Chapter 3: Who owns this hole?
I am writing this chapter several months down the line - a point in time where I have passed any reasonable threshold of normality. My hole is no longer my own - and certainly no longer resembles a regular asshole at all; having been transformed in its purpose and shape to a true man-cunt.
When I left you last, I had finally succumbed to a deep, dark longing that I'd harbored for many years. I'd found the courage to tell Timo that I wanted him to fist me and with that I'd admitted to myself that I wanted my asshole to become a fuck-hole for men to use. It was a massive step for me, and over the course of the week leading up to our date second thoughts crept in, but I knew with each evening that passed - and with almost nightly sessions of plugging my hole with the large cone - that the desire would only grow inside me. So when the weekend came around, I was disappointed that Timo seemed to have cooled on the idea of our meeting.
I messaged him several times, only to receive one work replies or none at all. When finally, I asked him to confirm our hook-up; he told me he was busy and we should try to get together another time. I felt gutted. I spent the whole week fixated on it and now...nothing. I presumed that the journey had been cut short pre-maturely; but in reality it was soon to take a much more intense turn.
I needed to clear my head and grabbed a book and decided to go sit at a caf‚ close by. The weather was stunning, and it was the perfect time to be outside. I passed a few places on my street, but all seemed too full with people brunching. Finally I came across a small gay bar, but that opened during the day for coffee. No one was around, so I ordered and sat on the chairs out front to read and do some people watching to kill the rest of the morning. The server had barely brought out my coffee and left me alone with my book, when I caught the familiar silhouette of Timo walking down the path. "SHIT", I thought to myself, he was looking right in my direction, so no chance for me to escape.
I felt a strange anxiousness as he approached and I forced a smile as he drew close enough to greet me.
"Hi, how are you?" Timo asked brightly, seemingly unbothered by the uncomfortable meeting. I feigned some small talk, and claimed I was waiting for a friend to join me. I had felt so anxious, I hadn't even really noticed that Timo was walking the down the street accompanied by another man. He introduced him and I immediately noticed the intense starring of this companion.
"This is Keith! An old, American friend of mine...", Timo said, and I smiled and nodded a greeting towards the tall friend who said nothing, but continued his unflinching stare.
He was tall. I had thought Timo was well-built, but this guy was even bigger. A tall, bulky, light-skinned, Black guy. I glanced up towards him and caught his eyes again. He starred me right in the eyes and refused to look away. I felt awkward and wished them both a nice day, as finally they continued on walking down the street.
"WOW, that was awkward," I thought to myself. I was relieved that it was over, took a sip of my coffee and opened my book. I began reading, but the image of this man starring me in the eyes so intensely would not leave my head. After some moments, I settled into the first chapter and let my imagine sink into the story. Ten, twenty minutes passed, I wasn't sure, but I gradually became aware once again of the same unnerving feeling of being watched. I looked up to a fright. There was Keith, standing a few feet away, watching me intently. His eye contact strong and unflinching once again.
"So your friend never came," he stated at length. I hesitated, still in a little bit of shock and unable to come up with an excuse fast enough. Without an invitation, he walked forward and came to sit beside me at the table. His stare continuing to lock right to my eye line. I was at a loss for words. Sheepishly, I stole glances in his direction as I sat silently waiting to see how the situation would evolve. His oversize frame commanded over the table and one of his large fist and arm rested causally on the table, with the other rubbing his massive thigh. My eyes followed the slow stroking movement, to stare directly into his crotch at a large bulge that protruded obscenely. Again, when I looked at his eyes were piercing into me and he grinned - his presence had a unnerving control over me.
"Timo tells me you want to be fisted," Keith's accusation left me winded and beaming red with embarrassment and evidently he read the shock on my face. "I knew it as soon as I saw you anyway," he smirked again, " don't be embarrassed - it'll be our secret." I was at a total loss; I couldn't bring myself to say anything. Firstly I couldn't really believe that Timo had said anything - something so private that I would never have dared to say to anyone. Yet, the knowledge being out there, was somehow liberating; to suddenly be able to talk freely about such deeply held thoughts felt almost like a relief.
"He shouldn't have told you that," I eventually managed to say. "I told him that in confidence."
