February 20, 2024

I've been speaking with Edgingfun23 for a while on FetLife. He came over for his first visit recently. He told me he was interested in getting a deep enema, and I explained that a deep enema takes time and it might not be necessary. So when he first arrived, as I do with all my guys, I met him in the driveway and we came inside.

He was dressed straight from work. Usually guys that come for a visit wear jeans and a t-shirt, very relaxed looking. But edgingfun23 had clearly just come from a day of work. I sat back in my easy chair, looked straight into his eyes and simply said, "well... Strip!"

I could tell that he was a bit nervous, but he started stripping his clothing off and putting them in the chair next to where he was standing. I just watched intently as he took off each article of business clothing. When he was naked, I just stared at him for a minute and he stood there wondering what would come next.

I got up from my chair and went to the couch and grabbed a pair of wrist restraints. His hands were hanging down to his sides, and not recognizing these were wrist restraints, he did not extend his hands. So I grabbed a hand and pulled it out in front of him, putting the velcro restraint on his wrist. And then I put a restraint on the other wrist. Back to the couch I got a dog collar and put around his neck. I stood behind him and reached around playing with his nipples, groping his cock and balls, and tugging a bit on the dog collar.

I told him to come to the bathroom where we were going to clean him out. I briefly explain the difference between a deep enema and a light enema. I told him we would start with a light enema but he would have to tell me when the water he was expelling into the toilet was clear. If it cleared up after a few cycles we would be done, if it didn't we might have to switch to a deeper enema.

Apparently never having an enema before, he wasn't sure what to do. I told him to get down on all fours on the bathroom floor. When he was in the doggie position I smeared some Vaseline on my finger and slid it up and down the crack of his ass. I filled a small enema bulb with warm water, put some Vaseline on the tip of the tube, and using two of my fingers spread his ass cheeks so I could insert the tip of the enema bulb into his ass.

As I squeezed all the water into his ass he didn't make a sound. I told him to stay in that position as I filled the bulb a second time, inserted it and added more water to his bowels. I smacked his ass and told him that I would leave the room to give him some privacy, and that he should take his time and expel the water. When he was done, he was to flush the toilet and as I heard him flush the toilet I would know it was time to come back in for the next round.

I left the bathroom and closed the door behind me. It wasn't too long until I heard the toilet flush. I went back in and he was standing as I filled the enema bulb again. I told him to get back down on all fours. Two more bulbs of warm water filled his bowels before I left him to expel again.

He learned quickly because the next time I came in the bathroom he was already on all fours. I think we went through four cycles of rinsing him out when I asked him how the water was. He said it was pretty clear. I think we went through one more cycle. I forgot to tell him on the last cycle to make sure he gets as much water out as possible.

When we were done in the bathroom I told him we were going to head upstairs. He had previously told me he might need to work on his cock sucking skills so I thought the best place to do that would be upstairs. Although I knew he was extremely interested in the cow milking machine and the fuck bench, I needed my cock sucked first, so we were starting upstairs.

We got upstairs and I briefly showed him all of the toys that I keep in the bedroom. Cock cages, ball weights, paddles and whips, and plenty of anal toys. I passed him a tight fitting cloth hood that has eye holes and a mouth hole. I told him to put it on. At first, as he pulled it over his head, I don't think he realized there were eye holes. I told him to pull it a bit forward that there were eye holes and we wanted to center the mouth hole so my cock had access to his mouth.

After he made the adjustment to the hood I told him to climb on the bed on all fours. I wanted to check out his ass. I wanted to start playing with his hole immediately.

Instinctively his ass rose into the air as his shoulders went down onto the bed. I think he has been in this position before. I grabbed some lube and squirted it on my finger as I rubbed it across his hole. I slipped my finger back and forth over his ass and then pushed a finger inside. Oh my god, it went in easily. I knew his ass was going to get a lot of play today. This was going to be fun.

With my right hand now stuffing two fingers in his ass locating his prostate, my left hand reached between his legs and started to play with his cock and balls. He was already dripping precum like a leaky faucet. I massaged his prostate and could feel his cock throb and leak even more. I could definitely tell I was going to be enjoying this.

His shoulders sunk lower onto the bed raising his ass even higher. He brought his knees slightly together pushing his ass even higher into the air. I easily got three fingers in his ass.

