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Stupid Annie

Age when it happend: 17
Where it happened: Tillamook, Oregon
Langauge: English
Sex: Female
Rating: 9
Category: Straight

When I arrived home from school, my sister Sally and her
old, divorced boyfriend, John, were drinking tequila and
they asked me to join them. Now I don’t really drink
and I’ve never been drunk before but I was feeling
particularly low at the time so I agreed to join. Sally
and I were renting a single bedroom condominium with two
beds. The two of them are on Sally’s bed and I sat on
the lamp table between our beds. Of course, not being
used to drinking and unfamiliar with how much alcohol
can make me drunk, I just naively drank away almost
everything that John put in my glass. As I got more and
more relaxed and uninhibited, I started confiding to my
sister about Janice.

I don’t know exactly how sex became the focus of our
conversation, but I guess it was inevitable since I was
talking about my best friend getting fucked by a dud.
And then, I must have mentioned about me still being a
total virgin and having a lot of reservations about
almost every guy who tries to get close to me.

“Why, does that mean you’ve never been kissed before?”
John asked.

“No. Not even by my first and only boyfriend. I don’t
know, it just always felt like guys were always trying
to get under my panties as if that’s all that matters
to them. That’s why I’ve never even got close to being
intimate with a guy.”

After this, the topic quickly got into my non-existent
sex life. But as I confided to my sister, I didn’t
realize that I was also unwittingly revealing myself up
to John who I didn’t know was already trying to gauge
how he can exploit my vulnerability at that time with
the help of the alcohol.

Like most boys, I know John lusts for me too. He had
flirted with me many times and he must be ogling me all
the time since I frequently catch him doing so. And
since John became Sally’s boyfriend, he had been a
frequent visitor in our place, even sleeping with my
sister in our room occasionally. Although I know my
sister didn’t want him to, she is much too involved
with John to resist him when he insists.

Now John is an intelligent person and a very good
conversationalist, but that doesn’t mean I like him.
Actually, I despise him for using and playing my sister
while flirting with me time and again, and I despise
him more for the fact that he is already old and
divorced and his youngest daughter is my classmate! He
actually met my sister through me and my classmate.
Since then, I had no choice but to bear with him ’cause
my sister won’t listen to me and leave him. It’s a
relief that talking to him is at least bearable. I just
hope that some of my friends’ fear that John only
courted my sister to get near me isn’t true.

Anyway, Sally was already quite drunk when I joined
them so it didn’t take long before she was wasted. I
wasn’t doing much better either as I was feeling really
tipsy already. With Sally half passed out, I didn’t
notice that it was now John who’s asking personal
questions. And with much of my inhibitions washed away
by alcohol, I just kept on answering him.

“Aren’t you curious about kissing and petting?”

“Maybe you’re afraid of getting carried away.”

“Are you afraid of sex?”

“Don’t you wanna try it?”

John kept asking and I kept on answering him! Although
I was feeling really tipsy already, John’s questioning
kept my mind awake. And I didn’t notice that his
questions were leading me to think about sex and
imagine it. He was also challenging and making me to
re-think my inhibitions about it.

“What if you can experience sex or even just petting or
kissing without anybody knowing about it? Would you try

I do want to experience it out of curiosity, I thought.
It’s just that my values and probably my looks make it
so embarrassing for me to end up giving myself to a guy
who might brag or talk about his sexual of me like
Chad. I am pretty and innocent and I like that about
myself so it is imperative that I find a guy that will
love and respect me enough, that he wouldn’t dare turn
into a kiss-and-tell.

But now, John is playing with my curiosity about sex
while my judgment is clouded by alcohol by floating the
idea of anonymous sex – the chance to know what it
feels kissing, petting or even having sex without
consequences and without the risk of losing other
people’s respect and high regard for your purity.

“Ummm, maybe. I don’t really know,” I replied coyly.

Sensing my provoked curiosity, John started telling me
about how good it feels to be intimate with someone.
Without being too obvious, he quickly described quite
vividly how kissing, then petting, then having sex

“I’m sorry. I’m really not supposed to be telling you
things like these,” he finished appearing apologetic.

At this time, Sally was already completely passed out
and John started to make his move. He told me how
beautiful and sexy I am and how unfortunate it is that
I don’t have a boyfriend. He continued complimenting me
and telling me how lucky my future bf will be and how
much of a jackpot it will be to be my first.

These comments made me blush but maybe, because of
alcohol, I didn’t find them offensive. This made John

“Do you want to experience a kiss right now? And maybe
a little hugging?”

