Fisting Fellowship: A Sexual and Spiritual Journey

This is the first chapter of a multi-part story based largely on events from my past. The following content depicts sex between consenting adult males. If you are not over 18 or it is illegal to read this where you live, or if depictions of hardcore anal sex involving assplay and fisting disturb you, then do not continue to read this. You have been warned. On the other hand, if you like these things, then I hope you enjoy reading this and it gets you off.

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Mark and I grew up together in a small Midwestern town, and we came out to each other when we were fifteen. We talked often about sex and the men we thought were hot. We both obsessed over one of the high school coaches, a lanky brunette with green eyes and a hard, tight, perfectly hairy body. Coach Orr was one of the hottest men I've ever seen. He was the swim coach for a while, and the sight of him in that red and white striped Speedo inspired many a boner. He was the first man I encountered who had abs so defined that I didn't even know what I was seeing when he caught me staring at his torso. He just smirked at me while I tried to hide my hardon and dove into the pool.

Mark and I jerked off together many times while fantasizing about sucking Coach Orr’s cock. I told Mark I wanted the coach to fuck me in the locker room showers. He made this kind of weird face and said, “I’m not into that.”

Every once in a while, Mark and I would drive to the university town two counties south, where we'd raid the bookstores and buy tons of gay porn. He liked the really vanilla stuff, while I was slowly developing an appetite for some of the more hardcore content. When the camera would get in real close to a guy's hole being fucked, he'd complain, "I don't like looking at that." On the other hand, I loved it. To this day, the sight of a hard dick pounding a hairy manhole gets me horny as hell and hard as a rock.

Mark was tall, dark, handsome and hung. He had one of the prettiest cocks I've ever seen. The big head was a lovely light purple that capped a long tan, veiny shaft. Whenever we jacked off together, I'd stare at it, studying it, and I fantasized about sucking him off or having him fuck me with that beautiful tool. Unfortunately, he was quite uptight and a bit of a prig. Whereas I was always eagerly expounding on what I wanted to do with other guys--and it was a lot--he was always saying what he didn't want to do. His list of turnoffs was long, and it included many things that excited me. Mark could also be very moody and condescending. One evening he snapped at me and told me he didn't want to jack off with me anymore. He said he wasn't attracted to me because he considered me like his brother. He wasn't interested in going any further, and he felt we should stop having our j.o. sessions together. I was a little hurt, but I got over it quickly and moved on to other guys, which turned out pretty damn fine for me. (Mayble I'll write about that someday.)

Despite our problems, we managed to stay in relatively close contact over the next few years. While we were in college, he told me he had a boyfriend who really loved to be fucked, so I knew he'd at least started to have anal sex. A little later on, he told me he'd been fucked himself, and he didn't mind it, but he preferred to top. I kept a mental note of his sexual awakenings, since he'd been so much of a prude when we were younger.

One time, when I visited Mark while he was in grad school, we were both looking out his living room window at a hot little redneck who was working on a car just across the street. The guy was a wiry blonde with a taut, tanned torso. He strutted around shirtless, wearing only a pair of faded jeans and beat-up work boots. A cigarette, whether lit or unlit, hung perpetually from the corner of his sexy mouth. The hood was up on the front of the car, and the hottie had practically crawled inside. Mark's apartment was on the second floor, so we were looking down at this perfect little ass packed into worn denim, with a handkerchief peeking seductively out of the right pocket. Since the young man's top half was hidden under the car's hood, we could easily focus on what was most important. Mark shifted slightly toward me while keeping his eyes glued to that wonderful butt, and he said softly, "He works on that car practically every day, and I just want to go over there and ask him if he's ever had his ass eaten out by another man."

So it turned out Mark enjoyed rimming! I figured that was some pretty good progress for him. I had to laugh a little, "You think you'll ever get your tongue up his butt?" He grinned back, "I wish, but I don't want to get beaten up. The people who live over there are pretty rough. They get into a lot of fights with the other people in this neighborhood." I slapped him on the back and chuckled, "Sounds pretty hot to me!"

