May 31, 2025 - Football player takes a load then wants to have two orgasms!



Sorry I have not written a story in quite some time, but this winter has been rough on me. I think I went through a dark place for a while but I'm feeling much better now that the weather is warming.

Thursday was my birthday and Friday I got a message from football player saying he wanted to come over. For quite some time we've been trying to get him to orgasm twice during one visit. Well, we tried again today.

When he first arrived, I was already in my birthday suit, completely naked relaxing in my easy chair with a hard-on. He came through the door and immediately began to strip his clothes off as always. He looked over at me in the chair and mumbled, "I've really needed this for a while." He started sucking on my cock. It was fantastic. As usual, as I looked down at his broad shoulders, the shoulders of a football player, it only made my cock get harder. He would alternate taking his time on my cock, deep throating it, and sometimes devouring it like a starving person at his first meal in weeks.

I don't like to orgasm this quickly, I like to go to the basement, play for a while and finally drop a load in his ass. But after about 10 minutes of such a wonderful blowjob, even with his mouth full, I heard him say... "I've needed to swallow your load for the longest time."

That was enough to put me over the edge. I tried to hold back a bit longer, but thinking how much he wanted my creamy, salty, sweet cum in his mouth was too much for me. I figured, why not? Maybe today is the day I will have two orgasms. I put my hands on his wide shoulders and felt myself getting closer and closer to the edge.

As he deep-throated me once, and I felt my cock getting lodged in the back of his throat, it was too exciting. I started making the grunting noises so that he knew I was about to fill his mouth. He pulled off my cock almost completely leaving just ahead in his mouth. He wanted to taste everything. And I did not disappoint. I let him have a huge load. I felt ribbon after ribbon of cum squirt into his mouth. He swallowed, and kept sucking. He was definitely attempting to drain me completely dry. My cock was still hard so I just let him keep sucking for a while until he had every last drop out. Then I said, let's head downstairs and take care of you now.

We went downstairs and he hopped into the sling. I put his ankles in the stirrups. There was no need to tell him to scoot down in the sling so I could access his hole more easily, he's done this enough times that he was perfectly positioned. His cock was still hard, and his ass puckered for me. I put a pair of rubber gloves on and started to lube up his hole.

First one finger went in, quickly followed by a second. He was very tight today. It had been quite a long time since we last played. I knew this was going to be a long, long session and I did not want to stretch him too quickly. Today patience was going to be the key to our fun. I played with two fingers for quite some time adding more and more lube each time. I got both fingers deep in his ass and started playing with his prostate. He lit up like a Christmas tree. And so did his cock. I put a little lube on my spare hand and started stroking his cock.

I realized I did not need to put lube on my spare hand, he was already pre-coming so much I could have been stroking him with nothing but his own precum. He was hard as a rock. He tilted his head back in the sling and started moaning, "Oh yes, oh yes, I've needed this for a while."

As I stroked his cock I felt his ass clench around my fingers. I know when that happens he's really having a good time. So I stopped stroking his cock for a moment to let his ass loosen up a bit. I was able to get a third finger in and rotate them around. Plenty of lube now made it easier to spin my three fingers around in his ass. I continued to occasionally stroke his cock just to feel his ass clench onto my fingers. Once I had him loosened up and his ass was relaxed I decided to choose a toy for his hole.

I wasn't sure which toy I wanted to use today. I kept glancing over at my plethora of toys on the table, trying to decide exactly what I wanted to do to him today. He had previously mentioned he loved the TENS unit that would send electrical pulses into his ass. I had just recently got a new TENS unit butt plug and decided this was the time to try it out. It's definitely larger than my other toys that work with the TENS unit but not a whole lot bigger than my three fingers. Although it is a bit longer than my fingers, I thought he would be ready.

The toy slid into his ass easily but then the toy started to bottom out in his ass. I couldn't push the whole thing in. I noticed him watching in the mirror hanging above the sling and he realized I was having trouble getting the entire toy in his ass. He beared down and pushed, opening his hole, relaxing his muscles at the same time. The toy slipped in to the base. I plugged it into the TENS unit and clicked the switch. Oh no, good grief, no blinking light. I told him the battery was dead, just relax for a minute, don't push it out, I'm going to grab another battery. I just left him there in the basement, legs up, toy in his ass.

I pulled my rubber gloves off and went upstairs and grabbed another battery. I returned to the basement and put the battery in the TENS unit. In less than a minute, I had the TENS unit turned up to six (out of ten) already. I could see his hole puckering and squeezing with each blink of the light. He started a soft moan, almost like a purr of a cat. I reached up and started stroking his cock again, knowing it would cause his ass to tighten on the toy which would probably increase the sensation of the electrical shock.

And that's exactly what happened. It caused him to start moaning louder, longer, and nearly continuously. I increased the dial until I heard the moans change to a slightly painful loan. Of course this made my cock get hard again. I turned the dial on the TENS unit back down. Actually I turned it down quite a bit. Because I had a lot more in store for him today. I didn't want him to orgasm yet.

