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Odds
by The Stork (address withhheld)

***

Back in the 60s, I somehow landed the hottest girl in 
school. But even hotter was the fling I had on the 
side... with her little sister. Would I get burned? 
(MF-teens, 1st, mast, oral, cheat, rom)

***

1968 may have been the Summer of Love in San Francisco, 
but in Iowa it was still the 50s. Good girls didn't, 
and they were all good girls. Not that it mattered much 
to me - pretty girls went for guys with money, and that 
sure wasn't me. My parents were both dead - my father 
in Korea, and my mom in a car accident a few years 
later. I lived in a trailer on the outskirts of town 
with my uncle; he didn't have much interest in raising 
a kid, so we mostly stayed out of each others' way. 

While the freedom that afforded, to drink, smoke, stay 
out late, etc., made me the envy of guys, girls still 
weren't too interested. Which is why I'm still amazed, 
all these years later, that I manage to get a date with 
Susie. She was too good for me on every level - her 
father was the town minister, her grandparents owned 
half the town, and to top it all off she was a stunner. 
The epitome of Midwestern wholesome beauty - shoulder-
length blonde hair, sky-blue eyes, flawless skin with a 
few freckles across the bridge of her nose. 

And, lest I forget, the most spectacular pair of 
breasts in town. Girls dressed conservatively in those 
days, but the heaviest sweater couldn't conceal those 
beauties. And when the weather got warm? I swear you 
could see the buttons straining on her school uniform 
shirt, trying to hold everything in. And it wasn't 
uncommon to see half the guys' zippers in school 
straining to hold in the hard-ons her massive mammaries 
inspired.

So how, with every guy in town drooling all over her, 
did I manage to get her to notice me, let alone say 
yes? We were at a school dance - she had avoided the 
boys all night, and was getting some punch, when a few 
football players came in, rip-roaring drunk. One 
staggered up to her, and told her loudly he wanted to 
rip her skirt off and fuck her until she screamed. Now, 
as dirty as that sounds here and now, imagine how that 
sounded in 1960s Iowa. 

Everyone, myself included, was shocked. Not one to see 
a lady so insulted, I walked up to the guy, and clocked 
him - I may not have been an athlete, but I had chopped 
enough wood and hauled enough scrap metal around for my 
uncle that I had strong arms, and a good right hook. I 
knocked him out cold.

Now, I didn't expect anything in return, but she 
thanked me, and after she looked me in the eyes for a 
moment, my heart pounding in anticipation, she kissed 
me. And not the demure kiss on the cheek I'd expect 
from a girl like her - a real kiss. I had kissed girls 
before, of course, but certainly not one like her. So, 
a few days later, I came to her house with a bouquet of 
flowers, and asked if I could take her to the movies. 
She blushed and said yes, and we were a couple.

Thus began the long, protracted battle familiar to all 
teenage boys, especially of that era - the battle to 
get into her pants. At the very least, I had to get 
those wonderful tits to myself. On the first few dates, 
I'd kiss her goodnight on her doorstep. After a few 
nights out, we'd sneak away someplace and make out, but 
even after an hour or more of swapping saliva, I never 
got any closer to getting her shirt off. Any time I'd 
move my hand anywhere near, she'd gently move it away. 
Every night, I went home with a massive boner and 
aching balls, and often jerked off two or three times 
in a row, imagining myself sucking on her nipples as I 
coated my belly with load after load of sticky white 
stuff.

I knew it was going to be a long time before I gained 
any ground. So imagine my shock when in one afternoon I 
got further with a girl I had just met than I ever had 
with Susie. I was at my locker one afternoon in school, 
when a dark-haired girl pushed my locker door shut, and 
said accusingly, "So, I hear you're dating Susie 
______." I knew the girl vaguely - she was a sophomore 
(Susie and I were seniors), and new in school that 
year. "Let's talk," she said, grabbing my hand and 
pulling me down the hall.

She pulled a key from inside her blouse, and opened the 
door to the faculty bathroom, dragging me inside after 
her. "So, you get anywhere with her?" Now, I expected 
that kind of talk from guys in the locker room, but 
certainly not from a girl, and an underclassman at 
that. I looked her up and down - she was skinny, with 
small breasts and slim hips (I couldn't help but check 
her out), and long black hair in pigtails. Most girls 
looked more innocent in pigtails, but she looked just 
the opposite.

