u/Thin_Rutabaga6312

So, this is the story of how I ended up losing my anal virginity, it was with a girl, and her toys.

I was in my slutty era, basically going out every single night with a new girl, taking them home, going to theirs, getting drunk and having girls bounce on it crazy style - it was fun.

Few weeks ago, I matched with this incredibly hot Scottish girl on tinder, to my surprise we lived pretty close, like walking distance in south London which isn’t easy to do. I ask her out for a drink and she says she’d rather make one for me at hers. I don’t need to be asked twice, so I walk on over.

Obviously she’s a smoke show, and she makes me a few lovely gin drinks. Eventually we start getting hot and heavy, and she asks if I wanna move to the bedroom, I say yes absolutely so we do.

You’re probably thinking it was some kind of sex dungeon but it’s pretty normal! Once I’m in she asks me by whispering in my ear if I’m into anal and I say absolutely yes. Then to my surprise she says “good boy” and pushes me onto her bed. She tells me to get on my hands and knees, now I’m horny as fuck and I don’t know where this is going to I comply. Eventually she pulls round the ropes and secures my hands down to the top corners of the bed. Now I’m getting a bit worried, so I ask what this is for and she says “stop asking questions, open wide” I open my mouth to ask another question but she’s already pulled out a ball gag and shoved it in. She tightens it up and calls me a good boy again.

Then she shoves a few pillows under my pelvis and pushes me down onto them, she pulls my legs together and pulls off my trousers and pants. Now I know what’s about to happen, and I’ve decided I’m along for the ride.

She pulls my legs apart spread eagle, and walks around to the side of the bed and shows me as she pulls on her harness, and secures a big pink dildo into the o ring. She says “aw you look frightened, I’ll be gentle good boy” she slides around behind me and I know it’s coming. I feel a thick Vaseline like substance being applied liberally to my asshole then she moans and I feel the head against my ass. I whine and whimper a little and she calls me a good boy again, and asks if I’m ready. I hesitate and she shouts this time “ARE YOU READY GOOD BOY” I nod reluctantly yes. And then I feel the head slide into my virgin asshole. And it hurts. I cry out in pain. She says “awww is it too big” she pulls out, and comes around to me again. I see her pour out a liquid that smells like dishwasher detergent into a plastic ziplock filled with paper towels, she positions it in front of my nose and the smell instantly makes three things happen

1. my boner is dead
2. I feel incredibly slutty all of a sudden
3. she was able to slide her really quite huge dick into my ass with ease.

I keep sniffing, and she speeds up. She’s moaning and telling me what a good boy I am, and at this point she’s basically jackhammering my ass, and I’m in ecstasy.

She pulls out fast and she shouts “wow” “look at that gape” I think my ordeal is over. She puts one, two, three, then 5 fingers and her thumb in my ass.

Now I’m wishing I could tell her to stop, because this hurts. And thankfully she does. She untied me and removed the gag. Flipped me over and told me to eat her until she cums. Which I do.

Afterward she tells me I took it like a champ, and I said “would you believe that was my first time” and she said “absolutely not you fucking slut!”

We never met again.