“Are you thirsty, Prissy?” I asked. She nodded. “Good, you can go in and get us some drinks. But first, I have something else for you to guzzle down.”

I undid my jeans and pulled my cock back out.

“Here, sir?” she asked nervously, looking around.

The station wasn’t too busy, and everyone there was too busy to pay much attention to the truck parked in the farthest spot from the door.

“Yes, Priscilla. You’re going to suck my dick right here in the parking lot. Then you’re going to walk right into that convenience store and buy us something to drink. But here’s the catch: when I cum in your mouth, you’re not allowed to swallow it until you get back.”

She looked unsure about that, but I grabbed her hair and dragged her across the cab, forcing her head down into my lap to show her that I wasn’t asking.

In seconds, I felt her wet mouth back around the head of my cock. Just to remind her who was boss, I held her head in place and thrust my dick up into her throat, causing her to gag.

“That’s right, bitch!” I taunted, “Choke on that fat dick!”

I had to admit, I was more than a little nervous myself that someone would discover us, but that only added to the eroticism. There was just something about sitting in broad daylight, ramming my cock into the back of that barely legal sissy’s mouth while total strangers stood barely thirty feet away that drove me wild.

I let Priscilla come back up for air, a string of drool running from the tip of my dick to her mouth. That earned her a slap on the ass as I ordered her to lick it up before getting back to work. The spank was much louder than I anticipated, and I nervously looked around to make sure nobody had been alerted as to what was going on. Like me, everyone else seemed much too preoccupied with getting back on the road as soon as possible to pay much mind to what anyone else might have been up to.

A few minutes later, I deposited another load into Priscilla’s waiting mouth and had her show it to me before handing her a $5 bill and sending her into the store. I swung the truck around to one of the pumps and filled up the tank. Priscilla came back a few minutes later with a couple of bottled drinks in a plastic bag, lips shut tightly as if afraid to let a single drop spill out.

“Alright, open up and let me see,” I said.

She looked around nervously before opening her mouth, showing me a large pool of cum resting on her tongue.

“Swallow.”

She gulped down the cum, extending her tongue from her mouth afterwards to show me it was all gone.

“Good girl.”

We both got in the truck and got back on the highway, where Priscilla gave me an account of her first foray into public. Her appearance had apparently attracted several curious stares from the other patrons, presumably because she was androgynous enough to keep you guessing. Then there was the challenge of trying to check out with a mouthful of cum, forcing her to communicate with the cashier solely nodding or shaking her head.

The rest of the day’s trip passed uneventfully. As we neared the motel, Priscilla got quieter, either from excitement or dread about her upcoming spanking. I couldn’t help but add to her anticipation by talking about it.

“Won’t be long now, Prissy,” I said. “Soon you’ll be over my knees, bawling your eyes out while I beat your ass red. I can already feel it in my hand.”

Priscilla squirmed uncomfortably in her seat, as though she too could already feel the spanking to come.

“Nervous? A little too late for that. You asked for this spanking, so you’re going to take it like a good girl.”

A few minutes later, I pulled into the motel’s parking lot. After checking in, I told Priscilla to wait in the corner while I ran to the ice machine. I filled the bucket from our room with ice and walked back to find Prissy still where I left her. While she waited, I filled a plastic bag with ice and wrapped it in hand towel from the sink, making an impromptu ice pack.

“Alright, Priscilla,” I said, “get over here.”

Priscilla walked over from the corner as if walking to her own execution. I ordered her to place her hands on her head and when she did, I unbuttoned her jeans and slid them down to her ankles. Her panties were strained from trying to contain her tiny erection. I pulled the front of her panties outwards, slipping the ice pack into the crotch. Priscilla flinched when the cold cloth touched her genitals, which quickly shriveled up.

“I’m not going to have you cum on me again,” I explained, remembering last night.

I’d had three orgasms since she had had one, and I didn’t trust her to have any self-control. Satisfied that there wouldn’t be any mishaps, I swept her over my knees, pulling the back of her panties down below her ass cheeks.

