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SSS1 hurt worse that had


1ЙФнTФххххХиShort story Series SSS1.txt by JS3729


# 1 - Loving the Babysitter (mf (teen) MF rom, love) (part 1 of 2)

============================================================= This is
the first of a series of short stories I am writing on specific themes.

This one deals with the realization a young teen has that his babysitter
is his perfect woman, and then how he deals with a tragedy.

Please let me know how I am doing.

I am now archived in ASSTR - The Alt.Sex.Stories Text Repository Please
check my other stories out and all of the other great authors there. It's free and well worth the time.

I first met Eileen in high school. They say that there is no such thing
as love at first sight, but I have to tell you that I fell for her at first
sight (and second, and third). The problem was that she was a senior and I
was a lowly sophomore. She also was a cheerleader and probably the most
popular girl in school. She had many boyfriends and she was always in
demand for most school functions.

Yes, I was in lust with Eileen, but it was from afar. At the time, I
had no real idea what *love* was, but I knew I wanted to fuck her, and I
wanted to fuck her bad. I would jack off at night trying to imagine the
different ways I could screw Eileen if I only had the chance. But I knew
it would never happen. She would be going to college next year, and I was
stuck here for two more years. Also, she didn't have any idea who I was. I
was just a sophomore - just someone to put up with until she could be free
of these underage fellow students.

Eileen was stuck-up. There was no other word for it. If you weren't a
senior like her, you were beneath her. I don't think she ever spoke to
underclassmen the whole time we were in high school. Many juniors and even
a few daring sophomores had attempted to ask her out on dates, but she just
ignored them. They weren't even worth the effort to say NO to.

I had an ally in getting to know Eileen, though. My older sister,
Jennie was Eileen's best friend, and unlike Eileen, Jennie was friendly and
compassionate to the underclassmen. In fact her boyfriend Todd was a
sophomore like me. Eileen couldn't understand how my sister could lower
herself to go out with an underclassman. Jennie just told Eileen that a
boy was a boy no matter what his age was. Privately, I envied Todd like
hell. I wished I could make Eileen feel the same way about me.

Jennie realized that I was hung up on Eileen, and she did her best to
make Eileen see what a catch her little brother could be. Eileen was
having none of it though.


My folks have five children, of which Jennie and I are the two oldest.
Sometimes, they need to get a babysitter for my younger brothers and
sister. We normally get old Mrs. Graham, but she had recently passed away,
and my parents had to attend some kind of company function. They were
scouring the area for babysitters, but none were available on short notice.
My sister, who would be out on a date and unable to babysit, found a
somewhat willing candidate at the last moment. My folks were relieved and
they agreed to the sitter sight unseen. Jennie wouldn't tell me who it was
just saying that I knew her. I was going through all the girls I knew that
sit, but none of them knew Jennie that well.

So imagine my surprise and delight to find out the sitter was Eileen.
Eileen was finally in the same building I was. Jennie was in the front
room when Eileen came to the door, and she answered it. Her date (Todd)
pulled up behind Eileen's almost new car and Jennie gave me a wink and
left. (Thank you sister! I owe you a big one!!!) Eileen took one look at
me and fixed her superior stare on me and went to find the younger kids. I
was still a bit in shock, so the stare had no real effect on me. About a
half hour later, she returned from the back with my little brother Aaron.
Aaron was a junior size babe magnet at fourteen and he had most of the
girls in junior high falling all over him. I saw Eileen leading Aaron out
to the bathroom literally dragging him by his hand.

"This little twerp was jacking off in his bed. I won't have that while
I'm sitting. I'm going to fix that problem for tonight" She had grabbed
Aaron's belt. Eileen was furious and Aaron was terrified. I knew I had to
do something, or my brother could be scarred for life.

"Eileen, listen to me - what he was doing was natural. He didn't do
anything wrong. Let him be." I knew I had blown my chance to get to know
Eileen better, but my brother was more important at that time. Get rid of
that belt. You're just sitting - it's not your place to discipline him
anyway. Give me that" I grabbed at the belt she was holding, and missed
and grabbed her blouse instead. It gave with a tear and her bra popped
into view. Aaron was gaping and his mouth was drooling. I wasn't in much
better shape, but I was still angry, so I wasn't hard like Aaron was.
Eileen noticed and she got madder.

"See, he's doing it again. Stop that. You're just a kid, you shouldn't
be doing that."

