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 s 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 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 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 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. She said that she would be happy to pose outdoors for me any time that I wanted her too. All right! I ran and got my camera but I only got to take two pictures of Madeline before dad came around to the backyard to mow that part. The two pictures were of Madeline with her mini skirt up and her top up for a great picture. Then she sat on the swing set with her legs spread wide open for the second pictures. I quickly put my camera in my back pocket before dad saw it.

As dad started up the lawnmower Madeline took me out front to pose some more. Holy shit! She sat on the front porch steps and spread wide again for me. She waited until she thought it was safe and then lifted her tight shirt up for me too. Then she suggested that we go over to Judy’s house for a while. She told me to bring my camera and then went in to ask mom’s permission and to call Judy.

It was all set. We walked about three blocks to Judy’s house. Judy’s mother was cool and let the three of us go up to her bedroom. Madeline told Judy all about the previous night, this morning, and about posing for pictures outside. Judy was literally squirming with excitement. Madeline told Judy that I had some kind of a date drug but that she had known everything that was going on and that I hadn’t even needed to use it in the first place. Madeline would have been perfectly willing if I had just asked her in the first place. Judy said that I didn’t need it for her either and asked me what I wanted her to do. I asked her if her door was locked. Judy smiled and locked it. Then I asked both girls to get naked and pose together for me. They were actually eager to do it for me and they even kissed, sucked each other’s nipples, and licked each other’s pussies for me. Then Madeline took pictures as I fucked Judy for the first time. Judy also was an unwilling virgin and was pleased to feel my cock in her pussy. Madeline photographed the cum shots then gave me the camera so that I could photograph her eating Judy out with my cum leaking from her pussy. It was simply amazing.

After that the girls got dressed. Judy didn’t wear a bra or panties either and put on a skirt and top similar to what Madeline was wearing. The girls sat on Judy’s front porch and spread their knees wide for me, on her back porch and spread too, and then out behind a tree lifting their skirts and tops up for me. It was all very exciting for us. At Madeline’s suggestion Judy lifted her skirt and bent over so that I could fuck her from behind outdoors like I had done to her. Madeline took some pictures for me. The whole idea of the incriminating pictures just seemed to make it even more exciting for all of us.

Before we left I told Judy that she had to set up some other girl within a week. She suggested Mary the next Saturday at our house. Madeline liked that idea too.

After that it was time to head back home. Along the way Madeline managed to flash me her pussy and her tits a few times each. She was really getting off on this exhibitionism stuff. Madeline even played with her clit as we walked home, giving herself a few orgasms along the way. Girls are lucky. They can cum in just a couple of minutes while us guys can jerk off for quite awhile before we cum. Plus they don’t have a telephone pole to hide either. All Madeline had to do was pull her finger out of her pussy and make sure that her skirt fell back down in place. To tell you the truth I don’t think Madeline would have minded if it hadn’t fallen back down. She really did like this exhibitionist stuff as I already said.

Just as we got to our house Madeline suggested that we drug mom next. We? What’s this we shit? Madeline wanted mom to get off her back about the way she had to dress. Mom had already cornered her a couple of times that day about not wearing a bra. I told her that I liked the idea of us as a team. We decided that maybe after school wouldn’t allow us enough time so we would have to wait for day off from school. Columbus Day was coming up in another week.

NOTE: Here in America we celebrate Columbus discovering Cuba or some other tiny island in 1492. October 12 is referred to as Columbus Day every year. However it now gets translated into the second Monday in October. Damn Monday holidays anyway. The only people that get it off are schools, banks, and the post office. The rest of us have to work as usual.

So by Columbus Day we would also have Judy and Mary to help us with mom. That would be good. Our prudish mother would be getting fucked by me and then to eat out three teenage girl’s pussies. That would be just perfect. She wouldn’t be able to do anything about it either.

Madeline and I fooled around every chance that we got that week. Judy joined us occasionally too. Everything was all set for Mary on Saturday. Madeline got permission from mom to let the two girls spend the night on Saturday as long as I behaved myself. Yeah right, me behave myself!

