Blackmailing My Sister - Cover

Blackmailing My Sister

Copyright© 2011 by Connor

Chapter 1

Romantic Sex Story: Chapter 1 - The story of Kyle who comes up with a scheme to blackmail his sister Karen. An event that sets off a chain that changes them both.

Caution: This Romantic Sex Story contains strong sexual content, including mt/ft   Consensual   Romantic   Blackmail   Heterosexual   Incest   Brother   Sister   First   Oral Sex   Anal Sex   Petting   Voyeurism  

Growing up wasn't easy with an older sister. Karen was 2 years older then I am and loved to torment me. Pretty typical I guess. I was the nerdy little brother. Where Karen was blessed with the superior looks in the family, I was blessed with the intellect. Not that she was stupid, things came harder for her and she didn't have the self-discipline to study harder.

Karen was also the popular one. Typical cheerleader type at our school, which also meant she could be a bitch at times. She was outgoing and liked to be the center of attention. I was quieter and more socially awkward. Karen especially delighted in that at times I could be easily embarrassed.

At school, we had little interaction. It was at home where she tended to set me up for her own personal amusement. She loved to make me blush. Every once in a while though, I would catch a glimpse of her that told me she wasn't quite the bad girl she liked to portray, by things she would do or say.

She had gotten herself into trouble with our parents on more than one occasion, usually in connection with her friends. Truth be told, Karen was a follower, not a leader.

By the time I was 13 a favorite game Karen loved to play was to get me aroused and flustered. She would prance around me in a T-shirt and panties, or a skimpy nightie, or a towel, and do things to get me sexually excited, then lower the hammer on me by making a fuss about it. She'd tell me what a pervert I was and threaten to bust me out to our parents.

She'd get a good laugh out of it when I'd blush furiously, and stammer about, trying to deny any improper thoughts. Problem was, often my thoughts were on the improper side. This made the feeling of guilt in me all the more stronger. More than once she conned me into doing her chores by telling me that it would keep her from spilling the beans. Of course, if I hadn't felt guilty about what I was feeling, her tactic wouldn't have been nearly as effective.

More than once I was lured into the bathroom or Karen's bedroom only to fall prey to one of her traps. I learned to become very wary around her. I'd be lying though if I said I never masturbated to images of my sister.

She'd call me in for one reason or another and when I'd enter I'd catch the briefest glimpse of her half dressed which would illicit a shriek from her. More than once she came into my room while I was working at my computer, wearing something skimpy and sexy. She'd stand behind me and press her breasts against me, brush her hand against my skin. I'd feel her warm breath against my neck and just like that, the trap was sprung.

Still, there were a couple of occasions when I actually got a view of a breast, or ass cheek. Never a very long or very good look. I got the feeling when that happened that she was taking pity on me. What I didn't know and wouldn't find out until later was that aside from tormenting me, Karen got a bit of a thrill from being naughty in front of me and from the effect it had on me.

The damn fact was that Karen was very sexy. She had such a tight, hard body, nice sized boobs, and an ass that was criminal. She was toned, athletic, and tanned. She had long brown hair that went below her waist, almost to her ass and was silky and soft. One of my punishments sometimes was to brush it out for her. In actuality, I liked brushing it for her and I had the feeling she enjoyed it too. She also had these big, brown doe eyes that made guys melt.

Me, I was tall enough, I had hit 6'1" after my growth spurt but I was on the skinny side and I wasn't overly coordinated. I had the same color hair and eyes as Karen but on me they seemed more plain. Thankfully, the other thing we had in common was that neither of us suffered much from acne. I wasn't as tanned as Karen, mainly because I didn't use tanning beds during the winter like she did, but I did swim during the summer and both of us were a little dark skinned naturally, so I did have some tan.

Another thing that I had inherited from our dad besides my height was that by the time I was 16 I developed a bit of a hairy chest. It was at this age when the tables turned and I found Karen at my mercy. It was her last year of high school and she would be graduating soon, when providence fell into my lap. Something called senior prank day.