I stepped away and grabbed a soft piece of rope and tied it around his cock and balls. I looped it around and around pulling his balls away from his body and then knotted the two ends of the rope. I made sure to leave about 2 feet of extra rope on one end after I tied the knot. I could use this extra rope to give it a tug whenever I felt like it. My fingers dove back into his hole again.

I could feel my cock getting hard inside my sweatpants. I looked down and saw a wet stain of precum in the front of my sweatpants. I was definitely enjoying my fingers in his ass. I was definitely enjoying his ass up-head down position.

With my right hand I would finger his hole, with my left hand I'd either smack his ass cheeks or pull on the rope that would tug on his cock and balls.

Soon I replaced my fingers with the Christmas tree toy. It's a short middle toy consisting of five balls connected together. If you hold it upright it resembles a Christmas tree, that's the name I've given it. It's a metal chromed toy, and compared to body temperature, it's quite cold. I think that's one of the reasons I like it. The sensation a guy gets as I'm shoving it in his ass for the first time is cold, metallic, almost brutal.



His ass was so loosened up from my fingers that the first two balls of the Christmas tree toy popped in easily. I pulled them back out and pushed them back in again, fucking his ass with the cold Chrome toy. Then I pushed a little harder as the third ball started to penetrate him. Each ball gets larger, so each time I push it's a little bit more difficult.

I fucked him with the first three balls for quite some time. Sometime I would reach down with my free hand and grabbing the rope tied to his balls and giving it a tug just to hear him moan.

My cock was definitely tenting my jogging pants. The wet stain was growing. So with the toy still up his ass, I reached down and pushed my sweatpants to the floor and step out of them. As I stepped out of my sweatpants, I continued fucking his ass with the toy. Now my cock was standing stiff, now free from the confinement of the sweatpants. I pushed the toy until the fourth ball disappeared in his hole. He let out a very soft moan and wiggled his ass.

Eventually all five balls made it into his ass. The entire Christmas tree toy was inside him. The only thing that remained was the base of the toy keeping it from slipping entirely in his body. I reached between his legs with my right hand and stroked his cock. That made his ass clench and pull the toy tighter in his hole. As a stroked his cock with my right hand, I stroked my own cock with my left hand.



I really wanted to shove my cock in his ass right then. I just wanted to fuck him with every ounce of my strength. I wanted him to feel my cock penetrate his hole. But we hadn't talked about fucking, and we'd only been playing about 15 minutes. I definitely didn't want things to end this quickly. And if I had started fucking him at this point, I would have been a 10-pump-chump and the visit would be over… LOL

Plus I wanted to see how good of a cocksucker he was. He said he might need some training. And not everyone will go from ass to mouth. If I fucked him, he might not want to suck my cock. So I just continued playing with my cock as I simultaneously stroked his cock. I was watching the toy pulse each time the muscles in his ass clenched as I stroked his cock.

I didn't want him to orgasm too soon, so I stopped playing with his cock and started fucking him with the toy. And I started fucking him rapidly with the toy. With his ass in the air in his head on the bed he looked so natural. It looked like he was created for that exact position. Fuck it was hot to see.

I told him to spin 90° on the bed. Until now, he had been sideways on the bed. I knew what I was planning. I'm sure he didn't. I wanted him lengthwise on the bed because after I was done playing with his ass for a while, I knew that I was going to swing around in front of him, laying on the bed and present my cock in front of his mouth.

He shifted with his ass to the bottom of the bed and I continued to play with the metal toy in his hole. Eventually I pushed it all the way up in to the base again. I threw the rope up over his back, and climbed around in front of him, laying on my back in bed with my cock in front of his mouth.

He did not need an invitation to start sucking on my cock. I reached down and grabbed the rope and gave it a tug to let him know I still had control over his balls even in this position. I relaxed the rope and put my hand on the back of his hooded head just feeling his head move up and down as his mouth swallowed my cock.

It felt fantastic. He was pretty good at cocksucking. I was giving him verbal feedback that he was doing a good job. "That's a good boy, suck Daddy's cock. You're doing really great. Fuck that feels good. Damn your mouth feels great."

I let him go at his own pace for about 10 minutes, and then I grabbed the back of his head and forced him deep onto my cock until he was gagging. I gave him verbal feedback again, "That's it, choke on Daddy's cock. That's what Daddy likes. Choke on Daddy's fucking cock boy."

