Date: Wed, 8 Apr 2009 21:13:20 -0500
From: Barefoot Preppie <barefootprep@gmail.com>
Subject: My Roommate Derek - chapter 2

"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."

Derek cracked open a bottle of water and offered one to me. Before I even
had a chance to open mine, he'd guzzled half of his and exhaled loudly,
smacking his lips. His blond hair, now matted with sweat, hung down over
his bleary eyes. Our jack-off session had been pretty intense, and he
looked completely spent. I lay naked on my bed still reveling in what we'd
done, and Derek hoisted himself up to unpack the rest of his things.

"Dude, can I open the door now?" he asked. "It smells like sex in here."

I looked at my shorts lying crumpled in the corner, and he cleverly caught
my glance.

"What, are you suddenly wang-shy?" he asked, wagging his long
penis. "Personally, I don't give a shit. Who's going to care?"

Derek had a point, and it felt so good to be naked in front of the fan that
I found myself agreeing with him.

"Yeah, go for it."

He swiftly propped the door open, exposing our mutual nakedness to anyone
who happened to walk past. It didn't really bother me, surprisingly. I had
a feeling that the dorm was going to have an atmosphere like a locker room,
anyway.

Derek pulled some photos out of his backpack and began to fasten them to
the wall above his desk. He stopped to admire one in particular, a wan
smile spreading across his face.

"What's that?" I asked.

"Prom picture," he said, holding it up for me to see. There was Derek,
barefoot in a black tux, kissing a beautiful blond girl on the
cheek. Looking at her impish smile, her long, slender legs, her perky,
perfect tits—it stung me as I was reminded of what I'd be missing at an
all-male college.

"That's Veronica," he said.

"Goddamn."

"I know, right?"

He carefully taped up the picture, and I grew wide-eyed at the next photo
he produced.

"Whoa, wait a minute," I said. "Why do you have a picture of naked dudes?"

He laughed and handed me the photo. I could see that the person in the
middle was Derek, and he had his arms around two other blond-haired
guys. They were standing in front of a cabin, and all three of them were
completely naked. They were all really fit, but neither of the other two
had a cock as big as Derek's.

"Are these your brothers?"

"He is," he said, pointing at the younger guy on the left. "That's my kid
brother Scott. Well, I call him a kid, but I'm just a year older. But the
other guy is my dad."

"He looks pretty young."

"Yeah, he's...I dunno...thirty-three, I think?"

"And how old are you?"

"Eighteen."

I softly chewed my lip as I did the math in my head.

"Yeah, yeah, I know," he said. "You don't need to say it. Babies having
babies. He was young. But my mom's a couple years older. She was eighteen
by the time my bro was born."

"And is she taking the picture?"

"Mom? Nah. She and Dad broke up when I was, like, three. She's in Germany
now, married with a couple kids. I get a card from her every
Christmas. That's about it."

"Heavy."

"Yeah, it's always just been me, Scott, and Dad. Guess that's why I'm
comfortable in my own skin. We're bare-assed all the time back home."

By this point, no one had walked past our open door, but as I heard
footsteps padding down the hall, I straightened up and tried to act
casual. If Derek could be comfortable being naked to the world, then so
could I.

The next thing I knew, a guy stopped in our doorway, and looking at him, I
didn't know what to make of him. He was a few inches taller than I was, and
his bleach-blond hair was gelled up into a slick fauxhawk. Trim but
muscular, he wore nothing but a pair of army-green shorts, but considering
the present company, he was decidedly overdressed. There were a couple
steel studs in his left ear and one in his eyebrow, and he was sporting
some pretty wicked tattoos on his lean torso. I'd have taken him for a
total badass if it weren't for his goofy grin.

"What's up, guys?" he said, extending his hand. "I'm Sean. I'm your RA."

"Trent," I said as he gripped my hand. The guy had one hell of a firm
handshake. Derek shook his hand and gave an enthusiastic nod.

"Hey, Sean. I'm Derek."

"Wow—you guys didn't waste time getting comfortable," he said, nodding
at our exposed cocks.

"Damn right," said Derek. "I fuckin' hate clothes."

"I feel ya," said Sean. "I like to let it all hang out."

Derek smiled smugly and pointed at me.

"Trent here wears underwear."

