ROOMING WITH MY BEST FRIEND - NOW OR NEVER



This is a fantasy chapter written by Big D. While the beginning of this chapter is taken from Sophomore Chapter 52, where the chapter goes after that point is pure fantasy and did not really happen in any form. Again… THIS DID NOT REALLY HAPPEN.

Posted:   January 21, 2012



Once we finished our workout in the Rec, Shawn and I raced back to the dorm. I did see Corey for a moment but he was busy so I didn’t want to bother him. Shawn entered the room with me. We downed the mix of whey and protein after a really great workout. 

“Matt, don’t you just love how all the work we’ve put in is really showing?” Shawn said.

“I do. Before you met me I was pretty thin.”

“I know what you mean there. Damn now I have a chest, shoulders and abs. It feels so good.”

“It does,” I smiled at him. “Hate to change the subject but I was wondering if you’ve heard from or even seen Terra?”

“I ran in to her yesterday matter of fact. It was friendly, but we’re done. She really needs to find someone that can live with her ways. Not that they are bad, but they aren’t for me at this time in my life. You know that college is for spreading your wings and exploring life,” he said.

“It is that.” I said with a smile but I noticed Shawn suddenly go quiet. “What is it?”

I kept my gaze on Shawn as it seemed he wanted to say something but couldn’t form the words. I remained quiet, just watching him, until he finally spoke.

“Thinking about spreading my wings and exploring life has got me considering things I never thought I would,” Shawn said, lowering his head.

I stepped up to him and put my hand under his chin, lifting it until he was looking into my eyes. I spoke softly, “what are you considering?”

“This…” Shawn said, without really saying anything.

“I don’t know what you mean,” I said, still confused.

Shawn again looked like he was trying to form words but none would come out of his mouth. Eventually he let out a big sigh, pushed my hand away from my face and took my head into his hands. Before I knew what was happening Shawn’s lips were on mine and he was pushing his tongue into my mouth.

I was so shocked that it took my brain a moment to realise what was happening. When it finally registered the kiss was starting to feel good and even though my head was telling me to stop and push him away, the growing dick in my pants and the feel of his new, straight boy lips touching mine made me give in.

Shawn had obviously not been getting much action from Terra even before they broke up because he attacked my lips with such passion and energy, like he was a hungry man who had finally found the one thing he desired most.

As suddenly as the kiss had started, it ended. Shawn pulled back from me with a smile on his face. I used my tongue to lick my own lips, which were a little sore but Shawn’s kiss had really got my blood flowing and I was so excited.

“I’m sorry, Matt,” Shawn said, panting.

I shook my head, “Don’t be. That kiss was fucking awesome.”

Shawn smiled, “Thanks. But I really shouldn’t have kissed you. Talking to you just then about exploring life just got me to thinking about Kris and Colt and how they’re exploring life with each other and with you. Hell, Bryson even admitted to sucking Kris’ cock and getting fucked by Colt when he was drunk one night. I’m about the only guy who hasn’t experienced sex with another guy and I’ve been thinking about it for a while. I never thought I would do it and actually the thought made me a little queasy, but being here alone with you, especially after that hot kiss, is making me want to try it.”

I was stunned. Shawn had never once even hinted at having gay thoughts before and here he was admitting that he might want to fool around with me.

“Do you seriously want to do this?” I asked to be certain.

“It’s a case of now or never,” Shawn said.

“Okay then,” I said. “Since we’re alone, and will be for a while, if you want to fool around right now then I am more than happy to.”

“I’m a little nervous,” Shawn admitted.

“Do you trust me?” I asked.

“Yes,” Shawn answered immediately, without even having to think, which made me smile.

“Then here’s what we’ll do. I’m up for anything you want to do with me, but you are in complete control, okay?”

“How do you mean?” Shawn asked, raising an eyebrow.

“I mean I’m your slave right now. You can ask me or tell me to do anything and I’ll do it, but you have to give the command or I won’t do anything. I want you to be totally comfortable with what we do together.”

The smile that spread across Shawn’s face was the biggest I had ever seen from him. His beautiful eyes sparkled and he moved his hand to the back of my head and pulled me into another hot, tongue-filled kiss.

