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This work is copyrighted to the author © 2008.  Please
don't remove the author information or make any changes
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My Friend Derek
by Feebofile (feebofile@hotmail.com)

***

My friend Derek isn't exactly a handsome guy, but 
somehow he manages to wind up in the most outlandish 
sexual situations. (MF, oral, anal)

***

My friend Derek isn't exactly a handsome guy, but 
somehow he manages to wind up in the most outlandish 
sexual situations. He's not charming or even nice most 
of the time.

I've known Derek since we were in fourth grade 
together. He was the one who was always dropping his 
pencil to look up girls' skirts. I was the one who 
always laughed at him, pissing off the teacher. Derek 
was never mean-spirited, but a lot of girls thought he 
was. He was just playing around, like a boy with a 
ball.

These are some of his more interesting stories.

Chapter 1: The New Girl Story

Jamie was the new girl in school in seventh grade. She 
was blonde, perky, wore short skirts, and was just 
about everything a boy could want in a girl at that 
age. Every boy in school wanted to sit next to her in 
class and walk next to her in the corridor. But it was 
Derek who got to her first.

Jamie usually took the early bus home, but one day she 
missed the bus and had to wait around in the cafeteria 
for the late bus. Derek was hanging around the girl's 
locker room trying to catch a peek inside, when he 
noticed something better. He wasn't exactly the 
romantic type, so rather than talk to her or smile at 
her or anything that a normal kid might do. Instead, he 
snuck up behind her and pulled out his dick.

Jamie wore a pink tank top with a white tee shirt 
underneath. She was wearing a jean skirt with her legs 
crossed underneath the cafeteria table. Her short 
blonde hair was pulled into two small pigtails. She was 
busy with her math homework, completely oblivious to 
the guy whacking off not three feet behind her.

Like most twelve year olds, Derek took less than a 
minute to cum the first time around. Small jets of cum 
sprayed out from one of the best orgasms he'd ever had 
in his young life. Jamie felt little splashes of 
wetness on the back of her neck, and whirled around to 
see her first dick.

"Eeew!" she cried. "What are you doing?"

Derek didn't really have a good response. Spewing over 
classmates in public cafeterias weren't exactly covered 
in proper etiquette. So he did the next best thing - he 
ran off with his dick still flopping around.

"Wait!" Jamie yelled. "I won't hurt you."

Against every instinct in his body, Derek boldly walked 
back into the cafeteria, pants still unzipped. Jamie 
stared, mesmerized, and reached out slowly to touch it. 
Derek's little dinky was erect again, waiting for more 
action.

Slowly, Jamie leaned forward and kissed the tip of his 
dick. "I watched my mom do this to my dad once," she 
said, as she gently massaged his dick with her tongue. 
Derek stepped up even closer to her as his dick slipped 
into her mouth. Her teeth scraped his boner at first, 
but he gently corrected her by yanking on her pigtails 
and telling her to use less goddamned teeth.

Jamie's first blowjob ended about 15 seconds into the 
act when Derek splooged into her mouth. Startled, Jamie 
pulled back, but Derek continued jizzing on her lips, 
nose, and cheek. Jamie reached up with a soft hand and 
rubbed it into her skin, feeling it between her 
fingers.

Derek and Jamie went out for two weeks or so, until her 
parents came back one day and caught her blowing him on 
their couch. They chased him out and then transferred 
her to some private all-girls school.

Chapter 2: The Football Party Story

Derek and I weren't the types that normally got invited 
to high school parties. But Derek always had a way of 
finding out where the best ones were. I'd just get a 
call from him on Friday nights from some random 
location and he'd be telling me how awesome the party 
was and how I should get over there before the beer ran 
out.

Hanging out with a bunch of jock and girls that 
wouldn't give me a second look wasn't my idea of fun, 
so I always declined. The story that changed my mind 
happened one night around midnight.

