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From: "rache" <rache696@yahoo.com>
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Subject: {ASSM} Babysitter's First Time by Rachael Ross (M/f, First, Consensual)
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Date: Fri, 15 Sep 2006 01:10:01 -0400
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Babysitter's First Time
Copyright 2006 Rachael Ross all rights reserved.
Story Codes: M/f, Romantic, First, Consensual


Babysitter's First Time
by rachael

When I was thirteen I found a job babysitting for a friend of my
mother's. Her name was Charlene Watson and her husband was Charles,
which I always thought was a little funny. Everyone called her
'Charli' but her husband was always Charles and they were very
nice, especially to me and it seemed as if I'd known them my whole
life, really. They were more like my aunt and uncle than just
neighbors.

When I had a birthday, or some other special occasion, Charli and
Charles were always there, with gifts usually, even when it wasn't
called for. Like they gave me a new pair of roller blades just for
singing solo at the school concert when I was twelve. They always told
me they liked to spoil me because they couldn't have children of
their own.

But one day they did have a child of their own. A little boy named
Mason who didn't have any parents. He was almost 3 when Charli and
Charles adopted him and he was really cool. We spent a lot of time
together, naturally, because our families were close, and Mason seemed
like my little brother in many ways.

So it was only natural I suppose that when I turned 13 Charli wondered
if I wasn't old enough to babysit Mason once in a while. Of course I
was, I knew, and it excited me, but my mother wasn't so sure. She was
always very protective of me since my dad had died, or joined the
circus, or run away with a Mexican girl named Tequila, depending on
what sort of mood my mother was in when the subject came up.

"But I'd just do it once in awhile, mom!" I protested her
concerns.

"I just don't like leaving you alone, Janice." My mom told me.

"It's two houses down though!" I pointed in the general direction
of Charli's house, just in case mom forgot. "It's not like I'm
gonna be on the moon!"

That made my mom smile at least. "Of course not, I know that dear.
But..." She made a face. "I'll think about it." Which made me
smile cause in mom speak that was a yes, but for a lot of other girls
it was probably a no. I was glad I wasn't one of them!

And so I was babysitting, making five dollars an hour of my own money
and it was neat! Charli and Charles liked to go out on Friday and
Saturday nights, so that was mostly when I did it. They weren't all
that old, just 28 or something like that, except I think Charles was a
little older, maybe even 30, which seemed pretty ancient. He didn't
have any grey hair though, so probably just 29 maybe.

He was cute too. Charli was very pretty, but Charles was definitely
cute and I had just started to notice that. I thought about him
sometimes, wondering what it was like to be Charli and see him every
day. He was tall with sort of long brown hair, kind of scruffy looking,
but nice. He had green eyes, dark green too, and sometimes we would
have staring contests and I would just look in his eyes and kind of
forget it was a contest and blink. Then he would laugh and tousle my
long blonde hair.

Charli was dark and sometimes I thought she looked like a vampire,
sorta, but a good one. But who ever heard of a vampire named Charli
anyway? She had long, long black hair and very white skin. Charli's
skin was so white you could see the little blue veins even, and her
eyes were blue, which looked really cool. Bright blue too, but she
liked to put a lot of eye shadow and makeup around them. And lipstick,
really red lipstick. She told me she was the original Goth Girl and I
believed her. She even had tattoos on her shoulders, like big black
wings that almost covered her whole back and I'd wondered if she was
an angel when I was real little.

After about a month of babysitting my mom was finally comfortable
enough with it so that Charli and her husband could convince her to go
out with them once in awhile. They had always been asking my mom to
come with them, and I always wished she would, because I know it was
hard for her to be alone sometimes. I mean even with me there she was
still sorta alone.

My mom is very pretty too, but more like me, all blonde and tan and
smiling. She was 28 years old, but didn't look like it at all. At
least not to me. She looked more like she was 16 maybe, because she
dressed just like the girls I saw going to high school. In fact one
Saturday night when she was going out with Charli and Charles my mom
was wearing a schoolgirl outfit, a real one like the catholic girls
wear to school. It looked nice, but sort of small maybe and when she
walked I could almost see my mom's underwear. I asked my mom why she
was wearing the uniform and she told me they were going to a costume
party, but she looked kind of nervous, or embarrassed maybe saying
that, I'm not sure.