I finally got the belt away from her, and threw it into the living room.
I told Aaron to go back into his room and go to sleep. I would talk to

"Eileen, what the hell do you think you're doing? You're supposed to be
sitting us kids, and not trying to be our parents. I hope you didn't wake
the younger kids up with your yelling. Why don't you go up and see. I
want to talk to you later." I was not really sure what I was doing, but I
was still mad, and Eileen's torn blouse was beginning to have an effect on
me. I was getting hard.

Eileen blushed (huh???) and went back upstairs to check on my younger
siblings. I stopped by Jennie's room and fished a blouse out of her
closet. I figured I should at least let Eileen cover those juicy tits of
hers up (I really wished the bra would have ripped too)

Eileen came back down about five minutes later. "Aaron is sleeping now,
the others never woke up, thank God. Look. Sam, I'm sorry about exploding
like that - I saw him jacking off, and I just reacted. Please forgive me."

I was stunned. This was the last thing I expected Eileen to say. I
threw Jennie's blouse to her.

"Better change into this. I don't think your old one is any good now.
(I also didn't think I could keep from staring at those creamy tit mounds I
saw around her bra)

Eileen grabbed the blouse, shrugged out of her ruined blouse and put
Jennie's blouse on. It was too small for her large tits, and that seemed
even more erotic that her torn blouse was. "This is too small for my boobs - do you have any larger ones?"

"Sorry. Jennie's got the biggest set in the family. My mom is very
small, and my other sister is only eleven." I couldn't believe I just said
that to my dream girl. I was blushing like mad, and my pants were now
about two sizes too tight.

Eileen looked down. Jennie's blouse was stretched so tight, that the
buttons were gonna pop any minute. She sighed and removed it again.
"Better take it off. I don't want to ruin any of Jennie's clothes. I hope
you won't mind. I'll just wear the bra." She kinda laughed and smiled.

What was going on here? Ten minutes ago she was ready to whip my
brother's ass for jacking off and now she was sitting across from me with
just her bra on. My cock was at full mast and I was trying to find a
comfortable way to sit. I couldn't. To my horror (and secret delight)
Eileen noticed. Oh God, where was that belt? I sure as heck didn't want
the same punishment my brother was going to receive. Eileen just sat back
on the couch and smiled again, but this smile was different. Was that
arousal I was smelling? Nah, couldn't be.

I was wrong.

Eileen leaned over and whispered in my ear "Jennie told me how you feel
about me. I think I feel the same way. Let's find out together." She had
a look of lust on her face and began to remove the bra.

Talk about being in shock!! I just made little unitelligible sounds and
I was shaking like a leaf. This had to be the best wet dream I had ever
had. My brain was telling my to find that belt before she did - maybe she
still wanted to whip some ass.

Eileen had the bra off, and I got my first look at paradise. Eileen had
two of the biggest and most perfect tits I had ever seen (all right - only
the second set I had ever seen - I caught my sister in the shower one day,
and got a frontal shot. Hers were very tiny, but still sexy.) Her tits seemed to be beckoning me to suck them and Eileen slid over to me and put
her hand on my crotch. My rock hard dick was painfully obvious. I have a
decent size 7 inches and all of it was pressing against my pants and I had
an embarrassingly large stain on my blue jeans. Eileen noticed that too.

"Oh yes, that looks delicious. My I have a taste?" she purred into my

"Please" I was beyond caring now.

She reached to my pants, unzipped me, and took my hard tool out. She
was drooling.

"That's the largest one I've ever seen. I wonder how it tastes..." and
she took me into her mouth. It was esquisite. I had never had feelings
like that before and I was floating. She really knew what she was doing
and I could tell she'd done this a few times before. I was soon ready to
cum, and I warned her. She just grinned around my dick and waited. I shot
and shot and shot and she took as much as she could. She then licked up
the excess. and sat back on the couch with a satisified expression on her
face. She looked at me and gave me a warm smile. In that moment I knew
what love was. I was in love with her.

"Eileen, I don't want to sound ungrateful, but why? You always treated
me like dirt. Why are you suddenly interested, now?"

"Sam, when Jennie told me about you, I laughed it off as usual. I mean
most of the boys in school feel the same way you do. I figured you were
just like them and I appreciated the interest, but I *was* a senior, after
all. I was too good to go out with a mere sophomore. Then I saw how Todd
treated Jennie. I saw how much they wanted to be with each other, and I
had never had anything like that in my other times. Most of my dates want
to fuck me - the only thing they seemed to care about was how many dates it
would take for me to put out. I hated that, but I thought that was what
dating was about. I even dated a couple of girls. I thought maybe it was
just boys that were making me feel like I was being used, but girls were
even worse, and I never did cum with any of them."

