Rooming With My Best Friend - With JJ (Fantasy)

ROOMING WITH MY BEST FRIEND – WITH JJ

This is a fantasy chapter written by Big D. This chapter is total fantasy and did not really happen.

There have been few times in my life when I can remember being genuinely happy, outside of my relationship with Matt, of course. The time that meant the most to me, however, was the party in my hometown a few months ago when a lot of the people who had treated me so badly in high school finally came to accept me for who I am.

Of all the people there that night though, it was JJ’s opinion that mattered the most to me. At first I thought it was just because he was seen as the leader of the pack still. Even though we were no longer in high school everyone still looked to him to set the standard and to make the decision as to what was and wasn’t acceptable. So when he asked for my forgiveness and welcomed me to the party, most of the others did the same.

Thinking about that night afterwards brought me to another realisation though. JJ was the main reason I was shunned in high school and bullied so badly. Despite that I could never actually hate him or even really dislike him because I had other feelings for him which had started the whole thing.

As I was developing and started to realise that I was attracted to other guys, it was JJ who caught my attention. He was the image of perfection to me, at least at that time. He was the stereotypical tall, dark and handsome jock, who had a killer body and a smile that could melt even the coldest heart. He was everything I had ever dreamed off and most nights he was who I dreamed of and jerked off thinking about. I wanted him so badly it was almost hard to explain. Little did I know that when I tried writing my feelings for him down on paper that someone would find it, give it to him, and then from there I would become a laughing stock for pretty much the entire school because of my uncontrollable feelings for him.

JJ himself was never actually too bad with the taunting and bullying. Sure, he never said a word to stop it and would often join in, but mainly he just seemed to go along with what others were saying or doing, possibly just to save face and appear cool to keep his spot at the top of the school. I think that’s why I loved him so much. Not only was he stunningly beautiful and sexy as hell, he actually seemed to show just the hint of a big heart beating beneath that gorgeous chest of his.

Even when he was part of the crowd who were treating me like crap and making me feel like dirt, sending me home at the end of the day to cry myself to sleep, I would still imagine it was JJ in my arms when I would hug my pillow as tight as possible. I often found myself stroking my hard cock as it started to get thicker with age to the idea that one day I might actually get the chance to be with him.

When high school finished I was so relieved to finally be out of the place where I had been forced to go every weekday to be tortured and tormented. At the same time though I was also a little devastated because I knew it would mean I wouldn’t get to see JJ in the halls everyday. He wouldn’t be in classes for me to stare at when I got bored or take a sneaky look at in the changing rooms, even though I was terrified I would get caught and beaten so badly I would never be able to look at another guy again.

That summer was so lonely and terrible with all the thoughts going through my head that college became my main focus, dreaming about how amazing it could be. Not once though did I ever think it would be as good as it has become. I have an amazing boyfriend, some kick ass friends, who are smoking hot, and now finally, after all these years, I’m actually becoming friends with JJ.

At the party I didn’t know if it was all a show, but when he actually wanted to keep in touch I was more optimistic. We didn’t really get too close because I think he thought I was full of shit any time he would ask how things at college were and I would tell them about life at the dorms and everything that goes on.

That all changed when he actually visited the college though and saw that it was all true. I don’t know if it made him like me more, or even envy me, but I think in a strange way it made him actually respect me, and as friends, that brought us closer and we had an amazing time.

He had sent me a message asking me if I was going home for Thanksgiving and I told him that I was and that I would be alone because Matt was going to spend the holiday with his mom. Hearing that, JJ invited me to a little party he was having at his and I gladly accepted when I heard that he hadn’t invited Ben and Freddie who had kicked off at that first party.

The party itself was great. No one treated me any differently, in fact, without Matt at my side I think they accepted me more because I wasn’t the gay guy who was at the party with his boyfriend, I was just Corey. They were talking to me, laughing with me, dancing with me, and they were enjoying themselves. At the end of the night I got hugs and kisses from most of the girls and handshakes or fist bumps from most of the guys. I couldn’t stop smiling.

When there were only half a dozen people left at the party I found JJ and helped him start to clean the house so his parents wouldn’t know there had even been a party when they got back in to town the next day. By the time we had finished we were the only two people left in the house so JJ offered me a beer to celebrate.

“I’m not sure I should drink another or I might not make it home,” I laughed.

“Just stay here,” JJ said, taking my hand in his and wrapping it around the beer bottle. I felt a little jolt of electricity when he touched me.

“Are you serious?” I asked

“Sure. We’ve got a spare bedroom. You might as well make the most of it.”

