This story is the latest in the saga of Jim and Ed and their exploration of fisting. In my last story I outlined the fun Jim had when he inserted a big black bell (globe) eggplant in his hole – repeatedly. This story picks up from where the previous episode left off and leads up to their first anniversary of Ed taking a fist.
While the last story had more than a grain of truth to it, this one is largely fictitious and draws inspiration from amateur porn that was on xtube before it was deleted in the recent purge. I hope you enjoy the story and I'd appreciate your feedback. 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.
When Ed got home from his business trip, I explained what I had got up to with the eggplant on the weekend before. He just about creamed his pants. That night, as he rode up and down on my small fist, he urged me to describe in detail the sensation of the eggplant entering my hole for the first time. He wanted to hear more of how my hole crowned as it left my hole for the first time. He loved hearing of how it stretched my hole so wide. He panted like a dog when I described how my hole would go POP, POP, POP as the big black vegetable went in and out. When I revealed my secret desire to have a man cunt, he shot a massive creamy load.
Even so, he wasn't sated. He was so turned on by what I told him, he turned me over and ate out my hole like a man dying of thirst. He was able to reach depths no tongue had ever gone before. He teased at the beautiful folds, fucking my hole with his tongue.
"Oh Jim, I love your man cunt. It's so beautiful and soft." When I pushed back and my hole pouted and winked at him, he became so turned on that he was as hard as a rock again. As he fucked my brains out with his thick 7-inch uncut dick, he repeatedly trashed talked my hole.
"Oh wow, it slips in so easy, just like a fuckin pussy. You love that big dick in your man cunt, don't you?"
"Yeah, fuck my sloppy pussy you big stud. Breed my slutty hole," I replied.
"You want my babies in your cunt, do you?"
"Yes, give them to me. I love being fucked by a stud who knows how to take a fist," I replied. That turned him on even more, and he began pile driving my hole. After the longest fuck I could remember we both came in copious quantities. The splattering of cum from my dick, Ed's cum oozing from my hole, as well as Ed's first load – not to mention the Boy Butter seeping from his fisted hole – meant we had to change the sheets on the bed they were such a mess.
Later that night as we scissor cuddled (on fresh linen) before falling asleep, Ed whispered in my ear about just how turned on he had been by my admission of wanting a man cunt. He reached between my legs and gently caressed my puffy hole: "Hmmm, so soft, so beautiful – I love your man cunt." But as he fell asleep, in that moment between the conscious and the subconscious, he also made a telling confession, he whispered in my ear: "You're so lucky – I wish I had one."
As I lay there, my lover asleep with the middle finger of his right hand in my twitching hole, I pondered how I would make his wish come true. It was then that I realised our fisting anniversary was only a few weeks away. As I also drifted off to sleep, I wondered how I would give Ed exactly what he so secretly desired.
The next morning, I checked my diary, and worked out that our first-year fist anniversary was two weeks hence on a Friday. I began to hatch my plan. I manoeuvred my schedule so I would be away on the Thursday night before and set the plan in action. I knew Ed's routine well and that with me away he tended to sleep in a little longer. But not this Friday – at 7am, he was rudely awakened by a courier ringing the doorbell.
After signing for the package, he blearily opened the box to find brief instructions for the day ahead.
"Dearest Ed – on this, the anniversary of you first taking a fist, the gods have heard your deepest desire and are prepared to grant this wish but only if you really want it fulfilled. If you really want a man cunt and to stretch your limits, clean out your hole and insert the enclosed plug to be worn all day. To signal your agreement, you are to put on the enclosed chastity device and leave the key on the bench – if it is there, I will know you want to proceed. On getting home, clean out again, eat a couple of the special brownies you'll find in cupboard on your return, put on the enclosed leather jock strap and I'll expect you relaxed in the sling about 7pm. Your loving master man cunt, Jim."
Inside the box was a Gapekeeper 75 from Topped Toys. The 75 is 2.4 inches in diameter at the maximum – smaller than my hands but enough to ensure Ed was partially loosened up for the night ahead. Given the size of Ed's cock, out of deference I had left him a larger chastity cage, but it would still be a tight fit if he got excited.
