March 13th 2023 - football player tells me this was his most powerful orgasm ever


I'm going to tell you the ending of the story before I even start the story. In fact the title has already told you the ending. Football player tells me this was the most powerful and extreme orgasm he's ever had in his life.


So here is what happened.

He came over and as usual showed himself through the garage and came into the house through the garage door. He said, "hello, how have things been" and was being cordial as he stripped naked without me needing to say a word. As usual he already had a hard on.

In case you're a new reader, he's not an actual football player, but he has the build of a football player. Big broad shoulders. Beefy thighs. Strong muscular arms. He's got a nice beard and mustache that is always nicely trimmed. The hair on his head is cut short and always looks great. And he shaves all his pubes. He's wonderfully smooth everywhere.

Sometimes he drops to his knees, if I tell him to, and sucks my cock. But I'll be honest with my readers, my doctor started me on a new medicine and things aren't working downstairs right now until my body gets used to the new medicine. But that doesn't stop me from having fun, and clearly didn't stop him from having the best orgasm in his life.

So we headed straight downstairs and he jumped up into the sling. He's been in the sling enough times he didn't have to ask any questions. He just hopped up and threw his legs in the air so I could attach them to the loops around his ankles. Sometimes I put a blindfold on him, but not today. I wanted him to watch in the mirror above us. And I noticed instantly his eyes were staring into the mirror.

He likes the smooth feeling of a rubber glove on my hand as I assault his hole, and I was watching his eyes look into the mirror as I put the gloves on my hands and put lube on my fingers. His hands were holding onto the chains near his head that hold the upper side of the sling in the air. He was gripping The chains rather tight today, this just made his biceps bulge even more. Mmmmmmmmm.

As soon as I was gloved and lubricated I instantly started with a finger up his ass. It slid in with absolutely no difficulty. With that one finger I pushed in deep and rotated back and forth then pushed a little deeper and found his prostate and started to play with it. He was still watching in the mirror as he let a moan slip out of his lips.

Soon I had two fingers in his ass. Spinning them around. Twisting and shoving. I applied some more lube. I had mixed up some powdered J-lube. I mentioned to him that we were using a new type of lube today. He corrected me and said, "I remember that stuff, it's very slippery." My bad, I don't remember using it with him before but we must have.

I quickly worked in four fingers coating my hand and his ass with J-lube. I twisted back and forth. I wanted to get my fist in him today if possible. I was on a mission. I kept working my fingers into his ass, twisting around stretching him more and more. His cock was so fucking hard it was incredible. I think I was a little jealous because of my new medication, lol.

I reached up and stroke this cock a few times. At this point, I'm trying to keep my left hand clean, and use my right hand on his ass. Just in case I want to suck his dick to tease him. In the meantime, I continued my assault on his ass with my right hand. I worked my thumb in and started to push but there was no way he was opening up to accept my entire fist... at least not yet.

With four fingers and a thumb in his tight hole, I reached up and stroked his cock with my left hand again. I felt his ass clamped down on me like a shop vice holding on to a piece of wood before you saw it in half. I think I had an evil laugh as I continued playing with this cock as his ass was grabbing and crushing my fingers. I looked up and his grasp on the chains was even more intense.

I continued playing with his cock for a while, purposely getting his ass to clamp down on my fingers, and then let go of his cock and let him take a breath without making a move with either of my hands. As I felt his ass loosen up, I tried to give it a little push. I got a little farther but still my fist didn't go in. I assaulted his prostate for a while, and then put lube on my left hand.

I started shoving my left hand up his ass. Four fingers and a thumb went in easily but I still couldn't get past my thumb knuckle. I've been told my left hand is slightly smaller so I was hopeful. But it wasn't happening yet.

With my left hand I started piston fucking his ass. I was really going hard and rough. Then I pulled my hand out and replaced it with three fingers from my left hand and three fingers from my right hand. He now had six fingers in him and my hands were back to back.

Using the muscles in my wrists and my fingers I pryed my six fingers apart. Three fingers went to the right and three fingers went to the left causing his ass gape open. I could see straight up inside his body. I could see that bright pink flesh of the inside of his ass. It was so fucking hot. I thought if I could keep applying some pressure and loosen him up, I might be able to get my entire fist in his ass.

I pulled the three fingers of my right hand out and tried all five fingers of my left hand, again giving them a hard push and a twist hoping I could get past my thumb knuckle. It still wasn't happening. I was coming to realize that it might not happen today. But I was having fun trying.

I twisted my left hand around for a while attacking his prostate again with at least three fingers. His cock was twitching, oozing cum, I glanced up his and his eyes were still transfixed in the mirror watching my hand assault his hole. I reached up with my right hand now and started stroking his cock while pushing on his prostate with my left fingers.

I decided that if I wasn't going to get my fist up his ass, I was going to edge him for a long long time. I kept stroking his cock while fisting his ass. Well I guess I cannot technically say I was fisting his ass but all four fingers and my thumb of my left hand was in his ass. I still couldn't get past that thumb knuckle.