Since Shawn’s lips were pressed against mine, his tongue exploring my mouth, he couldn’t give me my next command so I decided to test the waters a little, moving my hand down to the bottom of his shirt and then slowly slipping it underneath until my skin was against his.

I felt Shawn’s body shudder and he moaned into my mouth as I started to run my hand over his muscles, tracing his developing abs with my fingers, slipping one inside his belly button and then moving up to the small, but hard pecs, giving one of the nipples a tiny squeeze, causing Shawn to yelp and pull me even harder into the kiss.

I continued working his body for another few minutes all the while we continued to kiss. With our lips still locked I felt Shawn’s hands finally move from my head. He placed one on my hip and the other on my shoulder. The hand on my shoulder slid down my back and I heard him moan, only for him to moan even louder when he moved the other hand to my ass and I tensed the muscles, trapping one of his fingers as it passed across my crack, even though I still had my pants on.

I couldn’t take it any more. Not only did I need to catch my breath from the incredible kisses. My mouth literally felt like it was on fire. I pulled back from Shawn’s lips and almost ripped his shirt off, tossing it to the floor.

My breathing was ragged and I was panting like a dog but I was so turned on as I bent down and started planting kisses across Shawn’s hot chest. The time at the gym, working out, was really doing wonders for him and I savoured the feeling of his hard pecs against my lips and tongue.

My fingers traced the abs that became more defined with each day. Shawn was more reserved than some of the others, especially Kris and Colt, so I didn’t often see him naked, but fuck me he was hot, just like all my friends.

I moved my tongue down to work on Shawn’s abs, running the tip around each one. Shawn was moaning, his hand grabbing on to my hair and holding on tight even though he didn’t force me to do anything. As I moved back and forth I could feel his hard dick pressing against his pants as it came in to contact with my shoulder.

I was about to reach down to unzip his pants but I felt Shawn tug on my hair and allowed him to pull me back up until we were face to face. He kept hold of my hair as he pulled me back toward his lips for yet another deep kiss.

This time when he broke the kiss he grabbed the bottom of my shirt and started pulling it up. I lifted my arms and let him get it completely off me before he just stood staring at my body.

When he didn’t move, I spoke, “are you okay?”

“Yeah…” Shawn replied. “I just… It doesn’t feel right for me to do to you what you just did to me.”

I smiled. “Then don’t. I told you I wasn’t going to make you do anything you didn’t want to do. I’m happy to be completely submissive for you, so what do you say we move to the next step?”

Shawn’s smile said all I needed to know, but his nod confirmed it. I dropped to my knees in front of him and looked up into his eyes as he glanced down at me and gave another nod.

I reached out and ran my hand up and down the hard cock that was pushing against his pants. I knew Shawn’s dick wasn’t the biggest, but as I ran my hand along the shaft it felt rock solid and pretty damn thick, I couldn’t wait to get my hands on it.

When I got the button undone and the zip unfastened I pulled Shawn’s pants down and he stepped out of them, kicking off his shoes too. I looked back at the bulge in his boxer briefs that hugged his body and his package really tight and felt drool running down my chin, probably in similar quantities to the precum flowing out of the tip of Shawn’s cock, soaking the material.

I licked my lips and leaned forward pressing them against the shaft of his hard cock. I kissed up and down the length of it until I finally reached the head and tasted some of Shawn’s precum. Fuck! It was delicious. I dove in and started sucking at the material and the head of his cock, trying to suck up as much of his juices as possible.

Shawn was moaning, goosebumps all over his body and his grip on my hair tightening as I continued to suck on his wet patch. His precum was so sweet, with just a hint of that usual salty taste. I couldn’t get enough.

When I felt I had sucked as much out of the boxer briefs as possible, I pulled them down, exposing Shawn’s throbbing cock. I leaned back to fully appreciate the view. Shawn’s dick was maybe only five and a half inches long, but it had a perfect upwards curve to it that made my ass twitch, thinking about what it could do inside me. And it was thick. Seeing Shawn hard was a rarity but his dick really plumped up. It might have even been thicker than Corey’s. Now I was really excited.

