Tip #1: Work up to your partner's size on your own.
First, I recommend you get more familiar with your own anus and rectum. (The anus refers to the outside part and the rectum is the inside.) Try playing with your ass as you masturbate. You can use a lubed-up finger or a slim, lubed-up dildo.
If you’re using a toy, make sure that it has a flared base, meaning that the base is wider than the toy itself. Your anal sphincters are surprisingly strong and can actually pull sex toys up into the rectum. A flared base ensures that you’ll avoid a trip to the emergency room. 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. This will also help you stay more relaxed when you experiment with your partner.
Tip #2: Avoid pain by trying anal play before anal sex.
Next, I recommend that you and your friend have a few sessions where you focus on anal play instead of anal sex. Have your friend use his fingers and/or your toys on you. Show him what you’ve learned you like. Practice communicating, giving him feedback about speed, depth, pressure, etc. Ask him to check in with you to make sure you’re OK. Also, you can tell your friend ahead of time that you’re a little nervous and want to make sure that you go slow.
It opens you up properly and prepares you for landing .It ensures that your anal pathway is properly prepared to avoid pains or tears during anal sex even the Dick is huge
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Tip #3: If you remember just two words, let them be "foreplay" and "lube."
When you’re ready to try anal sex again, spend plenty of time hooking up before. You want to be as relaxed and turned-on as possible. If you can have an orgasm before anal sex, that can help your entire body relax. Also, make sure to play with fingers or toys in that session, before you involve his penis.
When you’re ready for his penis, make sure to lube. Seriously, a ton. Lube up his penis, and you can add some lube to your anus, too. For anal play, I think silicone-based lube works best; it has a thicker consistency and tends to last longer than water-based lubes, so you won’t have to reapply mid-session.
Tip #4: Go slowly and communicate openly about the sensations you're feeling.
Remind your partner that you’re a little nervous, and let him know you need to go as slow as possible. Have him press his penis against your anus, and hold it there while you breathe slowly and deeply. I recommend you be in control of the insertion, so you can control the exact speed and depth. This works well for doggy style and with you on top.
Try pushing your body against his so that his penis goes in about an inch. Pause there, and keep focused on breathing and staying relaxed. If that feels OK, try another inch. Work your way down the length of his penis as far as you feel comfortable. If you’re feeling good, you can try moving up and down on his penis, or letting him take control of the movement. Keep communicating to let him know how you’re feeling.
Finally, if you experience pain or discomfort at any point, ask your partner to take a break. Have him stay still, while you focus on deep breathing. If the discomfort subsides, you can start again, slowly, with either of you in control of the movements. If the discomfort doesn’t go away, or if you feel pain, tell your partner to stop. Do not force yourself to keep going. Anal sex should be pleasurable, not painful.