I should have expected him to try to ask something like
that, but being drunk as I was, I didn’t. So I was
really caught off guard with the question. But John
didn’t give me time to answer.

“I’m sorry. It’s just that I feel like you’re missing
something really good and I want you to experience it.
I promise it will feel really good.”

“What?” I was still a little shocked and drunk to be
angry . “I don’t…I still don’t think so.”

John was already sitting at the edge of their bed and
as I stammered tipsily, he made his way towards me and
sat beside me. His left hand quickly went over my
shoulders and he slowly drew us closer. I couldn’t
react in disbelief.

“It’s ok,” he said as he tried to kiss me.
Instinctively, I turned my head away.

“No, …” I said but his right hand quickly held my
cheek and pulled my face towards him.

I know I was curious but I also know that I don’t want
what’s about to happen. I thought of saying no again
but he cut me off.

“It’s ok. No one will know,” he assured me.

I know I didn’t want to let him kiss me because it was
embarrassing to have an old divorced man who’s been
fucking my sister as my first kiss. But here is my
chance to experience something sexual without any
consequence…no one will know. Is this ok with me? I
haven’t thought about that yet but if I wasn’t so
drunk, I had time to think and I hadn’t panicked, I
would have realized that I didn’t want to. But I was so
drunk and inexperienced and even before I could start
to think, he already had his lips over mine.

At that point, my head just went blank and the only
thing I know was how that first kiss felt, which was
good. I tried to push him on instinct while trying to
break the kiss but he didn’t budge; I was too weak and

When his tongue started to probe inside my mouth, I
reluctantly let him. I don’t know if it was instinct or
helplessness or just me liking the kiss, but I
responded. After a short while, I realized that my
heart was beating really wildly. I was so nervous that
when he briefly broke our kiss to ask if I was ok, I
couldn’t find my voice.

John quickly took advantage of this. He kissed me more
passionately while embracing me tightly. My breast was
mashed tightly between our bodies while his hand roamed
my back and teasingly squeezing my butt. His strength
made me feel weaker and made me realize that resisting
him might be futile at the time so I just went with the
flow. I thought we were already kissing so I’ll just
let it be. I thought we’ll make out for a while then
stop. No one will know anyway.

But after just a minute or two, his lips started to
travel to my and my ears. I felt tingles all over my
body and I couldn’t help but let out a soft “Oh…” as
I tried to move away again. When he sensed that I was
pushing him, he reassured me, “it’s ok. Just a little
more.” Part of me wanted to protest but I felt like it
would be useless since I don’t have the strength
anymore and it never occurred to me that it could
actually progress to having sex. It was so out of the
question that I just assumed that this would end at
some point.

Sensing my slight surrender, his hands started to roam
freely, first to my stomach and then to my breast. I
tried to ward his hands off but they kept on coming
back. I don’t know when I decided to stop resisting but
after some time, when his hands went to my breasts and
started caressing it – squeezing it gently while
pinching my nipple through my blouse – I just gritted
my teeth trying not to moan as much as possible, but I
didn’t protest anymore.

Two of John’s hands were quickly all over my breasts
and I was now pulling his head firmly as he kissed my
neck. When his lips landed on mine again, I responded
passionately. Having gone this far, I know I wanted to
make out for a while before stopping…and we did.
While doing so, he was able to expertly unzip the back
of my blouse and slightly pulled down towards my front
to expose my shoulder and the top of my bra. I barely
protested when he softly planted kisses down my
shoulders and just on top of my bra.

The sensation made my heart beat faster especially when
I felt him subtly slid my bra down my shoulder. When I
felt him reached to my back to unclip my bra, my heart
skipped and I froze.

“John…” I called as I felt the clip separated. When
his hands slid to my front to remove my bra, I
instinctively drew my hands to hold them in place. But
John didn’t seem to mind this. He kissed me
passionately again while his hands caress my back and
my stomach. Then while trailing kisses down my neck to
my ears, he softly tried to take my bra off my grip.
But I didn’t budge.

“C’mon, it’s ok.” He whispered in my ear. “No one will

When I still didn’t move, he moved to face me but I
couldn’t look at him in shame. I felt so guilty for
letting him go this far.

He then held my two hands and as he gently try to pull
it open from my breasts, he kept on reassuring me,
“it’s ok, let’s just do this a little more. No one will
know. Then we’ll pretend like nothing happened. No one
will know.”

I wanted to protest but somehow I couldn’t find my will
in my confusion. Still undecided on how to react, I had
let him put my hands down to my sides, I felt so
ashamed when my bra slowly slid down and off my
breasts. I’ve always been proud of them and now, I felt
so ashamed and disheartened that I had let no less than
John see it.

