It’s no secret that Tripp is a fisting bottom. Over the years, I have become a very good fisting Top. I’ve fisted guys long before I met Tripp. We met because fisting was on the menu, and I’ve subsequently had a great deal of time and practice to develop my technique.
There’s a group of men who meet for fisting parties semi-regularly that we attend. Most guys who attend are bottoms and Tops are fairly rare and much sought after. Given my prowess, I was always kept very busy. I was up to my elbows in asses. I always been a bit jealous of the pleasure the bottoms were having and very much admired those who could stretch easily. Some of these men could take two fists, and they always were howling with ecstasy while doing it. Now, I like a good cock in my ass, but it was tight, particularly back then. I could barely imagine one hand in me, let alone two.
Eventually, I decided I wanted more than cock in my ass. I wanted to finally take a fist. I’ve had some large toys in me, but after a certain size, they just seem to not go in. One evening, I was attending the party by myself. I don’t remember why Tripp wasn’t there. I talked to several of the men about what I wanted. Dave was another Top with a great deal of experience. He volunteered to “pop my cherry”. I got into one of the slings and Dave lubed me and his hand up very thickly. Dave has medium hands.
He was extremely patient with me. He would push me a little further each time he entered me. He spent about an hour stretching my hole and talking me through everything he was doing. Finally, he had four fingers in me easily. As he started to push his hand in me, I tensed immediately. He backed off and had me relax and breathe. “You just have to want it”, he said. I wanted it, but I just didn’t think my pelvis was wide enough. It felt like he was hitting bone. He wasn’t, he assured me. “Just breathe” he kept saying as his hand went slowly into my ass. “Breathe”, he said as I started to tense up. I did and relaxed. I could feel his hand sliding ever so slowly deeper into me. “Keep breathing”, he said. “You’re almost there”. I did as he said and kept relaxing my body. He talked to me the entire time. “Breathe in”, he told me. I did. “Now exhale”. As I was breathing out. his fist slipped all the way inside me.
At first, it felt too big. My immediate reaction was to try and push it out. I could barely control the spasms. “Keep breathing and it will pass”, Dave told me. It did pass. I got accustomed to the feeling of a fist inside me. Dave slowly started to pull out and then push back in, loosening my hole over time. Eventually, his hand went in and out easily.
Jerry walked over and was watching the scene. He has larger hands than Dave, which I noticed since he was putting gloves on them. Dave stepped away and Jerry took his place. Jerry repeated the process Dave took me through, though it went far more quickly and his hand was in me before I knew it. Eventually all the guys were standing around the sling watching me take Jerry’s fist.
After the two of them had officially popped my cherry, I needed a break. I’d just had my first fists and I was sore. The other men were all smiling and laughing. I thought something was wrong, so I asked if everything was okay. Then they chuckled again. “Guess we’re going to need to find a new Top”, one of them said. “Guess you’re right”, I replied.
I still like to fist, but now I’m equally likely to be in the sling as I am to be in front of it. Now if I could just get two fists in…