"Ha! - you obviously don't know Timo!" Keith smirked again, but with a warmness that made me begin to relax and ease my embarrassment. "Don't worry, boy, no judgement here. And like I said - I knew it even before he told me." He continued, finally breaking his intense gaze, to call the server to order a drink.
"You couldn't have known it - I'd never even done it," I challenged him. Intrigued by this man who oozed a level of confidence that bordered closely on arrogance. It could have come off as rude, but something about the way he carried himself - it was impressive and appealing.
"Well, maybe not that you were a fistee, but I could definitely tell that you were submissive. You have submissive energy. You're open to penetration but alpha males. You let my eyes penetrate you and you said nothing. And then Timo confirmed it." Keith was chatting like we were having a lunch date; nothing out of ordinary. "All Timo cares about is that goddamn 'giving birth' fantasy he has, then he loses interest. I'm in it for the long term. I want to really help boys realize their potential."
"And what is that?" I asked, part anxious and part afraid to hear his response.
"Oh, well that all depends," he said, smiling broadly. "It depends on you."
We sat chatting together for the next half an hour; our conversation roaming widely between banality and personally intrusive interrogation. When I was at ease, he would knock me for six with a question that plumbed the depths of my deepest sexual fantasy. Somehow I felt totally at ease to share things that I may not have even admitted privately to myself.
"What is the largest dildo you own?" Keith fired at me, in the midst of a tangent on favorite films.
"I have a plug that I use - it's 8 inches in circumference; I've been trying to wear it daily." Saying this all out loud, in the midst of a 'regular' conversation; I had a feeling that it was normalizing what I felt previously had been in some way illicit.
"God boy!" Keith grinned and patted me on the shoulder. It felt good. "8 inches is not enormous - I guess just shy of a can of Coke, and nowhere near the girth of my fist....," he said, his gaze penetrating my eyes once again, "...but it's a good start." He finished his drink, and we sat for a moment longer, before he ordered me to take his number down in my phone; I did it without hesitation.
"Note this down," his command continued, "One relatively small plug for daily wear. One large dildo - super long, but thin - for depth training, and an inflatable dildo to gradually open you up wider and wider." I hesitated a moment before opening my notes app and typing down what he said. "That'll probably set you back about 100 or 150 euro, when can you get it?" he asked looking at me expectantly.
I opened my mouth; I wanted to question what he was saying, but his self-assured commands and expectant look were controlling my thoughts. There was no space for me to doubt him or explain that he had mistaken me for somebody else, someone who belonged in this world he was describing. It was as if he was making the decision for me - for us - and he had decided my consent for me.
"I...I can pick the stuff up this afternoon," I finally blurted out and he only nodded in agreement, not the least bit surprised at my submission to his command.
"Good, then we'll keep in touch later this evening," he declared before standing up and walking away from the table. I was speechless.
Over the next few hours, I ran the encounter over and over in my head - no matter how much I tried I couldn't get this man's presence out of my mind. He was older than any other man I had been with - and yet I had been instantly attracted to him. That he was handsome and in such great shape was initially what I though had attracted my stare, but I gradually came to the conclusion that it was his penetrating energy. Just like he has explained, his alpha-male presence had been instantly intoxicating, and it continued to linger in my head. Each time a doubt or hesitation entered my thoughts, I could hear his commanding , but calm, low voice assuring me that I had to prepare myself as he desired. Later the afternoon, I found myself once again stood before the glass cabinet in the Sex Shop with the intimidating sex toys displayed like kitchen appliances.
I felt strangely detached from what I was purchasing - the struggle was gone from the situation, as I had been provided a list by Keith that removed any ambiguity or shame. I felt nearly like I was buying the toys for someone else and so was not in any way ashamed when asking in the store for what I needed. Upon unpacking at home, I excitedly sent a photo of my haul to Keith.
What lay before me on my bed was an array of sex toys of different shapes and sizes. I picked up the long silicone slinky that appeared larger and overbearing now that I had it home. I pumped up the inflatable dildo and realized it's girth matched that of my old butt-plug when deflated. I checked my phone, but still no response. As I waited, it began to dawn on my that these objects were much larger than anything I had ever envisaged even in my deepest jerk-off fantasies. Doubt slowly began creeping into my mind.