"I bet you haven't," she continued. "That girl needs to 
loosen up." I managed to find my voice - "hey, how is 
this any of your business?" "Oh, it's my business," she 
insisted, without any explanation. "I'm guessing she 
teases you all night and sends you home frustrated?" I 
didn't say anything, but it must have been obvious from 
my non-reaction that she was right on the money. "You 
poor thing. That must be so... hard." As she said that, 
she rubbed her hand across the front of my pants. 
Naturally, I already had an erection. No girl had ever 
been so forward with me, and besides that, I was 18 - I 
pretty much always had an erection.

She slowly felt me up, as she asked, "she hasn't let 
you anywhere near those tits of hers, has she?" I 
slowly shook my head no, still in disbelief that a girl 
had her hand on my dick. "Well, these are no 
substitute," she said, unbuttoning a shirt button, "but 
you deserve a little something for being so patient." 
She was still holding on to my wrist with the hand that 
wasn't stroking my dick, and she moved my hand to her 
chest. Not being one to turn down so brazen an 
invitation, I slid my hand under her training bra, and 
slid it across her soft skin until I felt the nub of 
one of her nipples.

"Mmm..." she smiled and gave my cock a squeeze. Then as 
soon as my moment in heaven had started, it was over. 
She gently pulled my hand away, and released my cock 
from her grip. "Well, I've got to get to class. See you 
around." I was bewildered by what had just happened, 
when she left me with one last surprise. "Be good to my 
sister. I think she'll come around eventually."

Her sister? I didn't even know this girl's name! Who 
was her... then it hit me. This was Susie's sister. 
There had been whispers that her little sister had been 
sent off to reform school in junior high to avoid 
causing the family some disgrace, although what she 
could have done in junior high I can only imagine. I 
soon found out through the grapevine, her name was 
Natalie, and she had come back to regular school just 
this year.

For the next few days, I'd see Natalie in the hallway 
but she didn't acknowledge me. Friday afternoon, I was 
wrapped up thinking about my date with Susie that 
night, mentally plotting strategy to get a hand near 
any part of her boobs, when someone grabbed me from 
behind and dragged me into the teacher's bathroom.

"Hot date tonight?" Of course, it was Natalie. She went 
back to rubbing my dick through my pants, as if no time 
had passed since last time. "Think you'll get 
anywhere?" "Probably not," I muttered - I have no idea 
why I was even answering her - the whole situation was 
pretty fucked up. As much as I enjoyed what she was 
doing to my rock-hard penis, I put my hand on hers and 
stopped her stroking. "Jesus, I'm dating your sister. 
We shouldn't be doing this." 

She just smiled wickedly. "Of course we shouldn't." As 
she said that, she unzipped my pants, freeing my cock. 
It was the first time a girl had ever seen it in the 
flesh, and my heart just about stopped as she slipped 
her fingers around it and resumed stroking up and down.

I gasped for breath as she whispered low in my ear, "I 
bet you wish Susie would do this for you tonight. I bet 
you wanna suck on those big titties of hers while she 
touches you. You want her to kiss it - you want her to 
run her tongue all over—"

She stopped abruptly as I lost control and started 
spurting all over her hand. I had nothing to compare 
myself to at the time, but in later years women would 
tell me I produced a lot of cum. At the moment, it 
covered the back of her hand just about completely; it 
was in between her fingers, running in streams down my 
cock, and a long rope of it ran from the head of my 
penis to my belly. She smiled as she looked at the mess 
we had made, then calmly rinsed her hands in the sink, 
winked at me, and said, "I think you'll have some fun 
tonight, too."

Then she was gone, I was left standing in the bathroom 
with my dick hanging out and covered in sperm, and 
still horny as I had ever been in my life. I knew I was 
late for class, and I knew if a teacher walked into the 
bathroom I was fucked. But I couldn't help myself - I 
grabbed my cock, slick all over with my own juices, and 
started jerking off furiously. A few minutes later, I 
had a second load of cum running down my cock and onto 
my balls, as I imagined those white globs of sperm 
landing not all over Susie's tits, as my usual fantasy 
went, but up and down Natalie's wickedly smiling face.

