February 27, 2024

I fucked Football Player boy raw for the first time !





It feels like forever since football player boy has visited. But during the last time he visited, at the end of our visit during debriefing, I asked him a question. I made it more of a statement, but it was a question.

I told him, "I really want to fuck you raw one of these days." He thought for a moment and said, "I'm not saying yes, but I'm definitely not saying no."

Today when he texted, he said that he wanted to have try to have two orgasms during our visit. Then he continued and said, "I was hoping that you and that machine could be used during that."

He normally would just request the fuck machine, or the sling, or cock torture... But this time he specifically said, "YOU and that machine."

I really wasn't sure which "that machine" he was talking about but I didn't care. I concentrated on the "you."

I took this as a green light!

10 years ago when we first met on Craigslist M4M, he was just looking for someone to peg him with a dildo. He always wanted blindfolded. At the beginning, if I even cleared my throat with a masculine cough he would lose his hardon.

Eventually he began sucking cock. Then he learned to swallow my cum. Then he let me fuck him with a condom. Today is the next milestone.

When he arrived he came through the garage, gave his normal cheery salutations and immediately began to strip exposing his hard on. I swear he must arrive hard in the driveway.

I was sitting in my chair naked except for a white jockstrap. I was planning on keeping the jock strap on the entire time because I had plans with the dirty jockstrap a few days later. I was going to use it as a mask over ball beating boys face when he came for his next visit.

I spread my legs a bit, which gave him the invitation to get on his knees and start sucking my cock. Which of course he immediately did. Today was a good day, my cock was throbbing hard. As I always do, I look down at his broad shoulders and big chest which is quite a turn on for me as he sucking my cock.

Occasionally he would look up at me. Sometimes I feel that he has puppy dog eyes. Sad and Wanting eyes. Fuck it's hot. But I don't know if he's looking up at me for confirmation he's doing a good job, or if he is checking to see if I'm taking pictures.

He sucked my cock for quite a while then I said let's head downstairs to the sling.



He hopped right up in the sling and his legs immediately went in the air for me to put his ankles in the stirrups connected to the chain hanging from the ceiling holding the sling in the air.

During previous conversations he told me that he didn't want me to listen to him if he wanted to stop after the first orgasm. He wanted me to force a second orgasm out of him. He made it clear that he did not want to have the opportunity to stop or prevent the second orgasm no matter how sensative his cock was getting. He made it clear he wanted me to keep going and get that second orgasm, "No Matter What!" So this time I put his wrists in tight restraints and attached them to the chains coming down near his shoulders to the sling.

I slipped a glove on my hand and greased up a few fingers with lube. I glanced up and watched as his his eyes looked into the mirror above the sling. He was watching intently as I added more lube and more fingers. Quickly I had three fingers of my right hand up his ass. He likes the smoothness of the glove, and it does seem to make my fingers slide in his ass much easier.

With my left hand I applied a bit of lube to his cock and started playing with it. Instantly I felt his ass clamp down on the three fingers from my right hand. His cock was hard and he was already oozing pre-cum.

I found his prostate, twisted my fingers horizontally and pushed against his prostate milking it. Another squirt of pre-cum came out. His prostate was hard, but not quite rock hard. I didn't want it to be rock hard yet, because that would have told me an orgasm was impending. And I definitely did not want him to cum yet. Not for a long time.

Normally I use an over-the-counter lube, but I knew it was going to be a long session and I wanted his ass to be comfortable. I had mixed up a fresh batch of j-lube. I reached down and squirted the j-lube on his ass and my glove. I worked the j-lube into his hole. I heard him let out a small sigh followed by a moan as his eyes focused on the mirror above us.

With the four fingers I started pushing deeper into his ass. I wasn't playing with this cock right now because I did not want his ass to clench down, not yet. With my four fingers in his ass I started to rotate and spin them around while adding more j-lube.

I played with his ass like this for a while. Then reached up and started playing with his cock. His ass clenched around my four fingers and I felt his prostate start to get harder. No, no, you're not going to orgasm yet, I thought to myself. So I stopped playing with his cock.





