First of all
No. Playing with your butt doesn’t make you gay. This seems to be the thing stopping most men from playing with their prostates. It stopped me, and trust me when I say: I regret not starting years ago, I was missing out.
You might also be wondering why it’s possible to have multiple orgasms. The reason is that when you masturbate regularly and you have an orgasm, you also ejaculate. Ejaculation is followed by the refractory period, where it is “physiologically impossible for a man to have additional orgasms”. However, when you have orgasms via prostate stimulation you don’t ejaculate and therefore there is no refractory period, and you can keep going. To give you an idea, I’ve had orgasms that are 10 seconds apart from each other.

Second of all
I find it that a lot of this requires the right state of mind. I need to relax in order to be able to really get into it. I’ve had my prostate toys in (I’ll get to the toys below) for literally an hour, and if I’m not in the right mood, nothing happens. In contrast, I’ve had orgasms less than 5 minutes in when I’m really into it. The most important thing for me is being home alone, so I don’t have to worry about making noise, and also knowing I’ll be home alone for enough time and I won’t be interrupted half way. I shut off my phone and dim the lights. This might seem ridiculous, and trust me, I would’ve thought so as well. When I masturbate regularly, I can just go whenever, wherever. I can do it in 3 minutes or 30. It’s not science. This, on the other hand, is more difficult. So all these things help.

Experience Overview
You will need at least one hour. My “sessions” usually last between 2 and 3 hours, and include well over 30 orgasms. It’s an intense experience. I find the first orgasm to be key. Once the first orgasm comes, the rest will flow very naturally. I have session peaks where I have non-stop orgasms (e.g. 10 orgasms in 10 minutes), and then I’ll have valleys where I don’t have orgasms (e.g. maybe also 10 minutes). However, even the orgasm-less valleys are amazing. They’re just pure pleasure. The most important tip I can give is don’t touch your dick. Trust me, it will be extremely tempting, and it will feel way better than usual when you do. But if you touch your dick, you get a regular (yet much more intense than usual) orgasm, with ejaculation. So you blew it (hehe), you won’t want to continue and you’ve missed out on the experience.

Equipment (i.e. toys and fingers)
I’ve used 4 prostate toys on myself, as well as my fingers. I’ll only mention and assess two of the toys I use, since the other two aren’t worth it. Aneros brand toys are very popular, but I have no experience with them. I’ll gladly add info here about this or any other if someone provides the info.

Lube!!! This is the most important thing, and you can’t have too much of it. If your toy isn’t silicone, you can use silicone based lube. Otherwise, you’re fine with water based. I always use Astroglide (water based). The only other water based lube I’ve used is KY, and Astroglide lasts way longer before it gets absorbed.

Fingers: I’ve given myself great orgasms using my fingers. However, I’ve only been successful if I’m at a session peak (as I mention in “experience overview” above). If I try to give myself an orgasm from zero using my fingers, I will fail. Not only will I not get an orgasm, I probably won’t even enjoy it that much. From what I understand, this is not uncommon. I will suggest two ways of going at it. The first is the one I see more commonly recommended. Lie on your side, with your bottom leg straight and the top leg bent so that your knee comes close to your chest. Similar tothis (if someone has a better image, please provide it). You can then reach from behind using your top hand and either use your thumb, or your index and/or middle fingers. Personally, I don’t find this position very useful, because my arm quickly gets tired/cramped and I can’t keep going. The second position, which is the one I use, is sitting on my knees, and reaching from the front using one or many fingers. Similar to this, this or this. Regardless of which of all position you use you only need to put your fingers in about two phalanges in. Once inside, bend your fingers towards your front (i.e. point to your belly button). You should feel it there. It’s softer than everything else. You can press it, or you can massage it similar to how you would massage a g-spot on a girl (use the “come here” motion). Usually a combination of both works great.

Vibrating toys: I usually start my sessions with a vibrating toy. The best thing about vibrating toys, in my opinion, is that you just slide them in and forget about them. Hands free. Once I put it in and turn it on, I try to enjoy every sensation. Really try to start getting into it. The orgasm doesn’t matter, just the current sensations. I squeeze my butt a bit, and that changes where and how the toy puts pressure in my prostate. I squeeze it a lot, and it changes again. I quickly squeeze and unsqueeze, and I’m basically fingering myself. Or I can just do nothing. Try experimenting with that to find what you like and go with that. Another great thing about these is that unlike using manual toys or your fingers, you have no control over the speed, intensity. This means that if you’re nearing the orgasm and you, for some reason, want to lower the intensity, you can’t. This produces super hard orgasms for me. Also, while I’m having an orgasm, it doesn’t stop, which makes the orgasms even harder. This also helps me have consecutive orgasms. Sometimes, I’m trying to catch my breath after an intense orgasm, and the next one comes so I cant, and then the next one comes and so on. It can be very intense. But it’s greatest strength is also it’s weakness. Since you can’t control the speed, sometimes you just want to go faster or harder, and you can’t. But the manual toys are just for that! In case you’re interested, I use the Nexus Revo 2. It’s a bit pricey, but I’d pay twice what I did knowing the experiences it’s given me. The best two features are that it has a head that spins, on top of the vibration, to further massage the prostate. It’s fucking magic. It also has a battery that lasts for extremely long (I’ve used it for 3 hours with no problem. It’s supposed to last for more than 4, IIRC). There’s nothing more frustrating than batteries dying out half way through.

