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Watching Out For A Friend

6/13/2008

It was the beginning of August, a beautiful summer day.
I was relaxing in front of the TV having a Coke when the phone
rang.


"Hello?" I said into the receiver.


"Hi Jeremy, it's Lisa, Chris and Jackie's
mom. How are you today?" the voice on the other end
said. Lisa was my mom's best friend since high school.
Chris was my best friend and Jackie was his younger sister.
We had all grown up together.


"I'm pretty good, it's good to hear from
you. How's the family?" I asked, making small
talk.


"Everybody's fine here. Actually, I called
to ask a favour of you."


Wondering what kind of favour she wanted, I said, "Sure,
anything for friends. What can I do for you?"


"We've decided that we're going to send
Jackie to Algonquin College. That's the private school
close to where you live, is that right?"


"Yeah, it's just a couple of blocks from my place.
That's a good choice; they have lots of extracurricular
activities, and a top-notch curriculum. She'll have
lots of fun there. Did you want me to show her around the city?"
I asked.


"Actually, Tom (Lisa's husband) and I were hoping
she may be able to stay with you. Is that all right?"
Lisa went on to explain, "Because of the price of tuition,
we'd rather not have her stay at the residence. Then
we thought that she could stay with my brother and his wife,
but his job was transferred down south a little while ago.
We don't know anybody else who lives there, and we'd
feel a lot better if she was staying with a familiar face
than we would if she had her own place or was living with roommates."



I had to digest what she was saying. She wanted Jackie, who
had blossomed into a very beautiful young woman, to stay
with me, a single guy who lived alone, with no parents or
relatives around. I'd never even thought of touching
Jackie sexually, and I think her family knew that; but for
Lisa to ask that favour, she had to be very trusting.


"Of course, Jackie is welcome to stay here. I'm
in a good neighborhood, secure building and well-lit street, "
I replied.


"We really appreciate it. How much should we pay you?"
Lisa asked.


"Oh, don't worry about it. I wouldn't think
of asking you guys for money, " I responded, thinking
to myself that just seeing Jackie in that Algonquin uniform
would be payment enough.


"No, " Lisa insisted, "it's a big
favour you're doing for us, and you should be compensated."



"Well, I guess a hundred dollars would be fine, to
cover extra food and stuff like that."


"Thanks, Jeremy. I'm glad we can count on you.
Talk to you later, " Lisa said, and then she hung up.



I stopped for a moment and thought. Lisa was willing to pay
me a hundred dollars a month, and I would get to see Jackie
five days a week, wearing that Algonquin school uniform,
which my friends and I have declared is the best looking
school uniform we've ever seen. Most of the girls there
wear their skirts extra short; whether it's because
they're sluts or just teasing the guys who go there,
we don't know. I couldn't believe my luck.


A bit of background... I just finished college the previous
April and have my own large apartment in a city of about 50,
000 people. I inherited a sizable yearly sum of money from
my great-grandparents (whom we didn't know were very
wealthy people until after they had passed away) therefore,
I'm lucky to be financially stable without working
a great deal. I used some of the money to set up a photography
studio in one of the rooms in my apartment where I can do grad
pics, formal shots, that sort of stuff, for people who don't
want to pay the sitting fee elsewhere. For a little extra
cash (and to meet girls), I put in a few hours a week at a restaurant
close to the college that becomes a no-alcohol bar at night.
Usually the clientele is a high school crowd, which is too
young for my taste, but every now and then a hot college coed
comes in either while on a spare or just after her class.
I manage to get my share of phone numbers.


About a week before school was supposed to start, I drove
down to Jackie's to pick her up. Jackie's parents
wanted her to spend the week before school in the city, so
she could find out where everything was; bus schedules,
places to eat, and so on. It worked out for all parties; Jackie
got acclimatized to the city, her parents got peace of mind,
and I got a little bit of cash for expenses incurred.


When I got there, Jackie greeted me at the door with a hug.
"Hi Jeremy! Thanks for letting me stay with you, "
she said with delight. She was wearing white T-shirt and
Jean shorts that came about halfway down her thigh. Maybe
it was just me, but she seemed to let her hug linger a little
longer, longer than a normal friendly hug to which I was
accustomed. I remembered that Jackie had had a crush on
me when we were little kids, but I figured that like all childhood
crushes, it was probably gone by now.


I smiled at her. "Hi Jackie, it's good to see you
again. You'll have lots of fun at Algonquin. I've
got friends who went there, and they all speak highly of
it."


"Oh, I don't wanna talk about school right now.
Are you gonna let me cook for you? I'm getting pretty
good at it, you know."


