Ryder moaned loudly as I slipped the device on under the table. He went to move, but the chains kept him in place.
"Be still, Ryder," I said, smacking him loudly on the ass. "No moving unless I tell you to."
"Yes, master." He hissed as I rubbed my handprint on his butt. I reached for the small, heart-shaped paddle I had also bought. Moving to his left side so I could see his face, I gently slapped him on the ass with it. Ryder gasped and looked up at me before remembering himself and gazing back at the floor.
"I don't like you looking away from my, baby. I want to see your reactions to what I'm doing to you."
"Whatever my master wants," he said, turning his head to look at me again. "And as hard as my master wants to give it to me I will accept it."
I smiled, knowing that was his way of telling me to spank him harder without breaking the submissive game he was playing. Lifting the paddle, I smacked each cheek of his ass before stopping to rub it.
"I think I want my baby to count off his punishment."
"Yes, master." He panted, mouth parted as his eyes glazed over with lust. I spanked each cheek ten times, and Ryder moaned each number out, letting me hear exactly how much he liked it.
"What does my baby want next?" I asked, rubbing his ass, loving the red marks I'd made on him.
"If my master wants to, his sub would love his hole spanked."
"Oh that would please me alright." I moaned, putting the paddle down. I picked up the small crop and spread Ryder's legs even farther. With the flick of my wrist, the leather strip at the end of the long wand whacked against his tight hole. He whimpered as his hole turned even pinker and started to quiver. "Oh, my baby likes that. Don't you, sweetheart?"
"Yes, master. More please, give me more," he begged, and I obliged him. Ryder was gorgeous, absolutely perfect right then. His face was flushed while he moaned and squirmed, responding to everything I did to him.
Next, I grabbed the lube, squirted some on my fingers and rubbed them over his now very sensitive hole. Ryder cried out, causing me to glance at his face. I relaxed and went back to what I was doing when I realized it was a cry of pleasure and not pain. Knowing that Ryder loved the bite, I pushed two fingers in hard to start with.
"Are you ready for the next part of your punishment, Ryder?"
"Yes, master, punish your bad little sub." He moaned, trying to move his hips back on my fingers. I smacked his ass twice as hard as I had before.
"Be still or I'll stop and leave you tied up with no release for the rest of the plane ride."
"Spence, would you really do that to me?" Ryder asked, his eyes going wide, almost looking afraid.
"No, baby, I wouldn't. You're way too hot for me to not touch," I said, rubbing his back with my other hand to try and calm his fears. "We can stop at anytime, babe."
"No, I want to keep playing. What you're doing to me is so awesome, but so new, my body feels like it's on overload." He giggled. "I just wasn't sure if that was part of the game about you leaving me here desperate and needing you."
"Nah, I couldn't ever leave you wanting." I snickered as I pulled my fingers out of him. Before he could even say anything, I pushed in the vibrating butt plug I had grabbed.
"Oh fuck that's nice, master," Ryder cried out, his hands tightening into fists. I moved around to the front of him and knelt down in front of his face.
"It has twenty settings, baby," I purred, licking his lips. "And I'm going to play with the remote while I fuck your sweet mouth."
He smiled widely as I stood and lined up my cock with his mouth. Ryder opened up for me and I slid it over his tongue. At the same time, I hit the remote onto the first setting. He gasped, and I took full advantage of it. Ryder took half of my nine inches down his throat like a wonderfully practiced cock sucker.
"Oh god, baby. That's good, so fucking good." I moaned, pushing more of my dick into him. "Take my cock like a good little sub."
Ryder moaned loudly when I turned up the vibrating plug a few more levels. He started going to town on me then, and I knew if he kept this up I wasn't going to make it to get a part of his ass. When I went to move, he started sucking harder. I chuckled at how my little submissive wasn't being very submissive at all. But I lost all train of thought when he started using that talented tongue as I thrust into his mouth.
Moments later I was crying out Ryder's name as my cock exploded in his mouth. I turned up the plug as well, loving how he was trying to prolong my orgasm. When I was finally spent, my spent cock slipped past his lips. Ryder moaned loudly, licking up the small amount of my cum that dribbled out of his mouth. It was hot, and even though I was completely wiped, it got my blood pumping again.
