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Archive name: sherrie.txt (teens, rom, exh, reluc, 1st)
Authors name: Pleasure Boy 1 (pleasureboy_1@hotmail.com )
Story title : Sherrie Baby

--------------------------------------------------------
This work is copyrighted to the author © 2002.  Please
don't remove the author information or make any changes
to this story.  You may post freely to non-commercial
"free" sites, or in the "free" area of commercial sites.
Thank you for your consideration.
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Sherrie Baby (teens, rom, exh, reluc, 1st)
by Pleasure Boy 1 (pleasureboy_1@hotmail.com)

***

A young man discovers his best friend's little sister 
has the major hots for him and has gone to great lengths 
to ensure that she gets him in the sack. She's an 
extremely tight baby-faced teen.

***

Sleeping over at Danny's was always fun. We'd stay up 
watching movies until his parents were snoring loudly in 
the bedroom upstairs. Then we'd goof around playing 
cards and drinking pop. I never missed a chance to tease 
Danny's little sister Sherrie about everything I 
possibly could, but lately she had blossomed into a 
nubile young hottie and our teasing had turned into 
secret subtle flirting. She was 15. Danny and I were 17. 
We called her Sherrie Baby, after the song, and she 
hated it.

She did look sort of babyish though. She was a petite 
little blue-eyed blond with a pouty little mouth, and a 
cute little blush that made her look way more innocent 
than she really was. She had a baby face that could have 
let her pass for 11 or 12, and she hated it. She had a 
body that was beyond her years though. Her butt was 
particularly sweet. She wore a lot of tight clothes and 
make-up to hide her youthful looks, and this made us 
tease her all the more. 

She was a hottie though, and I think she knew I thought 
so, in spite of my treacherous taunting. She caught me 
looking at her below the waist for too long a few times, 
and a few times I caught her purposely showing off her 
assets down there, bending over for too long when she 
knew I was looking, letting her skirts ride up a little 
too high, giving me a glimpse of her panty-covered butt, 
and stuff like that. She loved the attention I gave her. 
I think this is why she always hung out with us even 
though she hated the teasing.

"You've never even seen a guy's dick! What are talking 
about?" Danny said to her in the middle of a 
conversation one fateful night.

"I have so. Lots of times," Sherrie retorted, flashing 
that innocent blush for me.

"Name one guy whose dick you've actually seen with you 
own eyes," Danny challenged her.

She glanced over at me. She was about to speak but just 
smirked and said "never mind". Then she left.

A moment later she came back. "I forgot my CD booklet," 
she said. She strode right up to me and bent at the 
waist to get it. My eyes fixed onto her smoothly curved 
backside and I had a sudden urge to reach out a grab it. 
I resisted though. Danny was sitting right there. 
Instead I gave her a playful little poke in the thigh 
with my forefinger where Danny couldn't see. She gave me 
a knowing look and left the room.

The look she gave me was an offshoot of the secret 
encounter she and I had shared a few months before. I 
had been spending the night just like always and a whole 
bottle of Coke was dumped on my head while roughhousing 
with Danny. So I went to take a shower. Unfortunately 
there were no towels in the upstairs bathroom so I had 
to sneak naked down the hall and duck into Danny's room 
soaking wet to look for a towel in there. Once inside I 
closed the door behind me and spun around. There was 
Sherrie laying across Danny's bed looking at my full 
frontal nudity with her big blue eyes wide open in 
shock. We stood in awkward silence for a few seconds 
before she finally tore her eyes away and made a 
pretence of girlish modesty.

The thought had occurred to me to cover myself, but at 
the last instant I changed my mind. I had teased her to 
death about being a sweet innocent virgin and I wanted 
to see her reaction to this new situation. So I just 
stood in front of her with my wang hanging in the breeze 
and she kept looking over at it, and away again, 
pretending to be "so embarrassed", yet she made no move 
to leave.