I started fucking him again pushing my hand hard, sometimes going fast and sometimes going slow. I really wanted to get my fucking fist up his ass. I pushed hard, really hard. He grunted, then a moan, not a good moan, a painful moan. I told him hang in there, I've almost got my fist up your ass. I pushed harder, he grimaced again, my fist was just not going in his ass, even as much as both of us wanted it to.

I played with his cock some more and then switched hands now using my right hand, all four fingers and thumb but still that thumb knuckle was stopping us. I applied more lube and tried again. Not yet, but I'm going to keep trying.

I got a long double-sided dildo off the table. I pulled all my fingers out and replaced it with the toy. I held the double ended dildo like a cop would hold a night stick. I started pounding his ass. The way I was holding it reminded me of how Norman Bates was holding the knife in Psycho. Screech screech screech screech! Lol

I reached up and started playing with his cock and edging him again while fucking him with a double ended dildo until the toy almost completely slipped up into his ass. Being double-ended it didn't have a base and I did not want to lose it up there. I edged him until I noticed his right arm was starting to quiver. That's one of his "tells." That tells me he's getting close to an orgasm. So I let go of his cock. I held the dildo completely still for a moment, even though it was almost fully up his ass. His arm stopped quivering, it was time to resume play.

With the double ended dildo up his ass I grabbed a second dildo. This is more of a standard dildo. It's pink and has balls, and it's rather large. Larger in diameter than the double ended. I tried to push it up his ass alongside the double ended dildo. The double ended dildo was still far up his ass and I was giving the pink dildo a hard push to try to get it in. I was actually afraid I was going to tear skin. He was being brave, we were pushing his limits, but he wasn't saying the safe word or telling me to stop. I noticed again his eyes were burning a hole in the mirror as he watched everything that was happening.

I tossed the pink dildo to the floor. That's where all the dirty toys go after they've been up his ass. I grabbed a slightly smaller beige dildo and tried shoving it alongside of the double-ended. I lubed again and again as I pushed, but it too wouldn't quite make it. I didn't want to cause physical harm but as he threw his head back and his legs lifted high into the air it was his body's way of telling me to stop. So I stopped for a moment.

I dropped the double ended dildo on the floor, and picked up the pink one. Now I've got the pink and the beige. Surprisingly they both slipped in at the same time. He threw his head back again, his legs went higher into the air as he tried to separate his ass cheeks even more than they were. We were definitely, positively, pushing him to his extreme limits.

I started to fuck his ass with both dildos at the same time. Sometimes both in and out at the same time, sometimes alternating, but never pulling them completely out. I noticed he started moving his legs rhythmically along with my fucking. I wasn't sure if he was trying to open his cheeks wider or if he was trying to impale himself in the toys even more. Then I noticed his right leg start to quiver. I don't know if I've ever seen that happen before with him. It was definitely an automatic function of his body, it was actually fun to watch.

After a few minutes I dropped both of the toys to the floor, and replaced them with my right hand. All my fingers and my thumb went into his ass. The thumb knuckle was right there at the edge. Just a little push and it would go. I reached up with my other hand and stroked his cock causing him to clamp down on my hand. I stroked him for a while with the plans of letting go of his cock and taking that microsecond where his ass was loosening up and plunge my fist all the way in. I had such high hopes, but it didn't work. But we were both having such a fucking blast.

He gets into cock torture, so I reached over and grabbed a rubber band off the table. I threw the rubber band over his hard cock like someone doing a ring toss onto a coke bottle at the carnival. WINNER! WINNER!

I pulled the rubber band back and snapped it against his hard cock. It bit into the soft flesh. He let out a Yelp, followed with, "Ohhhhh God, Yessssssss." He loves the rubber bands.

A reposition the rubber band to another location of his cock and snapped it again, moved it and snapped it again, moved it and repeated, moved it and repeated. I was already seeing the dark purple welts come up on his cock.

He had missed a couple of appointments/visits. He'll message me when he's got some free time, but because of his job sometimes he has to cancel at the last minute. He had canceled a few times and he knew the punishment. And it was time. And the punishment wasn't the rubber band snapping against his cock, he likes that. The punishment is something that he doesn't necessarily love.

I mumbled, "You've missed quite a few appointments. It's time to be punished."

I want you to picture him in the sling. His hands grabbed onto the two chains at his shoulders. His ankles in leather stirrups hanging from the chains near his ass. His knees above his ass line, higher than his belly button, opening his hole nice and wide for me. His ass cheeks slid off the edge of the sling hanging in mid-air. He's got wonderful ass cheeks. Full and round and hairless.

I watched his eyes follow in the mirror as I reach to the table and got a wooden spoon. One of the long wooden spoons that you would keep in the kitchen, however this one doesn't go to the kitchen anymore.