I was living in New York City at that time, having a lot of fun adventures with my friends and lovers. As it does with many of us who end up living there for a long time, the city had gotten into my blood, and I rarely had the urge to leave it. After Mark finished grad school, he moved first to Dallas and then to Los Angeles and later San Francisco, following jobs where they led him. He didn't seem to have a particular place that he called home. He visited NYC occasionally, and we had some good times, but it seemed he didn't feel comfortable there after more than two or three days. He said New York was just too intense for him, and I could always tell when he started itching to leave.

After a while, when he was living in Los Angeles, it got to the point where Mark and I weren't talking or writing to each other as much as we had in the past. He stopped calling me, and if I called him, he'd talk for a minute or two, then make some lame excuse to get off the phone. If we both returned to our midwestern hometown at the same time, we might see each other and have a drink, but he never seemed to want it to last very long. We communicated just often enough to find out about love affairs and relationships. Sometimes he'd send me a nice Christmas card or a funny postcard, but something in him seemed to have changed. He was very edgy and quick to anger, so I pulled back even more. I wondered if I had done anything to offend him.

Then, just before I turned thirty, I had the good fortune to meet an amazing, sexy, smart man who became the love of my life. And I'm ashamed to say, I kind of forgot about my friend Mark. My new man took up all of my time. I was head over heels in love, making a profound connection with another guy and having the kind of blazing hot sex I'd always dreamed of.

Bill was eight years older than me, a successful artist and amazing human being who changed my life, especially my sex life. Bill stood at 6'6", a Scandinavian viking of a man and a wonderfully nasty pig. We fell hard for each other and moved in together after only three months. I knew it was risky to take things that fast, but it turned out to be the best decision I ever made. For one thing, Bill was totally versatile and knew exactly what he liked in bed. His dick was almost as thick as a beer can and nine inches long when hard. As much as I loved getting fucked, taking his huge schlong could be a challenge, and we both knew it. One night as we started for bed, he stopped me, turned me toward him and looked through my eyes, straight into my soul. "You know I love you, right?" I shook my head yes. "And that I would never do anything to intentionally hurt you." Again I shook my head in the affirmative. I couldn't speak. I could sense that what was to come would change my life forever. "I want to show you some things that might be a little intense for you at first, but I'm almost certain you're going to enjoy them." We continued to gaze into each other until he put his big thumb on my lower lip and pulled it down gently just a bit, before he leaned in and gave me the most intense kiss of my life. (I can still feel it.)

We undressed and reclined on the bed. He pulled me close to him and spoke softly, "Our sex life is amazing, but I need more. There are things I like to do that we're not doing, and I don't want to go to other men to find those things, because I'm in love with you, and I don't think either one of us wants an open relationship, at least not right now." I almost started to cry. His big arms hugged me tighter and he continued, "Also, when I'm fucking you, I can tell you're enjoying it, but I'm so big I have to hold back when I really want to pound the hell out of you. I don't want to hurt you, and sometimes when I get a little rough, I can tell you're in pain."

"It's not that bad. Most of the time it's not a problem."

He gave me a serious look. "That's because I'm not fucking you nearly as hard as I want to. Seriously, I'm not."

I turned away from him and looked at the wall. "So what are we going to do?"

He pulled me back to him. "There are things we can do make it easier, but you're going to have to want to learn, and it might take some time to get there."

At first, I was scared and felt a bit rejected, but I both loved and lusted after him so much. He was my ideal man. I really wanted to please him fully, to give him everything he wanted. So we started down an amazing road of sexual exploration that resulted in years of incredible satisfaction and physical harmony. The first thing he taught me was how to really clean myself out in preparation for a brutal fucking and then later, much more. I had douched myself out before on many occasions, but Bill taught me so much I didn't know about my body and exactly how much my ass could take without causing problems.