I laughed. "Sure, you can cook for me. All I really
know how to use is the electric frying pan and the microwave."



"And are you gonna make me wear my skirt REAL short?
I know guys like that kind of thing."


"Jackie, I'll probably be telling you to keep
it at knee length. Any shorter and you'll have to beat
my friends away with a stick, " I explained with a
laugh.


"And can we..." Jackie went on to give a long
list of stuff to do.


"Jackie, we can do whatever you want, as long as it
doesn't interfere with school."


Jackie gave me a friendly punch in the ribs. "You sound
just like my parents. Isn't college about having fun?"



"That's probably why they're letting you
stay with me. They're expecting me to watch out for
you. But I promise that I'll give you your space and
privacy. And college is about having fun, but there have
to be times when you say to yourself "Tonight, I'm
gonna study."


"Yeah, I guess you're right, " Jackie
said.


Just then, Chris's car pulled up the driveway. "Jer,
over here!" he shouted to me as he rolled down the window.



Jackie laughed. "He's probably gonna give you
the If-you-touch-my-sister-I'll-kill-you speech.
I'm going to go finish packing." With that, she
went back into the house.


Chris got out of his car and stood in front of the hood. "Hey
man, what's goin' on?" I said, shaking his
hand. I hadn't seen Chris or Jackie since last Christmas,
when I was home.


"Hey Jer, not much. I've gotta be at work in half
an hour. I just came by to see if you and Jackie were gone yet."



"Jackie's just finishing packing up, "
I told him.


"Cool. Can I tell you something?"


"Sure, what's up?"


Chris began, "Mom and Dad trust you, and even though
I know you're no angel when it comes to chicks, I trust
you too. We know you wouldn't hurt Jackie, or be getting
her into trouble."


"Hey, Jackie's like a sister to me too. I think
you know that."


"I know, just let me finish, " Chris continued.
"I just want you to promise you'll watch out for
her, and don't let anybody lay a hand on her. Let's
not kid ourselves, Jackie's definitely growing up,
and a small town girl in the city needs someone watching
over her."


"Chris, I promise I'll keep her safe. I'll
watch out for her like she was my own sister." We shook
on that, and then Jackie came out of the house.


"Jeremy, I'm ready!" she called out, her
bags behind her. Chris and I helped bring her bags to my car.
When the last bag was in the trunk, Chris gave Jackie a hug
and said, "Be good, understand?" then got back
in his car and left. When he was gone, Jackie and I pulled
out of the driveway and headed for my place in the city.


When we arrived inside my apartment about an hour after
leaving Jackie's place, I explained to Jackie how
the intercom system works and showed her around my apartment.
I told her I'd have a key made up for her the next day and
showed her where her room would be.


"So this is your love nest, eh Jeremy? Quite the place
you have here, " Jackie said, flopping down on the
futon that would serve as her bed for the next eight months
or so.


I laughed. "Well, I don't know about it being
a love nest, but it's comfortable, close to downtown,
and affordable."


Jackie smiled. "Ah, don't be so modest. I bet
you've had dozens of girls up here. Can't say I
blame them, if somebody brought me to a place like this,
I'd be his slave."


Now I knew why Jackie's family wanted her staying here.
She definitely was growing up. I knew I was going to have
a challenge keeping her away from the predators around
town while still letting her live her life.


"You're exaggerating, Jackie. I've had
maybe three or four girls come up here. And when they saw
my photography stuff, they freaked out, thinking I had
lured them to my place to take naked pics of them. So even
if I wanted to, I couldn't get any more than a little
second base action."


"Oh, I almost forgot about your studio. Can I see it?
Or would I see something I shouldn't?" Jackie
said mischievously, a glint in her eye.


"Go ahead, knock yourself out. It's just down
the hall on your left." With that, Jackie bounded
out of the room and headed towards the studio.


Standing at the door of her room, I could hear her squeal
with delight. "Ooooh, I feel like a model. Ready when
you are, sir."


I went down the hall to see what the hell she was doing. When
I looked into the studio, I saw Jackie wearing a black bikini
and striking various poses in front of the camera. When
she saw me, she smiled. "Jeremy! I'm ready for
my photo shoot!"


My jaw dropped, and I thought to myself that if I'm not
careful, before long she'll be turning tricks on Main
Street and her family will never forgive me.


"Jackie, what do you think you're doing?"



"Don't you want to take pictures of me?"
she asked, pouting her lip.


"And have Chris or my family find them if they come
to visit? Are you nuts?"


