This story, and the one's that follow, have a grain of real life experiences in them, but I've elaborated on them significanty so they really are little more than fiction. But I hope you enjoy reading them.
The usual warnings apply. This story involves sex between consenting adults. If you're not over 18 or it is illegal to read this where you live, then please do not continue any further. You have been warned.
Fisting. The word alone seems to instantly divide gay men into two camps. Those who do or are interested and those who don't. Some simply aren't interested and leave it at that. But others take a highly negative and critical view of those who do. I'm not sure how or why this attitude came about but I suspect it is due to a view of fisting as inherently linked with an image of big hairy men in leather who swear, curse and spit at each other. Hands are rammed in arses in scenes that are almost bordering on psychotic. I've been fisted many times and none of my experiences fit with those I've seen on screen. This is my story.
Firstly a little about myself. I'm in my early 40s. I'm white, slim build, with a little chest hair which I usually shave off. I work out several times a week, a mixture of cardio and weights. I'm lean but not thin. I have some muscles but no-one would call me muscular. My cock is cut and an average six inches. I'm average height, about 5'7". I have relatively small hands although I didn't see how advantageous that would be if one got into fisting.
I'm not entirely sure how my interest in fisting began. I knew what fisting was, but the one time I had seen it on a video, it seemed so extreme and the actors so unlike myself, that it never seemed an option worth exploring.
When I was in my late 30s, my boyfriend at the time and I enjoyed using dildos. One was at the upper end of the human spectrum but none were outrageously enormous. Given we were both versatile and loved to switch roles, especially with dildos, we always douched as it made for some lengthy and fun sessions.
It all began during one session about five years ago. He'd already fucked me with his 7" uncut dick and I was now fucking Ed with a mid-sized dildo. Ed was also white, and a similar age, but was little taller and stockier. He had a bit of hair on his chest, but nothing extreme. I was lying next to him, facing him, my right hand between his legs and moving the dildo in and out of his arse. We were kissing passionately, our tongues dancing in each other's mouth, as I fucked him.
His arse had really loosened up and he just writhed in ecstasy when I would pull the dildo almost completely out and then push it back in. Sometimes, I would tease his hole with the tip of the dildo, he arse lips almost pouting to get it back in and then, just as suddenly, shove it back in.
After quite a while, I pulled the dildo out and set it aside and gently caressed his hole with my fingers.
"You want me to finger your arse babe?"
"Oh yeah," he replied. "Play with my hole."
I started teasing his hole and his arse with my fingers. This wasn't really unusual either as we'd finger fucked each other many times, although never with more than three fingers.
It's one of the quirks of nature that if you've had your arse stretched and you put something much smaller in, like a finger, the arse forms back around it, but not tightly. The sensations for the guy being fingered are always delightful.
"Oh Jim, that's fantastic," he gasped as my middle finger effortlessly slid in and out of his arse.
I began feeling inside him, enjoying the warmth and softness of his rectum. I quickly found his prostate gland and gave it a good massage. "Oh man, that's so good," he sighed. He was writhing about, enjoying the sensations emanating from his arse. Soon the solitary finger was joined by a second and then a third.
I kept probing his hole with my fingers and he urged me to push harder and faster. I don't know why, but I added in my little finger to the three others already stretching his hole. The addition of the extra finger caused his eyes widen and his head arched back. "Oh, yeah, stretch my hole," he said with a lusty grin on his face.
"You like your hole stretched boy?" I said with a smirk. We'd been together for a while and such silly fantasy talk was common in our sex life.
"Oh yeah, my arse is yours. Give me more."
And more was what he got as I added my thumb to the mix.
"Oh fuck man that's fantastic."
But instead of the vigorous finger fucking of before, I slowed down the pace and just applied more pressure, going a little deeper every time.
Ed was really getting into it. When he urged me to put lube on my hand, and took a couple of good snorts of poppers, I knew we had both crossed the line from finger fucking to fisting.
My hand kept moving in. I had just about reached the widest point when Ed suddenly looked worried.
"Are you ok, babe? Do you want me to stop?"
"I'm not sure. It feels so intense. I'm just not sure it will go."
"Take some really deep hits of the poppers, let go of your dick and just relax."
Neither of us realised it at the time, but that was the key. Because Ed was still stroking his cock, he was unconsciously tightening his hole.
I eased up just slightly, poured heaps more lube on my hand while he took a deep snort in each nostril and let go of his dick. I resumed the pressure and quickly reached the widest point again.
Ed unconsciously started tensing again. When he realised this he relaxed, breathed out slowly and that's when it happened. My hand slid inside. His arse lips were now around my wrist.
I've never seen anyone's eyes go so wide. "Oh fuckin hell Jim, I, I, I don't believe it, you're inside me," he stuttered, overcome with emotion.
He then looked worried. "Oh Jim, I can't take it, you need to pull it out." He was beginning to panic.
"Just relax sweetie, you'll be ok. I'm not going to make any sudden moves."
He calmed down and I began to slowly move my hand inside him, forming a fist. The waves of sensations were soon driving Ed nuts. At times he was almost babbling, he was enjoying himself so much. "Oh, fuckin hell, Ed, seeing your arse stretched around my wrist is so fuckin hot. It's so soft and beautiful inside you."
Having my hand inside him was amazing. I could sense his heart beating and felt his pulse around my wrist. The texture of the lining of his arse, was silky soft. My fingers had never felt anything quite like it before.
His dick, which had gone soft as I initially entered him, was now as hard as wood. He began stroking himself, his head rolling from side to side, as waves of sensations cascaded over this body. It didn't take long before he orgasmed again. "Oh fuck Jim, I'm going to cum," he gasped. "Go for it baby, shoot your load while my hand is up your arse."
Those words pushed him over the edge and he shot line after line of cum over his chest. Jim had never been a strong cummer, usually his cum almost dribbled out of his dick. But this time, he not only kept cumming but the force saw several shots land on his chest and one hit him on the lips, which he eagerly lapped up. "Oh man, oh fuck, oh wow," he cried, almost incomprehensibly.
When he calmed down, he realised my hand was still in his arse and he suddenly looked worried. "Don't worry, honey. Just stay relaxed and I'll slowly pull it out."
Watching his hole stretch again as I pulled out was mind blowing. "Oh man, that's amazing sight seeing your hole stretch." No sooner than it was out than I grabbed my cock and began stroking it, shooting a massive load all over Ed's chest. He greedily scooped it up and ate it all.
Exhausted, I lay down on top of him and we began to passionately kiss again. After a few minutes, I rolled off him and we lay side by side looking at each other. We were both smiling so much.
"I love you so much Jim," Ed said. "It was just so amazing, nothing has made me feel like that before. I can't wait until I get my hand inside your arse."
"Me too," I replied, although secretly I wasn't so sure. My hands were relatively small - Ed's were massive by comparison. It had been an effort to get my hand inside Ed - I couldn't imagine how his hand would ever get inside me.
But then the story of my first fist, is for another time.