SMACK! My first blow caught Priscilla by surprise, but I wasn’t about to give her time to recover before the next one. SMACK! SMACK! SMACK! Priscilla was squirming now, but not so much that I had to restrain her just yet. SMACK!

“How are you doing, Prissy?” I asked, giving her another smack as I did so.

“It hurts, sir.”

“Spankings are supposed to hurt, Prissy.” I gave her a dozen more spanks, alternating cheeks, before Priscilla finally tried to block with her hand. “Oh no you don’t.”

I grabbed her skinny wrist and wrenched her hand to the small of her back, spanking her even harder for her resistance. Priscilla squealed as her ass turned a brilliant shade of pink.

“Stop your whining,” I ordered. “You asked for this.”

Tears were streaming down her cheeks now, and before too long, she stopped struggling and just accepted the spanking that she so richly deserved. I stopped and had Priscilla get back to her feet.

“Alright, Prissy,” I said, “strip down naked and bend over the bed.”

Priscilla stepped out of her shorts, slid her panties the rest of the way off, and took her crop top off, tossing it onto the pile on the floor. That earned her a heavy slap across her ass.

“Pick up those clothes and fold them!” She bent down and picked up her clothes, folding them as best as she could and placed them on the nightstand, sobbing all the while. As she moved towards the bed, I started undoing my belt and pulling it through the belt loops. The familiar sound of leather on denim was one I had learned to dread when I was young. Priscilla caught a glimpse of me doing so as she went to bend over the bed and gulped. But I was the one that was in for a shock when I saw what happened next.

Priscilla bent over the end of the bed as ordered, but without being told, she reached behind her with both hands and spread her ass cheeks apart.

“What the hell are you doing?” I demanded.

She immediately realized that she’d made a mistake, but there was no way that she could deny what she’d done.

“You told me to bend over the bed,” she mumbled, “and when I saw you taking your belt off-“

“You what? You thought I was going to butt-fuck you?! No, I’m going to whip your ass raw with my belt! You got that?”

“Yes, sir,” she said, now blushing a deep crimson.

“You got ten strokes coming. After each one, you’re going to count it out loud and thank me for disciplining you.”

“Yes, sir.”

CRACK! I brought the belt down with full force across Priscilla’s tender backside. She squealed in pain before she remembered my command.

“One, sir. Thank you for disciplining me.”

CRACK!

“AAH! Two, sir. Thank you for disciplining me.”

CRACK!

“Three, sir. Thank you for disciplining me.”

CRACK!

“Four, s-sir! Thank you for disciplining me.”

CRACK!

“Five, sir. Thank you for disciplining me.”

CRACK!

“Six, sir! Thank you for discipling me.”

CRACK!

“AAAAHHH! Seven, sir. Thank you for discipling me.”

CRACK!

“Eight, sir. Th-thank you for discipling me.”

CRACK!

“Nine, sir! Thank you for discipling me.”

CRACK!

“Ten, sir! Thank you for discipling me!”

Priscilla was sobbing into the blankets now. I stepped back to admire my handiwork. The stripes I’d just applied across her ass were already turning a dark shade of red than the rest of her backside. Her flaccid dick was just visible between her legs, pressed against the edge of the bed. It was then that I became aware of my own throbbing erection.

My mind immediately went back to a few moments ago when Priscilla had willingly offered up her ass to me. I had managed to push the thought from my mind while I was giving her the belt, but now that the beating was done, it was all I could think about. For the first time since I’d caught Kieran in the bathroom last night, I was questioning my arousal.

Despite the girly figure and feminine clothes, despite the most effeminate name I could come up with and despite the fact that I’d constantly calling her a “she”, I couldn’t deny that the person lying naked before me was another man. I had been able to deny it while I was getting a blowjob because I couldn’t see any evidence of Kieran’s true gender. I wanted to end things right there, to tell Kieran to get dressed and both of us to go to bed, but I was too horny.