After a while I began flaunting my privates even more 
boldly, trying to see how far I could go. I began to 
develop an erection from the excitement of it all. I 
moved over and sat beside her on the bed and she turned 
the other way. Her face was red with the awkwardness of 
the scene. I teased her even more about finally seeing a 
guy naked and not even knowing what to do. She buried 
her face in the pillow beside my leg. I reached out and 
poked her in the thigh with my forefinger, as though 
prompting her to do something. At that she turned toward 
me with a sudden renewed boldness, looked directly at my 
hard on inches from her face and gave it a flick with 
the back of her hand.

"There! I just gave you a hand job," she said, and she 
got up and hurried out of the room.

That was the story behind the poke in the thigh and the 
sneaky little look she had given me. Ever since that 
night there was this secret dynamic between us. Our 
stabs and jabs began to have subtle suggestions between 
the lines, and there was always a look in her eye of 
seeing more of me than was outwardly shown. I had never 
told Danny about it. He would probably have beaten the 
crap out of me. He was pretty protective of his sister 
when the situation got beyond mere teasing. So I kept up 
the facade of pretending to tease her like a little 
girl, though in my heart I felt more and more excited by 
her every time I saw her.

So anyway back to that one fateful night. After Sherrie 
left Danny and I called it a night too. We had football 
practice the next day and we wanted to be in good shape 
for it. He headed to his room, and I went to sleep on 
the hide-a-bed in the basement. It was pitch black down 
there once the lights were out. You couldn't even see 
your hand in front of your face. I passed out almost 
immediately, dressed only in my undies.

....

I woke up a while later with a mouth on my cock. I 
thought it was a dream at first, as two hands felt their 
way around the foot of the bed and slid up my leg. I 
vaguely remember a warm, soft female body stretching out 
beside me and asking me if I was awake. I thought I'd 
responded but I wasn't sure if I really had, or merely 
dreamt I had. The next thing I knew a smooth and cool 
hand was sliding down my belly and into my underwear. 
All of the sudden these nice little fingers were wrapped 
around my cock and were slowly stroking me to hardness. 
Then my underwear was tugged down a bit and I felt 
gentle kisses winding a trail down to my belly button. 
All of the sudden my cock was inside a warm, wet, 
beautiful little mouth with sweet pouty lips and a 
slippery little tongue. I felt that little tongue 
swirling sensuously around it. That's when I realized it 
was actually real and not a dream, and I woke up.

"Oh, god.... That's so nice!" I whispered hotly in the 
dark. At that point I wasn't even certain who it was 
since it was pitch black, but after a few moments I knew 
it could only be Sherrie. I heard the soft breath from 
her nose, and this cute little purring sound she made in 
her throat gave her away.

Her sucking little mouth released my cock for a moment 
and spoke. "I'm sick and tired of being teased. I wanted 
to show you once and for all that I'm not just a little 
girl. I'm a real woman...." She moved down the bed to 
bring her face down level with my manhood as she spoke. 
I smiled in the dark as her hand wrapped around the base 
of my shaft and pumped up and down on it a few times. It 
felt so good! Then my cock was surrounded once again by 
the swirling pleasures of her lips and tongue, and that 
felt a thousand times better! 

My hands slid down to caress her lovely little head. She 
wasn't sucking hard or fast, her motions were not fancy, 
she was no expert at it or anything, but what skills she 
did have were more than adequate for a horny young guy 
like me. In fact it was my first blowjob as well. Though 
I talked big to her in front of Danny, I was in fact a 
virgin at the time. My only experience with sex had been 
reading a few magazines here and there, and peeking in 
on my older cousin screwing her boyfriend in my dad's 
bedroom when she was supposed to be baby sitting me. 
That had been years ago.

