Anal masturbation allows you to discover what feels good for you and what doesn’t. It also let’s you figure out what you’d like to share with your partner before having anal sex.
Before you get started you’ll want to research the basic parts of your anal anatomy, most notably the sphincter muscles the anal canal and the prostate.
The anus is the external opening, the anal canal is the passage just inside it, and the prostate (in those assigned male at birth) is a sensitive gland a few inches in that can produce intense pleasure when stimulated—all important to understand in the context of safe and satisfying anal play.

You want to make this an enjoyable experience so it helps to dim the lights, light a candle, and play music to help you relax and help discover yourself pleasure you want to find a comfortable.
You want to find a comfortable position so that you have easy access to your anus.
Use gloves if you have any issues with cleanliness and to help protect from any nails or rough skin.
Since your anus and rectum don’t self lubricate, it’s very important to use lots of lube. Using lube helps prevent friction discomfort and tearing. If at any point you feel like it’s too dry down there make sure to add generous lube.
You don’t want to rush anal play when you’re starting out. The anal muscles need time to relax and to adapt to any touching or changes you’re putting it through. This is a time for privacy and exploration.
First you want to start outside of your anus, this means putting on a glove lubing up the fingers and massaging the area around your anus. Take the time to breathe and notice how it makes you feel. The slow breathing can help relax the muscles and allow the anus to expand, which can help with penetration.
Sometimes touching the anal region isn’t very arousing for people so it’s okay if you stimulate yourself in other ways such as masturbating with your genitals. There’s no need to rush into penetration, since the goal when starting out is to get used to the area around your anus and build comfort with it.
If you feel that you’re ready for penetration, you can gently press your finger onto the anal opening; I’m not saying to poke with the tip of your finger to enter, I’m saying to moreso tap with pressure instead. Then while staying relaxed, move your finger in small circles or on the anal opening and gently push inward. If there’s any pain you may need to try to relax more, slow down, or add more lubrication.
Since the anal opening has a lot of nerve endings you’re mostly going to have some sort of sensation of fullness when your finger enters and pressure. By entering your finger a couple of inches more inward and pressing on the front wall you can stimulate your prostate if you have one. And instead if you have a clitoris there is also an internal part of the clitoris that can be stimulated through anal play.

Overtime you’ll get comfortable with entering with one finger and there will be different ways for you to experiment. For example you can put your finger all the way in or partially, you can pull say in and out, you can also rotate your finger while it is inside.
Since your sphincter muscles can stretch it’s very possible for you to stick large toys or body parts in there. However this takes practice and you need to build up that stretch tolerance. This is why it’s smart to start with one finger and then move to 2 and then add in toys of different sizes as you gain that time and experience
After you’re done you want to make sure that you clean up. Just so you know even if you don’t see any poop that doesn’t mean that there isn’t anything there. There is bacteria so make sure you wash your hands and toys that you’ve been using, along with any surfaces you are playing on. And make sure you never go from anal play to vaginal play or you might get sick.
Under no circumstance should anal sex hurt. If if it hurts that’s a sign that you need to add more lube and slow down.
By experimenting anally by yourself you can get comfortable without the pressure of anyone else there. This allows you to explore your own pace, get more comfortable with your body, and find new ways to pleasure yourself and even others.
Here are some resources I recommend:
DOM SUB 101 teaches you essential basic and advanced BDSM concepts, such as DomSpeak, power exchange, finding a partner, poly jealousy, primal play, contracts, worksheets and so on.
Submissive Journal: 365 Daily Journal Prompts will help you develop your emotional awareness, build your kinky relationships, as well as explore your submissive self-image and sensual desires.
Danger & Play BDSM Package includes handcuffs, mouth gag, kink paddle, collar and leash, nipple clamps, blindfold, shibari rope, and much more.
Classic Black Flogger is an incredibly versatile 5-star, impact play toy for both beginners and seasoned players.
Discreet Remote Control Vibrator 3 is the funnest toy to have your partner wear for getting them hot and bothered anytime and anywhere. (Read review)
Rose 2-in-1 Vibrator is easily one of the most pleasurable experiences she’s looking to have. (Read reviews)
Low Temp Wax Play Candles are incredible for very intimate, sensual experience that you and your partner will never forget. (Read guide)
The links above are NOT affiliate links. The product links are the exact same products I happily own from trusted vendor Sinful Goods.
Bathmate Hydromax is the safest and most effective male enhancement product I’ve ever used to increase my length and girth. Read more here.
Relationship Subliminal for self-hypnotism will help you change your unconscious behavior, gain better relationships, and attract like-minded people and partners.
DOM SUB 101 (Lite) is an affordable alternative to the ever-growing DOM SUB 101. This is for curious kinksters who are on a budget.
Inner Shadow Work is my main website that goes over psychology, spirituality, emotional maturity, consciousness, etc. If you’re interested, click here.