Manual toys: (i.e. dildos) These are also great. You will find different shapes, girths and flexibility. I use the NJoy Pure Wand. Again, it’s a bit pricey but worth every penny. It is stainless steel, so it’s very hard and heavy, which makes it extremely easy to manipulate. It has a perfect curve, so it’s extremely comfortable to use. No weird angles for stroking it in and out. What I love about this one is that as opposed to the vibrators, I have full control over these. You can achieve orgasm by lightly massaging the prostate, or intensely stroking it, or just applying pressure to it. I’ll get into more technique below. The disadvantages about these is that you will get tired and it’s difficult to keep the intensity to the max when you’re having orgasms that make your whole body shake. But they’re not terrible haha.

Preparation
I have a routine before I even get started. I will poop one hour before I intend to start my session. Really try to clear yourself out. Then, 15 minutes before my session starts I’ll take a quick shower. I’ll pay special attention to my butthole, which should be left sparkling clean. I take the opportunity to be extra meticulous and maybe even start turning myself on by massaging it a bit. After this, I’m ready to get started. Another thing I do, which may or may not work for you, is smoke weed. I know not everyone is into that, and that it might not have the same effect on every one, but I find it that it is extremely easy for me to relax and to focus on only what I’m doing when I’ve smoked. So take that as you will.

First session ever
Get ready for “bad” news: you might not have an orgasm on your first try. That’s fine. I had a prostate toy for about 2 years. I used it on and off and I didn’t have an orgasm from it until recently. I realize now that the main problem is that the batteries would constantly die on me, but even when they held up, I didn’t have an orgasm. One thing that was always for sure: huge orgasm when I finally masturbated. Also, lots and lots of semen. I found it amazing to masturbate while the toy was in. So as I’ve said before, just focus on the current sensations. It might be a while until you have an orgasm, but I promise you’ll enjoy it and improve your orgasms regardless, so you’re already winning.

First prostate orgasm ever
As I said above, you might not have an orgasm on your first try, but after you have the first orgasm, it will be easier to get the next, since you’ll know exactly what to do. Your mind will be blown away by how amazing and much more intense this orgasm is. The first time I had a prostate orgasm, it wasn’t until about 10 seconds after the orgasm that I realized I had had one. It was so intense and so different, I was too into it to even realize what was going on. I’ll say that in a different way: the orgasm was so intense, I couldn’t even process anything else, including that I was having an orgasm. It sound ridiculous, but the orgasms can be ridiculously intense.

Cruise Control
After the first orgasm, I usually go into cruise control; they just keep coming without me doing much. And they keep coming for, quite literally, hours. I can’t even keep count in a session. I don’t even care to keep count.

Finishing up
No session is complete without a normal jerk-off at the end. I will sometimes go with my hand and sometimes use a fleshlight. Either way, it will be AMAZING. Sometimes I can last 10-15 minutes, and sometimes I can’t even last 1 because it’s so intense. Both are different but great in their own ways. Get ready to cleanup, because the amount of cum that will come out is unbelievable.

The most important part: technique
How to find your prostate: If you have a hands free toy then you’re pretty much set. Just put it in and everything will align itself perfectly. If you use your fingers or a manual toy, then it shouldn’t be hard to find your prostate. It’s about 2 inches inside your rectum. If you’re using your fingers, point them towards your belly button and you will feel it. It’s soft and round.

How to stimulate it: Vibration works great for me. You can also massage it up and down (if you’re using your fingers doing the “come here” motion) or in different patterns like sideways or circularly. I also find that with manual toys I can just shake them very hard to make them “vibrate” and it feels great. Lastly, just by putting pressure on it works.

Positions: I find that varying the position I’m in greatly improves the experience. Whenever orgasm frequency or intensity starts declining, I just switch positions and it’s like a fresh start. Here are a few positions I recommend: ass up face down, on all 4s (the “wrong one” actually works great as well), I don’t know what you call this one, on back knees up, on back knees to chest, feet to the sky (usually against a wall). I can keep going. Standing up straight, standing up bent forward, squatting, laying on your stomach. Pretty much everything I can think of I’ve tried and it has worked.

Bonus: Perineum and asshole orgasms I’ve managed a few times to give myself orgasms by just rubbing my Perineum and asshole (externally) with my Pure Wand. It only works after I’m already very worked up, and usually just one per session.

Keeping the toys in I had some trouble keeping my vibrator in at first. I would sometimes contract everything so hard during an orgasm that I would push it out. Holding it in distracted me so I needed a solution. I just use a belt that I wrap around my waist and make sure it hold the toy in. I usually need to adjust it when I change positions since the angle changes.

Credit to Multiple_o