"Whaaat? You don't go commando?" asked Sean, scratching at one of his long
sideburns. "Fuck, I don't even own underwear."

Derek laughed and gave him a high-five.

"Me neither, man. Me neither."

I marveled at how open the guys were with each other, and I liked it. It
was just so cool. I'd always wished I'd had brothers—maybe this is what
I'd been missing as an only child.

I guess it would be fair to say that Sean and Derek hit it off right
away. They were totally on the same wavelength, and I think they were kind
of digging each others' vibe. Derek told him about going barefoot, and Sean
was pretty into it, saying that he skateboarded barefoot himself, and was
barefoot or in flip-flops the rest of the time.

"I actually haven't put on my flips at all today," he said, sticking out a
bare foot.

Not to be outdone, Derek proudly displayed one of his dirty soles, and Sean
laughed.

"You win, man," said Sean. "Shit, I'd have to run around barefoot for,
like, ten years to beat that."

By now, Sean had decided to get comfortable, and he sat at my desk and
began to talk with Derek. I didn't contribute much to the conversation, as
the topic quickly turned to masturbation, and I wasn't really sure what to
say. It turns out Sean jacked off as much as I did—a couple times a
day—and he said that the months without pussy could be pretty rough. He
was 20 and entering his third year at Jackson, so I'm sure he knew what he
was talking about.

"You guys should check out my whacking material," he said. "I've got
everything—titty mags, movies, lube, toys, you name it. You're welcome
to it."

"Seriously?" asked Derek, suddenly alert.

"Sure. You don't have to knock, but the door's usually open anyway. Take
whatever you want whenever. Just bring it back when you're done."

Derek's cock slowly began to lengthen, and his dark eyes glimmered
mischievously.

"Dude, do you mind if I go check it out?"

"Knock yourself out, buddy. Mine's the room next to the bathroom. All the
good stuff's in the box under my bed."

"Righteous," he said, giving his cock a tug. "Hey, Trent—you coming,
man? Maybe get some new jackoff lube?"

"I'm good for now," I said. "We've still got plenty of that Gun Oil."

Derek shrugged and stepped out of the room, walking down the hall naked,
almost fully erect but completely aloof.

"Your roommate's awesome," said Sean, laughing.

"Yeah, I don't think he has any shame."

"It doesn't look like you do either."

"Oh...well, I'm not usually naked like this."

"Don't see why you shouldn't be. There's no dress code in the dorms. All
the guys strut around naked eventually. Hell, I do."

Sean's pale blue eyes caught the light as he stroked his neatly-trimmed
goatee, and the tattooed skin on his firm chest grew taught.

"Wicked tats, man," I said. "How many of those have you got?"

"Five."

I could plainly see the barbed wire encircling each of his biceps, the
tribal moon beside his left nipple, and the sunburst below his navel. I
narrowed my eyes as I searched in vain for the other.

"Looking for the fifth?" he asked, smiling coyly.

Nodding at his crotch, he pulled the drawstring of his board shorts and
swiftly lowered them to his knees. I could see Sean was completely shaved,
and marking the smooth skin just above his cock was a small, five-pointed
star.

"Cool," I said, almost under my breath.

I'd barely been at Jackson for two hours, and I'd already seen two of my
fellow students' cocks, both bigger than mine. Sean was completely flaccid,
but judging by the size of his penis, I'd have to guess it got about nine
inches hard. His cock was long and on the thinner side, and the pale head
was wide and very blunt. He didn't have any pubes at all, and his smooth
balls hung heavy in the heat.

"Thanks, man. That last one's my favorite. Draws attention right where I
want it," he said, giving his soft cock a playful slap.

Grinning, he pulled his shorts back up.

"See?" he said. "We're not all modest here."

After a brief pause, Sean pointed his head toward the door.

"Well, your roommate either got lost or he found my porno stash."

"Yeah, Derek's a horny guy. He's already jacked off once today."

Sean smirked and tented an eyebrow.

"How do you know that?"

Immediately, I realized I'd been busted, and I bashfully dragged my toe
across the floor. Sean shook his head and laughed.

"Wow, one day without chicks and you're already tossing off with another
dude!" he said, snickering. "Jeez, I held off a couple months, at least."

