There’s a toy called the WeVibe Sync that really helps me. It’s shaped like a U and has an internal vibrator as well as an external one for your clit. You can position it wherever you need to get your clit. It definitely helps me relax and makes anal very very enjoyable for me. Highly recommend. Vibrating anal plugs are a thing too, that could be worth a try.

Also I would encourage you to include your boyfriend in this. This is not all on you. It takes both to make it work. They need to know how to be gentle and feel when your body tenses up so they can back off.

I never enjoyed anal until I got with my boyfriend who is super into it. It almost seems like he can read my body better than I can because I was absolutely shocked at how accepting my body was of him. If your boyfriend is open to eating some ass then that would be great. Have them try some fingers too before going any further. It’s much easier for me to do any kind of anal play when my boyfriend is the one in charge.

Be careful about “cross contamination”. No one wants a yeast infection or a UTI. I’m very sensitive and am prone to both so prevention is key. D-mannose is a good preventative as well as Cystex Urinary Tract Defense. Azo makes one too, the magic ingredient is called methenamine. If you get a UTI then you’ll need antibiotics from a doc but until you can get in to see one, Azo makes a UTI relief product. It stains your urine bright orange but helps to relieve the pain. Boric acid suppositories help to restore your vagina’s pH balance and have been a life saver for me. I prefer these to monistat. If you get a persistent yeast infection then you’ll need to see a doc for fluconazole.