Questions 1

Questions, Ch. 1
by Boxfan

I broke up with my last girlfriend almost a year ago. She was bitch. I was an asshole.

But I was happy being single. I have a decent little ranch-style house, a good job and very few responsibilities. Mom was pissed about the break up; she wanted grandchildren. My sister was married, kid free.

I was sitting at home looking at porn when the doorbell rang. Begrudgingly, I threw on a pair of shorts and answered the door.

“I need a place to stay,” my sister said through tears.

“Is everything okay?” I asked holding the door open so she could come in.

My sister Lynn informed me her marriage was ending. Shock washed across my face. Lynn seemed to have a perfect marriage. The short version was after being together for eight years, married five, they wanted different things. She was a homebody and he was the outdoor type. After a long talk they decided to divorce. The plan was simple, if she could stay with me or Mom he would keep the apartment. If she couldn’t, he would find a place of his own.

Since I could never say no to my big sister, I said she could stay as long as she wanted.

Lynn is seven years older than me, 33, and was the only person I trusted, other than Mom and Dad. I set her up in a spare bedroom and we spent the night talking. We fell asleep on the couch side by side. In the morning I decided she was staying with me for at least a year to save some money. She wanted to argue but finally relented. We spent the day getting all her stuff and bringing to my place.

Helping Lynn unpack was an education for me. Other than clothes for work, she only had a few pairs of jeans, a couple pairs of shorts, and a bunch of t-shirts. Nothing very girly at all. Except. Except the rather large collection of underwear. It was all very sexy and some would leave little to the imagination.

“I like nice underthings,” was all she said. Not a hint of embarrassment that her brother was helping to put it away.

I also learned of her vast, and heavy, book collection. It covered every subject from relationships to science fiction. I knew she read a lot but not that much.

Not a single DVD or CD. But lots of handwritten recipes.

The next month was us getting used to each other. I was neat, but she was almost OCD about being neat. She likes to cook, so I was glad to let her make whatever she wanted and benefit from her hard work. She would read while I played video games. Everything was going well.

One weekend I woke up horny and was in bed masturbating when we she walked in to ask about breakfast. I franticly grabbed for anything to cover myself, but she just waited. “Calm down, it’s no big deal. You finish up. French toast will be ready soon.”

Of course I didn’t finish. I walked out looking like I just got caught jacking off – oh, I did just get caught, by my sister.

“There is no way you finished that quick. And if you did I know why you’re single.”

That was uncomfortable, at least for me. Lynn was acting as if nothing had happened.

Once breakfast was done, we went about cleaning up the kitchen and the rest of the house. After a couple hours I almost forgot about being caught cock in hand.

When Lynn said she was going to do some laundry I didn’t think anything of it. One thing that I loved about my house was having a dedicated laundry room, which was located off the master suite. So when I heard the washing machine start I instinctively looked up. That is when the uncomfortable started again. Lynn walked out to the living room wearing a tight tank top and lacy baby blue panties. After a moment of shock I turned and looked away.

Again she was acting as if nothing was strange. When I wouldn’t look at her she figured out I wasn’t sure where to look.

“I don’t have a lot of clothes, so when I do laundry I have to wear what is clean,” she explained.

That made sense.

“I’m the one half naked and should be more embarrassed than you,” she continued.

Again, that made sense.

So after a few minutes I mostly ignored the fact my sister was showing a lot more than I was expecting. If she wasn’t my sister I would have been going nuts. The tank top clung to her B-cup breasts, and the panties were lacy enough and sheer enough that I knew she shaved her pubic hair. Her soon to be ex-husband was a moron, she looked incredible.

I knew she looked incredible because my hot chick barometer was getting very stiff in my shorts.

I figured I would play my video game, Lynn would do what Lynns do and that would end my problem. No such luck. Lynn sat by be and watched as I killed zombies. When a zombie popped around a corner, I felt a wonderful set of B-cups press against my side. Then I shot the zombie. The boobs removed themselves from me, but the owner was glad to see the offending zombie splat against the wall, and she bounced up and down with glee. Not wanting to be left out the excitement the boobs bounced as well. This was a problem for me. My mind knows the owner of the boobs is my sister. My dick knows the boobs are prefect and the owner is hot.

