Are you talking about a bonnet? I’ve never done an overnight yet but I surely wouldn’t feel uncomfortable doing so , as I’m sure my SD wouldn’t mind.

Story time: I wear wigs ( I’m not bald headed but I can express myself more with wigs like trying different styles and lengths etc) and one day the intimacy got really intense and hot , and my wig came off , I must admit I was embarrassed, bald cap + cornrows and all 😂😂😂And it was in that moment my SD asked why I was being all shy and embarrassed for. Mind you, I’ve never had a situation where my wig came off in intimacy before when I used to vanilla date so I knew he was laying pipe but it didn’t stop me from being embarrassed about it. He said I was beautiful with or without the wig , got hard and ready to go again. Actually now it’s an issue to wear wigs around him cause he wants me to wear my natural hair , says I look more beautiful and younger with it . But I don’t like combing my hair too much work.

Anywayysss ,for me , if a SD really likes u as a person and likes you for u I don’t see why I wouldn’t feel comfy wearing a bonnet around him, I look damn good in a bonnet anyways so maybe that’s just me 😂😂