Judy and Mary arrived before mom and dad left for their regular Saturday evening pinochle game. Mary said that her older sister Terri wanted to spend the night too if it was all right. Mom thought about it for a while and then said that it would be okay. Mom and dad left before Terri arrived. It was a good thing too because mom would not have approved of the way Terri was dressed. She had on the lowest pair of hip hugger pants that I had ever seen. I couldn’t believe that I didn’t see any pubic hair. Terri was in a couple of my classes in school and I have been in love with her for years but of course I had never told her that.

Shortly Madeline and Judy suggested that I spike the girl’s drinks. Judy helped me in the kitchen while Madeline entertained the sisters. I spiked the two red glasses then filled them all with Pepsi. Judy held the doors for me while I carried the drinks on a tray. Judy picked up the two red glasses and handed them to Mary and Terri. She then handed another glass to my sister and I before taking one for herself. She raised her drink up and said, “Here’s to an interesting night!” Everyone said cheers and drank a good portion of their drinks.

Right away Madeline started talking about loosing her virginity the week before. Then Judy told of loosing her virginity the very next day and to the same boy too. Mary was not interested in who the boy was but Terri sure wanted to know. When the girls told her that it was me Terri got all excited about it and said that she wanted to loose her virginity to me too, if I wanted to take it. I had often dreamed about having sex with Terri. You bet your sweet ass that I wanted her virginity.

We all went up to my bedroom so that I could take pictures. Since Terri was more susceptible than her younger sister was I had Terri undress herself first and then undress her sister Mary. I had them pose separately, together, and then I had them start making out together for me. It wasn’t their first time either because I asked them. When I had seen enough, I got between Terri’s legs, and slipped my cock into her juicy pussy. Terri had nicer tits and more hair on her pussy than the other three girls had. Terri kissed very well too. I enjoyed fucking Terri that’s for sure. I slipped my cock in and out of her slick pussy until I cum. She orgasmed at the very same time that I did. It was timed perfectly and I hadn’t even planned it. I was just taking care of my own sexual needs. Terri was wonderful.

Next I fucked Mary. She resisted a little in her own way by not totally enjoying it. It was useless but it didn’t matter. I would get to fuck Mary again later and then anytime that I wanted to after that. After all I was becoming the blackmail artist.

Terri did everything that I wanted her to do to the other three girls and sometimes much more than I had asked her to do. On the other hand her sister Mary only did just what I asked of her. Terri gave me a great blowjob and swallowed my cum. Later that evening I got my very first piece of ass literally. I anal fucked Mary. If she was only going to do just as I asked of her so be it, I asked her for anal sex and she gave it to me.

I sent the three younger girls to Madeline’s bedroom to sleep but I kept Terri with me in my bedroom. At least until mom and dad came home. I was wondering if the pill lasted six hours like the pharmacist had said. It was hard to tell because like Judy Terri really wanted me all along. However she thought that it was about six hours. So we checked on Mary. Sure enough Mary had come out of its effects too and she was mad as hell at me. This was something new to me but her biggest complaint was that her ass hurt. She didn’t mind that I had fucked her pussy and taken her virginity but she wasn’t happy about me fucking her ass. I asked her if she remembered everything that she had done and all of the pictures I had taken of her doing them too. She did and she calmed down a little bit. I told her that as long as she kept quiet about that night and got me another girl within a week to add to my collection that no one would ever know about what she had done from me. Then she said that she had already gotten me another girl, her sister Terri. I had to laugh because she was absolutely right, she had brought Terri to me so I looked at Terri. Terri promised to get me another girl from our class within a week. I heard mom and dad coming home so I kissed Terri goodnight and went straight to my bedroom.

First thing Sunday morning Terri was right in bed with me wanting some more sex. Wonderful! This time we made love slowly and very passionately. Terri said that she had really wanted to have sex with me and that was the whole premise behind her tagging along with her little sister on a sleepover in the first place. That was the best sex I had had so far. I really like Terri. She said that she didn’t mind if I fucked other girls and was more than willing to help me fuck them too. That’s when I mentioned that the next day was Columbus Day and what I had in mind for my own mother. Terri was all for it and wanted to help out.