I arrived back in town about mid-afternoon and as it was a Friday, after dropping some stuff off at the office and a quick catch up with my manager, I headed home. The chastity key was on the bench so I knew Ed was up for what I had in store – although he had little idea of my plans. I baked some marijuana brownies (possession of small quantities are not illegal where we live) which I knew would also help mellow Ed for what I had in store. I left a couple on the bench for him to eat when he got home. I also set up the sling in the spare bedroom, and made up a batch of xlube and then put it in the fridge. I then cleaned out my hole and, as it was getting near the time Ed would be home, I went to the nearby aquatic centre for a swim. I could have a shower there and surreptitiously change into some hot leather gear I'd bought which I'd wear under some loose sweat pants and sweat shirt on the way home.
When I pulled up outside the house, apart from the porch light, only the light in the spare bedroom was on so Ed was obviously in position. I quietly entered the house through the back door into the kitchen. I pulled off my sweat shirt and dropped the sweat pants. I thought I looked pretty hot – I had been working out a bit lately so my body was more toned. I was wearing a leather harness that framed my pecs, a leather jock strap and black boots with white socks. I looked over at the bench – Ed had eaten the brownies; he was going to be so relaxed. He'd left a whiskey on the rocks for me – the ice was only just starting to melt; it had recently been poured.
I picked up my drink, supping on the taste and walked to our makeshift dungeon. I smiled on entering – Ed was wearing almost the same gear. He was so hot. He'd also been hitting the gym a lot lately and had developed some serious muscles, particularly his pecs and biceps.
The room had a sensual feel. Instead of the main overhead light – there were two lamps, each with red bulbs for mood lighting, and some house music playing with a strong beat.
"Hey boy," I said in my deepest voice, "Ready for your wishes to come true?"
"Yes, Sir," he replied, almost sheepishly.
"Tell me what you want boy," I said again, supping again on my whiskey before putting it on a side table, where the lube and poppers were waiting.
He ummed and ahhed, and I moved forward, strongly grabbed his chin with my right hand, and again repeated more forcefully: "Tell me what you want boy – spell it out."
"I want a man cunt," he half whispered.
"What boy? Speak up, let it out," I demanded.
"I want a man cunt, Sir," he said more forcefully.
"Good boy," I said and I leant in and we passionately kissed.
"Good boy," I said again, as my left hand wandered down to his crotch. I squeezed the jock strap and could feel his encased cock. We kissed again.
"Good boy," I said again, as my hand ventured further and felt the end of the plug in his arse. I tapped the base and I ran my fingers around the edge of the plug – feeling the tender flesh which would be soon transformed. We kissed again.
"Are you ready boy?"
"Yes, sir," he responded more forcefully.
"Well then, let us begin." I then moved between Ed's suspended legs and sat down on a stool. I supped on my whiskey again and admired Ed's hole. While the Gapekeeper 75 has a maximum diameter of 2.4 inches, the neck was 1.4 inches in diameter meaning Ed's hole had been permanently at the width of an average cock all day.
I began teasing his hole by gently pulling the plug out just a little and letting it slide back in a fucking motion. Ed immediately began to groan. And each time the plug got closer to the widest point, he groaned some more until it popped right out and before Ed could react, I pushed it back in.
"Oh fuck, oh fuck, oh fuck," he repeated as the plug went in and out.
"You like that boy?"
"Oh, yes Sir, I love it – give me more."
What he didn't know was that the Gapekeeper 75 wasn't the only plug I had bought from Topped Toys. I also had a Chute 85 which, while it is only a little wider at maximum diameter, also allows a cock to inserted as well.
"You wanted more and that's what you're going to get. I'm going to use this on you boy – are you up for it?" I said waving the plug at him.
"Yes, Sir, but can I make a request?"
I nodded in agreement. "Can I ask that my first plug goes in your hole? It seems only fitting that we share the love, if that's ok with you Sir?"
I smiled. "What a good idea boy." I pulled out the plug from Ed's hole, added a little lube and slide it almost effortlessly into my man cunt. "Hmmm, it's so warm. You must have a hot hole boy."
