He finally arrived, a little early actually, after we’d been emailing for most of the day. He responded to a Craigs List ad I posted. He was new to the whole kinky thing. He’d only done some light bondage and spanking, but I was very happy to help him explore some more.
I’d already figured everything out and had a good idea of what we were going to do, so when he arrived, I led him to my bedroom and ordered him to take his shirt off. He definitely looked a little worried and unsure of what was going to happen.
Once he had his shirt off I started to gently play with his nipples to get him into a sexual mindset and it was working. His moans of pleasure were a sign of that. Gradually getting harder exploring his threshold at the beginning. Seeing how much I’ll be able to torture him later on. Luckily he was able to take quite a bit. Could be the fact I ignored his yelps and heavy moaning. It hurt him, but yet he still liked it.
It was time for him to get his ass naked so I could see what type of body my new boy had. I ordered him to take everything off, and like a good boy he did. He was wearing some hot black leather lace-up boots. I made him take them off though.
Once he had everything off, I did one of my signature moves. Took him and literally shoved him flying onto the bed. I good push will always do it to an unsuspecting boy. Then climbed up on top of him, gave him a slap across the face to bring him back to reality, then started working is nipples. You could tell he loved staring up at me as I sat on top of him.
After torturing his nipples and noticing that he was rock hard from all this, it was time for me to get naked. I had been wearing some gym shorts, a cut up gym shirt, and a jockstrap. It was then his time to get the first taste of my hard, thick, uncut cock.
I told him to get down and start sucking it. Once he’d got a little taste of it, I grabbed the back of his head and forced my cock down the back of his throat hearing him gag a little bit on it. I let him get a good taste of it, but then it was time to see what his ass could take.
I had him bend over the bed and took my hand to it. Each swing of my hand left a red mark, a loud cracking noise and yelp from the boy. It was about 15-20 smacks before he really started to squirm, but his rock hard cock indicated that he was still enjoying it. Once he started squirming though, I put my knee on his back forcing him down onto the bed, then kept spanking him.
When I was done spanking him, his ass was a nice red color, but that didn’t mean that i was done working his ass. I strapped on some ankle and wrist restraints (they are actually neoprene ankle straps for a cable machine) because I knew he wanted some bondage, then I took my homemade spreader bar, and clipped his ankles and wrists to the same bar. This left his ass exposed and ready for me to paddle.
There was something I had to do first, force some poppers on him. I took a small rag, held part of it to the poppers bottle, gave it a quick tip, then folded the rag up so the popper part was in the middle. I then took that and held it over his mouth and nose, and forced the poppers on him. I checked earlier to make sure he was cool with them, not everyone is.
With him on his back, legs in the air and hands restrained, I had to take a quick minute or two to skull fuck him. Force my cock deep down the back of his throat. Then took some nipple clamps put them on his nipples and tugged on them a couple times to make sure they were secure. It was then time to take a paddle to his ass.
From what we had talked he’d never had a paddle to his ass, so I started with a couple more warm-up spanks. I grabbed the softest of the 3 paddles I have, took a medium-light swing and impacted on his ass. Slowly ramping up the paddling, deepening the redness of his ass. Also, upgrading to my harder paddles, then finally tried some caning with a bamboo stick I found at Home Depot.
After his ass was a nice deep red with some good hard marks on it, it was time to do the same to his back. I had a hunch being that liked being spanked, he might like other impact play like flogging. Being he was a newbie, I grabbed my softest flogger and slowly started on his back. I left him unrestrained which became a problem when he started to thrash around a little later. I let him get used to the feeling of the flogger, and pumped up the speed and strength of each impact.
I let him have the soft flogger for about 5-10 min, but his back wasn’t showing any marks or turning more than a very light red. It was time to pull out my only other flogger, a hard-edged rubber flogger I bought recently. After 5 minutes with the heavy flogger, it did leave some good marks and I think he enjoyed it rather well.
His ass needed some more work though, but in a different way. It was time to spread his ass open and start pounding it. I bent him over my bed and put just the head of my wrapped cock up his ass. Then slowly started shoving the rest in his ass. Once my balls were against his hole, it was time to start pounding his ass – slowly at first, then nice and hard so he could feel my cock.
I switched off from slow to hard to “is there a jack-hammer in my ass”, watching him eagerly take it and keep begging for more. We tried a couple different positions, but they all ended up with my cock deep in his ass and pre-cum on my sheets from him. Half way through I pulled on and decided his ass wasn’t red enough, so it was time to take the paddle back to it.
After 10 more swings of the paddle, his as was there again. You could tell from his screams that it felt different this time than before. Then it was time to fuck his brains out some more. As some of you tops know, it’s hard work fucking, so it was time to let him do the work. I laid on the bed and let him ride my cock, he did for a bit but he was more eager to slurp it down.
He was a good cocksucker too. Deep-throating my cock and sucking it nice and hard. He kept going till I shot my 6-day load down his throat. Well, I’m sure part of it went down his throat, but my load was so huge that half of it ended up back on me.
I was spent, and he didn’t seem very interested in getting off himself. I had noticed earlier that he loved to touch me, so I asked if he wanted to give me a massage. Luckily he did, and for the next 90 min he rubbed and touched me from head to toe. It was fantastic and very relaxing after a very fun and hot session.