Since he was wearing a mask I snapped a few photos knowing I was going to share them here in the story. I reach back and grab the rope and gave it a tug again. I knew not only was it yanking on his cock and balls, but the rope was coming right up the crack of his ass and probably moving the toy that was inside him.

It felt so good I just laid completely back and enjoyed the next 10 minutes. I knew his jaw was probably getting tired but I didn't care. It felt wonderful.

Eventually when it seems like his jaw was getting really tired, I climbed out from under him and walked in behind him again. Fucked him with the Chrome toy that was in his ass for a moment and then pulled it out completely and showed him what had been up his ass for the previous 30 minutes.

I've got a large rubber toy that is similar. It's probably about 8 inches Long and starts with a small ball and then increases in size as it goes. Again this one is a series of balls attached to one dildo. There's no separation. It is not ben wah balls.



I pushed the first three balls in his ass quickly. This was the same diameter of the largest of the metal toy that had been in his ass. I added some lube and started pushing a bit further spreading his hole open. He was moaning and at the same time backing his ass up onto the toy.

Just as I had done with the metal toy, I started fucking him with this red rubber toy. Each time pushing it a little deeper and deeper until eventually the entire length of the toy was in his ass. I reach between his legs and untied his cock and balls. His balls were looking a bit blue. I stroke his cock and it was soaking wet with pre-cum. He had been leaking onto the towel that was between his legs. There was quite a puddle there.

I fucked him with this toy for a while before I pulled the rubber toy out and lubed my fingers. I quickly got four fingers in his ass again. I twisted and rotated my hand around, twisting my fingers in his ass. For a moment, I thought I was going to get to fist him, but his body was telling me four fingers were enough for today. Next time I am going to put him in the sling. Next time we're going to try my fist. Next time I think it's going to work.

With my right hand I continued fucking his hole, with my left hand I was playing with my own cock considering fucking him again. Damn, I wish we had had that conversation about fucking him with my cock, but we didn't.

There's one larger toy that everyone seems to have a problem with. But his ass seemed so accommodating I thought I'd give it a try. I don't know what it is about the toy, but not many people can take it. He took it. He took it easily. It took a few moments, and some coaxing, but eventually it was fully in his ass. This just made my cock even harder.

I told him to lay flat in bed. His hands were outstretched toward the corners of the bed. I hadn't used the wrist restraints yet, so I went to the top of the bed and it clipped the ropes onto each of his wrist restraints. As I pulled the ropes tight, they made that wonderful ratcheting sound. He didn't even flinch.

I grabbed a vibrating toy. I lubed up the vibrating toy, then lubed my fingers and shoved them in his ass making certain he was well lubricated. This is a hard plastic toy that vibrates. It has dimples on it similar to a golf ball but instead of dimples in, they're dimples out. A bunch of little bumps. Lots and lots of little bumps.

I started working it in his ass and although he was laying flat on the bed he was able to push his ass up into the air to greet it. That's when I turned the knob and the vibration started. He let out quite a sound. I fucked his ass with this toy for a while, shoving and spinning it as I teased his hole.

I had a vibrating egg with a tail on it but I had left it downstairs. I ran downstairs to get it, damn it, I couldn't find the remote. I guess that will have to wait for the next session. My thought was that I wanted something up his ass that would STAY up his ass while he sucks my cock again. The vibrating egg with a tail would have been perfect.

I continued working on his ass with the vibrating toy. He just laid flat on the bed, his body looked completely relaxed except for his ass that was arched in the air to accept the toys as I presented them to his ass.

I pulled the vibrator out of his ass and I worked four fingers in his ass again. I was trying to get my thumb in again. I just wasn't going to happen. But that was just fine, I was having a great time.

I wanted him to suck me off, but I still wanted something in his ass as he took my load in his mouth. Something on the larger side, but something that wouldn't slip up inside him. So I grabbed a butt plug puppy tail and pushed the large butt plug into his ass. It has a rather large ball that holds it in place, but it went in rather easily.

I told him what it was. I told him he was a puppy now. I snapped a few photos and then unhooked his hands from the ropes and told him to get up on all fours and wag his tail for Daddy. " wag your tail boy, wag your tail for daddy." His cock swung between his legs as he swagged his tail.