Derek had staked out a football player's house and had 
followed him to some cheerleader's house up in the 
hills. He gave me the usual ring, but when I declined, 
he didn't have a single person to talk to, and he ended 
up drinking himself silly. He was staggering around at 
midnight when he ran into Stacy Prescott, who could 
barely stand up.

He helped her up a flight of stairs, where she promptly 
collapsed and passed out. Like a true gentleman, Derek 
seized the opportunity to lift up her cheerleading 
sweater and check out her boobs. His hands roamed 
around her stomach and rubbed her nipples through her 
bra. He also took a peek underneath her short pleated 
skirt, rubbing her cunt through her silky panties. They 
certainly weren't standard cheerleading panties; she 
must have changed into them for the party, but kept her 
cheerleading outfit on because she was pretty hot in 
it.

At some point, molesting her wasn't enough to satisfy 
him, so he picked her up and started checking bedrooms. 
All of the bedrooms were full, so the only other room 
available was the upstairs bathroom. He went in and 
laid her on the floor, and continued molesting her. He 
was pleased to find out that, despite her general 
unconsciousness, rubbing her clit had enough of a 
lubricating effect to slip in a few fingers.

He finger-fucked her for a few minutes, and then pulled 
down her panties and began fucking her for real. She 
slipped in and out of consciousness, but Derek didn't 
care. He pulled her legs up over his shoulders, fucking 
her deeply. Whiskey dick was definitely the only thing 
that made him last more than a few seconds, but he 
still blew his load rather quickly. He pumped her full 
of semen, and then wiped his dick off on her panties.

He was about to put her panties back on when the door 
handle jiggled. He had just enough time to hop into the 
shower and hide behind the curtain before someone 
entered.

"Holy fucking shit," someone announced. He heard the 
door close, then lock, and then a zipper was pulled 
down. Some shuffling occurred, and then the sound of a 
squishy cunt as someone else fucked Stacy.

Derek was bold enough to take a peek outside, and 
nearly gave away his position by laughing. It was 
Jeremy Evans, Stacy's boyfriend, getting his sloppy 
seconds. "Fucking whore! Fucking whore!" he hissed, as 
he fucked her hard. He was really mad, totally red in 
the face, and pumping her for all she was worth.

He kept plugging her for nearly ten minutes while Derek 
developed a leg cramp in the shower. Finally, Derek 
heard the characteristic moaning of someone cumming and 
the smell of semen permeated the air of the bathroom 
once again. Jeremy groaned a few times, and then 
collapsed on the ground.

Derek was sort of unsure of what to do, so he hung out 
for another few minutes until he heard Jeremy snoring. 
He then crept out of the shower intending to leave. But 
he couldn't resist one more look at the beautiful 
Stacy, lying spread-eagled on the bathroom floor, with 
her skirt hiked up to her waist and cum dripping out of 
her twat. He also noticed that rather than cumming in 
her pussy, Jeremy had elected to pull out and spray her 
face.

Jeremy was curled up in a little ball beside Stacy, 
sort of cuddling her. While Derek watched, he snorted 
once and the rolled over onto his other side, and then 
puked onto the floor. He didn't wake up, just upchucked 
and then passed out again.

In a move that could only be described as requiring the 
hugest balls of all time, Derek fucked Stacy again 
while her boyfriend lay not more than 3 feet away from 
them. He wiped himself off on her panties again, and 
then tucked them in his pocket as a souvenir. He ended 
up passing out on the front lawn, but left with an 
incredible story.

Chapter 3: The Back to School Story

Derek graduated from high school with the rest of us, 
but hadn't gotten his shit together during his senior 
year and ended up working for a year while he applied 
to college. He worked full-time at a bakery, which 
meant getting his ass up at 4AM, but it also meant he 
was done by noon. His parents couldn't stand the 4am 
alarms, so he moved out into his own place, so he had 
all the freedoms of adulthood. But because he was born 
in September, he didn't turn 18 for a few months after 
graduation.

It was during this time that Derek made a vow to fuck 
as many underage girls as he could, while he still 
could. Well, legally anyway, but that's another story.

