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Introduction:

My sister lets me blackmail her into anal sex.
My Anal Sister

I couldn’t believe that my fifteen-year-old sister Debra was giving a guy a blowjob. Not just one guy but six guys. Yes, last night my little sister Debra gave six guys blowjobs and I was watching it on DVD thanks to one of my friends. He swore that it was the original and that he hadn’t made any copies of it. He suggested that I blackmail her good with it. He was with her when she was giving the blowjobs in one of the guy’s garages. He had also gotten one before he started recording her. Apparently he was the third guy to receive a blowjob from her that evening. She had sucked twelve guy’s cocks all together to stop them from fucking her cunt. She claimed to be a virgin but was willing to pay the price they asked of her. He said that they would not have raped her but since she had offered the blowjobs they had accepted them. After he left I went into my room and hid the DVD. I then went into my sister’s bedroom to confront her with my newfound information.

Debra said, “Get out of my room creep!”

I replied, “Shut up bitch!”

Debra said, “Fuck you!”

I replied, “No! I’m going to fuck you!”

Debra said, “When pigs fly, bastard!”

I smiled, sat on her bed and said, “I’ve got the DVD of you last night giving the last six guys blowjobs!”

Debra got quiet! She got red in the face. I could tell she was thinking!

Finally Debra said, “So what!”

I replied, “I don’t think mom and dad would like it if they knew!”

Debra asked, “So what do you want?”

I replied, “Like I said! I want to fuck you!”

Debra said, “No fucking way you bastard! I’m still a virgin and I’m not on the pill! You’re not going to knock me up! Go fuck someone else! Asshole!”

I said, “Asshole! That’s a hell of a good idea!”

Debra said, “What?”

I replied, “Asshole! I’ll fuck your asshole!”

Debra said, “In your dream!”

I said, “Look Debra! I have a DVD of you sucking six guys off and it looked like you were really enjoying it too! I want to fuck you and I’ll settle for your ass!”

Debra said, “It’ll hurt!”

I smiled and said, “Probably!”

Then Debra surprised me by saying, “Okay but you’ll have to wait a week! I want time to loosen my rectum up for you! Mom has a butt plug I can get! I’ll sleep with it in me to get myself used to having something back there! Then how about next Friday night I let you butt fuck me! That way I can have two days to recover if I need it!”

I said, “Okay! Next Friday night!”

Debra said, “And if you slip it into my cunt for any reason whatsoever, even by accident, then I’ll cut that fucking thing off and shove it up your ass! Do you understand?”

I smiled and said, “Yes I understand! I can fuck your ass but not your cunt under any circumstances! Or you’ll cut my cock off and stick it up my ass!” I waited for that to sink in before I said, “I’d much rather stick it up your ass!” Then I turned and went back to my room where I made two copies of the DVD and hid them in separate places.

The next day on our way to school Debra said, “Asshole! I poked that butt plug in a few times last night. It didn’t hurt but it wasn’t great either! Besides it isn’t as big as your cock!”

I asked, “How do you know how big it is?”

Debra said, “I’ve peeked before but tonight I want a good look so I know just what I’m getting into!”

I said, “Okay! But if I show you mine…”

Debra answered, “I’ll show you mine!”

I said, “Deal! Catch you later!”

After school but before our parents got home from work I went into Debra’s bedroom and dropped my pants to show her my cock. She wanted to see it hard so she sucked it. I got real hard but then she stopped and said, “Not so fast! We made a bargain for my asshole unless you’re ready to give that up!”

I replied, “I’ll wait for your butt!”

Debra then undressed. Like she said she showed me hers! She sat back on her bed and opened her legs to show me her virgin pussy then rolled back enough to show me her asshole. She got the butt plug and K-Y Jelly and showed me how she slips it in. She said that she really needs something bigger now that she has seen my cock hard.

Then she smiled and said, “Holly has a soft silicone dildo that I can borrow! It’s perfect! Get out so I can call her!”

I pulled up my pants and took another look at my almost naked sister. I got a hard-on as I realized that in a few days I’d get to butt fuck her. No girl had ever let me do that so it would be a first for both Debra and me. By no girl had ever let me I mean all two of them. Stella let me fuck her eight times last year and Judy has me fuck her six times so far this year. Judy is a lot more willing to put out.

I smiled when Holly arrived after dinner and the two girls disappeared into Debra’s bedroom for the evening.

The next morning on our way to school Debra said, “Holly thinks I’m nuts to give you my ass!”

I just smiled and said, “A deal is a deal! Isn’t it?”

Debra said, “Yes! But…Holly had trouble getting that dildo in my ass! Then as soon as the head popped in I screamed into my pillow! Do you know how much that hurt?”

I asked, “So do you want to give me your pussy instead?”

Debra said, “Fuck no! I’ll give that hole to the right guy when the time comes! And not until! Do you understand?”

I said, “Yes! I understand!”

