The Problem with My Sister

I have a problem. I assumed I was the only person in the world that has ever really had a romantic leaning toward a sibling. It’s a bit involved but I will try to tell the story as briefly as I can while giving it adequate context.

I was born the youngest of four kids in the early 90s. My name is Josh and the birth order is

Marie is the oldest, Leanna is the middle sister, then my older brother Zach. We are all roughly a couple of years apart and were homeschooled for the most part in a medium-sized midwest town. By the time I was high school age, my mom was over homeschooling and I was able to attend a traditional high school with my brother. We were also a devout church-attending family but at about the time I started high school, my parents became disenchanted by organized religion and we were all left to practice as we felt led.

In retrospect, it appeared that our parents were protecting the girls from the sins of the world but my brother and I would have to deal with life on our own. Being the youngest my tastes for rebellion seemed in line with expectations so I did as I pleased. This always bothered my older sister Marie but Leanna always seemed cool with how I was and it was around this time I really became infatuated with her. I don’t really know what it was but there always seemed to be a natural connection between Leanna and me. It was during my teenage years that I realized my connection with Leanna was anything but normal.

An example of this was my first successful masturbation session was after accidentally seeing Leanna in her undies. Basically, all of my fantasies early in life were about my sister. I even dated girls as close as I could to my sisters’ appearance which was hard to find. When she had finished growing she was tall for a girl (5’9″) with an athletic build and reddish-brown hair. Later in my teens, I even used a porn star search website that allowed me to put in my sister’s face and find similar-looking porn stars. The closest fit was Cassie Young who unfortunately left the business around 2018.

As you can see my lust for my sister was over the top and even when she had gotten married and had a couple of kids, I still had the same feelings I had harbored from my youth, maybe worse. She remained the kindest to me of all my siblings and since she was sheltered and church-raised beyond my experience, there was never a proper setting to share anything beyond a normal affection of a close brother and sister.

My only safe outlet for all of the lustful energy I was producing was with my girlfriends. That’s not really the right word. It’s better categorized to say I had three girls similar to Leanna in one way or another that were my fuck buddies. I’m a charming and good-looking guy, so having this arrangement worked out well and I was good at my craft. I learned early how to please the ladies pretending they were all my sister. I love oral both eating pussy and ass and although not everyone is into it, these girls seem to be. That’s why pretending to go down on my sis or tongue fucking her ass is one of the quickest ways for me to get going. If you’re going to be a dirty boy you might as well go all the way.

A few years ago, my problem hit a fever pitch and I decided that the only way to free myself from this fascination with my sister was to join the marines and get the heck out of the country. Maybe getting away and seeing new sites and people would free me from this cage of lust for my sister where I found myself. So on my 25th birthday, I enlisted and was scheduled to be in southern California for basic training. Having never traveled in that direction I kinda wanted to road trip out but didn’t want to leave my car there so my brother was going to go with me to drive the car back. Everything was set until his girlfriend got needy so my brother asked Leanna if she would fill in. She jumped at the chance for a little adventure away from her kids.

So there we were, the object of my lust for most of my young life and I headed across the county. We launched around 5 am to get a good jump on the day and we were a little quiet other than normal pleasantries. At some point to break the silence Leanna said, “Look Josh, I’m sorry that Zach couldn’t come with you as you wanted and here you are stuck with me.”

“Are you kidding me?” I said, “You’re my favorite out of the entire family, I just didn’t want to trouble you with the kids and all.”

“Well, I’m glad we got that out of the way. I will always jump at the chance to temporarily abandon my mom life for a little adventure and, you are my favorite as well.”

With that, we spent the next hour talking about the connection we shared and it seemed that we both felt part of the family but still on the outside looking in. I learned that Leanna never really wanted to have kids and she was pressured into the mom role by her husband Jason and partially by our mother. She also felt a little cheated by remaining a virgin since marriage when her husband was able to play the field as it were before they settled down. Since we were being so chummy she said, “I don’t even know if he’s a good fuck or not since I have nothing to compare to.”

A little shocked by her language I said, “Wow sis, I’ve never heard you use the F-Word before.”

