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Am I Dating My Sister?
by Lefty (leftyhandman@gmail.com)

***

After sending his daughter back to her mother's for 
the new school year, a recently divorced man 
reconnects with his sister, who also suffered a 
divorce. A night out sparks his fantasies. (M-solo, 
mast)

***

Part 1

Life can take you to some strange places. What I 
noticed are parallels. I was 19 years old, met a girl 
at a party, and we hooked up. Nothing grand, or 
romantic. She was cute, stacked, a little buzzed, and 
ready for fun. So was I, and fun was had. Three weeks 
later I got the phone call. I was going to be a daddy.

We met over drinks, non-alcoholic for her, beer for 
me. We talked for hours over what to do, but I think 
we got the big questions out of the way first. Was she 
going to have the baby? Yes. Was she going to keep it? 
Yes. If not, would I? Yes. Were we going to marry? Big 
hell no.

This conversation started what would become one of the 
greatest friendships of my life, and gave me its 
greatest joy. Our daughter. We love each other now, 
but not in the marriage way. We have no romantic 
passion between us, only concern for the wellbeing of 
our daughter. Our friendship became such, that when 
she married six years ago, I gave her away in the 
stead of her father who had passed away the year 
before.

What does this have to do with parallels? Fair enough.

I have a little sister, Sara. She is two years younger 
than me. She and her high school sweetheart went to 
the same college, did really well their freshman year, 
and married over the summer, just after she turned 
nineteen. Six months later she caught pregnant, and 
had a daughter when she was twenty.

All right, so it's not much of a parallel, but it's a 
major moment in a person's life. For my sister and I, 
we each became parents at the age of twenty. For both 
of us, it was a great start. For me, and the mother of 
my child, it carried on. My sister didn't fare as 
well.

Sara dropped out of college at the end of her 
sophomore year to have her daughter, with the promise 
that when her husband graduated, and got started in 
his career, she would go back to finish her degree. Of 
course this never happened. Time passed, and he lost 
interest in her, and their children. His surprise 
graduation gift was the birth of another child, a 
second daughter.

Yet, like many high school sweethearts, when the boy 
goes out into the world, he realizes there are other 
women out there. He's only tried one, so he wonders 
what the others are like. Sara was too busy with the 
girls to notice her husband's wandering eye, and how 
quickly the zipper on his pants would drop.

He was caught cold, though. In bed with the wife, and 
fifteen year old daughter, of one of his firm's 
partners. The girl alone was clearly enough to send 
him to jail, but that's not why they were even looking 
for him. The partner knew about his wife's affair, he 
was ready to ditch her anyway, but he had to be held 
back when he learned of his daughter's involvement. 
The real reason they were hunting him down was the 
money he had embezzled from the company. For the 
partner, the affair was a clean excuse for the divorce 
he wanted. Sara's husband learned soon after, that in 
jail, he was the bait.

Sara had filed for divorce before he even went to 
court.

Things may have been better for me, but not perfect. I 
married when I was twenty-six. Lara, my great friend, 
and mother of my child, served as my 'best man'. I 
wouldn't have anyone else. She threw me a great 
bachelor party. The two of us went for a weekend in 
Vegas. We got drunk, saw a couple shows, then spent 
the rest of our time locked in our luxury suite 
fucking each other silly. It was the first time we had 
sex together since she had gotten pregnant. The only 
time the door opened was for room service, and to 
bring in a new girl every now and again to entertain 
us. I think she was trying to give me an excuse to not 
get married, she never liked my bride.

Lara married two years later, and I threw her a Vegas 
bachelorette party to remember. I could describe that 
wild weekend before her wedding, but that would get 
away from this story, and has nothing to do with the 
parallels in life between me and my sister. These two 
weekends are the only times I ever cheated on my wife, 
and this second weekend I only did because my wife and 
I were in an off phase. We weren't having sex. Hell, 
we were barely talking, and when we did it was usually 
snide little remarks. Why we stayed together for eight 
years is beyond me. I may not have been perfect in the 
fidelity area, but it was limited to those two 
weekends. My wife it turned out was less inclined to 
fidelity than I was.

The final nail in the coffin for my marriage was my 
daughter, Stacy. She never liked her stepmother. I 
always kept a room in my house for her whenever she 
stayed with me, but after I married, and as she got 
older, she became less inclined to visit. I tried to 
chalk it up to the fact that she was becoming more 
independent at the boarding school Lara and I sent her 
to. It didn't help that my wife took her as reminder 
that I was able to father a child from a one night 
stand, and she seemed unable to give me one. It is my 
understanding now that with that much sperm floating 
in a woman's womb, pregnancy becomes less likely.

Stay away from the angry stuff, Mike. You stopped 
loving her a long time ago, anyway.

