A/N: Hannah Montana was one of my favorite Disney Channel series (though I did not watch it all the time). This is my first fanfic based on it plus Lilly/Oliver story too. Used to have a crush on Mitchel Musso before his troubles with the law. The series is property of Michael Poryes, Rich Correll, and Barry O'Brien. Hope you enjoy the story and do leave reviews. Will probably write more Lilly/Oliver stories in the future.

I was out one Friday night cruising down the Sea View boardwalk with one of my best friends, Lilly, and while I was just wiped out, she was really buzzed. She recently had an argument with her Dad and was looking to have fun to get her negative feelings out, to the point of stumbling home, something which she complained throughout the night. I lived closer so I dragged her back to my place as it seemed safer.

"You're an awesome friend." She slurred when I helped her on to my couch. "You'll never take advantage of me."

"Yeah I'm a really cool guy, now please don't hurt yourself, Lilly." I said as I lowered her down. "Sleep it off and have good dreams."

With that, I went upstairs to try and chill out. I woke up in the middle of the night after an extremely hot sex dream about Lilly that I was hard even after I got up. I've had those about her before, and despite me trying she never wasn't into me as she saw me as a friend. I was thirsty and had the munchies as fuck, so I went downstairs to get a can of 7-UP and slice of pizza, and when I did I saw something that my dick way harder.

Lilly in her sleep had pushed off most of her dress. She wore a pair of ripped, faded blue jeans that showed off her body in all the right places. I loved it and jerked off to Facebook pics of her in them since she first bought them, but now she'd somehow pulled down the jeans to her legs showing that she shockingly wasn't wearing any underwear. Out of that red-white shirt one of her ample breasts popped out of the top of her bra as well. My first thought: get a blanket to cover her and jerk off after, but something else took over me.

I moved closer to her to nudge and call out to her to see if she would wake up. She didn't and was pretty much passed out. Her blonde hair a mess over my couch and her beautiful face. Her fine pussy was dripping wet, I guess she was having a wet dream too. I hesitated, thinking of what I wanted to do to her. I had spent hours jerking off and imagining what her boobs looked like and how her pussy would feel on my cock.

I was painfully hard and my cock was bursting out of my green boxers at this point and couldn't help it anymore. I pulled off my pants, pulled down her pink underwear more, popped out her other breast, and spread her legs wide open. Pulling a condom out of my pocket, I grabbed my cock and slowly entered her tight wet cunt that I dreamed of since Middle School. I wanted to fuck her since I met her, and my chance had finally come.

My cock was halfway in when Lilly started to stir. I froze scared that she was waking up and I quickly came up with a story that she consented to this but then she spoke and what she said made me even harder.

"Olly?" She said sleepily and turned her head towards me with those perfect blue eyes half open. "Fuck me!"

So, that's what got her so wet. I knew she was a Bad Girl but didn't know that. I grinned while shoving the rest of my cock into her cunt. She felt amazing on my cock, wet and tight as fuck. Better than jacking off at night to Miley and was worth the wait. I started to pump into her, fucking her slowly at first when she spoke again.

"Oh, Olly your cock is so hard!" Lilly moaned out. "God, it feels so big in me!"

I started to fuck her harder and she started to moan more and more calling me Big O all the while. Her tits were bouncing up and down to the rhythm of my thrusts, which made me even harder than I ever thought I could get. My cock felt like metal rod inside of Lilly's tight wet cunt.

"I love your cock deep in me, Oliver!" She let out after I started to fuck her harder. " Give it to me harder!"

Other than a few grunts and moans, I was quiet as I was fucking Lilly. I didn't want to wake her up fully. She started to play with her clit, moaning louder as she did. She was totally into it. I knew she was a slut but letting me fuck her was beyond anything. God she's amazing!

I started to fuck her harder and faster, grabbing her tits as I did. Fucking her was incredible and I was going to have her. Lilly was still passed out and was moaning "Olly!" louder and louder. Suddenly she started moaning loud and I felt her cunt tighten around my cock. She was coming to my cock, and I was scared she'd finally wake up. She didn't thankfully, but her cunt squeezed my cock so hard I almost came in her.

"Oh, Olly!" Lilly moaned as she came with a smile, "Thank you for that. I wanted to get fucked by you for so long. Your cock's just… amazing."

I pulled out just in time and shot my massive load across her body. Most of it ended up on her stomach and tits, but some ended up on her adorable face. Seeing her covered in me cum and looking wild was a hot sight, so I took a phone pic of her for future jerk off material. I covered her back up, kissed her lips and went to bed.

In the morning, she was half-awake, hungry, and a little bit groggy.

"Do you remember anything from last night?" I asked carefully, worried she'd remember our little tryst.

"Next time, cum in my pussy. It's my fantasy to get fucked like that." She replied with a smirk while pouring a glass of OJ. "But we can try again later, Big O."