After school on our way home Debra had Holly with her. Holly just gave me the evil eye and the silent treatment. Once we were home the two girls disappeared into Debra’s bedroom again.

When we were called down to dinner Holly glared at me and went home to eat. After dinner Debra gave me the signal to go upstairs. She told me that Holly had gotten the dildo in her ass but that it had hurt like hell. She had left it in for one minute, two minutes, and then for a full five minutes before begging Holly to take it out. She said that she was having a hard time relaxing her sphincter muscle with that dildo in her ass but that she thought that it was getting better.

The next morning on the way to school Debra thanked me for making sure that her cock sucking orgy hadn’t gotten spread all over school. Apparently my buddy that had filmed it all had told her that I had threatened to beat up anyone of the twelve guys if they spread it around. It had been a couple of days and everything was cool. However she admitted that she loved giving blowjobs and especially the taste of their cum. She was hoping that there was a way to suck cock more often but not get a bad reputation.

I looked at her and said, “You can suck my cock two or three times a day if you like!”

Debra asked, “Instead of fucking my ass?”

I smiled and said, “No way! Your ass is my payment! I’m just offering you my cock to suck because you said that you love sucking cock!”

Debra said, “I’ll think about it and let you know after school!”

On the way home Debra brought Holly again. This time Holly actually smiled at me and said, “Hello!” What gives? Yesterday I was the biggest jerk in the world!

Debra said, “I thought it over and I’ll suck your cock before and after school and again at bedtime! But in exchange Holly gets to watch and participate after school! Deal?”

I smiled and said, “Deal! It sure beats jerking off all the time!”

At home we all went into Debra’s bedroom where I was told to get totally naked so I did. The girls stayed dressed which disappointed me. Soon I realized that Debra was teaching Holly how to give blowjobs. Mine was the very first cock that she sucked or even saw before. I was enjoying it very much. I just had to stand there with these two girls kneeling before me and taking turns sucking my cock into their warm mouths. It was so exciting that I couldn’t hold out too long as if I even wanted too. So as soon as I told Debra that I was close she had Holly put her mouth over it to get the cum first hand. It was interesting to hear about a blowjob from a girl’s viewpoint. They talked about how soft the head was, how hard the shaft was, and how to swirl their tongues around it. They talked about rubbing the soft underside with their tongues and how many girls got their tongues pierced to enhance the sensation for their boyfriends. Debra was talking about getting her tongue pierced soon. When I did start to fill Holly’s mouth with cum Debra told her to keep it in her mouth, pull back a little to make room for the rest of the cum, and to wait until I was done shooting. Then she had Holly pull off, open her mouth to show me the cum, and then swirl it around her mouth with her tongue to coat every inch of her mouth. That way she could really enjoy the full taste. After all of that then Holly was allowed to swallow just half of it. I watched Debra French kiss Holly and knew that their tongues were fighting over my cum. I was amazed at how long they did that. I was sure that my cum changed mouths every few seconds. Finally Debra backed up and told Holly to swallow it all. Debra asked her how she had liked the taste and apparently I was one of the better tasting guys. Debra mentioned one guy that had tasted so bad she damn near spit it out. She would have but the boy wouldn’t let her.

After that I was told to get dressed and get out while they put the dildo in Debra’s ass again. I left!

Holly stayed for dinner and afterwards she got another lesson in cock sucking from Debra using my cock. This time I got to sit on the edge of the bed. I reached down and played with Holly’s tits while she sucked me. Debra told Holly that all of the guys do that to her and that she just lets them. So Holly let me feel her up while she sucked. Holly was getting better and Debra let her do most of the work with just a couple of minor instructions. Then at bedtime Debra came into my bedroom. I was already in bed so she sucked me while I lay there. It was very good! I slept great that night.

Then first thing in the morning Debra was right there again before I even got to pee. I usually have a piss hard-on in the morning anyway so it was wonderful to have someone take care of it for me. I was starting to really enjoy this.

After school Debra had Holly get naked and she got naked too to comfort her. Debra had me get on the bottom and put Holly on top in a sixty-nine. This was Debra’s next step in giving blowjobs and I got to eat my first pussy. I even told Debra that it was my first time too so she gave me some instructions. Holly got so excited from me eating her that she stopped sucking me completely. Soon she came and got back to work. I sure enjoyed the fresh cum leaking out of Holly’s pussy. It was sweet and very tasty. I then realized why Debra liked sucking cock so much. I could eat pussy all day after this. Holly went home right afterwards, so Debra asked me to help her with the anal dildo part.