I slid in front of him again pushing his mouth down onto my cock. This time I grabbed him by the dog collar around his neck and tightened it until I could hear him gasp and fight for air. At that moment I grabbed the back of his head and pulled it hard down onto my cock until he was choking for air. Between the tight dog collar and my cock in his throat he was struggling. It was making my cock so hard.

I knew he wanted to put on the milking machine on the fuck bench downstairs, but everything just felt so good at this moment, I just knew I needed to get off. Who knows maybe I can get off again downstairs, but right now I just wanted to get off. I wanted to feel my cum flood his mouth.

I laid back as he sucked my cock again. He didn't need any coaching at this point. He was doing a great job taking my cock down his throat.



We hadn't discussed if he was a swallower or not so I grabbed a towel just in case he was a spitter. I could tell his throat and mouth were sore, but I didn't care. I wrapped my legs around his back and used my leg muscles to pulling onto my cock. I laid back and enjoyed every moment of him sucking my cock.

I felt my balls began to bubble and churn, I knew it wasn't going to be long. I started yelling at him, "Suck Daddy's cum out, boy. Take Daddy's cum. Fuck boy here it comes. Here comes Daddy's load. Take it boy, Take Daddy's cum."

With that, I let out a loud guttural growl as I felt ribbons of cum shooting into his mouth. Not knowing if he was going to swallow, spit, or possibly puke all over me… I had a towel ready. But the next thing that I knew, his mouth was off my cock and he was catching his breath by breathing through his mouth. His empty mouth. Yep, he's a swallower.

Then he took my cock in his mouth again. He started sucking and licking. I realized he was trying to get every single drop out. He grabbed my cock by the base and squeezed it like a tube of toothpaste, trying to get those last drops into his mouth. He was playing with my balls trying to get them to release just a bit more.

Then he started stroking my cock. He was rubbing the sensitive head of my cock with the palm of his hand. Squeezing it and licking it. It felt great.

Then I said, let's head downstairs and see how much cum we can milk out of you.

We got downstairs and I gave him a quick tour of the dungeon. I showed him the saint Andrew's cross for flogging, and the sling for fucking, and the fuck bench.

He laid across the padded top of the fuck bench as I reached below him and grab the extra wide velcro strips which went around his back just above his hips and up near his shoulder blades.



I put a generous portion of lube on his already hardening cock and connected up the milking machine. I've still been experimenting with the milking machine, but it seems to work when I connect it using very short bungee cords to the base of the fuck bench and then the suction pulls it up onto my boy's cock. And that's exactly what happened.

I flipped the switch and the pulsing began. Suck suck suck as it pulled itself up onto his cock. Once it was firmly attached to and sucking his cock I lubed up my finger and pushed two fingers into his ass and began massaging his prostate. I was milking his prostate for all it was worth.

I was watching the glass jar figuring he would orgasm sometime soon. I was waiting to see his cum squirting down the tube into the jar. He was moaning in rhythm with the pulsating sound of the milking machine. It took a couple of photos and short videos as a finger fucked him and the milking machine continued sucking on his cock.



I grabbed a long skinny dildo and lubed it up and pushed it deep into his ass. I started fucking him with a dildo as his moans became more and more intense. I started fucking him like a rabbit with the dildo. It has ribs on it but it was going so fast I'm not even sure his ass could feel the ribs of the toy.

I reached between his legs and started to play with his balls and the upper portion of his cock that was not sucked into the milking sleeve. With one hand I was fucking his ass with the toy, with the other hand I was stroking the top of his cock and manipulating his balls. I didn't think he could last much longer. And it had only been about 10 minutes.

Then I heard him let out a moan. A long soulful moan. Even though I thought that I had a grip on the toy that was in his ass, his ass clenched and shot the toy right out of his ass past my hand and the toy fell on the floor with a thud. I saw his entire body spasm as he grunted a few times. I continued working on his prostate, massaging it to get every last drop out as he had previously done to my cock upstairs. He was now done.

I turned off the milking machine, fingered his ass just once or twice for good luck, gave a wicked laugh, and we both relaxed for a moment.

I unhooked the velcro strips holding him to the fuck bench and we checked the size of his load in the glass jar. For whatever reason, he had a dry orgasm. But he still had fun. And I certainly did too.

Next time, the sling.
Next time, I'm hoping to get my fist of his ass. Next time, we're going to talk about if I can fuck him.



Here are all the toys that we up his ass during this session !