Anyway, the more comfortable my mom got, the more she started going out
with Charli and her husband, and pretty soon it was several times a
week, not just on Saturday and Sundays. Tuesday nights were costume
party nights, I guessed, because that was mostly when my mom wore the
schoolgirl clothes, or sometimes her Girl Scout uniform, which wasn't
really hers. She bought it at the thrift shop and it looked cute, but
kind of funny on her. My mom looked like she was my sister for sure
when she wore that.

One Tuesday mom was wearing a cheerleader outfit, all white and red,
just like the high school girls wear for the football games and stuff.
It looked cool, except she didn't have any cheerleader shorts I
guess, since she was wearing red panties. I told her she better be
careful if she started jumping or everybody would know. That just made
her laugh a little and then she really surprised me. She had a dog
collar and she was putting it on.

"What's that?" I asked, knowing what it was, but not sure why my
mom would wear it.

"What does it look like?" My mom smiled at me in the mirror.

"A dog collar." I said.

"Then that's what it is." My mom shrugged. She'd been acting
sort of weird ever since I started babysitting. "Charli gave it to
me, do you like it?"

"I guess." It was black and thin with a silver buckle and a little
silver tag. "What does the tag say?" I wondered.

"Look." My mom turned around and leaned forward, lifting her chin a
little.

"Lisa." I read it aloud. "That's your name!" I giggled and my
mom just raised her eyebrows. "That's weird."

"I know." My mom nodded, but she didn't explain it anymore.

Charli always looked dark, almost kind of evil, except if you knew her
you'd know she wasn't evil at all. But she looked like it. When my
mom wore her little girl clothes on Tuesdays, Charli was always wearing
something black and not little girlish at all. One time she wore a
uniform, like an army uniform with a blood red swastika thing on the
arm and silver SS lightning bolts on the collars. It was tight and
really showed off her body and I kind of wondered if I'd ever have
boobs like hers, cause they were sort of big and nice. My mom has small
boobs and mine didn't start growing hardly at all until I was older.
Anyway, those clothes made me a little nervous cause I'd been told in
school about those Nazi guys and they hadn't sounded very nice, but
Charli wasn't a Nazi, she told me seriously, she just liked the
style, the emotions too, but I didn't really understand that. The
only emotion I got was scared.

Charles liked to dress normal, like he always did, even on Tuesdays. He
looked nice though, so I didn't mind. I asked him about it once, how
come my mom and Charli would get dressed in costumes and he would just
wear regular clothes. He told me he liked to change at the party
because he dressed like a criminal sort of and didn't want the police
to make a mistake and arrest him. It sounded funny and I laughed.
Charles was so sweet nobody would ever think he was a criminal!

"I wish I was older." I said one Tuesday night, not long after my
mom had gotten her dog collar. Charli was wearing her Nazi uniform and
I had been looking at her boots, which were really black and shiny and
came up to her knees with the pants tucked in.

"Why's that, sweetie?" Charles asked me. He was holding Mason
while we waited for my mom, who was just coming into the living room.

"Cause you guys get to go to a costume party every week, but I never
get to go except on Halloween sometimes."

My mom smiled at me. "Don't worry, when you're older you can go
to all the parties you want."

"Really?" I asked, thinking my birthday was just 9 months away and
I'd be fourteen then, that was older.

"Yeah, like when you're thirty." She laughed as my face fell into
a scowl.

"Oh, I don't know." Charli was looking at me. "Janice is
growing up, maybe she should have a little fun with us sometime."

"Darling..." Charles started to say, but my mom was quicker.

"What?" She looked startled. "I don't um, I don't think
she's quite that old yet."

"Oh, I think she is." Charli was smiling and she walked over to me
and I was a little confused, actually. She held my chin for a second,
tilting my face up so she could look into my brown eyes. "She's
very smart, aren't you Janice? And mature and so pretty...very
pretty..."

"Uh, yeah." I shrugged.

"We better go, we'll be late." Charles said, and he made enough
room between Charli and me so I could take Mason from him.

"Be careful dear, the phone numbers are on the fridge." My mom gave
me a kiss like always and glanced at Charli who was still looking at
me.

"Don't worry, Janice." Charli kissed me too, leaving lipstick on
my cheek. "You'll play with us soon. I promise."