Beep! Beep! - My phone sounded and brought me right back to the present.
- Perfect, boy!
I was relieved again, and felt a unfamiliar sense of achievement from his validation.
- You have three months to train. I'll be in the States.
Train? I thought to myself. I had imagined meeting Keith and spending evenings together, slowly introducing these toys in to an otherwise vanilla sex date. I realized now this was far from what he had in mind.
- I'm spending the summer in Houston, so you'll have to do daily check-ins...with photos! :)
His instructions continued. - Use the plug daily, build it up to 2 hours wear. For the other two; by the end of this month I want you to have taken them both inside. Fully.
The messages, the tone, the way he didn't wait for a reply; it turned me on and I could feel my cock tingly as I stood reading my phone screen.
- Start tonight.
The last message read, and I wanted to start it right away. I set about setting up a corner in my small studio, where I had space beside a cabinet to store everything I needed and could set up a camera and move around easily.
First up was the inflatable dildo. I had always been more fascinated by girth than length, so I was extremely turned on by the idea of having a 'cock' inside me that grew in girth. It was 22cm long and already thick before I'd started to dilate it. I out on some music, lay down on a towel and took the poppers in my hand. At length, I was able to take the whole dildo into my hole - after all, I had always enjoyed well-hung men.
Once inside I let it sit for before sliding in and out and growing accustomed to the girthy dildo in my hole. My boy-pussy was much more welcoming than ever before - after a few weeks spend using the butt-plug I'd previously considered enormous. I sniggered to myself at the thought of that now. Nonetheless, it had helped me to learn to relax my sphincters and get used to the initial burning sensation of pushing a foreign object into my man cavern - knowing know that the stinging would soon subside as my sphincter adjusted to its new wide, resting position.
I was able to take the whole length of the dildo in record time. In less than 10 minutes, I was lay - hand-free - enjoying the feeling of fullness I sought out almost every evening. I reached down and took the dildo's air-cushion pump into my hand and squeezed once. The stinging was immediate, as the dildo inflated by what in reality was only a small amount, yet felt inside my anus like a doubling in size. I waited another 5 minutes for the feeling to subside. I took a hit on the poppers and waited. Finally I gained the courage to squeeze the pump again. "AAAhhhh," I wailed involuntarily as the pain shot through my sphincter as it was forced open wider again. I lay still paralyzed in agony, hoping that time would assuage the pain.
A long time passed before I finally felt able to concentrate and although in discomfort still I could move around and try to appreciate the new sensation emanating from my colon. I decided that I had had enough; I would take a photo and call it a night. I reached for my phone, snapped and selfie and sent it to Keith.
- It's in!
Proof that I had followed through on his command. I lay back exhausted, contemplating how I would get this out. Then almost immediately I heard: Beep! Beep!
- SO hot! Do 5 pumps to progress.
I read the message, a little despondent. An anxiousness impressed on my feeling of achievement, and I suddenly felt that this was something I perhaps had not thought through fully.
- Your hole will be amazing when you push it out!!
I read Keith's second message and the encouragement shook me out of the nervous regret that was simmering below the surface. I tried not to reflect on it too much, reached down for the hand-pump and squeezed hard twice in quick succession.
"ARRRGHHHHH," the moan I let out surprised me, but the white, shooting agony that shot down my legs was momentarily unbearable and I couldn't hold the sound inside. Never in my life had I felt such intensity; I cursed myself for not taking any poppers, and immediately reached over for them. The relief they gave me was soothing, and I longed for the feeling of my sphincter closing on itself and the stinging to dissipate.
One More! - I told myself and took another hit on the poppers. I squeezed one final time; "FIVE!" I shouted to stop myself screaming in agony, as my asshole stretched open wider than ever before. I lay still in shock - absorbing the brand new sensations that were flowing through my body. An agony coupled with a feeling of pleasure and fulfillment that I had never experienced before.