For Karen, senior prank day became horribly out of control. Other groups of seniors pulled off pranks that while funny, were pretty harmless. Her group took it up a notch. A few notches thanks to alcohol and that a couple of the guys in her group who were assholes.

What started off as some graffiti painting on the school, bad enough, turned into vandalism. Windows were broken and property was damaged. They were smart enough, or lucky enough to stay off surveillance cameras. I'm going for lucky. Police were involved, kids were interviewed, but nothing concrete came out. Too be sure, the school had l list of people they suspected, but it looked like the perpetrators were going to stay in the clear. Until I was cleaning stuff in the garage that is.

That's when I came across some things in a bag tucked behind some boxes. In this bag were a few empty spray paint cans, a shirt with paint on it, and lo and behold, a memory card. I downloaded the card onto my computer and what did I see, my sister and friends committing the fore mentioned crimes!

I knew I had her right where I wanted her. My sister wasn't the kind to come up with this herself, most likely it was another case of going along with the group in order to save face with her friends. I had been suspicious anyway, knowing her crowd and also by the way she had been acting.

Now I had to decide on what payment I would extract for my continued silence. I knew if this got out she would be in a level of trouble like she had never been in before. Truth be told, I most likely wouldn't have ratted her out. Her friends in a heart beat, but that would have meant her also. She didn't know that though. I knew I was going to have to play this good.

That night it came to me. My plan was more devious than I had ever been. As I thought about all the times she tormented and teased me, it came to me. The cost for keeping quiet was going to be for her to pose for me and my digital camera. She thought I was perverted before, she hadn't seen anything yet.

The next evening after dinner it was my turn to call her into my room and spring the trap. Karen came into my room, much less cocky than was her norm. It almost took the wind out of my sails.

"What do you want," Karen asked.

"I wanted to show you something," I answered.

"What," Karen asked with a sigh.

It was then I pulled up the pictures on my computer. The expression on her face was priceless.

"Where did you get those," She stammered?

"You didn't hide things very well," I told her.

"Who else has seen these"?

"No one yet".

"You're not going to tell anyone are you"?

"That's up to you dear sister," I replied smugly.

"Do you know how much trouble I'd get into,"? She pleaded.

"Yeah, I do".

"You can't tell anyone. It wasn't my idea, I didn't know all that was going to happen. Please, don't tell anyone Kyle," Karen practically begged.

"Like I said, that's going to be up to you. Do what I want and your secret stays safe".

"And what is it going to cost me," She asked a bit fearfully.

I took a deep breath and told my sister what it was going to cost her, everything I wanted from her. At first she just sat there and just stared at me.

"You want me to pose for your pictures," She asked disbelieving.

"Yes. Friday night when mom and dad go to their dinner party you're going to pick out a couple three sexy outfits and model for me. Then you'll strip for me, naked, completely naked, and when I have the pics I want, you're in the clear," I stated firmly.

"You've got to be kidding Kyle. I'm not doing that and I don't think you'll really show those to anyone," Karen said, calling my bluff.

"Up to you, I can print these off right now. A copy for the folks, some for the school, maybe even sell them to the news, who knows," I said, shoring up my courage.

"Jesus, you really are a pervert. I can't believe you want to take naked pictures of your own sister".

I shrugged my shoulders, "Think of it as Karma, for all those times you teased me. No teasing this time".

"There has to be something else. Do your chores, be at your beck and call, something," She pleaded.

"That's the deal, it's non negotiable," I said, holding my ground.

Karen sat there silent for a few minutes. I knew she was weighing her options and gauging just how much trouble she would get into if this got out. I could see her hands were trembling a bit.

"If I agree and I'm not saying I will, what are you going to do with the pics,"? Karen asked.

"These go away, the ones I take stay hidden," I answered.

"No web sites or You Tube or anything"?

"Nope".

"Why do you want them then," Karen asked suspiciously?

"Like I said, Karma, simply pay back," I told her.

"You're probably going to beat off every night to them, pervert," Karen said angrily.

"You can tell me tomorrow, deal or no deal," I said, refusing to be baited.

"You're serious," She asked.