Sorry, had to get in a little self-affirmation. Our 
break up was quite recent, and while there is no love 
lost between us, it does still sting a little.

The last I spoke to her, before we signed our 
uncontested divorce papers, was during a fight. She 
brought it around to us being unable to have kids. 
Stacy had been out with some friends, and came home to 
her screaming step-mother. The bitch turned on my baby 
as soon as the door closed.

"And there's the center of all our problems right 
there!" she said, "You're probably the reason we can't 
have a child! God is punishing us for housing a queer 
little rug munching lesbo dyke, like you!"

Stacy came out to me two years ago, when she was 
twelve. I already knew. Anybody who spends ten minutes 
with her could tell. My wife over heard my daughter's 
confession, and was shocked. Scandalized. How could 
she possibly raise one of 'them'? I reminded her that 
since she doesn't live with us full time, she wasn't 
exactly raising my daughter. Well, here we are, two 
years later, and she's blaming her inability to get 
pregnant on my daughter's sexual orientation? 

I took two large steps across the room, and slapped 
her so hard, she staggered to the side.

"We're done. Get the fuck out, right now."

She clapped a hand to her cheek, and glared at me. 
Then her eyes widened, and she looked at Stacy. 

"Oh, my God!" she gasped, "Stacy, sweetie, I can't 
believe I said that!"

Stacy snorted, "I can. It's the only time you tell the 
truth. Just do what my Dad says, and get out you fat, 
bloated whore. Go find another dick to suck, maybe 
you'll finally get something straight in your head."

Stunned, she picked up her purse, took the keys to her 
car off the hook on the wall, and she walked out. 
Stacy ran over to me, jumped up, throwing her arms 
around my neck, and her legs around my waist.

"I'm sorry, Daddy, but I am so glad she's gone."

If you do the math here, you'll realize my sister and 
I divorced at the same time. Not the two year 
difference we've had so far for our parallels, but 
still, it happened. 

I am 34 years old now, my sister is 32. We both found 
new employment, in a new town, and are living just a 
few blocks from each other. Sara rented a small two 
bedroom house for her, and her daughters. Becky and 
Susie are now 12 and 10 years old, respectively. Their 
house is fairly utilitarian. The money they had before 
was taken back by her ex-husband's company, since it 
was really theirs, but they did let her keep an amount 
that was equivalent to his severance package. They 
weren't going to punish her, or her daughters, for her 
husband's mistakes.

I was able to buy a huge four bedroom condo. I went 
the condo route because I hate taking care of a yard, 
yet I prefer to own. Stacy has her own room, of 
course, and I have the master bedroom. The other two 
rooms I set up as a guest bedroom, and a home office. 
Stacy helped me decorate the rest of the house. She 
spent her last two weeks before returning to school 
helping me paint, and shop for furniture. By the time 
it was finished, I had to take her to the airport to 
fly back to her Mom's house for a few days. Lara would 
drive her to school from there. I kissed and hugged my 
baby good bye. It is always so hard to see her go, but 
after this summer, even more so. A lot happened, and 
she was there for all of it. Now she's going away 
until Christmas. 

I'll be all alone for the first time in eight years. 
What the hell am I going to do with myself until I go 
to work on Monday?

I got home, and was hit with a sudden urge to be 
anywhere but here. Everything about this place 
screamed Stacy. 

God, I love my little girl. 

I need a distraction. Food, unhealthy food. That's a 
good distraction.

I went into the kitchen, and put my hand on the 
refrigerator door, but I didn't open it. My attention 
was caught by a note. It just said Sara, and had her 
phone number scribbled under it. I stared at it a 
moment, considered, and decided fuck it. I need to get 
out.

I grabbed the phone, and punched in the number. It 
rang a few times, and then I heard a little girl's 
voice answer the phone.

"Hello?" she sing-songed into the phone.

"Susie?" I asked, "It's Uncle Mike. Is your mom 
there?"

"Hi, Uncle Mike, this is Becky! Hold on, I'll get Mom 
for you."

I then heard the phone thunk onto the counter top, and 
Becky screamed “Mom! Uncle Mike's on the phone!” 

I heard some other noises in the background, probably 
an admonishment for yelling like that. I heard what 
sounded like a faint 'sorry, mom', then I could hear 
my sister more clearly as she approached the phone 
receiver on the counter.

"Oh, never mind," I heard her say, "Would you help 
Susie with her reading assignment while I talk with 
your uncle?"

"Sure, Mom."

"Thanks, sweetie!" then she finally spoke into the 
phone, "Hey there, bro. Sorry about that, been a mad 
house here today. What's up?"

"It's okay, sis. I'm needing a little extra noise 
right now."

"Stacy went back to her mother's today, didn't she?"

