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Message-ID: <32680asstr$1001671805@assm.asstr-mirror.org>
Reply-To: "Jimbo" <Jimbo@spam.com>
From: "Jimbo" <jimbo@spam.com>
NNTP-Posting-Date: Thu, 27 Sep 2001 15:48:47 EDT
Subject: {ASSM} A Night of Firsts with Ms. Shelby (M/F, sleepy, drunk)
Date: Fri, 28 Sep 2001 06:10:05 -0400
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Newsgroups: alt.sex.stories.moderated,alt.sex.stories
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A night of "firsts"

Back in the seventies, when I was about 15 years old, I used to spend the
night at my best friend's house just about every weekend.  He had two
sisters.  One was my age and the other was about 10.  The sisters were
decent enough to look at at the time but they were not my main fantasy at
the time.  No, his mother was the apple of my eye.

Her name was Shelby.  She was about 30 years old and divorced.  She had
recently begun to go out more and more often and would usually come home
drunk.  Looking back, I think she had a drinking problem as she almost
always drank.  But she only got drunk at night.

She was a really good-looking mom.  The kind of mom that all us neighborhood
boys had dreams about.  She had a curvy, voluptuous body, brown hair, olive
skin, full lips and a really, firm, round bubble-ass despite giving birth to
three kids.  Her tits were about two handfuls.  About the same size as the
perfect women you see in a Playboy centerfold.  I shit you not!

One day, I overheard Shelby telling my own mom that she had a date that
evening and had planned to go to a bar,  I was well aware of Shelby's
penchant for drinking and had previously heard her deep, relaxed, soft
snoring many a night as I lay in bed at my friends house.  It had recently
occurred to me that she probably slept pretty hard and I thought it would
take a lot to wake her.  I occurred to me that I might be able to steal a
glance at a REAL naked woman if I were careful!

So, upon hearing Shelby tell my mom she had plans to drink that evening, I
invited myself to spend the night over ay my friend's house.

We spent the evening playing Monopoly and watching television until about
midnight.  My friend finally had enough and went to bed.  I made myself at
home on the sofa, cut off the TV and the lights and waited for Shelby to get
home.

It was around 2:00 in the morning when she finally came home.  I immediately
knew she had been drinking from the soft hiccupping I heard as soon as she
walked through the front door.  I pretended to be asleep as she walked past
me on the couch.  She stopped right in front of me and appeared to stare at
me for quite some time.  Little did she know that as she was looking at me,
I was also checking her out through semi-closed eyelids.  She was wearing a
black seventies-style thin nylon dress cut just about midway up the thigh.

My eyes were right at the level of her knees as she stood there looking at
me and still softly hiccupping.  I'm not sure what she was thinking but I
was hoping she might kneel down and give me a good night kiss.  But she just
stood there swaying back and forth slightly trying not to fall over.

She finally turned and staggered away from me down the hall to her bedroom
and was unzipping her dress from the back prior to reaching her room.
Before she entered her room, I got a glimpse of a black bra and the top of
her black panties.  It was almost enough to make me come right there on her
couch!

It wasn't long before I saw her bedroom light go off and it was only minutes
before heard her familiar soft snore signaling that she was ready for me!

So I quietly walked down the hall to her bedroom and got down on my knees
before I entered her room.  The room was dimly illuminated with the light
from the bathroom she always left on.  She was laying flat on her back with
one leg outstretched and the other leg bent so that one foot was tucked
beneath her other knee.   It was a warm, summer night so she had only pulled
the covers up to just below her knees.  She had evidently removed her black
bra and was wearing a gray, cut-off tee shirt and her black nylon panties.

I ducked low and very slowly crawled to the side of her bed and peeked over
the edge of the mattress at her for an eternity while working up the courage
to touch her.  From my vantage point, I could just glimpse the bottom of
both white breasts, which contrasted nicely with the tanned, olive skin of
he smooth, flat stomach.