"Very. Good night sis," I said, turning back to my computer.

Karen got up and left my room. I let out a heavy breath after my door shut. My hands were shaking and I felt almost dizzy. This was the first time I had taken control of a situation with my sister. I felt almost liberated. I also didn't realize just how momentous this was to become for us both.

The next morning at breakfast Karen quickly walked behind me as she was heading out the door for school.

"Deal," She whispered as she passed behind me.

Nothing more was said. The next couple of days Karen avoided me at all costs. She didn't talk to me at all. When Friday came I was a bundle of nerves. I was still half convinced that Karen would bail out on the deal. I couldn't wait for school to get out.

At home, I quickly went to my room and waited, killing time on my computer. Around 5 o'clock my dad poked his head in my room to tell me that he and my mom were leaving and that there was food in the refrigerator if I got hungry. I heard him repeat the speech to my sister next door. My stomach was in knots. A few minutes later I heard my parents leave. About 15 minutes later Karen poked her head into my room.

"Well, let's get this over with," She said to me.

My head was swimming with anticipation. I still couldn't believe this was actually going to happen.

"What is it you're wanting me to wear exactly," Karen asked with a note of resignation.

"Start with a dress, that nice black one, and some sexy underwear. Grab a couple of other outfits, like that pink babydoll you have, maybe something else too," I said, "Then bring them back here".

Karen left my doorway and went back to her room. a few minutes later she was back in my doorway wearing her black dress and heels. She looked stunning.

"You're really going to make me do this,"?

I nodded my head, "Yep".

"OK, let's get this straight. We do this and no one knows about prank night and no one sees these pictures".

"That's the deal," I replied.

"In here," Karen asked?

"No, in the den. We'll use the fireplace as back drop".

I walked out with my camera in hand, Karen followed behind me. In the den I turned on the gas fireplace. It wasn't cold but I was trying to be artistic.

"In front of the fireplace," Karen asked?

"Yes, face me," I directed.

I began snapping off shots as I directed my sister. After a couple of shots I had her slowly turn around while I kept taking pictures.

"Now show a little more leg," I continued.

Then I had her slide the straps of her dress off her shoulders. Next I had her let it slide down just enough to show her bra. She was wearing a pretty black one which thrilled me. Then I had her take her dress all the way off. With a little hesitation, she did as I asked. I was getting some great shots.

"Not too fast," I told her.

Karen was standing in front of me wearing just her black bra, black panties and her heels. I had never seen anything so sexy or more beautiful. I had her turn around again so I could get some shots of her back side.

Next I had her slip her bra off, again telling her not to go too quickly. Oh, those lovely breasts. She tried to keep herself partially covered with her arms, but I wasn't about to let that happen. I was sporting a full woody by now, but I didn't care. Her tan line made her hard little nipples really stand out. I took a few more pictures in different poses.

"OK, next outfit," I said.

Karen picked her bra and dress up off the floor and headed out to change. When she returned she was wearing a white denim mini skirt, and a white spaghetti strap shirt, no bra. She still had her heels on.

"Now what," She asked?

"This time, sit down on the rug," I answered.

Karen sat down and looked up at me. First I had her sit cross legged and got down to her level. I could see that she had changed into white panties. I had her pull her skirt up her smooth thighs until her panties were showing. Next I had her slowly pull her shirt off over her head.

It almost seemed to me that she had relaxed some and was even mugging it up for the camera. She arched her back and stretched her arms high as she pulled her shirt off. I wanted to touch her breasts so badly.

I had her give me different expressions as I took pictures. A pouty look, a look of surprise, even a sexy look. She quietly complied with all of my requests.

Next I told her to lay down on her stomach. Under my direction, she pulled her skirt up around her waist. My breath caught in my throat when I saw she was wearing a pair of thong panties. Damn that ass was glorious! I was afraid I might blow my wad in my jeans right then. I took some pictures in various laying down positions. Reluctantly I had her go change into what would be the last outfit.

Karen came back down in her pink babydoll nightie. It was both sexy and girlie. again we took some pictures standing and sitting. Then more pictures topless. Finally I directed her to slide off the panties. These would be the first pictures where she was fully nude. Karen took a deep breath, then slid her panties off.