I swiftly looked up at him and caught his widening smirk.

"Come on," he said. "Let's go see what your pal is up to."

I once again thought about getting dressed, but following Derek's bold
example, I followed Sean naked into the hallway.

The door to Sean's room was open several inches, and as we got closer, I
could hear a soft thumping sound. Sean pushed the door without knocking,
and I chuckled at what I saw. Derek was kneeling at the foot of Sean's bed,
slowly pumping his cock into a long, clear tube.

"Ah, you found the Fleshlight!" said Sean. "I just hope it was clean,
buddy."

Derek nodded, and I stepped into the room, closing the door behind me.

"You ever use one of these things before?" asked Sean.

"Nah, I...ungh...haven't," said Derek, breathing heavily. "It's not
bad. Feels like a cunt."

Sean kneeled next to Derek, picking a bottle of Astroglide off the floor.

"You guys can borrow it whenever you want," he said. "Trust me—this
thing is going to be your best friend at Jackson."

I walked over to where the two were kneeling, my heart quickening at the
taboo spectacle. Sean squeezed a large gob of lube into his palm and pulled
the Fleshlight off of Derek's pulsing erection.

"First off, you've got to use way more of this stuff," he said, grabbing
Derek's hard cock and coating it with lube. Derek inhaled sharply and the
unexpected sensation, smiling as Sean touched him. Sean played his fingers
over Derek's long cock for what seemed like a couple of minutes before
plunging the Fleshlight back onto it.

"Gah! Easy, Sean, easy."

"Sorry. I'm usually pretty rough with this thing."

As I walked over and knelt on the floor beside them, Sean casually passed
me the bottle.

"Lube yourself up, Trent. It'll be your turn in a minute."

I wet my cock and began to jerk myself slowly as Sean worked the Fleshlight
up and down onto Derek's huge dick. Derek was obviously enjoying it, lazily
rubbing his broad chest and grinning, lost in lust.

After a few minutes, Derek clenched his toes and began to tense up, and he
quickly grabbed onto Sean's arm.

"Ah! Hold up, dude," he said. "I don't want to cum just yet. Let Trent have
a go."

Sean pulled the Fleshlight off of Derek, turned, and pushed it onto my
cockhead with a satisfying squish. I instantly felt the slickness of lube
and Derek's warm precum.

"You ready for this?" Sean asked me.

"Yeah."

"OK, just fuck it like a pussy, man. Don't hold back."

I sank my cock into the Fleshlight, amazed at its tight grip. It was warm
and slippery, and I slowly began to fuck it as Sean pumped it up and
down. It really did feel like I was fucking a girl, and if I closed my
eyes, I could imagine I was doing just that. But the sight in front of me
was strangely more interesting.

Derek reached for the waistband of Sean's shorts and slowly pulled them
down. I didn't even think Sean had noticed at first, but he suddenly pulled
the Fleshlight off of me and pushed his shorts the rest of the way off. I
could see that his cock was still completely limp, and Derek reached over
and rubbed the star on Sean's smooth groin.

"Rad shave job, dude," he said. "I used to shave it all off, too."

"Thanks," said Sean. "I shave every day. Feels awesome."

Derek's hands wandered down to Sean's growing cock, and as he teased it
with his fingers, it slowly hardened until it stood straight up. Sean's
oozing cockhead smacked against the tattoo on his groin, and he groaned as
Derek began to jerk him off.

I'd never even thought about doing anything like this before, but I found
myself feeling curious and excited as my roommate gave our RA a handjob
right in front of me. Emboldened, I reached out and squeezed Sean's smooth
balls. It was the first time I had ever touched another guy...sexually, at
least.

"Fuuuuck," moaned Sean, "You guys are awesome."

Sean now lay on the floor with his legs spread wide, forcefully fucking
Derek's fist. Before I even knew what I was doing, I was working his balls
with my fingers and rubbing his taint. Derek looked over at me and smiled
as we brought Sean to ecstasy.

I could feel the cum boiling in Sean's balls, and they suddenly felt like
they were about to burst.