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A straight friend of mine, Jesse, had given me a remote control vibrating egg. It wasn't just an egg, it had a long tail on it. And at the end of the tale was a cock ring and a ball ring. The egg is rather large. I've tried to shove it into other asses of my other boys and no one's been able to quite take it yet. But since I had loosened football player boys ass with four fingers, I thought this would be the perfect time to use it.

I grabbed the toy from the table and lubed it up, and started pushing it in my football player boys ass. There was a little resistance. I kept pushing. He had no idea that it was also a vibrating toy, not yet. It made it into his ass and I reached up and played with this cock. As expected, his ass clamped down around it and sucked the toy deeper into his body.

I reached over and grabbed the remote control from the table and clicked the button. I heard the vibration humming against the cloth of the sling. It seemed almost to amplify the sound. I tugged on it a bit, not planning to pull it completely out of his ass, but just put pressure from the inside of his ass. Then I stroked his cock again which caused his muscles to pull the toy deep inside him again.

While it continued to vibrate I grabbed a soft rope and tied it around his cock and balls. I looped it around and around again and again. Then started looping the soft rope only around his cock to trap the blood in his cock as I was stroking it. I looped the rope around his balls a few more times and then tied it off with a slip knot.





I played with the vibrating toy again first by clicking the button causing it to increase in speed. And then tugging on it to start to pull it out of his ass only to play with his cock and let him suck it back up inside.

I reached above us and grabbed a bungee cord hanging from the ceiling. I tied a loop on the end of the rope going around his cock and balls and attached it to the bungee cord pulling his balls roughly into the air.

I started playing with a vibrating toy again. Teasing and antagonizing his ass. If the rope hadn't been around his cock and balls I would have attached the other end of the vibrating toy to his cock and balls but it was too late now. The rope connected to the bungee pulling his balls into the air would have to be enough for now.

With the toy still up his ass, I lubed up my thumb and shoved it in his hole. My thumb found his prostate and I pushed against his prostate as I could feel the toy vibrating behind my thumb.

A squirt of precum came out of the head of his cock so I used it as lube to stroke his cock as I continued changing the speed and intensity of the vibrating toy.

I wanted to see if I could get my entire fist in his ass today. So I pulled the vibrating toy out and dropped it to the floor after turning it off. Four fingers of my right hand easily went in his ass again. I started fucking him with the four fingers, pushing in and out as the sling swung to and fro.

I aligned my four fingers parallel with the crack of his ass, and added my thumb. I was nowhere near getting my knuckles in his ass, but all four fingers and thumb were inside him.

I reached down with my left hand and pulled my cock out of the white jockstrap and started playing with myself. As expected, with the addition of my thumb he started to moan. It was a happy moan but it was also a slightly painful moan, made my cock throb.

I pushed all five digits into his ass but I couldn't quite get past my knuckles. I pulled my thumb back out and started fucking him with four fingers again. His balls still being held high in the air out of my way by the rope and bungee cord. I was fucking him rough with my fingers. Pushing hard. Pushing the sling away from me. He was moaning like crazy. I pushed my thumb back in his ass, giving my wrist a spin, pushing hard into him. My knuckles were almost going in. His cock was rock hard and so was mine.



I knew I could make him orgasm at any moment. His legs were thrashing around. His wrists were stressing against the restraints that were normally not restricting his hand movements. His cock pulsing to each movement of my hand. But I didn't want him to cum yet.

I grabbed the 13-in long toy that starts with a small bump and gets larger as it goes in. The first four or five bulbs went in with absolutely no problem. Then the fifth slid inside him. I started fucking him with the toy. Pop Pop Pop. His ass was talking to me with a popping sound as the toy went in and out.



Soon the 6th and then the 7th ball/bulb/bump went in his ass. The 7th had been the most difficult to push into his ass. There's only one left. Only a few people can take it all the way to the 8th and have all 13 inches of toy in their ass.

I pulled the toy almost completely out of his ass and then shoved it all the way back in stopping at the 8th. It wasn't quite fitting yet. Yet.

I pushed, told him to Bear down, and I crammed the 8th ball in his ass. The entire toy was inside him now. It caused him to let out a moan and instinctively my left hand went back to my cock.



