If you were a true anal whore, you'd find someone to help you out in person.
In that spirit, name your three plugs. The smallest should be someone you've had sex with. The medium should be someone you've flirted with. The largest should be someone you crush on, but who you know is out of your league. Like, they'd laugh in your face if you flirted with them out of your league.
Got the names?
Good. You're going to work your way up to getting ass fucked by the out of your league plug. But you'll start with the small one. Strip to bra and panties. Say hello to your plug. Be flirty. Run your tongue over your lips. Ask him if he ever wanted to fuck a girl in the ass. Give it a little lick. Who are we kidding? Give it a looong lick. You want your ass filled, and you'll do whatever it takes to get it. Tell it you'll be its sex slave if it'll only fuck you in the ass. Lick it some more. Talk dirty. Earn it.
After five minutes of debasing yourself before your plug, flip a coin. Heads, you give it five more minutes of dirty talk and blowjobs while fingering your asshole.
Tail, you put it in and leave it in for at least ten minutes. You can touch yourself if you want, but no cumming. Your ass is for others' pleasure.
Take it out and clean it up. Report back, and we'll see if you can move up in the anal world.