“Cool. And you don’t mind people knowing that a gay boy stayed at your house overnight?” I said, studying his expression.

He let out a long sigh. “How many times do I have to tell you that I don’t have any problem with you being gay, Corey? It doesn’t bother me in the slightest.”

“It did in high school,” I protested.

“People change, Corey. And things were different then…”

“How?”

“They just were, okay?” JJ said, turning away from me.

I followed him as he walked into the living room. I sat down beside him on the floor.

“How can you go from hating me to liking me?” I asked, genuinely intrigued.

“Because I let stupid ideas and stereotypes cloud my judgement and treated you like I thought I should. I never stopped to consider that you were still a person with thoughts and feelings like the rest of us. Now I do and I am truly sorry for the way I treated you,” JJ said with emotion clear in his voice.

“I know you are. I’ve already forgiven you, but the look in your eyes says there’s more to it than that.”

JJ took a deep breath and closed his eyes before he turned his head and looked straight at me.

“I’ve never so much as looked at another guy, Corey. Ever. But when I read what you wrote about me… your feelings for me… how you loved me and wanted me… it made me think things I shouldn’t have been thinking.”

Without breaking eye contact, I replied, “Are you trying to tell me that you thought about the two of us being together?”

JJ was silent for the longest time, just looking at me, until he finally spoke. “I’m not gay in the slightest, Corey, and I’ve never thought I was… but yes… I had thoughts and maybe even feelings for you when I first found out. No one had ever expressed feelings like that for me before. I started to wonder what it would be like to give in and let you have what you wanted.”

“Fuck…” I breathed, unable to believe what I was hearing.

“It was one of the reasons I started treating you worse than I maybe would have liked. I figured if I kept pushing you away and made you hate me then there would never be a chance of anything happening.”

“Did you think there might have been a chance in the first place?” I asked, stunned.

“Yes. I used to think I might crack one day.”

“Crack how?”

“I used to see you walking down the hall at school and you would look at me and I could tell you wanted me. It made me hard to know you had the hots for me and I guess I was worried that one day I might just snap and throw you up against one of those lockers and fuck your brains out.”

“Holy shit…” I said, my mind almost exploding with his revelation. “If I’d have known that I so would have come on to you!”

JJ laughed. “I bet you would have. You’d have done everything you could to get my cock in your tight ass.”

“Hell yeah I would,” I laughed too, feeling my dick grow in my pants with the conversation.

“You really wanted me that bad, huh?” JJ asked, taking another swig of his beer.

“Oh man, you have no idea. Every time I saw you I wanted to kiss you. I wanted you to take me in your arms and just hold me. But I think the thing I used to want you to do the most was just fuck me. I didn’t care if it was rough or not, I just wanted you to fuck me senseless, to fill me so full of your dick and make me feel so good that no other man would ever be able to live up to you.” I said, shocked that the words coming out of my mouth were the truth.

“Shit, man,” JJ said, moving his hand down to reposition his cock, which was clearly at least semi-hard in his jeans.

“You turned on?” I asked with a smile.

“How can I not be? Any time you hear how someone wants you to fuck them it gets you hard and horny.”

“True. Usually just seeing Matt has that effect on me.”

“You really love him, don’t you?”

“I do.”

“I envy you for that.”

“JJ, can I ask you something?”

“Yeah, shoot.”

“If I had come on to you in high school and made it known I would have happily let you fuck me… would you have?”

“Would I have fucked you?”

“Yeah.”

JJ was silent, thinking it over in his head. “You know what?” he finally answered. “I think I would have.”

“DAMN!” I shouted.

“What?”

“I can’t believe I missed out on you fucking me. If I’d have known that I totally would have done everything I could to end up in your bed. It was all I ever wanted back then.”

“Really?” JJ asked, sounding genuinely surprised.

“Yeah. I always wanted you to be my first.” I said truthfully. “Can I ask you another question?”

“Sure.”

“Did you ever fool around with any of your buddies?”

“What?” JJ almost shrieked. “Are you fucking kidding? I wouldn’t go near those ugly fuckers.”

I laughed. “But you would have gone near me?”

“Yeah,” JJ said. “I knew you wanted it and I was curious about what it might be like to give it to you.”

I was flattered, but I was also overcome with lust and desire. “Are you still curious?”

“What?” JJ asked, not moving a muscle but just looking into my eyes.

“Do you still wonder what it’s like to be with a guy? Do you ever find yourself curious about why I love being with Matt so much?”

