Best Friend to Girlfriend Ch. 01

I had had a crush on my best friend for years. Jason was the athletic one, I the bookworm. Our friendship was unlikely but, for some reason, it worked.

We met in college and, over time, became inseparable. For many years, it was normal for one or the other to be asleep at the other's house. We played video games, talked about everything and anything, and enjoyed time in the outdoors.

Jason was a competitive swimmer. He was tall and lean, with strong legs. At 5"9, he was the taller of us, with broad shoulders to boot.

Despite not being athletic, I took care of myself. I was pretty slim and was particularly proud of my ass, which I considered to be perfectly round after years of squat workouts.

For years, Jason was the lady's man. He dated a ton of women and brought home many more. Much shyer, I didn't have much experience at all with sex. But I loved hearing his stories about all of the girls he had fucked.

I figured Jason told me the stories expecting that I would be jealous of all of these women. He was almost right. I was jealous, but not of him...of all of the girls.

As we got older, I knew that I liked men. Instead of picturing myself pounding hot cheerleaders, I imagined being on my knees in the locker room, sucking on the hard cock of the hot athletic guys. I pictured myself being pushed against the wall of the shower and feeling a hard cock slide inside of me, filling me up.

And, to my shame at the time, I pictured myself dressed in those girly cheerleader outfits, skirt pushed up over my perfect ass, as I took a huge load of cum inside my boi pussy.

I was a secret sissy.

And my biggest crush was on Jason.

I don't remember when I started thinking about him sexually. It probably happened slowly over time. I remember one day as we were getting changed to go to the gym, I noticed the line of his thighs and calves. They looked so strong and I couldn't stop imagining them thrusting. When I'd go to his swim meets, I would let my gaze linger on his chest and arms, admiring every muscle of his smooth torso. At night, I would think about his body, and about his cock.

Soon enough, I found myself hopelessly obsessed with him. But I knew I could never say anything. Jason was the straightest guy I knew. There was no way he'd be interested in his secret fag friend.

What's more, when we both turned 20, Jason got a long-term girlfriend.

Jenna was also in the competitive arena. She was a professional ballerina. One of Jason's friends introduced the two and they hit it off. I had to admit, it was a good pairing. They pushed each other.

After they moved in together, I would still occasionally sleep over at their apartment if Jason and I had been hanging out.

One night, after the three of us had been watching a movie, I decided to head to bed early. I slinked off to the guest room and fell asleep quickly. A few hours later, I woke up. I could hear something. I listened intently.

It was definitely Jenna. It was a higher pitched sound, muffled through the walls.

I got up and quietly walked to the wall that separated the guest room from the master bedroom. As I approached, the sounds became clearer.

"Oh fuck Jason, yes, fuck me. Oh fuck yes!!!" came the moans.

I froze, my heart beating.

I had heard so many stories about Jason fucking girls, but had never been this close to it happening. My little cock stirred in my boxers.

I listened more closely.

"Fuck ya girl, take my big cock," Jason was saying. Jenna moaned loudly in response, obviously enjoying taking her boyfriend's cock.

I reached down between my legs and started rubbing myself. I couldn't help it. The sound of my crush having sex was so arousing. I could imagine him saying these naughty things to me.

I had to see more.

If I stepped outside the bedroom, I knew there was a chance I could get caught. But it was a risk I was willing to take. I figured, at worst, that I could plead ignorance and say that I was going to the bathroom.

Quietly as I could, I crept over to the door and opened it gently, stepping into the hall.

The door to their bedroom was slightly ajar. Closed enough that I was largely concealed from their view, but open enough that I could see some of what was happening inside. I peered through, happy that the moonlight was bright tonight.

Jenna was riding Jason. She was wearing a pink ballerina outfit, complete with frilly skirt. Jason had his hands around her waist, holding her firmly as she bounced up and down on his cock.

"Fuck me Jason. Fuck my pussy. Oh fuck yes baby!" Jenna purred, gyrating herself on her boyfriend.

"Take it, slut. Take that Daddy cock," Jason replied. I could see him thrusting quickly, ploughing into her pussy.

"Oh fuck yes, your my Daddy!" Jenna moaned.

I reached down and grabbed my erect cock and started to stroke, pushing my boxers down.

As I watched my friend fuck his girlfriend hard, I stroked my little cock frantically, imagining it was me in the bedroom, dressed in that pink outfit, being ravaged by this handsome hunk.