Shawn kicked off his boxer briefs and stood completely naked in front of me. He placed his hands on his hips and used his muscles to make his dick twitch and jump in front of me. A drop of precum formed on the tip, threatening to drop to the floor so I quickly leaned in and licked it from the tip of Shawn’s cock. He moaned and I felt another drop leak onto my tongue.

I pulled back and lowered my head, burying my nose just beneath Shawn’s balls. I took a deep breath and was hit by such a hot scent of a man. The smell was a mix between soap, sweat and pure sex. He was more than ready for what was to come.

Extending my tongue I began lapping at Shawn’s balls. They were quite big, clearly loaded with the spunk he hadn’t shot for quite some time, even though I was sure he must jerk off regularly. I sucked on the slightly hairy globes, my own dick throbbing hearing the moans escaping Shawn’s mouth.

As I continued to suck on Shawn’s beautiful balls his hard dick was resting on my face, rubbing against my forehead, leaving a trail of precum over my skin. I couldn’t take it any longer. I ran my tongue along his shaft and then swirled it around the head of his dick.

He moaned and grabbed hold of my head, pushing his dick into my mouth until my lips were pressed against the base, with my nose in his trimmed pubes. The length of his cock meant I had no problem fitting it all the way in until the head was poking at my throat, but I was surprised that I actually felt my lips stretching a little at his thickness, he was definitely equal to Corey, maybe slightly thicker.

Shawn didn’t even pretend to play around. Both hands were on my head and he started moving his hips back and forth, gently fucking my face. I just placed my hands on his thighs and opened my mouth wide, letting his dick slide over my tongue as I sucked on the hot cock as it started to piston in and out of my mouth.

I started running my hands up and down his thighs, which were covered in a fine dusting of hair, occasionally reaching up to pull on his balls. When I did that he moaned and pulled my face hard against his crotch, impaling my mouth on his cock.

I couldn’t remember the last time a guy had treated me like Shawn was doing. He was totally using me as a tool to get off and I have to admit, it was hot as fuck. He was being very commanding but at the same time he was very gentle. He wasn’t hurting me, it was more like he was guiding me along and making sure I moved at a pace that meant he felt the most pleasure.

“Fuck, Matt,” Shawn breathed. “You are such a pro at sucking dick. All that time with Corey and the others has done wonders for you. No girl has ever sucked my cock like you. You’re amazing.”

I smiled around his cock hearing him gush, but suddenly it wasn’t enough, I wanted more. I forced myself off his glistening cock and looked up at him. “I love sucking your dick. It’s so hot. But if you think my mouth is good, wait until you feel my tight ass wrapped around your cock.”

Shawn shuddered and for a split second I thought I had gone too far with my words but then I saw his cock twitch and a smile spread across his face. He reached down and pulled me up to my feet, gripping me tight and once again attacking my lips with his.

As the kiss continued I felt Shawn’s hands move as he became more comfortable and adventurous. They had started half way up my back and slowly slid down until they were teasing the waistband of my pants.

With Shawn’s tongue in my mouth, exploring every inch and tasting his own precum inside me, making him kiss me even harder and with added force, I reached down and undid my pants, letting them fall to the floor. The moment they hit the ground Shawn made his move.

I was surprised by how excited he was and how far he was going. I knew he wouldn’t be sucking my big cock or getting fucked by it tonight, but the way his hand slid into my boxers and his fingers started playing with my asshole was definitely a shock.

Shawn then brought one of his hands up to my face and pulled back from the kiss, replacing his tongue with his finger. I got the hint and started sucking on it like I had been on his cock just a minute earlier.

Once I had the finger nice and wet, Shawn moved it back down until it was teasing my opening, putting just a little bit of pressure on it. Then in one swift movement he buried the finger inside me and I jumped, throwing my arms around him and pulling him tight against me, burying my face in his shoulder to muffle the scream.

Because I wasn’t expecting the sudden invasion, my body shivered and my ass clenched around Shawn’s finger. He moaned in my ear.

“Fuck that’s tight,” he said, pulling his finger out of me. “I’m sorry, Matt, but I can’t wait. I need to fuck you now.”

My mind was spinning and my body was overwhelmed at the assertiveness of Shawn and how he was controlling me. The weirdest thing was that I actually enjoyed it. I loved having him basically tell me what to do, or I guess more accurately, what he was going to do to me.