Alyssa was a budding 15-year-old rebel who skipped 
school one day and hit Derek up for smokes as he was 
walking into a supermarket after work. He wasn't 18, 
but with his bakery uniform, he looked old enough so 
they never checked him. They shared a cigarette, and 
laughed about how dumb people were.

Then he took her home and fucked the shit out of her.

They sort of fell into this pattern where she'd skip 
school and they'd just fuck all afternoon. Then they'd 
smoke a bowl or two, and fuck a little bit more until 
dinnertime.

Alyssa was almost a virgin when they first met. She had 
only been with one other guy, and they had only done it 
a few times before they broke up. But within a matter 
of weeks, Alyssa was turning into a sick, twisted 
nymphomaniac. After Derek had punched out her anal 
cherry (which took all of two days), she bought this 
huge black dildo and demanded he fuck her ass with it 
while he plugged her cunt with his dick.

Within one week, she had a small collection of bondage 
equipment that she kept over at Derek's place. The only 
problem is that Derek grew increasingly frustrated with 
the concept of being tied (heh, heh) to one woman. He 
wanted some new pussy, and he was looking for just 
about any excuse to break it off with Alyssa.

He tried the pussy way of going about it first. One day 
he decided to piss in her mouth after she had blown him 
and was cleaning him off. But it actually had the 
opposite effect - the slut loved it, and got off twice 
as the piss ran out of the corners of her mouth and 
soaked into his sheets.

Alyssa grew increasingly clingy in the week after that, 
insisting on cuddling after sex and calling him 
"honey". Finally, Derek could stand it no more and 
decided on a deed so dastardly that she absolutely had 
to break it off with him.

First, he convinced her to let him fuck her at the high 
school. They found a nice bathroom in a secluded corner 
and made plans to meet there during the passing period. 
Derek brought the handcuffs, and locked her to the 
plumbing after he bent her over the toilet. He started 
fucking her from behind, hard, bringing her to orgasm 
in a matter of seconds.

He finished himself off inside her pussy, but pulled 
out while he was cumming so that half of his sticky 
load was deposited on her ass and legs. When he was 
done, he climbed up on the toilet and straddled her 
head for the grand finale. He had taken a shitload of 
laxatives that morning and had quite possibly the 
nastiest shit in the world brewing. He let it all out, 
all over her hair and back.

For the first time in their short relationship, Alyssa 
seemed to question whether something was fucked up or 
not. She tried to protest, but the shit was just 
pouring out of his ass. Some of it ran down her face 
and dripped into the toilet, but all in all it ended up 
all over her clothes.

He carefully climbed down, and then surveyed his 
handiwork. Alyssa was cursing at him, and not in a 
particularly nice way. When he didn't immediately 
respond to her cries to unlock him, she tried to kick 
him with her legs.

"You bastard! You fucking bastard!" she yelled. "I hate 
you!"

"Fine," he said nonchalantly, "Then it's over."

Then he walked out.

Chapter 4: The Crazy Psycho Bitch Story

Not all of the bad things that happened to him were his 
own fault, although I have to admit most of them were. 
He finally made it to senior year in college by sliding 
through with the lowest possible passing grades. He had 
a few girlfriends, but was generally unwilling to 
commit to any one of them, until Sharon came along.

Sharon seemed like a normal girl at first. She was the 
same year as Derek, which meant she was a year younger. 
They met on the quad one day and hit it off, spending 
most of their time at the various movies shown on 
campus or at local restaurants. For once, Derek seemed 
to be having a normal relationship, and he seemed as 
pleased as anyone else about it.

The first indication that something was wrong was 
Sharon demanding that the two of them purchase a cat 
together and that Derek should keep it at his off-
campus apartment. Most people recognize this as classic 
signs of bitch, but we were young and stupid and Derek 
thought that it might not be so bad.