"Oh god, I'm gonna cum baby girl. You want Daddy's cum?" Jason grunted.

"Yes, give me that cum Daddy!"

My eyes rolled back as I felt my own orgasm building. As I listened to Jason moan out in pleasure as he shot his load, I did the same. My cum shot out and splattered on the carpet. I put my forearm in my mouth to stifle the gasp of pleasure.

As I regained control of my breathing. I realized that the couple were starting to move around. Scared that they would notice me, or worse come out into the hall to go to the bathroom, I quickly retreated into the guest room and back under the covers.

As I lay there, my heart was still pounding. The orgasm I had just had was possibly the best of my life. I had been so close to my fantasy: hearing Jason actually fucking someone, hearing his dirty words, and the sound of his moans as he came. All of it helped flush out the dream I had masturbated to so many times. It was probably the closest I would ever come to that fantasy. But for that night, it was more than enough...

--

A few weeks later, my phone buzzed while I was in class. It was a Friday afternoon and I was already starting to zone out of the lecture. It was Jason.

"Hey man, Jenna is away at a performance this weekend. Want to come crash at my place tonight?"

I hadn't slept over at Jason's since the incident that night. Remembering it instantly made me hard again, and I crossed my legs under the desk to hide my embarrassment.

"Ya man," I replied, "I'll head over when I'm done class at 5:30."

In no time, I was over. The evening progressed as it normally did. We had pizza, drank a few beers, played video games, and talked.

At around 1AM, I could tell that Jason was a bit buzzed and was getting tired.

"The one thing that sucks when you have a steady girlfriend is that when she goes out of town you can't just find another girl to fuck," he said drunkenly, nursing his beer.

"Ha! Missing your girl already? It's only been a day!" I replied.

"Evan, you have no idea. Jenna was busy rehearsing all week and was too tired to fuck whenever she got home. I've been so horny but she wouldn't so much as give me a handjob...girls, ugh," he sighed.

I laughed and grabbed the remote as the tv show we were watching finished. I started flipping through the options on Netflix, settling on something else.

"You good with this?" I asked.

Jason didn't respond.

I looked over at him and could see him breathing heavily, eyes closed. He seemed to have fallen asleep.

I pressed play and let the show start, figuring the sound might wake him.

It didn't. He seemed to fall further asleep.

For the first time in a while, I got to look at him closely. He was laying on the couch, wearing a pair of lululemon shorts and a hoodie. He looked like the perfect person to snuggle with while watching a show. His muscular legs were stretched out, still as impressive as the first time I had noticed them.

His face was also perfect. A sharp jaw with wavy blonde hair. Even passed out, he looked peaceful and handsome.

I pictured that face contorting as he came that night. Pictured those legs tensing up as he sprayed cum inside his girl. Imagined those hands holding my sides firmly...

My cock hardened quickly inside my boxers.

I thought for a moment about jerking off quickly. From my couch, I could seem him perfectly. If he stayed asleep, I could probably quickly shoot my load without disturbing him. The idea aroused me further.

But then, I got an even dirtier idea.

I remembered the outfit Jenna was wearing while Jason fucked her. That pink ballerina outfit. It hugged her slender, powerful body. The skirt cascaded over her dancer's ass. How I wished I could wear it, just once.

I wondered if it was still here, in the apartment, or if she had taken it with her.

I glanced over at Jason, making sure he was still asleep, and then crept down the hall to their bedroom. My heart was pounding in my chest and I knew if I was caught, I would have a hard time explaining why I was looking in their closet. But I absolutely had to try.

Inside their room, I pulled my phone flashlight out, shining it around the room. It was obvious that Jenna had made the bed before leaving and tidied up. Jason's room was never this clean when he was living on his own. I crossed the room to the closet and opened the door.

Jenna had a lot of clothes. But as my flashlight passed over the racks of outfits, I saw the hint of pink glancing through. I pulled out the ballerina dress.

It was a nice texture of soft cotton, a beautiful and feminine baby pink colour.

I pressed it against my face, enjoying the texture.

I stripped down quickly, listening through the quiet apartment for any signs of Jason moving. Soon, I was standing naked in my best friend's bedroom. I pulled the skirt and chemise over my head and wiggled into it. Amazingly, it fit well, hugging my slender body. I felt the skirt brush against my swollen cock, tickling my ass. Turning to admire myself in the mirror, I gushed with excitement. I thought I looked soooo good.