As she lay there snoring softly, I risked tugging at her cut-off tee shirt
to see if she would notice.  She didn't budge and her breathing pattern
remained slow and soft.  So I risked lightly pulling the tee up her chest a
little ways to get a glimpse of her nipple under the tee.  Still, she didn't
budge.  So I became bolder and very slowly continued to pull her shirt up
until both breasts were fully exposed.

Now keep in mind that this was my first view of real breasts on a real
woman.  Up until this point, the most I had seen were the tits in the
Playboy magazines my dad kept beside his bed.  Let me tell you, the real
things were not disappointing!  They were every bit as full and beautifully
developed as any centerfold I had ever seen.  Her dark brown areolas were as
large as a half dollar and her nipples were flaccid.

I became even bolder as her deep breathing remained undisturbed and risked
touching one breast with just the tip of my index finger.  She remained
still.  So I risked lightly placing my palm on top of her breast and hoping
the whole time that the pounding of my heart really wasn't as loud to her
ears as it was to mine.

She remained soundly asleep as I simply let my hand rest, unmoving, on her
breast as I pondered what I wanted to do to her next.

I decided I wanted suck her nipple but before I did, I wanted to make sure
she was as deeply asleep as I hoped so I gave her breast a light squeeze.
No movement.  No change on breathing patterns.  So I lifted my hand and took
her flaccid nipple between my thumb and index finger and gave it a light
squeeze.  No movement!

Emboldened, I got the courage to stand on my knees, lean over her beautiful
sleeping form and kiss her nipple ever so lightly.  I began to suck slightly
on one nipple and grabbed her other tit with my left hand and squeezed
lightly.  I remember the feeling of her nipple hardening under the touch of
my tongue and I almost came all over myself at that moment.

Then I leaned back and moved my hands very slowly from her breasts, over the
smooth, tan skin of her belly and on top of her black panties.  My hands
dwelt on the cushiony softness of her bush from outside her panties while I
worked up the courage to slip my fingers underneath.

When I couldn't stand it any more, I slowly slipped one finger, then two
then all five fingers underneath her panties.  I then slid my hand down to
her bush.  As I reached her soft bush, I slid my other hand up to one of her
breasts, leaned back over her and sucked her nipple some more.

Becoming more comfortable with the soundness of her sleep, I slid my hand
deeper into her panties and lightly cupped her warm, moist vulva in my palm.
I tentatively explored her unseen and mysterious slit with my middle finger
all the while sucking vigorously on her nipple.

I wasn't really familiar with fine details of the he female genitalia until
that night.  I knew there was a hole there in her pussy somewhere but I wasn
't sure where.  I decided to find out.  I reached down and slowly tugged on
either side of her panties and slid them down her hips just until her entire
dark, soft pussy was exposed.

I still couldn't see the hole, though.  Her pussy lips were still nicely
stuck together at that point.  So I explored further with my fingers and
lightly stroked her warm pussy lips.  I stroked with more boldness as she
remained in deep sleep until the pink lips parted under the pressure.  For
the very first time, my finger entered the warm slipperiness just between
her lips and explored the moistness there.  As I explored, my middle finger,
quite accidentally, entered her vagina.  I had discovered the hole!  I
entered it tentatively at first then with more boldness as my beauty
continued to snore softly.  I slid first one, then two, then three fingers
into her vagina.  I then turned my hand so that my thumb was pointing down
towards her ass.  As my fingers explored the deep recesses of her vagina, I
let my thumb ease down between the crease of her ass and touched her ass
hole.  I spent quite some time there gently pumping her pussy while my thumb
rested on her ass hole.

The thought of actually fucking her didn't occur to me at the time.  I'm
sure I could have since she was obviously wasted and had probably passed out
more than fell asleep.  But I did consider other things.

