I got him in place, with his stomach supported and knees resting on one set of pads and his arms settled onto the others. I tugged him just enough to make sure his cock hung clear and couldn’t touch anything. Securing all four limbs, I carefully tested their hold.
His breathing was already a little rough, and my cock responded, perking up already. I ran a hand down his back, over the pretty line his spine and ass made, then back up again. He moaned softly, so I did it again, enjoying just touching his skin.
“You have beautiful skin, boy. It’s going to be even prettier with welts crisscrossing it.” I cupped his ass and squeezed, and he moaned again. I leaned over him, covering his back, and pushed his hair aside, then nipped at an earlobe. “Do you want to end this later with my cock in your ass, boy?”
He groaned. “Oh fuck yes, Master.” He writhed in his bindings.
I nipped his lobe again and hummed in his ear. “If I was more of a sadist, I’d work this beautiful body up, fuck you within an inch of your life… and deny you orgasm completely.”
He groaned. “I wouldn’t mind, Master.”
I shifted, bringing my hand down hard on his ass. “Did I ask a question, boy?”
He jumped and shook his head quickly. “No, Master. I’m sorry, Master.”
“Forgiven, this time.” I moved around front and squatted in front of him. “What are your safewords, boy?”
“Cherry and lemon, Master,” he said, breath hitching.
I kissed him softly on the forehead, then stood and stepped back. I glanced up to see Sammy and Cam on the sofa next to us. Cam’s head was in Sammy’s lap and the rest of him was under a blanket. I nodded to them, then went to my bag and brought it over to the table next to us. I shifted the table out of Kyle’s line of sight. I didn’t want to give him the chance to anticipate anything. I hoped I’d manage to get him to fly tonight, and I was going to use every trick I had to make it happen.
I hadn’t brought a lot of different toys with me, but I was pretty sure what I had would still do what I wanted it to. I took out the paddle and crop and set them aside; they were a given. Next came a pretty leather piece with two straps that made more noise than pain. I set that next to the paddle. Brushing my fingers over the split-leather strap tawse made me decide to simply lay them all out. The two canes I had were last placed onto the table.
But before I used any of those, I stepped back up to my boy and ran my hand over his ass, squeezing and massaging, getting it sensitive. Then I lifted my hand and brought it down hard on the cheek opposite the one I’d swatted earlier. He grunted but otherwise stayed quiet. In the mirror, I could see his face, and I watched it carefully as I gave him four more quick, hard swats, alternating cheeks. He jumped slightly, grunting again, and his ass flexed. I reached down to feel his cock softening a little, so I stroked it back to full hardness before smacking his ass again.
He already had a bit of distress on his face, and I thought it looked lovely. Each new swat made it a bit more obvious until his face was starting to blush with the effort.
I scratched my nails over his sensitive skin and leaned in to him. “Let out your sounds, lovely boy. Your reaction is what I want most.”
He nodded and swallowed, letting out a small moan.
I kissed him again, then went back to his ass. I let loose a volley of swats too quick for him to recover between, alternating some but not evenly. His left cheek was going to be a lot sorer than his right, for now.
He let his sounds flow, not loud but still enough for me to hear. I knew he was worried about the rest of the dungeon; they usually preferred quiet. But it was busy enough tonight, I knew that wasn’t going to happen.
Once more I stepped up to his face. “Let me worry about too much noise, boy. You just let go and feel. All right?” I tagged that onto the end because I wanted a verbal reply.
“Yes, Master,” he moaned.
I nodded, then moved back to the other side of the bench. I went at his ass one more time with my hand and was pleased when his moans came out louder. His cheeks were taking on a nice rosy shade, and I knew it was time for more.
I considered the options, then picked up the paddle. The foot and a half of solid wood was rounded on the end and slightly on the sides so it curved outward instead of being flat. I lined up, pulled back, and brought it down right in the middle of the fat of his ass, where I’d just been spanking with my hand.
“Ah!” Wide eyes and a jump in his bindings accompanied the shout. He struggled for a moment, face reddening, and I let him assimilate the hit. When he breathed again, I gave him another swat, below the last, pulling another shout and jump from him.