I hadn't played with his ass since I had returned with the battery and still had the gloves off. For the most part my hands were clean since the electro toy filled his ass and I had not fingered him since my return, so my hands were clean and prepared for sounding. I don't like to switch straight to sounding if my fingers have been in a guys ass. There is a small risk of urethral infection if my hands are "dirty." I grabbed a single use, sterile lubrication packet and tore it open. Squeezing the lube on the length of the metal sound getting it ready for his cock hole. This is a thin metal sound but it has an egg-shaped ball on the end. I rubbed the sound back and forth on the slit of his cock getting it lubed up. Then I started to push the sound into the hole in his cock. Another moan slipped from his lips. With metal sounds, I let gravity do the work. If the sound stops there's a reason. Never push a metal sound. If it stops, there's a reason.

And that's what happened today. It got about halfway down the length of his hard cock and the sound stopped its decent into his cock. I gave it a tiny bit of pressure, not much, and it did not want to continue. I could feel the egg shaped ball on the end of the sound now about 3/4 of the way down his cock. It usually goes all the way. This concerned me a little bit but not enough to stop our playtime.

I pulled the sound out and let gravity feed it back into his cock a few more times. And each case the sound stopped at the same location. So I pulled it out, lubed up a thin rubber sound and got ready to push it into his cock. Even though he was watching in the mirror above us, he lifted his head so he could watch me push the rubber sound into him. Being a rubber flexible sound, this one can be pushed. So I mentally marked where the metal sound had been stopping as I began pushing the rubber sound into his cock. When it got to the location the metal sound had been stopping, there was a little hesitation so I asked if everything was okay. I think he responded with, "oh god it's wonderful." I checked again and said, no pain? He said "keep going."

I gave the sound a little push and it went past the area that had given us problems. I kept pushing knowing the next resistance would be his prostate. I felt the resistance and slowed down a bit, looking up, watching his face for a reaction. His mouth popped open and he sighed followed by a long deep moan. I pushed a bit further and could feel the sound passing through his sensitive prostate. He continued to moan over and over. I pulled the sound out a bit and pushed it through his prostate again.

Eventually the entire length of the rubber sound was in his hard throbbing cock. He was definitely oozing a lot of pre-cum around the edges of the sound and I was using his precum to stroke his cock. The tens unit butt plug was still in his ass. It was turned to a level of four, but now with the sound completely inside him, I turned the TENS unit back up to a seven or an eight. I thought he was going to cum right away. That would have been okay, but I continued playing with the sound and the butt plug pushing him closer and closer to the edge.

I put gloves back on and lube them up because I knew he was so close to an orgasm. All I needed to do was massage his prostate and we would be done. At least for the first of two possible orgasms today. We've tried so many times but I've never gotten two orgasms out of him in one session…. Not yet, and this was a big goal for him.

I turned the TENS unit off and popped the toy out of his ass dropping it to the towel on the floor. I replaced the toy with two fingers and quickly found his prostate. I started pushing on his prostate with two fingers of my right hand, milking his prostate, massaging it. I could feel the rubber sound that was passing inside his prostate. With my left, clean hand, I reached up and started pulling the sound out and pushing it back in. The rubber sound is rippled so I could feel the ripples going past the two fingers of my right hand that was pushing hard on his prostate. I stroked his cock a few times and felt him clinch onto my fingers in his ass as I continued to play.

As I was spinning my fingers in his ass I adding a third finger, his cock started to constrict and push the rubber sound out. It's incredible the muscle control a person's body has. It fun to watch a guy's cock push the lubricated sound out of his piss slit as I excite him. I know this sensation of the sound being pushed out of his slit added to the intense feelings of my fingers in his ass playing with his prostate. I felt his prostate getting harder and harder. His cock pushed the last of the rubber sound out of his body. As the sound dropped onto his stomach, I knew we were close. It wasn't going to take much. So I started stroking his cock while pushing on his prostate. His cock was leaking so much cum, I thought he might have ALREADY had a mini orgasm or possibly a ruined orgasm, but then his entire body convulsed and his cock erupted with cum. His cum went everywhere. He let out a yelp and a groan followed by a sigh.

Thinking back, I should have scooped his cum up and fed it to him, or pushed his cum into his ass but I didn't. At the time, I realized that I could have continued to terrorize his cock while it was so sensitive but I knew I had plans to get a second orgasm out of him. So I pulled my fingers out of his ass slowly, and told him, "Relax for a few minutes, I'm going upstairs, get your senses back, catch your breath, we're going to try for a second orgasm today." And with that, I pulled off the glove, walked out of the basement and went upstairs, washed my hands and checked my email and Facebook as he relaxed for a while.

I knew one of two things were going to happen. He would be thinking of his dream cum true of having a second orgasm, or like many men, he would be ready for a nap. I hadn't even cleaned him up. I left him covered in his own cum. And spent the next 5 or 10 minutes upstairs before returning to the basement.



PART TWO - - - - - -

As I return to the basement, I didn't say a word. I just re-gloved my hands, applied some lube, and shoved two fingers back in his hole. As expected he was tired, spent, and I could tell his hole was a bit sore. And, of course, he was also very sensitive because of his recent orgasm. So I decided to go very slowly to get the second load out of him.