I killed zombies for another hour before Lynn went to fold her clothes. Then I made a break for my room hoping to avoid any questions while I had a hard-on. I didn’t think she would believe killing video game zombies would cause an erection.

Safely in my room, I tried to compose myself. After thoughts of creepy clowns and dead puppies had the desired effect, I walked back to the living room. I would like to say I was able to get used to Lynn walking around almost naked, but I didn’t.

Deciding to get take out for dinner, I left in search of food and a non-hard-on producing environment.

With pizza in hand and soft dick in pants I returned home. I was able to make it through dinner hard-on free. I was relived to finish before sis and was back on the hunt for roaming zombies before I was forced to watch my hot as hell sister prance around the kitchen cleaning up.

When she asked if she could use my computer, I was more than happy to be spared from avoiding looking at her. Never in my life was I scared of a beautiful half-naked woman. But this was my sister, and it had been a few months since I had done anything sexual other than jerk off.

A few minutes later. Lynn called for me in my computer room. Walking into the computer room, I realized I didn’t close out my last window. On the screen was a paused video of a slim girl in a school girl outfit with her mouth around a cock.

“I, uh, I mean , uh,” I stammered.

“Shut up. I know you jerk off. All I wanted to tell you was you should invest in a website that gives full videos. I can give you my password to one site if you want,” she said calmly.

I stood dumbfounded. No words came into my mind to say. So I stood there like an idiot.

Unfazed Lynn stood up and walked out of the room.

I stayed in the room for a little while trying to wrap my head around what just happened. My sister informed me she knows I masturbate, made suggestions on what I masturbate to, and then offered me access to a porn website she pays for. This also meant she liked porn and was more than likely masturbating to said porn.

I hid in my room for the rest of the night. I was a grown man, in my home, hiding from my sister. This was a low point.

The next day I avoided Lynn like a midget avoids a basketball court. This worked until dinner time. I was planning to sneak out of the house and find a place to eat, but as the final stages were being put into place the smell of perfection wafted into my room. That wasn’t, yes it was, lasagna, homemade lasagna. Plans were abandoned, self-esteem was forgotten, and I sheepishly walked into the kitchen.

“Oh my, he lives,” Lynn said pulling the holy grail of food from the oven.

I acted like I didn’t know what she was talking about, and while I thought my performance was Emmy worthy (probably not good enough for an Oscar) I got the impression she was not fooled.

Since she was actually wearing a complete set of clothes, I was slightly less distracted…slightly.

I set the table as she finished with the food.

I ate looking at my plate and nothing else. It wasn’t long before Lynn started talking to me. My side of the conversation was mostly grunts and odd sounds. The only full sentence I offered was a rave review about her culinary skills.

I had made it through the meal. I was proud, no conversation about my porn, no hard-on and not even eye contact.

I cleaned the kitchen with the speed and intensity of, well something that is intense and concentrates well. Dishes in the dishwasher, food products in their proper place, the time to flee had arrived. I had made a flanking maneuver that would have made any general proud, but before I could escape the enemy used a ruse to thwart me. “Could you help me?”

I was trapped. How could I retreat? Patton would have stayed the course. I could stay the course, too. I would use my now refined acting skills (I was Emmy worthy after all) to claim I hadn’t heard her. It was going to work, until. Until the sibling atomic bomb was dropped.”Please.”

The only phrase used less by brothers and sister around the world is “I’m sorry,” and that is so rare I had no concern of hearing it.

Deflated I abandoned my retreat and was now walking unarmed toward the opposing force. Patton would be ashamed.

I had been duped. Lynn wasn’t in the kitchen, she was in her bathroom, still fully clothed, thank you, Jesus. The shower was running and she had a look of concern on her face.

“No hot water,” she muttered.

Of course the sink had hot water, but not the shower. That left one very unhappy thought for me, she had to use my shower.

Normally a hot chick in my shower is a blessing. But the hot chick was my sister.

Confession time: Lynn is hot, like holy fuck, do I need to sell my soul to fuck her hot. The reason I lived in fear is because that much hotness running around half-naked was causing trouble, nay, disturbing thoughts for me. I wanted my sister, sick bastard.

