Best Friend to Girlfriend

I woke up to the feeling of a hard cock pressing against the crevice of my ass cheeks. It was thick and solid, pulsating gently. I could feel someone's warm breath on my neck. The slow heaving of a bare chest against my back. The comfort of an arm wrapped around me.

I opened my eyes and took in my surroundings, trying not to move. I was in Jason's room. The memories of the night before rushed back. Dressing up like a girly ballerina and having my best friend fuck me. Making out on the couch and in the shower. Becoming Jason's new girlfriend. My little cock stiffened at the pleasurable memories.

It was Saturday morning and neither of us had anywhere to be. Jenna, Jason's "other" girlfriend, was gone for the whole weekend. That meant that today was entirely put aside for us.

I grinned to myself, savoring the possibilities...

I had been fantasizing about Jason for years, ever since we first met. He was everything I dreamed about in a guy my age. Strong and fit, tall, funny, with a goofy smile and piercing eyes. His reputation as a ladies' man made him all the more attractive because I had always viewed him as "forbidden fruit". But now, it turned out that he wanted me. It made my heart flutter.

Before bed, Jason had picked out a pair of pink boyshort panties for me. They were lace and hugged my round ass perfectly. I loved the feeling of the lace against my straining member. The panties made me feel naughty and girlish.

I lay in bed, letting the feelings wash over me. Enjoying being held by my best friend. As the morning sunshine poured into the room, I drifted back into sleep, comfortable and safe.

I awoke a short while later to movement. Jason's hard cock was rubbing up and down along my ass crevice through the pantie fabric. Jason was moaning gently under his breath. His arms tightened around me, holding me close.

I rolled my head back seductively and let out a light moan of my own.

"Mmmmm, good morning baby."

"Good morning to you, sexy," Jason replied.

His arms tensed around me, hugging me tightly.

"That ass of yours is irresistible. And I can't quite decide if your ass looks better in those panties than Jenna's does...but its damn close."

I wiggled my ass, letting it rub against his swollen member, giggling softly.

"And damn that butt was so nice and tight last night!"

Jason leaned in and kissed my neck, his arms holding me tight as he thrust himself against my ass.

"Fuck baby girl, you are so damn cute", he whispered in my ear as he kissed my neck and nibbled my ear.

I writhed in pleasure in his arms, reaching down to touch myself under my panties.

Releasing one of his arms, Jason reached down and started to squeeze my ass cheeks. Tenderly massaging them, he continued to kiss my neck delicately. I arched my neck back, cooing in pleasure.

Slowly, I felt his fingertips slide under the elastic waist of the panties. He began pulling them down, revealing my bare bum. His fingertips trailed down the soft skin, tracing the cheeks before he squeezed them again.

"Fucking delicious peach ass," Jason said, lifting the covers to get a view of my pantie-clad bum.

Bringing his hand to his mouth, he sucked on his index finger, covering it in spit. His hand returned to my ass and I felt the wet finger trail along my rosebud. He probed gently against my hole, getting it slick and moist.

His hand returned to his mouth and he licked his finger again, before it returned back. This time, he pressed in harder, letting his finger slide into my ass. I moaned loudly.

"Oh god Jason, finger my ass", I moaned.

"Mmmm, ya, you like that girl?" he replied seductively.

As his index finger fully slid into my hole, I felt him start to wiggle it around, searching for my prostate. Finally, I felt him press against the slightly firm tissue on the roof of the canal and I felt a rush to my head as he pressed against the sensitive nerves.

"Oh god yes!" I moaned out.

Jason started to rub the area, his finger probing in and out of my hole.

"Ya, you like being finger blasted like a good girl?"

"Mmmm, yes!!!" I replied.

Jason returned his fingers to his mouth, licking both the index and middle finger. This time he slid both into my hole, filling me up more and pressing harder against my sensitive p-spot.

As I lay in my best friend's bed, held firmly in his arm, Jason fingered me relentlessly, loosening my hole and sending waves of pleasure through my nether regions. My hard cock dribbled precum, still trapped within the lacy confines of Jenna's panties.

I had never experienced anything quite this pleasurable. My best friend taking time to focus on my pleasure and take care of me. It felt incredible.

"I don't think I can hold it much longer, Evan. I need to be back inside you," Jason said, breathing heavily into my ear.

"Do it," I begged, "Put your cock back inside me."

Spitting on his fingers and rubbing a large amount of spit onto my hole, Jason lined his large cock up at my hole, prodding it gently with the tip of his cock. My hole was loose from the fingering and from our vigorous lovemaking the night before. With a thrust, Jason's cock pushed through the sphincter and buried itself balls deep, bareback into my waiting boi pussy.