Once they started having sex, Sharon got her claws 
deeper and deeper into him. We all assumed it was bad 
luck that she had these emotional breakdowns whenever 
the guys had something planned. Her great-aunt had a 
stroke one day right before poker night, and then her 
cousin asked her and Derek to help her move one day 
when we were supposed to be go-kart racing.

It became increasingly obvious that she was intensely 
jealous of any time not spent with her, which cramped 
Derek's lifestyle.

To make things worse, Sharon gave what Derek described 
as "the world's worst head." Oral sex was a staple of 
Derek's sexual diet, and not only was Sharon bad at it, 
but she refused any advice about getting better. She 
got really pissy when he tried to show her how to do it 
right, and refused to do it at all when he suggested 
she was sub-par.

After a few fights, Derek managed to negotiate back 
Thursday night poker nights with the guys and a promise 
to improve her blowjob technique, in return for 
basically signing away the rest of his life. Things 
seemed to be going really well - he got some time 
alone, and he was getting some decent head. She seemed 
to take his advice well, improving dramatically and 
even deep-throating him on occasion.

One night we were playing poker when Mike's roommate 
decided to have all his anime buddies over for some 
Dragonball Z or something absurdly gay like that. Since 
the rest of us lived in the dorms, we decided to chance 
a run-in with Sharon and move poker night over to 
Derek's apartment. We thought there was a chance nobody 
would be home, but we were wrong.

Oh, my God, were we wrong.

Derek opened the door, and at first, we thought we had 
the wrong apartment. Six black homeless guys were 
sitting around his living room, naked from the waist 
down and stroking their boners. There was some sort of 
porno playing on the TV, and none of the guys even 
noticed us at first. Finally, one of the guys spotted 
us out of the corner of his eye, got real scared, and 
rushed past us out the door without even putting his 
pants back on.

The others saw us soon after that, and all of them 
basically rushed out in various states of undress. 
There were a few pairs of dirty, grimy pants left 
behind, as well as a rucksack or two.

While the porno blared out of the TV, Derek just stood 
there, mouth open, wondering what the hell just 
happened.

Suddenly, his bedroom door open, and Sharon's voice 
called out, "Who's next?" Another homeless man 
staggered out, dick still dripping cum. Sharon soon 
followed, wearing only a pair of thigh-high white 
stockings and high heels. Her lips and chin were 
plastered with cum, and there was not a single doubt as 
to what just happened.

I'm not saying we're proud of what happened next. I'm 
just saying that Sharon was a cheating bitch, caught 
red-handed, and we were all furious for Derek. So when 
Derek demanded that she suck us all off, we neither 
made it easy for her, nor did we care that she was 
crying while she did it.

Derek made us leave after she had finished us all off, 
so we never got to see him sodomize her without any 
lubricant, nor did we get to see him throw her naked 
ass out onto the street. Or throw all her personal 
items on top of her from the balcony. Or run her 
fucking cat over with his car.

She DID give a pretty good blowjob, though. It turns 
out that she had been practicing on homeless guys she 
picked up off the street.

Chapter 5: The Fucking A Stripper Story

About a year ago, Derek got engaged to some bitch named 
Elaine. We never really liked her, but Derek negotiated 
some better terms with her and for the most part 
retained far more freedom than he had with Sharon. We 
didn't really understand why he felt compelled to ask 
her to marry him at all. The best we could figure was 
that his line of work (sales) really required 
representatives who exuded stability and Elaine was 
good enough to fit the role.

At any rate, a good wedding deserved a good bachelor 
party, and preferably one that involved alcohol and 
titties. Elaine wasn't about to allow Derek to go 
anywhere, so we had to invent an excuse to get him away 
for a night. The perfect opportunity came up one 
weekend when Elaine's grandmother found a beautiful 
wedding dress, but in a boutique about 3 hours away. 
This eventually expanded into a whole-weekend trip down 
to visit her grandmother, which meant that we had the 
entire weekend with Derek.

