Date: Mon, 16 Mar 2009 21:25:52 -0500
From: Barefoot Preppie <barefootprep@gmail.com>
Subject: My Roommate Derek - part 1

I set my fan up on the windowsill and turned it to full blast. It was over
90 degrees out, and I was in the middle of setting up what was to be my
dorm room for the next nine months. I'd made some good progress--sheets
were on the bed, my clothes were in the dresser, and I had my laptop up and
running--but there was still a lot of unpacking to do. For the time being,
I was content to put it off. There were other freshmen trudging through the
hall, boxes in hand, and part of me knew that I should probably help them
out in the interest of making new friends. But it was too fucking hot, and
I had the whole year ahead of me to make friends. I had long since peeled
off my T-shirt and thrown my ratty flip-flops in the corner, and now I
dropped my shorts and flopped on my bed in nothing but my white
boxers. Soaked through with sweat, they didn't leave too much to the
imagination, but I didn't really have to worry about modesty. Jackson,
after all, was an all-male college, and one of the last in the country, at
that.

I'm Trent Syler, by the way. I'm 18, from a small town in Michigan that
you've probably never heard of, and am first and foremost a ladies' man. Or
at least I was. Things at Jackson College would obviously be different. I
know you're probably thinking I'm crazy to go to an all-male school, and
I'll admit it was a difficult decision to make, but I couldn't turn down a
four-year scholarship. Plus, Jackson has a phenomenal athletic record
across the board. Though it's only a small private college, Jackson's
football, swimming, and wrestling teams are among the best in the state of
California--and the top in Northern California, no question.

The sultry air had become unbearably heavy, and I reluctantly rolled off
the bed and walked down the hall to the bathroom. The cool tiles felt good
against my bare feet, and I walked up to the nearest sink and splashed cold
water on my face. As I gazed at my reflection in the mirror, I surveyed my
soggy state. My dark brown hair was pasted to my forehead, and beads of
water rolled down my neck and onto my chest. I absent-mindedly rubbed a wet
thumb across my hard nipple and sighed. I worked out a lot back home, and
even though there weren't any girls here to impress, I was determined to
keep myself in top physical shape. I was admittedly
short--five-foot-six--but had a body I was proud of.

As I stepped back into my room, I immediately noticed a green backpack on
the opposite bed that hadn't been there before. Across the flap were three
white initials: "DRV."

 "Hey, roomie," came a voice behind me. I nearly jumped out of my skin, and
I spun around to see a tall, young guy standing in the doorway. He dropped
a box on the floor and laughed.

 "Dude, are you always this nervous? I'm Derek."

 "Trent," I said, shaking his hand. "Sorry--I guess I just zoned out for a
minute."

The first thing I noticed about Derek was that he was as undressed as I
was. He was barefoot and shirtless, wearing nothing but a hemp anklet and a
sagging pair of cargo shorts--and obviously no underwear. His light blond
hair looked ruffled--somewhere between short and shaggy--and his deep brown
eyes were piercing, almost black. But it was his body that made me
jealous. His hard pectorals and abs were ripped and completely smooth, save
for a fine blond treasure trail that ended in the light dusting of pubic
hair poking well above his sagging shorts.

 "Fuck, it's hot as balls in here," he chuckled. "Good call with the
fan. I've got one in the car somewhere."

"You need some help bringing your stuff in?"

"Well, I haven't got that much, but yeah, that'd be cool."

I picked my shorts up off the floor, and as I pulled them up, Derek reached
over and playfully snapped the elastic of my boxers.

"Dude, seriously?" he said. "Underwear?"

"Yeah, so what? Don't you ever wear underwear?"

He turned around and pulled his shorts down a bit, exposing a tan, hairless
ass.

"Never have, never will. Trust me--pretty soon I'll have you freeballing
too. You can't beat it."

I left my shirt behind and decided to walk barefoot down to the parking
lot, seeing as he was too. The pavement was scorching hot, and as I jumped
across the white lines, he ambled across the sizzling asphalt as if he were
on a Sunday stroll.

"So Derek, where are your shoes, anyway?"

He grinned as if he'd been expecting this.

"Now there's a question people only ask once. Don't wear 'em. Haven't once
in ten years. That's the first thing people learn about me--I'm always
barefoot."

He said it so proudly yet so matter-of-factly, and I was immediately
intrigued. We reached his car, a faded old Jeep Cherokee, and he began to
rummage around the back seat.

"You mean you don't even own any? Like, not even sandals?"

"Nope."

"So...are you like a hippie or something? You sure don't look the part."

He laughed.

"Fuck no. I just like having my feet bare. Always have."

"That's pretty cool, I guess."

"Yep. What about you--you go barefoot a lot?"

"Obviously not as much as you."

"Give it time. Hang around me and you will. Here--can you take this?"