"Well...can you at least take pretend pictures?
I'm feeling like a model right now, and I'd hate
this mood to go to waste."


"Well, all right; pretend pics only though."



So for the next little while, I pretended to be a big-shot
swimsuit calendar photographer, and Jackie did different
poses for me. While I was pretending to take pictures of
her, she was giving me very suggestive poses. Poses like
putting her hands over her breasts, or turning her back
to me with her bikini top undone, or sitting on the chaise
lounge with her right leg on the floor and her left leg bent.
I wondered if she would do these poses if there was film in
the camera.


Since there was nothing to do elsewhere, after dinner we
watched a little TV and I went over the bus schedule with
her, and told her where most of the stops were. A little while
later we turned in for the night.


We spent the next few days going around town. Since Jackie
was going to try out for the basketball team at school, we
played a little basketball down at the gym. She was quite
good at it, favouring lots of contact. I told her that if
she played like that in a game, she'd get called for
of fouls. She also got lots of looks from the guys when she
played, partly because she was a good player, but also because
she wore a tight grey tank top and black biker shorts. After
working out and playing basketball, we usually went shopping
or headed back home to watch TV.


Jackie's choice of wardrobe was certainly conducive
to getting noticed, no matter what we were doing. In addition
to her aforementioned basketball outfit, she usually
wore miniskirts or short Jean shorts when we went shopping.
And when we went out to dinner, she'd put on makeup and
do her hair just right. Often she wore her black mini-dress,
something a girl would wear if she wanted to get checked
out at a bar. Guys always looked at me in envy. I knew what
they wanted, and I knew that I had to make sure they couldn't
have it.


The Friday before school started, Jackie wanted me to take
her out to the non-alcohol nightclub that I work at. Actually,
she wanted to go to a dance club downtown, but she was underage.
Plus some of the spots downtown attract an unsavory crowd,
so I wanted to keep her away from that. I told her when she
became of age on her next birthday (which was in a couple
of months), I'd take her downtown to one of the better
clubs with the well-behaved clientele.


That day, I had a few photo appointments to take care of,
so I gave Jackie some money for her to go pick up her school
uniform. I have to admit it was hard to concentrate on my
appointments while thinking about Jackie in her uniform.
The appointments themselves were rather dull; there were
two little kids who couldn't sit still for five seconds,
a girl getting her pictures done on her 13th birthday, and
a brother and sister whose family wanted photos to give
to their parents on their 50thanniversary. Like I said,
pretty dull, but they made me some good money.


Twenty minutes after my last session, Jackie came home.
She was wearing her uniform. She was an absolute knockout
in her white blouse, grey knee-high socks, black Mary Jane
shoes, and the piece de resistance, her plaid skirt, which
barely covered her ass and was worn much higher than it was
supposed to be worn. She had also bought a few pairs of stockings
and a pair of hi-heel shoes.


"Well, how do I look?" she asked, showing off
her uniform, from both the front and back.


"I like it, but you definitely can't go to school
with your skirt that high. The principal will send you home, "
I replied. "What's with the stockings?"



"For days when I don't want to wear the socks.
They itch like hell. Also, I can wear them when we go out, "
she explained.


"We?" I asked. "Who's ' we'?"



"You and me. You know I'm not supposed to go out
alone, and I plan to go out a lot. I like it here."


"I see, " I said. "As soon as you change,
we can go to the club."


"OK, what should I wear?" she asked me.


"Wear whatever you like, it's a casual place."



"But you've gotta pick something for me to wear, "
she insisted.


I joked, "Wear your tightest miniskirt, pulled up
just below your ass, with your white blouse unbuttoned
to show some cleavage, and those black stockings you bought
today."


"And underneath?"


I couldn't believe she was taking this seriously.
"Black thongs and matching bra."


"OK, I'm off to change, " she said. "No
peeking."


"I was only joking!" I called out, but her door
sounded shut.


A few minutes later, Jackie came out wearing exactly what
I told her, in exactly the same style I told her to wear it.
She even flashed me her bra strap and the top of her thong
to confirm she was wearing the underwear I told her to wear.



"Are you ready, handsome?" she asked me.


I couldn't speak for a second. "Uh, yeah, let's
go, " I stammered. We got into my car and drove to the
club.


We were there for about an hour before the place began to
fill up. Jackie and I were at our table when Gail and Angie,
two gorgeous girls whom I had known (and had fucked, but
I didn't tell Jackie that) came over to us.


"Hi Jeremy, it's good to see you again. Where've
you been? You haven't called, " Gail said flirtatiously.



"Hi Gail. Sorry about that, but I've been busy.
The photo shooting has been picking up lately, "
I replied nervously.


