I have been fisting my lover (whom I met here) for a couple of years now. It was difficult at first because he wanted to guide and direct me. He's younger than me by fifteen years and impatient so he would often tell me to push because he expected there to be some pain. And there was. And some mild bleeding as well. He's of the variety who thinks pain is going to happen no matter what so instead of slowly easing off a band-aid, he's the type who rips it off and screams in pain. I did it his way a while but knew it could be much better if he'd let me guide myself by reading his body language and hearing his moans.
After an enema series and after waiting a half hour or an hour to make sure there will be no surprises lurking around corners and in pockets of his colon, we begin. I would like to rim him but have only done it once or twice with him and he loved it so it's definitely something I want to do the next time we're together. I lubricate his anus and my hand and slowly ease my way inside with one finger, then two. I massage his anus with the two fingers working internally while my thumb massages it from the outside. I circle his anus several times while slowly fucking him with my fingers and insert a third when he's more relaxed and feeling good. I press against his prostate in what can best be described as waves. I touch my fingertips to his prostate then slide my fingers palm down flat against it, working from the tips of my fingers to where the fingers attach to the hand. Sometimes I use the back side of my hand instead so first the fingertips, then the knuckles stroke his prostate. This usually relaxes him further so I slip in a fourth finger and continue with the waves although I now take it up to the knuckles on the back of my hand. I will very slowly begin to push my knuckles deeper inside and it is a bit of a stretch even though I have small hands. It's the widest part of the penetration, thus far.
When four fingers fit comfortably inside him, I move my hand in and almost out of him, slowly fucking him. I move in circles around his anus and rectum to prepare it for stretching further to accept my fist. Sometimes I tuck my thumb under my fingers and insert it to right before the knuckles. This is usually the point where he wants me to push my hand inside but I try to pleasure him and wait until he's more relaxed so it doesn't hurt him. I lubricate my other hand and alternate my left and right hands, never completely leaving his body, but allowing my palms to glide against his prostate and each other so he always has the feeling of being penetrated and the feeling of deep prostate pleasure at the same time. I will sometimes stretch his anus by using three fingers of each hand and pulling gently in opposite directions in a circular motion while massaging his anus with my thumbs. He moans when I do that so I know he loves the sensation as well as the submission of being opened and fully exposed.
It is then when I'll slide the fingers and tucked thumb of my right hand inside him. I will slowly glide them inside until my knuckles bump lightly against his bottom. I very gently press my lubed hand further inside him with the knuckles being the widest part. I sometimes wiggle my fingers slightly to give him a little something to think about than my hand penetrating him, trying to get him to relax. I move very slowly, allowing him to adjust to the width and waiting for his sighs and moans to let me know it's time to press further. When I get to the widest part I turn my hand slightly to and fro to find the perfect spot which will let me enter him fully. When I find that spot, I slide my knuckles past it and glide on in. He prefers to have a little time to get used to the feeling of fullness so I'll just sit there and feel his heartbeat against my hand until he is ready for more. I let him guide me once I'm inside since I don't want to hurt him or tear the delicate tissues. Depending on his mood, I might just curl my fingers and just sway my hand against his rectal walls or press against them with my finger tips. He might want me to fuck him gently with my hand or sometimes want me to fuck him hard with it. He is often too sensitive for prostate stimulation so I may or may not stroke it while I'm inside him. Although one of the best orgasms he's had has been with me fisting him and stroking his prostate while I leaned down and took his cock in my mouth and sucked him dry. He found it amazing but exhausting. Too much of a good thing, maybe.
If you're interested in seeing pics of us playing, I uploaded a set of photographs from one of our fisting sessions in my gallery.
He once managed to get four fingers inside my bottom and two fingers in my pussy but as far as him fisting my bottom, I don't know if it is possible. I'm a wuss when it comes to pain and discomfort and his hand is so long and so large. However, I would be willing to give it a go sometime just to see. Not with the goal of fisting but with the goal of feeling good and relaxed and enjoying the exploration and sensations. Hats off to all the ladies who can take their lover's fist. Maybe I'll join your ranks someday. Until then, I'm perfectly happy warming my hands in my lover's very tight and delicious tush.