"Yep, and now I'm realizing I am home alone for the 
first time in years. I may start chewing the walls 
soon. I have to get the hell out of here. Do you want 
to go do something? I'll pay for a babysitter."

"Are you trying to bribe me away from the terrible 
tweens? They are old enough to take care of themselves 
for an evening. Pick me up at eight."

I laughed, "See you at eight, sis."

We had a great time that night. Dinner, movie, drinks, 
she even talked me into dancing with her. We haven't 
done that since we were kids, and mom made us take 
ballroom dance lessons. It felt a little weird at 
first holding her that close. She's not an eight year 
stick girl anymore, but I came to enjoy being close to 
her. 

We talked a lot about what had been happening in our 
lives recently. Mainly our divorces, venting our anger 
over our spouse's infidelities. We even fessed up to 
each other about our own infidelities, limited as they 
were. I told her about the wild Vegas weekend I had 
before my wedding, and the one before Lara's. Sara 
told me about a two week affair she had with her 
middle aged neighbor lady around the time of my 
wedding. Sara broke it off when she found out it was 
just a game for her neighbor to spice up her sex life 
with her husband. Seems the tales of his wife's 
exploits seducing the neighborhood's young wives 
worked better than Viagra.

I was surprised we were having such a frank discussion 
of our sex lives. Growing up , Sara and I got along 
well enough, but aside from the dancing classes, we 
were never particularly close.

Her stories, and my memories, were having an effect 
upon me.

"Is it just me, or is this conversation just plain 
weird?" I asked when there was a lull in our words.

"Yes it is," she said, "but talking this stuff out 
with you has made me feel better about some things. 
Thank you for that, and for being my big brother."

We left shortly after that. I took her home, and 
walked her to the door. We gave each other a big hug, 
and as I went to kiss her cheek, she turned her head 
so our lips met. It was just a quick kiss, but we 
still held our hug after that.

"We have to do this again, sometime," she said, "I had 
fun tonight."

"How about you and the girls come spend an evening at 
my house later this week?" I offered, "We'll have a 
family movie night."

"That sounds really good."

So it was set. 

I went home, and crawled into bed. Unfortunately, I 
had a rampant erection that would not let me go to 
sleep. I could not get thoughts of Vegas out of my 
head. Well, I was starting to get used to taking care 
of myself.

I grabbed my cock, began to stroke, and ran through my 
fantasies to help me reach my peak. Lara makes 
frequent appearances in my fantasies, mostly because 
my greatest sexual experiences all involved her in 
some way. That, and she's just plain hot. 

We did try dating a few times before I got married. It 
was disastrous, we couldn't even get together to fuck. 
We're better off as friends, and occasional fuck 
buddies, even though we haven't done that since her 
bachelorette party. Still, she pops up in my mind when 
I need to make a personal release.

Tonight was different though. Not only did I start 
reliving the Vegas weekends, but something else 
started to creep into my thoughts. A sexy older woman 
seducing a younger married woman. The younger woman 
turned into my sister, no matter how much I tried 
making it Lara. Soon enough, the older lady became 
Lara, and we both began making love to Sara. I got
between her legs, spread her thighs, and began to eat 
her pussy. Lara was kissing her, and playing with her 
breasts. When Sara came all over my face, I moved up, 
and placed my hard cock at the entrance to her hot 
hole. Lara then squatted over Sara's face, and Sara 
grabbed her thighs, brought her mouth to Lara's pussy, 
and began to lick. I pushed into her wet cunt,
and began a steady rhythm.

Since this was just fantasy, this was enough to bring 
me off. I threw the covers off of me, and shot the 
largest load I'd had in a while. Two shots streaked up 
my chest, and the last actually managed to splash into 
my face.

"Yugh!... Ack!" I groaned as some of the splash slid 
into my mouth.

I got up, and ran into the bathroom, spitting my own 
cum into the sink. I then used a towel to clean myself 
up the rest of the way. I looked at myself in the 
mirror.

"What the fuck was that?" I asked my reflection. 

As usual the man in the mirror had no response. He 
just mocked me by mouthing my own words as I spoke. I 
finished cleaning myself, rinsed my mouth (yuck!), and 
got back into bed. Had to admit to myself, though, 
despite cumming in my own face, that was one hell of 
an orgasm.

End of part 1

Coming soon - “Am I Dating My Sister - 02” - Mike 
arranges the family movie night with his sister and 
her daughters, but also asks her out for another night 
on the town. Mike also has a Skype chat with his 
daughter, and her new girlfriend. The girls forget to 
hang up, and Mike over hears an intimate moment 
between them. (M/solo, mast, voyeur, f/f, teens, 
lesbian)

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Please keep this story, and all erotic stories out of
the hands of children. They should be outside playing
in the sunshine, not thinking about adult situations.

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Kristen's collection - Directory 79