"I can't come, it won't let me come," Ryder whimpered, pulling against his restraints. "Please, master, I need to come!"
"Okay, baby." Seeing how desperate he was. I moved back around him to undo his cock restraint. The second it was off, his dick got even harder and his balls drew up. I knelt down quickly and slid the mushroom head of his cock into my mouth. That was all it took to set Ryder off. He screamed loudly as he shot stream after stream of cum down my throat. I swallowed all of it, loving how hard I got him to orgasm.
"Fuck, Spence, that was amazing." He panted as he came back down from his climax. I licked his softening dick before moving and standing back up behind him.
"I'm not done with my hot little sub yet." I chuckled as I smacked his ass hard. He moaned and squirmed as I also turned up the plug to the tenth setting. I felt the blood returning to my lower half as my cock started to take notice of my hot man's ass. Picking up the paddle, I decided to be daring and spank him with the vibrating plug in.
"Master, I'm going to come again if you keep doing that." Ryder groaned loudly.
"No you're not! Not until I shove my cock into your pretty ass, baby." I growled, smacking him again and again. "You will wait for me, sub."
"Okay." He squealed as I spanked him with the paddle harder. "Please fuck me, master! I need to feel you inside me. I'll do anything, master. I swear I'll do whatever you want if you just fuck me."
"Hmmm, I need to think about that, baby," I replied, smiling widely. I knew it was mean to get what I wanted when he was so out of his mind with lust, but I did it anyways. "Will you go to the tailor with me and let me buy you some suits? You're going to need one for the board meeting."
"Yes! Yes, I'll do it, just fuck me!" Ryder begged, moaning as I kept paddling his ass.
"Will you play this game again with all of us being your masters?"
"Oh god, yes. That sounds so fucking hot." He moaned, trying to rub his growing erection on the table.
"Would you play my little submissive sometimes without the chains and whips, baby?"
"I don't know what that means, but yes, Spencer. Yes to anything you want!"
"It means I really liked how you are doing exactly what I say, Ryder. I want to play that game more often with you," I replied, turning up the vibration level. "I want you to walk into my office sometimes and tell me that you're there to service your master."
He moaned loudly, nodding his head rapidly as I turned up the toy more. I put down the paddle and moved to unstrap his wrist and ankles. As soon as he was free, I rolled him over. Instantly he pulled his legs up and planted his feet on the table.
"Oh my god, we have to use this toy more often for foreplay." Ryder moaned as he reached for his now-hard cock. I smacked his hand away and inserted myself in between his legs. My hard dick was pressing against the plug, shooting vibrations up it. We both groaned loudly, and I decided I was done playing, I needed in Ryder.
I shut off the plug, pulled it out, and replaced it with my cock. Ryder's already stretched hole easily accepted me in one hard thrust. I moved his ankles onto my shoulders so I could get in him nice and deep. Leaning over so our noses just about touched, I slowly pulled back out.
"I love that I can ask you to try new things with our sex life," Ryder whispered, smiling up at me.
"I love that you trust me enough to tell me what you want, baby." I replied, pushing back into him slowly. "I'm always willing to see if there's something else we like. Plus, most of your ideas I end up loving as well."
"Good. Now shut up and fuck your little sub with everything you have." He winked at me. I laughed for a moment, before doing as he asked. Ryder's mouth parted as he panted under my hard and fast thrusts. I fucked him with everything I had, completely surprised we hadn't broken the table yet.
"I fucking love this game." I grunted out each word on every thrust forward. Ryder nodded frantically, grabbing onto my forearms so he didn't slide across the table. I mashed my lips down onto his as I pounded into his perfect ass. He opened for me immediately, running his tongue around the inside of my mouth. As I got closer to coming, I changed the angle so I could hit his sweet spot.
"Fuck!" Ryder screamed as he climaxed, filling up the space between us with his release. Simply smelling his seed sent me over the edge, and the tight hold his ass had on my cock sent my world spiraling. I roared above him, thrusting into him as hard as I could. When my orgasm ebbed, I collapsed down on my man. Ryder's legs slid off my shoulders as he wrapped his arms around me.
"Like planes now, baby?" I asked after I finally had the energy to lift myself off of him.
