I had placed an ad on Doublelist seeking a fuck and fist. I really didn’t expect to receive a response, but I did. He is 39, 5’10”, 185, hairy, beard, about 7” cut, and an experienced fister. His hands looked perfect for my first fist. We agreed to meet at a hotel downtown a few days after our initial contact. He seemed to like my thin frame, and was intrigued by the cock cage I had been wearing (been caged for several years by my partner who isn’t into fisting).
I brought with me a tub of crisco, j-lube, lots of toys (dildos sized 7”, 8.5”, 10”, a fisting dildo, and a huge thick black dildo very wide and about 18” long). I also had a fresh bottle of poppers. I got to the hotel first and took my time getting thoroughly cleaned out. I wore only a black Cell Block jockstrap and a leather harness. My cock already straining in the cage thinking of what would come.
He arrived at the agreed upon time, and he was better looking than his photos. We made out, and feeling his beard against my whiskers made me wild with desire. We walked over to the bed where he stripped and his cock was raging. He put a little crisco on his dick and pushed me onto my back while he raised my legs and pushed right into my ass. He began to lick and kiss my feet as he fucked into me. I wasn’t expecting to get fucked so quickly, but I wasn’t refusing. I enjoyed it. He shot his first nut inside me.
He reached over and grabbed the 8.5” dildo and began to fuck me with it while I hit the poppers hard. After a few minutes he pulled the dildo out and I sucked on it trying to lick off any cum that might have been on it. He then squat down and began to rim me. He was an expert and I was cooing. I reached down to pull his head deeper into my crack, encouraging him to eat my ass.
When he finished, he reached for the crisco and began to insert some into my hole. He grabbed the fist dildo, and I switched positions so now I was on all 4’s, and I hit the poppers again. He slowly inserted the dildo near my hole and I could feel the fist spread it wide, and then I felt it “pop” inside me. The fist felt so amazing inside me, he was stretching me. I took more poppers as he got the dildo deeper inside me as it’s length is a full wrist, narrow towards to fist, and it is wider toward the elbow. He began to punch fuck me it. I was moaning loudly, so uninhibited, and feeling so good. I reached to tweak my nipples while my ass rode the dildo. My dick was leaking pre soaking the pouch of the jockstrap.
My fister then pulled the dildo out and we began to make out again. While on all 4’s, he inserted his dick once more in my ass, and fucked in his second load. The crisco was melting and with his cum, I was well lubed and very wet.
After he pulled out, I was on my back once more pulling my legs up and open so my hole was fully avail to him. He began to stick some fingers inside beginning the fisting process. He pulled out and grabbed the mixed j-lube arms rubbed it all over his hand and wrist. I had a hood and blindfold on the bed and he told me to put it on. I did, and he then again started to finger my asshole. Only this time, he had 4 fingers in, and I could feel him entering with a cone shape as he pushed into me deeper and deeper.
He instructed me to take a very deep hit of poppers and to push out. I followed his instructions, and he pushed right inside. There was a “pop” as he pushed past my second sphincter, and his fist was inside me. I was euphoric. I had tried to be fisted a half-dozen times without success. He was patient and willing to work with me to get where we were, his fist inside me. He let it sit there for a minute so I can get used to the feeling.
I took more hits of poppers and he began to slowly rock his fist in a little deeper. The feeling was indescribable, more pleasure than pain, and I encouraged him to punch up inside me. The feeling and the pressure caused me to have an anal orgasm. I pulled off the hood and blindfold and saw the huge cum stain on my jockstrap.
Slowly he pulled his fist out. He went to his bag and pulled out a double sided dildo. We played with that taking turns bucking hips for a good amount of time before he shot his 3rd load of the afternoon all over his hairy chest and stomach. We pulled out the double dildo and I dove in to eat the load off of him. Afterwards, he grabbed the 18” monster dildo. He had me get on all 4’s as he coated it with lots of j-lube. I took yet more hits of poppers and by this time the room was spinning and I was spinning, I was really messed up. He pushed right inside and my stretched hole took the width in easily. Slowly, I felt pressure in my ass as he pushed the dildo about 10-12” inside me. That was the most I had ever taken of the monster dildo. My hole was stretched to maximum capacity and slowly he pulled it out. He said it was so hot watching my hole take that huge dick.
I thought maybe we were done, but while still on all 4’a he got behind me and fucked in another load, that was his 3rd inside me, but 4th overall. I was really impressed! He laid down on the bed and lubed up his hand and wrist with lots of crisco. And he held up his fist and said, “sit on it”. So I took more hits of poppers, which prob was not a good idea given how fucked up I felt, and began to slowly sink down on his hand, until once again he “popped” inside. I began to ride his wrist like a bronco it felt so fantastic fucking his fist inside me, and once again, I reached for my nips and I rode and rode him until I was sweaty and I came once again. This time I felt my ass muscles clench and twitch around his wrist and fist and it added to the intensity of the orgasm.
I slowly lifted myself off of him, turned around and thanked him for that, and kissed him in appreciation. I do have a pit fetish, and I slowly moved from kissing his mouth to licking and cleaning his right pit then his left. He scent sent me to heaven. He said “that’s right inhale the scent of your master. Remember it”. Oh I would and do!
With us totally spent, we headed for the shower and hopped inside. Making out under the stream of warm water. I soaped up his hairy body and he rinsed. Then he did me, only he slid wet and soapy fingers inside my hole.
We dried ourselves, he dressed, and he left. I was in a pair of briefs and I laid down on the bed, just replaying all of what had happened in my mind. I started to play way my nips again, and the craving for something inside me took over. I lubed up the fist dildo and placed it on the chair over by the desk where there is a mirror. I sunk down on the fist watching myself get off on taking the fist. Tweaking my tits and moaning so hard until a third orgasm happened. I’ve never had 3 anal orgasms in one day before. Heck, it’s rare that I even have one in a day. Fisting seems to really get me off.
I dismounted the fist and slowly got my things together and myself together. It was time to go home. If only my partner knew what had happened during the afternoon. I played it cool for the rest of the evening and felt an emptiness in my gaping hole all night.
So, I am due to hook up with this guy again in 2 days. I am consumed with what may happen and it’s been difficult to focus on anything else. I’m still locked up in my cage, but I’ve been leaking like a faucet for several days. I’m sure the first anal orgasm will be really intense and very quick, but knowing there will likely be more than one brings a smile to my face. Anyway, that’s my first fisting experience and hope you all enjoyed reading about it.