Angie looked at Jackie and said, "I bet he's been
busy, the stud. Hey Jeremy, who's the chick?"



"Jackie, this is Gail and Angie. Girls, this is Jackie,
my--"


Jackie cut me off. "Girlfriend...I'm his girlfriend, "
she finished for me.


I couldn't believe she had said that. I looked at Jackie,
while Gail and Angie looked at each other.


"You have a girlfriend?" Angie asked incredulously.



"I can't believe that, " Gail echoed Angie's
sentiment.


"Oh yes, and who wouldn't want to be Jeremy's
girlfriend?" Jackie said, wrapping her arms around
me. "He's smart, funny, and SO good looking.
I was putty in his hands."


I couldn't say anything; I could only manage a weak
smile. Gail and Angie talked amongst themselves for a few
seconds, then looked back to me.


"I can't believe you're settling down.
A lot of girls are gonna be disappointed, " Angie
said with a sigh.


"Better watch him, Jackie, " Gail cautioned.
"He's a tiger. Come dance with us later, Jeremy?"



"Oh, he'll be around. Can't take the tiger
out of him that easily. Let's order a drink, honey, "
Jackie said to me.


"I'll be around, " I confirmed weakly.
"Later, girls." And with that, Gail and Angie
left. I turned to Jackie and asked, "What was all that
girlfriend jazz about?"


Jackie smiled and said, "Well, I'm a girl, and
I'm your friend. That makes me your girlfriend. And
besides, don't you know that you're much more
attractive to females when you're unavailable. But
anyways, don't let me cramp your style. I'd like
to look around a bit by myself. OK? Don't worry, I'll
be good."


"Sure, come find me when you want to leave, "
I instructed as Jackie got up to leave.


Over the next few hours, I mostly hung out with some of my
friends, dancing and watching the chicks go by. From time
to time I caught a glimpse of Jackie, always chatting with
someone who knew me. Periodically she looked over at me
and smiled, like someone had just told her a juicy secret.



Around midnight, Jackie came and got me and said she wanted
to go home. During the trip home, she was noticeably quiet,
which was a change from her usual self. I wondered if she
had heard something at the bar that soured her opinion of
me, but I didn't press her for it.


When we got home, Jackie grinned at me and said, "I
found out a lot about you tonight, Jeremy. I guess I shouldn't
be surprised, but it's nice to find out about the real
you."


I didn't have any idea what she was talking about. "Jackie,
you've known me since you were four years old. Aside
from Chris and my family, you know me better than anyone."



"I only know you as Chris's friend though, Jeremy.
95% of the times I've seen you, you've always been
with Chris. I learned more about you tonight than I have
in the last fifteen years."


I don't know what Jackie could have possibly been told.
I knew everyone that I had seen her talk to, and none of them
would have trashed me to her face. So I decided to play along
with her.


"OK Jackie, what did you find out about me?"
I asked, with a nervous smile.


Jackie stretched out on the sofa, making herself comfortable.
"You've had a lot of girlfriends, haven't
you? Angie was right when she called you a stud."


She was right, I had never lacked for female companionship,
but I didn't want to brag to Jackie about it. "A
few, but no more than an average guy my age."


"Bullshit, Jeremy. Don't be so modest. Every
guy I talked to envied you, and every girl I talked to wanted
to be with you. Rob, the bartender, couldn't get over
the fact that you boned two Swedish exchange students a
year ago."


I couldn't believe Jackie had gotten that information.
I thought back to Elisabeth and Anna, two girls from Sweden
who were exchange students at Algonquin last year. I had
met them at the bar and struck up a friendship with them.
I had had sex with Anna first, and then when Elisabeth found
out about it, she came to my apartment and demanded that
I fuck her as well. With her long blonde hair, blue eyes and
big tits, it was easy to say yes to her request. I fucked both
of them on and off throughout the school year and the night
before they left to go back to Sweden, they both came over
and we had a threesome. It was the best sex I ever had.


I brought myself back to the present. "How did you
get all this information?" I asked. "If everyone
thought that you were my girlfriend, why would they tell
you all that? Weren't they concerned that you'd
hold it against me?"


"Oh, I just told them that you didn't really like
talking about your past loves, that you were scared I'd
be upset. I told them that I didn't mind about what I'd
hear, that your past was in the past." Jackie sat up
straight on the couch. As she talked, I noticed through
her blouse that her nipples were becoming erect.


She then started to ask questions. "How many times
did you fuck Elisabeth?"


I figured I should be honest. After all, Jackie knew a lot
already, what more harm could be done?


