My fascination with anal play started back (probably freshman year) when I discovered that pushing my perineum while I was whacking off could increase pleasure and even stop ejaculation to make resuming easier. It also aids in holding back the orgasm as a whole to continue whacking (or sex or whatever) with nearly no break. From there, I did some studying to find that, among other things, the prostate was really sensitive and could lead to a different kind of orgasm. I think I found that out in tandem with seeing the prostate milking scene in the movie Road Trip. Since then, I had been thinking of trying it.
Of course, being a straight guy, I had reservations about trying such a thing. It wasn't so much the thought that I might be seen as gay or that I had images in my head of a penis ramming my poop shoot, but rather that I would have something put up my butt rather than come out of it. Coincidentally (and maybe luckily), the first thing I ever tried was a toothbrush. This particular toothbrush had a handle that was long enough and angled just so as to hit the prostate pretty much dead on. The picture below shows the contours (of a similar brush, not the exact same one!) As you can see, the end is tapered and very anal-friendly, then it widens , then tapers, then widens again. The good leverage and positioning were the lucky parts. The part that might have been unfortunate is that something like that could easily and painfully get lost up a beginner's bum. I'm lucky I had a good hand on it.
The method to get it up there was simple. Cover it in a soft plastic baggie and hold the end of the baggie, cover the tip of this apparatus in vaseline, the slowly work it in there. I was 18 or so and had read of the dangers of unlubed objects probing nether regions, so I was prepared. I kind of held the bristled part and leveraged the handle against my prostate again and again. I had pretty hard wood, as this was experimental and new, so I cam quickly. That was my first and only prostatic orgasm. I never touched my cock, and I remember coming hard.
Afterward, I was pretty disgusted by the shit smell and all I really remember is finding a way to dispose of it without my parents finding it. Flash forward to my junior year of college. I shared a room in a house with a friend, and I had ordered a discreet package containing a purple vibrator which a website said was great for men to hit their prostate. You can see from the picture that that's a crock of shit, since the prostate is located in a man similar to the G spot in a woman. (Face the recipient, insert a finger and make a "come hither" gesture.) Also, the toy could easily get sucked inside a colon if the user didn't have a grip. The vibrator only worked to get me turned on while I was masturbating, but not to give me a prostatic orgasm.
I also tried putting on a glove and using my fingers, but the angle just doesn't work for me unless I'm squatting. Fuck that. If I felt more comfortable with my girlfriend, I'd ask her to try it on me, but we're not to that point. We talk frankly about sex, but I've never told anyone about this, so it might be further down the line.
Anyway, to solve the problem, I did some research and found out what works well. A good anal toy needs to be four inches or so and bendy to hit the prostate. Enter what seems to be the most popular "prostate massager": the Aneros. It looks really funky, as it has three parts. The insertable portion (vertical and top), the perineal-stimulator (horizontal left side) and the handle.
The best thing about it is that it uses anal sphincter contractions to power the toy so it strokes the prostate. It's hands-free and it won't slip out (or in)! I had to try this thing, and with a little graduation money, I decided to splurge.
In addition to the Aneros, I got some cock rings (upon a suggestion by my girlfriend, who knows nothing of this particular purchase but said it would make stuff more fun), a masturbation sleeve (since I've always wanted one) and an anal doucher. The anal douche is just a bulb with a tip, but as I said before, I hate the smell of shit. I read that this is how most people do anal sex or rimming without worrying about it... though I think if I ever rimmed a girl, I might have to use a dental dam or spray her down myself.
I'm excited for all of this and will have to detail a play-by-play as it all pans out. While I was looking, I found a trial by a guy in a nearly similar situation as myself. He writes as if he' doing a chemistry lab write-up. That kicks ass!
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