I sighed and closed my eyes as I listened to Jason's grunt of pleasure. His hand slid down my sides, holding my waist steady as he adjusted himself inside me.

My ass felt so full. His big cock, with its perfect curve, pressed against me in all the right places.

"Fuck me, baby," I begged lightly, my eyes closed as I let my body surrender to the ecstasy.

Jason started to spoon fuck me, his cock sliding in and out of my hole as he held me close in his arms. He laid soft kisses along my neck as he took me. I could feel his arm muscles tensing as I wiggled my ass against him and let my sphincter muscles contract around his heavenly shaft.

"You are fucking adorable," Jason groaned in ear, "Your juicy ass is so fucking perfect. I've fucked a lot of pussy, but this is the tightest...oh fuck!"

Jason rocked back and forth into me. He stayed so hard. I could feel his cock pulsating with every thrust.

He started thrusting faster now, with more purpose. Each thrust went deep and I could feel every inch of him sliding inside me.

"Oh god baby, am I your girl?"

"Yes, you're my baby girl."

As he fucked me in his bed, I thought back to that night I had masturbated in the hall outside his room, listening to him fucking Jenna. I could hardly believe that it was now me in his bed taking his cock.

I focused in on his breath, his moans, his grunts. They sounded just like when he fucked his girlfriend. Those sounds a lone had driven me to orgasm that night. Now, along with the sounds, I had the sight of this beautiful man, his smell fill my head, and, most importantly, the feeling of his manhood inside me.

"Baby, I think I'm gonna nut again," he whispered in my ear.

"Mmm, babe, not like this. I want to see your face when you cum this time," I replied.

"Mmmm, oh ya babygirl? We can do that," Jason replied, grinning.

Slowly, he pulled himself out of my tight hole. I felt it pop as the thick head slid out. Jason climbed on top of me. My whole body was underneath him now as he kneeled above me. His chest was heaving. I let my hands feel his thick thighs, massaging the strong muscles.

Jason reached down and pulled my panties off the rest of the way. They were stuck around knees, preventing me from fully spreading apart for him.

"Hmm, you're missing something," Jason said, looking down at me.

"What do you mean?" I asked, shyly.

Jason looked around the room and his eyes alighted on the closet.

"I know just the thing!" he said, still not answering the question.

My best friend jumped off the bed and walked over the closet, pulling it open. His fully naked body was on display now. I could barely keep my eyes off his marvelous cock, standing fully erect as he flipped through the closet.

After a moment, he pulled out a pretty purple babydoll nightie. Grinning like a kid in a candy shop, Jason walked over, unhooking the shoulder straps and handing the lingerie to me.

"Put this on for me baby girl," he ordered.

Feeling the fabric, I quickly pulled it over my head. The short spaghetti straps slid down to my shoulders and the silky purple fabric cascaded over my thin, smooth tummy and hard boi clitty.

Biting my lip like the girls do, I looked up at my friend expectantly.

"So, how do I look?"

"Like a girl I'm about to make sweet passionate love with," Jason replied eagerly.

He climbed back on top of me, grabbing my legs and lifting them up, resting my ankles on his shoulders. Pushing the skirt up to reveal my boi clitty and tight hole, he repositioned his hard member at my entrance, prodding it gently.

"Damn you look so fucking sexy, baby," he purred, eyes full of lust.

Collecting some spit in his mouth, he spat down onto his cock, massaging the lubricant onto his shaft with one hand, holding one of my legs up with the other. Positioning himself directly at my anus, he pushed in again, sliding in effortlessly as my body opened up to my lover.

He didn't waste any time. He started thrusting vigorously, pounding my ass ferociously. His hips were rising up and down as he pulled out almost completely then slammed back in.

I started to moan uncontrollably. My hand reached down and I started to stroke myself madly.

Jason slapped my hand away from my cock.

"Just enjoy the feeling of me inside you," he ordered.

I did as he said. I stared up at him, looking directly into his eyes.

It was the most intimate moment we had yet shared. You don't often stare directly into your best friend's eyes. That sort of intimacy is more reserved for a lover. But we were in that category now. He was looking at me with the same passion. I could tell that the depth of his feelings were the same as mine. He would protect me, care for me, love me.

I let my senses take over, feeling every thrust. Each time his cock pulled out, I yearned for the feeling of fullness to return. I would hang, for a brief second, in limbo, waiting for that fullness, before being satisfied. Again, and again, and again.