“Wow, those’re the most wonderful breasts I’ve ever
seen…” he said grinning as he removed my bra from my

I wanted to cover them but John’s hands held mine in
place. I could feel my face blushing like never before.

Unable to do anything, I just said, “Don’t tell anyone
know about this ok?” I felt so stupid.

“Ok,” he replied, quickly pulling me to him again. This
time, I didn’t protest and just went with the flow.
Soon he was caressing my bare breasts, and then he was
kissing my neck again and then I felt him kissing me
lower until he was near nipples. My heart was beating
so fast now as I anticipate his moist lips over my
nipples. Although there’s still something at the back
of my mind that is still telling me, “Stop! This is
John, you can’t let him do this!” curiosity is
overwhelming me, “Oh my God, just a moment… just this
once… no one will know…”

But he did not immediately devour them. Instead, he
teased me by sucking and licking the skin of my breasts
around my nipples. . “Oh…”

As he kept on teasing me, I started to notice the
burning sensation between my legs. The sensation and
anticipation was arousing me. But there was nothing I
could do but moan and subtly move my nipples to his

Then finally, his lips kissed my nipples. “Oohhh…” I
moaned loudly. “Ohhh shittt!!”

I kept on moaning as his kissing progressed gently to
sucking. When his tongue joined the action, I was
completely lost. I was pulling and pushing him at the
same time while moaning uncontrollably.

Knowing that this was my first time, John knew that the
sensation of his nipple sucking will also suck off the
resistance left in me so he quickly took advantage. He
undid the zipper and clip on the side of my skirt and
gently pulled me off the table a little so my skirt
would fall down from my hips.

He was right, I barely felt my skirt being undone until
it fell off my waist; but even then, I found it hard to
move my hands, which at the time were tightly gripping
his hair. I was starting to make a feeble protest when
he laid my butt on the table again and moved his head
up to kiss me.

Next thing I know, he had already opened my legs and
pulled me until I could feel his hardness rub my vagina
through my now very wet panties. With my vagina burning
with arousal, having something touch it was heaven. It
felt so frighteningly good.

“Oh John…no…” I said softly as I froze, afraid of
the sensation I’d feel if he rubs my opening.

As he started to grind his hips, I couldn’t help but
open my legs farther apart and push into him as he
firmly dry humped me.

“Oh..ooh… John… shit… no!” I kept on saying as I
felt the hotness between my legs finally being
satisfied. At this point, I don’t mind anymore how long
John wanted to dry hump me; I felt like I was going to
pee and explode as my arousal quickly built up. But
John had other things in mind. After a few minutes,
when I was obviously nearing my very first orgasm based
on my rapid panting, loud moaning and frantic rubbing,
he suddenly slowed our dry humping almost to a stop and
let me hang for a few seconds. And then, after making
sure I badly wanted to resume our dry humping, he
pulled me off the table and across the room.

Startled, I just allowed him to lead me to the bed.
“Shit Anne, I’m so horny now. Would you let me fuck
you?” he asked as he kissed me again on my neck and
down to my breast.

“No… John… ohhh…. I can’t…” I said meekly. I
wanted him so bad to rub my clit again but I don’t want
him to do anything more.

“Please Anne… it’s ok,” he said as he sucked my
nipples and then his hand went between my legs and
lightly touched my panty. “Oooohhh…” I answered
anxiously feeling my resistance start to crumble.

“Please Anne… I won’t tell anyone I promise.”
He said knowingly as he rubbed my vagina
sparingly, careful not to rub me into orgasm.

“Oohh…ohhh… nooo… John… just rub meeee…” I
moaned desperately as I try to move my vagina towards
his elusive fingers. “Oh John… pleeaaseee…” I
pleaded helplessly as I felt him slowly get to his
knees while lowering my panties. I made a feeble
attempt to stop him but with him sucking my nipples
while rubbing my clit, I was powerless. I desperately
wanted him to rub me to orgasm, but he was seducing me
to let him fuck me instead.

After removing it, John kissed and breathed gently to
my vagina before rubbing my clit with his tongue for a
second. I couldn’t do anything but moan. “Aaahhh!”

When John got up, I was again left helplessly hanging
for more of his tongue. John then gently moved me to
the bed. “C’mon Anne. Get on the bed now… it’s time
to see how good your virgin pussy feels.”

“John please…I can’t go all the way… I’m still a
virgin…” I tried to plead but I was already allowing
him to push me gently to the bed. At this point, I was
panicking already; I felt so vulnerable and confused
and I was still in denial that he would stop on his

When my legs touched the bed, he continued pushing me
backward while kissing me all over and rubbing my very
hot, wet pussy. This made me off balanced so I held on
to his neck to keep me from falling to the bed.