I walked up to Kieran and grabbed his whole ass cheek in one hand, squeezing the supple flesh. He winced, thinking I had decided to continue his punishment. Maybe in a way, I had, but that wasn’t my true intention.

“You dirty little slut,” I whispered in his ear. “Spreading your ass cheeks for me like that. Did you really think I was going to fuck your ass? Or were you hoping I would?”

“I don’t know,” came the reply. “After everything we did today, I thought you might. So when you made me bend over the bed and started undoing your belt, I just thought that’s what you wanted.”

“And what does this sissy want?”

“I want you to take my anal virginity, sir,” she quickly whispered, as if trying to get it all out before she could change her mind.

I sucked on one finger from my free hand to lubricate it and stuck it into her tight, virgin asshole. Priscilla winced as I penetrated her.

“Don’t clench,” I said. “It’ll feel better if you relax.”

She eased up a bit, though she was still too tight to just stick it in. That’s when I remembered the bottle of lube I had in the truck from my last camping trip, when I was hoping that I could convince Margot to do anal.

“I’ll be right back,” I said. “Stay right there.”

I stepped out of the motel room and retrieved the lube. Just as I instructed, Priscilla hadn’t moved a muscle since I’d been gone. While she waited, I set the lubricant on the nightstand next to the bed and stripped naked. I decided that she was too low to the ground bent over the edge of the bed, so I had her get on her hands and knees so that her ass was just the right height.

I opened up the lube and squirted a liberal dosage on her exposed asshole, working it into her with my finger. At first, I could only fit one finger, but after a few minutes of work, I loosened her up enough to stick two fingers inside her. She moaned softly now as I continued to gently finger her.

“How are you doing down there, Prissy?”

“Good, sir,” she cooed.

“Are you ready for me to stick it in?”

“Yes!” Priscilla moaned.

“I want to hear you beg for it.”

“Please fuck my ass, sir,” Priscilla begged. “Please stick your fat, juicy dick in my tight sissy ass!”

I was surprised by how much of a slut she had become with a little persuasion. I lubed up my dick generously and stepped into place behind her, pressing the head up against her tight sphincter.

“Ok, Prissy,” I said, “this is going to hurt at first, but just relax and it’ll start to feel good.”

I pressed the head of my dick into her asshole. She started to whimper in pain as my thick member started to stretch her out. I pushed a few inches inside of her, her tight ass gripping my dick like a vice.

“Aaargh!!” she cried. “It hurts, sir!”

“Shh, it told you it would hurt.”

I gave her a few moments to get used to it before I started pushing my way deeper inside her. She tried to get away, but I grabbed her firmly by the waist and pulled her back, impaling her even deeper until the full length of my cock was inside her.

“I can’t take it, sir!” she whined.

“You already have,” I said, “I’m all the way inside of you now.”

I paused to give her time to get accustomed to its girth, and to catch my own breath, since she was so tight it was making my head spin. As soon as it cleared, I pulled my cock back until just the tip was inside Priscilla and then rammed almost the entire length back in with one strong thrust. Priscilla yelped in pain as I drove my cock into her, but I didn’t give her any time to recover before the next thrust.

I settled into a slow but steady rhythm, the same tempo I used when I was trying to be sensual with Margot. Priscilla whimpered as I gently pounded her ass, my dick sliding back and forth with ease from the generous amount of lube I’d used. I soon heard her whines turn to moans as the pain subsided and the feelings of pleasure she experienced soon took over.

“How does it feel, sissy?” I asked.

“It-oh fuck,” she gasped, “it feels so good, sir! I can’t believe, urgh, how amazing your cock feels, ahh, in my ass!”

“You little cumslut!” I laughed. “I can’t believe you were a shy, little virgin just a few minutes ago. Tell me how much you love taking it up the ass.”

“Oh, fuck! I love the way you fuck my ass, sir! Please fuck me harder!”

