I donā??t remember when I discovered anal play or what led me to it. I know that Iā??ve fantasized about fucking my girlfriends in the butt for a long time, and I know that Iā??ve only rarely had the pleasure, too. But I donā??t recall when or how I discovered the pleasure I get from having my own butt fucked. Iā??ve never done it with a guy, and only a very few times have I managed to get one of my female partners to fuck me with a dildo or vibrator. So most of my experiences have been with myself. But it's an absolutely regular part of my sex life with myself.
I love the feeling of having my ass filled and sometimes wear butt plugs. Iā??ve worn them while surfing the web, and Iā??ll occasionally wear them when sitting around the house, reading, or watching TV, or whatever. Not long ago, when away on a business trip, I stuck a butt plug in my ass and went for a long walk about the town I was staying in, which felt great and left me with a massive hard-on. It was a special turn-on knowing all these people walking by me had no idea what I was doing.
The main reason I like anal play now, though, is the kind of orgasm that it gives me. I used to, and probably still do, envy how women masturbate. Partly, it's because there are so many ways they can wank, but it's more because of the endless orgasms some of them manage to have. One woman I knew used to cum five or six times nearly every time we had sex, one right after the next. I used to wish like hell I could do the same thing, but my anatomy always got in the way. Until I discovered my prostate.
As far as I can remember, my earliest anal masturbation involved dildos. Dildos are for fucking, and thatā??s what I started out doing. I found out pretty fast that, if I fuck myself at the right angle, the head of the dildo will bump into my prostate. Itā??s hard to get the angle just right. If itā??s too steep, it hits too hard, which can be painful. If itā??s too shallow, it misses altogether. But when itā??s just right, it causes intense sensations deep inside my body, and it makes precum flow out of my cock like a river. Very quickly, the sensations build towards that pre-orgasmic state, and I find myself lingering there for a long time. It feels like, if I could just keep at it for long enough, or just hit the right spot, Iā??d cum just from fucking my butt. But early on, I always found myself tiring, or just getting too horny to keep at it, and Iā??d stroke myself to orgasm with the dildo in my butt. The feeling of my ass grabbing at the dildo while I cum was and is wonderful. Don't get me wrong! But I just wondered what would happen, if only I could keep at it longer. Surely, I'd cum, eventually, without having to touch my dick at all.
That was my quest: To cum, just from anal stimulation.
There was this one day (and this day I do remember, very well, having fantasized about it many times since) when I was incredibly aroused before I even got to my bed. Iā??d been surfing the Net for a while. My boxers were covered with precum. I got out my favorite dildo, lubed it up, and slid it into my butt. I got on my side and pulled my legs up, which Iā??d discovered created a good angle for getting at my prostate, and helped keep my arm from tiring. The deep, intense sensations started more quickly than usual. I remember looking down and seeing a puddle of precum growing on the sheets, which I quickly started lapping from my fingers and rubbing all over my face. I had a really intense fantasy going of my girlfriend fucking herself in the ass with the very same dildo while she masturbated. I was moaning loudly. It was so intense. I was just carried on a wave as the sensations started to rise beyond what theyā??d previously been like. And then it happened: Something like the familiar feeling of orgasm welled up slowly, and gripped me, from deep inside my butt, and I felt contractions beginning, again from deep inside me, and making their way to the tip of my cock. My whole body was just overtaken by the orgasm. I shuddered uncontrollably, and moaned loudly. It went on for a very long time, for much longer than any orgasm Iā??d ever had before. When I finally came down, I looked down at my cock, and noticed, first, that there was no cum, just a much larger puddle of precum, and, secondly, that I was still very, very hard. And I noticed, too, with great excitement, that I was experiencing no post-orgasmic lack of interest.
I basked in the glow of that amazing orgasm for a while, but then I want right back to fucking my butt. I did it slowly at first, but harder and faster as I felt the same feelings build again. It didnā??t take as long the second time for the waves to start crashing over my body. That second orgasm was probably the most intense. I remember thinking, at one point, that I had no idea how long it was going to last. It only stopped when I stopped fucking myself, and that wasn't because I wanted it to stop, but because I just couldnā??t cum so hard and move my arm at the same time. And again: No ejaculation; no loss of erection; and no satiation. I came twice more that way, before deciding it was time to ejaculate, which I did, by stroking myself the usual way. That orgasm too was unusual, because there was no ā??peakā??, no building-building-building-and-then-bam! The ejaculation came without warning. All of a sudden, I was just spurting huge amounts of cum, spraying all over the place. I hit my face, even.
So that was it: My first multiple orgasm, and Iā??d managed five in just one session. Iā??d achieved my quest, in one sense, though I still wanted to be able to ejaculate just from fucking my ass. Iā??d even found that women werenā??t the only ones who could come over and over. I was damn sure I had found nirvana.
I wasted no time trying to have more multiple orgasms, going right back at it as soon as I had some more privacy. But to my great disappointment, it wasnā??t at all like riding a bike. I thought Iā??d learned the secret and that I'd be able to repeat the experience any time I wanted. But, in fact, I was unable to have even one 'dry' orgasm again for a month or more. I eventually found that, if I could have one, I could have almost as many as I wanted. But getting that first one was hard. I tried fucking myself different ways. I tried getting myself really aroused before starting. But nothing seemed to work reliably. There was no telling what would get me started, or when or if it was going to work.
