Any Guys/girls Tried Anal Masturbation?

A few things:

1) Everyone is bi-curious. It's also just known as "being curious."

2) Anal masturbation or sex-play with a partner has nothing to do with sexual orientation. Starting when I was 15 and long before I was into hooking up with men or people of other genders who have a penis, I was playing with my anus in a couple different ways while masturbating. And it wasn't a foreshadowing of anything because I still am decidedly on the straight side of the spectrum. It just feels damn good.

3) Even after I'd been fooling around with male friends here and there, I asked my first serious girlfriend to use her dildo on me and it was very much a sex act between and for two straight people having straight sex.

4) I'm putting this in a list just because it was easier to type it out this way. It's not meant to be pedantic or clever or make fun of you at all. I swear. I think it's great that you want to experiment with different ways to seek pleasure from your own body. And, you know what? Maybe you are bi? I don't know. I just wanted to dispel the idea that anal play is inherently homosexual.

5) Anal vibrators feel fucking fantastic! Just start with one that fits. I got one called The Bump. Or Bump? Wasn't very expensive and with lube meant for anal penetration, it shouldn't be too uncomfortable for a novice as long as you take... it... slow... And if it hurts. Stop. But that should come much later. Just start with one or two fingers properly lubed. I started out in the shower while my hands and butt were all soapy. Works perfectly. Then started putting vibrators against my butthole but not in. That also feels amazing.

 

Anal toys are amazing! I love big anal beads.

 

There are several prostate vibrators on the market that are relatively small and easy to insert (check Amazon). I like Lube Life Anal Lubricant; it's thicker and lasts longer. Take a shit first; you want your rectum as empty as possible. Use lots of lube, and insert slowly; take all the time you need. Your anus has two sphincters; inner and outer; for me, the inner one takes a while. It may take several minutes for your body to relax enough to open up (when it lets you in you'll know!). Keep up a tolerable pressure, and breathe; looong exhales; this'll help relax your pelvic floor. I generally don't start stroking until I'm fully inside. Be gentle with yourself; you don't want your body to come to associate butt-fucking with pain, or it won't want to play.
For full-size dildos, it helps me immensely to have a partner insert and fuck me with it.

 

As a man, I love anal masturbation. I can't believe how much pleasure my well cleaned asshole can bring me. I first started with a hard plastic vibrator in my 30s, but soon switched to pliable rubber dildos, still relatively stiff but bendable. The hard plastic didn't work for me because it would hit the walls of my anal canal (rectum), without any give, and hurt me. But the dildos can bend. First I started with a relatively small and thin dildo, with barely a head on it. But eventually I migrated to more realistic looking cock dildos, and for the last 10 years or so, a nice thick 8 inch cock.

My preference always has been to squat over the dildo, holding it in one hand, and lowering my asshole on top of it, bouncing my ass up and down on top of it, rather than using it to fuck myself missionary style. For lube I initially for the first few years just used my saliva, lots and lots and lots of saliva. But the problem with that is that it always dries out quickly and you have to apply more. But eventually I used anal lube that I bought in the local sex shop. Anal specific lube seems to be better because it doesn't dry up as quickly and has extra lubrication qualities.

So you would start rubbing your hands sensually all over your naked body and your bum cheeks, and finally teasing around your asshole opening. Touch your opening, and rub around it, getting to know its textures and the feeling that rubbing brings you. Put a little saliva on the tip of a finger and see how that feels rubbing against your opening, around and around your tight asshole opening. And then see what it's like to slip the tip of your finger a little bit into the centre of your opening, a little bit inside. Add more saliva to your finger tip and push a little bit more of it into you're opening. This is the opening to your anal canal, to your wonderful rectum, a beautiful part of your body, one that can bring you a lot of pleasure, maybe even more than your cock. Gradually push more and more of that saliva drenched finger into your opening, deeper and deeper. Begin to pull it out and in, in and out. Then try with two fingers, going nice and slow, with lots and lots of saliva, gradually getting your asshole opening used to the feeling of something penetrating it, eventually the incredible pleasure of something penetrating it. Begin to fuck yourself with first that one saliva-drenched finger, and then the two fingers, fingerfucking yourself to not only open and prepare your hole for the dildo, but also because of the amazing pleasure it gives you. Then, my friend, you are ready for the real thing.

