I'm surprised not to find more about anal fisting on this site. I'm bi sexual, and very, very hedonistic. I love to eat pussy and suck cock too. On some sites my screen name is "Tireless Tongue." I also love to fuck both men and women, although I like to fuck women more. I'm on the submissive side with men, and the DOM side with women. But, nothing is "etched in stone." These are just tendencies and preferences. I think I can get into most anything if there is a connection, or as they say, "chemistry." with my partner. Way back when, my girlfriend at the time, convinced a friend of ours who was Gay, and open about being into fisting, to do me. I was open to most things and willing to try most (with a few exceptions; scat, children, piss, severe pain just for the sake of torture) at least once. We both agreed to give it a try, and we decided that I should get undressed, and cleaned out with a nice cleansing enema (one of the perks of anal play), and then,get on my hands and knees, on the bed, and wait for him and the party to commence. I forgot to say there were a few other friends present. My friend who was doing me was very good, and went extremely slowly. Now I had had a good deal of experience getting anally fucked and loved it. Part of the thrill here, was first the enema, then the audience of a few friends and my girlfriend, and the anticipation. That, I think was the biggest turn on. Obviously, it's a VERY, VERY submissive posture to be in. And, as I've already mentioned, I'm sub with men.
Well, my friend had a great sense of Drama, aside from being good looking and a very sensual being. After I was cleaned out, and on the bed waiting on my hands and knees he prepped for the "deed." He took his time, and laid out towels, and brought out the a few dildos and then the Crisco. Then, when he was about to begin, he suddenly looked at his hands, and realized that his fingernails were too long to proceed. This was just as the HIV crisis was beginning and no one really knew about it yet. No one fisted in those days with gloves. He then went into the bathroom, got out a nail clipper and nail file, and proceeded to trim and file his nails. All the while having me retain my position which I was happy to do. I too have a sense of drama. And, besides, by this time, I was Totally Turned On. Finally, he finished with his nails and came back to my bottom. He started to rub my behind, massaging it a bit, alternating with something like caresses. He touched me all over grazing over my scrotum, my anus, and even brushing over my cock which was in a semi hard state at this point. Finally, after taking some time doing all this, he dipped his hand in the Crisco, and started by inserting his index finger in my anus. Slowly he moved his finger in and out of me, while turning it, and stretching my sphincter a bit, Finally, after he was satisfied that his one finger was going in and out of me easily, he went for two. He continued this same way, and did this progressively with each of his fingers until finally he had all five in my anus, up until the second set of knuckles of his hand. All the while I was still on my hands and knees letting him penetrate me at will, nervous with anticipation. Needless to say, i was becoming like a cat on a hot tine roof. As I was there, and excited to be doing this, I wanted it to happen already. Then, he changed his tactic. He started to put the slightest bit of pressure on his hand, pushing ever so slowly and carefully, all the while twisting it slowly clockwise, then back counter clockwise. He kept this up until he was right at the point of getting past the widest part of the hand, that second set of knuckles and getting his entire hand inside of me. I can't begin to describe the tension...in me, in the onlookers, my girlfriend, and, of course him. He was very sensitive to me, and as soon as he detected it coming, he pushed just a little harder and, the next thing I knew, He was completely inside of me. It's extremely difficult to sit here and write this account of what happened that evening, and describe accurately the feelings and emotions that I experienced. It was like nothing I've ever had before. To say it was ecstasy is a gross understatement. It goes way beyond that. Needless to say I was hooked. I never wanted him to come out of me. Of course though, after about 20-25 minutes, I reached my limit. There's only so much pleasure a person can take. Some years after that, when someone tried to pin me down to get me to describe the feeling, the only thing I could think of that comes close is: try to imagine a time when you had to urgently go to the toilet to move your bowels, or, alternatively, when you were full with an big enema. You had to desperately hold it in, and were going crazy doing so. Finally, you get to the commode and let it go. Now imagine that feeling multiplied by at least 10. That comes close to how it feels once the fister is inside you, fucking you, manipulating inside you, etc. This started a new chapter in my sexual being. I went on to enjoy this for years to come. I spent may nights at various clubs in NY, like The Hellfire Club, The Mine Shaft, etc. in the slings getting my ass worked on. Also at private venues as well. I also had a few girlfriends that, in addition to fucking me with a strap on dildo...a very large one, i might add, LoL, they got very into fisting me. I had one GF in particular that was unbelievable at it. I never saw anyone get as sexually excited in my life as she did when she was fisting me. When she was inside me, I would put my hand back and start to play with her clit. I have a great deal of sexual experience with both sexes, but I never, ever saw a woman as wet as when she was doing me. All I have to do now, if I want to smile is think of her doing me on my hands and knees with her hand up my butt.