JJ still didn’t move.

I decided to press on, slowly. “Because, you know… if you are curious… as a one night only deal… maybe we could do what we both thought about doing in high school.”

When JJ finally moved and blinked, he asked, “Are you serious?”

“Yes,” I said softly, moving a little closer to him.

“I’ve never so much as thought about being with another guy, Corey,” JJ said quickly.

“I know… This is just to satisfy that five year old curiosity that’s always in the back of your mind.”

“Shit…” JJ breathed.

I moved closer still and put my hand on his thigh. “I won’t do anything you’re not comfortable with. You’ll be in total control.”

“For real? You won’t try to get me to suck your cock or let you fuck me?”

“No. All I’ll do is show you what one man can do for another. You can shut your eyes and imagine a girl is doing it to you,” I said as I ran my hand up his leg until I had my hand wrapped around his jeans covered cock, which throbbed under my touch.

JJ threw his head back and moaned as I squeezed his shaft, but I took my hand away and he turned to look at me.

“How did that feel? Any different to a girl’s hand?” I asked.

“Fuck… That felt so good. Maybe better than a girl’s hand,” JJ breathed.

“And does this feel any different than a girl?” I asked, moving my hand to turn his head, leaning forward until our lips met.

JJ’s eyes went wide but he didn’t pull back. I didn’t try to force the kiss, I just pressed my lips against his and then pulled back.

“Fuck!” JJ screamed before grabbing my head and kissing me hard, his tongue demanding entrance to my mouth.

I let him inside and we kissed passionately, his hands holding my head while mine ran down his body until I had his dick back in my grasp.

When JJ finally broke the kiss he was almost out of breath. “Fuck… you’re an amazing kisser, Corey. Let’s take this to my bedroom.”

I won’t lie… I nearly shit myself when I heard those words. Never in my wildest dreams did I ever think my ultimate high school fantasy of getting to go up to JJ’s room to kiss him and suck him would ever come true, but that’s exactly what was happening. My dick almost exploded on the spot.

JJ stood up, repositioning his hard cock in his jeans as I quickly followed him out of the living room, up the stairs and into his bedroom. When the door closed behind me we both stood nervously just looking at each other. I wasn’t sure exactly how far JJ wanted me to go and I think he was unsure about what I might try to do to him, but I just wanted him to be comfortable.

When he didn’t make a move, I decided I would get things started so I pulled off my shirt and threw it to one side.

“Fuck…” JJ said, looking at my muscular body.

“What?” I asked.

“You’re so fucking built. I’m kind of embarrassed to take my top off.”

“Why?”

“I used to look like you in high school but since I’m no longer playing sports in college I’ve kind of let myself go.”

“I’m sure you’re still hot as hell,” I said, smiling and trying to make him feel better about himself.

Slowly he reached down and pulled his shirt off over his head. As his body was exposed I took the time to admire it. He was right, he wasn’t as built as I was, or as built as he had been in high school, in fact some of the bulk he had in his days as a jock had turned a little flabby, but he was still hot.

“You’re still unbelievably sexy,” I said.

“Really? Ever since I saw you at the party I’ve been hitting the gym again, but it’s going to take a while for me to look how I want.”

I could hear uncertainty in JJ’s voice so I decided to push his boundaries and walked over to him, placing my hand on his chest so that I could trace the muscles that were still quite hard, though they had definitely softened from the guy I used to admire in the changing rooms.

He took a deep breath when I touched his skin and moaned when my index finger ran over his nipple. I leaned down and took one into my mouth as I worked my hand down over his soft, smooth stomach.

I moved my lips up his body until I was kissing his neck and then he turned his head slightly so I moved up further until we were back to kissing each other. His hands were on my back, holding me close and feeling up my muscles, clearly impressed. My hands dropped down to his jeans to undo the button and pull down the zip.

Reaching my hand in to his jeans I squeezed his hard cock, causing him to moan in my mouth as his dick throbbed in my hand. I broke the kiss and started travelling south, moving my lips over his chest and belly until I was kissing up and down the length of his cock, which was still encased in his jeans.

JJ’s hand went down to my spiked hair to encourage me to continue. I got down fully on my knees in front of him and took hold of his jeans, pulling them down, along with his underwear. He stepped out of them and I found myself looking up at the naked form of the first guy I ever had feelings for. My dick was leaking more than it ever had before. It was all so hot.

I ran my hands up JJ’s thick thighs and moved in so my nose was under his balls, taking in the scent of pure man. Any doubts I had quickly disappeared as I snaked my tongue out of my mouth and started lapping at his balls.