Now, all of the sudden I was getting my first blowjob, 
and it was so sweet! She gripped me in her wet slippery 
mouth with a steady suction and slid up and down on me 
while her hands massaged and tickled my scrotum. I 
panted and gasped ecstatically in the dark, lovingly 
tousling her hair. She continued this way for several 
beautiful head-spinning minutes and I was rapidly 
brought over the brink of orgasmic heaven.

Every muscle in my body tensed up and I erupted into her 
mouth with a soft grunt, clutching her adorable little 
head in my trembling hands. Her nasal breathing 
quickened as I squirted the first jet of hot, sticky cum 
into her mouth. She pulled away slightly at the shock of 
it, and I thrust upward spasmodically, trying 
instinctively to get deeper back inside the source of 
the pleasure. I pulled her head down onto me again, 
desperately begging her not to stop with gasps and 
whimpers of agonized delight. She hesitantly continued 
her oral massage on my throbbing cock as I gushed out my 
orgasm to completion. More and more cum flooded up into 
her virginal mouth and finally she could take no more. 
She coughed and I felt the thick liquid spill down my 
shaft and onto my balls. It had become too much for her 
and she pulled away to gag. 

I meanwhile was drifting away into a dreamy teenage 
bliss. I felt like I was floating 3 feet above the bed. 
I was all gooey inside, and tingly, and all I could do 
was softly stroke her hair with unspeakable gratitude. 
My heart was pounding and I released each breath with a 
contented sigh as I wound down from the heights of 
pleasure she had brought me to.

"Are you ok?" I asked finally.

She nodded in the dark and I felt her chin bump into the 
shaft of my cock a couple times. It was wet and slimy 
with my male release. She cleared her throat quietly and 
poked me in the thigh with her forefinger.

"How was I?" she asked.

"Beautiful," I said. "You ever done that before?"

She wiped her chin on the edge of the bed sheet and 
wriggled up to lay beside me. "Nope," she replied 
cutely. "That's why I wanna know if I was any good."

"You were beautiful," I sighed. I reached out found her 
hand in the dark and placed it back on my cock. It was 
hot and throbbing, wet and sticky in the cool air of the 
basement. "Feel that?" I asked. "Look what you've done 
to me."

She squeezed and stroked my cock lovingly as we talked. 

"You have no idea how long I've been trying to work up 
the nerve to do that," she told me.

"Really?" I said, not really as shocked as I sounded.

"Ever since you first started sleeping over here," she 
said. "I've been sneaking down here at night and just 
watching you sleep, dreaming of sucking and fucking you 
one day, just like the chicks at school talk about by 
the back doors."

"Wow!" I said dumbly. All this time I thought it had 
started that night I walked in on her in Danny's room.

"One time I even felt you up in your sleep," she 
confessed. "After that I couldn't stand it anymore. The 
next weekend I worked out a plan to actually get a real 
look at you naked. It was me who dumped the Coke on your 
head that time so that you would have to shower. I had 
taken all the towels out of the bathroom while you were 
in there and waited in Danny's room cause I knew you 
would go in there. I even sent him out to the store for 
more Coke while you were upstairs in the shower. It was 
a perfect plan, and it worked."

"Way to go," I said.

"I was gonna try and fuck you that night but I chickened 
out. I was completely naked under that bathrobe you 
know?"

"Holy shit!" I chuckled.

"But seeing you naked that night and not doing anything 
about it only made things worse. After that I went nuts 
over you. You are all I think about everyday and I can't 
get your gorgeous body out of my mind. I was determined 
to find some way to fuck you. I even went on the pill to 
make sure I'd be ready when it happened. It's been so 
long since then and I've been working on a plan to get 
you alone down here ever since."

"Really?" I said dumbly again. I wanted to keep her 
talking because her gentle little stroking on my cock 
while she talked was so nice, plus I was really getting 
off on her cute little voice in my ear. Hearing that she 
was on the pill was a pleasant relief also, since I 
didn't have any condoms with me.