"Guys, I don't...gah...I don't think I can—"

That was all the warning we got. A blast of hot, wet jizz erupted out of
his shaved cock and hit him square in the forehead, dribbling onto the
punkish steel stud in his eyebrow. Cum splashed onto his neat goatee, and
the final spurts coated his inked chest and abdomen. He didn't cum anywhere
near as loudly as Derek did. In fact, Sean barely whimpered as he writhed
with pleasure, digging his fingers into the carpet.

Sean grinned from ear to ear and wagged his head, as if he were waking from
a deep sleep. He lay there panting softly for a moment and finally spoke.

"Whoa...thanks, guys. It's pretty cool that you're into this."

Derek swatted my ass with his sticky hand and gave me a playful nudge.

"Trent never did anything like this before today," he said.

"No way!" said Sean. "Shit, you could have fooled me."

The three of us lay on the floor, sweaty and naked, and before I could even
react, Derek reached over and took hold of my erection.

"I think you need to get off, lefty."

Sean watched attentively as Derek began to stroke my hard cock. Derek
looked right at me with his deep brown eyes, leaned down, and spit a couple
times on my cockhead.

"Hope ya don't mind, Trent. You were a little dry."

"Thanks, man."

Sean stood up and began to wipe the cum off of his chest with a towel,
never looking away from the two of us. Derek and I were now sitting on the
floor across from each other, and directly in front of me was Derek's
impressive erection. It was wet and gently throbbing, and as he slowly
jerked me off, I thought about reaching for it. I marveled at its gentle
outward curve and watched his thick cockhead pulse against his firm abs.

Taking a deep breath, I reached out and wrapped my left hand around Derek's
erection, and his half-smirk quickly turned into a grin.

"All right, Trent! Man, I was hoping you'd go for this."

Derek and I jerked each other earnestly as Sean sat there naked, watching
with a curious expression. I'd never held another guy's cock before, and
Derek's was a handful. Precum leaked all over my hand as I stroked his hot,
smooth rod. His cock was so hard that it felt like pulsing steel, and I
tightened my grip as I pumped it faster.

I involuntarily let out a low moan as Derek gave me the best handjob of my
life. He expertly flicked his wrist with every deliberate stroke,
alternating his speed and paying careful attention to my sensitive tip. I
was fairly certain that Derek was as straight as I was, but it was obvious
that he had done this a few times before.

"Does that feel good?" he asked.

"Grip it a little tighter," I said softly.

He clenched his fingers and continued pumping.

"Like this?"

"Yeah, and...ungh...faster."

"You got it."

He spat a couple more times on my dick and quickened his strokes. My cock
instantly responded, oozing precum onto the floor. In turn, I gripped his
cock more firmly and stroked it faster.

"Am I doing this right?" I asked.

"Mmmph, definitely," he moaned. "Keep that up and I'll cum in a minute."

I could feel my own orgasm building as Derek skillfully jacked my cock, and
he must have felt it.

"Let it happen, Trent. Just blast it."

I let out a mighty grunt as my cock shot off in his hand, and he never
slowed his stroking as I came. My orgasm was almost as powerful as the one
I'd had earlier, and my jizz erupted onto his firmly toned chest, running
down his abdomen into his closely-cropped blond pubic hair. He winced
slightly as I sprayed him, and I couldn't help but laugh.

I continued to stroke Derek's cock hard and fast, and he looked right at
me, smiling smugly.

"Here's yours, fucker," he said.

Derek plunged his cock into my fist, and suddenly, he was cumming. I felt
the thick semen course through his dick as he fired off multiple shots,
coating my chest and neck with his hot load. He threw his head back and
cried out, overcome by the sensation. After about nine or ten shots, he
uncurled his toes, rubbed his eyes, and regained his senses.

"Damn, guys."

We both looked up to see Sean, looking stunned and amused. I'd almost
forgotten he was there. He handed me a towel, and Derek and I cleaned
ourselves up.

"Thanks for being cool about this," I said, shaking Sean's hand.

"Not a problem, man. You guys can always come to me for whatever."

"Let's definitely hang out later," said Derek, handing the cum-soaked towel
back to Sean.

"For sure! I want to get to know all you guys better."

Derek and I walked casually naked back to our room. I felt exhausted but
exhilarated. Derek sat down, propping his tough feet up on his desk.

"You're a fun guy, Trent. I'm going to like living with you."

"Thanks, Derek."

I was going to like living with him, too.