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Author Topic: On Probation (F/M, Sister/Brother, Incest, Oral, Teen, MILF)  (Read 1130 times)
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RedHoodTodd
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« on: November 14, 2020, 05:06:09 PM »


This is a work of fiction.  You must be 18 or over to read this story.  In real life, incestuous relationships, particularly when an under-aged person is involved with a parent or adult, often causes deep psychological damage.  This story is provided for entertainment purposes only.  The author does not condone any sexual activity with persons under 18 in real life.






                      My Parents were going out of Town again for their Anniversary, unfortunately I was going to left alone at Home, only this time they decided that my older Sister, Valentine (yes, that's her name, my Mother gave birth to her of course on Valentine's Day, hence her name. We just call her Val for short), was going to be staying with me to keep me out of trouble. The last time they went out of Town and I was left alone I had invited some friends over for a Party which got out of hand and I was in big trouble when I got pulled over by the Police when I went out to get more beers, unfortunately I was not old enough at the time to go get beer especially with a fake I.D. and I was driving under the influence.


                        Lucky for me my Father got me off from going to Jail in the County lock up, but since it was my first offense I just got three years of Probation, my driver's license was suspended for a year and of course my Father took my keys to my Car for the year as punishment. I also got double lucky for the Judge and my Father were very good friends, I was allowed to have my Sister Val as my Probation Officer. My Sister became one because like our Father she was interested in the Law, but instead of following in his footsteps, she wanted to be a Probation Officer, trying to keep people especially young offenders, like me out of trouble. Val was extremely happy when she found out that she was going to be my Probation Officer, little did they know, her excitement for me was hidden by the fact that my Sister has a infatuation with me, even though she's the oldest of us Kids and I'm the youngest of the four, she has always been in love with me. She is the one who took away my virginity when I turned 18 as her "secret" Birthday gift to me. For some reason why I will never know, Val has had her incestous crush on me, our other Sisters never have, but she certainly has and still does to this very day.


                        Even after being Married to her ex-husband and having two kids of her own, she has always desired my Brother dick. Since I am still on Probation under my Sister's care she was the only one who was perfect to keep me under supervision and out of trouble at least with the Law, but staying out of trouble with her wasn't going to be easy. That first night after our Parents had taken off for their trip, Val was on the telephone talking with our Sister, Sarah who was watching her Kids while keeping me company. Val spoke to her Kids while I was watching TV in the Living Room of the Guest House out back of my Family's Home (my Father had it built so guest could stay out there when visiting and spending a night over, but it became my Probation sanctuary since I got into trouble, my Father put my ass out there and away from the Main House as punishment). The Guest House is not so bad, not as fancy as the Main House, but it feels like a nice Home, but I felt like I was in was in a bachelor's pad for a guy who was recently divorced and his Wife was taking him to the cleaners. Anyway, you should have seen how Val was dressed. She was wearing a sexy yellow dress with a very short skirt, she wore white stockings that went up past her knees, she wore black high heeled shoes. When she bent over earlier in the kitchen when making me Dinner, I could see she was wore a skimpy pair of purple panties, I also could see that she was wearing a red bra as well. As she kept talking to Sarah, I could see her looking at me trying to flirt with me and trying to get my cock up by spreading her legs trying to show me her panties. Of course being a guy I couldn't help but look.


                      "Yes, I'm here with him now. He's just watching TV.", I could hear Val say to Sarah. My dick keep getting harder as Val continued flashing me, then she handed me the phone to talk to Sarah as she excused herself to the bathroom. Sarah told me that, "You shouldn't be too upset with Dad after he punished you for getting into trouble and it is for your own good. If you continue to do what he and Val says he might get you off of probation." I sighed, "Yeah that's true, what's the worst that could happen to me.", just as I said that Val returned in the Living room without her yellow dress. I thought I was going to explode in my pants when I saw her again. Val wanted the phone back so she could talk to her Kids before they went to bed. I handed her the phone back all the while she talked to my Niece and Nephew, Val continued to flirt with me.