“Lay on the bed Anne…” he said as he gently lowered
me until my back touched the bed. And then he was
kissing and sucking my nipples again while rubbing my
vagina with his bulging pants. At this point, I
couldn’t do anything anymore but close my eyes and moan
and grind my wet pussy with him. My arousal coupled
with my slight drunkenness was simply too much for me
to make any protest even as his mouth started to make
its way down to my stomach and my pussy.

And then he was breathing on my pussy again. He teased
my pussy lips and walls first for a few moments before
finally devouring my super sensitive clit.

“Aaaaahhhh….aaaah…. ahhhh….” I screamed as I
bucked my back and squirm like a worm in a salt. I was
in so much ecstasy I didn’t know how to react. I
squeezed his head with my legs, then opened them
again…and then squeeze again…

“Johnnn….noooo….” I screamed as I was pushed on the
brink of orgasm. I was ready to explode when again,
John stopped his sucking to continue to torment me and
make me surrender to him.

I was in turmoil as he planted small kisses on the
insides of my legs before he finally stood up.

“Shit Anne, you’re so beautiful.” he said grinning
while slowly removing his pants and briefs. “I’ve
waited so long for this moment.”

I didn’t move as he remove his clothing as I was still
in daze. It was only when he removed his briefs to
reveal his very erect manhood that I finally woke up
from my stupor. Quickly, I covered breasts with my
heads and closed my legs.

“John…” I started to protest but he cut me off.

“Move up!” he ordered as he moved to hold my legs and
shoulders as if to carry me. “You’re mine now, Anne.
I’ve always wondered how good your tight, wet pussy
feels.” He whispered as he shoved me to the center of
the bed in one push.

And then he was moving on top of me.

“John, what are you doing? Please stop. We can’t…” I
cried helplessly still hoping that he’d listen to me.

“I’ve wanted to fuck you for
so long, Anne.” He said as he hold my knees to slowly
separate them. Instinctively, my legs gave a token
resistance, but that was all. With him towering over me
and with the alcohol and the burning sensation between
my legs, I felt so helpless under him. My cheeks burned
in embarrassment as he opened my legs wider and wider
to gradually reveal my dripping virgin cunt.

“John, please, Sally might wake up….” I begged with
my legs wide open. “John, please…I’m still a
virgin…” I begged again as if it was all up to him
whether I’ll be devirginized or not. As if I have no
say on what was about to happen as he moved on top of
me by making a trail with his tongue from my pussy, to
my stomach, to my breasts, to my neck…and then we
were finally face to face while our bodies are tightly
touch each other.

“Sssshhhh, it’s ok…” he soothed me as he started to
rub my slit with his penis before kissing me. His penis
rubbing my slit felt good and that heightened the
feelings of his passionate kiss.

Reluctantly I kissed back nervously. I was slowly

As if he could read my mind, he said, “I knew you’d
give yourself to me…you’re mine now Anne.” When he
started rubbing the tip of his cock in my opening, it
was only then that the reality that I was really going
to be fucked by my sister’s old lover started to sink

“John, I’m still a virgin…” I said desperately but
without moving vagina away from his probing cock. At
this time, I was too aroused to back out.

“Oooohhhhh….oooohhhh!!” I moaned helplessly while
gripping and pulling the sheets on my bed. I was
desperate. He was slightly moving his cock in and out
of my opening now.

“John, nooo…” I pleaded but my hips was rocking
already to meet his thrusts.

John could’ve taken my virginity then but he wanted me
to surrender it to her.

“Do you want me Anne? Do you me to take
your virginity like your sister?”

“Noo…” I said embarrassedly still rocking my hips to
chase his cock as I was desperate to be fucked to

“Ok. I don’t want to force you Anne so just tell me
when you want me inside you already.”

With that, he moved down on me again. When his tongue
probed my slit again to torment me, I finally succumbed
to his seduction.

“Ohhh…please!” I said desperately.

Finally hearing my surrender, John moved up to face me
again. I couldn’t look him in the eye in embarrassment.

“Say it again.” He commanded while gently rubbing my
desperate clit again. I couldn’t bring myself to ask
him again so he stopped rubbing me and waited. After a
few moments of hesitation, “Please.” I said softly as
I started to sob.

“What? Ask me.”

“John, take me…please.”

“Ok, so you’ll give yourself to me willingly like I’m
your lover, ok? We’ll be like we’re lovers ok.”

I nodded submissively as my tears started to swell in
my eyes.

