That said, if everything goes does go well, there is a huge likelihood that your anal experience will feel amazing. There is no shame in anal not feeling right for you. But, be aware that anal touch and penetration can still feel uncomfortable even if all of the precautions are taken, patience is virtued and you’ve been swimming in a vat of lube. Stop, recalibrate, and try again when you want to. That stretching feeling may be a bit uncomfortable and being penetrated can produce a very 'full' kind of feeling, but a sharp pain is a bad sign. Gentle stretching with well-lubed fingers is a must before introducing a sex toy (especially a toy that has a bit of girth, like the LELO Loki Prostate Massager, pictured below) as is going slow. That’s a key phrase when it comes to anal-done right. Anal play can absolutely be painful and downright dangerous if it is not done right. The fear of anal play causing pain is real.
Busting any feelings about the above stigma and misinformation. And if there is, that can then be the catalyst for a bunch of different opportunities. First, it will help identify if there is mutual interest. Talking about anal sex first will provide the opportunity for two things.