The rest of the day dragged on, as I drove myself nuts 
thinking about the two girls, and what I wanted to do 
to both of them. I was so horny I had to leave 
Chemistry class to beat off again in the regular 
bathroom. Then when I got home, I shot one more load 
before I met up with Susie. I should have been spent, 
but by the time we pulled my uncle's car into the 
drive-in, I was rock hard again. (Damn, what I wouldn't 
give to have the stamina I had at 18 again)

We went to work fogging up the windows as usual, but 
this time things were different. About half an hour 
into the feature, Susie pulled my hand not away from 
her chest but towards it. She brought my hand to rest 
with her right nipple under my palm. I tentatively 
massaged her breast and she purred appreciatively. "I 
thought it was about time," she murmured. I kissed her 
passionately by way of agreement, and spent the rest of 
the night getting to know her spectacular assets. 
Through her bra and her shirt, but it was still better 
than I had hoped.

By the time I dropped her off at her house, my dick was 
ready to tear a hole in my pants - even after coming 
four times that day, I had been hard as a rock for the 
past two hours. I didn't even make it home - I pulled 
the car over just around the corner from her house, and 
unleashed the torrent of sperm that had been building 
up in my balls all night. I lay awake half the night, 
dreaming of Susie's swelling tits and Natalie's nimble 
fingers - needless to say, by the time I fell asleep, 
the sheets were a sticky mess.

So it went for the next few months. By tiny increments, 
Susie would let me go further and further. And every 
morning before I had a date with her, her sister would 
make sure she got me off first. By March, I was feeling 
up Susie through her bra, and sucking on Natalie's 
titties while she gave me a handjob. In April, I 
finally unclasped Susie's bra and got to suck on her 
fat, pink nipples just hours after her little sister 
gave me my first blowjob. 

The month after that, I finger-fucked Natalie until she 
came, and later the same night Susie touched my cock 
for the first time. Every time Susie let me go a bit 
further with her, Natalie went a bit further with me 
the same night. I finally worked out that Susie must 
have been telling her sister about her dates, and how 
far she intended to let me go. Natalie, acting out some 
kind of sibling rivalry, made sure to beat her to the 
punch. Yes, it was fucked up, but I was sure as hell 
enjoying it.

In fact, I was in heaven, except for two things. One, I 
was terrified Susie would find out. Natalie was 
unpredictable enough that she might very well spill the 
beans just to get to her sister. And everywhere Nat and 
I fooled around - besides that teacher's bathroom, we 
used empty classes, the woods behind the school, and 
even other people's unlocked cars a few times - we were 
likely to get caught, and expelled at the least.

But the second thing was even worse - in April I got my 
draft notice. Viet Nam. The way things worked back in 
those days, the lower your draft number, the more 
likely you were to get called up. Guys with numbers in 
the 5000s were running off to Canada. Mine was 214. I 
was virtually guaranteed to go. But since it was 
random, I still had a chance. I obsessively tried to 
work out the odds. It seemed like everywhere I turned 
was a bad outcome - even if the Army didn't get me, 
Susie might catch me with Natalie. Or their parents 
might catch me with Susie. Or Natalie. Or both.

I was walking a tightrope. But at the same time, I had 
two women - one cute and eager, and one unattainable 
and gradually relenting - both taking me further with 
me than I thought I'd get before my wedding night. I 
was in heaven and hell.

Prom night came in June. Susie had hinted that she was 
going to make the night special, so I saved up enough 
money for a motel room two towns over. And if she was 
going to make things special, I had a feeling Natalie 
would too.

Saturday, the morning of the prom, I was trying on the 
suit my uncle had bought me ("You'll need it for 
funerals and such anyway," he told me), when I heard a 
knock at the door of the trailer. It was Natalie. I had 
never taken either sister anywhere near my place, as 
shabby as it was compared to their big house on the 
hill, but in a town as small as ours, it wasn't hard to 
find out where someone lived. "Is anyone around?" she 
asked. "My uncle's working, and after that he's 
drinking - he won't be back until after I go pick up 
your sister."

There was an awkward silence. I never brought up Susie 
in front of Nat. She paused for a long moment, maybe 
deciding on whether to go through with what came next, 
maybe reflecting on yet another betrayal she was 
inflicting on her unsuspecting sibling. Finally she 
walked up and kissed me. My dress shirt was still 
unbuttoned, and she slid it off my arms. 

I reached for the straps of her dress - it almost being 
summer, she was wearing a pretty yellow sundress, which 
I was now sliding off her shoulders. As I slid the 
dress down further, I was pleasantly shocked to see 
that she wasn't wearing a bra. Maybe hippies went 
braless back then, but it was unthinkable in our neck 
of the woods.