Mary came in after Terri and I were finished making out and actually apologized to me for being suck a bitch the night before. Her ass didn’t hurt that morning and it felt all right. She told us that Madeline and Judy had explained to her what the deal was. Then she asked me if I wanted her to get me another girl to fuck within a week. Terri whispered in my ear to let her, so I said yes. Then Mary said that my sister had told her that I might like to fuck her again before my parents woke up. Terri lifted the covers and told her to get in. Mary had seen that we were naked so she removed her nightgown and climbed in with us. It was cute when she said that I could fuck her butt again if I wanted too. I thanked her for her offer and said maybe some other time but that right then I just wanted her pussy with her on top. She smiled and straddled my waist. I was hard enough for her to sit on my cock so she did. Terri lay next to me and made a few suggestions to her little sister that gave her a pretty good orgasm. She liked being in control. I like being in control too!

We ended our lovemaking and I sent the girls in to take a shower together. I had Madeline take a few pictures for me.

After mom and dad got up I had the four girls talk mom into letting them spend another night at our house. After all there was no school on Monday. Besides it would be great to have them all here so that we could get started as soon as dad left for work. Mom gave in and the three girls called home to get permission from their parents too. Everything was all set.

Monday morning mom could not believe that we were all up and wanted to eat breakfast with dad before he went to work. We ate slowly waiting for dad to leave. Mom always eats last because she is the cook. So we were all there when she finally sat down. I had spiked her drink when she was kissing dad goodbye so when she was drinking the drug we just talked about what a great day it was going to be.

I waited about fifteen minutes then boldly reached out my hand and cupped one of mom’s breasts. She just looked at my hand, then looked at me, and smiled. That was what I was waiting for so I told mom to remove her blouse. Together we all watched as mom unbuttoned her blouse and removed it as I had asked. Next I asked her to remove her bra for us. Mom reached around behind herself and unfastened it allowing it to sort of sag in front under the weight of her breasts. The girls were dead quiet and watching intently. They too could not believe that my prude of a mother would do this in front of us. Mom pulled her arms out of her bra straps but her breasts seemed to be holding the bra cups in place all by themselves. Finally mom removed the cups setting her tits free. I watched as they jiggled and swayed on her chest from their newfound freedom. Mom’s tits were bigger than I had imagined. Her nipples and areola were much darker in color than any of the younger girls sitting at the table with me. Mom’s nipples were also larger and looked like they were made to be sucked. Mom told Madeline and I that we were breastfed babies, so at one time I had already sucked on her nipples. I was looking forward to doing it again. I had mom straighten her shoulders so that her breasts stood out even further, then I told her to finish her breakfast.

Our conversation had changed to sex as we watched mom eat and finish drinking her orange juice. When she was finished eating I had mom remove her long conservative skirt to reveal her big white granny panties. That’s what Madeline always called them whenever she had to do the laundry and mom wasn’t listening. Then I told mom to remove her panties for us. This time she actually tried to resist me but only for a few seconds. Mom looked embarrassed as she lowered her granny panties to her ankles and stepped out of them.

Terri noticed that mom had made a wet spot in the crotch of her panties. Apparently eating topless in front of five teenagers had stimulated her.

Terri asked mom, “Did eating topless make you wet?”

Mom answered, “Yes it did!”

Terri laughed and said, “Is this a truth serum too?”

I said, “I don’t know! Mom! How many men have you fucked?”

Mom answered, “Only three!”

I asked, “Who?” Then I thought about Mom’s short precise answers she was giving us and added, “And give us details too!”

Mom then answered, “Fred Hart my boyfriend throughout most of high school, your father of course, and Harry Morgan last New Years Eve when I had too much to drink! He sort of took advantage of me”

Terri started laughing and said, “You let my father fuck you!” Then she and her sister Mary laughed out loud even harder. Terri then said, “That means that he has fucked all eight women in the Saturday pinochle game. My mother being one of them!”

Mary said, “That’s funny because he usually brags it up when he fucks some other woman! Then mom fucks his brains out for a month afterwards! Dad’s a real horn dog!”

Mom then said, “He’s not much of a fuck when he’s drunk though!”

