If you’re attempting to reach anal orgasm by having your (or your partner’s) fingers inside your ass, you should ensure that your fingernails are trimmed and clean. The last thing you want is dirty/pointy fingernails inside the rectum, as this can cause tears and uncomfortable feelings.
Also, if you’re not used to it, reaching around inside an ass can be a little strange. For this reason, some people prefer to use a glove or condom as a barrier between the finger and the prostate, helping it to feel a little less weird and direct.
As always with anal play, make sure that your finger is adequately lubed up with a high-quality anal lube. Everyone likes different lubes, but water-based and silicone-based lubes tend to be the most recommended for anal play.
If using a prostate toy
If you’re using a reputable prostate toy brand such as Aneros, then the prostate massager toy is going to be shaped so that it ergonomically fits your body, making it easier to insert and feeling quite “natural” once it takes its place.
First, be sure to clean the sex toy with warm soapy water or specialized sex toy wipes before use. Before putting something in your ass, ask yourself “would I be willing the put this in my mouth?” If the answer is no, then you need to clean it. Never put something dirty or dusty inside your bottom.
Next, put a towel down on the bed and lay down. Lube the prostate massager up with plenty of water-based lube before insertion. You may want to “warm your anus up” by lubricating your finger and fingering yourself for a few minutes with 1 or 2 fingers. This helps your anus to relax and expand slightly, making more room for the toy.
Getting into the “zone” for prostate play
It’s called a “prostate massage” for a reason – you really need to be in a relaxed and meditative state of mind. I know saying that you need to be in a meditative state sounds all hippie-ish and weird, but believe me when I say that it’s true! Calm your body and your mind, think arousing thoughts, and get yourself excited for one of the best orgasms of your fucking life.
This meditative state of mind helps to trigger and stimulate the muscles inside you which are going to give you intense pleasure later on. It’s very hard to describe if you’re not used to these sensations, but it’s almost like you have to get your butt “excited” for this pleasure before it evens happens. The more “excited” your ass is, the more readily it produces anal orgasms.
Also, breathing is really important with many kinds of prostate massage – make sure that you take deep and long breaths, allowing your body to feel all the sensations of the massage as you slowly inhale and exhale your breath. Try to be as mindful as possible with your breathing; it’s an essential part of the process. Practicing mindfulness meditation in your everyday life could actually be a huge help here.
Hands free prostate orgasms are not the sort of things that can be achieved in a quick 10 minutes before you catch the train – this is the kind of thing you need to set a couple of hours aside for. Ideally, you want to be home alone (you’ll want to moan loudly) and you’ll want to have 1-2 hours of time without any distractions. If you can plan for 2+ hours of free time, then that’s even better. Don’t rush, as rushing will get you nowhere with this kind of erotic milking.