My cock was as hard as it has ever been. And despite not touching it, pleasure was radiating from my ass up the shaft.

"Oh god, I LOVE YOU JASON," I screamed as I felt the pleasure building.

Jason smiled and leaned down, putting his lips to mine. We shared an incredible kiss. His tongue explored my mouth as I moaned loudly into his, feeling the steady rhythm of his fucking.

As he kissed me, I felt a rush in my loins. Gasping, I pushed him off of me.

"Oh my god, I'm cumming!" I screamed as my first-ever, hands-free orgasm thundered through my body.

Jason grunted, his body stiffening.

"Fuck me too," he yelled.

Jason picked up his pace, thrusting furiously as he buried another load deep inside of me. My boi clitty was spraying cum all over the place as my lover continued to pound me. I could feel Jason unloading a huge amount of warm, delicious spunk into my tummy.

My own orgasm hadn't yet receded. As my cock dribbled out more cum, my ass muscles would spasm, milking more jizz from his cock.

My heart was racing so fast. I barely realized that tears were flooding down my face. I fought to control my breath. Still buried inside me, Jason collapsed onto me. He kissed me, stroking my cheeks and wiping the tears away.

"Sweet baby girl, don't cry," he said, "That felt fucking amazing."

"That was the best sex I've ever had," I moaned softly, starting back into his eyes.

"That was fucking incredibly, baby. You are an amazing fuck," he replied.

Jason stroked my cheeks, kissing them gently every few minutes. We were both still breathing heavily. I could feel my heart pounding and feel his own rhythm against my chest.

I felt his cock slowly start to shrink inside me.

"Mmmm, don't go," I whispered, my eyes closed.

Jason laughed as his now limp cock slid out of me with a wet "slurp". A little dribble of cum trailed down my ass.

My lover brought his hand down to my hole and slid a finger back inside the now wet, impregnated boi pussy. Scooping out some of his warm seed, he brought his finger up to my mouth.

"You want to taste my juices?" he asked mischievously.

Without answering, I took his finger in my mouth and sucked off all of his cum, tasting the salty treat.

He repeated this several times, scooping out more of his seed and feeding it to me.

"That's so fucking hot," Jason muttered, watching me lustily, "I absolutely love how obsessed you are with my cock and cum."

"I've been obsessed with your cock since the day we met," I replied giddily.

"I can see that now," he laughed.

He leaned down and kissed me again. I was surprised, because I thought he might be turned off now that my breath smelled of his sperm. But he didn't seem to mind. We made out and snuggled. I pressed my body against his and he held me in his arms again.

Finally, we broke out embrace.

"I'm going to go make us some breakfast," Jason said, rising from the bed.

I admired his fit torso as he walked around the room, fumbling on the ground for clothes. He pulled on a pair of tight grey boxer briefs and a t-shirt. He looked so damn sexy.

"You wanna go tidy yourself up and I'll call you down when it's ready?"

"Sure, sounds good baby," I replied, smiling. It felt nice that he was going to pamper me after filling me up.

"If you need a new towel, grab one from the closer."

"Oh, I won't be showering," I grinned, "I'm going to keep this load inside me all day."

"Good girl," Jason grinned, walking over to kiss me a quick kiss.

"So what's the plan for today?" I asked before he left.

"Well...you know my buddy Mitch? The one with the gym?"

"Uh huh," I replied, remembering Jason's beefy gym bro friend.

"He offered to open up the gym for me today to help me work on my deadlift form. I mean, we could both go over together if you wanted?"

I pouted my lips, "But you can't fuck me at the gym!"

Jason laughed, and then paused as if pondering something.

"You know...Mitch broke up with his girlfriend last month. He's been complaining to me about how all of the girls he's been with lately have been prudes. I bet you he's feeling pretty worked up..."

I stared at him confusedly, "You aren't suggesting that I..." I trailed off.

"Well...I'm just saying, in the right bootie shorts on the treadmill, you never know..."

"But Mitch is straight isn't he?"

"Ya, but I mean, so am I," Jason laughed, "And you are just about the cutest girl I've been inside of. Let's have some breakfast and we'll conspire."

With that, Jason headed down the hall.

Gathering myself up in bed, I slipped out and admired myself in the mirror. The purple babydoll cascaded down my slim, smooth body.

I looked through the make up that Jenna had left on her dresser. Pink lip gloss, nail polish, and hair bands.

"If I'm going to try to seduce another straight boy, I'm going to have to look really pretty," I thought to myself.

But damn, having both Jason and Mitch inside me at the same time. That would be another dream come true...