His moans drove me on as his hand gripped my hair and tried to pull me upwards to work over his cock, but I was going to take my time and really make him love it. I rolled each of his balls around in my mouth and got them good and wet before slowly tracing the tip of my tongue up his entire shaft.

“Fuck!” JJ screamed, shuddering as my tongue licked a drop of precum from the tip of his cock.

“How does that feel?” I asked.

“Shit… it’s already the best blowjob I’ve ever had.”

I laughed. “I haven’t even started yet.”

“Fuck…” JJ breathed as I took the head of his cock into my mouth and started swirling my tongue around it.

His dick was exactly how I pictured it. It was about 7 inches fully hard and was a nice thickness, though not quite as thick as my own dick.

I started bobbing up and down, trailing my tongue along his shaft and around the head when he suddenly pulled me off his cock and moved back a few feet, sitting down heavily on the bed.

“Sorry, but you’re working me over so good I’m finding it hard to stay on my feet,” JJ said as he reached forward, put his hand on the back of my head and pulled me toward his glistening cock. He really wanted it now.

I got back between his legs, running my hands up and down his thighs as I took him back into my mouth and slowly went deeper; using all the skills I had developed with Matt, until my nose was in the dark pubes the same colour as the hair on his head.

“Holy fuck!” JJ yelled as he gripped my hair and threw his head back. “No one has ever deep throated me before.”

I pulled off his dick, making sure he felt my lips and tongue travel up his whole length. “Feel good?”

“I don’t have the words…”

I smiled and instead of saying anything in return I bent down again and swallowed him whole once more, using the muscles in my throat to really work the head of his cock. I could feel his thighs shaking beneath my hands.

I pulled off completely again and deep throated him a few more times before he pulled me up off his cock and lifted me up onto the bed. His lips attacked mine so hard, in a kiss more passionate than I could ever have imagined I would get from him.

“That was amazing, Corey, but I was about to blow. You’re not kidding when you said a guy knows how to get another off. My dick has never felt so good.”

I smiled and kissed him again. “I haven’t finished yet, either. I’ll get back down there and show you what my mouth can really do.”

JJ looked hesitant.

“What is it?” I asked, worried we had reached the end of our play time.

“Well… it’s just… as good as that blowjob was, this is the only time I ever intend to be with a guy and I was kind of hoping I could fuck your ass.”

“Really?” I asked as his words echoed around inside my head.

“Yeah. I’ve heard it’s much tighter than a pussy but none of the girls I’ve been with would let me fuck them up the ass. So what do you say?” JJ asked, looking almost scared.

“I don’t think you realise how many times I dreamt of this moment in high school. Every night I used to think about being in your arms and feeling you slide your dick inside me. Actually getting the chance for that to happen is almost more than I can handle. Here, feel this…”

I took JJ’s hand and slowly moved it down to where my cock was straining against my pants.

“Fuck. You’re rock hard.” JJ said.

“I know I am. That’s how much I want this. Fuck me, JJ.”

The smile on JJ’s face when I said that almost made my heart melt. The guy really was incredibly attractive and I could see exactly why I had fallen for him in high school. I leaned back in to kiss him, slipping my tongue into his mouth as he moved his hands to cup my ass.

When we broke the kiss JJ flipped me onto my back on his bed and pulled my pants and boxers off so I was naked beneath him. He pulled me to the edge of the bed and looked down hesitantly. He reached out his hand toward my cock but I saw his hand shaking almost violently as he moved it closer.

“You don’t have to jerk me off or suck me if you don’t want,” I said, seeing his reluctance.

“Are you sure?” he asked, moving his hand back. “I feel bad for not getting you off too.”

I laughed. “If you fuck me right, believe me, I’ll get off in the greatest way.”

JJ looked at me for a moment to see if I was being serious and then a huge smile broke out on his face, which I returned. He walked over to his bedside drawer and pulled out condom and a bottle of lube.

He threw the bottle to me and I did what I needed to in lubing up my ass. I was already clean from a little pre-party dildo play after a slightly naughty conversation I had on the phone with Matt.

I watched as JJ rolled the condom down over his hard cock. It looked so hard and I could see one of the veins running up the side of it throbbed as his blood pumped through it. When he took the lube from me, applying it to his cock he never broke eye contact and it was so intense.

“How do you want me?” I asked.

“On your back,” he said without hesitation. “I want to see your face when I fuck you.”

