Since I still get asked a lot on how to do it, I’ll try to sum it up quickly for you guys 🙂
DISCLAIMER: I am not a doctor and I realize that not everybody is built the same. What works for me does not necessarily have to work for you. I also realize that there’s a difference between milking your prostate and having an anal orgasm.
Short explanation: Milking feels nice and ends with ejaculation while an anal orgasm explodes inside your body and doesn’t always mean you eject semen.
Chastity. You don’t need a device to lock your penis away (even though I think it’s fucking awesome). But you shouldn’t jerk off for at least 10 days if it’s your first time. That’ll help, also when you’re having moral doubts for whatever reason.
Hygiene. Give yourself an enema and make sure that you’re really clean. And make sure that ass is completely hairless. Objects entering your anus will pull on your hair down there and it will not feel nice.
Choose the right weapon. For me, a realistic dildo works the best. And it’s shape is very important. See this picture?
The parts that I circled is the most important ones and are going to rub against your prostate. That’s right. Don’t poke your prostate like you’re trying to stab it. Firmly scrape against it with that part of the glans instead. Forget about your own penis. Don’t even touch it. I mean it. Only one cock matters right now and it’s not the one attached to your body.
Relax. There is absolutely no need to hurry. You don’t have any other place to go right now. It’s very important that you explore your ass gently with lots of lube until penetration does not feel uncomfortable at all. Fuck yourself for a while and don’t think about how much time already passed. Watch some anal porn while you’re at it and try to visualize how you might cum from getting fucked in the ass. Remember that awesome sex is mostly happening in your brain.
The right position. I have no explanation for this. But when I started with regular anal masturbation, doggy style worked the best for me to cum from getting fucked. But every person is different.
Don’t be a lazy fuck. Some people play with their asses for hours and expect a miracle to happen. That’s the wrong idea, in my opinion. You gotta work that cock. Like this:
Well I realize that this little animation might look a bit silly. But that’s actually what I usually do. While my sphincter stays mostly relaxed during my fuck sessions, I flex the inner part of my ass against the cock that’s pounding it.
Practice. It took me over a year to learn this. And when I first fucked the cum out of my balls anally I was playing with myself for more than an hour. But today it only takes me a few minutes, when I’m in the right mood. Don’t get discouraged if it doesn’t seem to work. Give your ass a few days rest and try again. And remember that no part of this should ever hurt. If it hurts you’re doing it wrong and you should stop before you injure yourself. Seriously.
Good luck and happy assturbating!