He handed me a large cardboard box, grabbed a couple himself, and we headed
back into the dorm.

I stripped back down to my boxers and sat as Derek unpacked his
clothes. There wasn't too much to unpack--a couple sleeveless tees, one
button-down shirt, a torn pair of jeans, a few pairs of cargo shorts, and
some gym shorts. He wasn't kidding--no shoes, no socks, and no
underwear. It all fit in a single drawer.

"So, it looks like you work out," he said, setting his computer on his
desk.

"Looks like you work out more," I laughed.

"Thanks, man. We should hit the gym later. Oh--and there's a fitness room
at the end of the hall, too. Did you see that?"

"Yeah, but the gym is right by the pool."

"Oh no way, man--are you a swimmer, too?"

"Not really. I played lacrosse in high school."

"Cool, cool. I swam and I wrestled. You know--the sports you don't need,
like, shoes for."

He sat down at his desk chair, propping his feet up on a box. His soles
were fairly black from the years of dirt, but otherwise, his feet didn't
look too bad--tan, hairless, and pretty big, but that was no
surprise. Derek was probably about 6'1", 6'2". He grinned proudly when he
noticed me staring.

"Here, man," he said, sticking out his right foot and wiggling his big toe
at me. "Have a feel. Everyone's always curious."

I chuckled and ran my hands over the sole of his foot. It felt cool and
sandpapery.

"Ten years of callous," he said. "Pretty rad, right?"

"Awesome. I couldn't get away with being barefoot for that long."

He stood up and stretched lazily. His shorts sagged slightly lower,
exposing the base of what looked to be a pretty thick cock.

"Well, you just find people who are cool with it. No one gave me crap when
I went barefoot to school. My dad owns a gym, so I can work out however I
want to. If I need shoes on to get in somewhere, then fuck it--I'll just go
someplace else."

We continued to shoot the breeze for a few minutes. I learned that Derek
was from San Diego, and that he also came to Jackson on a scholarship. I
had figured he was from SoCal--a typical surfer dude.

"Aha, here we go," he said, picking up an electric fan. "Told you I had one
too."

He set it in the window next to mine and cranked it up.

"Good thinking," I said.

He closed his eyes as he faced the welcoming breeze, sighing contentedly.

"Dude," he said, "I think it's naked-time."

He grinned and pushed his shorts to the floor, kicking them under the bed.

Now, I was no expert on cocks, but Derek's was easily the biggest I'd ever
seen. It must have hung eight inches soft, not quite as thick as a beer
can, but close. It was lightly tanned like the rest of him, ending in a
large, helmet-shaped head with a wide piss slit. A dusting of cropped,
blond pubic hair surrounded the base, and I could see that his egg-sized
balls were shaved completely smooth.

"That's better," he said. "You're cool with this, right?"

"Sure. It's cool."

"I'm not really big on clothes, in case you hadn't noticed."

"Shit, I wouldn't be either if I had a cock like that. How big is that
thing?"

"Oh, this?" he said bemusedly, hefting his cock in his hand. "Ten inches
when I'm boned up. Well, ten and a half."

I shook my head and let out a low whistle.

"Yep, it keeps the ladies happy. How about you, buddy?" he said, ruffling
my hair.  "What's a little guy like you packing?"

"What...you mean you want to see?"

"Yeah, man. I mean, this is our room. Might as well keep it casual and go
bare-assed, right?"

I took a few seconds to think about it and shrugged. What little modesty I
had was about to go flying out the window.

As I reached for the waistband of my boxers, I suddenly remembered that the
door to our room was wide open.

"Uh, Derek--can we close the door first?"

"Why? Ashamed of what you got?"

"No...but I haven't met any of our hallmates yet, and I really don't want
them to see me waving my hangdown at you."

Derek scratched his balls and laughed.

"Yeah, that'd be one hell of a first impression," he said. "OK. Close it if
you want."

I casually shut the door and peeled off my boxers, tossing them onto my
bed. My cock was soft, but swollen from the heat. It wasn't all that tan
like Derek's was, but it was pretty thick and ended in a nice mushroom
head. I'd left my pubes natural and untrimmed.

"Whoa, Trent, nice piece. How big does that get--like, seven inches?"

"Eight."

"On a short guy like you? Damn. Does that ever surprise the bitches?"

"Used to," I said. "But word gets around."

"Fuck yeah. I'll bet you're a real player, too, with a big one like
that. I'm the same way."

Feeling more comfortable with my nudity, I sat on my bed and leaned against
the wall. Derek sat on the mattress opposite me, and we just talked like
that for awhile, totally naked. It was kind of cool. I mean, I'd been naked
around my friends in the locker room and the hot tub, but this was
different. Here, we were just naked for the pure enjoyment of it.

Derek mentioned that he had a longtime girlfriend, Veronica, and I asked if
he was going to miss her.

