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Am I Dating My Sister?

09/24/2024

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.