Rooming With My Best Friend - Now Or Never (Fantasy)
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.
NOW
OR NEVER
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 nearly 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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