I took a final hit on the poppers and waited. When the daze was deep and the pain had given away to fullness, I pushed as hard as I could and felt the dildo budge - a small amount at first and then like the flood gates opening, it shot at speed out of my anus; leaving my sphincter gaping open and messy. I reached down and felt it with my fingers. I felt soft, warm and inviting - and loose of course. I lay exhausted, savoring the moment, before the creeping feeling re-entered my mind that I wanted to experience that sweet sensation again.
"Five more pumps and then I'm done!" I told myself, before reaching for the poppers to start over.
Over the next three months, I was in regular - almost daily - contact with Keith. Sometimes, a short message of encouragement or even a single word reminder was enough to keep me on track, other times - if I hadn't send any new photos - a call to get me back on track was required. Over the summer, despite the distance, we got to know each other well.
I was comfortable in the dynamic that we had established, and I felt a kind of safety that I had a certain control. I was progressing according to Keith's schedule, yet somehow I felt that I had ultimate decision about how fast I would proceed - I'd convinced myself that at any moment I could withdraw or change the pace - yet in reality he had me completely wrapped around his finger.
As the summer drew to a close, my routine had become fixed; whatever I did during the day, the evening was always on my mind, knowing that I would be coming home to 'train' and only the weekends were mine to enjoy the city and do whatever I wanted. When it came though, the weekend was never the relief I though it would be, and I longed to back under the tutorship of Keith - receiving his instructions for hat evening's training session. The thoughtless of those sessions and the trust I placed in someone else allowed me a kind of disassociation from the quotidian that was refreshing.
We were 2 and half months in, and I was able to easily take the large inflatable dildo inside me with minimal preparation. I no longer really paid attention to the number of pumps, but rather to the sensation of dilation that it gave me when I pumped it larger. My hole had progressed significantly. Keith had given me extra tasks of wearing the plug throughout the day - to go shopping, walks in the park - and I found great pleasure in doing it. I had struggled more with the depth, but Keith assured me that this was something we would work on together.
I was sending him a nightly update of my progress when he informed me that he was soon back in town. His reply read:
- So are you ready to take my fist this weekend?
Despite all the time we had interreacted and how open I felt I could be with him, I felt a nervousness in my stomach knowing that we would soon be meeting again for real. I brushed the feeling aside:
- Can't wait to feel you inside me!
I decided to clock off for the night, and the following few nights and feeling of unease overwhelmed me when I tried to train, as the reality dawned that I would really be giving the control of my hole away. Up until that moment, even though Keith had been commanding me - I still had ultimate control; that was about to change.
I agreed to go to Keith's that weekend, and we made a date for Saturday at 10. I spend the day worrying what I would eat, fretting that I wouldn't be clean - so I spend an unusual amount of time preparing for the evening that afternoon. When the time finally rolled around I was feeling tired and decided to have a vodka and coke before leaving the house as some Dutch courage.
When I came to Keith's place, it was exactly only half how I imagined it. I'd expected a sling with red lighting - right out of a porn film; but it was warm and comfortable. He invited me in, and we chatted for some time, about the summer; his trip to the states, my time in Berlin and he generally put me at ease. He had asked me to wear the plug and I was acutely aware that he wielded this control over me as we chatted. In every way it was a normal evening, yet he had commanded and taken control over my sphincter since before I even left my house.
"Are you ready to take my fist then?" his question popped out of the blue as they had a habit of doing. "Let's have a drink...", he stood up and walked into the adjoining dining area and bar across the open space apartment.
"Strip down to your jock-strap!," he yelled as he exited the kitchen with two tumbler glasses. He had choreographed the entire evening; right down to the underwear I was wearing.
As I stripped down, I heard the clinking and clacking of glassing and ice-cubes. He walked over and handed me a drink just as I was folding my clothes on to the side next to the couch.
"Here, it's gin," he said and handed me my drink. I felt much more nervous than I had anticipated, and the feeling encouraged me to drink it down with usual speed. We sat and continued to chat as Keith sipped on his own drink, and I gradually began to loosen up.
I felt a giddiness almost immediately and handed him back the empty glass; a restlessness was washing over my body and I stood to take off my jockstrap. Although I was accustomed to the plug, I was suddenly aware of it pushing inside me; I wanted to show Keith the progress I had made. A rare inhibition lead me to bend over in front of him and pull the plug from my clasped sphincter, revealing a pink, loose and wet manhole.