Before leaving, I opened the drawers in the dresser. Sure enough, I found one full of stockings, socks, and pantyhose. Wanting to complete the ensemble, I picked out some white pantyhose and pulled them up my legs. My slim legs now looked perfectly feminine.

I grabbed my boy clothes and carried them back to the guest room, figuring I might be able to make a quick getaway if Jason began to stir.

Then, feeling incredibly nervous, I tip toed back out into the living room.

Jason was still asleep. The tv was still playing. I crept over to my couch and sat down, laying back into the cushions. I ran my hand over the material hugging my body, feeling so girly. Then I reached down and gripped my throbbing cock. I started to rub myself, letting my smooth hand glide over my boi clitty as I pictured riding my best friend while wearing this outfit. I watched him sleeping, picturing the scene in my head. Remembering his words. Imagining him pushing this skirt up as he took my ass.

As I stroked more quickly, frenetically, I felt drunk on arousal. It made me more reckless.

"Oh Jason, fuck me, make me your girl," I breathed under my breath.

Jason stirred.

I froze, hand gripping my cock. I watched him, hardly daring to breath.

After a few moments, his eyes didn't open. I relaxed, figuring he was still asleep.

Then he opened his eyes.

I felt fixated in place on the couch, as if I had been turned to stone. I was seated on the couch facing him and he could clearly see my full, girly outfit, the skirt tented by my boi clitty. I felt a rush of blood to my face, knowing it was now blushing scarlet.

"Jenna?" Jason asked drowsily.

Then he rubbed his eyes and opened them again.

"Holy fuck, Evan! What the hell are you doing?"

Trembling, I sat there frozen, unable to speak.

"Why are you dressed in Jenna's stuff?" Jason asked, sitting up and looking at me properly.

"I'm umm...I'm...I'm so sorry Jason!" I stuttered. "It's just a bad joke, I swear!"

"Evan, this isn't a joke. You're hard as a rock," he said, gesturing to my very evident erection under the skirt.

I blushed even more. My flight instincts were engaged. I stood up, thinking I would run to the guest room, get changed, and then leave. My friendship was clearly over.

Jason stood up with me and placed his hands on my shoulders.

"Calm down, Evan. Deep breath, sit down," he said, pushing me back down onto the couch. He sat down next to me.

"So you, umm, you like wearing girl's clothes eh?" he asked.

I nodded, ashamed.

Jason reached over and nudged my chin up, forcing me to look at him.

"You don't need to be embarrassed," he said, looking me in the eyes. "You actually look really sexy in that outfit."

"Really?" I asked him skeptically.

"Ya!" he laughed, "Jenna has always been jealous of how great your ass looks and, to be honest, I've caught myself looking at it a couple of times too."

He placed a hand on my back and gently started rubbing it.

"So how long have you enjoyed dressing up girly?" he asked.

Still hardly believing what was happening, I tried to respond, "Well, umm, I guess for a couple of years now."

"Are you gay?" he asked.

"Ya, I think so. Or bi. Either way, I know I'm attracted to you," I replied nervously.

"Well, that makes a lot of sense," Jason replied, smiling, "We always kind of wondered why you didn't have any girlfriends. You were crushing on me, eh?"

I nodded.

"That's ok man, no need to be embarrassed. Actually, I guess I shouldn't be calling you "man" eh? Does baby work?"

I looked up at him and smiled weakly.

"It's ok baby," he repeated, still stroking my back, "We've been friends for years, it's only natural that you developed some feelings for me. And, to be honest, dressed in that skirt and outfit, you do look pretty hot."

Gently reaching over, Jason took my hand. He squeezed it gently.

"I've got an idea," he said, "I'm horny as fuck and you've clearly been fantasizing about this for awhile. I know we can keep secrets with each other. How about, for tonight, you be my girlfriend? That way, you can try out your fantasy and get it out of your system. Would you like that?" he asked.

"Really?" I asked him, hardly believing my ears.

"Really," he replied, gently moving my hand onto his crotch where, through his shorts, I could feel an erect cock.

I squeezed his erect member, looking my best friend directly in his eyes to see if he was messing with me. He let out a moan as my hand caressed his throbbing cock, which was clearly aroused. I let my fears wash away and decided to go for it.

I wrapped my hand around his cock through the fabric and started to stroke it gently, watching my best friend's reaction. He closed his eyes and moaned gently.