My mom didn't say anything, but I know she must have heard what
Charli said. I was more confused than ever by the time they'd left
and I could settle down with Mason for a little TV before his bath.

Mason was a really good kid and he hardly cried or made a fuss and he
always went right to sleep after his bath. I put him in my bed, since
Charli and Charles had brought him over. Usually I just went to their
house to babysit. I did my homework, which was pretty easy and took a
bath of my own, which I had really started enjoying a lot, and not like
when I was a little kid. I had a little bit of hair starting, not very
much at all, but just a little around my pussy, and I liked that a lot.
It meant I was growing up. My breasts too were growing, sometimes they
hurt a little cause they were trying so hard, but they were still
small, just speed bumps is what the kids at school called them. Still,
they felt good when I rubbed them sometimes, especially my pink
nipples. They'd get hard and long and it made my tummy do little
flip-flops sometimes, especially if I was thinking about Charles.

I liked touching my pussy too, except I was sort of careful down there.
I mean it looked sort of cute, and it felt warm and soft, especially
inside, but I didn't want to hurt myself. I wasn't sure what was
okay and what wasn't, but sometimes I just rubbed the little knot of
flesh at the top of my slit. That didn't seem to bother anything and
it felt really good, like little lightning bolts were hitting it
sometimes, and then it would get hard a little pinkish red bit would
pop out and that felt really nice to touch. I had looked at the biology
stuff on my computer encyclopedia and I was pretty sure that was my
clitoris, but I wished I could have asked someone just to make sure.

After my bath I just put on some panties and my bathrobe. My mom and
the others wouldn't be back until late, real late probably, and I was
always asleep when Charli and Charles got home anyway. So I was pretty
relaxed and I turned on MTV and sort of danced around for awhile,
trying to move like the girls did on my TV set and mostly laughing at
myself. It was fun, I mean for being alone, you know.

"Hey, are you having a party here?" Charles surprised me and caught
me as I was spinning around, one arm going around my waist and his
other hand on my bare tummy where my robe had opened up and I was slow
to realize that he could see my panties and even my boobs, cause it was
wide open.

"Oh, uh hi!" I sort of hung there, off balance leaning backward and
just supported by the man.

"Hi." He smiled and his hand was rubbing my tummy gently and I
blinked, turning real red and struggling to move a little.

"Where's my mom?" I asked and I was trying to close my robe and
wondering why Charles wasn't letting me go.

"She's at my house." Charles said quietly, "With Charli."

"Oh." I licked my lips.

"I'm going to kiss you." Charles told me, like it was the most
normal thing in the world and I stared at him.

"You are?" I asked and that was probably really dumb.

"Uh-huh." He smiled. I'd pulled my robe closed, sort of, at least
covering my nipples which were hard and itching like crazy right then.
But his hand was still on my stomach and he was just squeezing me with
his fingers, just a little, but it felt really good for some reason.

He did kiss me too. Charles bent over and held me tight as his lips
found mine and I didn't know what I was doing. I kept my eyes closed
and my lips shut and even when I felt his tongue tickling me, trying to
get inside my mouth, I didn't let him. I just giggled until he
stopped.

"What?" He was smiling.

"That feels funny." I told him. "Your tongue."

"Well, it's not supposed to." He laughed and his hand was sliding
up, under my robe towards my small boobs. "It's supposed to feel
good. Open your mouth for me this time, Jan."

I bit my lip staring into those dark green eyes and wondering how this
happened. It was so weird it was making me dizzy.

Charles kissed me again and this time I let his tongue move between my
lips and that didn't make me giggle at all. I could feel it, wet and
warm and wriggling across my teeth, inside my mouth and over my tongue.
It was making me hot and my body tingled and I moaned a little,
especially when I felt his hand on my left boob, pressing against my
hard nipple like he was trying to flatten it. It felt like an ache sort
of, almost painful but really, really good and I forgot about trying to
keep my robe closed and just hugged him.

I tried to do everything Charles did. I moved my tongue around, and it
seemed so small when I chased him into his mouth. I licked around his
straight white teeth, and scraped the insides of his cheeks. I even
explored the roof of his mouth. It was crazy and wild and made my heart
pound inside my little body until I thought I was going to explode. My
lungs ached because we kissed for so long I was running out of air, but
I still didn't want to stop.