With my left hand stroking his cock, I pulled back and smacked his right cheek with a wooden spoon. Hard. I smacked his ass really really hard with the wooden spoon. He let out an agonizing, "owwwwwwwe."

His teeth clenched, his arms convulsed, his hands grip the chains, as he tried to straighten his legs pushing his ass away from me, swinging the sling away from me using his leg muscles.

I laughed out loud. I smacked the other cheek hard. I would wait for his leg muscles to relax and smack him again and again with the wooden spoon. I think it was a total of six snacks on each cheek. Six very hard snacks.

I dropped the wooden spoon to the floor and smacked him a few times with my hand. All the time stroking his cock. I noticed there were huge white welts coming up on his ass in the shape of the wooden spoon.

I plunged my fingers back up into his ass while still stroking his cock. His right leg was quivering uncontrollably now. He was so fucking close to an orgasm. I was going to let him release soon, but not yet. I picked up the spoon and smacked each ass cheek a few more times, dropping the spoon to the floor again. Still stroking his cock. Still watching his right leg quiver uncontrollably. Then his right arm started quivering along with it.

I barked at him, "Don't you dare think about having an orgasm yet."

I pulled my fingers out of his ass and while still stroking his cock grabbed the rubber band and pulled it far out and let it snap against his cock flesh. He was moaning in ways that I had never heard him moan before.

I got my fingers up his ass and started viciously assaulting his prostate while continuing to stroke his cock.

He had recently told me about a fantasy that he wanted fulfilled. Until earlier today I didn't know how it was going to fulfill it, but then it came to me. I knew exactly what I was going to do next because he was very close to dropping his load.

I reached back and grabbed a small flesh colored dildo. It's probably only 5 inches long and not very round in diameter. I could see him watching in the mirror, but he had no idea what I was doing. I'm sure he was thinking, "Why is my Sir grabbing such a small toy after already having two large toys in his ass?"But he didn't say a word.

I grabbed the small dildo and put it on the edge of the table where I could grab it quickly when needed. I continued stroking his cock and fingering his prostate. Using two or three fingers I was pushing hard and massaging on his prostate. His cock was oozing constantly.

My left hand was still playing with his cock, my right hand up his ass. I knew I would feel his ass clench down on my hand even more right before his orgasm. His right leg started twitching even more. It was completely uncontrollable. Both of his arms were also now quivering. I put more lube on my right hand and started fisting him as much as I could. That thumb still wouldn't go in but at this point I thought if it did we'd never get it out.

I return to playing with his cock and assaulting his ass pushing on his prostate preparing him to have an orgasm. He was holding off his hard as he could. He was struggling but he was trying his best not to orgasm.

Finally I gave him permission to cum. I told him to let out his load. I told him it was time to have that orgasm that we have been working on so hard together.

I grabbed the double ended dildo, held it like Norman Bates and started piston fucking his ass again. I was stabbing his ass with the double ended dildo going as deep as I could. I was fucking him fast with it. He started letting out little barks as it bottomed out inside of him. Still stroking his cock the entire time.

I noticed his ass clenched down on the toy, I felt his cock get even harder and stiffer and I think it even grew a little longer. I jumped up quickly, leaving the double ended dildo in his ass. I grabbed the small 5 inch dildo off the table. I continued to stroke his cock and I shoved the 5-inch dildo between his cock and his stomach as he orgasmed. Squirt after squirt after squirt coated if I have in dildo as he continued to orgasm. I rotated the small dildo around catching every drop of his cum all over the dildo. Then I yelled, "Open your mouth. Clean it off."

This was his latest fantasy, he wanted to eat his own cum after having an orgasm. I shoved the toy in his throat until he gagged a bit and then told him make sure he sucked all the cum off of it. I fucked his mouth with the toy as he created a vacuum around it. He readily sucked on the toy getting every drop off until it was perfectly clean.

I went back to playing with his ass and still playing with his cock. He wanted a second orgasm today, but I know him better than that. It wasn't going to happen, so I just started to terrorize him by continuing to play with his cock while fingering his ass.

His leg stretched out straight trying to pull away from me and I let out the most sadistic laugh. "I thought you wanted a second orgasm today?" Then I laughed again. He said, "no no I don't think so." I laughed again and said, "I knew that."

His leg was still quivering. He let go of the chains and started wiping the sweat off his face. I remember him going, "Whooooohhh damnnnnnn that was fucking incredible, I've never had an orgasm like that before in my life. That was fantastic."

I threw him a towel, but there wasn't anything to clean up. Every drop have his orgasm had landed on the toy and was now in his stomach. He had licked the toy completely clean. He jumped out of the sling. It was such a powerful orgasm, I think I had to stedy him a bit. He cleaned all the J-lube off his ass, took a brief stop in the bathroom, and we spent the next 30 minutes debriefing, and catching up in the hot tub as we relaxed.

It was fucking awesome.