"Fuck man, I really need this," he said, eyes still closed.

I slid onto the floor in front of him, on my knees. Dressed in my frilly pink skirt, it felt like I was meant to be in this position in front of this hunk.

I reached up and slid my fingers under the waist band of his shorts and pulled down. His shorts came off quickly. He was wearing grey boxer briefs underneath. The shape of his cock was clearly outlined underneath...and it was as beautiful as I had imagined. Big and thick, straining against the briefs. Succumbing to my arousal, I leaned down and kissed his cock through his boxers. Jason let out another loud moan.

I kept rubbing it gently, mouthing my lips against his shaft and balls, making the fabric of his boxers wet with spit.

"You're killing me man," Jason laughed, "Take my fucking dick out and suck it like a good girl."

I grinned, loving his commanding tone.

Slipping my fingers under the elastic, I gently maneuvered his brief's down, unleashing his big cock.

It was spectacular. No wonder so many girls at school had talked about him. It was long and strong, with a nice curvature. Cut, his cock head stood out at the end proudly, a little thicker than his shaft. I felt the drool dripping out of my mouth.

"Omg Jason, it's beautiful!" I exclaimed excitedly.

"Ya, you been dreaming of that cock for years eh, baby? You just wanted to wrap your girly lips around it?"

I did just that.

Taking his cock in my hand, I leaned forward and took his cock head into my waiting mouth. I laid his bulbous head on my tongue and let it rest there for just a moment as I savoured the feeling of my best friend and biggest crush's cock in my mouth for the first time.

Then I started to suck him, slowly picking up the pace as I bobbed my head up and down his shaft.

There was so much cock to take. I couldn't quite take him balls deep, but I certainly tried. My tongue frantically worked on his dick, gently massaging the sensitive parts.

I knew from all of his stories that Jason had gotten a lot of blowjobs over the years. But I wanted this one to be memorable.

Opening wide, I worked to take as much of his cock in as possible, feeling his cock brush against the back of my throat.

I gagged slightly but kept going, letting his cock brush against the back of my throat as it convulsed around his sensitive tip.

Whatever I was doing was clearly working. Jason was moaning like crazy and egging me on. His hands were on my head, pushing me down further and deeper.

"Oh fuck babygirl, take that cock. Ya deep throat that big dick. Fuck yes baby," he cried out as I sucked his manhood.

Suddenly, he pulled out and stood up, forcing me to back up a few paces.

"Come here, I want to fuck your face baby," he ordered.

I returned back, looking up at him innocently.

"Show me your tongue, slut," he ordered.

I let my tongue hang out greedily, begging him for his erection again.

"Good girl. Jesus, Evan, if I had known you were such a hungry slut, we could have been doing this for years. You suck cock really good!"

I smiled to myself at the compliment, feeling giddy that I was giving him what he wanted.

Then he shoved his cock back into my mouth. His hands grabbed the sides of my face and held it firm as he started to plow into my mouth.

I spluttered and gagged, but kept my composure as he fucked my face, his moans becoming louder. I could feel every inch of his rock-hard member sliding in and out. His precum was leaking into my mouth, filling it with a musky but delicious flavour.

I felt like the perfect girl. On my knees, dressed in pink, letting my man use my mouth however he wanted. I looked up at Jason eagerly, hoping for more reassurance.

He didn't disappoint.

"Fuck baby, Jenna doesn't let me fuck her face like this. It feels incredible."

I moaned with happiness at his words. I felt my cock throbbing and dripping its own precum under the skirt. I reached down and rubbed myself playfully, letting the feelings of bliss wash over me.

Finally, he pulled out and I let out a gasp as I sucked in air. Jason stood above me, stroking his impressive cock, breathing heavily.

"Fuck, that felt incredible," he said, catching his breath. His chest was heaving. He reached up and pulled his hoodie over his head, now standing completely naked in front of me. His body was perfection. I admired every crevice of his abs, the definition of his arms, the line along his thigh showing his powerful legs. Most of all, I drooled over his cock, the object of my dreams for so long.

"Stand up baby," he ordered.

I got to my feet unsteadily. He grabbed my sides and pulled me against his chest. I looked up at him, nervously biting my lip.

Then my best friend did something I wasn't expecting. He leaned down and kissed me.

As our lips touched, my cock jumped under the skirt. He kissed me hard, his tongue darting into my mouth as his hands pulled me against him.