"I'm not like that. I mean I fantised about fucking you too - every guy
in school has, but we know it won't happen. I guess that makes it safe."

Eileen chuckled (that sounded like music to me) "Kind of nice to know
that, but I'm not surprised. I began to watch you during school, and I
liked what I saw. You are always kind to everybody and you truly care
about what other people feel. I began to wonder why you didn't have a
girlfriend of your own. You're a heck of a catch."

"I couldn't think of being with anyone but you. I've felt that way
since the first time I saw you."

"Love at first sight, huh? I never thought there was any such thing.
Maybe I was wrong. Anyway, I finally started to realize what kind of
person I was becoming. I was a snob, and I didn't like me much. In case
you're wondering, I begged Jennie to let me sit tonight. I wanted the
chance to talk to you alone away from school. When I saw Aaron jacking
off, I saw his dick and I wanted him. Then I remembered why I was here,
and I was furious with myself. The anger with Aaron was an act - I wanted
to see how you would react. You proved my hopes right - you are a person
of integrity, and I want to get to know you better. A LOT better" and she
gave me a sexy smile.

My dick was harder than it was before, but I knew I couldn't fuck her
tonight no matter how much I wanted to. I wanted a chance to know her
better too. I didn't just want a few good weeks or months of fucking. I
knew I wanted her permanently. I wanted her for my wife. I couldn't fuck
her until I knew I could have a chance to make that dream happen.

"Eileen, you don't know how much I hate to say this, but I can't fuck
you tonight even though I've never wanted anything so much. It just isn't
the right time. We don't know each other, and I can't fuck someone I don't
know. I know my body wants your body, but my heart wants your heart, and I
don't have that yet. If and when I do, then we can make love together. I
could never just fuck you."

I expected anger, or disappointment or a look of rejection. What I got
floored me.

"Sam, you just passed the last test I had for you. I would have screwed
you tonight, and it would have been the only time. I really want to fuck
you, but I don't love you" my heart sank and then she added "yet, but I
know that you're four times the man that I have ever been with. This is
not over by a long shot, but I will going to college in a few months. Do
you thnk we can build something that will last over time and distance? I'm
willing to try if you are."

By way of answer, I kissed her for the first time and I looked into her
eyes. "If there is to be an us, time and distance won't matter. I know it
doesn't to me. I just have to convince you. Now let me return the oral
favor, and we can call it even. I don't have the foggiest idea how to do
this, so please let me know if I'm doing anything wrong. I want to learn,
and I have the best teacher in the world to help me."

Eileen's look of wonder was replaced by a smile that I will remember for
the rest of my life. She undid her skirt and pulled the skirt and her
panties off in one motion. I wondered how many times she'd done this
before. I looked at her cunt and I was lost. She was gorgeous everywhere
it seemed. I began to lick without knowing where I was licking. I brushed
against some little bump and she went wild. She grabbed her torn blouse to
scream into and she got much, much wetter. I must be doing something
right. I continued licking and sucking whatever I could find to lick and
suck, and not once did she say anything to me other than to tell me not to
stop. I had no intention of stopping until she told me to. She finally
pushed me away after having so many orgasms that we both lost count. She
took my sopping face in her hands and licked our juices of my face, and
then fixed that smile on her face again.

"If that's a beginner, I can't wait until you're an expert." and then
she began to cry softly.

"What's wrong?" I was worried I might have done something that she
didn't like.

"Nothing is wrong, my darling (Huh??? She was calling me darling????).
I was just thinking of how much time I had been wasting with other people
when what I have been looking for was in front of me all this time." She
laid her head on my shoulder and said "I understand your reasons for not
making love to me tonight, but I think I feel like you did before I came to
my senses. I can understand what it is to want something but know that
it's not the right time. We have to give us a chance to build and grow,
before we become one. But I also know, that if tonight is any indication,
it won't take long."

Eileen left, but not before giving me the kind of kiss I'd only dreamed
about. She looked back at me and said "That's just a sample. The full
course will be coming".

Todd's car pulled up behind Eileen and he let Jennie out. He backed out
and drove off. Eileen blew me a kiss from the car and drove off too.
Jennie had a shit-eating grin on her face and followed me inside.

I turned to my sister and gave her a big hug and a kiss. I owed her

"What was that for, little brother? Thinks go OK here tonight?"

"You won't believe how well they turned out. I don't believe it

"So my brother has a girlfriend now, how?"

