The first time I tried fisting, I was with a woman. Like many of the kinks I’ve eagerly stepped up for, always a curious cat, I was hooked. She and I had been playing over a few spring months exploring bondage, spanking and strap-on play together; once soaking through my pants coming on me while I wore one of her cocks. She instructed me on the finer points of fisting before welcoming me to try it out. I will admit I was worried I might hurt my dear friend, or that my hand surely couldn’t fit comfortably inside her little cunt, but she coached me through until the grin on my face was from ear to ear and her smile had been replaced by other expressions.
A couple years later I met my first size-queen of an anal slut. Quite enthusiastic to share his kinks he brought out his favorite massive toys: A variety of plugs and dildos. He admitted he was attracted to my hands wanting to know if I had any experience with fisting, he wanted not one fist, but both of my little hands in his greedy ass. Another first for me, I eagerly agreed to indulge his kink after the proper negotiations. Donning gloves I warmed up my eager butt-slut, enjoying his vocal encouragement. No sooner than one fist was in he wanted my other hand inside him. I prepped my other hand, making sure my fingers, palm and back of my hand were evenly coated in lube. I ran a couple fingers along the outside, his anus hugging the heel of my hand. I slipped my first finger in, working slowly, adding one after the other while he grunted like a pleased little piggy.
When my hands slid home the sensation was oddly like being in bondage, kneeling behind him with both hands firmly planted in his ass, one cupped inside the other as if I were contemplating a softball I was about to pitch. Both my hands were there to stay. I pressed on, grinning like I did the first time I had my hand inside a woman.