The Problem with My Sister Ch. 02

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The Problem with my Sister Chapter 2 is a continuation of Chapter 1. All characters are 18 years or older.


I have a new problem. Sitting in the airport waiting for my plane to board I’m struck by how difficult it’s going to be to contain myself around my sister. Leanna and I have stayed very platonic in our text messages as was the plan prior to my departure. The best I can tell, Leanna has shared with the family she plans on always picking me up and returning me to the airport when I have leave during my tour of duty. Since the airport is in the city an hour away from our home town it seemed inconvenient but she assured everyone it was for luck. Also, Leanna likes to shop for furniture in the stores in the city even though she rarely buys anything.

Additionally, she has some friends in the city that have relocated there so she can visit them for coffee and it gives her a mental break from family life so that was an easy sell. She also convinced everyone that I should stay in the guest room at her house since she was going to be my ride to and from the airport. I had put my things in storage and moved only the necessary items back to my old room at mom and dad’s after I let my apartment go to join the Marines. The final part of what I know is that everyone thinks my plane is landing at 6 pm and they are planning a 7 pm homecoming at Leanna and Jason’s house. My nieces are working on decorations and mom is baking my favorites.

The fact is that my flight is actually scheduled to arrive at 4 pm. Leanna has mom and dad coming to her house to hang with the kids at 3 pm to make preparations. Jason was going to rework his schedule to watch the girls but Leanna didn’t want to put him out and the folks were happy to oblige. Beyond that, I knew nothing except it seemed like Leanna had something cooked up and I couldn’t wait. Finally arriving and walking down the jet bridge I kept reminding myself that I needed to be cool and stay casual when seeing Leanna in the public airport and wait until we were alone to be our authentic selves.

I could see my sister smiling just past security holding a sign that said WELCOME HOME BRO!!! Ok, so she was telling the world that I was her brother which meant a big hug and a peck on the cheek at best. “Be cool Josh” I repeated silently over and over again. The hug was tighter from her than I remember which meant she was really happy to see me or her weight lifting was making her stronger. We acted completely normal until we walked well past the terminal toward the far side of the lot. Being safely out of earshot from everyone I asked why she had parked so far away.

“Because little brother of mine, I am going to suck an enormous load of cum out of your beautiful cock before we leave for home.”

“Oh thank God,” I said, “I was partially afraid that our trip to California was a dream and I wasn’t actively fucking the girl of my dreams.”

“Oh, we’re fucking buddy. I have it all worked out. In fact, you are going to retake my virginity.”

“Well, I can’t wait to find out how that works.”

“Just relax loverboy and all of your questions will be answered.”

“Speaking of that, I do have some questions about a few things other than your plans for my time at home.”

“All in due time little brother,” She said while hitting the remote locks on her SUV, “but for now, throw your bag in the back and meet me in the front. I have a dick to suck and we’re wasting time talking.”

I’ve had several blowjobs in my day but I swear, Leanna sucked my dick like her life depended on it. Other than the frequent masturbating I enjoyed thinking of her I had no other sexual pleasure while at basic and so my load came fast and furious.

“Ah, such a good boy you are! If you don’t mind me riding back with cum breath I’m not going to rinse out my mouth, but just enjoy the taste for a while.”

“I’m good with whatever sis, I’m just glad to be here with you.”

She leaned over and gave me a little peck on the cheek and said, “You have about an hour to get good and recovered because I have special plans for us.”

Off we went, headed toward our home town and she shared how excited the girls were to learn that uncle Josh was going to be staying at their house and Jason was eager to hear about basic training. Her mention of my brother-in-law triggered my mind to recall some of the questions I had and asked if we could fill in some gaps on the drive back. “Fire away, but I reserve the right to not answer some things for now if I see the need.”

“Deal! Ok, the first question, You were raised more strict than I was, and yet somehow you have become an extremely passionate and knowledgeable person sexually. How did that happen?”

“So what you really want to know is how did I become such a freak or why am I such a freak to you?”

“Maybe a bit of both because let’s face it, Jason doesn’t strike me as the sexual champion type, and yet here we are.”