Somehow I found myself being pulled down. Charles was sitting on the
sofa, although I didn't remember us moving very much at from the spot
where he'd found me. He had my hands in his and was pulling me onto
his lap while he sat there smiling at me. I was so excited and hot all
over that I could barely breathe. I wasn't stupid, I knew what we
were doing, and it had to be wrong. He was my friend, my mom's
friend, and married and so much older than I was. I was just a girl, a
kid, and he was a man. He couldn't like me, not like this, could he?

I wasn't stopping him and probably I couldn't. He was so perfect
and handsome and everything I'd ever dreamed of in a boyfriend. I let
him move me, so that my legs were spread wide over his thighs, kneeling
on the soft cushions with his hands inside my open bathrobe, on my
hips. He was looking up at me and smiling warmly, squeezing me gently
and I was frightened, almost terrified, but not by him. I was only
scared of what we were doing. This was sex, I knew, and even if it was
just kissing it was sex, but he was touching me and looking at me and I
knew we were going to do more than kiss.

"Are you okay?" Charles asked me softly, and I just nodded.
"You're so beautiful, do you know that? As pretty as your mom, or
Charli, or anyone."

His words thrilled me. I thought Charli was the most beautiful woman in
the world. "Really?" I asked him and I closed my eyes briefly as a
little shiver went through me.

"Oh yeah, honey." He said seriously. And then we were kissing again
and Charles pulled me to him so that my body was against his chest. I
could feel the soft texture of his shirt against my aching breasts,
rubbing my nipples raw as I moved, unable to keep from sliding myself a
little up and down, side to side. I was melting inside, way down deep
in my tummy and I could feel it between my thighs, like warm butter in
my sex. It was a strange sensation and one I might have felt before,
once or twice, but never like this. I wanted to feel like that all the
time.

Charles moved his hands along my back while his tongue filled my mouth.
All I could do was moan and sigh and suck on it. I felt like a baby or
something, nursing on the man's wet tongue as he seemed to reach all
the way to the back of my mouth. But it didn't make me choke or
anything, it just tickled in a hot sweet way and I almost wished I
could swallow it, strange as that sounds.

"Ummm...." I was shaking and moving my hips, trying to understand
why. My virgin pussy was itchy now, throbbing almost and I wanted to
rub it, to feel something against it. I'd never felt like that and it
was confusing and made all the worse because my thighs were spread and
I couldn't bump it against anything. I had my arms around Charles'
neck and his strong gentle hands were just at the top of my butt,
playing along the waistband of my panties.

"What is it?" He breathed, pulling his mouth from mine for a
moment.

"I...I feel funny." I felt drunk almost, like the time I'd had a
glass of wine at Thanksgiving the year before. Except I wasn't
giggling, I just had that same warm dizzy feeling.
"Down...there..."

"Down here?" Charles smiled softly and then I felt one of his hands
sliding along my butt, across my panties and down, following the round
contour of my rear end until he was underneath me and then...

"Ohhhh!..." I shivered and lifted my body with a sudden jerk, as if
I were trying to get away. His fingers were on my sex, rubbing it from
behind through the damp material of my underwear. Charles pressed
against me hard, almost lifting me, and his fingers seemed to push
inside, just a little maybe, working my panty between my greasy little
lips.

I saw stars and shut my eyes tightly, hugging him so tightly that I
couldn't breathe as my puffy breasts were pressed hard against his
chest. My butt was moving, my hips and everything. My thighs tried to
close and I was squeezing my legs against his. And that hot buttery
warmth was exploding, my insides trembling like a thousand little
cramps coming and going so fast it was impossible to imagine. Nothing
could feel like that, never. But it did and I was almost crying as I
hugged him.

It felt so good, and carried me so far away that I didn't even
realize Charles had stopped touching me. It felt like he was, sort of,
and I kept cumming and cumming beneath the precious pleasure of my
first ever orgasm. But he wasn't, he was moving his hands, opening
his trousers and freeing his hard penis. I was just starting to think
again, to remember where I was and what we were doing, when I felt it
against my skin.