Since he was such a versatile pig, Bill usually did to himself first what he did to me later, showing me exactly what he wanted. When we got in the shower one night, he took the douche nozzle and stuck it up his hairy blonde butt. I almost came spontaneously on the spot. That night we did longer enemas than we'd done before, fucked dildos bigger than I thought either of us could take and used up a ton of lube. I was amazed at how much his hole could manage. One of his toys was the size of his forearm, and he had no problem sliding more than halfway down its length. He bounced up and down a few times before he rose off the thing, flipped on his back and asked me to fuck him with it. "Start slow. Open me up and then push it in and out gently until you get to the point where you saw me take it just now. Then hold it there and let me get used to it."

I was nervous about hurting him, and he could see it in my eyes. "I'll let you know if you need to stop. I can take it though. You don't know how much I want you to do this to me."

Now, as big and handsome and manly as Bill was, I was no little twink myself. At the time I was 6'2" with wide shoulders and a swimmer's body that I had kept in good shape since the time I'd taken a weight training course in college. (That class was a lot of fun! It was led by the university's head football coach, so several of the team players were enrolled. I ended up having a good time with one of those boys for the better part of my senior year. He drove a pickup, which I found sexy as hell, and we'd drive out to a secluded part of the woods, put a couple of blankets down in the bed, and suck and fuck each other until our dicks and buttholes were raw. Anyway, I digress.)

Bill had his legs in the air, waiting for me to fuck him with that big dildo. I looked down at his lube-covered hole and for the first time I saw it really gaping, practically winking at me as his hot breath heaved his body with anticipation. That's all it took. Any fear or trepidation I felt up to that point just evaporated from me, and I was filled with a primal lust I'd never felt before. My nostrils flared and the smell of his sweaty body overwhelmed my other senses. I placed the head of that big toy against his hole and began to push it into him. The deep moan he let out led me to an even greater frenzy of lust. I became an artist myself that night, an artist of men's asses, especially Bill's. Once I got that dildo to the point where he wanted it, he reached over to the nightstand and opened a bottle of poppers. "Just hold it there for a minute while I take a couple of hits."

He held the bottle out to me, but I shook my head no. I wanted to be fully present for what I was about to do to him. (Besides, I've never really liked poppers. They give me terrible headaches.) He set the bottle back down on the nightstand, and we both readjusted ourselves slightly. I saw him wince a bit, but he immediately met my eyes. "I'm okay. Just keep holding it there for a few more seconds." I pulled one of his feet up to my shoulder and rested it there. I turned my head to lick the side of it, from his heel to his big toe and back again. I could feel testosterone and adrenalin coursing through my blood and my dick was harder than ever.

I locked eyes with him. "What do you want me to do to you now?" I grinned and jiggled the dildo just slightly. I could see the poppers beginning to take effect and his eyes rolled back as I vibrated the big toy in him.

He recovered quickly. "I want you to slowly pull it out so only the head is still inside me. Then push it all the way back to where it is now. Do that a few times before you pull it all the way out again."

I saw his face contort with ecstasy while I did exactly as he instructed. I was learning to gauge the responses in his body as I watched him experience the intense pleasure I was giving him. I deliberately stroked it in and out of him many more than just a few times before I finally pulled it all the way out. His hole made a series of delightfully nasty sounds as the dildo popped out. He gave me a look, "You're an evil bastard, aren't you?"

I chuckled, "I'm learning. I have a good teacher."

He sat up and lifted the dildo out of my hands before leaning in for a sweaty kiss. "Well, now you're going to learn my favorite thing in the world. I'm going to teach you how to fist me." He flipped over on his hands and knees, presenting that incredible ass to me. His hole was wide open, dripping with lube and ass juices. Instinctively, I pressed my face into his wet, hairy crack and inhaled him. I licked and bit gently at his flesh until he was moaning again. I had rimmed him dozens of times before, but this was something entirely new, and I loved it. I knew we'd be like this again, many thousand times over.

We locked eyes and took our time. He talked me through every step, and I took to it like a fish (fist?) to water. I reveled in the sensation of my hand and forearm probing his hot meaty insides. Our bodies meshed together perfectly. We reached my favorite part of sex, where we both felt like athletes, sweating and competing together to get to that transcendent place where we lost ourselves in the rut.