I then said, “Mom! How many women have you had sex with?”

This time mom blushed as she answered, “I had sex with all three of my sisters but I was really young at the time! Just a teenager!”

So I asked, “Would you like to have sex with these four young girls?”

Mom blushed again and said, “Yes, I really would!”

I said, “Then afterwards will you let me fuck you?”

Mom blushed again and said, “Yes, I will!”

The six of us then went up to mom’s bedroom. The girls got naked and took turns making out with mom as I took pictures of them. Madeline wanted to be first, followed by Judy, Mary, and then Terri.

Madeline wasn’t going to just eat mom’s pussy. She turned around and made mom eat her pussy too. Mom was really into that and gave Madeline three orgasms to the two that she had received from her daughter. Mom was equally good at providing Judy and Mary with an extra orgasm too! Then came Terri. Terri was not going to be outdone! She gave mom two orgasms for every one that she had received. I noticed that Terri had made mom get on the bottom and that she had worked two of her fingers into mom’s ass while she ate her pussy. I was the only one on that end, the rest of the girls were watching mom eat Terri’s pussy on the other end. Madeline got pictures of both ends for me.

Watching Terri finger fuck mom’s asshole gave me the idea of butt fucking her. Mary got so she liked it up the butt so mom might too. When Terri had finally given and received enough orgasms she got off from mom.

Then it was my turn. I stuck my cock in mom’s face. She started sucking on it like it was a lollypop.

I asked, “Mom how many cocks have you sucked?”

Mom answered, “The same three that fucked me! Plus my cousin Steve!”

I then took my cock away from her and put it in her pussy while she was on her back and I was between her legs. I slipped it in a few times to get it moist then I lifted mom’s legs up around my waist and slipped my cock into her asshole. Madeline had been taking pictures as I went.

I asked, “Mom how many cocks have you had in your ass?”

Mom smiled and answered, “Only yours honey! Only yours!”

I butt fucked mom for too short a period of time. Watching the girls had gotten me way too excited. However I would have time to fuck mom a couple more times before dad would get home. I had mom pose nude for me in every room in the house. I had her take a shower and a bath too. Madeline suggested that mom put on the shortest skirt and sexiest blouse that she owned and go out to pose on the swing set for me. From there the girls had mom do things that even they wouldn’t dare do. I put an end to that when I told them that they had to do whatever they told mom to do. They cooled it considerably.

Before dad got home mom swallowed a load of cum and took another load in her pussy. Mom became the first woman that I had used all three of her openings for sex. The four girls posed with mom for group pictures too. Mom’s pill wore off after six hours and of course she remembered everything and asked me what I intended to do with her. I told her that I wanted a little more leeway after school with girls and that every Saturday evenings we were going to have girls over too. Mom simply said okay. I told her that Madeline needed to dress more like the other girls in school. Mom simply said okay. I told her that I would want to fuck her occasionally. Mom smiled broadly that time and said okay very energetically. Then I told mom that she would have to set me up with one of her sisters to drug and fuck. That time mom said okay but certainly not as energetically.

Dad came home right after that, the other girls went home, and Madeline came up to my room.

Madeline told me that Terri was going to bring two of the girls from my class to our gathering this Saturday.

At bedtime mom came in to kiss us both goodnight before going to bed with dad a couple of hours early. It seems that he had gotten pretty horny staring at Terri in her skimpy outfit when she was here. She certainly had that effect on me too. Mom kissed us both on the forehead as she always does and then she kissed Madeline’s pussy and my cock goodnight too. That was nice.

As mom was standing next to my bed she said, “I want to thank you both for everything you did today! I really enjoyed myself!”

Madeline laughed and said, “You weren’t supposed to enjoy it mom! We were supposed to blackmail you into doing stuff against your will!”

Mom laughed and said, “Oh! Okay! I’ll try to do better! Your father has to go into work early every day for the rest of this week! You can spank me in the morning before you go to school?”

I smiled and said, “Okay!

Mom then smiled at us and said, “You two should get some sleep too, you know!” Then mom tucked us in and went to dad.

The End
Blackmail Artist