                     Now she removed her bra to show me her small breasts, her pink nipples looked like they needed to be kissed and licked, next she put up her right leg in the chair she sat in, pulled her purple panties to the side and showed me her hairy, wet, MILF pussy, during that time I took off my t-shirt, then took off my jeans. I was in my underwear as Val licked her lips from seeing the bulge in my underwear and mouthed the words, "Stick your Brother cock right here."
Once she did, I instead got down on my knees in front of her hairy pussy and started licking it. Val showed her appreciation by rubbing her fingers through my hair as I ate her Fluff. Val said Goodnight to her Kids and our Sister Sarah, then her attention turned to me eating her pussy. Val had me stop as she took off her shoes then her panties. Val didn't want me to eat her snatch anymore, she and I started to kiss with our tongues, then she yanked my underwear down to free my nine inch cock.


                     Looking at it with her pretty blue eyes, she pushed back her long brown hair and swallowed my cock down her throat to suck my 19 year old dick. I stood in front of her as she continued giving me a blow job adding some licks on the head and shaft of my cock. Then she took my cock to rub all over her lips like she was putting on a fresh stick of lipstick which was quite hot to watch. I grabbed a hold of my Sister, took her into the bedroom as she laid on her back with her knees bent, legs spread wide as I slipped my hard teen dick into her 37 year old pussy. I know I shouldn't do this, but she is horny as fuck for my dick plus I don't know any better either. Val moaned like crazy as my 9 inch 19 year old cock fucked her juicy wet bush. The room was filled with sounds of us fucking and her moans,it was driving us both crazy. I have not had any other pussy since I got into trouble, I feel that is the same for Val since her divorce and since she has been smitten with me all of my life having my cock pounding her will make her feel better.


                        My mind raced as I fucked Val, I was just happy to get some relief from being punished by Dad I'm sure that she was happy to get pleasure since she was dressed for it, I just hope that she won't cut me off or turn around and tell Dad I broken my Probation just to get me into more trouble. Right now I just tried not to think about that as I had Val in Doggy style fucking her creamy twat still. I tried so hard to not cum inside of my Sister's pussy, I thought if I did that and got her pregnant by mistake that she could use that against me so I pulled out of her pussy and blasted my load all over her face, Val stuck out her tongue like she was about to receive Communion and my cum coated her long tongue. She let my cum drool out a bit from her mouth then she swallowed it down her throat. "Thanks Andy, you know how to make a Woman feel good.", she said with an infectious grin. "You're welcome, Val. I just hope that this doesn't effect my Probation.", I replied. Val laughed hysterically. "Why would it, ya Knucklehead? I told you before that I love you, ya lunatic! Relax and stop being paranoid.", Val said as she cleaned her face and my dick.


                         "If you don't behave I'm going to slap your cock!", Val said as she took off to go shower. I laid back on the bed thinking about what she said, I shouldn't be so paranoid about anything. I went to the kitchen, cracked open a can of Coke and waited for my turn in the shower. Val returned wrapped up in a couple of towels and shoved my ass into the shower. "Clean up or I might make you go clean up a Highway with a bunch of Inmates from a Prison.", Val said laughing and stealing my soda. Fuck she is one crazy Lady. Once I finished my shower and put on sweats, I found Val taking off to the Main House, but she left me a note which read, "There's ice cream in your freezer and if you behave yourself I might let you come up to the Main House tomorrow, but it will be our secret. Kisses Valentine" which was marked with her lipstick lips. It's hard to control myself around her.

The End
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TMacc
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« Reply #1 on: November 19, 2020, 12:38:27 AM »

Thanks, enjoyed it
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RedHoodTodd
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« Reply #2 on: November 21, 2020, 06:53:17 AM »

You're welcome, I'm glad.
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