Message: Anal Masturbation Advice
Anonymous: I have recently started trying to masturbate anally (using fingers). Some tips on what to do in order to make it more pleasurable, and also how to widen the anus?
When many people start experimenting with anal play, they encounter the problem of having anything inserted into their anus making them feel like they need to go to the bathroom. This is a problem solved by two things, primarily: practice, and association of anal stimulation with other pleasurable things to make your body realize that things in your butt can be there for pleasure too.
While there are many people who masturbate or have sex anally with no other stimulation and get pleasure from that, it’s important to build up that association with other forms of pleasure, so you should masturbate in a manner known to bring yourself to orgasm (whether it be manually or with a vibrator) while also masturbating anally with your fingers or a toy. Experiment with different ways of doing this—some people get increased pleasure during orgasm just with the presence of something in their ass while others prefer to have it moving around or in and out in their ass during orgasm. The key is to regularly try to give yourself orgasms while masturbating anally at the same time. You should do this as much as possible.
To increase the size you can fit, you should insert whatever size you can currently comfortably fit and masturbate with that for a few minutes before carefully trying to insert something a little bit larger. If you can fit one finger, increase to two. If it hurts, don’t just push it in anyway—push it to the point where it hurts and then back off and push again, repeating until the pain at that point isn’t there any more and you can insert further. Pain tells you you’re stretching things too quickly and need to warm it up more first before continuing.
Consider also getting a butt plug which you can wear for extended periods of time during the day, while masturbating, or during other forms of sex. This helps train your anal muscles to have more control over tightness and looseness, helps get you used to the feeling of something inside, and just feels good.