My sister now stood before me completely naked. I found her tan lines to be very erotic. I also thrilled at the triangle patch of dark hair above her pussy. I had her pose with her hair covering her breasts and her hands hiding her pussy. Next I had her stretch her hands above her head so that I could see everything.

After a few pictures in that pose I directed her to turn around. A couple more pictures, then to her chagrin, I told her to bend over. The site was more lovely than I had imagined.

I had her sit down again cross legged. I thought she would balk when I had her sit leaning back with her legs spread and knees bent. I directed her to reach down between her legs and spread her labia. Karen blushed hard but slid her hands down and did as I had said. Her lovely pussy was open wide for me too see. It was all I could do not to throw her back and shove my hard cock into her beckoning hole. It was then that I realized that not only was my sister a follower, she was a subservient. She was getting off on being told what to do.

Then laying back down on her stomach, I finally I finished by having her get on all fours. I tested my theory by telling her to reach behind her and spread her pussy open again. Karen complied without a word. Reluctantly I wrapped up our photo shoot.

"All right, done," I informed her.

"That's it," She asked?

"Your end of the deal is done."

Karen picked her clothes up and headed for her room. I was looking over some of the shots I had taken when it dawned on me that she had wore those white thong panties of her own accord. I had told her to pick out sexy clothes and obviously she had complied.

As I passed by her room, I heard a soft sound coming from inside. I pushed open the door, afraid she was actually crying. That would have killed me. After all, I didn't hate my sister, in my own way I really did love her.

What I saw though was my sister laying on her bed naked, fingers in her pussy. I was taken aback, Karen was masturbating.

"Get out," Karen shrieked when she saw me open her door!

Instead, emboldened by the evenings events, I stepped into her room, "No, I want to talk".

"Get out," She yelled again, pulling a sheet up over her body!

"It doesn't bother me," I said calmly, "I don't care".

"Maybe it bothers me"!

"Listen, I want to talk," I said, sitting down on the edge of her bed.

"Now"?

"Yes, now. Tell me what happened prank night".

"Like I said, I didn't know all that was going to happen. I haven't even talked to them since".

"I believe you, so why did you go along with it," I asked?

"I don't know," She answered.

"Is being part of that clique really that important to you"?

"I thought so. I was wrong," Karen answered softly?

"Why in the name of hell did you have that stuff hidden in the garage," I asked?

"Jeff told me to get rid of it and I was scared," my sister answered honestly.

"I wouldn't have ratted you out," I said, looking at her.

"I really didn't think you would," Karen said.

"Then why did you go through with our deal"?

"Better safe than sorry and to be honest, I figured I really did owe you for some of the things I've done to you".

I knew then that Karen didn't realize she was subservient, at least to some degree, but giving in to it tonight had really turned her on.

"Why have you teased me like that for the last three years," I asked curious?

"Well, it was fun, felt naughty. It wasn't out of spite, I actually do love you little brother," Karen said, propping herself up on her side to look at me.

"Tell me honestly, you got off on what we did tonight, Didn't you"?

"Actually, yeah, kinda, but I'll never admit that to anyone else".

"Fair enough," I replied.

"Does that sound weird," Karen asked.

"Not to me, good night sis".

"Good night".

With that I left her room and went to mine. I downloaded the pictures of her onto my computer and studied them for the next half hour. Damn she was gorgeous.

The next day I was playing a game on my computer when Karen came in. She sat down next to me.

"So how long did you stare at my pictures last night," my sister asked?

"About 30 minutes," I answered truthfully.

"You really like them, huh"?

"Sure, what's not to like," I stated.

"Can I see them"?

"Sure," I answered a little surprised.

I brought the pics up and watched as Karen looked them over. I wasn't sure why she wanted to see them but far be it from me to deny her seeing her own pics.

"You did a good job, though my ass looks fat," She finally said

I let out a laugh, "No it doesn't," I assured her.

"Was that the first time you've seen a girl nude," Karen asked?

