So me and my boyfriend are planning on "doing it" soon and he's the one bottoming so I need some advice on how to not make taking his virginity a complete disaster
I assume he's gonna be extremely squeamish and self conscious about everything, so wear protection. Then, the classic advice - lube, lube, lube. Be spontaneous about it, laugh, smile, reassure. Last but not least, take your time. If you wanna do it right, clear up the day before and after so neither of you have to focus on anything else but yourselves.
Be tactile. Massage. Rub your cock close to his arse at first without going in. Work up to it slowly and let him make the final move on you. And remember, both relax and enjoy it unhurried. Don't pump away straight away but keep it there and just feel. Good luck and remember how good your first time was.
Let it happen when it is mutual. Lube lube lube and let him ask to be penetrated. Credit to the comments before me. Take it very slow and communicate with each other and enjoy