My best friends boyfriend took my anal virgintity [FM] (BDSMish)

This is my first time writing something like this, so go easy on me!!My best friend, (we’ll call Catie) and her boyfriend (John) go to school in a different state. I miss them, and they flew up and visited me for my birthday.

Fast forward to my birthday party, and we’re all super drunk and playing Never Have I Ever. When it gets to me I start with “Never Have I Ever been fucked in the ass”. Catie mumbles something about me missing out and takes a shot. She comes up to me after and starts telling me I should try it, going on about how great John is in bed, etc. I had just gotten through a nasty breakup and was getting jealous and upset. She saw it on my face and whispered: ” John thinks you’re cute, it’s your birthday, go have fun”.I asked her if she was sure. She nodded and waved him over to us. After all three of us talked for a bit, she asked to go to sleep in my spare room.

After stalling a bit, John pulled me onto his lap. “Cat tells me your incredibly submissive” he whispered in my ear. I giggled and nodded a little. He kissed me and slid his hands up my skirt. He slowly started rubbing my clit, teasing me until I was dripping wet. I begged him to let me cum. I’m sure Catie could hear me through the walls. “You don’t get it that easy”, he growled. After lots more begging, he tossed me off his lap where I laid face down. He pinned my arms down and explained he would let me cum if I took his cock up my ass. I nodded. I was desperate for it.He stuck two of his fingers in my ass, then three. It hurt, but not as bad as I thought it would. He fingered me harder, telling me what a fucking slut I was for taking it up the ass.

He told me to get something to use as lube. I came back with coconut oil. He laughed but said it’d work. He told me to take a deep breath and slowly started into me. As the head of his cock slid into me, I screamed in pain. It was way bigger than his fingers. I started to pull away when he told me I was being a good girl, and that I was almost there. He started stroking my clit hard. The pleasure from it made me eager for more.

I started to cum and he slid farther into me. He started fucking me harder and harder. I started to squirt, dripping onto the floor. I had bitten down on my shirt to muffle my loud moans. He ripped the shirt from my mouth and slapped my cheek, saying he wanted Catie to know how much of a slut I was. This made me cum again and I was getting dizzy.

He fucked me harder and harder before pulling out. He shoved his cock down my throat before cumming on my face. We both caught our breath for a bit. “Happy birthday!” he said, and we busted out laughing.

Me and Catie woke up and gossiped about the night while John slept in. I hope they come visit soon :)

Source: reddit.com/r/gonewildstories/comments/c0cisq/my_best_friends_boyfriend_took_my_anal_virgintity

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