“Oh little brother, there’s a lot you don’t know about me.”

“Like you secretly have a potty mouth?” I inquired.

“It’s one of the rebellions I kinda keep to myself. But I figure since I’m about to turn 30 it’s time I allowed myself to talk like a big girl,” she said with a wink.

“What else do you keep hidden in that rebellous little mind of yours?”

“Nothing that I want to share speeding down the highway. Maybe if we decide to stop somewhere for the night we can talk more after a couple of drinks.”

“So you’re a drinker now too?”

“I’ve always liked the taste of flavored whiskeys, but I hate beer and wine. Cocktails have too much sugar so yeah, I like a shot or two every once and a while.”

“Well, I had planned for us to drive straight through but the thought of getting drunk with my favorite sister is appealing.”

“Who said anything about getting drunk? I’ve never been drunk nor do I want to. I like to be in control of my actions too much but it’s nice to feel all warm on the inside from time to time.”

“Ok, two shots it is and I’ll keep you honest.”

My mind was going a million miles an hour as I was trying to understand what I was learning about my sister while at the same time I wanted to live in the moment and enjoy our connection. Hanging with Leanna was so natural it seemed like we were more alike than I realized. About the time we hit Albuquerque New Mexico it was getting late and there appeared to be a traffic back up on the highway west of town. Leanna was driving and unexpectedly exited the highway and pulled into a higher-end chain hotel and handed me two $20.00 bills.

“What’s this for?”

“I would like for you to trot over to that store and buy us a bottle of Old Camp, Peach Pecan flavored and I will get us a room.”

“Sis, this hotel is a little higher end than I had budgeted and,”

She interrupted and said,” Look, Josh, we’ve spent most of our lives rising out of poverty, and Jason and I have been doing pretty well. Let me handle the food and lodging on this trip as a going away gift.”

“Wow, that is very generous sis! Are you sure?”

“Of course! Now get going and I will text you the room number and order some takeout.”

With that, we divided and conquered and I had the room number by the time I had the bottle. I approached the correct door and knocked but it took a bit before she opened up.

“Sorry for the wait, I wanted to grab a quick shower before you returned but you were too fast!”

“No worries, be careful with that towel, we don’t want to overshare before you’ve been drinking.”

“You mean be careful not to scar you for life seeing my mom bod?”

“Ok that’s ridiculous. You are one of the best-built women on the planet.”

Her smile and shrug told me she knew I was right. She trains nearly every day and has the muscle and build to prove it.

“I do work hard so thank you for that. Not everybody likes the lean muscular look but I do and that’s important.”

At this point, I was pouring us some shots as she was headed into the bathroom to finish getting dressed. I handed her a plastic cup on the way by which she grabbed and downed in one gulp.

“That was a heavy pour there Josh, don’t get too heavy-handed or we both might regret it.”

“I doubt that there’s anything that could happen tonight that I would regret.”

With that, she paused and stared me down like she wanted to say something but did not. When she was finished she emerged in her normal athletic leggings and a tee-shirt and flopped down on one of the beds. I showered and came out in my boxers and tee shirt. She said, “So you’re going to make me see you in your boxers while we drink and have dinner?”

Thinking I had done something wrong I said, “I’m sorry sis, I didn’t mean to make you uncomfortable. I’ll put on some pants if you would prefer.”

“No, I will allow this for now. It’s just that you have a very nice body as well and I want to be sure I am only thinking sisterly thoughts.”

Wow, was the alcohol already having an effect, or was this something more? I was excited and terrified at the same time and I needed to play it cool. I calmly stated, “Well if it becomes too hard for you to resist, just let me know and I will get dressed immediately.”

She laughed and threw a pillow saying, “You’re a cocky little bastard, one of your best qualities. Don’t ever lose that or let the military water you down.”

The food was taking a long time to arrive and we were getting more buzzed as we waited. I had turned the desk into the bar area and was relaxing in the office chair.

The second shot turned into a third and Leanna seemed really relaxed. “So Josh, tell me, how many fuck buddies do you have these days?”