"No, your brother hopes he has his future wife." Jennie looked at me and


Eileen went off to college and we kept in touch. She dated and she
wrote me about each one. We had decided before she left that we would date
while she was in college to see if what we have together was stronger that
what we may find. Jennie was her roommate in college and she also wrote
me. She was still with Todd, and they were engaged. Todd and I had gotten
to know each other and became fast friends. We were both in the same
situation - we loved someone who was far away, and we were trying to keep a
long distance relationship going.

Jennie and Eileen came home on holidays and school breaks. Those were
very happy times for Todd and I, but something was missing. Jennie and
Todd used to fuck up a storm whenever my parents weren't home and the kids
weren't around. Eileen and I still hadn't made love yet, but we had done
most everything else.

At the end of my senior year in high school I was dating this girl Rhonda. I was doing it mostly to have someone to talk to. She was pretty
and we liked a lot of the same things, but I felt like a cad, because I
knew she felt something for me, and she wanted me to commit to her. I
couldn't do that. I was committed to Eileen, and I always would be. She
wanted to fuck me badly and she couldn't understand why I wouldn't fuck
her. I wanted my first time to be with the woman I loved, not a substitute,
and I wasn't being fair to Rhonda.

Rhonda finally got tired of waiting and went after Todd. This was just
as bad, because Todd was totally in love with my sister, and poor Rhonda
got shot down again. She finally called Jennie at the college to complain
about us. Jennie was aghast. She never knew Todd had dated Rhonda, and
she was a little mad. She also told Rhonda about Eileen. Rhonda came over
that night full of fire and was yelling from the moment I let her in. I
told her that I wanted a companion, nothing more. I was being cruel and it
hurt me worse that it had hurt me to let Eileen go back to college. This
incident made my mind up for me. I was going to see Eileen at the college and propose. I couldn't take not knowing any longer.

I called Jennie.

"Hi sis. I have to see Eileen. When would be a good night to see her?
I don't want to see her after one of her dates."

"Nice to hear you again little brother. Any night would be fine, Eileen
stopped dating six weeks ago. She said there was no use looking - she'd
already found what she was looking for. Anybody else wasn't worth the
effort. She was just waiting until summer break to tell you. What's wrong
that you have to see her?"

I told Jennie about Rhonda's reaction, and how that made my mind up
about Eileen. I told her I wanted to come up and propose to her. I
couldn't bear it if she found somebody else."

"You have nothing to worry about, Sam. She's more in love with you that
I am with Todd, and that's saying a lot."

"Great to hear that I'll be up there on Friday. Don't tell her please,
I want it to be a surprise. Just make sure she's there. I don't want to
propose to a picture."

"You bet, little brother. I'll tie her to the bed if I need to. By the
way, I can make myself scarce with the best of them, if you get my drift."

"Thanks sis, that's two I owe you now."

Friday finally arrived. Graduation had been on Tuesday, and I was free
of school. I was going to work for my father in his business - I didn't
have the grades for college. I arranged with Todd to cover for me if
anybody asked where I was. Todd was glad to help. Jennie had told him
what I planned. We had even decided to make it a double wedding
immediately after the girl's graduated from college.

As I pulled into the campus, I realized I didn't have any idea where to
find Jennie or Eileen. Jennie was ahead of me again, because she was
waiting outside the visitor's center for me.

"Hi Sam. Glad to see you bro."

"Good to see you again too, sis. Where can I bunk down?"

"Oh, I don't know - seems to me I've got an extra bed in my room, if you
don't mind sharing with my roommate."

"Thanks sis - that's three I owe you."

That night, I was waiting in Eileen's bedroom. Jennie had taken her out
for supper to celebrate our graduation from high school. She wanted to
tell Eileen that Todd and her had set their wedding date. She told me
Eileen started to tear up when she heard that. She said Eileen wished she
could set her date, too.

I heard them get back to room. Jennie excused herself, saying she
needed to call Todd, and then she had to study for finals with her study
group. She said she'd probably stay there all night. She left and Eileen
started for her room. I was sitting on her bed with a rose and a smile.

She opened the door, took one look at me and jumped into my arms. I was
ready and I kissed her hard. She kissed back and smiled. She took the
rose and blushed. She got up, got a glass of water and put the rose in the

I got up off the bed, knelt on one knee, and asked her the question.
She didn't say a word, she just began crying softly and kissed me tenderly.
She nodded her head and pulled me onto the bed. She began to undress me,
and I did the same thing to her.

She looked at me and said "Tonight, my love, and forever more."

Concluded in Part 2.

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