Thus began my second quest: To find a way to have multiple orgasms reliably.
The obvious thing to try was a vibrator. Iā??d toyed around with those when I was younger. I found one at the house of this woman whose kids I used to babysit, and borrowed it now and again to use on my dick. I figured that getting some of those vibrations to my prostate would feel good. So I ordered up a couple different styles: softer, dick-shaped ones and harder, but still straight, models.
All of them turned out to be useful. The soft, dick-shaped vibrators I ended up using in much the same way I had been using a dildo before. Adding the vibration definitely felt good, especially if I turned the vibrator on only after Iā??d started to feel those feelings welling up deep inside. There were times that this combination got me multiples, but it ended up not being any more reliable a method than the dildo, really.
The hard straight models I used in a different way: Instead of fucking myself with them, Iā??d just put them in my ass and set the tip of the vibrator on or alongside my prostate. That didnā??t work so well with the softer vibrators. Since theyā??re soft, and have the vibrating bit in the base, there isnā??t much vibration at the tip. But the first time I used one of the hard ones, I remember being shocked by the intensity of the sensation and thinking, ā??Oh yeah, this is going to be goodā?. And it was. I pressed it hard against my prostate, occasionally moving it in and out, or side to side. By then, I was quite experienced having multiples and could tell when things were going the right direction. But I wasnā??t prepared for what happened next. Women often speak of finding just the right spot, holding the vibe right there, and just erupting. Thatā??s how it happened that day.
I was moving the vibe around and suddenly it was on this one spot: the sensations immediately became incredibly intense. My hips rose up off the bed, and I reached down and grabbed my balls. The tension was unbearable, and then all of a sudden, my body just exploded in the most intense orgasm Iā??d ever had. Even more amazingly, since I was using the vibrator, and so didnā??t have to move my arm, and so didnā??t need to stop to rest, I was only halfway down the slope before I was on my way back up again. I mean, less than a minute had passed, and there I was cumming a second time. That second orgasm wasnā??t quite as intense as the first one, though I'll never forget the body-wrenching contractions that started way deep in my ass and just shook me all over.
I donā??t remember how many times I came that day, but it was a lot, seven or eight, before Iā??d had enough. I stroked my cock until I ejaculated, with the vibrator still buzzing away in my butt. I was so turned on that I started scooping up my cum, licking it off my hands, and rubbing it all over my face. And there was a ton of it, too. That got me so turned on that I stroked myself to another orgasm, using my ejaculate for lubrication. That one was more or a relaxing orgasm and involved only a dribble of cum. But damn. I was truly drained, and very, very satisfied.
Well, you can probably guess the next part of the story. Once again, I thought Iā??d discovered the secret, and once again I was disappointed. The hard vibrator, for sure, was able to get me off a bit more reliably than the dildos. G-spot vibrators were a bit better. But none of them were really reliable. And I still hadnā??t managed to ejaculate without touching my dick.
Fate was on my side, though. I canā??t remember what Iā??d ordered from Adam & Eve (then an adult catalog, now a web site), but with my order came a free waterproof vibrator. I didnā??t care that it was waterproof, but it had the vibrating part at the tip instead of at the base, and that meant that the vibrations at the tip were much going to be much more intense than those in any of my other butt toys. That, I figured, had to be a good thing, since it was the tip that I wanted to put on my prostate. I wasted no time finding out.
That vibrator turned out to be the best one Iā??ve had, and the first experience with it was mind-blowing. (Do you get the idea that maybe first experiences are the secret?) I came over and over and over, masturbating with that thing in my ass for two hours, though I did pause at one point to give myself a real good butt-fucking with one of my pink jelly dildos. Iā??d say that I lost count of how many orgasms I had that day, but I was so incredibly turned-on that I was totally unable to count and so never really had a count to lose.
That vibrator, though, is still not reliable at giving me multiples. Iā??d say it probably works one time in six. It did, however, help me attain my other quest, totally accidentally. One day, I was playing with it and was feeling quite tired. Iā??d been trying to get over the peak, to have that first ā??dryā?? orgasm, and start my multiples, but nothing was working. So I just decided to rest for a while. I lay back and left it buzzing in my ass. I rested there for probably five minutes, and then started mindlessly playing with my tits, pinching and squeezing them. Then I felt it start. I was already very excited, from what Iā??d been doing before, and my nipples have always been very sensitive, so playing with them was making my cock get really hard. I was about to reach down and move the vibrator back up hard against my prostate when, all of a sudden, I felt myself suddenly racing towards orgasm. I reached down and put my hands alongside my cock, touching my thighs, and was struck by an image of myself, lying on my back, as my wife fucked my ass with a strap-on. That did it. Without much warning, my cock started shaking and spewing cum all over my body. It felt great, but more satisfying was the fact that Iā??d finally done it. Iā??d finally ejaculated just from anal stimulation!
I actually can do that fairly reliably. I have to be pretty aroused before I start. I have to be very relaxed, somehow, at the same time, so I can concentrate hard upon the sensations in my ass. But, if those things are right, I can usually ejaculate just from having my golden vibrator buzz in my butt. I actually donā??t do that very often: The orgasms actually arenā??t all that great, really. But itā??s sufficiently unusual to be exciting, so I still do it every once in a while.
So that quest was completed. The other, however, would continue.