I will refer to the guy as Buddy. Every time I needed a hard fucking, he was there with his full erection. Always made me cum first. Never denied me a fuck when I wanted one. A true woman-pleaser.
After about a month of fantastic sex, Buddy starts hinting at putting it in my ass to which I respond “No, I have never done it before and do not want to.” He goes on talking about how he’s done it lots and many women enjoy it. Tells me I am just the type of woman that would enjoy it and should at least try. With him. His big dick in my ass. Still I say no. But he keeps bringing it up. Not forcefully. Just hinting that I would enjoy it.
One day I am curious. I cover my mascara tube in lube and slide it in my butthole. That was not bad at all. I am amazed at how easy that was. Next I take my hairbrush handle and cover it in lube. I do the same. It is a bit more difficult but still, easier than I thought. I call Buddy, tell him what I did, and that he should come over immediately.