Anal masturbation is the practice of stimulating the anal sphincter and prostate using your fingers or other items. As an introduction to the uninitiated, it is probably best to start with your own fingers to explore the area, get to know what it feels like on the outside, and then gradually start to penetrate the anus. Start with one finger, see how it feels. Anal masturbation can be as superficial or as deeply penetrative as you prefer.
Anal Masturbation: A Guide
Tips for Anal Masturbation
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Everything You Want to Know About Anal Sex (But Might Be Too Embarrassed to Ask)
Takeaway: Safe and pleasurable anal play is all about following a few key rules. Anal sex can be a little frightening for straight guys - at least, at first. That doesn't mean they aren't interested, though. Here we'll take a look at some of the things that might concern a hetero guy who wants to try anal play - and provides some tips on how to have the best, most mind-blowing orgasm you can ever have. But first, I want to add a note that this is an article for straight men, by a straight man.
Note: It's relatively easy to do this technique unsafely, so you must be very careful with it. We assume no liability for the technique of anal stimulation, and if you choose to perform it, do so at your own risk. Please exit if you are not interested in the idea of stimulating the anus. IF you've done a lot of reading on masturbation and orgasm — even within JackinWorld — you've probably come across references to anal stimulation.