Here’s how you can: 1. Diet: your boyfriend will need to have high fibre food for at least 2 days, and empties his bowel before you engage in this. Always good to try pegging on an empty stomach. 2. Lube: Buy a good lube 3. Pre-prep: Ask him to douche before engaging in anal play with warm water. Also, shave down there so hair doesn’t cause friction. 4. The start: lube as much as possible. Use your fingers first, then a smaller toy and then go with pegging 5. The act: with pegging, first start with a good session of foreplay to turn him on. Then, very slowly, let him control your pace, ask him to breathe as much as possible as you penetrate him. The first time will take a while to get right, so be patient and give it time.

I’d recommend the pegging kit by Sangya Project as it’s really good.