I wasn't sure what she was getting at but she was being amicable so I decided to answer honestly.

"Yes, it was".

"I thought maybe. Especially with the serious woody you had," my sister said.

I looked at her closely to see if she was mocking me. As far as I could tell, she wasn't.

"I couldn't help that. It's biological, sister or not. You're hot".

"Well, I'll take that as a compliment. So why haven't you dated"?

"In case you haven't noticed, girls aren't lining up to go out with me".

"What are you talking about? You're a cute guy and I know several girls who would go out with you if you asked".

"Really," I asked surprised.

"Sure. Can I tell you something honestly"?

"What," I asked, kind of pleased we were talking like this?

"I've never seen a guy either," Karen admitted.

"You're telling me you're a virgin," I asked?

"Yes".

"Bullshit. I know you're on the pill," I said, thinking she was setting me up again.

"That was to help regulate my periods, not because I'm screwing anyone," Karen informed me.

"I didn't know," I replied.

I wondered how she had managed to stay a virgin being the way she was but figured the couple of guys she had gone out with were too stupid to figure it out. They were so into themselves they really didn't bother to see others or figure them out. I'm sure they didn't know she was on birth control either, so they probably feared pregnancy as well.

Karen really didn't go out on dates much, and usually it was with a group. I think down inside she knew if some guy pressed the issue, she wouldn't have been able to say no, so she avoided being in that situation.

"I've had opportunity but to be honest, I was too scared. I didn't want that kind of reputation".

"Well, none of the guys you associate with are good enough anyway," I told her.

"After what's happened lately, I'd agree," She admitted, "That's partly why I've been teasing you. I got to be bad but it was still safe. I'm sorry".

"That's OK. Mostly I didn't mind," I told her.

"I noticed," She said with a giggle.

"OK, I got a boner looking at my sister. Laugh it up, then move on".

"I'm not laughing at you. Not after you caught me doing what I was doing last night," Karen said to me softly.

"Was that because of what we did"?

"Yes".

"Did you wear those thongs just to try and get me worked up," I asked her?

"Of course. I wanted to get some fun out it too".

"I guess I deserved that," I conceded.

"Yes you did, but now I want to ask you something," Karen said a little timidly.

"Shoot".

"Do you think we could do that again"?

"Yeah, sure," I answered completely floored.

"Except I was thinking maybe this time we could take pictures of each other," Karen continued with a blush.

"You want to take pictures of me too," I asked completely taken by surprise?

"Yes, if you wouldn't mind. Naughty but safe," She said to me.

I thrilled at the prospect of seeing my sister naked again, but I was also self conscious about her seeing me naked. After all, she was hot, but I was just me. All of a sudden I figured it out. Safe meant she felt safe letting me take control and give in to her subservient side.

"OK, we can do that," I answered.

The next couple weeks went by without any opportunity for us to engage in our photo shoot. graduation came, and then school let out for the summer. Karen would be going to college in the fall but it looked like a local one and she would be living at home. I had begun to think she had forgotten all about taking pictures of each other. I was wrong, now she was waiting for me to make the move.

If this was going to happen, I needed to screw up my courage and say when and where. After our parents left for work I popped into Karen's room.

"Ready to do this," I asked?

"Sure, if you are," Karen replied.

"Let's go".

I headed back to my room, with Karen behind me. Again my stomach was full of butterflies but I was determined not to let it show. I wondered if she felt the same nervousness.

"We'll just stay in here this time," I said.

"OK, where do you want me"?

"Sit on my bed, just act casual," I told her.

I had Karen give me a variety of looks, from sexy to goofy. We actually had fun with it. Then I had Karen stand up and I showed her how to use my camera. I then let her take some pictures of me. I hammed it up for her which made us both laugh.

Taking my camera back I had her sit back on my bed. She peeled her shirt off at my direction and I snapped a few off with her in her bra. Then I had her take her shorts off. She looked so cute in her matching pink bra and panties. I took pictures of her in a variety of poses which she did without hesitation. I felt my hard on return.

