I’ve attempted fisting with two previous encounters with men, and without success. Although my hands are slim and my fingers are long, my knuckles have always been an obstacle for a smooth transition inside the receiver’s body.
Other encounters involved the use of poppers, which are an inhalant used to produce a short high and relax all of your muscles, including your sphincter muscles, but this still wasn’t sufficient. I learned that education can go a long way - for both giver and receiver.
This past week, we attempted again but without success. However, I had him face down, ass up, fingers almost fully inside and, using my Hitachi magic wand, produced an internal prostate orgasm - and I know this because of the small amount of semen produced as a result of the stimulation (despite his track record).
The Second Time Meeting For The Fist Time
I met Mr. S once before. During our first encounter, he brought a gigantic dildo - the largest I’ve ever used on someone and have seen someone use in front of me. It was a thrill and I was amazed. I was motivated to get my fist in someone, and it seems like he had the experience and the anatomy.
I ordered the toy for him online - the one that I’m wearing in the picture. Finally after a few weeks of back and forth it arrived. We were excited.
He said he has a toy similar to this one but he chose this design because of the space from the base of the dildo to the end of knot. The toy felt hard with very little give. I wondered how we would fit the whole thing inside of him.
He asked me to measure the length. I told him it was about 5-6 inches, which is a good length for his pleasure. It's not the length that gives pleasure - but rather the girth that's the most important.
He knew about my goal to one day get my fist into someone - and he wanted to be my first. He arrived all giddy - excited to see his toy. He unwrapped it from the plastic cover and he put it into his harness and strapped it on my body tightly. Typically I like the harness to be a little looser because it gives me more control over how I use the dildo but, since it was my first time with something this large, I let him strap me up tightly.
We started caressing. I was tickling his back and teasing his cock, ass and balls. We were on a tight time limit so he was ready to take his brand new red dildo and, hopefully, get the knot in all the way.
He hopped up on my milking table/massage table - face down, ass up. I got behind him and lathered him with the lube he provided. I put one finger inside of him first to gauge how ready he was to take this massive dildo. To my surprise, it slide it so well and so easily. Typically it takes a little bit more to warm others up. 'This will go in no problem,' I thought.
I slide the tip of the dildo in and he started moaning, pulling it in and out until I stretched him out the circumference of the second largest part before the knot. In and out. In and out. He was ready to try the knot. He pushed his ass up against the knot. Pushing, pushing but to no avail.
“Do you want to put your fist inside of me?” he asked. “I’m ready," I replied.
I slid the dildo out and slowly started to slide all 5 fingers inside of him, with my fingers in the entry position. Slathering him with lube as I entered and exited, slowly. Making sure to work my hand in slowly and take my time. Feeling his sphincter contract to kick me out and relax for a deeper entry.
We reached my knuckle. “What do I do now?” I asked. He said “I’m going to start winking”. “What’s that?" “You will feel my sphincter tighten up, and when you feel me relax, you will just go for it and push.” (I imagined the winking of an eye - which I assume is where the analogy comes from.)
As my hand slid in, my fingers had no where left to go. My fingers started to curl up into the shape of fist. I was fully in the anal cavity. ‘I get it now - this is why they call it fisting,' I thought.
“There you go!” he said proudly knowing that he “popped” my "fisting cherry”. 🤜 🍒
After I was wrist deep, I started moving my fingers around the best that I can to stimulate his prostate. He was moaning in delight and pleasure with every tickle and stimulation from my movement.
“OK - now I want to try to get this knot in," he said. “Okay!” I said excitedly. I slowly removed my fist and my fingers began to uncurl. What came with it scared me for a moment. There was some blood and I was worried that I had caused damage or hurt him.
I have given people prostate massage or pegged people before. Very rarely have I ever seen blood (maybe once or twice in my experience) but this was different. There was a lot more than I’ve ever seen before.
“There’s blood”, I said. “Are you okay?”. “Yes, don’t worry”, he reassured me. “This is called pinking and this happens upon first entry. It’s all of the tiny blood vessels in my anus popping, but once I’m warmed up, this will all stop”.
After washing my hands thoroughly, I came back with the strap on to try again. We got the knot about half way in but we weren’t able to achieve our goal. He had to run.
Even though he didn't climax, he still sent me a text on his way out.
My Takeaway From This Experience
Overall in this setting, education would have gone further for me. I think if I had known about pinking before I had my fist experience, I wouldn’t have been as concerned and enjoyed the experience that much more. I was grateful that I had an excellent guide to walk me through the process.
The connection between us was electric. It wasn’t about me dominating him or taking control but rather it was us communicating - me sensually giving things to him slowly and him asking for things or taking things at a faster pace and when he was ready.
It’s amazing how there’s this level of connection between the one fisting and the other being fisted. It was constant communication with him. Asking him if he’s OK. Asking him if I can push or if I should pull out. Him giving me suggestions and me having the option to decide what I wanted to do. It was overall a very connective experience, and very pleasurable for him and for me because he was able to enlighten me and I was happy to share this fist experience with somebody who was able to educate me and guide me through the whole process - which was beautiful because I’m usually the one guiding and taking charge.
Thank you Mr. S. I look forward to more fisting adventures and I have a lot more to learn and understand. I also look forward to sharing this knowledge with others through this blog and also face to face.
Stay tuned. 💛
My regular friend once tried to fist me. Omg it felt so good. But he too, couldn't get past the knuckle. But the sensation....if you haven't had it done to your lady part then you should give it a go. Probably didn't help that he was in a rush. At least subconsciously, he was no doubt affected by that. Poppers are also great. I really don't know why women don't use them as well. It seems to only be a "guy" thing. But what a rush they give you as well. To feel an object entering you while on a rush is such an awesome feeling, I can almost feel you entering my willing ass now.