"Wow, the Gee was good, right?" Keith laughed.
"The Gee?" I asked confused.
"Yeah, the Gee you drank, I told you," he replied, seemingly unconcerned.
"I thought, you said Gin?" I asked, confused yet somehow quite unconcerned too.
"Yeah Gin with some GHD, I wanted to help you relax, I want you to enjoy tonight." He said and gestured towards the bedroom. I was almost instantly in a daze as Keith then lead me by the shoulders towards the bedroom. I allowed him to guide me without resistance. No more words were spoken as he guided me into the position he wanted me.
As we entered the bedroom, he had clearly prepared the space for the night to come. The mattress had been covered in a rubber sheet and a small table beside the bed held everything he required for a night of fisting; gloves, j-lube, poppers. Along the wall there was also an array of dildos, much larger than anything I was accustomed too. Along the back wall, there stood a large tripod with a camera mounted on it and professional lights set up - although turned off.
My mind was quickly beginning to spin. I wanted to question him about the GHB he had put in my drink, but there was so much going on in the moment, that I was barely able to digest where I was. Keeping a grasp of the reality that I was familiar with was hard enough. I rubbed my face with my hands; "I am here with Keith to be fisted", I told myself as a way to calm the rising feeling of unease. It had the opposite effect, I felt anxious and worried; I began to back out.
"Where are you going? Don't worry, it'll be fine," Keith reassured me - he put his heavy hands on to my shoulders and pushed me steadily towards the bead. As we walked, I could feel the familiar buzz of the GHB hitting my system. I was light-headed, and each step was more difficult than the last, but before long I was at the bed and I immediately slumped forward onto it. The rubbery smell of the black sheet instantly filled my nostrils. My mind was swirling, but I felt Keith's hands roughly moving me into place.
I was on my hands and knees with my feet comfortably resting on the edge of the mattress. I felt Keith's strong palm and my back followed by a swift push forcing my head down onto the mattress. In only a jockstrap, my ass stuck up high in the air and my slightly wet hole was exposed and vulnerable. I focused now on the openness of my anus; it felt open from the plug Keith had ordered me to wear that I had removed only moments before and relaxed thanks to the GHB which continued to send my mind a flight.
I lay still, waiting patiently for instruction from Keith, but any time he expected something from me, he would reach over and force me into the position he desired. I was completely at his mercy; he didn't ask for my position or expect anything less than for me to allow him to position me as he wished. My head span and in my mind's eye I thought about my open asshole - waiting for it to be penetrated. Without thinking, my hands reached back and placed on each cheek, I pulled open my hole and moaned loudly in anticipation. I could think about nothing else than feeling my wide open hole filled up.
"Oh yeah? You want this fist in that pussy, huh?" Keith's low voice asked, as a techno beat began to fill my ears. "Hmmm yeah, this pussy-hole is never gonna be the same again..." I heard Keith muttering behind me.
Some more time passed, and I heard Keith rustling around behind me; my eyes were closed and still buzzing, until finally I felt lube being spread around my asshole. It was cold, and before I had time to adjust to the feeling I felt my asshole open up to the familiar feeling of my butt-plug. In an instant though, the plug was pulled free from my hole, and only a moment later it penetrated me anew. I moaned loudly with each fresh penetration; my hole barely having time to close up again before Keith pushed the plug deep into my sloppy hole again. At first the pace was slow and regular, but I could feel that it was gradually gaining speed and force. Eventually, Keith pulled out the plug and it didn't immediately re-enter me; but I felt a new sensation, something soft at the entrance to my colon. His fingers and thumb were rubbing up against my anus. Jabbing softly but firmly until the width of the knuckles became too wide for my sphincter to stretch too.
This jabbing went on for some time, with Keith turning his had gently when it reached the maximum stretch. My hole was relaxed and my mind was barely able to follow what was happening but I felt a resistance building as my sphincter was pushed further than it had ever been before. Slowly but surely the burning pain of my sphincter stretching overcame the drugs and I involuntarily cried out.