Now, this was one of the characteristics I both loved and hated about my sister. She had a way of getting to the root of things. But if she was in a blunt mood I could certainly pace her. Looking like I was counting on my fingers I said “Three at the moment. Why do you ask? Do you have one of your cougar friends in mind for a fourth?”

“In your dreams loverboy. All of my friends are too vanilla for a stud like you.”

“How in the world would you have any idea how or who I am in my adult interactions?”

“Ok, first, you’re really bad at leaving your phone lying around unlocked at my house. Second, we still live in a relatively small community so people talk, and third, you never clean out your browser history on your laptop.”

Oh my God!!! I could feel my face get red from embarrassment. Did she know my little secret? Did she know I had a folder of her pictures I used from time to time? I felt so dead at that moment but yet at the same time she was smiling like she had won some great prize. And, why had she been snooping?

“Ok, what’s your game here?” I asked

After a long pause, she said, “No game, just having an authentic moment. You remember you asked in the car what else I was keeping in my rebellious little mind?”

“Yeah,” I responded hesitantly.

“Learning about your dirty little mind is one of my secrets I haven’t shared with anybody until now.”

“Like what have you figured out about me oh wise one?”

“I know all of your girlfriends look like me and most of your porn searches are for girls that look like me. I know you love eating pussy and apparently are into analingus if I’m saying that right. I know that you get nervous around me sometimes because secretly you have this problem of really wanting to fuck your sister.”

With that, she downed another shot and waited for my response which was only total shocked silence.

She continued, “And I know that since you’ve failed to protested or disagreed with anything I’ve said that I’m right. I also know that I have this problem that I also really want to let my brother do all of those nasty things to me that you think about. The problem is that we are brother and sister and beyond that, I”M MARRIED!”

At that point, the phone rang breaking the awkward silence and Leanna answered. Apparently, she had ordered pizza and it had arrived. She asked them to keep it downstairs and that one of us would be down later to get it. What did that mean? Why later?

Seeing my confused look answered, “Look, you’re going off to God knows where and I don’t know if you’re ever coming back. I have had an unholy hunger for you since we were little and just can’t shake it. I’ve loved you and wanted you before I was saved and before I was married so in my mind, we have some unfinished business. So, what I’m saying Josh, I know it’s wrong on so many levels, but would you be willing to make lov…no scratch that. Would you like to fuck your sister?”

Totally stunned, partially paralyzed but mostly excited I thought I should respond quickly, “More than you know,” was all I could get out. I started to move and she held up a hand.

“Ok buddy, I need to know something first.”

“Ok,” I nodded.

“Have you had your dick in anybody since you’ve last had a negative STD test without a condom?”

With still a bit of nervousness in my voice, I said, “I have not. I have never had an issue with that and I’ve been extra careful of late not wanting to have an issue in basic.”

“Good! I’m still on the pill so I’m good here.”

After a short pause and a deep breath, my sister slid out of bed and started to move my way. While still a step or two away she eased down to the floor on her hands and knees approaching me slowly and seductively.

“I have wanted to see your cock for a long time.”

She then put her hands on my boxers and worked my mostly hard cock out of the trap door. Her touch created a blood rush that finished the hardening process and she rubbed my cock on her right cheek. It was one of the sexiest sensations I had ever felt.

“You have a lovely cock little brother, I can see why you are so popular.”

“I still can’t believe this is happening. You have always been the object of my desire and I have never been so…”

“Turned on?” she interrupted. She laughed and said, “I know I’m ready for this and don’t expect this to last long.”

With that, she engulfed my cock and appeared to savory the flavor to a degree that I thought I would instantly cum. Sensing the gravity of the situation she immediately stopped and broke contact saying, “I have so much wanted your cock in my mouth but that’s not how this is going to end. I want you to cum in my pussy but not before you’ve gotten me off at least once with that tongue of yours.”

As she was talking she was standing up and moving back to the bed simultaneously removing her leggings. She turned and crawled on the bed flashing her glorious ass while arranging the pillows to lay on for her comfort. I said, “You seem to have this all planned out sis.”