"Once a week, " I replied.


"And Anna?"


"The same. Elisabeth on Thursdays, and Anna on Fridays."



"Which one had the better body?"


"Elisabeth had bigger tits, but Anna had longer legs."



"Which one was wilder in bed?"


"They both were pretty wild, almost like they were
twins."


Jackie kept asking questions about the Swedish girls,
and about all of my other conquests that she had found out
about: Did I love them? Did they give good head? Were they
shaved? What did they wear? After learning everything
she wanted to know about each girl, she always asked the
same question: "Was she better looking than me?"
It's hard to answer a question like that, but I managed
to be diplomatic about it. Or at least I thought I did, because
Jackie didn't seem to be upset about the answers.


After telling her every sordid detail, I half expected
Jackie to be disgusted and call her parents to come get her.
But Jackie didn't seem to be mad. In fact, after hearing
some of the most X-rated details, she began to fidget on
the couch, as if she was getting more and more aroused. Her
nipples perked up even more, her legs crossed and uncrossed,
and she played with her skirt.


"Jeremy, " Jackie looked me straight in the
eye, "how come you never hit on me?"


I didn't know how to answer that. After thinking about
it for a while, I replied, "Honestly, Jackie, I never
even thought about hitting on you."


"Why not? Is it because I'm not pretty enough?"
She looked almost ready to cry. "Don't you think
I'm hot?"


I felt myself getting flushed. "No, that's not
true at all. I think you're very pretty, " I answered
nervously.


"Then why not?" she persisted. "Is it
just because I'm your best friend's little sister,
is that all it is?"


"More or less, " I managed to reply.


"Why did that stop you? Many of Chris's friends
have flirted with me, have hit on me."


"I was scared, I guess. Scared that my friendship
with Chris, and my friendship with you, would be strained
if we dated and it didn't work out. I didn't want
that to happen."


Jackie stayed quiet for a few moments then looked at me and
said, "Jeremy, you're really one in a million, "
and gave me a kiss on the cheek.


After that discussion, we watched TV for a bit, and then
we turned in for the night.


When school started, Jackie soon became busy with homework
and after-school activities. I started doing a lot more
business with my photography. I was surprised, and pleased,
that my work was attracting a lot of exotic dancers, who
needed lingerie pictures taken of them for advertisements
at the strip clubs. The college crowd was back in town, and
the clubs figured they'd be doing a lot more business.
It was a treat to look at them, but working with them was purely
professional.


Jackie decided not to go out for basketball. Instead she
went out for the cheerleader squad. I was a little concerned,
because Jackie had heard at the bar about my fucking the
head cheerleader, in full uniform, after a practice. But
Jackie told me that basketball was just for fun and that
she preferred cheerleading. Two of her school friends
were already on the squad. When she got her blue and baby
blue cheerleader uniform, she complained that her skirt
was too long, of all things.


Jackie was a good student, and her grades reflected that.
But her accounting mark wasn't where she wanted it
to be, and since I had done well in accounting when I was in
school, I offered to tutor her one night.


After dinner and after the dishes were done, I asked her,
"Are you ready for tutoring?"


"Yes, just let me get my book and I'll be ready, "
Jackie replied and went to her room.


When I went over to turn the TV off, I saw her books on the coffee
table. I called out to her that her books weren't in
her room, but she either didn't hear or chose to ignore
me. A few minutes later, she stepped out of her room, and
for some reason, she was in her school uniform, with her
skirt pulled WAY up and the top two buttons of her blouse
undone.


"Jackie, what's with the uniform?" I asked,
a little irritated.


"I'm just ready for my tutoring, professor, "
she said with a giggle.


"Since when do you wear a uniform for a tutoring session?"
I retorted.


"Oh, come on, Jeremy, it's more fun this way."



Since telling her to change wasn't an option, I sighed
and we got down to business. Although the way she wore her
uniform made me believe otherwise, Jackie took the tutoring
seriously. Once in a while, though, she would uncross her
legs, as if she wanted to flash me her panty-covered crotch.
Every time she did this, I tried to hide my erect cock from
her, although I couldn't tell exactly what panties
she had on.


After that, sometimes she would come home from cheerleading
practice and insist on showing me the routines she had learned.
I told her I didn't care how she wore her cheerleader
outfit but if she was going to continue to wear her school
uniform for tutoring sessions, she had to wear it according
to the rules of the school. It didn't really matter
how she wore that uniform either, I always got hard when
I saw her in it, or in anything else that showed off her legs
for that matter. The routines Jackie was doing were pretty
much repeated year after year, but Jackie's leg kicks
seemed higher than any other cheerleader's that I
could remember.