So her in my shower caused me to almost panic. Fucking plumber better be here first thing in the morning, I did care about cost at that point.

So I went to the living room to watch TV while she showered, naked, in my room, rubbing soap over her pert tits – oh, shit, I gave myself a hard-on. Did she shampoo and condition her pubic hair? Did she have pubic hair? Damnit, now there was pre-cum. Dead puppies, dead puppies. Didn’t work, made me think of puppies, puppies are slang for tits, my sister had tits, her tits were perfect, at least I assumed they were perfect.

I thought it would be a simple process. Take her shower stuff into my room, get clean, dress in the bathroom, continue life.

Nope. She walked from her room, through the living to my room in a towel. No clothes, just a bottle of shampoo and conditioner. What was she going to change into after the shower? Panic again.

I heard the shower start and tried to focus on the show. I was finally into the show when the shower stopped. A few minutes later Lynn walked slowly, very slowly out of my room, in a towel, glistening with wet hair, “I feel better, thanks,” she said stopping to talk.

I was never a bad person, sure I could have been a better person at times, but I could only assume I at some point I was a major douche to earn the torture of my almost naked sister stopping to talk to me.

When she walked off, I could only say a prayer of thanks.

You would have thought for $90 an hour a plumber would be more than willing to work on a Saturday. I thought that would be a true statement. It wasn’t. This cocksucker (no offense to anyone that actually sucks cock) told me as a non-urgent repair the soonest he could be at the house was five days later. Non-urgent? Asshole.

Over the weekend I was able to maintain my composure through sheer will power, lots of video games, and a jar of Vaseline. Monday was easy due to work and Lynn going to a movie.

Tuesday it all came undone, horribly undone.

I walked into the house after work and dropped my stuff off in the computer room. Then I saw the browser was open and it was the porn I had been looking at that morning. The title “Selling Cookies” was above a freeze frame of a blond girl in pig tails bent over a table with a cock in her pussy. That’s when I remembered Lynn didn’t go to work in the morning. She had the day off. She probably saw all sorts of weird porn on my computer. In all fairness, I was the dumbass that had eight windows of porn brought up.

I hung my head and slinked to my room. Then I realized I hadn’t seen Lynn. I was in a full sprint to the computer room, maybe she had spent the day shopping, or working at a soup kitchen, or something, anything but getting on my computer.

No such luck, there was a note stuck to the computer monitor.

“I just wanted to thank you for everything you’ve done for me. I know I have intruded on your life and you’ve never complained. I’ve noticed some unexpected reactions to me and I’d be lying if I said it hasn’t been good for my ego. Anyway I’m going to try to make it up to you.

P.S. Sometimes it’s better to just go with the flow and not ask questions.”

I was completely confused, which isn’t really uncommon, because the note was typed out with no names. I slumped into the chair and was using more gray matter than usual to figure out what the note meant when the doorbell rang.

When I answer the door my confusion doubled, then tripled. Lynn was dressed in a fake scout uniform, very similar to the one still on my computer, shit I forgot to close the window. Her hair was in pigtails and she was holding a box of what appeared to be cookies.

“Hi, mister, would you like to buy some cookies?” she asked in a nasally high kid’s voice.

Before I could answer she walked past me.

Still using the strange voice she continued, “This is the last box I need to sell and I win a prize.”

I started to say something when she cut me off, “They only cost five dollars and taste really good.” She turned so her back was to me. “Oops, looks like my shoe is untied,” she said before bending over. Then I saw it. Her well-groomed pussy was on display as the too short faux-uniform crept up over her hips. Taking a very long time to tie her shoes, her sales pitch continued.

“I’d do almost anything to get the prize.” She wiggled her ass and I that caused an erection I wasn’t expecting. “Gee, mister, I forgot to put my undies on and my naughty parts are cold. Could you help me warm them up? I don’t wanna catch a cold.”

Dropping to my knees, I kissed her bare pussy and inhaled her sweet scent. I was in a trance as I licked her exposed cunt. In a very awkward shift, I managed to get my tongue to her clit while I used two fingers to work her opening. A moan escaped her mouth as she shuttered to an orgasm faster than I thought possible.