When his whole body began to quiver, I came back down to earth a bit. By this time he had flipped over on his back, and I was halfway to my elbow, watching him like a hawk. He did seem like my prey. He exhaled sharply twice. "Slow down the fucking a little, and pull out until just your fist is inside me." I did so. "Now push back in a bit and pull all the way out." I pushed back in and twisted my hand as it passed his protate. I twisted it again as I pulled back the other way. His eyes popped open twice as wide as before. He howled like a wolf. His body shook and quaked. His dick erupted, first a short stream of piss, then long ropes of cum. I was on my hands and knees between his legs, my face covered in his piss and cum, looking a bit stunned as I pulled my hand out of his quivering hole. It gaped open before me, then bloomed into a red rosebud of his flesh, the most beautiful thing I'd ever seen. I noticed his asslips looked a little puffy. I wanted mine to someday look the same.

We stayed like that for a minute. He was flat on his back, chest heaving. Finally, he lifted his head and looked at me. I was still a little shocked. He laughed at the sight of me covered in lube, piss and cum. "Serves you right, you little bitch. I didn't know you were going do that."

I looked back at him, amazed at what had occurred. "What just happened?"

"Those little twists you threw in at the end gave me a full-on anal orgasm. Two of them, as a matter of fact. You sure you've never done this before?"

"Never."

"Well then, you're a natural. We're going to do that again. Soon."

My mind raced with the possibilities. "When are you going to do that to me?"

"Give me a few minutes to recover and we'll get started. But you're not ready to get fisted yet, so we're going to try something else."

That night we stayed up until 2am stretching my hole with dildos, a couple of butt plugs and several of the thick fingers from each of his hands. We took breaks to make out and talk about fisting and other kinds of assplay. I confessed that sex toys had always interested me, and that I had sometimes watched fisting porn and found it hot as hell. I just never thought I'd be as capable as the men in those videos. I asked Bill a LOT of questions. He answered them all honestly. He admitted that some risk was involved, but it was also very possible to minimize it. He began showing me the differences between width and depth. By the time he finished me off at the end of the night, swallowing my load as he did, my hole was opened wider than ever. I was practically cooing as he brushed his fingertips along the edges of my new gape. He grabbed me by the ankles and spread my feet high up over his head, taking a good long look at his handiwork. He dropped my ass back on the bed.

"Now we're going to make sure it stays that way for a while." He gave me a rather sinister look and reached for the smaller of the two butt plugs he'd previously used on me. He pushed it gently inside me and held his hand against it so it wouldn't pop out. Then he rolled us both over on our sides, holding me close with his dick pressing against the base of the butt plug. "We're gonna stay like this for a little bit. I wanna see if you can sleep with it inside you."

Almost a year later, I took his hairy paw for the first time. He had huge hands, so during those months we had to be patient as I learned to take bigger and bigger plugs and dildos. When his knuckles passed through my first ring, I almost passed out. I know I saw stars. But I wanted his fist inside me so badly. I worked with the intensity of it, as he had taught me so well. I didn't feel like he was hurting me, but my poor brain struggled to cope with the incredible sensations sweeping through my body.

Bill kept his hand motionless inside me for what seemed like an hour. Maybe it was. We'd had a little whiskey and smoked some weed, so I was pretty high. Finally, he rolled his hand a quarter turn inside me, just enough to cause a few drops of piss to erupt from my hard cock. It wet his chest hair a bit and he pulled me closer. I was standing in front of him with my legs spread, a string of piss and precum hanging to the floor from my erect penis. He was on his knees, clasping me to him tightly with both arms. His face was level with my navel and he kissed my belly.

"Do you think you can walk a little? Just enough to back onto the bed?"

"I think so."

"Maybe I should pull out. I didn't mean to get my fist into you in this position. I got a little carried away when your hole opened up like that for me. I didn't expect it so soon."

He'd been on his knees sucking my dick when he reached around and pulled my butt cheeks apart. He started working my hole with fingers from both hands, occasionally reaching down to coat them with more lube. He pushed a big glob up into me and coated my insides with it. A dozen well-used dildos and butt plugs were scattered on the floor around us.