When she turned 19, I fulfilled my promise and took her to
one of the dance clubs downtown. She was still telling people
that she was my girlfriend, and I wasn't saying anything
differently. Sometimes I would joke with her around the
apartment that she was my girlfriend, and had to do whatever
I said. She usually laughed about it, but whenever I told
her to do this or that for her "boyfriend" she
always did it.


At night, sometimes I would hear muffled moans from her
room. At first I thought it was just sounds that she made
while sleeping, but one night, I crept to her room and peeked
through the door. Although I couldn't be sure, since
her back was to me, I believed that she was fingering herself.
It got me so hard that I would try to catch her doing it almost
every night. One night, after she had fingered herself
to orgasm, I watched her take her two fingers out of her pussy.
They were drenched in her cunt juice but instead of wiping
them off, she put them in her mouth and licked all the juice
off. When I got back to bed that night, I whacked off until
my arm hurt and my dick was feeling raw.


The following Saturday, I was watching a hockey game on
TV, when Jackie called out from her room. "Jeremy,
come here right now!" I rushed to her room thinking
something was wrong, that she was sick or had received some
bad news.


I got the shock of my life. Jackie was lying on her bed, wearing
only a black lace teddy that barely came to the top of her
legs. If she had opened her legs, I would have seen her pussy.



Jackie sat up. "Jeremy, I can't take it anymore,
I want you to fuck me and fuck me hard."


"Wh-what was that? Did you really ask me to...?"



"Yes, Jeremy. I want you to fuck my brains out."
Speaking, she opened her legs and sure enough, I got an eyeful
of her cunt. I was too stunned to look away. She was trimmed,
but not completely shaved. She went on, "I know you've
fucked some real sluts... Well, I can be a bigger whore than
any of them. I'm a virgin, but I want my first time to
be with you. If you fuck me hard enough, I'll bleed all
over for you. I know you'd like that."


"Jackie...I can't--"


"But, Jeremy, you HAVE to! You're the only person
I can trust when it comes to that." She came to me and
held me tight with one arm while her other hand reached down
to feel my cock and balls. "Your dick wants it, you
have to fuck me."


"I can't Jackie, I promised your parents I'd
never hurt you."


"If you don't fuck me, Jeremy, I'll go downtown
for it. Then what will they say?"


She was right, of course. And I couldn't let a stranger
fuck her. It would be like someone taking advantage of my
own sister.


"OK, you've made your point, Jackie."



"You'll fuck me then?" she asked, eagerly.



"Let me think about it. I'll let you know when
I've made my decision." I wanted to make sure
to myself that if I went through with this, that I wouldn't
regret it, and that I could live with the consequences.
Jackie was definitely growing up and aware of her sexuality.
It seemed she was determined to lose her virginity one way
or the other. If it wasn't with me, it would be with somebody
else, and there's no telling what she might pick up.



For the next few days, Jackie's request was all I could
think about. I couldn't deny she was a great looking
babe, and living with her had given me the opportunity to
see that. No longer was she just a friend's kid sister,
the girl I used to make spit bubbles with. After all, the
only time we had even kissed was when she was nine years old
and dragged Chris and I into a game of kissing tag with her
and her friends (when our friends got wind of it, they didn't
let us forget about it for a long time). And we certainly
weren't kissing the way she wanted to kiss now.


But at the same time, Jackie was still first and foremost
my friend's little sister. And it's never easy
to even date your buddy's sister, let alone fuck her
brains out, like she wanted. I was scared that if we had sex
and Jackie was disappointed, or worse, hurt, the whole
thing would irrevocably backfire. The kind of sex she sounded
like she wanted didn't suggest she was into "making
love, " so maybe Jackie just wanted my body. But if
that was true, I wasn't sure if I could deal with that.
I thought that I would want to have something more with Jackie,
and if she wasn't interested, she would just walk out
of my life forever.


To take my mind off this for a while, I went to my studio and
did an equipment check, as well as develop some photos that
needed to be sent to clients. During my check, I noticed
I was running a little low on film, so I needed to place a call
to a supplier. When I picked up the phone, however, instead
of the dial tone, I could hear Jackie talking with someone,
a male voice.


I couldn't make out the voice at first, but I soon realized
it was a guy named Nathan. I shuddered. Nathan was a great
guy, but women were weary of him. I had seen Jackie talking
with him when we went out on her birthday.


"Has he fucked you yet?" I heard Nathan ask Jackie.



Sarcastically, she replied, "He wants to think about
it. What a gentleman."


