Best Friend to Girlfriend Ch. 01

I had watched Jason kiss many girls at parties over the years. Now I was one of his girls.

I let out a sigh as we kissed, succumbing to his control.

When he broke the kiss, he looked me in the eyes.

"Baby, you're mine now. I'm going to fuck you properly now and make you my girl."

I nodded approvingly.

He turned me around, placing his hand between my shoulder blades and pushing me down. My ass popped up, the ballet skirt cascading over it. I balanced myself on the couch, letting my man have full, unobstructed access to my bum.

Jason stood behind me, his hands caressing my butt. He pushed the skirt up and rubbed the cheeks, massaging them.

"You have such a nice ass, baby. I love how perfect it looks in this skirt."

"Jason, please fuck me. Make me your girl," I begged.

He licked his fingers and reached down, rubbing my hole.

"I always wanted to try fucking Jenna in the ass, but she would never let me. Now I finally get what I want," Jason grinned.

I moaned as his fingers started brushing my hole, feeling myself getting weak in the knees.

His fingers were slippery, and before long his middle finger started poking my hole, prodding it gently. I opened myself to him, letting myself relax.

His finger slid inside me, gliding down the tunnel. I gasped in pleasure.

"Ooooh, fuck yes Jason, that feels so nice," I cooed.

Then he added his index finger. Now he was properly fingering my ass, the two digits sliding in and out as I moaned.

"Good girl, baby, moan for me."

"Ooooh god, Jason, don't stop. Please make me yours."

He withdrew his fingers and I felt him get closer to me. I heard him spit again and felt his finger pushing saliva into my ass. He did it again, and I turned my head to watch him rubbing his slick spit all over his cock.

"No looking baby," Jason ordered, pushing my head back.

Then I felt his cock between my cheeks. The shaft was warm and thick, pulsating against my soft skin. His hands grabbed my ass, pushing the cheeks together as I slid his cock between them. It was so wet down there, the cock slid back and forth easily.

My best friend humped my ass, holding the cheeks firmly.

Then, I felt his right hand guiding his cock head toward my hole.

"Are you ready baby? Are you ready for me to fuck you?" Jason asked.

"Yes!" I cried out desperately, "Please fuck me!"

Jason pushed his cock head into my hole and started to slide in.

At first, I felt the pain as my hole stretched. I cried out, trying to ride it.

"Oh god, Jason, it's so big!" I cried out in my most girly voice.

"Calm down baby, you can take it," he said, reassuringly, his hand resting on the small of my back.

Slowly but surely, he fed his cock into my ass until his was buried inside me. I felt every single inch stretching me on the inside, pressing against my prostate. The pain turned to warm pleasure.

"Good girl," Jason said, leaning down and pressing his chest against my back, wrapping his arms around me comfortingly. "Damn, that hole is incredible. It's so tight."

His kissed my neck and nibbled me ear playfully, before standing back up. His hands moved down my body to my hips. He grabbed them firmly and started to pull back out.

"No, don't go!" I cried, worried that he might have decided he didn't like it after all.

"Oh, don't worry baby, I'm not going anywhere. I'm going to pound your little boi pussy and given you all my spunk."

As he reached the rim of my ass, he paused, and then plowed back in. I let out a yelp, but was pleased to be filled again.

He started fucking me. Sliding in and out, in and out. His cock felt incredible inside me. His hands on my hips, holding me like a proper girl. My skirt bouncing around as his fucked me.

He fucked me doggie style. I knew this was his favourite position, because he had told me countless times. He slapped my ass playfully every once in a while as his cock drilled my girly bum. I wanted to ride him, but hoped there would be other opportunities to try that. For now, I wanted to give him exactly what he wanted.

"Fuck me Jason!" I moaned, reaching down and grabbing my own cock, stroking it frantically as my friend fucked me.

"Fuck baby, take that cock. Oh my god you feel so good, Evan. Your ass is so fucking tight!"

"Keep fucking me, please don't stop!" I begged, my back arching with pleasure.

Jason obliged, fucking me harder and faster. He was jackhammering his cock into me. I reached back and felt his legs. They were tensed as he fucked me. They felt so powerful and I loved being at his mercy.

"I'm not wearing a condom, but I'm getting close," Jason cried out.

I blushed. I loved the fact that he thought of that, even though I wasn't actually a girl.

"It's ok, you can cum inside me. Shoot your load bareback in me. Then I'll really be yours."

"Oooohhh fuckkkk!" Jason replied, his pace quickening.

I felt his body tense. I had been stroking myself as well. I was so hard. My pace quickened to match his.

Then he rammed his cock in as deep as he could and held me there. I felt a flush of warmth inside me as Jason let out a roar.

The feeling of my friend dumping his seed into my skirt-clad ass was too much for me. I let out a girly scream as my own orgasm hit me. I started spraying cum all over the couch beneath me. My anus spasmed, milking Jason of every last drop of his spunk.

My knees gave out and I collapsed into a pool of my juices on the couch. Jason collapsed on top of me. His chest was heaving up and down.

We lay there for what seemed like hours. He was still buried inside of me. My cock was still dribbling cum gently. We were a tangled mess of sweat, cum, naked man, and pink ballet cotton.

I felt something change inside me. Jason's cock was starting to shrink. As it did so, his cock slowly slid out of my ass. A dribble of his cum came out with it.

Manipulating me like I was as light as a feather, Jason turned me over so I was facing him. He leaned in and kissed me.

We made out like two teenagers in their parent's basement. I giggled whenever he would kiss my neck or nibble my ear. His hands explored my body and I did the same to him. Running my fingers over the parts of him that I had always stared at. I felt like I was in a dream.

"That was incredible," Jason said finally, breaking the comfortable silence of our kisses.

"It really was," I replied.

"I can't believe you never told me before how you felt. We could have been fucking for years," Jason said, laughing.

"I was always too afraid. You never showed any interest in guys, so I figured you weren't interested."

"I don't even see you as a guy right now, baby, you look like such a pretty girl."

I blushed.

"You don't think it's weird at all?" I asked, nervously.

"If my best friend wants to dress up like a hot girl, that's fine by me. Just so long as you take my dick whenever I want," Jason responded, smiling mischievously.

I smiled and leaned over, kissing him boldly. "You can have me any time."

Jason laughed and slapped my ass playfully.

"Come on, let's take a shower together and head to bed, I'm wiped. You're sleeping with me tonight, just in case I'm hard in the morning. You can wear some of Jenna's panties."

I grinned widely, happy not to be exiled to the guest room. My life had changed that night. I didn't know what the future held, but I knew there was more fun yet to come. My dreams were becoming my reality. This weekend, I wasn't the best friend anymore. I was the girlfriend.