Here are my top tips to have the best pegging experience possible whether you are a bottom or the top.
1.
Go Slow. Slower than you think. If it's your first time having anything in your ass it's unlikely you'll be able to handle more than just a finger or similarly sized toy. Practice makes perfect. The ass is like any other muscle, it needs to build up strength and endurance!
2.
Lube Lube Lube! Use more than you think. And then even more than that.
3.
Drop your expectations. If you're obsessed with a specific outcome you're going to be focused on that and tense. Relax. It's the journey, not the destination: enjoy the ride. (Honestly, This applies to all sex.)
4.
Communicate with your partner. How does it feel? Do you need more lube? Different position? Slower? Use your words.
5.
Pee first. One of the signs of approaching prostate orgasm is the sensation of needing to pee. Do it first so that you can rest assured.
What else would you add to the list? What has separated your best pegging experiences from not-so-great ones? If you've never been pegged, what would help you feel comfortable your first time?