Cover your dildo in the anal lube and begin to very slowly push the head of the dildo past your outer and then inner asshole sphincters, really focussing on relaxing your asshole as much as possible. Go very slowly and allow your sphincters to very naturally open around the head of the dildo. Eventually the whole cockhead gets past the inner sphincter and then it's easy-going the rest of the way in, until it is all the way deep inside you, and then you can begin to fuck yourself with it, pulling it almost to all the way out, and then pushing it deep inside of your asshole, up and down.

I don't know why I only more recently in the last few years finally got a dildo with a suction cup so I don't have to hold it, but can fasten it to my bedroom door (for doggy style fucking). Unfortunately my bedroom hardwood floor, bathroom floor tiles, and kitchen linoleum, are all surfaces that just aren't flat enough to make the suction work--it's unfortunate because I prefer being on top, fucking the cock, bouncing up and down on it, for reasons I'll explain below. But oh my gosh, the suction cup is so much better than having to tire out my hands and wrists, and struggle with my super slippery hands (covered in saliva or lube), trying to fuck my asshole with regular dildos. Even if I want to fuck my ass on top as is my preference, or in missionary style, lying flat on my back with my legs bent and knees to my chest or splayed out, I can still have a good grip on the suction cup part at the bottom to pound my ass with the cockhead and shaft part of the dildo.

The reason I love being on top is because I can maneuver my ass while fucking myself, while lowering my anal canal over the dildo, and raising it up, thus fucking the dildo while holding it still under me (dildo not moving), with only my body moving up and down on top of it, in such a way that I can get the head of that dildo to push against my prostate inside my asshole. This is the great advantage of being a guy, that wonderful male G spot--P spot--inside our ass. I definitely discovered my wonderful male prostate while fucking my dildos, and it was like nothing you can imagine. The feeling of pressing that dildo against your prostate is indescribable pleasure. I have been actually able to give myself prostate orgasms many times throughout my life, with a kind of cum that is more watery you could say, shooting out of my cock, hands-free, without ever having to masturbate my cock, just pure anal masturbation, pure prostate masturbation, with pleasure that just can't be described. And you can make yourself cum this way multiple times in one session. It is fucking amazing.

The rest of this post is the gay part if you want to skip it:

Like others have said, it definitely doesn't have to be, but for me, anal masturbation is always playing to the ever growing gay side of myself. So I always start out using lots of saliva to lube up by asshole opening, pretending it is a guy rimming my asshole. After sucking my dildo cock (imagining it was another guy's real cock of course), and after using first one saliva-drenched finger, and then two fingers, fingerfucking myself to not only open and prepare my hole, but also because of the amazing pleasure it gives me (of course imagining it's another guy fingering me), I would then cover my dildo in anal lube and begin to very slowly push the head of the dildo past my outer and then inner asshole sphincters, really focussing on relaxing my asshole as much as possible (pretending it was another man slowing and lovingly penetrating me with his real cock). Eventually the whole cockhead gets past the inner sphincter and then it's easy-going the rest of the way in, all the way deep inside me, and then I could begin to fuck myself with it (imagining it's another man fucking me, making love to me, and eventually pounding my ass).

I'm still a bottom virgin, having only fucked guys as the top so far, but I can't wait to have another man take my ass and make it his, to have another man's real cock pounding my asshole to oblivion, and finally breeding my ass, giving me his cum seed essence to become one with me. I can barely imagine how much greater a real man and his real cock will feel fucking my ass than my dildos have been for me the last 30 years. I don't know why it's taking me so long to replace the dildo with a real cock. But I guess I shouldn't be surprised: it took 21 years of sucking hundreds of cocks before I finally inserted my cock into another man's asshole and fucked him, the greatest sexual experience of my life and that changed everything for me. But I don't think it's very much longer now before my asshole fulfils its true destiny. I now absolutely know that not only was I born gay, destined to be a lover of men, but my asshole was born to have cocks inside of it, making love to it. I can't wait for that day when I have finally graduated from anal masturbation to anal intercourse with another man as his bottom fuck boy.

 

That’s a hot story