Shawn took a tight grip on my wrist and dragged me toward my bedroom. My heart was pounding so hard and adrenaline was surging through my body that I was tingling all over. I didn’t even have to think about anything because my mind just took over and it was like I was on auto pilot.

I headed straight for my drawer and pulled out the bottle of lube and a box of condoms that we kept in there. Corey and I might fuck bareback every time, but since we had opened up our relationship a little, allowing us to experience the joys of sex with our friends, we made sure to have condoms that would fit both of our dicks. I grabbed the condoms Corey liked to use and tossed one to Shawn.

He ripped it open with such enthusiasm and rolled it down his throbbing cock, watching as I poured lube into my hand and started pushing a finger into my ass to get it ready for his dick.

I worked three fingers and a load of lube into my ass and then climbed up on the bed on my hands and knees, pointing my hole in Shawn’s direction. I heard him take a deep breath, maybe even a gasp and then heard a few footsteps as he moved over to me and stood so close behind me I could feel his body heat against my ass cheeks.

Then I felt the wet lube hitting my ass and I looked over my shoulder to see that he was pouring it on to his covered cock directly over my hole so that any that didn’t fall on his throbbing dick landed on my ass. He wanted me ready and I could tell by the look on his face how eager he was. This was not going to be slow and he wasn’t about to make love to me. It was going to be a hard, rough fuck and I couldn’t wait.

The next thing I felt was Shawn’s hand on my ass, using his fingers to part my cheeks as he used his other hand to point his dick straight at my hole. My eyes were focused on his as they looked down at my ass with more concentration than I have ever seen in anyone’s eyes.

When he finally pushed forward, the head of his cock first kissing my hole and then pushing harder until it really stretched me open and began to sink inside, I buried my face in the mattress to muffle the moans that rose up from my chest and escaped my lips as I bit them.

I wasn’t in any pain because I was so used to taking Corey’s thick cock inside me, but even with Corey there is always the near shock of penetration when you feel yourself opening up beyond your normal limits to accept another guy in to you and Shawn was definitely testing those limits.

Unlike some of my other lovers over the years, who paused to allow me time to adjust, Shawn just ploughed forward, burying himself fully in my ass. The air was completely driven out of me and I gripped the sheets in my fists as my ass twitched and danced around Shawn’s cock as his balls came to rest on my cheeks.

I tried to tell him to take it easy, that my ass was different to the pussies he had fucked but the only sound that came out of my mouth was a long, deep moan.

Shawn pulled back until the head of his dick was the only part left in my ass as my muscles clenched, trying to grip on to his cock to stop it from slipping out. With a swift forward thrust Shawn then buried himself back inside me and as he did the slight upwards curve of his cock sent the tip crashing into my prostate. I screamed and arched my back, pushing my ass against him instinctively, wanting more of him inside me.

I had been fucked by longer dicks than Shawn’s, Corey had about an inch on him and Scott about two inches more than Shawn, but it really didn’t matter. With Shawn inside me I felt so full and as he pulled back and then drove his dick back inside me the head of his dick ran directly over my prostate again. His dick was perfect. It was like it was made to fuck my ass.

“Oh fuck, Shawn!” I screamed. “Fuck me, man, just fuck me! Harder!”

I heard Shawn moan as his hands moved to my waist and tightened around the skin, holding me tight. He slid his dick back out of me and then pulled my ass toward him and he plunged forward and started fucking my ass.

“Fuck yeah!” Shawn screamed in delight. “Your ass is so fucking tight. It feels so good around my cock.”

The grip he had around my waist held me tight against him and I was completely at his mercy as he pulled me back and forth on his cock. Every time the dick thrust in the head ran over my prostate, working my body in to a frenzy. I had never felt anything like it before as Shawn continued to pummel my spot. My whole body was tingling and I was short of breath.

Being on my hands and knees I was able to rock back and forth so I could rock forward as Shawn withdrew and then I push my ass backwards as Shawn pulled me toward him and impaled me on his dick.

We built up a nice rhythm and then slowly the pace grew quicker until Shawn was really pounding me. His balls were bouncing off my ass, our skin was slapping together and I was sure there would be red marks there, the telling signs of the powerful fuck I was currently engaged in.