I wanted my jock covered with as much pre-cum as possible, so each time I wasn't playing with my cock I would put it away. With my left hand I could feel my jock was becoming soaked with my precum. After playing with my cock for a minute, I played with his cock. It pushed the toy deep into his ass. I love it when it's all the way in him. I pulled it out and started fucking him with it again. Only returning to the seventh ball as I fucked him rapidly. But occasionally forcing the eighth one in him again

I pulled the entire toy out of him and dropped it to the floor. I replaced it with four fingers and I could tell he was extremely sensitive. I had pushed his ass to the limit and I knew I needed to get him off quickly or we might pass a point where he's no longer enjoying this sensation. I reduced to only three fingers and started playing with his prostate. Massaging and caressing it. Pushing on it. While stroking his cock.

His balls were still attached to the ceiling with a bungee cord and now my three fingers were fucking his ass as my hand stroked his cock.

Occasionally just to tease him I would take my hand off his cock. He would beg me to stroke his cock but I would ignore his cock and play with my own. But after a bit more begging, I would play with his cock again which was covered in his pre-cum.

I decided it was time. I felt his prostate getting hard as a walnut. I knew it was going to be easy. I continued fucking his ass with my fingers and stroking his cock until a flood of cum washed over his stomach. He was twitching and jerking and his legs were convulsing



Knowing I was going to try to get a second orgasm out of him I immediately stopped touching him and pulled my fingers out of his ass to give him just a moment of a breather.

I thought the best way to get him to have a second orgasm might be somewhat hands-free. So I grabbed the butt plug TENS unit and pushed it in his ass. I clicked the power switch and started increasing the intensity. Then I saw his ass begin to pucker rhythmically with the light that flashed on the tens unit.

I kept it mild at first as he was still catching his breath. But I wanted him to experience a second orgasm. That's what he wanted. I didn't know if we were going to get there or not.

I didn't touch his cock, I didn't finger his ass, but I slowly increase the intensity of the TENS unit until he started to moan. I wanted to get him moaning really seriously and try to get another orgasm out of him. I started playing with my own cock again.

After playing with the TENS unit for a few minutes I pulled the butt plug out of his ass and stood up. He was watching as I stood up from the stool that I normally sit on while playing with his ass . I don't know if he knew what was coming next or not. But he had asked for it.



And then... for the first time with football player boy... IT HAPPENED!



I shoved my raw cock deep into his ass. Oh my God, it felt wonderful. It was worth the wait. Fuck it was incredible. I leaned over him, grabbing him by the hips, and was pounding him with my RAW cock.

I know his ass was sore from everything it had been through, and he had a strange look on his face. He was looking up into the mirror as my raw cock was fucking him. I'm not sure if the look was that his ass was hurting or that he had second thoughts about being fucked raw.

I started stroking on his cock as I fucked his ass hard. His cock and balls still attached to the rope attached to the bungee attached to the ceiling. I continued pounding his ass. Fuck it was an incredible feeling. And what an incredible view.



Watching his football player boys physique under me as my bare cock was sliding in and out of his ass was mind blowing. I fucked him for 5 or 10 minutes and his dick was starting to go soft. It had never actually regained full rigidity, but it was now starting to go limp. I yanked my cock out of his ass. While I continued to play with my own cock, I tried to stroke his cock a bit to get him hard again.

His entire body convulsed. His cock was still super sensative from his first orgasm. His cock was not getting hard again. I lubed up my gloved hand and shoved three fingers back in his ass and started playing with this prostate again still attempting to get him hard. His prostate was soft and spongy, and it had no plans on getting hard again.

I stood up and fucked him one more time. I decided NOT to drop a load in him today. It was a big enough step just getting to fuck him raw.

I told him, "I'm trying my best to get you off a second time." He laughed and said, "I know, I know, I was trying, it's just not going to happen. My ass is starting to get really sore."

I asked him if there was anything that I could do to get him off a second time. We both concluded there was nothing that could be done to give him his prized second orgasm. We were done for the day. We both chuckled and laughed.

I put my cock, still covered with his ass juice, back in my jock strap. I remembered that I would be using that jockstrap with ball beating boy in just a few days. Covering his face with it as we played. Making him smell my juices and Football Player Boy's ass juice as well.

He hopped out of the sling, and cleaned up a bit. We debriefed in the hot tub for about a half hour. There were no comments or complaints about being fucked raw. I look forward to his next visit.