“Say no more, sissy,” I said, immediately pounding her ass with the same ferocity I used whenever Margot let me fuck her hard.

Soon, the sound of Priscilla’s ass cheeks getting clapped filled the air, mixed with the rapid panting of her breath as I fucked her senseless.

“FUUUCK!” she exclaimed, shuddering as I drilled her ass relentlessly.

I could see her hands gripping the sheets so tightly that her knuckles her white, her face pressed into the mattress to muffle her moans.

“Oh, fuck yes!” I exclaimed. “Your sissy hole feels so good, I could fuck you all night!”

I slapped her already sore ass cheek, making her flinch.

“Let me get up on the bed and really start fucking you!”

Without pulling out, I managed to step both feet onto the bed, pulling Priscilla’s hips even higher above her head and thrusting in at a downward angle. She moaned louder than ever.

“Oh God! You’re gonna make me cum! You’re gonna make me cum!”

That was my cue to fuck even harder and faster, the same way I did whenever I knew Margot was close.

“OH FUCK!” Priscilla shuddered underneath me, and I heard something wet dripping on the bed. Guess that decided who would sleep on what side of the bed.

Priscilla’s knees went weak from her hands-free orgasm, and with one powerful thrust, I pushed her flat onto the mattress beneath me. I barely even broke my rhythm, as I continued thrusting downwards into her ass. I could feel myself building to my own orgasm quicker than I expected, since I’d already came twice today.

Priscilla started to stir beneath me. I guess she wasn’t enjoying the sex anymore, whether because of the new position or because she’d already came, but it turns out neither was the case.

“Oh God, what are you doing to me?” she asked. “It feels so fucking good! I think I’m gonna cum again!”

And to my amazement, she did just that, releasing her second load in just a matter of minutes. She must have really gotten herself hot and bothered today. The feeling of her sphincter tightening as she orgasmed sent me over the edge.

“Good job, sissy!” I growled in her ear. “Here’s your reward!”

And with that, I pumped a massive load into her tight asshole.

“Oh, wow,” she said, “I can feel it inside me! It’s so much cum!”

I grunted in agreement and slowly withdrew my cock from her ass with a sucking sound. I rolled over and sat down next to Priscilla, who soon got off her belly. There was a large puddle of jizz on the edge of the bed, soaking into the blanket.

“You’re sleeping on that side of the bed, so you might want to clean that up,” I said.

She looked around the motel room.

“They didn’t give us any tissues, sir,” she said, looking back at me.

“You have a mouth, don’t you?”

She got down on her knees and started slurping up her own cum from the bed.

“It tastes different than yours, sir,” she reported, as if I cared to know.

I suggested that we both take a shower and get some sleep. The shower was too small for both of us, so I let her go first while I called Margot to update her on her trip.

An hour later, after I’d finished lying to my girlfriend about the day’s events, I showered myself and crawled into bed next to her sissy brother. Like the night before, he was lying on his stomach because his ass was too sore, though in more ways than one tonight.

“I can’t believe you made me cum from fucking me in the ass,” Kieran said, no longer Priscilla now that we were both spent for the day.

Now, he was just the timid, vulnerable young man who was just now coming to terms with the fact that another man had just taken his anal virginity and he’d loved every minute of it.

“Yes, I did,” I replied. While I was starting to question my own sexuality as I thought about what I’d just done, I felt a good deal of pride at my sexual prowess.

“I can’t believe we just did that,” he said, shifting over to look at me. “But I’m glad you were the one who popped my cherry. I can still feel your cum leaking out of my ass. Do you think we can do it again tomorrow?”

“I don’t know,” I said. “We’re going to be at the house tomorrow evening, and we probably won’t have time in the morning.” I could tell he was disappointed. “But don’t get too upset. I have plenty of ideas for tomorrow.”

And with that, I rolled over and went to sleep, leaving Kieran to stay awake trying to guess what I had in store for him next.