We took the precaution of planting enough voice mails 
at his home throughout the week in order to convince 
Elaine that Derek's boss was up his ass and that Derek 
would be working at least 30 hours over the weekend.

Our first stop was an Indian casino; where we proceeded 
to gamble the night away and get enough free drinks in 
order to make the $20 cover at the strip club seem 
reasonable. Once we got inside, we spent the rest of 
the night waving ones at the strippers and buying lap 
dances for Derek. He particularly liked this one young-
looking brunette named Pixie, and her services were 
requested at least three times that evening.

After the first lap dance, Derek mentioned to us that 
she seemed familiar. He was pretty sure he went to high 
school with her or something, but she didn't seem to 
recognize him, nor was he able to place exactly where 
he had seen her before.

About 5am, we decided to call it a night, and we all 
headed back to the casino to catch a few winks. We woke 
up around 11 am to find Derek gone, and him not 
answering his cell phone. He didn't show up until 
almost 3pm, arriving in a cab and wearing the same 
clothes as he had worn the night before.

He explained that after we went to sleep, he got up and 
went back to the club. He had arranged to meet Pixie 
after her shift ended at 6am, and they went out for 
breakfast together, and then for some sex at her 
apartment. This was strictly off the clock, and he 
didn't even need to pay her, since he had remembered 
where he had seen her before and used to coerce her.

Pixie's real name was Delia Sanders, and she was the 
daughter of Eric Sanders, who was manager of sales at 
Derek's company. She was 18 and in college, and 
apparently not getting enough from her parents to avoid 
stripping at the local strip club for extra spending 
money. Sleeping with Derek was supposed to be a one-
time thing just to keep him from spilling to her dad, 
as long as he used a condom and didn't want anything 
besides a straight lay.

The deed being done, he was changing and getting ready 
to leave when someone buzzed Delia's apartment. Derek 
was shoved into the closet and he had to wait there for 
half an hour while Delia's 15-year-old sister, Lily, 
told a sob story about how terrible life was at home 
and how she was running away. Lily had stolen the 
family car and drove up to Delia's to say goodbye as 
she ran away to Canada. To make things worse, she 
didn't have the foresight to withdraw some money from 
the bank, which meant that she was broke after paying 
for breakfast in cash.

Delia convinced Lily to stay at her place for a few 
days, but in order to do that she had to call into 
"work" and cancel her shifts. From the way that Delia 
insisted on going out onto the balcony to talk, it was 
pretty clear that Lily didn't know where Delia actually 
worked.

Derek got sick of waiting in the closet and decided to 
venture outside. He introduced himself as a friend of 
Delia's, and acted the part of a gentleman as he 
apologized for eavesdropping. He said that it was 
Lily's idea to fuck for money at first, but we're all 
pretty sure that propositioning the underage girl was 
his idea.

The end result was the same; he ended up fucking Lily 
right there on the couch as Delia made her phone call 
outside. Having drained his balls an hour earlier, 
Derek took a little bit longer than normal to cum, but 
the fifteen-year-old pussy eventually coaxed it out of 
him. He left her a hundred dollars, the agreed price, 
and then left before Delia even got off the phone.

When he came in, we all just assumed he had called up 
an escort service, since he had the big shit-eating 
grin on his face, but the extent of his depravity 
wasn't known until several weeks later. Word of his 
little exploits ended up getting back to his boss, who 
fired him on the spot. Without a job, Derek didn't 
really feel the need to get married any more, so he 
broke off his engagement with Elaine.

Chapter 6: The Fucking at Work Story

About two weeks ago, Derek was trolling the bars for 
sluts when he met a redhead named Elizabeth. She had 
come in with two friends, but she was clearly the least 
attractive of the three. She wasn't bad looking, but it 
was more that her friends were smoking hot.

Derek was a big fan of the low-hanging fruit, which 
usually meant picking up the skanks left over at the 
end of the night, but in this case, he saw a golden 
opportunity when two guys asked to join the three 
ladies. They were clearly gunning for the more 
attractive two, which meant that the redhead was going 
to feel left out. Derek swooped in, everyone was happy, 
and at the end of the night, the three paired off quite 
nicely.