"We both got carried away. I sat on it as much as you pushed it into me."

"What do you want me to do?"

"Give me another minute." I ran both hands through his hair. Touching him like that always soothed me. He nursed my cock a little but otherwise was completely motionless. I looked down and found him already looking up at me. I'd never seen such an expression on him before. For the first time since I'd known him, he looked helpless, like a little boy. I felt such a rush of feeling go through me that it relaxed me enough to sink a little deeper onto his hand. We both moaned.

"I think I can make it to the bed now." I backed up a little.

Still on his knees, he shuffled slowly toward the bed with his fist in me. The sight of him crawling like that made me laugh. My body shook slightly on his hand and I felt another wave of pleasure. I lowered myself carefully onto my back, pulling my legs back and raising my feet to his shoulders. He stood up as I went down. His hand stayed inside me the whole time.

Then he was hovering over me, gazing at me with such a mixture of concern and lust that I couldn't help but raise my head to kiss him. That relaxed me even more. He grabbed the poppers off the nightstand and handed them to me. I didn't refuse them that time. I opened the bottle and took two long draws.

A few minutes later, I had an out-of-body experience. He'd gotten enough confidence to slowly pull his hand out of me and flip me over on my hands and knees. I was face-down-ass-up. He dove into my crack and licked my hole like a man possessed. His stubble on my tender skin drove me crazy. He pulled my dick and my balls down just enough to hurt a little. He let go of them, reached down, and started coating everything with greasy lube. He pushed another big glob inside me and spread it around with his fingers. He fucked the wide head of my favorite dildo in and out of me. He worked my hole with both hands until I begged him to get back inside me.

I felt him pull back, and I knew his eyes were taking in the sight of my back end before he wrecked it once and for all. I felt his left hand against my hole, as his fingers and thumb pressed gently inside. He paused a moment. Suddenly he smacked my right cheek hard with his other hand. It was such a shock that I barely felt his knuckles press through my asslips and fill my insides with his entire paw.

I gasped, "Now who's an evil bastard?"

Thirty minutes later I floated down from the ceiling. We were both covered with sweat and cum and a bit of piss. He was lying beside me stroking my head, caressing me, whispering to me, telling me how excited and proud of me he was. I wasn't sure when he'd turned me over on my back. I couldn't move much of anything below my neck. I was a little numb all over, but I had never felt so satisfied, so complete. As my body recovered and sensation returned, I reached down to feel my hole, which was gaping wide, pulsing and very wet. I realized then, that in the middle of all our ecstasy, he had pulled his hand out just enough to jack off into his palm and push his cum into me inside his fist. We had seen a couple of guys do that in a video we once watched, and I told him I wanted him to do that to me. I scooped up as much of his cum as I could recover, held it over my open mouth and let it drip down on my tongue. It tasted a little greasy mixed with the lube, but I didn't care one bit. I swallowed it all like a greedy whore.

Bill was watching me with both a look of wonder and a devilish grin. He reached down to my hole and repeated what I had just done, only dripping it into his own mouth before he swallowed. He licked his fingers clean. "I don't know if you remember, but the first time you came, I scooped it up and put it on my fist, so that's both of us right there."

"I want more."

As he started to sit up, he said, "I live to serve." He grabbed my ankles and rolled me up onto my shoulders. He sucked as much out of my hole as he could gather, letting my legs down just long enough to share cum-sloppy kisses with me. Then he did it again. And again.

I noticed his cock was getting hard. I reached for it and began jacking him. "I don't remember cumming twice, but you said I did. And you only came once. That doesn't seem fair." He was still between my legs so I pulled them up and offered my gaping new mancunt to him.

"Are you sure? Aren't you sore?"

"A little. But besides the fisting you just gave me, I don't think I've ever wanted anything more."

He was too gentle at first, so I grabbed my thighs and pulled them back, straightening my legs until my feet were as high up and fair apart as they could go. We were nose to nose when he stopped balls deep in my freshly wrecked fist hole. His face was a question. I answered his gaze, "I think it's time you pounded the hell out of me." 

And so he did.

Next: A Fellowship of Fisters