Ask him to check in with you to make sure you’re OK. Practice communicating, giving him feedback about speed, depth, pressure, etc. Have your friend use his fingers and/or your toys on you. Next, I recommend that you and your friend have a few sessions where you focus on anal play instead of anal sex. Tip #2: Avoid pain by trying anal play before anal sex. This will also help you stay more relaxed when you experiment with your partner. If you’re nervous about girth issues with your partner, you can start with a very slim dildo and slowly work your way up to bigger and bigger dildos to get a sense of what size you can take. A flared base ensures that you’ll avoid a trip to the emergency room. Your anal sphincters are surprisingly strong and can actually pull sex toys up into the rectum. If you’re using a toy, make sure that it has a flared base, meaning that the base is wider than the toy itself.
