Road Trip with a Sissy - Day 02

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 turned 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 get herself 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 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.