“Fair enough. First, you know my infatuation with you started long before I met Jason. Kıbrıs Escort I didn’t know a lot about sex but I knew how it worked and would dream about you and I losing our virginity to each other. I knew it was wrong and unholy but for some reason, that made it hotter.”

“Same for me.”

“Then I got married knowing Jason was not a virgin so I expected he would know enough for both of us and that just wasn’t the case. Losing my virginity to him was anything but pleasurable and for our entire marriage I have been the higher desire spouse.”

“I can definitely see that.”

“So, I spent a lot of time getting to know my body, what it liked and what I liked and did a lot of research on the internet if you know what I mean.”

“So you’re into porn?”

“Not so much porn but some of that. What I really got into was reading erotica and you know how powerful the mind can be and that’s also where I ran across incest stories.”

She paused for a bit so I encouraged her to continue.

“Every time I read a brother-sister story I pictured us. Josh, I have fucked you more in my mind than we ever might experience in real life but I’m willing to get it a try.”

She seemed to actually get a little emotional so I took her hand and tried to lighten the mood, “I know living out your fantasy with me is tough duty sis, but I’m willing to give it my all.”

She laughed which was the desired response, “Yeah I’m sure you will be up for the challenge which reminds me. We have to be so careful. It might even be good to act like we are pissed at each other around the family from time to time.”

“I’m good with method acting but we were never pissed at each other growing up so wouldn’t that seem out of place?”

“Maybe. Let me think about that some more later. Was that your only question?”

“No, but that answers a lot. Can I save the others for later and ask about your plan for today?”

“Oh yeah, this is so good. You know I have mom and dad watching the girls at my house and all of the family is getting there to greet you around 7.”

“That’s all I know.”

“The rest of my plan is we are going to mom and dad’s house and we are going to act out what I wanted to do years ago.”

“How so?”

“Well, the guest room was your room but now it’s basically back to your room. You are going to get in that bed and close your eyes and do everything you can to fantasize about the night of your 18th birthday. I am going to sneak in wearing the same type of white cotton underwear I was in when you first saw me less dressed than I was supposed to be which if memory serves was on that day. Got the picture so far?”

Becoming quickly recovered and aroused I voiced my understanding.

“I will then wake you with my mouth on your cock until you are good and hard. Then I am going to pretend that I am taking your virginity while you’re taking mine. “She paused again, getting noticeably aroused, “Just follow my lead because the mind can be very powerful when we use it correctly, you got me?”

“Message received loud and clear.”

For the rest of the trip, we relived a lot of our teenage experiences which really did an amazing job of setting the stage. We pulled into the driveway and she got out with a small bag she threw over her shoulder. She punched in the garage code and said, “I need you to grab a couple of items from your room while we are here which is going to be the reason that we had to stop on the way.”

“Why do we have to tell them we’re here?”

“Because mom and dad have this weird radar and whether it’s a wet towel or a damp shower floor they will know and I don’t want to have to wipe the place for prints. Also, you are going to throw your sheets in the wash and claim you were just being nice to be sure the bed is usable for guests if needed.”

“Wow, you’ve given this a lot of thought.”

“You have no idea. Now go get in your spot loverboy, close your eyes, and pretend you are my little virgin brother sleeping in his tighty whities and I will do the rest.”

I did as directed and even threw some towels up over the windows to make it darker. I was semi-erect due to a combination of the earlier blowjob and the pending excitement. I couldn’t help but peek when I heard the door open. While she was in the hallway I could see her in an old robe she had as a teenager and a white-looking training bra and matching white cotton panties just like I remembered from the first time I saw them. I tightened my eyes and tried to relax as I heard and felt her move closer. I felt her hands under the covers making contact with my shorts as she found my cock. She was stroking it on the outside of the fabric when I heard her ask, “Joshy are you awake?”

Staying in character and sounding sleepy I murmured a response and then asked in a groggy voice, “What are you doing?”

“Well, I was thinking. I’m going to be leaving the house soon and I’m leaving a virgin. You know what that means right? Has mom and dad had the sex talk with Magosa Escort you yet?”

“Yeah, I know how it works.”

“Good, and I’m guessing you’re a virgin too, right?”