"Well, he doesn't know what he's missing.
If he doesn't fuck you, give me a call. I'll show
you a real good time." When I heard that, I swore that
if he were in front of me right then, I'd have flattened
his ass.


I couldn't take any more. I hung up the phone as fast
as I could. I couldn't let Nathan fuck her. Especially
Nathan. I knew his reputation. Like I said, he was a great
guy, but a real asshole when it came to women. If he got to
Jackie, he'd fuck her and then trash her all over town.
Everyone would think she was a slut, then they'd all
come after her. It would be all over school as well.


Hearing that phone call made my mind up. A part of me had wanted
to make this decision all along. I would fuck Jackie, if
it would keep everyone else away.


I waited for Jackie to hang up the phone. Then I went to her
room. She was wearing a sleeveless vest with hip hugger
jeans. It didn't look like she was wearing a bra.


"Well, have you made up your mind yet?" Jackie
asked eagerly.


"All right Jackie, I'll have sex with you. But
there are some conditions. You can't tell anyone.
Understand?"


"I'll keep it a secret. Anything else?"



"You can't let anyone else fuck you. To expect
that we would only have sex once would probably be naïve.
If you're really horny, come to me. I'll get you
a dildo for when I'm not around or busy in the studio."



Jackie's tits perked up when she heard this. "Will
you use the dildo on me?" she asked.


"If you want. And the last condition is, I'm going
to treat you like any other girl. You're going to get
it hard. You'll probably get it in every hole, and that
includes your ass. Are you sure you're comfortable
wi--"


"Jeremy, I'll do anything you want. Just fuck
me and fuck me hard."


We went to my bedroom. I closed the door behind us and took
Jackie down on the bed. I slowly unbuttoned her vest and
let it fall to the floor. She wasn't wearing a bra, and
her tits were even bigger and better than I had imagined;
I'd say she was close to a D cup bra size.


Jackie lay back on the bed. I gently flicked my tongue across
her nipples to get them hard. Then I took them in my mouth
one by one. She moaned and squirmed, putting her hand down
her pants to finger herself. I placed my hand on her wrist,
just above her belt. I didn't make her stop fingering
herself; I just wanted to control her, to make sure she didn't
cum too soon.


When I got her nipples as hard as I could with my tongue, I
told Jackie to sit up on the bed. I stood in front of her and
brought her hand to my zipper. She undid my jeans and slid
them and my boxers to the floor. My cock was right in front
of her mouth. She licked her lips and her hand reached for
it. I stopped her and instead, took off her jeans and tossed
them aside. She wasn't wearing any panties, and her
cunt was smooth and, surprisingly, shaved. It was as if
she had known that I would eventually fuck her and had prepared
herself for me.


Jackie's hand instinctively went to my cock again
and this time I didn't stop her. After only a few moments
of her stroking, I was rock hard.


"You want me to suck your dick, Jeremy?"


"Yes. Suck it, Jackie.


"Not until you call me a bitch."


"Suck it, bitch, " I hissed. The name-calling
got her turned on even more, and she immediately engulfed
my cock in her mouth.


The feeling was unbelievable. Nobody had ever sucked my
cock as good as Jackie was doing right then. She played with
my balls while deep-throating my cock. I couldn't
believe how good she was at it. I asked her if she was sure
she hadn't done this before.


"Only with a banana and a Popsicle, " she told
me, then continued right on sucking.


It was amazing. Whenever I told her she was a slut or a whore,
she echoed my words. Listening to her call herself a dick-hungry
slut, a schoolgirl whore made me want to jam my cock deeper
down her throat. At that point, I was getting close to the
edge, and hoping she would let me cum all over her face.


After thoroughly licking and sucking my cock, Jackie took
it out of her mouth and started jerking me off. She asked
me where I was going to cum. I decided to be cautious and told
her I hadn't made up my mind yet.


"I want it on my face. I'm your whore, treat me
like one and spray all over my face."


That did it. I couldn't hold back any longer, and blew
my hot, creamy load all over her face. Taking care not to
get any in her eyes, I sprayed over her forehead and chin.
She stuck out her tongue and I squeezed the last few drops
onto it, and she swallowed them.


I got up to get her a towel, but she pulled me back down on the
bed. She told me that she wanted me to fuck her with my cum
still all over her face. The request was enough to get me
hard again, and I told Jackie to turn around and grab the
headboard. Virgin or not, I wanted to take her from behind,
promising myself I would be gentle in her initiation. But
Jackie was wild, and too exciting to leave any room for the
word "gentle."