"Well it was me who told my mom to make you sleep down 
here from now on, instead of on the floor in Danny's 
room. I told him you guys were keeping me awake at night 
with your talking. So we got this hide-a-bed set up down 
here and that's how it's been for the past month."

I began to guide her hand in stroking me just the way I 
like it, she obeyed without thinking as she continued 
her story.

"So anyway, every weekend since then I've been sneaking 
down here trying to work up the nerve to jump your 
bones, but I just couldn't. I wasn't sure how you would 
react. I didn't want you to laugh at me and tell Danny 
any stupid stuff about me. So every weekend I've been 
coming down here and just staring at you and fantasizing 
about it."

"Until tonight?" I asked. "What finally changed your 
mind?"

"I've been reading books about how to give head. I 
figured maybe if I surprised you like that in your sleep 
you wouldn't have a heart to tease me anymore. I wanted 
to give you the best head you've ever gotten so that 
you'll never tease me again."

"It was," I said. "Honestly, it was." I didn't have the 
heart to tell her it was the only head I'd ever gotten.

"Thanks," she replied.

"Wait a minute. You said you came down here to stare at 
me, but it's pitch black down here."

Sherrie let go of my cock, reached into her nightshirt 
pocket and pulled out a cigarette lighter. With a flick 
of her thumb it sparked to life and we were bathed in 
its soft flickering light. 

"You're gorgeous in this light," she smiled.

"So are you," I replied.

"You wanna fuck me now?" she asked.

"Sure thing, Sherrie Baby," I smirked.

The lighter flicked out and I felt her pull her 
nightshirt over her head. I didn't feel her pull any 
panties off. She must have really planned ahead. I felt 
her naked breasts press into my shoulder and I reached 
over and pulled her into a kiss. Her lips tasted salty 
and I suddenly realized I was kissing my own come. Yuck! 
I'd forgotten about that. Oh well. She deserved a good 
kiss after that performance. 

I reached down to grab her ass while we kissed. It was 
everything I'd imagined and more. Not only did I have 
the pleasure of feeling up her squirming little ass, but 
the rest of her nubile young body was pressed against my 
naked flesh as well, and she was ready and willing to 
fuck me right there. I was overjoyed, but I took my 
time.

I gave her tits a good once over with my mouth, tongue 
and fingers and moved up to her neck and ears. All the 
things I'd seen guys do in movies. I felt her pubic hair 
grind hotly against my thigh and I reached down to feel 
up her vulva as well. The soft pubic hairs framed her 
puffy little mound nicely. I stroked them gently the way 
you might pet a kitten and she cooed in response. 

It was hot and slippery in between the labia. I felt 
around for the lump of her clit. I'd heard girls liked 
that. I found it at the apex of her labia and she 
pressed her pelvis forward into my hand at the pleasure 
of the contact. She was kissing my ear and she purred 
and panted as I massaged her little mound.

Next I slid a finger down and searcher for her hole. It 
was very hard to find and I was beginning to feel kind 
of silly after a while, but all of the sudden she 
reached her hand down and pressed my finger into a 
sweeter and tighter little vagina than I'd ever 
imagined. It was so tight I hadn't even been able to 
find it! How would I get my cock in there?

"Ooh! That's nice," she cooed. I swirled my finger 
around inside her for a few minutes and she clenched 
herself even tighter on me. 

"Please... fuck me now..." she begged.

Without further ado I slid over across the bed and 
pulled her into the spot I had been laying in. She 
opened her legs and I climbed in between them like a 
conquering warrior. We both trembled with excitement. I 
thought to ask her if she was sure she wanted to go 
through with this, but thought better of it. Thus far 
she had taken every initiative to get me into this 
situation. She obviously wanted it, possibly more than I 
did.

I felt the heat of her privates on my erection before I 
even touched her with it. The next thing we knew I was 
pressed up against it. The underside of my shaft slid 
deliciously in between her slippery little labia, but I 
couldn't find her vagina. I couldn't even find it with 
my fingers, never mind a big dumb cock! This might end 
up being difficult.