I know it’s wrong to feel this way Joshy, but I don’t want to lose my virginity to just some guy, and I don’t think you should lose it to just some girl.”


“So would you be willing to take my virginity while I take yours?”

“Sis, I think that’s a great idea.”

“Ok, well I’m still a little shy and I want to stay dressed in case we get caught so you just lay there and let me take care of this.”

By this time she had my cock fished out of the trap door in my briefs and she straddled me moving the crotch of her panties over to the side for access

“Now this might hurt me at first so let me take care of this ok?”

“You got it sis and I want to say thank you for doing this for us. This is the best birthday present ever”

“I know it is. We have always been close and I can sense your energy around me. Plus your dick is so hard right now I can really tell you want this.”

She positioned my cock right at her opening and said, “This is it, Josh. After I lower myself on you we will no longer be virgins. Are you sure you’re ready for this?”

“I’m so ready if you are.”

“I am too. Here we go.”

As she started to lower herself she paused like she was painfully passing her hymen and her pussy felt incredibly tight. Like tighter than I remember. When she finally got past what would have been the painful part and bottomed out, she just slowly started rocking back and forth. Not just because it felt good to both of us but it was like she didn’t really know what to do.

“That feels really good sis,” I whispered like our pretend parents may hear us.

“It does for me too Joshy. Now you have to be careful that I don’t get pregnant so when you’re ready, tell me so I can move.”

Wow, she was really in character. The thought of our fertile bodies running the risk of impregnating my sister was enough to push me to the edge really fast.

“Ok, I think you better move,” and with the swiftness of real fear, she moved off my cock but pumped it until I shot cum all over us both.

“My God Josh that was a lot!”

“I’m sorry sis, you are just so sexy to me I couldn’t help it.”

“I actually think I like it,” she said, smearing some of it around but not taking a taste.

She added, “Now that we’ve done this, we might as well do it all the time right?”

“I like the way you think.”

And then she made a motion with her hand like in the theater and said, “End Scene.”

“Ok, Leanna, that was one of the most powerful sexual experiences of my entire life.”

“One of the most,” she questioned, slightly offended.

“I mean compared to our first time, the second time, basically everything with you has been more than I could hope for.”

“Good recovery loverboy. I wanted to stay in the scene but the little Joshy that just lost his virginity can’t eat pussy like I need to eat mine and I still need to cum.”

She immediately moved up and pinned my face down with her pussy until I got her off which took like 60 seconds. After she recovered we cuddled up for a bit and then I asked, “Was that really your old robe from when we lived here?”

“It was. Don’t really know why I kept it but I went and found it right when I got back from our trip.”

“You’ve been planning this since then?”

“I thought this up on the trip back. So, other than the robe and what I wore, did you notice anything else?”

“Like what?”

“How tight my pussy was? Like a virgin.”

“Now that you mention it I did. How did you do that?”

“Well, in addition to finding my robe I found extra time to do a ridiculous amount of pelvic floor training during your basic training and then I abstained from my normal weekly with Jason so I would be as tight as possible for you.”

“And I did notice. I mean how fast did you get me off? That was crazy!”

“And that was my plan, among other things.”

“Like what?”

“Like how you can really take my virginity.”

“Ok,” I said as a question.

“I know from reading erotica that the idea of a virgin ass isn’t new but honestly, you could be the first person in there.”

“Well I don’t hate that idea and if I’m being honest, I have tried it with one of my girlfriends and it didn’t go too well.”

“Could you not get it in or you didn’t get off?”

“I got in, but it wasn’t pleasurable and we stopped.”

“So cumming in my ass would be new for you?”


“Great, then we will both lose some virginity the night before you leave.”

“I like it, so what is the rest of your plan?”

“Your flight is leaving next Friday but you’re going to tell everyone it’s leaving Thursday. I have a room and I told Jason I was going to stay over to have lunch with a friend which I will do once you’re on your flight.”

“So I get a whole night Girne Escort with you.”

“Indeed you do. But until then, it’s hands-off or this snoopy family may suspect something. Let’s rinse off and wash the evidence.”