“Well, I knew you would probably be down for anything I allowed so I have been holding all of the power. Assuming this would happen of course I have thought about how I wanted it to go.”

Still in her tee-shirt as she laid back with her legs tightly together and her hand covering her pussy. I approached her feet with my cock at full attention having shed my boxers and at that point, we locked eyes for what seemed like an eternity. She was smiling, I’m sure I was too and I almost asked something like, ‘are you sure?’ or ‘are you ready?’ but I’m smart enough to know that guys normally make a mistake by talking too much. Knowing she seemed to like her power position I decided on, “You made a request of me and I am here to fulfill it.”

She smiled and started to move her hand while slowly spreading her legs and I realized she wasn’t worried about being sure of her decision, but she wanted to be sure that I still wanted to go through with it. Her look became a little more devious as she said, “I was planning on making you beg to eat my pussy but I want your tongue in there so bad I don’t want to wait.”

“Same!” I said settling onto the bed between her legs and taking my first smell of what was splayed out before me. We never broke eye contact and I began to lick her pussy ever so gently until I saw her eyes close briefly to enjoy the sensation. I was in absolute heaven and didn’t really want this moment to end. After what felt like too little time Leanna said, “I love how you’re being sweet and sensual but if you don’t hurry up and tongue fuck this orgasm out of me I’m going to lose my mind!”

Being obedient, I picked up the speed and pressure and in no time she was moaning like crazy before clenching up and going totally silent. She was holding her breath as I saw her abs flex and her jaw clench and her eyes opened looking at me as she yelled, “Fucking finally! I’ve been waiting on you to do that for at least 15 years!”

We both laughed as I took a half-hearted attempt at wiping her cum off of my face.

“Same here sis. I’ve wanted this for so long I can’t even remember when it started.”

“Probably when you accidentally saw me in my undies right?”

“Oh yeah, I pumped my cock that night thinking of you.”

“Well, how about you pump that cock in me right now?”

“I totally agree.”

And with that, we went past the point of no return. She had the best feeling pussy I had ever felt and told her so as we were finally face to face for the first time. We hadn’t kissed yet and I assumed we wouldn’t be doing that now with her pussy juice all over my face. I was wrong. As she was cuming again right after entry she pulled my face down and kissed me hungrily. Almost like she was trying to consume all of her cum for future use.

We came up for air and she said, “I know you’re going to cum quickly if you don’t hold back but please, don’t hold back. I want you to fuck me right now with all you’ve got and pump every drop of your cum in my pussy.”

And fuck her I did. I was somehow able to last maybe another minute giving it all I had and she had to have cum at least two more times and it was glorious. As I was shooting streams of cum into her pussy I realized the reality of the moment. It was without a doubt the best sexual encounter of my entire life. As I pulled out and laid down next to her catching my breath it hit me that I had a new problem. I might as well plan my suicide now because nothing would live up to that.

“Leanna,” I said.

Interrupting she said, “Don’t screw this up now Josh. Just lay here with me for a few minutes while your cum leaks out of my pussy. When I say so you can get cleaned up, go get my pizza and do your best to recover because we are fucking as much as possible tonight.”

“Well, how lucky am I? All night?”

“Until we are tired or sore. We have another night on the road and I want to save something for later.”

“So this isn’t a one and done.”

She laughed and said, “Stopping what we’ve started won’t absolve us of our sins. There may be a day when this season is over, but until then we are going to enjoy our special connection as long as it serves us.”

She was using air quotes when she said special connect which caused up both to laugh. As that moment was settling I said, “It’s going to be nearly impossible to join the marines knowing what I’m leaving behind.”

“No, that’s the whole idea bro. You have to stay alive and healthy to come back to me. And we have to be super careful that nobody can even suspect, understand? I will shut this down in a heartbeat if you are anything but normal around the family. Also, you will fuck nobody without a condom while you’re away or you won’t fuck me at all when you get back understand? I’m trusting you on this.”

“Understood! You won’t have to worry about me.”

“Good, now that’s settled go got our pizza so we can carb load for the rest of the trip!”