"Oh yeah, and I like the club we joined too." He giggled, lying back on the table like a wet noodle. I laughed as well, loving that we could tease each other this way. It was the perfect distraction during all the chaos we had going on around us.
* * * *
After we landed, we caught a cab to the hotel where I had reserved a room. By that time it was way past both our bedtimes and we crashed. Ryder barely got all his clothes off before we climbed into bed. It might have been the first time in my life that I didn't brush my teeth before going to sleep.
"Hello, morning breath." Ryder giggled the next morning, waking me up.
"Sorry, I'm a mouth breather sometimes," I said, turning my head away from him.
"Spence, I'm just teasing. I love you, all of you, even your stinky breath."
"Thanks, baby," I replied, rolling my eyes as I got out of bed. Glancing at the clock I saw we'd gotten up before the alarm on my phone was set to go off. We'd have just enough time to grab coffee and swing by my favorite tailor before the board meeting. I had called ahead and given my guy Ryder's measurements, so hopefully nothing would need any adjustments.
I brushed my teeth, showered and was dried off as Ryder took his shower next. Just as he was wrapping up, I was knotting my grey silk tie. I'd chosen what people call a power suit, black pinstripe with a black shirt.
"Fuck, Spence. Why don't you wear that more often?" Ryder asked as he walked out of the bathroom with a towel around his waist.
"I work part-time from home in South Dakota." I chuckled, giving him a wink. "You want me to dress up to work in the home office?"
"If I get to see you looking like that, hell yeah," he answered, rubbing his groin. I held up a hand to stop him as he moved to drop his towel.
"We can play afterwards, baby. Right now, we have to behave and get going."
"I swear, you're no fun." He grumbled as he went over to his bag.
"Really? I wasn't fun on the plane ride?"
"Okay fine, you're fun a lot. I'm just nervous," he answered as he got dressed.
"I know, Ryder. I am too. Let's just get through this and be done with this mess," I said, walking over to him. He leaned back against my chest as I wrapped my arms around him and kissed the top of his head. I let him go a few moments later, and we finished getting ready.
Five minutes later we were downstairs, climbing into a cab. I gave the driver the address of the tailor, and we rode in silence. Ryder took my hand and gave it a squeeze, which earned a smile from me. I paid the driver when he pulled to the curb, and we got out.
"Spencer, my old friend," Manny called out as we walked into his shop. I glanced around, smiling when I saw that the place hadn't changed a bit. It was as clean and organized as ever. "How are you, my dear boy?"
"I'm good, Manny," I answered, walking into the man's arms for a hug. Manny had always had a special place in my heart and was the closest thing I had to a father figure growing up. He looked like the stereotypical New York Italian grandfather you saw in the movies, down to his white hair and short stature. "Manny, I'd like you to meet my partner Ryder. Ryder, this is my dear friend Manny."
"Please to meet you, sir," Ryder said as he extended his hand. Manny pushed it aside and pulled Ryder into a hug.
"You can forget that sir crap, young man." Manny chuckled as they pulled apart. "Spencer is like family to me."
"Manny was my father's tailor before he died," I explained to Ryder who was glancing between the two of us. "One of my first memories was coming with my dad to get a suit from Manny. I've never gotten a suit from anyone else, I only trust him."
"Always a good boy," Manny chuckled and pinched my cheek. He got away with that kind of stuff since he was older. I knew Manny's wife had wanted him to retire years ago, but he insisted that if he was able, he'd work. Plus, for Manny, it wasn't just a job, but a hobby as well. "Now, let's see if I've not lost my touch with the suits I picked out for your young man."
"Hell would freeze over before you picked out or made anything that wasn't perfect, Manny." I chuckled as we followed him to the back of his store. Sure enough, the navy blue suit was a perfect fit for Ryder. I could tell he seemed a little uncomfortable in it, but it looked fantastic on him.
It took us about a half an hour to check out that suit and the backup one Manny had made. He got upset when I tried to buy them both, but I assured him that Ryder didn't have any suits and might need another one. And given his line of work was a service-oriented industry, his credit card slips had room for a tip. I made sure to give him a large one and not hand over the slip until we were walking out the door.