We got cleaned up and headed to Leanna’s house for the homecoming as it were. As we pulled up she reminded me, “Act as normal as possible. If there’s going to be any extracurricular activities, I will let you know,” She said with a wink.

Let the homecoming party begin. Getting back together with everyone was great and in the background system of my brain I kept hearing “If there’s going to be any extracurricular activities.” I would say she was becoming a tease but at the same time, I had never been happier. I mean what guy has a sister like this?

Staying at Leanna’s and Jason’s was great as I got to be uncle Josh to the nieces and the rest of the family wanted to take time with me on and off during the week. I had asked for all of the mornings to be for me so I could sleep in and rest up before being shipped off to additional training on my specialty which was mechanics. Everybody honored my wishes and when Monday rolled around, the girls needed to get back to school and everything was looking more normal for the rest of my family.

Around 9 am on Monday, I was getting up, having coffee and the house was empty. Just then Leanna came bounding in from the garage, “Morning sleepy head!”

“Hey sis, how’s your morning going?”

“Wonderful, would you like to hear about it?”

“I would and is it just us here at the moment?”

“It is and I have good news and bad news. First, my day started at 4am when I left to meet Wes and Ashley at the gym. I set a new deadlift personal best, pulling 300 for 2.”

“That’s a lot of weight for a skinny girl like you!”

“Skinny girl my ass. Anyway, I got home, had breakfast with Jason and the girls, and then dropped the girls off at school. So lucky for me now that you’re awake.”

“This all sounds great so where’s the bad news?”

“I said for you it was good news and bad news,” she said in a slower sultry voice and that’s when she pulled what appeared to be a butt plug from her purse.

“Where are you planning on putting that?” I asked, expecting the worst.

“I’m not putting it anywhere. You are going to gently insert this into my ass after you get me off with a combination of this plug, your tongue, and your fingers,” she added her signature wink.

“Ok I like that but I’m still lost on the bad news.”

“You see bro it’s like this. When you butt fuck away my anal virginity on Thursday, I want you to dump the biggest load of your life in there. So it’s no fucky, no sucky, no jacking off until you cum in my ass in approximately 80 hours from now.”

“Oh, that is a bummer.” Pausing to think of some negotiation possibilities she interrupted my thoughts.

“And this is the smallest of three plugs so you will be getting me off every day when I return from dropping off the girls except on the day we leave. After each time you put in a bigger plug, get the picture.”

“I do but now this is like some kind of multi day edging for me…”

She interrupted again, “Which will have you well-stocked for what I expect Thursday.”

“So what are the rules for our morning ritual?”

“Other than fucking me with your cock, you can do whatever it takes. You like eating pussy, you like licking ass, you can use this plug on my pussy but once it goes in my ass it stays for the day and I will remove it later.”

“Are you afraid somebody may show up?”

She reached for her Apple showing me the location of Jason using find my iPhone and said, “The doors are locked, the girls are at school and Jason is currently at least 28 minutes away so I suggest you eat me first before eating breakfast.”

She was already sliding down her leggings and sat on the breakfast bar chair hiking up one leg giving me perfect access to her goodies. I took my time again not breaking eye contact and regularly commenting on how good she tasted.

“Josh, you have to be a world-class pussy eater because damn, you get me going so fast. I should whore you out to some of my friends.”

I guess the idea of that pushed her over the edge. I was using the plug on her pussy while licking her clit to have it good and lubed up for the ass placement.

“Ok bottoms up sis.”

As she was repositioning herself bending over the chair she said, “There’s lube in my purse to help us both.”

“I think between your girl cum all over this plug and ample saliva this little one will be painless.”

“But there’s no saliva…”

And before she could finish my tongue was licking her ass while I rubbed her clit to another orgasm. Her knees buckled and it was not for her upper body strength to hold her up I would have had to catch her.

“Wow, that was a pleasant surprise.” She said, panting, “Now don’t you think we should use the lube?”

“I replaced my tongue with the plug while you were cumming, it’s already in there.”

She stood up and said, “Well how about that?” Feeling it and reaching around to confirm.

“I think I’m going to like our morning routine, how about you?”

“I will never complain about going down on my sexy sister but damn, Thursday is a long way away.

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