She slid her hands across my chest, and then over my 
shoulders as she pulled me closer to her. I attacked 
her left breast with my mouth, first rolling my tongue 
across her nipple, then tugging on it with my teeth. 
"John." She almost never spoke my name, and it got my 
attention. I backed off of her as she looked into my 
eyes and said, "I want to go all the way with you."

I knew it had something to do with prom night, and what 
I was going to end up doing with Susie that evening. I 
was dying to ask her why - was she getting back at her? 
Did she feel inferior to her older, more popular 
sibling, and this was her way of evening the score? I 
knew if I breathed a word about the situation, I'd fuck 
things up. So I just stood back and watched, mouth 
agape, as she let the dress fall from her hips and 
slide down her legs. 

She stood there wearing only cotton panties, as she 
watched me slide my pants and briefs to the floor, 
completely naked before her for the first time. I 
grabbed the waistband of her underwear, pulling her 
towards me and kissing her again, one hand pulling her 
closer, the other reaching inside her panties and 
rubbing against her mound.

"Are you sure?" I whispered, as my middle finger found 
her wet slit. "Oh yes," she moaned, as her fingers 
slowly encircled my balls. "You want me to take you?" I 
asked again, as I slid a finger inside of her, while 
with my other hand, I slid her panties over her ass and 
down to her knees. "Oh God," she whispered, as her hand 
slid up and down my stiff cock as it had so many times 
before.

I walked away and opened the door to my bedroom, and 
turned around to look at her. "God, you're beautiful," 
I said. I go on a lot about Susie's looks, as all the 
guys did, but Natalie was pretty in her own right, and 
standing there nude, in my dingy trailer, brazen but 
still a little scared, she was the most beautiful thing 
I had ever seen. 

She waited a moment, then pounced on me, laughing as we 
both fell into the bed. Before long, I was on top of 
her, my cock rubbing against her slit, my hands mauling 
her little tits, and my mouth giving her a neck a 
hickey she'd have to hide from her sister for the rest 
of the week.

She bucked her hips up and down, grinding her clit into 
my shaft. "I'm ready," she said. "Put it in me." As she 
spoke the words, she raised up her ass so the head of 
my cock was resting right in the entrance to her 
innermost recesses. I slid the head in, and the feeling 
of her warm, wet pussy on my bare cock was the best 
thing I had ever felt in my life. I thrust into her 
until I was pressing up against her maidenhead. "This 
might hurt." She kissed me and bit my lip. "I can take 
it."

I grabbed her ass, pulling her towards me as I thrust 
harder. She cried out as I broke through her virginity, 
and then cried out again - in pleasure, this time - as 
I thrust into her fully, my entire length buried inside 
of her. She wrapped her legs around my ass, and pulled 
me deeper inside her as her hips thrust towards me. In 
turn, I thrust my hips towards her, grinding my pubic 
bone against her clit, and savoring every exquisite 
second of my cock sliding in and out of her.

Now, I didn't know a heck of a lot about the birds and 
the bees. My parents died before they got a chance to 
share anything, and my uncle didn't care to say much. 
But I knew there was a chance I could get her pregnant. 
Condoms existed back in those days, but they were for 
sailors and big city folk. Besides, a teenager couldn't 
go into the drugstore and announce to a druggist who 
knew his family and everyone else in town that he was 
going to fuck the minister's teenage daughter.

So I took my chances. In the back of my mind, I knew it 
was a risk. I knew I now had one more undesirable 
outcome to add to the list of a vengeful girlfriend, 
murderous parents, and the army. But that afternoon, 
with our bodies entwined, fucking a woman for the first 
time, any consequence was worth it. I was delirious as 
Natalie continued to use her body to egg me on, 
squeezing my cock with her tight virgin hole; clawing 
at my back desperately as she whispered "don't stop"; 
letting me slide halfway out, then grabbing my ass and 
slamming back in deep; there was no doubt she wanted me 
as desperately as I wanted her. 

They say you never forget your first time - I'm not 
sure, in all the years since, I ever topped it. 
Finally, our thrusting into each other reached a 
frantic pace, and I cried out as I shot jet after jet 
of hot seed into the depths of her womb. I held her for 
a long time, kissing her tenderly, my cock buried in 
her until it finally went soft.

I pulled out, and sat up to look at her, lying naked in 
my bed, drenched in sweat, breathless and sated. I 
looked between her legs, and could see a thick glob of 
sticky, white sperm sliding out of her soaking wet hole 
and down the crack of her ass. It was the most erotic 
sight I had ever seen, so I decided to look up close. 
Her sex was pink and glistening with both of our 
juices, and the intoxicating smell of sex was 
overpowering. 

