Does anal hurt?

Hey guys I’m new to being gay figured out my sexuality about 2 months ago but my boyfriend asked me if we wanted to go all the way instead of me just sucking his dick (anal) I didn’t know what to say at that moment but wanted to ask you guys that have experience being bottom. Few questions, does it hurt? How much lube should he use? Should he wear a condom? And if y’all could think of anymore than please let me know!!! Thanks.