Blackmail Artist

Blackmail Artist


At age sixteen I am a blackmail artist. It all started when I was a stock boy at the local pharmacy. One day I overheard the pharmacist talking to one of his friends. He told his buddy to drop one of the pills in her drink and wait about fifteen minutes. Then he could do whatever he wanted to do to her for about six hours and that she couldn’t resist. However she would remember everything that he had done to her so he would have to do something to force her not to tell her parents or the police. The guy seemed confused so the pharmacist told the guy to take some nude pictures of her and threaten to make copies and give them to her minister, her schoolteachers, and even the entire football team if she didn’t cooperate.

I watched when the pharmacist put that bottle back on the shelf and just as soon as he went out for a smoke I took ten of the pills out of that bottle and wrote down the name for future reference.

My fist victim was my sister. Madeline was fifteen years old. She was basically normal but kind of sexy too. She had long straight brown hair to her waist. She was kind of prudish but she got that from our mother. Mom never let Madeline wear anything too revealing or too sexy. However Madeline was starting to resist and talk back to her occasionally. Madeline desperately wanted to become normal.

Our parents had a regular Saturday pinochle game at their friend’s house and had for a long time. We kids were dragged along or left with a babysitter for years until we were old enough to stay home alone. Even so mom would call us one or twice each evening just to check on us.

We were good from about six to midnight on Saturdays so that’s when I decided to do it. I slipped a pill into a glass of Pepsi and took it to Madeline. I looked at the clock and waited for the fifteen minutes. I didn’t know how to test it so I simply reached out and played with one of her tits. Madeline just smiled at me so I reached up under her skirt and she opened her legs up for me. This was great so I started undressing her and Madeline cooperated fully. I had only imagined seeing my sister naked before that. This was fucking fantastic. Once I had her totally naked I took her to my bedroom and told Madeline to lie on my bed, she did. I got out my camera and took several digital pictures of her naked on my bed. Madeline cooperated totally doing everything that I asked of her. She held her breasts for me, she pinched her nipples, and she even opened up her pussy while I took nude pictures of her.

As long as she was like this I decided that I just had to loose my virginity. I knew that Madeline was a virgin too. When I asked her if I could fuck her she said yes. I was pretty sure that it was the pill but what to hell, I really wanted to fuck her after looking at her naked and taking all those pictures of her. So I got on the bed and put the head of my cock just at the entrance of her pussy and took another picture. I put the camera down and slipped my cock all the way into my sister’s pussy. There was no resistance at all so I asked Madeline about it. She smiled and said that her girlfriend Judy had taken care if it for her some time ago with one of her mother’s dildos. I got really excited and picked up speed and fucked into my sister faster and harder until I came. I knew that mom had put Madeline on birth control so I knew that it was safe to cum inside her. I grabbed the camera and took more pictures of my cock in her and then I pulled out, had her hold her pussy lips open, and took some cum pictures. Then I took more pictures of Madeline on the toilet and in the shower. Then I sent her to bed.

In the morning she woke me up. Madeline had remembered everything including the pictures and the sex. She wanted to know what I had done to her and what I was going to do with all of the pictures. I told her that I had drugged her and that the pictures would be safe as long as she helped me do the same thing to her girlfriend Judy the following Saturday. Madeline was a little too eager when she said okay. She even said that I might not need to drug Judy. I told her that I wanted to drug Judy but that she herself wouldn’t be drugged that time. I told Madeline that I wanted her to do it on her own that time.

Surprisingly Madeline opened her bathrobe up to show me that she wasn’t wearing anything. She told me that she wasn’t drugged then and that she was still willing to pose naked and to let me fuck her if I wanted too. She reminded me that mom and dad always sleep till noon on Sundays after the card game. I smiled and lifted up my covers so that Madeline could climb in bed with me. This was nice having a willing sister to fuck and she wanted to help me drug her girlfriend too. Fantastic!

This time I kissed Madeline softly. I really needed more practice kissing and so did she. I played with her nice tits and she asked me to suck on her nipples. She liked that and so did I. She asked me if I would lick her pussy like Judy does and I asked her to suck my cock. So we got into a sixty-nine and started to give each other oral sex. I told her that I wanted to cum in her pussy and to take it easy. She wanted that too. I gave her one orgasm then knew that I had to fuck her. She came up out of the covers and got under me so that I could fuck her properly. I liked slipping my cock into her like that, with her being drug-free and willing that is. I actually wanted to fuck her in every position that I had ever heard of. Madeline wanted that too. However right then I just wanted to cum. After I shot several blasts of cum into her she asked me to take some more pictures of her so I did. She posed very sexily too. I sat the camera on my computer desk and hit the self-timer. Madeline and I posed together for a few very interesting pictures. She knelt and sucked my cock, she bent over so I could slip my cock into her from behind, and as I sat in my chair Madeline sat on my cock facing the camera. I took some more shower pictures too before mom and dad got up. Madeline was great!

Mom was not pleased when Madeline came to Sunday lunch in a short mini skirt and a tight top without a bra on. If she had known that Madeline wasn’t wearing any panties either she would have thrown a fit. Madeline made sure to show me her pussy as often as she could.

While mom was doing the dishes and dad was mowing the front lawn we went into the backyard and got behind the garage for some privacy. Madeline lifted her mini skirt up to her waist, bent over grabbing the slid on our old swing set, and then let me fuck her from behind. Afterwards she squatted and let my cum leak out of her pussy as well as taking a piss for me too. I wished that I had my camera with me so Madeline told me to go get it.