Then it was time to loose the bra. Karen took it off and tossed it to the floor. She didn't pause when I told her to cup her tits and squeeze them together. Next I told her to take her panties off. I almost forgot to take pictures as I watched Karen arch her hips up off the bed to slide her panties off of them.

My cock was throbbing as I took pictures of my naked sister in a variety of sexy poses. Here she was, my own private nude model and a damn sexy one at that. I didn't see how I could ever get tired of looking at her body. Though it started out as an act of blackmail, she seemed a willing partner now.

I really didn't want this to end, but I had told her that I would let her take some of me. I guessed it was time. Fighting the unsettled feeling in my stomach, I told Karen to go ahead and take the camera, it was her turn.

Karen smiled broadly as she got up from my bed and took my camera from me. I stepped back as she turned it on me. I was a bit surprised that she didn't throw her clothes back on first but also pleased. Karen took pictures as I pulled my shirt off.

"Look at you, little brother is getting some hair on his chest," She said.

Her comment made me more self- conscious. She continued watching me on the led screen as I stripped in front of her. I was embarrassed by my erection and was unsure how she would react. To her credit, she didn't tease me at all after I was completely naked.

I allowed her to take pictures of me from all directions, first standing, then lying on my bed. After a while I started to relax. Finally she finished up and laid my camera on my computer desk. She sat down on the edge of my bed next to me.

"My first real erect penis. I've seen pictures, never the actual thing," Karen said.

I saw that she was studying my manhood like someone looking at a really interesting sculpture. Curiosity was written in her face.

"Go ahead, touch it," Popped out of my mouth before I thought about it.

Karen looked over at me, I couldn't tell what was going through her head at the moment, but I think we both realized that we would be crossing yet another line. She looked into my eyes for a couple more moments, then without a word she looked back at my raging hard on. Slowly, tentatively, her had reached out and her fingers touched my hard shaft.

I closed my eyes and sucked in my breath when I felt her soft touch on my pulsing member. Her hand shot back like it had touched a hot stove.

"I'm sorry, did that hurt," She asked?

"No, not at all," I answered.

Karen reached out and touched me again. Then she wrapped her slender finger around me and lightly squeezed. I could feel her hand trembling.

"OK. that's good," I said, afraid of what might happen.

Karen let go, then laid down on her side next to me so we were face to face.

"Well, what next," she asked.

The last thing I wanted was for her to put her clothes back on, but I had no good excuses not too.

"Well, we get dressed and put these pictures on our computers," I said.

"OK," She said, rolling off my bed.

We got dressed and then loaded the pics on my computer, then hers. I buried them so that no one else would stumble onto them if they snooped. That was if they got the passwords to begin with.

"So, how much porn do you have stashed on your computer," Karen asked?

"Oh, I have one or two things," I replied laughing.

"Can you show me"?

"Sure, if you like".

We headed back to my computer and I brought up my collection of pictures. Somehow they didn't excite me as they had before. All of these paled in comparison to the woman sitting next to me.

"Do guys like seeing a woman's vagina shaved," Karen asked?

"Some do, some don't. It's apples and oranges," I answered.

"Apples and oranges"?

"Both are good, just different".

"I'd be afraid to do that. "I'm sure I'd cut myself in a really bad place or I might try it," She informed me.

"Well maybe something in between. Trimmed like this girl, leave a little landing strip," I ventured.

"A landing strip, that's funny," Karen said amused.

"I'll help you," I told her, feeling a boldness I never had before.

Again Karen looked at me, "OK".

I couldn't believe my ears, "Well, mom and dad might be home before too long, how about video games for now".

"Sure," Karen said.

"I didn't think our parents would be home for a couple more hours, longer for our dad but no way I was going to risk that. We settled back and played video games until we heard our mom come in.

The next day, after our parents left for work, Karen came into my room still wearing her nightie.

"Are you ready," my sister asked?

"Yeah, lay down and I'll go get what we need," I told her.

Karen laid down on my bed and I headed for the bathroom. I came back in carrying a towel, wash cloth, scissors, my razor, shaving cream and some aloe lotion.

"Lift your butt up," I told her.

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