"OK, OK, you're ready...", Keith assured me, reaching over and pulling me up by the shoulder. I immediately felt the wooziness in my head and was only just able to stay up right on my knees without support. Keith reached across again, and this time held a bottle of poppers up to my nostril.
"Breathe in!" he ordered, and I did automatically; I'd grown accustomed to using poppers almost every day over the past few months of my 'training'. The bottle moved to my other nostril and he demanded I take another hit. "Hold it in!" He said, pushing me back down into position with my hole hopelessly exposed again.
"OK, let it out," he ordered, and I immediately felt his clenched fingers and thumb jab again at my loose anus opening. Keith's other hand was placed firmly on my back, holding my tightly in place. The beat of the music filled my head, and I felt I had lost grip of reality. I was aware only of a pressure building at the entrance to my back passage. The only part of my body that had any meaning was my open sphincter - the pressure building steadily. I could feel my breathing growing deeper and then a sudden push forward a brief shock ran through me from my anus and I could feel a deep moan as Keith forced his fist relentlessly further into my anus. Then I felt it; his knuckles penetrated past my sphincter and I felt a momentary relief, yet he kept going further. The intensity was incredible and I squeezed my sphincter tightly closed, but it immediately met the resistance of his lower hand.
"Almost there...", Keith groaned, and with a final push his fist fully entered my rectum and my sphincter finally closed around his fist. He held still for a moment, while I adjusted to the feeling of my lower rectum being filled up like never before. The pause was only momentary though, and he slowly began an ever-so-slight, yet unbelievably intense rocking motion. Within seconds, waves of the most intense sensations were pulsing through my lower colon. It was too much for me.
"Argggghhhh..pull it out!" I moaned, unable to stop myself. I could feel an orgasm building. I hadn't even noticed that my little dick was stiff as a rock in my jockstrap and then - just as I was on the verge of shooting a load - Keith pulled his hand free of my anus and let me sphincter relax a moment.
"Ohh shiiit!" were the only words I could muster, "I almost shot my load!"
"FUCK, boy! You just took your first fist!" Keith was elated. Yet after only a moment I felt his hand return to the entrance of my rectum, and seconds later he pushed himself back inside me and then withdrew again immediately. He settled into this pace, turning my boy pussy into a punching bag; going just deep enough to bring me to the edge of orgasm before pulling out, and punching back in again.
The sensation was like a long, intense orgasm that lasted on and on. It the most intense thing I had ever experienced. I couldn't stop myself from moaning, stopping only long enough to ask for the poppers which were swiftly thrust into my hand. I took a long hard hit and re-assumed my position with my sloppy, fist tunnel wide open in the air. Keith took the chance as I was no totally out of it. Colors and music swirled in my mind as I was brought time and again to the verge of cumming; his fist punching hard into me time after time.
I have no idea how long this had been going on for, but at length I gradually began to come around again to the reality and to glimpse loosely what was happening. Keith was now violently and relentlessly ramming his fist deep into my hole; I had no idea how deep, but it was several inches past his wrist. The intense sensation was finally beginning to give way to pain and yet still he punched my asshole.
"Wait...pull out!" I managed to gasp, as I drew the strength to force myself forward flat onto the bed and away from his invading fist.
I lay spent on the mattress, as Keith rubbed and patted me encouragingly telling me how amazing I had been doing. I hadn't even cum and yet it had been the most intensely orgasmic feeling of my life. I was exhausted and it took me several moments to come back down to reality. Finally, I cautiously reached my hands back and touched gently at my asshole. I slid my fingers in and was amazed to discover that there was no resistance at all. I dared to add my thumb and was shocked that my hole hand - certainly much narrower than Keith's - easily slipped inside my anus. My hole was looser than any hole I had ever felt before. I felt Keith keel beside me, his head draw close to mine.
"Your hole is a cunt now...and it's mine!" he whispered cruelly into my ear, and stood up off the bed.
"Let's take a break," he declared loudly, "that Gee won't wear off 'til morning, we have hours ahead of us yet."
I'm not sure I could comprehend what was in store for me that night, at that moment. For the time being, I pulled my hand out of my rectum and rested it against my now gaping sphincter which no longer even tried to close over. I savored the feeling of having had my boy-pussy turned into a cunt for the first time, and most definitely not the last.