Elizabeth, or Liz, invited him back to her place, which 
was a big red warning flag to Derek. He disliked the 
obligation to stay after sex, and being at her place 
limited his options.

So he took her to a deserted road just outside of town 
and raped her. Well, raped might be a strong word. She 
didn't object, but she clearly wasn't having fun. He 
fucked her pussy until she went dry, and then pulled 
out a jar of Vaseline he kept in the car for just an 
occasion and fucked her ass until he came.

He dropped her off at her apartment and they did not 
exchange numbers.

Pleased with his performance, he bragged about this for 
several days in a row, both to his friends outside of 
work as well as his coworkers. As a matter of fact, he 
was relaying the story to some people in marketing when 
a company meeting was announced.

At the meeting, a reorganization was rolled out and a 
consultant was introduced who would help decide who was 
kept. Derek was a dumb fuck and didn't even recognize 
her until he walked into his interview. He introduced 
himself and she laughed a little.

"You don't recognize me, do you?"

It took him a while, but Derek eventually removed her 
glasses (mentally, of course) and took her red hair 
down from the bun.

"Liz?"

"That's Ms. Elizabeth O'Connor to you, you dumb cunt."

Derek could tell he was in for a rough interview. Not 
only did she have it in for him, but he was 3rd to last 
in sales for the past two quarters and he frequently 
came in late. To add insult to injury, he had two 
accusations of sexual harassment leveled against him.

Normally, he wouldn't care if he lost his job, but he 
had just purchased a new car and drained his bank 
account to do it. Being unemployed now would be 
disastrous.

Derek made quite possibly the boldest play of his life 
at that moment -- he offered to fuck her again in 
return for his job.

"What? You were fucking terrible."

"Yeah, but that's because I didn't think I'd see you 
again," Derek admitted.

Liz hesitated for a few seconds. She was clearly still 
attracted to him, and Derek just sat there smirking as 
his boner grew. Finally, Liz asked, "Where?"

"Here," Derek said. "We can close the blinds."

Derek closed the blinds and bent her over the table 
where everyone's resumes and internal files were laid 
out. He bent her over the table and fucked her from 
behind vigorously. He made sure she came at least twice 
from his efforts before depositing a sticky load inside 
her.

She was wiping up when her boss walked in. Her panties 
were down on the ground and Derek was just pulling up 
his pants, so it was clear what was going on. Derek 
didn't know what to say, but Liz did. She immediately 
offered the same deal that Derek had offered just a few 
minutes earlier -- she'd fuck him if she could keep the 
job.

Derek sat there and watched as his boss plugged her 
cummy pussy. His boss didn't seem to mind sloppy 
seconds, and soon enough, another load of sperm was 
added to her cunt. Liz's squeals of pleasure had Derek 
hard again, and as soon as his boss had zipped up and 
left, he stood over Liz, kneeling on the floor, and 
demanded that she suck him off.

Liz gave him half a blowjob and then asked him to fuck 
her again. Derek wanted a little more anal, so he laid 
her on the table and scooped out as much cum out of her 
pussy as he could with his finger. He lubed up her ass 
and then weaseled his cock in. With her legs up on his 
shoulders, he pounded her for another fifteen minutes 
while he stroked her clit off another time with his 
thumb.

At the end of the day, Derek kept his job, and gained a 
girlfriend. Not bad for a day's work.

END

* * * * * * * * * * * * * * * * * * * * * * * * * * * *
It's okay to *READ* stories about unprotected sex with
others outside a monogamous relationship. But it isn't
okay to *HAVE* unprotected sex with people other than
a trusted partner. 4-million people around the world 
contract HIV every year. You only have one body per 
lifetime, so take good care of it!
* * * * * * * * * * * * * * * * * * * * * * * * * * * *
Kristen's collection - Directory 60