"Thank you, Sir," Ed responded. "But please plug me again. I don't want my pussy-to-be to get tight again," he said in a subservient tone which he was clearly enjoying using. But before pushing the bigger plug into Ed's hole, I finished my whiskey and then I filled up a syringe with xlube and inserted it into Ed's willing hole. I then repeated the action, before smearing the Chute with Boy Butter and gently pushing it into Ed's hole. It went in surprisingly easily, Ed let out a big sigh as the plug slipped in and he enjoyed its wider girth. I repeated the fucking motion I had used with the Gatekeeper. It was clear that Ed was getting off on the sensation.
"Oh yeah, Sir, fuck my hole. It's what my boi-pussy needs sooo much," he said, affecting again his new subservient voice.
The whole scenario was turning me on big time. With a plug in my own hole, my cock was as hard as a rock. Now was the time to test out the Chute 85's extra capabilities, which I hadn't made clear to Ed when I inserted it. I stood up and leant forward and kissed Ed, but unbeknown to him, I also positioned my six-inch cock into the entrance.
At first, he looked a little puzzled as he felt my cock pushing at the entrance to his stretched hole.
"What the?" he asked before both the realisation and sensation hit him. "Oh fuck. Oh man alive. I can't believe it" before "OH FUCK!" when I pushed all the way in and then pulled back and pushed back in.
"FUCK, FUCK, OH MY GOD, what are you doing?" he said.
"You said, you wanted a boi-pussy – this is how you get one boy. Get ready for the ride of your life."
It was at this point that Ed took his first hit of poppers and the initial hesitation quickly evaporated.
"Oh yeah Sir. Fuck me, fuck my cunt. Give it to me."
And give it to him I did, fucking his hole relentlessly, with each thrust of my cock adding to the stretch from the plug until, after what seemed an eternity, I felt the inevitable sensation of an orgasm. The tightness around my cock, combined with the plug in my own arse, resulted in one of my biggest cum dumps ever. When I finally pulled out of Ed's hole, cum ran out of the chute which was still holding his hole open.
I had a sit for a minute to recover and Ed asked: "Now that you've cum, can I take off the cage and cum too Sir?"
"No boy. Just because I've cum doesn't mean this process is over. We're only halfway there."
Ed eyes widened at the thought of his hole getting stretched further and affected his subservient voice again: "Oh Sir, please be gentle on my man hole. What are you planning Sir?"
"You'll find out soon enough, boy," I responded as I gently teased the Chute 85 out of Ed's now very open hole. "But I think you need a little break – I'm going to clean you out." And with that I put my mouth to his hole and began slurping out my own cum and the lube in his hole. Ed went wild as my tongue dug into this hole and he responded by pushing back, forcing the cum out.
"Oh Sir, that feels so fucking hot. Yeah, eat my man hole – go deep, go deep." I can only imagine the ecstasy Ed felt as my tongue circled around his pink stretched hole and then dived in, but feeling on my tongue of the soft folds of his hole were exquisite.
After several minutes of eating Ed's hole, I leant back: "Enough of break time – now let's get serious."
"Yes, Sir," Ed responded enthusiastically. "What's next?"
I gave Ed's hole three syringes-full of xlube this time and then lathered up my hands with Boy Butter and I began to push more of it into his hole. Ed's hole now easily took three fingers and then a fourth on my right hand. Given my hands are relatively small – and Ed's experience in taking my fist – it wasn't long before I was adding my thumb to the mix. Ed took the cue and took a huff of poppers and soon after my fist slipped inside and he let out the biggest sigh. His face beamed with the biggest fist smile – that delightful satisfaction of having a fist in your hole.
I easily moved my fist around in his hole, letting it get used to the stretch, before I slowly removed it and pushed the left-hand in. The day with the plug in had certainly worked its magic – I had never known Ed's hole this loose. I pulled the left out to the fingers, and then added the fingers from the right into a prayer position and then pulled them apart, stretching him further.
"Oh yeah, Sir, stretch my hole, get me big and wide," Ed begged as I did this again.
I pulled the left out and the right went back in – again, so seamlessly – and I repeated the motion several more times, alternating hands before springing on him the final act I had planned.