I pressed forward, up and down and all around but 
couldn't get it in. She even reached down to help me, 
guiding the tip up against the opening of her hole, but 
when I pushed forward my cock bent sideways and slid up 
and away from the target. Damn!

"Oops," she giggled sweetly. "Sorry. Try again."

I tried again, reaching my hand down to search around 
for the entrance, but lost it once again. She reached 
down to help once again, and once again I managed to get 
only the very tip of it in before it slipped away up 
across her belly. I would have been frustrated if I 
wasn't so damn excited.

Sherrie whimpered beneath me. She had been waiting to 
have my cock inside her for so long, and now the moment 
was happening and we discovered only intense 
frustration. We tried once again and failed again.

"What are we gonna do?" I asked. "You're too damn 
small."

"I'm sorry," she whispered, getting a little upset. "I 
can't help it."

"Well the tighter the better they say," I smiled. "If we 
could just get it in somehow."

She was frustrated alright. She wasn't about to let her 
moment of glory be lost due to an impediment in her 
physiology. She reached down with both hands, slid four 
fingers into her hole all at once and painfully 
stretched herself open to receive me.

"Now! Do it now!" She gasped and panted.

I obliged. With a quick aim and a strong forward thrust 
I was suddenly buried a few inches inside her vagina. 
She pulled her fingers away and reached up to grip my 
shoulders. I thrust forward some more and my cock bent 
again.

"Careful..." she breathed.

Very cautiously I pressed forward, sinking into the 
lubricated grip of her cunt muscles, which strained 
themselves to receive my width.

"Ah, man....Oh, fuck, Sherrie!" I stammered at the 
pleasure of the carnal contact. Her cunt seemed to be 
milking me with spasmodic clenching as she struggled to 
accommodate the penetration. I pulled out a bit to wet 
more of the length, and pressed forward again. I was 
finally fucking and it was so sweet!

"Oh...Sssss....So big-" she struggled to speak but I 
could tell she was having trouble with it. She thrashed 
her head back and forth on the pillow beneath me and I 
thrust forward aggressively again. I wasn't sure if she 
was in pain, or just being dramatic. Mostly I didn't 
care because I was dizzy with my own erotic drunkenness, 
but I thought I should at least ask. If it became too 
much for her she might make me stop and I was horrified 
at that notion.

"Ok, wait," she pleaded. "Just stop... for- ow! Please. 
Oh, ow it hurts..."

"Shhhh!" I whispered, trying to calm her. I slowed my 
pace a little and kept kissing her all over her face and 
neck.

"Is that ok? Does this hurt?" I asked with only 
distracted concern. I kept pushing in and out of her 
crushing vaginal grip, deeper and deeper as I spoke, 
focusing more on the pleasure of it than any protests 
she made. She didn't answer. She was breathing rapidly 
through clenched teeth. Her cunt was vibrating all 
around me and her legs were twitching and shuddering as 
I struggled against her closing them on me to block my 
advance. Finally I was buried to the hilt at the bottom 
of her cunt and I could not go any deeper. We both 
relaxed for a moment, trembling and panting in the 
intensity of the moment.

"Are you ok?" I asked gallantly. "Does it really hurt 
bad?"

"It hurts a whole fuckin' lot actually," she said in the 
darkness. "You just ripped through my cherry."

"What? When? I didn't feel anything!" I blurted quietly, 
my voice was shaking.

"It stretched at first as you entered me, and then it 
tore all together as you pressed forward. Man, did that 
ever hurt!"

"Sorry," I said humbly.

"Just take it easy, ok?" she said.

"Wow! Brave girl!" I complimented with genuine respect 
for her. I don't think I could handle what she had just 
gone through without screaming.

"Thanks," she said half heartedly, as distracted by the 
pain as I was by the pleasure.

