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How I Turned My Asshole Into A Cunt

by Orangebinder
21 Oct 2025


I came out a few weeks after starting college and then discovered, to my surprise, that I was a hungry bottom. I couldn’t get fucked enough. I wanted it all the time. It was an itch that could only be scratched one way. Along the way, I discovered that most guys my age, including myself, had tiny little round assholes clamped shut really really tight. But, older guys often had looser assholes that often came to look more like vertical slits. I grew to love those cunt-looking assholes more and more and became determined that I was going to have that as soon as possible. While I loved my asshole (and getting fucked), it was sometimes a real job getting a dick into my hole. My hole was very effective in keeping things out. Loosening up and relaxing took far too long, particularly when it was a quick hook-up in a public toilet or a park at night. Problem was, I wanted things to enter (over and over and over). I didn’t know if looser ass cunts came with age or only after being fucked a few hundred times. But, I did see some younger guys in porn videos with ass cunts so I figured that it was matter of use, not of age. That meant I didn’t have to wait forever to get one. I could make it happen. I talked to a few older guys about it and they did their best to talk me out of it. They longed to have the tight assholes of their youth back again and assured me that a looser hole would come in good time whether I wanted it or not. When I was adamant, I finally got a couple of them to suggest that I start training with a butt plug because I could leave it in for long periods of time, unlike a dildo. They both suggested that I go easy and slow. If anything hurt, stop. But, with time and patience, all things would stretch. I was so thankful to them, I let them fuck my really tight eighteen-year-old ass long and hard. After dumping their loads in my butt, I sucked them dry as well. When I got home, I ordered a set of four butt plugs from Amazon in graduated sizes. I wasn’t so concerned about length, it was the width that would stretch me that I wanted. I was so excited the day they arrived in the mail, I shot my load while trying to open the package without even touching myself. I had to stop for a moment while I dumped my cum into my shorts. The narrowest plug was only three-quarters of an inch wide at the base, which may not sound like much but when it has been in for a few hours, it starts to feel like a tree trunk. I lubed up, finger fucked myself a few times, and managed to get the butt plug in place. My asshole clamped down tight around the base of the plug and I knew it wasn’t going anywhere. I pulled up my pants and went about my business for the day. I left it in for four hours, then it took it out for two, then back in for another four hours, and on and on. I did notice that within a couple of days, I could insert the narrow plug more easily and quickly than it did the first time. I wore it every day under my clothes, even while I slept. Much to my surprise, wet dreams started to return. I hadn’t had one in a number of years at that point but it must have been the raking against my prostate every time I turned over in my sleep that caused the wet dreams to come back. The dreams were always about getting fucked by monster dicks. The plug became a regular part of getting dressed. When I went to any of the campus tearooms for sex, I would take it out. Otherwise, I consistently followed the four in, two out rule during the day and then left it in all night while I slept. By the end of the first month, the narrowest plug easily slipped in and out. When I could easily fuck myself with it like a dildo, I decided it was time to move on to the next larger size. It took some work getting it in, just like the smallest one had taken a month earlier. I followed the same procedure with the second plug. It wasn’t just thicker but also a bit longer. That meant while I sat in class, it reached farther into my asshole and every time I shifted my weight or moved in my seat, it would push against my prostate more than the smaller one had. I had a near constant hard-on. I had to start leaving my shirt untucked in front or I had to carry my books in front of me to hide my hard dick. This effect only got worse with the later plugs. While it took about a month to stretch my hole enough that the first dildo could easily slide in and out without any impediment, it took about four and a half months to get the same results with the second plug. But, it eventually happened and I could fuck myself, in and out, in and out, with the second plug. It was then time to move on to the third plug. One thing I discovered was that if I laid off the stretching for even twenty-four hours, my hole would shrink to pretty close to my original tightness. I made it a point to never go without a plug, even while home on break or vacation. The third plug was in place for nearly a year before it had done all the stretching it could. When I laid down on my back in front of a mirror and raised my legs up over my chest, I liked what I saw. My tight round hole was turning into a looser vertical slit. My asshole was turning into a mancunt. I still wasn’t where I wanted to be but I was clearly on the right path. It made me all the more determined to keep going. I had one more plug to go, the fourth one was one and a half inches in diameter at the base and four inches at its widest point, something unthinkable when I started. To help the process along, I bought an elephant dick dildo that was conical. From the point at the top, it broadened out to five inches at the base. It looked like a small traffic cone and I fucked myself on it for at least thirty minutes every night. I would use the suction cup on the bottom to attach it to the linoleum floor in the bathroom and then pound myself on it, bouncing up and down until I couldn’t take it any more and I would shoot like a fucking lunatic. It was only after several months of consistent work that I managed to get all the way down to the base but I couldn’t hold it there for long. When I got off the dildo, I could easily slip my fourth plug into my butt like melted butter and my asshole would gently close in around it. After eight hours of sleep with the plug in place, I was ready for another day of stretch-training (and getting fucked). It took about another year to master the fourth plug and I only managed it that quickly because of the supplementary stretching I did nightly with the elephant dick dildo. When I started I couldn’t believe that I would ever easily take the fourth plug, now I wanted something bigger. I bought one more butt plug, this one was two and a quarter inches in diameter at its base, where my sphincter would clamp around it. It felt so big but so good when I slipped it in. It felt like it should be there. For the first couple of weeks, I could only managed an hour or two before it had to come out. After that I could go the full four hours of my routine. By the time I graduated from college, I loved what my asshole had become. I had made it my own. When I laid on my back in front of a mirror and raise up my legs, what I saw was a vertical slit with ever so slightly swollen lips on both sides. For all the world, it looks like a cunt, my very own pussy, my man twat, not that I’ve ever seen one in person. I got hard just looking at it. It wasn’t until I entered graduate school that I first got fisted and I took to it like a duck to water. I am convinced that regular fisting made that stretching permanent and even built on what I had already done. I love it now that a guy can line up his dick and just push in, no more fighting and lubing and prying me open. My asshole is now as welcoming to dicks as I’ve always wanted it to be. It is now so much easier to get fucked in a bathroom, a rest stop, or a park. I don’t have to carry around a bottle of lube anymore. I see my wrecked cunt as a real accomplishment, a badge of honor, proof of my dedication to being a fully committed bottom. I love it and couldn’t be happier. Orangebinder@yahoo.com

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