“Thanks, mister,” she cooed as she moved to the sofa and leaned over the side.

“You can stick your thing in it if you want. I use my fingers and a hair brush handle sometimes when I get all tingly down there.”

Despite the fact I knew it was wrong, I unzipped my pants and slid myself into the “scout” bent over the sofa arm.

I felt her warmth and wetness envelope my cock as I slowly pushed deeper into her. Any confusion or concerns I had disappeared when she used some unknown thing where her pussy actually drew me into her further. My hands caressed her hips and ass as I violated my sister/scout. The smooth softness of her skin was like heaven.

“Hey, mister, I gotta get home for dinner,” she grunted as I slid out.

“Can you go fast?” she asked, pushing herself against me.

Without thinking, I began to fuck her as hard as I could. She began to moan and grunt her approval as I slammed into her repeatedly.

As I became aware I was about to come, I felt her hand on my balls and she gave a slight tug. That sent me over the edge and I filled her with my seed.

I stumbled backwards as Lynn stood and straightened her outfit. “Five dollars for the cookies.”

Reaching in my wallet, the smallest bill I had was a twenty. I handed it to her.

“I don’t have any change,” she said in a hurt tone.

“The rest is a donation,” I muttered.

She skipped out of the house as I stood, dick sticking out of my pants, dripping come on myself.

I went to my room to change when I heard the door open. Leaning around the corner I saw Lynn wearing a sundress and no pigtails.

“Hey, I found an extra twenty in my purse and decided to get us pizza,” she said putting the box of cheesy delight on the counter.

“Where’d you get cookies,” she asked smiling and looking at the box.

“Some scout was selling them,” was the answer I offered.

She nodded and began getting plates out, when she turned I saw a few drops of my come running down her leg.

~ ~ ~ ~ ~ ~ ~ ~ ~ ~

The day after the “Cookie Incident,” I tried to talk to Lynn about what had happened, but she simply said I was probably dreaming about it after jerking off to a video that was way too similar. Maybe it was a dream and I had lost my mind. That made sense. After all I was lusting after my sister, and that was crazy. So I decided I was going crazy, dreaming about fucking my sister. I’d need pills, and lots of them.

To add to my crazy, I convinced myself that the panties my sister wore around the house were getting skimpier. I was sure I could see more ass. And the fronts of her panties seemed to be a little more see through. Crazy wasn’t so bad, I thought.

The next few days went by with no new episodes of my descent into sexual madness. Then on Friday I relapsed. After work I planned to nerd out and destroy an entire city of zombies. Since Lynn said she had plans, I figured it was going to be pretty tame, or lame, depending on your feelings about video games.

Arriving home I didn’t see Lynn’s car and assumed she left straight from work to wherever she had plans. I threw on my trusty gaming gear, shorts and my lucky X-Men shirt, and settled onto the sofa after making the necessary snack provisions.

I had just cleared an entire street of flesh-eating undead douche bags when my phone informed me of a new text. My circle of friends is pretty limited, and most of them are either married or the type that read “The Joy of Sex,” but didn’t know the joy of sex because their parents didn’t let them have friends over past 10:00 pm. That narrowed the possibilities to either work (unlikely, they hate my overtime rate) or family.

Mom didn’t text much, Dad had heard of text messages, but was wholly of the opinion that it was for people “too damned lazy to pick up the fucking phone,” that meant it was likely Lynn.

“Quit jacking off long enough to turn the oven onto 350 in 45 minutes,” the text read.

This meant two things: first, Lynn assumed I wasn’t spending time with a lady friend; second, she was making dinner. The first was sadly true, the second was a gift from God.

I set the timer on my phone for 45 minutes and mentally prepared myself for the onslaught of zombies I was about to face. Then the doorbell rang. I was I supposed to save the world from the zombie plague with so many interruptions?

I flung the door open to see my sister in a very professional looking skirt and blouse outfit and a wig. What?

“Excuse me, sir, I’m from Sexual Innovations, a company dedicated to providing quality sexual wellness products to the market place. I am conducting research and was wondering if you have a few minutes to answer some questions,” she said while adjusting her glasses that she didn’t need.