His penis was long and so big I could scarcely believe it. I knew about
sex and how people did it and where babies came from and all that. But
now Charles had freed his penis and it stood straight up against my
panties as I straddled him. And further than that, the tip was near my
belly button, and I could feel his skin against mine, hot and sticky a
little with the wetness running from the big rounded head. It was dark,
most of it, but the tip was lighter and pinkish.

"Are we going to have sex?" I asked Charles softly and the words
frightened me even as I said them. But that was a silly question, I
knew, because we were already having sex.

"Do you want to?" Charles was holding my hips again, smiling at my
face while I looked down at his penis.

"I'm scared." I told him. I was scared of doing it, I was scared
of getting caught, I was scared that it would hurt because it was so
big. His penis looked way too big for my little hole. And I was scared
that he wouldn't like me. That was the worst thing. What if we did it
and I didn't do it right? He'd hate me then.

"I'll be careful, Jan, I promise." Charles whispered. "It's
okay, I love you."

"Y-You do?" I looked back into his eyes and he nodded.
"Really?"

"Yeah, really." Charles told me. "I want to make love to you, the
way I make love to Charli, okay?"

I thought my heart was going to burst, it was pounding so hard. I
forgot to breathe too and my lungs hurt. I still had those good
feelings, down there in my sex, and way inside, like they'd never
really gone away at all. I swallowed hard, nodding and hoping it was
okay, that it would be good and he wouldn't hate me because I
didn't know how.

"Good girl." Charles sighed and he had me lift myself, just a
little as he reached down to pull my panties to the side, exposing the
plump pink folds of my sex. I was so wet down there, like I'd peed
myself or something, but I knew it wasn't pee at all. The air felt
cool against my pussy and it was just another sensation for my poor
little brain, already much too full with new feelings.

I just looked down, watching as Charles moved his penis, the head
sliding across my slit slowly, back and forth and making me gasp. It
was almost as good as his fingers had been, maybe better except
different, I didn't know. But the feeling of his cockhead rubbing my
pussy made me want it all the more. I had to fight to keep my body
still, like every part of me just wanted to push down and feel it
inside.

Charles worked the head inside finally, just a little, just enough to
split my lips, and then he told me to push. "You do it, Jan, just as
slow as you want, take my cock, baby...that's it...nice..."

I was doing it, like he'd finally given me the permission I'd been
waiting for. I just let myself down slowly, letting gravity do all the
work as the swollen head of Charles' penis spread my labia wider and
wider and then I felt him really entering me and it didn't hurt at
first. It was okay and I let myself go a little more and then it did
hurt, like a small pinch. I stopped, hitching a sharp breath and
glancing at Charles, but he was smiling and nodding, whispering
encouragement.

A moment later I was taking more of him, my body taking his penis just
a fraction of an inch at a time. The pinch became a cramp, and an ache,
and a dull throbbing that got sharp when he'd go a little deeper. My
pussy seemed swollen, spread out around him and my soft pink lips were
tucked in, as if his cock was tucking my pussy inside of itself.

"That's it Jan...nice...ohhh...you feel so good...go deeper,
girl..." Charles was telling me and his fingers were tightening
around my waist, but he wasn't forcing me.

I went lower and lower until I suddenly felt something really sharp,
really painful, like all of a sudden his penis had become a knife and I
stopped, wincing at the pain and I don't think he could have gone any
deeper anyway. He was hitting something, hitting the bottom of my
pussy, I thought, and there just wasn't anymore room. But I'd only
gotten a few inches of him inside me, not very much at all really, and
there was so much of his penis waiting.

"Are you alright, Jan?" Charles asked me.

"It hurt, right there." I said. "That's all, right?" I
wasn't sure what I was asking really, but mostly I just wanted to
know if we could stop. We'd did it, a little bit, that was enough,
right?

"It's okay, baby, that's just your hymen." Charles was smiling
at me. "Come here..." He put a hand on my neck, pulling my mouth to
his while his other hand went to the small of my back.

Charles kissed me gently, and then harder, pushing his tongue into my
mouth and I liked it. Kissing him felt good, it was familiar and soft
and nice and it made me feel safe. I looked in his eyes, for just a
second after we stopped kissing, and then Charles pulled my face
against hi neck and I felt his hand pressing hard against my lower
back. He lifted his hips, thrusting upward hard, driving several inches
deeper into my virgin sex.