He panted hard and I rubbed both cheeks, working the pain deeper into his muscles and easing it a bit. Then I set the paddle down. I picked up the crop and tapped it lightly on the insides of his thighs. His legs were spread at a lovely angle, giving me access to both his inner thighs as well as his cock and sac. I fondled his balls with one hand while I kept up the lightest of taps with the crop, down to the inside of his knees, then back up, almost to his balls again.
When he melted into the bench, I lifted the crop and gave him a much harder hit, right on the sensitive inner thigh I’d been teasing. He grunted and his legs twitched, but the bindings held him fast. I left a series of these harder hits along his left leg, then his right. I reached under, stroking his cock a few times to make sure it was as hard as I could make it, then tapped his balls with the crop too.
This brought a louder moan from him, and in response, I smacked them harder. He jumped, but his slight movements made me think he was trying to push
into
the hits, not away. When I looked up at his face in the mirror, he wasn’t flying—yet—but I could tell he was starting down that road.
I went after his balls again, increasing the strength of the hits until he shouted and jumped at each one. Letting his balls fall, I put the crop back and unhooked the flogger on my belt. I ran my hand over his back and ass, then raised the flogger and brought it down over his back.
I let myself fall into a rhythm with it, moving around for different angles. I spent time focusing on his sore ass and legs, then up over his back again. I kept an eagle eye on his face, watching him closely, hoping I’d be able to see when he flew, if he did.
By this point my cock was so hard, I wasn’t sure how much longer I could go. I wanted him to fly badly, but I also had my own limits. And I didn’t want to risk actually
harming
him because I didn’t know him well enough to know how much he could really take. He didn’t look like he was close to safewording, but I wasn’t 100 percent sure he would when he needed to. He seemed to know the importance of safety, but I was well aware that some subs fought against using one, feeling like it was a failure to do so.
Moaning almost constantly now, he shifted in his bindings. I ran a hand over the pretty marks on his back, then down over his hot ass. His sounds got a bit louder, and when I looked in the mirror, he looked a little fuzzier but still not gone.
I dropped the flogger onto the table and picked up my favorite cane. I swung it once to get a feel for it again, then lined it up to the crease between his ass and his legs. When it came down, I held it there a brief second, then let go, savoring the line it made on his skin. He moaned loudly, and I added another stripe above the last. I loved how he writhed on the bench as much as he could in his bindings. Encouraged, I picked up the pace, hit harder, laying an impressive series of stripes over his ass and thighs, down to his knees, then back up to the top of his ass. Each one pulled a louder moan than the one before.
Then I saw it. His face took on an almost dreamy quality, and I knew he was flying. That never ceased to make me feel fucking incredible, to know I’d done that for him.
I gave him two more hits, then tossed the cane aside and snatched up condoms and lube. I stepped up behind him, thrilling in the heat I felt coming off his thighs and ass.
I rolled a condom onto myself first, then put one on him before opening the lube. I drizzled some down his crack and rubbed it over his hole before pushing a finger in. Even relaxed, he was tight, and I briefly wondered if I would hurt him by fucking him. I shoved the fear back and focused on stretching him as much as I could. He continued to moan as I did it, getting even louder. I stopped to grab two more things out of my bag, set them on the table, then went back to opening him up.
Finally, I knew I couldn’t do any more. I’d just have to be careful. His sounds were approaching shouts. I grabbed the two things I’d taken out and leaned over him again. I pushed a small red ball with a bell inside into his left hand.
“Drop that if you need to stop me.” When he nodded, I took the ball gag and pushed it between his teeth. I buckled it in place loosely, then grabbed a fistful of hair and used it to hold his head up, tilting my head at the mirror. “Watch us, boy. Watch as your Master fucks your ass hard.”
He moaned again, and I slicked my cock one-handed and lined up, steadying it with my free hand. I pushed slowly against his hole, his sphincter still resisting despite him being relaxed and stretched. I took a breath and kept the steady pressure going.
“Breathe, boy,” I murmured to him, and I felt him push against me, finally accepting my cock. The head popped in, and I was able to breathe a little easier.
