Real Tales - Fisting Fun

This is a something that happened to me recently. It starts off with a little backstory and then goes into the recent happenings. The story is very real, I did change the names. Enjoy!

I had an interesting situation happen recently.  A few years ago, I hooked up with a guy (GG) on Grindr. Him and I are in the same boat, prefer anonymous sex, both bottoms and both interested in fisting. I at the time only hosted at my gloryhole, and he offered to come over and fuck me with my toys and try to fist me. He just asked that he come back another time and I fist him. I agreed, he came over one day, fucked me silly with my toys, and then he fucked me with his big dick and shot his load in me. It was fantastic!  But our work schedules didn't work out and then Covid hit. We never did his return trip where I got to fist his hole. 

One thing that happened with the Covid quarantine, I used my fuck machine almost daily, fucking myself with my dildos. I had to get bigger dildos a few times. That ended when I broke the fuck machine from so much use.  And I went back to work. (Always has to be the villain in every story!)

A few months ago, I was chatting with GG. I reminded him that we needed to get him over so I could work on his hole. I have a new job, but the same schedule. I told him about a day I had coming up where I was off during the afternoon. He said that day would work for him, so I made plans to fist him. I had been talking to my fuck buddy (FB) and mentioned about GG coming over and me fisting him. FB has asked a few times if he could come over and watch guys using my hole. It hadn't happened yet, but I always wanted to keep FB happy, I enjoy how he works my hole, and I don't want to lose him. 

On the day GG came over, he got undressed and got into the sling. Keeping everything anonymous, after he was in the sling, I went to the visitor's side of my gloryhole setup, all I could see was GG's ass and crotch. I rimmed his hole, played with his cock, sucked his cock while I lubed up his hole. And then began fucking him with my toys. I did work my fingers into his hole, but when I tried to get my fist inside, it was too tight. My extra-large hands were too much for his hole. I had seen that FB had messaged me a few times, so I got the bright idea. I asked GG if I could have my fuck buddy over to help fist him. I told him I didn't think my hands were going to get inside his hole, but FB's hands were a little bit smaller and would work.  He agreed as long as it remained anonymous.

I asked FB to come over, which he did.  We took turns fucking GG's hole with the dildos and FB did his magic and worked his fist inside GG's hole. After we finished up, I asked GG how it was. He loved it and wanted to come back again.  I told him that we needed to do that!

A month later, I wanted to get fisted again. I messaged GG and told him I was thinking of taking an afternoon off for some fun. I asked if there was a particular day that would be better for him. He said he would let me know. I was excited to get fisted, I told FB about it.  Later I thought maybe I should have asked if he wanted to join, but I didn't think GG would be interested in that. I know that GG would want it to remain anonymous. I did ask GG later, he would rather it was anonymous, meaning nobody besides him was there. But then he surprised me, he asked if I would object if he brought his friend along with him. Of course, I wouldn't mind.  I told him, "The more the merrier!"

The day before the meeting, I was online and got a message from a hot guy I had seen online many times. I think I had even tried to talk to him once before, I told him he had a nice dick, but he never responded. His profile had pictures of his dick, it looked long and thick. It looked like lots of fun. This time he sent me a message, telling me I had nice pics and profile.  We both agreed that after reading our profiles we would have a great time. We exchanged some pics, his pics were fucking hot!  We talked about what we liked, what we wanted to do and what we wanted done. It sounded too good to be true. It was like I ordered the perfect man to have sex with, it was this guy online. But the longer we chatted, the more it became obvious, he was GG's friend. I started hinting around that we needed to hookup sometime, and he agreed. I then mentioned that I had a guy coming over the next day and he was supposed to bring a friend.  He didn't say anything. We chatted some more and then I asked him, "Are you the friend coming tomorrow?"  And he acknowledged it was him. FUCK!!! This was going to be hot!

The next day, I left work a little bit early. I went home and started getting ready. I sent GG a message, saying everything was on schedule for me. I messaged GG's friend (GGF) and told him I couldn't wait. I finished getting ready and took a shower. I was so nervous, I always freak out a little bit, did I clean out enough? Everything ready to go?  What do I need to do?  stupid stuff like that.  I got a message from GG, he was running late, but GGF would arrive before him.  OK, this will be fun!  I messaged GGF and told him I was ready. I sent him the directions to my place. He said he was on his way. And now was the time I really began to freak out. What did I forget? Where are the poppers? Is it too cold or is it too hot? Did I unlock the door? Does the garbage or the pets stink? Should I light a candle? Do I need music?  Oh wait, GG had mentioned having some porn playing in the background. Did I clean out enough?  What if.....oh fuck it, it is go time!

Sure enough, GGF messaged me, he was outside. I told him to come on in, the door is unlocked. I took a deep breath, and then a hit of poppers, it was game time!  The room was flooded with light as he opened the door and walked in. He walked in and got undressed. The first thing I was his tongue on my hole. He gave me a very good rim job. I had never had it done like that, it was incredible. But after he got my hole all wet and loose, he stood up and started to fuck me. DAMN, his dick was huge!  I felt my hole get stretched out as the big head on his cock pushed through. He pounded my hole, roughly making it his own. He didn't hold back, he went at it like he was going to breed my hole right there, as roughly as he could. But when he got close, he pulled his cock out and he went back to rimming my hole again. I don't remember how long we continued this pattern of rimming my hole and then pounding my hole, but at some point, I saw the room light up as GG came through the door. GGF got back down and rimmed my hole. But then I could tell that GG was having fun playing with GGF's hole and cock. GGF started fisting my hole, working his big hands inside my hole. It was incredible. I was able to take his big hands, but the sensation was too much, and I would have to tap out a few times. He would pull his fist out and he would go back to sucking my cock and rimming my hole. We continued this for a while. After about an hour, it was almost time for GGF to leave. He stood up and started fucking me again. My hole was so stretched out and puffy, it felt awesome. But when he was close, he didn't pull out this time. When he started to shoot in my hole, my stretched-out hole was feeling every squirt of his cock shooting his cum. I had never felt a cock shooting cum like that. I was very impressed!

As soon as GGF pulled out, GG cleaned off his cock.  As GGF got ready to leave, GG took over my hole. He first rimmed it good, cleaning up that cum. He then worked some toys into my hole and later his fist. He was going at my hole, working it over hard and fast. He was hitting my prostate each time, making me start to have an anal orgasm. I was loving it!  He worked my hole for another 30 to 40 minutes. I was at the point of exhaustion. My hole had been worked over for almost 1 hour and 45 minutes. I finally asked GG if he was getting close. He apologized, said he wasn't that good of a top, but I reminded him that he had been working my hole over and it was incredible. I could hear him jerking his cock, when he got close, he pushed it inside my well-worked hole and pumped a few times and then shot his load. 

As he got cleaned up and ready to go, I thanked him, and we both agreed we needed to do it again. After he left, I got out of the sling, and I couldn't stand up. My legs were all shaky. And I had a popper headache. I locked the door and laid down for a minute. I was so wore out, but at the same time, I wanted more. I wanted to get my hole worked over some more. I fell asleep dreaming of what had just happened. I slept for about 6 hours, so exhausted and so freaking happy!