Pain exploded in my pussy, and more, in my tummy, like I'd just been
punched or something. I screamed against him, his body muffling the
sound and I gripped the man tightly, my body tensing against the
unexpected flash of agony. He'd ripped through my hymen and stretched
my sex mercilessly, tearing through my soft flesh so that more than
half of his huge penis was buried inside my body.

Tears flooded my eyes and I felt sick almost, and weak like a small
child. I clutched Charles and sobbed, my body shaking and every
movement bringing a fresh stab of pain. I tried not to move, I didn't
want to try and get off of him, nor could I stand thinking about his
penis going deeper. I just wanted to stay like that, afraid of doing
anything that might make it hurt again.

"I'm sorry...I'm sorry, baby...Shhh...it's all over now..."
Charles was kissing me and stroking my body gently, not moving at all.
But I could feel his cock inside me, like it was throbbing and swelling
even more. My pussy burned around him and I had no control of my aching
muscles, they spasmed all on there own and that was another sort of
pain. My body was contracting around him, squeezing his penis, and
there was nothing I could do about it.

I think we just sat like that for 5 minutes. Maybe longer, before
Charles began moving, just a little. I'd stopped crying and the sharp
pain was gone, but it still hurt a lot. He was moving just a little,
back and forth and at first I'd really dreaded it, shaking my head
and begging him not to move. But it wasn't that bad, not like I'd
feared and so I stopped trying to make him stop. I was tired and
feverish, my eyes hurt from crying, my lungs hurt from trying to
breath, and my pussy and tummy and thighs, they all hurt.

"I'm going to cum....ohmmmm..." Charles sighed and kissed my
cheek and then my mouth, coaxing me to kiss him back and I did. I
wasn't mad at him, I loved him, but I didn't really understand why
it had to hurt, why he had to do it like that.

But then I could feel his penis, it was moving inside me and then
jerking and then there was a funny sensation, really vague like I could
barely feel it at all, but I did. Charle's was cumming inside me, his
penis shooting his sperm inside my painfully stretched pussy. He kissed
me hard and I kissed him back then, suddenly feeling better because I
knew he still liked me. He was putting his sperm in me, so he loved me.
I almost forgot that it had hurt so much and just tried to think about
what he was doing. I even moved my hips, just a little, but that sent a
shot of pain straight through me and I stopped, wondering when that
pain would ever go away.

Charles kissed me a lot and I kissed him and when we stopped I could
see his eyes looking over my shoulder. I was confused for a second,
wondering what he was looking at, and then I looked, turning my head
slowly, and I could see my mom there, with Charli, looking at us.

"Ohhh..." I practically jumped off Charles, and my heart really did
stop for a second. I had to get up, to get away, I was going to be in
so much trouble. Panic filled me, real panic that made me forget about
something as unimportant as pain suddenly was. I was moving and Charles
was trying to hold me.

"M-mom....I..." I almost started crying again. I was so sure she
was going to be mad. And Charli, she must be hating me, I thought. I
was doing it with her husband. She probably wanted to slap me or
something.

"Jan, honey...Are you okay?" She came over quickly, putting a hand
on my shoulder. Charli was right there with her too, smiling at me.

I couldn't think of anything to say. I'd slipped off of Charles'
penis without really realizing it, but it was hurting again. But it was
a strange kind of hurt too, like I was still stretched around him, but
I was empty too.

"You should get her in the bathtub maybe." Charles said gently.
"I think she's a little tender."

"You think?" Charli laughed lightly, shaking her head. "You
should have waited til we got here."

"I tried." Charles shrugged. "But you know..."

"Yeah...I know you..." Charli wasn't mad at all, I realized.

And neither was my mom. She was helping me off the couch slowly,
telling me everything was going to be alright. We'd just take a nice
warm bath and everything was fine. I looked down and my pussy was red,
streaked with blood and some pinkish sperm, and my little slit was sort
of open a little, like it couldn't remember how to close.

"You did real good, baby." Mom was kissing me. "I'm proud of
you."

"You'll be fine, sweetie." Charli was touching me, stroking my
hair. "Next time it won't hurt like that, I promise."

"Next time?" I whispered, blinking at the three adults around me.
They were all smiling and happy and relaxed and I tried to understand,
but it was hard enough just walking to the bathroom with my mom.

End
rache696@yahoo.com

-- 
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