All one has to do is take a look at Pornhub to see both are indeed entirely possible. Whether or not itu2019s enjoyable depends on the parties participating in said acts. Some women enjoy larger insertions, both vaginally and anally. Some do not. Some men enjoy the sensation of their penis against another mans penis, or they enjoy the act of double vaginal or anal penetration. It all depends on the person. That being said, female porn stars who participate in double vaginal or double anal generally practice on inserting bigger objects in themselves to prepare. Doing double vaginal or double anal without long preparation, with plenty of lube(especially during anal) can at the least result in extreme pain, if not possible injuries, including severe tearing so if your planning to give it a try make sure you use caution and have open communication with your partner(s).