Kissing his skin again, I didn’t want to have this conversation while my tongue was centimeters away frompunching inside his ass and opening him up. “Tied up, punished, those are the types of submissives I attract,” I said, planting my kisses on his inner thigh until I was on my knees in front of him. I tapped my heavy dick against his, like two swords. His had a little curve to it, and mine was straight like an arrow—with just as much of an aerodynamic head. “You’re different,” I said. I’d been trying to tell him that. “You make me more controlled, you let me play a role I’ve wanted to explore for a long time.”
He pushed his cock up against mine, as if combating me—it was adorable. This was all so different, and I had to take these moments in, because I didn’t know how many more I’d get. He was singlehandedly scrubbing away all the boys that had come before him.
There was no more waiting. I had lube and condoms in my nightstand—both sides of the bed. There were a collection of novelty ones, glow in the dark, flavored, some even with the ability to leave the tackiest looking washable tattoos on the shaft. Isaiah picked the glow in the dark, immediately curious and with those big eyes that begged, asking for permission to roll it down my cock. He did it well, with encouragement and guidance. “Good boy,” I whispered, stroking my thumb and fingers on his face like you would a kitten. “No, lie back, relax, and don’t tense, you might tear your ass.”
“What?” he mustered.
“It’s happened,” I said. And I think I’d seen more blood on the bed then than I had after a shooting. I smiled. “Relax, baby.”
He chewed on his bottom lip, laying his precious head against the pillow.
I warmed the lube up in my hand before applying it to his freshly eaten ass. I grabbed his legs by the thighs and pulled him slightly so his back was up on my knees. “You wanted this,remember,” I whispered as the thick head of my cock pushed inside him.
Isaiah’s mouth opened wide, no sound. His eyes rolled back, and after a second of me teasing his hole, he moaned. It sent a body-shaking shiver through me, to the point I pushed the entire head inside and found him loosening up rather nicely around me.
“You like that?” I asked. I’d never checked in as much as I was right now, making sure his pleasure was perfect, and that I was just the tool to deliver it to him.
He moaned so sweetly, like he was trying to hold them in, and when they came out, they were just peeps of sounds. I fucked him in missionary for a moment, and then flipped him over for better access. He lay on his belly, ass perked up, wiggling for my cock. I applied a little more lube to the tip, rolled it down the shaft, and let him feel it as it slowly stretched him again, his moans now muffled into the pillow.
“Harder,” he whispered, his head turning from side to side on the pillow, moaning.
Laid out on his back, my entire body covered him, elbows on the mattress and my knees pushing his legs out. He was truly splayed out for my benefit. “You like it this way?”
He nodded. “Yes, Daddy.”
Soft and slow strokes, I was controlled. One of my biggest struggles was control, and yet around him I found control easy. I was controlled enough not to have torn his clothes right off him when he walked into the penthouse. As I thrust my hips and my cock went deeper, I was letting out deep grunts, almost harmonizing with his.
“Daddy,” he let out. “I might come.”
In this position he was being rubbed up and down the bed, his cock no doubt taking most of that friction. “Come,” I demanded from him. “Make your pretty little hole tighter.”Almost like I punched a come button in his ass, several thin strings of cum shot out across the length of the bed. His hole tightened, warmer now, and my control left as I went as deep as my hips in his ass would allow my cock to dive. I unloaded into the condom, and lay right there on top of him, my cock letting out these tickle twitches inside him.
That was... better than expected. Now his ass would need to recover, and he would have to decide to stay. I made sure he got all the TLC he needed for that ass’s recovery—a little cream, and a little kiss, but not in that order.
7. ISAIAH
We both went back tomyroom where we slept, since we’d made a mess in his, and he said something about a housekeeper coming to clean in the morning. It was the first time I’d shared a bed with someone overnight—but bonus points went to him being a cuddler, like my teddies, and giving me the occasional kisses in the middle of the night.
My ass, like he’d said, was sore as fuck. Balls. No adult words. It hurt, a lot. Part of me wondered if I was bleeding, or if it would always feel that way—just like something was missing from me now. I could understand why people would have sex with him and then leave the following day. He was dangerous, but danger was hot sometimes. I’m sure there were a lot of rumors around about him too, and if I were part of those circles, maybe I’d have known about the beer can of a cock he was weaponizing against the twinks of Boston.
I woke to the smell of something sweet in the air, and then a gentle rap of knuckles at the door. I noticed Santo wasn’t in bed anymore, and the curtains were blackout blinds, closed just enough for a trickle of light to appear in the middle.
“Hello,” I called out with a croak in my voice.
Santo, dressed in gray sweats—freeballing, the dick imprint had my eyes fixed on it—walked in with a blue plastic plate in his hand and a smile on his face. “I thought you woke when I did,” he said as light from the hallway spilled in, forcing me to shield my eyes from it. “Come on, we’ve got a big day.”
I felt well rested. It must’ve been... eight hours after, I don’t know.That was something strange about this place, there were no clocks, and my phone seemed to disappear from wherever I’d put it. It wasn’t like I wanted to see my phone or the fucked-up shit my mom might’ve been saying to get me to sendher money—once, she’d told me she was going to die, and I took it to mean suicide, but no, she was just hungry. Fuck. Shit... balls. No adult words.
“Thinking?” he asked, placing the plate on the bed. There were crepes, folded on one side, a well of melted chocolate and a section was filled with mixed berries—mostly strawberries. “You want a coffee or juice?” he asked.
I just nodded. “I’m—”
He sighed. “You want to leave?” he asked. “You can. I told you this. Anytime you want.”
I rubbed the bracelet around my wrist. “No, I—no. I don’t want to leave. But I’m—kinda scared.”
He nodded. “Rightly so. There’s a whole fuck ton of shit out there to be scared about. But here, now, there’s nothing for you to fear. I mean, you’ll have to make coffees and do your usual duties when we’re outside, that’s your job, but here, now, this is what I’m doing for you. Anything outside of those things, don’t worry about them. You’re mine, and because of that, you’re protected.” He reached out to my hand with the bracelet on and gave it a little squeeze. “And you can leave. I’ll even get my driver to take you home.”
I shook my head. That was a lot of words to process all at once. “I understand, and I—I wanna stay, but since we—”