She was real tight, definitely a virgin, but I slipped in
fast and hard. When I told her she was only shedding a few
drops of blood (normal for most girls), she was disappointed.
She had wanted to bleed all over.


By this time, I had also gotten over the fact that Jackie
was my friend's sister, and I was treating her like
I would any other girl. I was getting into slapping her ass
(the best ass I'd ever seen) while plunging my cock
deep inside her snatch. She screamed almost constantly,
and fingered herself to orgasm more than once. With her
pussy absolutely drenched in her juices, it was easy to
fuck her as hard as I could even though her cunt was tight.



I couldn't believe how long I was able to hold out. After
what seemed like an eternity, I pulled out of her pussy and
quickly flipped her over onto her back. As I squirted all
over her boobs, she rubbed my cum into her nipples with her
hands, keeping her nipples nice and hard.


I thought for sure that at least one of us would be exhausted
by now, but after only a few minutes, Jackie was ready for
more. She wanted me to fuck her ass. I warned her that it probably
would hurt, that her ass was even tighter than her pussy
and wouldn't be as wet. Jackie's response was
to turn and get on all four's, doggy style, assuring
me she was ready and that she could take the pain.


I kneeled behind her and started to push my dick into her
ass slowly, so it wouldn't hurt her as much. Jackie
was unimpressed. She demanded that I shove it in and fuck
hard. When I tried to protest that it would hurt, she gave
me the order, "Just fuck my asshole, Jeremy. HARD!"
and it was useless to protest. No girl I had ever had had wanted
her asshole fucked as hard as Jackie did. Whenever she screamed,
she assured me that she was screaming because it felt so
good. I didn't know if she was telling the truth, but
for some reason, her screams would just make me fuck her
asshole even harder than before. It didn't take me
long to cum. I pulled out and shot my wad all over her hot ass.
It wasn't as big a load as the first two, but it felt just
as good nonetheless. I watched Jackie reach back and rub
my cum into her ass cheeks, then we both dropped on the bed
exhausted.


When we had recovered a bit, Jackie turned to me and asked,
"Am I the best pussy you ever had?"


I replied, "Definitely one of them. The best at giving
head and taking it in the ass, that's for sure."



Jackie smiled. "I hope we'll be doing a lot more
fucking."


"I think I can arrange that, " I replied.


So except for when we have company, Jackie sleeps in my bed.
I let her pick out a dildo to use when I'm unavailable
and she loves using it. We fuck every night, except when
she's having her period. To my surprise, and delight,
whenever she menstruates, she brings home one of her friends
from school to entertain me, as she wants me to get laid at
least once every day. Since I confessed to her that I always
get hard whenever she wears her school uniform or cheerleader
outfit (hell, I get hard no matter what she wears, but I seem
to be hardest when she wears either of her uniforms), she's
taken to wearing them a lot more around the house, either
without panties, or with G-strings underneath. She loves
bending over, having me lift up her skirt and plow either
her pussy or her ass while still fully dressed. I ordered
more photo equipment and we started taking our own X-rated
photos. One of my favorite sets is of Jackie fingering herself
to orgasm, then taking the dildo and doing it all over again.
We role-play a lot, with Jackie playing numerous roles;
from a cheap prostitute to an auditioning porn star to my
sexy, somewhat slutty secretary.


Sometimes, for a special surprise, Jackie brings home
another girl even when she isn't on her period. We go
to the bedroom and Jackie makes me watch her eat her friend's
pussy before I can get in on the action. Sometimes I tell
her that she loves eating pussy more than sucking dick,
but she insists that there is room for both in her mouth.



With the semester ending, and Jackie returning home, I
don't expect to get as much action from her as I would
like. Even though I'll be spending two weeks at home,
close to her, around Christmas, I don't think we'll
get to spend a lot time alone together. Jackie's promised
me, though, that she'll find time to at least give me
a quick blowjob, even if we don't get around to fucking.
She's also promised that when school starts again
in January, she'll make up for it. She's told me
she's planning a surprise for my next birthday, which
is a week after school starts. I don't know what it is,
but if Jackie's planning it, I'll need all the
strength I can get, because I have a pretty good idea what
it involves.

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Member Responses Post Your Comment

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tell us what happens next

6/14/2008

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WHAT HOT GREAT TALE THANKS.

6/14/2008

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I think you could have reached the main point of your story
quite sooner than you did. Very slow and not all that good
readin in the beginning, makes people lose interest.

6/15/2008

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yes...its very nice, but could have resumed at the beginning.

6/25/2008

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Nothing like a family friend, eh?

10/1/2008