With that, John started to kiss me passionately. Having
said yes already, I felt compelled to respond to him
this time so I kissed back reluctantly at first and
then, finally, I totally surrendered to him, kissing
back passionately.

And then he was starting to insert his cock in me.

“Oh, Anne…you’re so tight… so wet… aahhh… you
feel so good!” He said as he continued to thrust deeper
and deeper. And then he was completely in. I almost
didn’t feel any pain. I guess it was because I was
already flooded with my juices.

“Shit Anne, you’re so tight… I can’t believe I’d be
the first.” He said while looking at me grinning. I
felt like crying and I looked away in shame.

“Please don’t tell anyone John…” I just said.

“It’ll be our little secret. Sure.” He
said soothingly as he started to thrust up and down
slowly. The sensation was just incredible – I felt so
full and the feeling of his penis rubbing my clit with
his long thrusts felt like he was burning my vagina.

Soon, I was fucking him back passionately while moaning
“Ooohhhh…ahh…ahh…ooohhhh….shit….ahhhh…” I
couldn’t believe I was moaning like this but I couldn’t
help even as I realize…shit…I’m giving myself to

“Anne, you feel so good. Aahhh…” John kept saying as
he completely enjoy my body.

As he commanded, I was fucking him back vigorously like
a willing lover, all the time moaning loudly. I
remembered a guy friend told me it is most enjoyable
when the girl you are fucking is horny as hell since
she is so hot and wet and her muscles squeeze the cock.
Add to that the fact that I am a very tight virgin and
I’m letting him fuck me without a condom and I thought,
“I’m letting him totally enjoy my body.”

And then I thought, “I’m letting him fuck me without a

But at that moment, I was finally going to get my first
and most anticipated orgasm “Aaaaahhhhh… ooohhh…
noooo… ooohhh… Johhnnnn… oooohhhhh!!!!”

I almost passed out as I bucked my hips repeatedly in
ecstasy. The sensation was incredibly overwhelming….I
felt tingles all over my body as a gush of fluid
explode from my vagina.

John was close to orgasm himself. He kept pounding me
hard rapidly and I kept on moaning as his pounding
penis kept me on a high.

“Oh, oh, ooohhhh… ahhh, ahhh, ahhh… Oh shit! Oh
fuck! Oh fuck, oh fuck! Anneee! You’re so gooodd!!”
John said loudly as he went on the brink of orgasm.
“Annie I’m going to cum inside you ok… shit I might get
you pregnant, ok?”

I could feel his cock start to throb now.

The question startled me but even when I understood
what he was saying I didn’t stop fucking him back.

“Anne… Anne… do you want to me to cum in you? Tell
me…you might get pregnant if I do.”

What can I say? I was so close to my second orgasm

“John, oh… no, don’t come in me… just… ohhhh…
just a moment more…ohhh!!!”

In less than a second, John plunged himself deep into me
and held me tight and then he grunted and sprayed
his hot semen inside me. “Ohhh fuckkk Annneee!!!”

Feeling his hot fluid did it for me also as I cummed
for a second time. “Oooohhhh… John, nooooo!!!” I
screamed again as I bucked wildly again.

A minute later and our hips were still swaying, his
penis moving in and out gently while my pussy milked
every drop of his seed. Finally, I could feel his penis
gradually soften as I felt the sensations inside me
subside and I slowly regain my senses. I realized my
legs were firmly grasping his body and my hands were
holding on for dear life at each of his arms.

As we untangled ourselves from each other, I could not
look at his grinning face. The shame was just
unbearable. I couldn’t believe I let myself be tricked
and seduced by a divorced old man who’s also fucking my
sister. It was like I have nothing more to show to

“You’re the best fuck…too bad for the guys I got you
first…” he said mockingly and proudly.

“Please don’t tell anybody ok?” I begged meekly.

“Sure,” he said grinning as he leered at me. “I won’t tell
anyone how good a fuck you are… how you totally gave
in… and how nice it was to hear you moan and scream
in ecstasy….no, I won’t tell anyone so long as I get to
do this a few more times.”

The bastard was blackmailing me.

After a John left, I slowly got up, picked up my
clothes and dressed up. My head was still spinning from
the alcohol but I was already starting to curse myself
at the realization that I had put myself in a
vulnerable position and John took advantage and tricked
me. All of sudden, I realized how embarrassing it would
be if anybody finds out. Anne, the most sought after
lady in school…gave her virgin self to her sister’s
old divorced lover. And I knew I’d have to give myself to
him again. I started to sob in embarrassment.

It was four months later when I came up pregnant and
nothing has been the same ever since.

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