"No more than I'm going to miss any other piece of pussy," he said. "We're
not exactly exclusive. How about you--you got a girl back home?"

"Used to. We broke up over the summer."

"Ahh, OK. So you must do a lot of this then," he said, grabbing his cock
and yanking it a couple times. I couldn't help but laugh.

"Yeah. At least a couple times a day."

"That's cool. I stroke it at least three times every day--sometimes
more--even when I'm getting pussy. I'm a horny guy."

"Well, we'll both be jacking it plenty in this place!"

"I know, right? Pussy's about the only thing this school is missing."

All of this talk about jacking off had made my cock lengthen, and I noticed
Derek was now at about half-mast. It felt unusual to stare at another guy's
cock like that, but it was so impressive, and Derek obviously didn't mind
the attention.

Smiling, he brought his knees up and slowly rubbed the soles of his feet
together.

"We're getting pretty hard," he said matter-of-factly.

"Yeah," I said huskily. It sounded stupid, but I couldn't think of what
else to say.

Derek looked at me for a minute, as if he were trying to read my thoughts,
and suddenly grabbed his backpack from the end of his bed.

"What are you looking for?" I asked.

"This," he said, pulling out a skinny blue bottle. "Try it. You'll like
it."

He tossed it onto my bed, and I picked it up.

"Lube?"

"Not just any lube. That's Gun Oil. It's like thirty bucks a bottle, but
it's worth it. The stuff feels amazing on your cock."

We'd both gotten fully hard by now, and Derek's cock was even more amazing
erect than it was soft. His thick penis curved beautifully upwards, ending
well above his navel. His cockhead had turned an angry purple and was
visibly throbbing. A large drop of precum had formed on top of his wide
slit, and he slowly rubbed it around the head with his thumb.

My head was swirling, and I looked at the bottle in my hand as I thought
about what to do.

"What's the matter?" he asked. "Don't use lube?"

"Derek...I've never jacked off with another guy before."

He cocked his head and looked at me in amazement.

"You're joking, right? Not even with your buddies?"

"No."

"Well, why the hell not?"

"I'm not gay."

Derek just blinked at me a couple times and finally laughed.

"Neither am I, dude. It isn't gay to jack off with another guy. And what
did you think you were going to do over the next year--kick me out every
time you wanted to bust a nut?"

"I guess I hadn't really thought about it."

"Look, Trent. I was really hoping that we wouldn't have to hide this from
each other. I want you to feel like you can jack off whenever you want,
even around me. Hell, I was hoping we could do it together, too. It's a lot
of fun."

I looked down at my twitching erection and back up at Derek, who had slowly
begun to stroke his shaft. Smiling, I popped open the bottle.

"This had better be some damn good lube," I said.

"All right, man! Trust me--you're really going to enjoy this."

I squeezed about five drops of the stuff into my left hand and grabbed hold
of my hard cock, slowly pumping my fist. It was warm and slick, and my
cockhead began to throb intensely.

"Ohhh fuuuuuck," I moaned.

"I told you that was some good stuff," he said. "Hey, be a pal and send
that bottle over here."

"Mmmph. Wha? Oh, sure. Sorry, man."

I tossed him the lube and he squeezed a liberal amount onto his drooling
erection. As he rubbed it in, he spit a couple times on his cock.

"I like to add a little spit when I use this stuff," he said. "Otherwise it
gets too intense and I can't last as long."

Derek stretched, groaning happily. He arched his back and flexed his toes,
then dropped his ass back onto the mattress and began to go to work on his
wet cock. He pumped it very slowly and rhythmically in his right fist. His
left hand moved to his smooth balls, and he picked up one, then the other,
slowly rubbing them between his fingers. I worked my hand in tandem,
watching fascinated as he pleasured himself. Suddenly, he turned his head
to the side and noticed me staring at him. Panicked, I quickly looked back
at my own cock.

"No, no--it's OK, dude," he said. "You were doing it right. We should
totally check each other out. That's part of what makes it fun."

"Yeah?"

"Definitely. You watch me, I'll watch you."

Feeling much less inhibited, I looked back at Derek, whose dark eyes were
now focused intensely on my cock.

"So I noticed you're a southpaw," he said, pumping his fist a little
faster.

"Yeah, but just to masturbate. The rest of the time I'm right-handed."

"Weird--my brother's the same way."

"You've seen your brother jerk off?"

"Oh yeah. We've been jacking together for years."

"Cool."

He was playing with his balls much more roughly now, and I reached my right
hand down and started to do the same to mine. He'd gone silent and was
looking at me expectantly. I guessed it was my turn to speak.

"So...are your balls sensitive, Derek?" I asked.

"Mmm, yeah. That's why I keep 'em shaved. Adds to the sensation. Fuck, this
feels good right now."