"You are so loose boy; I think we need to ramp it up a notch. I'm going to give you 50 punches."
"Fifty," he exclaimed.
"Nah, 100."
And before he could protest any more, I began counting. I started slowly, alternating hands in and out of Ed's hole. He took a long hit of poppers and held it in.
He exhaled at 10 and his reticence quickly disappeared.
"Oh man alive Sir, that feels so fucking good, fuck my hole."
When we reached 20, I asked if he wanted it faster.
"Yes, fuck Sir, faster, give it to me."
And I gradually began to pick up the pace.
At 30, he took another huff of poppers and his hole stopped closing as I continued on.
At 40, I stopped counting aloud and when, several punches on, Ed urged me to keep counting, I went back to 40 again.
When I hit 50, the halfway point, Ed's hole was becoming so pliable, I stopped coning my hands – pushing in fist first.
"OH FUCK, OH FUCK," Ed exclaimed. "Keep fucking me Sir, keep fucking me."
Going fist first only slowed the pace for a moment. But only for a moment. The numbers kept rolling on as 60, 70 and 80 passed.
When we hit 90, I urged Ed to count with me.
"91, 92, 93, 94, 95, 96, 97, 98 and 100."
"One hundred punches," Ed shouted. "Fucking yeah."
But I didn't stop. "You're not ready to stop, you want more" as I kept punching his hole.
Finally, Ed called a halt, but not until I had reached about 120, leaving just my left fist resting inside him.
"Oh boy, you should see your hole. It is so open, so deliciously beautiful."
"Do I have a man cunt now Sir?"
"Almost boy, we're almost there – take another hit of poppers and close your eyes and picture in your mind's eye what I'm doing."
With my right hand I grabbed more lube, pulled my left-hand half out and used it to pour heaps of xlube into Ed's hole. I then lubed up my right hand with the copious quantities of lube leaking from Ed's hole and then gently pushed it up against the other hand which was only half in. Gently, but forcefully, I began pushing my right fingers into the palm of my left hand which was now back in Ed's hole.
With each push, I got further and further in. Ed knew what I was doing now and took another big hit of poppers. As I reached the point where my right knuckles were at Ed's sphincter, he got worried.
"Sir, I don't think I can take it. Please Sir, I think you should take it out."
He wiggled in the sling a little and with that, my right hand just slipped into Ed's hole – he was taking a double fist.
`FUCKING YEAH, OH FUCK, FUCK, OH FUCKING HELL," he shouted.
"Ten seconds in," I responded and without moving my hands, I counted up to 10. "Do you want them in or out."
"Out Sir, please."
And with that I pulled them both out, with Ed firing off several more expletives. He soon asked for an update on the state of his hole.
I wiped my left hand and then his hole. I then used hand mirror so Ed could see what we had wrought. There in the mirror Ed saw the gaping hole, red and puffy that was his new man cunt and he gave another big sex smile.
"Oh Sir, thank you so much for giving me a man cunt. And thank you for continuing despite my hesitation."
I put the mirror down and moved around the sling and give him a big sloppy kiss. "Anything for my man."
And as we passionately kissed, my left hand wandered back into Ed's now totally pliant hole and I gave him a gentle dreamy fisting.
"Can I cum now Sir? My cock is aching in the cage."
Ed lifted his arse and pulled off the jock strap revealing his caged cock. It wasn't hard – there wasn't room for that – but I was struggling under confinement. I unlocked the cage and Ed immediately began wanking his cock which quickly reached became thick and swollen.
"Sir, to celebrate my new man cunt, can you punch out a load for me?"
"Anything for my man," I said as I returned to the seat, lubed up my hands some more and again began punching Ed's hole.
His new hole was so damn fine and so damn loose that after 20 punches I again pushed both hands into Ed's hole and this time, they both slipped in, and out, and then back in again.
"Yeah, double punch my cunt," Ed cried and with that he began to cum like a fire hydrant, spewing his thick white cream everywhere.
When he finally stopped cumming, his cum covered fingers explored his new hole we kissed again. "Happy fist anniversary baby."
I hope you enjoyed this story. I appreciate your feedback at: ff1234@windowslive.com