Anal attempts?

Did anyone have to repeatedly try anal before it actually happened? Do toys really help???

My boyfriend attempted today, but it just isn’t happening. He said he’s gonna get toys for me, so I hope that helps “prepare” me 🤨.

I have bad connotations to it because an ex was weirdly obsessed with it, to the point he cheated on me with an underage girl who drove across state lines to take it in the butt the first night she met him at a hotel 🤦🏼‍♀️. Anytime I’d give in and let him try, he would be the dumbass thinking he can just shove himself in dry.

Since those years have passed, I’ve had a few times of being fingered and that’s it.

My boyfriend did everything right. He did oral & then we had amazing sex, then he got more lube on himself and me. He teased a little bit by spanking my butt with his dick and he went slow while simultaneously using my vibrator on me (we were doggy style). Add in some spanks and massaging parts of my body, with dirty talk, I was totally comfortable attempting it.

So I trust my boyfriend with making this as pleasurable as possible... I just want as little pain losing my butt virginity as possible so if anyone has been through what I have, with it trying to be forced on you forever and it being a sour topic, I’d love to hear from you.