"So now I'm officially your first fuck, hey?" I said 
proudly.

"Yeah," she said softly. "You are."

Her voice had a hint of happiness in it somewhere beyond 
the pain. It was as though she was as proud of herself 
as I was of myself. It had been her goal to fuck me for 
many months now and she had finally achieved it. In 
spite of the pain, she was happy.

Her tone of voice made my heart swoon as well. Just the 
sound of it, combined with the pure pleasure of being so 
intimately connected to her most secret parts was enough 
to make me almost want to cry. Even the smell of her 
hair was beautiful. I leaned down to kiss her.

"You're my first too, Sherrie," I confessed.

"Oh my god! Really?" she gasped.

"Yeah," I answered. "I talked and joke a lot but the 
truth is I've never even been with a girl."

She was silent. I lay still inside her, feeling her 
twitch and throb all around me as the moments passed. 
Then she sniffled.

"That's so beautiful," her voice cracked. 

"What is?" I asked.

"That we could be each other's first. I'll never forget 
this night as long as I live..." She was crying now, 
tears of joy and overwhelming erotic emotions. 

"Me neither," I responded. Her tears were melting my 
heart as well. The whole scene was as beautiful as she 
had said it was.

"I love you," she said after a few more moments, and 
began to move beneath me, cringing a bit as she awaited 
my response.

"I love you too, Sherrie," I said. I'm not sure if I 
really did, but one thing I knew for sure was that I 
loved the feel of her pelvis dragging her cunt around on 
my cock. I began to fuck her. It was a slow and gentle 
fuck, cautious and full of emotion. Our heart pounded 
wildly in our chests and we broke from kissing only to 
grab a few gasping breaths now and then.

"Fuck me, baby!" Sherrie cried quietly. "Come inside me! 
I wanna feel it."

Her sudden burst of dirty talk was more than my little 
teen-aged mind could handle. I was shocked into a 
premature orgasm. I took a few more thrusts and let go 
of my impatient load. It squirted out of me almost from 
the very bottom of my soul. I felt like I was dying for 
a moment as I came inside her for the first time. Our 
bodies locked together in a sudden winding and slow, 
passionate release of erotic tension. I filled her 
vagina with my semen, taking a few more helpless little 
thrusts into her cervix and finally collapsed onto her.

"Oh, god! I love you, I love you, I love you..." she 
said over and over. There were tears in my eyes too as 
the boundaries between our hearts and minds and bodies 
were blurred by the all-consuming ecstasy of the moment. 
She kissed my tears away as they spilled down my cheeks 
and I felt myself falling for her, totally and 
completely. Her feet slid up and down the backs of my 
thighs and her fingers played in my hair. I kissed her 
over and over again and the minutes passed away. When we 
finally caught our breath I dragged my cock out of her 
tight vaginal suction and rolled over to lay beside her.

We talked for a while more, promising each other a 
repeat performance soon, and many times over. I'd gotten 
myself a nice sexy little girlfriend literally over 
night and I couldn't have been happier. 

Eventually She headed upstairs and I fell asleep for a 
long time. When Danny came in to wake me for football 
practice he asked me what the hell was with the 
bloodstain on the sheets. I told him I must have lain on 
something in the night (pun intended). He dismissed it. 
Later I told him that I was interested in seeing his 
sister Sherrie. I thought he would flip out and beat the 
hell out of me, but he just laughed and said he knew 
something was going on all along.

Thus began my many sexual adventures with Sherrie, who 
turned out to be a seriously hot little fuck once we got 
used to the whole concept of sex. She eventually became 
an expert at giving head too, and she prided herself on 
being able to get me off in under 3 minutes, any time, 
anywhere. I was the luckiest man alive. Perhaps I'll 
tell you more about it some other time.

END

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
This story was written as an adult fantasy. The author
does not condone the described behavior in real life in
anyway shape or form. 

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Kristen's collection - Directory 18