I got to coat it and her asshole with K-Y Jelly. Then I watched her face as I gently slipped the head into her brown pucker hole. I watched as Debra fingered her clit in front of me. She was on her back with her knees up to her chest so I had full access to her asshole and her pussy lips were spread enough for me to see the magic button that she was playing with. She said that it helped get her mind off her ass and helped her relax so that it didn’t hurt as much. I slipped it all the way in leaving just enough so that I could pull it out. Her asshole was a lot deeper than I had imagined it to be! While she fingered herself to several orgasms I slipped it in and out slowly. Debra did manage to relax. During the ten-minute session Debra told me that the girls in Greece gave all of their boyfriends anal sex so that they could still be virgins on their wedding day. Debra said that she might do the same thing! We stopped just in time for me to get dressed and get out before our parents got home.

That night at bedtime I was in bed and waiting for Debra to come in. It took a while but finally she came in. She had on a very sexy negligée. She locked my bedroom door for the first time then came over and sat on my face. I knew what she wanted and started licking her pussy. She tasted a lot better than Holly had but I assumed that Debra had taken a bath or washed up just for me. I ate her as best I could after practicing on Holly earlier. Debra leaned down to engulf my cock but she sucked real slowly since I was breaking her concentration with my tongue. I was doing a great job and I really liked this too. Eating Debra was the highlight of my day; hell it was the highlight of my life so far. Debra had a very hard time eating my cock while I was giving her so many orgasms. Finally she just collapsed on my chest and hadn’t finished my blowjob.

When she was recovered she said, “That was fantastic! You are the first boy to eat me! I didn’t want Holly to know that she got you first. Hell that bitch wants you to take her virginity too!”

I smiled thinking that Debra had never called Holly a bitch before that I knew of. Debra was jealous because I ate Holly first! This could be good, especially if Holly wanted me to take her virginity too. Maybe Debra would give me hers first. One could only hope!

The next day was Friday. On our walk to school Debra said that she was a little nervous about me butt fucking her tonight but she said that she was ready. She had even gone to sleep with the dildo in her ass. It had fallen out during the night but her asshole felt fine when she took a crap this morning.

Debra also said, “I want you to do it right after school! We will have plenty of time before mom and dad get home so that we won’t get caught! Besides I’m kind of looking forward to it now!”

I smiled and said, “Me too! Thanks!”

All I could think about at school that day was butt fucking my sister. The day dragged. It was crazy! The more I looked at the clock the slower the time went. Out of desperation I actually started to pay attention in class just so that the day would go by quicker. It worked and soon I was walking home with Debra. Holly wasn’t with us. Thank God! Apparently Debra had told Holly what she was planning. Debra walked pretty fast and we got home quicker than usual. Debra had taken a shit during her last period so that she would be empty enough for me. I thought that she was on the right track and I also know that she was looking forward to it as much as I was.

Debra wanted to do it in her bedroom so that’s where we headed. We both got undressed and Debra got on her back on the bed and opened up her legs wide. She applied the K-Y Jelly to my cock and her asshole then took a deep breath. Then she took a couple more deep breaths before telling me to put the head of my cock at her opening but not to push it in. A couple more deep breaths and she told me to push just the head into her rectum. She smiled and said that I wasn’t as big as the dildo and that she was thankful. She had me press a little more into her in short strokes over a minute or so. Once I was all the way in Debra smiled and relaxed. When she started playing with her clit she told me to start fucking into her but not too fast or too hard at first. It was great! I loved her asshole more than Stella and Judy’s pussies put together. I think it was because she was my sister. Before long Debra was having her first orgasm from her finger then she stopped and just let me fuck into her rectum as I had been doing!

Soon Debra said, “You know that feels good! I mean it! It feels better than anything so far! Is that what having you in my pussy would feel like!”

I said, “Stella and Judy sure like it!”

Debra said, “I wonder how it would feel!”

Soon I was building up speed to match my sexual build up! Debra started humping up at me and her breathing got heavy too. Finally I was cumming in my sister’s rectum. It was incredible. It was the best fuck of my life! Debra said that she was having an orgasm right along with me and she wasn’t playing with herself either. I relaxed and my cock fell out of her butt. Debra relaxed and lowered her legs. I lay next to her for a few minutes. Soon Debra was kissing me and thanking me. Wow! It wasn’t a sisterly kiss either, it was better than Stella and Judy kiss.

Debra said, “Wow that was great! Can we do it again?”

I said, “Just give me a few minutes to get hard again!”

Debra said, “I can help you get hard! That’s my specialty!”

In about five minutes I was hard and back in her asshole again. This time Debra was on her hands and knees on the bed with me standing behind her. This way I could hold her hips and slam into her with as much force as I wanted. She wasn’t even playing with her clit she was just enjoying the feeling. Soon her tits were on her bedspread, her ass was up in the air, and I was pounding into her. This second time took longer but Debra didn’t seem to mind it at all. When I cum in her that time she just slid forward away from my cock unplugging me.

Debra smiled and said, “That was great but I think I need to stop for now! How about we do it again at bedtime?”

I smiled and said, “I’d love too if you’re up to it!”

Debra smiled and said, “I’ll be up to it! Don’t you worry about that!”


The End
My Anal Sister
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