I begin working on his ass with just one or two fingers. I decided not stroke his cock but I would occasionally grab onto it and clamp it at the bottom with my fingers. I rubbed my thumb over the underside of his shaft. I knew he was still super sensitive. He wasn't quite hard, but I can also say, he wasn't soft either. As I played gently in his hole I started pushing on his prostate again and just like pumping up a bicycle tire, his cock started getting hard again. I grabbed one of his favorite toys which is a very long dildo, probably 12 in long, starting with a small ball and balls increasing in size.

The balls are not connected by string, it's more like a long floppy toy. The first ball popped in his ass with absolutely no problem. Then I pushed and the second one disappeared as well. Soon the third ball was pushing against his hole. His hole didn't quite want to accept the third ball, but I knew in time he would loosen up again. So I pulled the first two out only to push them back into him seconds later.

I kept working the first two balls in and out of his hole until I felt him starting to relax. It probably also helped that I stopped antagonizing his cock. Soon the third ball slipped into his sore and tight asshole. I did the same thing with these three balls, in and out, in and out, over and over. Eventually the fourth ball was inside of him. It took a bit more effort but eventually the fourth ball was inside of him. This time I played with his played with his cock, just because I knew his ass would clinch around the fourth ball that had just been pushed into him.

He started moaning again, precum started leaking out of his cock although not much since he had already given me one load. I pulled two or three of the four balls that were in his ass out, only to slowly put them back in again. I started tugging on his nuts a bit, they felt like they were full and preparing to give me another load. I continued working the rubber balls of the toy in and out. By his body language, and the fact that he was almost scooting down in the sling, I knew he wanted that fifth ball shoved into his hole. I lubed it up quite a bit and gave it a push. It didn't want to go in. I stopped playing with his cock which let his ass relax a bit. And I pushed again. I didn't think it was going to go. He was watching in the mirror above us and he saw and probably felt the difficulty I was having. He beared down on the fifth ball and soon his ass swallowed it too.

I left all five balls in his ass for a moment or two to let his body get acclimated to it. Occasionally squeezing his cock with my hand, or pinching the underside of his cock head to distract him. I felt he was starting to loosen up a bit and I popped the fifth ball out and then pushed it right back in place. I thought this was going to be it. Five balls out of eight is pretty good. But I could tell he wanted more. So with quite a bit of effort I eventually pushed the sixth ball into him. It was not easy, but his cock was rock hard telling me he was enjoying it. He started moaning again. Mumbling, "Oh god this is good. Oh yes."

I eventually got the seventh ball into his ass. This meant almost 90% of the long toy was inside him. I knew he needed the sensation of movement in and out of his hole if I was going to get him off for the second time today. So after the seventh ball had been in his ass for only a minute or two, I popped it back out. I really could tell that that 7th ball was a bit much considering he already had one orgasm.

I started slipping the balls out of his ass one at a time, only to push them back in. Number 6 went in and out, in and out, then 5 did the same Then six went back in. Ball number 5 and 6 kept going in and out. Then four-five-six would go in and out. Of course, as there were less and less balls inside of him, it was becoming easier and easier for his ass to acclimate quickly to the changes. It was giving him a sensation without causing him to bear down on it. I started stroking his cock again. Soon I was pulling almost the entire length of the toy out only to shove it back in over and over. At the same time I was stroking his cock quickly and repeatedly. I added some lube to my hand as I stroke his cock which added to the precum that was already leaking out.

This went on for a while and I really didn't think I could get another load out of him. I thought I might be able to get a dry orgasm out of him but I didn't think we were going to get more cum squirting out the end of his cock. But I hadn't given up, I at least wanted to make him have a dry orgasm before we finished. It was as close to two orgasms in one day as we were going to get. I knew it was his goal to get to orgasms, but it wasn't going to happen today.

Then I started to encourage him. "Come on boy, give Daddy that second load. I'm not going to stop until I see another squirt of come at the end of your cock. You can do it. Give Daddy another load. You know you want to make me happy. You can do it."

The verbal encouragement along with my hand stroking his cock and the toy thumping in and out of his hole was enough to do it. He started to arch his body in the sling. His ankles straining against the stirrups holding his legs high in the air as I assaulted his ass with the toy. I continued stroking his cock sometimes flipping my hand over so it would feel completely different and new. His body started to thrash around in the sling as if we were experiencing an earth quake. He was so close and he was trying so hard. I watched as he looked up in the mirror as the toy was rapidly going in and out, thump thump thump as the size of the toy changed as the balls went in and out of his hole.

He let out a gasp, as entire body went rigid. I thought for certain it was going to be a dry orgasm but the next thing I realized was he was squirting another load of cum all over his stomach. We had achieved the prized second orgasm. I immediately popped the entire toy out of his ass. I knew he was going to be sensitive, but a continued playing with his cock for another minute just to antagonize him.

I told him, "Good job boy, you've always wanted two orgasms in one session, and we finally did it. Good Job boy".