I stuck out my tongue, and licked up and down her slit. 
She gasped - as many times as she had sucked me off, 
this is the first time I ever got close enough to taste 
her. She panted and moaned as I slid my tongue across 
her lips, then pushed it into her clit. I didn't even 
care that I was licking up my own sperm - I was 
incredibly aroused, and by the time she came, screaming 
to high heaven, I was rock-hard again.

I barely gave her time to catch my breath before I 
thrust back into her and resumed pounding her pussy. 
She squealed with delight as she felt my cockhead bang 
into her cervix. After a few minutes, she pushed me off 
her and said, "Let's try it this way," and she got on 
her hands and knees, her ass in the air, swaying 
seductively. She motioned for me to get on my knees 
behind her, but I had other plans. I grabbed her 
ankles, dragging her backwards until she was halfway 
off the bed. 

With her doubled over the edge of the bed, I spread her 
ass cheeks and licked my way from the top of her ass, 
down the crack (which was too soaked with both of our 
fluids to taste like anything other than sex), and down 
to the bottom of her pussy. I worked my tongue back up, 
past her ass, across the small of her back, and up her 
spine. By the time I got to the top, I bit her neck 
lightly as I thrust into her. She screamed with 
delight, burying her face into the sheets. It was only 
then that I realized I had positioned her head right 
where we had been fucking moments before.

I don't think she minded. In fact, I thought I saw her 
licking the bed at one point as I pounded into her from 
behind. I stretched her arms out, pinning her to the 
bed, holding her down as she humped the mattress and 
met my thrusts all in one motion. Before long, she 
cried out with another orgasm, which was enough to 
trigger another volley of sperm from my overworked 
cock.

We lay in bed for a while, teasing each other, fooling 
around, until it was time for me to take her big sister 
to the prom. I didn't say that, of course, I just said 
"I have to go soon." We showered together, and she 
kissed me passionately goodbye before leaving me to put 
my suit back on.

By comparison, my date with Susie was anticlimactic - 
how could it not be? We danced, we slipped some booze 
into our punch, we made out in the car, then drove to 
our motel room. It wasn't until we got to the room that 
I remembered I might be deflowering two girls that day. 
But it wasn't meant to be. Once our shirts were off, 
Susie assured me that she was saving sex for her 
wedding night, but that she still wanted to do 
something for me. She unbuttoned my pants, and 
proceeded to lick my sore cock up and down.

As far as she knew, this was my first blowjob, and 
should have been the highlight of my life to that 
point. Little did she suspect, I had already filled her 
little sister's hot snatch with three loads of come 
(did I mentioned we did it again in the shower?) and 
compared to that, her tongue barely registered. If 
Natalie wanted to show up her sister, she had succeeded 
wildly.

Still, a blowjob's a blowjob, and I did my best to act 
like it was a life-changing experience. Susie seemed 
caught off guard when the first jet of sperm hit her 
tongue, but she didn't back off. I kissed her 
afterwards, then surprised her by reciprocating, eating 
her pussy and thinking all the time about her sister's.

I dropped her off around 3AM, and she showed me how she 
climbed the oak tree outside her window to sneak into 
the house when she had to. She told me that now, after 
I dropped her off, I could sneak back to the house and 
come up to her room. As she closed the curtains, I 
turned around back to the car, only to see a face in 
the downstairs window - Natalie's. Her bedroom was on 
the first floor. She opened the window as quietly as 
she could, and whispered, "Hot date?" It had become our 
running joke. "You'll have to come by and tell me about 
it some time," indicating I could sneak in through her 
window some time soon.

As I walked away, I looked from one window to the next 
- one belonging to my girlfriend, one belonging to the 
girl I had just lost my virginity to. I felt a swirl of 
emotion - thrilling lust at the day's events, and 
paralyzing fear at the many ways it could all go 
horribly wrong. It was going to be a hell of a summer.

END

* * * * * * * * * * * * * * * * * * * * * * * * * * * *
It's okay to *READ* stories about unprotected sex with
others outside a monogamous relationship. But it isn't
okay to *HAVE* unprotected sex with people other than
a trusted partner. 4-million people around the world 
contract HIV every year. You only have one body per 
lifetime, so take good care of it!
* * * * * * * * * * * * * * * * * * * * * * * * * * * *
Kristen's collection - Directory 53