As Shawn pumped his hips forward, driving his dick into me, I was caught completely off guard. I felt my stomach suddenly tighten and all of my muscles tensed up. I clung to the sheets with all my strength as my body shuddered, my ass clenched and my cock twitched. I threw my head back and screamed as my cock exploded with one of the biggest, most forceful loads of my life. The orgasm ripped through my body and I didn’t know what had hit me. It was incredible.

I had experienced a few hands free cum shots but nothing like that one. I could barely breathe. My chest was heaving, my abs felt so tight, and looked it when I glanced down to see them flex just above my cock, which was still leaking cum as Shawn continued to fuck me, assaulting my prostate.

Shawn continued to surprise me when he pulled his dick completely free of my ass. I thought the contracting muscles around his dick had brought him to the edge but that wasn’t the case at all.

With his grip still tight on my hips he flipped me over so I was on my back. He pulled me to the end of the bed, turned me slightly so I was just on my side and then lifted my leg up onto his shoulder. That position gave him the perfect angle for re-entry and without so much as a word he plunged his throbbing cock back into my ass.

I groaned as he stretched me again but there was no pain, only pleasure, and Shawn gave a great moan of satisfaction as my ass wrapped itself around his shaft. He pulled out of me completely again and then forced his way back inside, repeating the action five more times until I was yelping and whimpering each time he broke past my sphincter and sank balls deep in my ass.

Shawn was incredible. He started fucking my ass again, pulling on my leg to get more leverage as he drilled his cock into me. His abs tightened with each thrust, glistening with the sweat that was starting to form on his body, emphasising his muscles and making him look hotter than ever.

I was moaning in time to each of Shawn’s thrusts but when I looked up to see his eyes focused on me I noticed a look of concentration on his face. He kept his eyes on mine and then started moving his hips in different directions, changing the angle of his entry.

I kept moaning with each thrust until he hit my spot again with the tip of his cock and I yelped so loud I almost deafened myself. Shawn smiled and held me steady, remaining in the same position so he was attacking my prostate again. HOLY SHIT! He was an incredible fuck. His dick felt so good inside me.

After my first orgasm my cock had started to soften a little, though it was still semi-hard and probably still a bit longer than Shawn’s cock was fully hard, but as he started rubbing over my prostate again it returned to the full eight inches and precum was flowing out of the slit.

My entire body felt like it was on fire and I found myself needing to cum again. I clenched my ass around Shawn’s cock. He growled and started fucking me really hard, drilling my ass.

I reached down and wrapped my hand around my cock, smearing the precum over the head and down the shaft. I don’t think my dick had ever throbbed so hard in my life as I started to jerk it as fast as I could with Shawn pounding my ass.

“I’m close, Matt,” Shawn panted. “Cum with me.”

I didn’t think it was possible but Shawn started fucking me even harder, I almost thought I would pass out. My balls were tingling. The head of my cock looked like it was glowing. My ass was on fire.

Suddenly my breath caught in my throat and I gasped as my cock started firing ropes of cum across the bed. For my second load I was amazed at how powerful the shots were. I let go of my cock and threw my head back against the mattress, my eyes rolling up into my head as my dick continued to throb, sending more cum onto the sheets.

My ass twitched and clenched around Shawn’s cock, massaging it, milking the load out of his balls.

“Fuck!” Shawn screamed.

He pulled out of my ass, ripped off the condom and gave his cock two quick strokes before releasing a torrent of cum all over my ass. I could feel my cheeks being coated with the massive load that had obviously been building up for a while. His eyes were closed and his body shuddered as the final few spurts shot out of his cock.

As I was still recovering from my own orgasm Shawn took a few steps back and fell into the chair at my desk, completely spent.

I laughed, “How was it?”

“Oh fuck, man, it was incredible. I needed that,” Shawn smiled, giving his deflating cock a quick tug.

I smiled back at him but I was exhausted and just collapsed back onto the bed. I was covered in cum, as were the sheets, but I didn’t care. I had just been fucked by a great friend of mine, one who I never dreamed I would get the chance to be with, and it was great!

THE END!!

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