I had heard of anal fisting before when I was a volunteer with Community Health Trust, a local clinic for the gay, lesbian, transgender and bisexual individuals. I had read some of the literature and saw that it was a risk due to the possibility of bleeding. So I assumed it was something truly hardcore that only men did to each other. God, was I innocent.
Later, I had a friend who was a leather dyke, who while she preferred to have sex with women, she preferred to torture the hell out of men. She enjoyed whipping men and had many submissives and pony boys in her stable. She had talked about fisting a woman and described it coming upon the most delicious chocolate cake in the world and indulging in it again and again, putting your fingers into it to break off a piece to nibble and that the more you dug your hands towards the center of the cake your discovered that it had a warm, moist center that just oozed onto your hand and that the taste was rich and exquisite. And that the warmth pulled you deeper inside and surrounded your hand with all the soft, moist cake around you.
She was a butch lesbian and not very attractive. She tried to lure me into bed with her but there was just no way I would. She scared me. She was obsessed with BDSM to the point of engaging her children unwittingly in her practice so I avoided any intimate situation with her, despite her many attempts. I went on to report her to child protective services anonymously though I think she figured out that it was me.
I dated a man in the mid-to-late 90's who loved making me cum. He had small hands and he would finger my pussy, stroke my g-spot and drive me wild. I don't know how we decided he should try to fist me but we did. Back then, I was self-conscious and not as easy-going as I am today. I never urinated in front of man and was very unwilling for one to see me. So while he tried to fist me, I'd get to where I felt I could open up for him but then I'd get a twinge in my urethra that I was going to pee so I tensed up. I didn't know about squirters back then and was terrified of wetting the bed. He and I would get together at least weekly and work on getting his hand inside me. He'd gotten pretty close once. Then there was a popping sound and a lot of pain, along with the sensation of having to pee so we backed off from it.
Years went by and I found this wonderful site called enemas4fun, aka Zity. I read about men and women who enjoyed it. It sounded amazing, intense and doable so I decided that I would love to try to be fisted. So whenever I found the right gentlemen for the job, I would tell him that I wanted to try it. I started posting and replying to messages by a very interesting gentleman who lives in my state. Like me, he has an interest in giving and receiving enemas. He also had a desire to be fisted. I didn't think it was possible but I entertained the thought. We took 9 months to a year to get to know each other before we felt ready and had the opportunity to meet.
When we got together for the first time, I gave him several enemas and he laid down in my bed where I massaged his prostate and worked my fingers inside him. His rectum was so soft and hot and I love every second of it. It was also tight so I didn't feel comfortable attempting to put more than the fingers he readily opened for inside him. He begged me to go further so I did. He was of the assumption that it was going to hurt so to just get the pain over as soon as possible and kept telling me to go faster than I thought he was ready for. But I did it his way and eventually worked my hand inside. I was freaked out, though, because there was some blood on my hands afterwards and I didn't feel comfortable causing injury to someone. It was however, quite a high to penetrate someone and to feel his hand sucking me in and beg for more. We tried it several more times over the months and eventually, I decided to listen to his body, not his mind, and I slowly, sensuously slid my fingers inside him and only pushed when he felt physically ready for it. I spent hours between his legs, gently stretching him and massaging his prostate until he was relaxed enough to take my hand without force. It went so much nicer my way, when I listen to my intuition and his body. It has been like that ever since and we both love it.
He has tried to fist my vagina but it's rather tight and short and his fingers are long. Thankfully, his hands are not huge and his fingers are not too thick. But it still hasn't happened yet. He is rather matter-of-fact about messes and wouldn't mind if something came out of my body so I don't worry about whether I accidentally urinate or if squirt. We just throw down a towel or under pad and do our best. He spends hours trying to stretch me while rubbing my g-spot. My pussy squeezes hand fingers tightly so his hands eventually cramp and his carpal tunnel syndrome flares up. He has managed to get his fingers and thumb inside me once and even beyond the widest part of his hand but my pussy was too short to accept his fingers so he couldn't go all the way to the end of his hand, much less to his wrist. For now, we've accepted that it probably isn't going to happen between the two of us.
Meanwhile, I look for a lover with smaller hands.
~ Dianne