Unfiltered Story #127633

In college I worked at a farm that gave horseback riding lessons. At the time I was cleanshaven and had lip piercings. This exchange with a student’s mother and grandmother happened one day while I was waiting for a lesson to end so my boss could hand the children over to me for help putting their ponies away.
Student’s Grandmother: “Don’t those hurt??”
Me: “Huh? Oh! The piercings? They hurt a bit to get, but they’ve long since healed and I don’t even feel them anymore.”
Grandmother: “But how do you put on lipstick?”
Me: (Not catching the implication) “I…don’t? Why would I be putting on lipstick?”
Grandmother: “You can’t possibly go around in those barn clothes all the time! You must put on makeup when you’re dressing up for things.”
Me: (Finally getting it) “Oh! No. No, ma’am. I’m a boy. I don’t wear makeup.”
Student’s Mother: “You’re a boy and you ride horses?!”
Me: “Yup! Bit of a minority, but we exist.”
Mother: “Are you gay or something?”
Me: “I am, but it’s funny that people assume that. I do a sport where I’m surrounded by athletic women in tight pants all the time; you’d think people would assume I was straight!”
Grandmother: “Are you REALLY a boy?”
Me: “Yes. Yes I am.”
Grandmother: “Like, for real? You’re not one of those girls going through a phase of wearing her boyfriend’s clothing?”
Me: “…I guarantee I’m 100% male.”
(Thankfully the children got off their ponies just then and saved me from continuing the conversation.)