Message: Making Anal Less Painful

Anonymous: How can I make anal less painful?

Anal shouldn’t be painful at all. If it hurts, you probably aren’t ready to have anal sex yet and should focus more on anal masturbation/training before resuming anal sex.

Experiment with how many fingers or what size toys you can fit in your ass without it hurting. Make sure you use lube. Start at the small end and work up in size gradually after warming up and getting used to each size. If it hurts when you go up in size or add a finger, go back down in size again for a while and try again.

After you can easily and regularly fit 3 or more fingers in your ass, get yourself a nice butt plug about 1.5″ at the widest and start wearing it when you masturbate, and for half an hour or more before you have sex.

When you’ve been anally masturbating for a while and feel ready to try having anal sex again, wear the plug for a while first, then when you do the initial penetration with your partner, take control at first of how deep and fast to take him. If it starts to hurt, pause a moment. Push out as if going to the bathroom to help relax and open up. Resume. Repeat as necessary. As you can take him in all the way and start speeding up, he can start moving as well or taking control, but make sure he will pause for you if you tell him it’s starting to hurt.

Keep practicing, keep wearing a plug, always masturbate with something in your ass, and it will keep getting easier and easier to enjoy anal with no pain at all.

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