I welcomed “Ms. Loose” into the house and offered her a seat and drink. Once we were settled, she began asking questions.

“Was you last sexual encounter in the last week, month, or year?”

“Last week.”

“Was this sexual encounter pleasurable?”

“Very much so.”

“Was it with a spouse, girlfriend, boyfriend, female acquaintance, or male acquaintance?”

“Female acquaintance.”

“Did you perform oral sex on her?”

“Yes.”

“Did she perform oral sex on you?”

“No. I felt slightly used.”

“Did you penetrate her vaginally, anally, both or none?”

“In the V.”

“Had you been offered to enter her anally, would you have?”

“Yes. Hell, yes. She had a great ass.”

“Assuming you achieved orgasm, where did you ejaculate?”

“In her oh-so-sweet pussy.” Oh shit, I didn’t think about birth control. How retarded was I?

“At any point during your coupling did you want your partner to utilize a sexual device?”

“Maybe. Watching her fuck herself with a dildo would have been cool.”

“Would you have wanted this sexual device to be larger, smaller or comparable to the size of your erection?”

“Uhh, smaller, I guess. I don’t want her to stretch her puss out to the point I’m throwing a hotdog down a hallway.”

“Thank you for your time. I would like to apologize for the woman you had sexual relations with recently. She should have reciprocated your oral favors. I’ll assume she was younger since this is a common practice. To thank you for your time and to make up for the mistake of a fellow woman I would like to perform fellatio on you with no reciprocation,” she said as she reached over and began to pull the waist of my basketball shorts down. I tried to argue but my penis was very adamant that I allow she was right.

“Ms Loose” adjusted my position before getting on her knees in front of me. Looking directly into my eyes she covered my cock with her mouth. Her tongue swirled around the head of my dick as her right hand stroked my shaft and her left hand fondled my balls. I was transfixed as my sister gave me a blowjob that was better than any I had had before. She continued swirling her tongue around my cock and making eye contact. I couldn’t take my eyes off hers. Then she winked, broke eye contact and took my whole cock in her mouth.

Lynn began sucking my cock with a skill and enthusiasm I had never experienced before. She seemed to enjoy the blowjob almost as much as me, almost. Her left hand was caressing my balls as she pumped her head up and down on me vigorously. I felt a tingle and knew I was going to come and uttered something about it. When I tried to warn my sister of my impending orgasm she again took my entire cock in her mouth and kept it there. The hand on my balls left as I felt her tongue tickling my cock.

Just as I was about to come I felt a finger push against my asshole. I was shocked and about to say something when the finger actually went inside my ass. This forced me to push my hips forward, causing my cock to press harder into her warm mouth, then I came. I came harder than I had ever come before. It felt as if the jets of come would never stop. Lynn, at no point removed her talented mouth from me as I emptied my seed. With a final swallow she slipped her mouth off my cock and stood.

Straightening her skirt she thanked me for my time and walked out the door.

Moments later, I got a text. “Don’t forget the oven.”

After the oven was on and I was reliving what had just happened, I got another text, this one from a number I didn’t know. “Remember, don’t ask questions.”

After another round of zombie slaughtering, Lynn walked in the house looking nothing like she had earlier. “No wonder you don’t have a girlfriend, more video games.”

We ate dinner and talked about nothing and had a great meal. I really did love my sister, but what was going on?

When she walked past me, only in a towel, she busted me looking at her. “Perv,” she said.

Then, in a moment of clarity, it all made sense. Lynn didn’t want to admit to incest, but if she was role playing it wasn’t her fucking her brother. It was someone else fucking me. And she got to act in ways that she normally wouldn’t.

So, I resolved to never ask questions.

~ ~ ~ ~ ~ ~ ~ ~ ~ ~

Chapter 2 >>

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7 thoughts on “Questions 1

  1. I loved your story and want more of the same. He should start jacking off in front of sis and also do some roll play disguised as someone else and fuck her in the ass like she hinted at and make it an all night affair.

  2. This is one if my favorite stories on this site. I’ve wanked off over it many times and I think that the picture asociated with the story is perfect! The thought of fucking my big sister, from behind, while she’s bent over the back of the livingroom couch is such a turn on!

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