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Fist fuck
I am in college, in Philadelphia, 20, 6', 185 lbs., 7" cut, white, bi, and horny most of the time. I live in the dorms, in a single room, but am dorm proctor for 37 mostly Freshmen, and they are always knocking looking for help with chemistry (my major) or life (only 3 years older but it seems a decade older than some of them who have the mind sets and/or experience of 10 year-olds).
I have a good internet connection and porn is always available, and I got to wondering about fist fucking. Not that I wanted my ass to be stretched like that, but I was curious. The most that had ever gotten in my ass was 3 fingers, the most I had ever gotten in anyone else's was 3 fingers, although I had put a bigger dildo in a guy's ass once.
So, I went on line, and advertised myself as a "novice FF top seeks experienced FF bottom for education in the art, walking distance from Center City, or near SEPTA line from Center City, picture, preferred," along with my stats and a body pic, showing me hard. Within an hour I had 17 responses, after two hours, 29. I waded through them, eliminating the ones which involved a location that did not meet my specs, the ones who could not host, the ones with no picture, and the ones who just sounded "off".
That left 9. I looked at the profiles of the 9 and narrowed it down to 4 based on the stats and the pictures. I put them in an order of distance, 3 were in "walking distance", and went to the nearest one first.
The address was in a rundown part of the city, mixed race, safe enough in the daytime for a white guy, and having made contact by text, showed up at the door, rang the bell, he came down to let me in. He bore no resemblance to the picture, either it was someone else, or it was taken 40 years ago, he was very out of shape, smelled like ass, and was smoking a cigar. He was also very fem, said, "Hi, honey, come on in." He was not my style at all, I made apologies, and got out of there. I contacted guy #2.
He was in walking distance from the first guy, same neighborhood, gay flag in the front window, Black, he looked at me, said, "Sorry, I only do Black guys."
I said, "Did you not see my picture?"
"Yes, but I didn't believe it."
So, no more being said I contacted guy #3, he said "come on down", and, I got on the subway. Pay dirt. Nice row house, well kept, inside was really nice, he was really nice. Maybe 35, white, 5' 6", 145 lbs., athletic, great wide smile. He was wearing black trousers with a red stripe down the side. He had a black T shirt that was tight, and showed his great chest, and had the initials FFA on it. "C'mon in," he said, "can I get you something to drink?"
"A Coke? Or something like that?"
"Coming right up, ice?"
"Please."
We sat and talked. He wanted to know what I wanted to know, and to do, and why, and what gay sex I had done. I told him, he told a few stories about how he got into fist fucking, what it felt like to him, and the disadvantages and risks of being a bottom, and how he minimized them, which he would tell me as we went along. He also told me he was a surgeon, and so was very familiar with the anatomy of it all. He explained that FFA was not Future Farmers of America, but Fist Fuckers of America, and that the black pants with the red stripe were code for it as well.
"Let's go to the playroom," he said, and led the way down the stairs to the basement level where the walls were all black, the lighting subdued, and the center of the room dominated by a leather sling, hung from chains from the beams in the ceiling. To the right of the sling was a table with long rubber gloves, a big tin of lube, alligator clips on a chain, handcuffs, leather and metal, and other "tools of the trade" as he called them. Unlike guy #1, he smelled good, and unlike guy #2 he was ok with white guys.
The floor was carpeted except at the foot of the sling where it was tile. "Time for clothes off, and some vanilla sex," he said, and we began by making out, feeling each other up, he dropped to his knees on a pillow and sucked my cock. He used his tongue, he used great suction, he got it down his throat and swallowed on it, he knew all the moves. Meanwhile he was playing with his cock which was very hard, a big mushroom head, shaved balls, big eraser nips, I played with his nips, "Pinch them, hard," he commanded. I did. He moaned, which, with my cock in his mouth, made me shiver with pleasure.
"We'd better cool it a bit," I said, "or I will come before the main event."
He got up and got onto the sling, "Help me get my feet up in the stirrups." I did. There he was, ass up, pink hole exposed to the world, or, at least to me. "Do you rim?" he asked.
"Never have," I replied, "and am not sure I am ready for it."
"Well, if you want to, here is a golden opportunity, all cleaned out and ready to feast on."
"I am still not ready, if it is ok with you, what is next?"
"Put on the rubber gloves -- I already checked out your fingernails and you did cut them close, so they are ok. The biggest risk to me is having something, like your fingernails, scratch the lining of the rectum so that a virus, like HIV, or bacteria, can get through into the blood stream. So very well cut, and smooth, fingernails, plus the medium duty, long sleeve, rubber gloves, are for my protection, not to keep shit off your hands, which, they do quite well, but that is not their reason for being."
"Now, let us do whatever else two guys do, normally, and as we move along, play with my hole, loosen it up, one finger at a time. The anus is a remarkable thing, if one goes slowly it can stretch remarkably large without tearing or hurting
And so we kissed, and played with each other's cocks, and balls, and nips, and sucked each other a bit, all the while me using one hand on his hole, circling, rubbing, probing, getting a finger in, then two, then three, all without breaking stride on the vanilla sex we were doing. He looked at my hands, "Make a fist with each of them, and let me see which is smaller." Being right-handed, my left was clearly smaller, something I had never noticed. "Use your left from now on, here you can wipe the lube off your right glove."
So, I continued my probing with my left. He was clearly enjoying it. "Time to take this seriously," he said, "try 4 fingers." I did. "Now fold your thumb inside your fingers, this is the toughest part the first knuckle of the thumb is where most hands are the widest. Use more lube, lot of it, it cleans up but take it really easy, do not force it, and let me go for the ride." I did. More lube, worked my hand, all four fingers in his hole, a little in and out, and, suddenly, he took a deep breath, let go of his cock, and it was in.
"Hold it right there, you can make a fist, thumb inside your fingers." I did. "Now, gently pull back, stop, push in, stop. That is the limit, each way, try it again, so you get what I want." I did. "Now just do it." I did. He was moaning and clearly was in extreme pleasure. His hands were on his nipples. His cock was stiff and dripping precum and throbbing all by itself, my cock was standing strong and throbbing as well.
After about 5 minutes of this, me working my left fist in his ass, and playing with my cock with my right, and lots of lube, he groaned and his cock spurted cum up to his face, his pecs, and as the spams lessened to his belly. This was so hot that I came in my right hand just watching him cum, and feeling the spasms on my left fist.
"Stop," he said, "just hold up until I finish cumming." I could feel the spasms continuing and his cock was still jerking. "Now, undo the fist, and let me push you out." I did, and he did.
His ass was prolapsed, the red lining extending out of the hole. "Push me back in, very gently, then take off the gloves, and put them in the wastebasket next to you." I did. "Take the paper towels and wipe me up, and wipe up your cum, you did cum didn't you?"
"Yes, it was really hot."
"Help me out of the stirrups, and after I have rested a couple more minutes, let us go back upstairs and talk a bit, about doing it again, and maybe exploring your ass one day soon."
We did, had a snack and a glass of very good white wine, and talked about how he got into it, more about the dangers, and more about the extreme pleasure it could give. My next visit is another story.