Message: Really Want To Try Anal, How Should I Prepare?
Anonymous: Hello! I really wanna do anal, but I’m a anal virgin. I have a vibrator and occasionally play with my ass. What training can I do?
Keep up the occasional anal play and start to make it a lot more frequent. Getting into a routine of frequent anal penetration is one of the best ways to start training, and I advocate making it a standard part of your masturbation routine—every time you play with your clit, play with your ass at the same time. Regularly make yourself cum while you have something in your ass, further developing the association between anal penetration and pleasure.
As you feel comfortable doing so, try putting gradually increasingly larger things in your ass. Fingers are a good way to start, first with one, then two, then three, etc. Once you’ve run out of fingers to comfortably fit, try getting a butt plug or a dildo that looks like a good size a little larger than what you’re comfortable with already at that point. Just keep going gradually up from there at a pace that works for you, and once you’re around the size of an average penis without pain or discomfort, you’re probably ready to try it with a partner. Make sure it’s someone you trust and who will be patient and take their time if you need to pause or adjust or if something starts to hurt, and just listen to your body and back off if something starts to hurt, then try again.
Good luck and enjoy!