My whole body shivered hearing those words from him. I’m not sure my cock had ever been harder. I had been involved in many hot moments with some amazing guys but this sex was five years in the making and I never wanted anything so bad. I couldn’t wait to get his cock inside me.

I raised my legs and JJ stepped up between them, using his hand to aim his cock at my well lubed hole. There was no teasing, no rubbing his cock against my hole or slapping his dick on my ass, he just leaned forward and shoved in, burying himself inside me with one swift thrust.

I screamed out and he stopped for a moment, a look of worry on his face.

“Oh fuck, that was intense,” I panted, trying to catch my breath. “Give me a second and then fuck my brains out, JJ.”

“You sure you can take it?” he asked with a devious smile.

“Hell yeah I can take it. Fuck me like you would have done all those years ago.”

“Yeah?”

“Yeah. Just imagine you’d snapped one day and let all your emotions out.”

“You got it, Corey,” JJ said, pulling out of me. “You want my cock, gay boy?”

“Oh yeah, fuck me!” I screamed, playing along.

Once again JJ plunged his dick in to me, making me scream and moan again. He got closer to me and pushed my legs back, leaning over me until he was right in my face, his breath felt hot against my cheek.

“So you want this dick to fuck you do you? Make you a whore like all those cheerleaders I’ve fucked?” JJ said through gritted teeth, totally getting in to character which just had me hotter than ever.

“Yes! I’ve never wanted anything more in my life. Fuck me you big stud jock!” I screamed back in reply.

JJ laughed at that but he started to move his hips to pull his dick out of me and then thrust back in. He wasn’t gentle in the slightest, but I didn’t want him to be. He wasn’t hurting me in any way, but the adrenaline that was pumping through me with the little role play had me so hot and hard I could barely contain myself.

With my moans of pleasure JJ picked up the pace, almost folding me in half as he started to really thrust hard in to me, pounding me deep, making me feel every inch of his cock. It was incredible. It was actually exactly how I had imagined it would have been back in high school.

On a deep thrust JJ hit my prostate and I yelped so loud I think he thought he’d hurt me so he pulled back and stopped thrusting, looking at me to see if I was okay.

“Keep fucking me like that, that felt so good!” I said, pulling him deeper into me.

JJ smiled and pushed my legs apart, bending over until his lips were on my neck. His hips started thrusting back and forth again, drilling his hard cock in and out of me and he nibbled on my neck and then started biting me.

“I’m marking you as my bitch. You love my hot, hard cock, fucking your tight little ass, don’t you?” he said between bites.

I grabbed the back of his head and pulled him closer in to me. “I fucking love it. Fuck me harder!”

JJ growled then and pulled his cock out of me. He flipped me over so I was on my hands and knees, pulled my ass until it was hanging over the edge of his bed and plunged his dick back inside me.

I grabbed on to the sheets at the force of his re-entry and then the pleasure that overwhelmed me as every thrust sent the head of his dick crashing in to my prostate. I knew JJ hadn’t fucked a guy before but damn was he a natural.

I arched my back and pushed my ass back on to him, wanting more of him inside me. Suddenly he grabbed me by the hair and pulled my head back, leaning in to whisper in my ear.

“You’ve wanted this cock so bad for so long, haven’t you, bitch?”

“Yes!” I screamed.

“You like it fucking you HARD?” he asked, emphasising the last word with his most powerful thrust yet, which forced me up onto the bed.

“Yes! I fucking love it! Fuck me, JJ! I’m about to cum!”

JJ suddenly wrapped his arms around my chest, thrust his entire dick into my ass, placed his lips on my shoulder and reached around, grabbing my dick. With just two quick strokes my load fired out of my cock. Each shot was so powerful it landed on the other side of the double bed.

I could barely breathe my orgasm was so intense. I didn’t realise it but my ass must have really been squeezing JJ’s cock because he screamed himself, pulled his cock out of me, threw off the condom and came up my back, spraying me with a massive load.

JJ then collapsed down onto the bed and I could see the last few drops of cum leaking from his cock onto his stomach so I leaned over and took his cock into my mouth, cleaning it off and licking up the spilt cum. Damn did it taste good.

It was only when his cock became too sensitive that JJ pulled me off his cock and up into a long, tongue-filled kiss.

“That was the greatest fuck of my life,” JJ said, pulling me back in fir a kiss,

When we broke the kiss, I put my head on JJ’s chest and he threw his arm around my shoulder. We fell asleep like that and I had such a warm feeling inside knowing that finally, after so long, JJ had actually fucked me.

THE END!!