Am I Dating My Sister?
By: Date: 2021.05.05. Categories: Sex Stories Tags: , , ,

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

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

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

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

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

“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

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

“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.

(Visited 954 times, 3 visits today)