I took my time filling my boy, and I thought again how much I wanted him for more than a single play session. I didn’t know if he’d want me, but I hoped. I wanted to know what it would feel like to have nothing but our skin touching, nothing between my cock and his ass. What it would be like to be able to leave my cum behind in him, claim him from the inside out.
Eventually I bottomed out, my balls resting against him. “You feel so fucking good, boy,” I told him, and his muscles squeezed me in response. “You like that, boy? Like having your Master’s cock filling you up?”
He whimpered and gave an aborted nod since I was still holding his hair.
I pulled almost all the way out and thrust back in hard, earning a louder groan from him. “Gonna pound this ass, boy. Fuck you until you can’t see.”
Then I followed through on that promise. I eased out and thrust in again, repeating it a few more times, thrilling when his ass gripped my cock as I did. But I couldn’t maintain that pace; my cock was too hard and I was too far gone. I started moving steadily, thrusting faster, lost to everything but the beautiful boy under me. The only thing I saw was the red face, hazy eyes, tears-stained cheeks, and gorgeous mouth stretched around the ball gag.
His sounds turned to almost pathetic whines, and I pulled the gag free from his mouth. “What do you want, boy?”
“Need to come, Master,” he moaned.
“Mmm, not yet, boy.” I shifted as I thrust until I got a near shout from him and knew I’d found his prostate. I reached around and under him, though it was a bit awkward around the bench. I wrapped my hand around his cock and stroked it a few times until he whined deep in his throat. “You ready, boy?” I asked, near the end of my control. My balls were drawing up, the tingle heralding my orgasm already starting at the base of my spine.
“Yes, Master,” he groaned. “Please, Master, please let me come.”
He was so gone, my beautiful boy, and the look on his face was enough. I scrabbled to hold on to the last vestiges of my control so I could enjoy his orgasm. “Then come, boy.”
He shouted, much louder than he probably should have, but I couldn’t care. His body shook in the bindings, his ass clenched down on my cock, and his dick jumped as he filled the condom. He was
gorgeous
in orgasm.
I held on as long as I could, determined to savor as much of him as possible, but when he flexed his muscles one more time, it was over. I gritted my teeth hard and crashed over the edge. The orgasm hit me like nothing I’d felt in years, maybe ever. The climax was so hard, my vision faded briefly. My balls ached as I emptied white heat into my boy, the pleasure exploding out and snaking up my spine.
When it was over, I slumped forward, unable to move for the moment. I kissed his back a few times as I struggled to chase oxygen. He was still moaning, and it was enough to get me moving. I needed to take care of him.
I eased out and quickly disposed of both condoms before unbuckling his feet. Cam surprised me by taking care of Kyle’s arms, but I was grateful and he was free. I eased him off the bench and into my arms, then made my way around to the sofa. I cradled him, settling him on my lap as I sat. I removed the cock and ball rings and tossed them aside. Cam brought my blanket and a bottle of water over before kneeling next to Sammy again.
I focused on Kyle, covering him with the blanket and holding him close. My heart melted a little more when he burrowed into my arms. “You did so well, boy,” I murmured, kissing his forehead and running my hands lightly over his arm. “You’ve pleased me so much. So beautiful.”
I don’t know how long we stayed there as I soothed him. I didn’t care. This might have been one of the most amazing scenes of my life, and I was determined to file away every tiny bit of it. I kissed him again, hoping against hope I’d have many more.
Kyle
I CAME
back to myself slowly, with sounds filtering in before anything else. I heard Master’s voice first, whispering what I thought was “beautiful” and “pleased.” I wasn’t sure that could be right, but I was still floating enough to simply accept it.
The touches registered next: a hand sliding up and down my arm, lips on my forehead, cheeks, and nose, my sore ass on hard thighs, a blanket over me. The ring and cuff were gone from my cock and balls. My asshole felt wonderfully stretched and well-used, and my balls were sore from the hits earlier. Master’s hands and lips were on me, and I finally opened my eyes to add vision to my senses.
Master was smiling that amazing smile down at me. “Welcome back, sweet boy.”
My own smile spread. “Thank you, Master,” I whispered, then reached up and touched my neck, relieved to feel the collar still there. I was being silly, I knew that, but I wasn’t nearly ready to let go of it yet.