As I sucked on her tit some more with my finger well into her twat, I felt
something brush against my dick through my underwear.  I looked down and
noticed that her left hand, with upturned palm, had been hanging over the
edge of the bed.  My groin area had accidentally brushed against her hand as
I leaned over to suck her tit some more,

As I sucked her tit, I reached down and pulled my underwear down to my
knees.  I don't think I had ever seen my dick look so large and hard but
there it was only inches from sleeping beauty's hand.  I gently stretched
her fingers out so her palm could accommodate my hard dick.  I then helped
close her fingers around my dick with one hand and proceeded to suck her tit
more.

As I sucked away at her tit, I "helped" Ms. Shelby give me my first hand job
by closing my fingers around her hand, which was lightly grabbing my dick.
I moved her hand and up and down my dick while I squeezed my hand tighter
and tighter around her hand.

I probably only helped her stroke my dick ten times or so before I nearly
came but I didn't want to spoil the fun yet!  So I quickly released her hand
from my dick and boldly stood up beside her bed and considered what else I
could do.

Just to make sure she was still sound asleep, I softly called her name, "Ms.
Shelby? . . .Ms. Shelby?"  No answer.  So I leaned closer to her until my
dick was only and inch from her face.  I gently stroked her breasts while I
looked down upon her slightly open mouth and full lips then it dawned on me
what I had to do.

I carefully placed one knee on the edge of the bed in order to get in
position to perform the ultimate (even after all these years) fantasy of
slipping my adolescent dick inside this sleeping mom's mouth.  Before I did
so, I touched her lips with the same finger than had been inside her pussy a
moment before in order to make sure her mouth wasn't more sensitive than the
rest of her body.  She didn't even twitch as I first touched her lips with
my index finger then slid it deeper inside to touch her tongue.    Her soft
snoring continued.

So, with my knee up on her bed and my amazingly huge dick (with a curious
large drop of what I would later find out was "pre-cum" oozing from the tip)
poised over her face, I edged closer.  Closer still until I barely touched
the corner of her mouth with the head of my dick.  I let it stay there for a
moment then, with the assistance of my free hand, slowly rubbed the head of
my dick over her lips spreading the pre-cum until her lips were glossy with
the stuff.

I was hard to balance on one nervously shaking leg as I gently slid the head
of my dick into her mouth and touched her tongue with it.  Very slowly I
pumped just the head of my dick in and out of her mouth until a few more
drops of pre-cum oozed from my dick and rested on her tongue.  I quickly
pulled my dick from her mouth before I came and got back on my knees.

I knelt there for a moment just staring at the face of the beautiful mom
that had occupied so many wet dreams.  There she lay powerless to stop
anything I was doing to her.  So many times I dreamed of kissing her and
fucking her and here I was doing everything to her but fucking!  I wanted to
scream with joy!

I stared at her now-moist lips, leaned my face over her and placed my lips
against hers and kissed her.  First the bottom lip then the top lip.  Then,
I slid my tongue into her mouth and tasted my own pre-cum.

I then leaned back and spit into the palm of her hand for lubrication.  I
once again helped her hand grab my dick and spread the saliva and more
pre-cum all over her palm.  While I helped her stroke my dick with one hand,
I eased my face down to her cunt, placed my nose between her legs and took a
sniff.  She had evidently sprayed a small amount of perfume down there so
the scent of that plus the musky scent of her moist pussy was nearly enough
to make me come.  But not yet!

As I helped her stroke my dick, I let my tongue enter the velvety smoothness
of her pussy and licked sweet-salty juice from her.  As she stroked my dick
faster and faster, I began sucking her pussy with more and more boldness,
yet still with a fair amount of gentleness until I began spurting come all
over her palm and arm.

My orgasm went on for ant eternity as I softly grunted with her pussy lips
filling my mouth.

When I was spent, I didn't know what to do with all the cum on her arm and
hand so I gathered as much of it as I could with my hands and spread it on
her breasts as if it were suntan oil.  I then pulled her tee shirt back over
her tits and pulled her panties back over her pussy.

Before I left her room, I have her one last, long kiss and said, quietly,
"Until next time, Ms. Shelby."

-- 
Pursuant to the Berne Convention, this work is copyright with all rights
reserved by its author unless explicitly indicated.
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