The room was filled with a wet slapping sound now as we worked our cocks
harder, and the whole room smelled of precum and lube.

"Hey," he said. "Ever do this?"

He turned toward me and spread his legs a little, rubbing his lubed finger
over his smooth taint and down over his pink asshole.

"Definitely!" I said, turning and doing the same. "That's the male G-spot,
man."

"Exactly. Hey, how close would you say you are to busting, Trent?"

"Maybe, like, five minutes."

"Me too. Want to try to cum at the same time?"

"Sure."

"OK--just let me know when you're getting close."

Derek slowly moved his fingers away from his hole and then started fisting
his cock with both hands. Even then, almost half of his enormous shaft was
visible. It would take three hands--maybe four--to cover it all. He moaned
loudly, obviously enjoying what he was doing to himself.

"Your technique's pretty cool," I said. "I mean--you do a lot of the same
stuff I like to do."

"You're not too bad either, lefty," he said, never taking his eyes off my
cock. "You're pretty talented with that thing."

A thick blob of clear fluid oozed out of my slit, and I dabbed it with my
finger. I leaned forward to lick it off, but stopped short when I realized
Derek was still watching me.

Without speaking, he stopped stroking and squeezed an equal amount of
precum out of his own dick. He scooped it up and swiped his broad tongue
across his fingers, slowly enjoying the flavor. He wasn't just tasting
it--he was savoring it. When he was done, he nodded at me to do the
same. He went back to pumping his cock as I sucked the precum off my
finger. It tasted mellow and sweet--I always liked my own taste.

I gripped my throbbing dick much harder now and began to pump it as fast as
I could. I watched as Derek did the same, pounding his shaft with his right
hand and palming his swollen cockhead his left. My balls were aching, and
Derek's, which had been hanging low before, had drawn up tight against
him. He was putting his whole body into it now. His tense muscles shimmered
with sweat, and his biceps flexed wildly with every stroke. His pink
nipples stood erect from his broad, smooth chest and his washboard abs had
become slimy with lube and precum. He was really fucking his fist, lifting
his ass up off the mattress with every stroke.

Never breaking from my feverish stroking, I slid a wet finger over my
taint, rubbing in a circular motion.

"Derek," I said, panting, "I'm really close."

"Fuck yeah--me too," he grunted.

A few strokes later, he moaned loudly, burying his cock deep into both
fists with a final thrust.

"I'm cumming!" he screamed. "I'm cumming! Oh fuuuuuuck!"

Watching Derek's orgasm was amazing. He arched his back high up into the
air. His toes curled. The muscles in his neck bulged. And then, a thick,
ropy shot of white jizz exploded from his spurting cock and landed on the
wall behind him. The next shot hit him square in the face, dribbling down
his lips and pooling in his blond stubble. Shot after shot of cum painted
his chest and collected in the crevices of his abs. He bucked into his
fists about ten or twelve times, finally collapsing onto the sweaty
mattress with an exhausted sigh. When he squeezed the last milky drop onto
his stomach, I knew I couldn't hold back. I came.

I wanted to scream but only managed a gasp as I hit my shoulder with a wet,
sticky glob of cum. My heels flew up and crashed back down into the
mattress as I gave in to wave after wave of pleasure. Seven shots of cum
hit my chest--one even hit me square on the right nipple. The final few
spurts dribbled out the end of my cock and onto my hand. After the room
stopped spinning, I finally let go of my softening erection and looked at
Derek, who was staring at me with a big, shit-eating grin on his face.

"What'd I tell you?" he said.

"That was awesome," I said softly. "Fuck, that was intense."

Just when I thought Derek was out of surprises, he did something that
caught me off guard. He scooped a big puddle of cum off of his chest,
brought it to his lips, and casually licked it up. He saw me staring and
shrugged.

"What?" he said. "It came out of me--I'm just putting it back. Haven't you
ever tasted your cum?"

"Yeah, a few times"

"It's good, right?"

"Yeah."

"Then do it."

I scooped a couple globs of cum off my chest and swallowed them. It was a
much stronger taste than my precum--a bleachy kind of bittersweet. As Derek
lovingly swiped and swallowed every last drop of his semen, I wiped up the
rest of mine with my boxers.

"Hey, Derek, you missed a spot," I said, pointing at the cum on the wall
behind him. "You going to eat that one too?"

"No way. I'm proud of that one. That one stays."

Even with the windows open and the fans going, the pungent smell of cum and
sweat filled the room. It was a distinctly manly smell, not too unpleasant.
Both our cocks had once again become flaccid, and as Derek reclaimed his
spot by the fan, I stood up and stretched.

"So what did you think, lefty?" asked Derek, patting me on the back.

"I'm glad you talked me into it."

"I told you it's more fun with a buddy."

"Way more fun."

"Well let's make a habit of this then, OK?"

"Definitely."