Shoplifting Has Its Consequences
Copyright© 2025 by Rachel 42
Chapter 3: Breaking In Roger
True Story Sex Story: Chapter 3: Breaking In Roger - A young teen is caught shoplifting and pays the price.
Caution: This True Story Sex Story contains strong sexual content, including Blackmail Fiction True Story Incest First Masturbation Petting Squirting
Roger smiled at me and said that he would really appreciate me jacking him off, so I rolled on my side and took his hard cock in my hand and gently and slowly began stroking it for him. He was such a horny and needy young man. Roger hadn’t had much sex in his life, he had never been laid, and I was the first female to ever touch his cock, all his sexual experiences had come from jerking himself off.
Roger was also very good at shoplifting, and one of the things he would steal would be men’s magazines. He would look at the pictures as he stroked his cock until he reached his goal of cumming.
Roger laid back on the bed and then he began to talk a little: “Oh fuck sis, you are making me so fucking horny, I really wish I could fuck you right now. Oh, fuck Rachel, go faster, I want to blow so bad.”
I sped up what I was doing until I could see that he was ready, I jerked his big cock a few more strokes and then he shot a huge load all over his own stomach. I kept stroking him for a short while longer until he was completely drained and satisfied.
After making him cum, I whispered in his ear, get some condoms and you can fuck me Roger, I would love to feel your cock in me.
A short while later, mom walked out of the bathroom, completely naked of course, she was carrying a towel but wasn’t trying to hide any of her perfect body. Mom was in great shape, nice big tits, a thin waist and not a pound overweight, I must admit she looked fabulous, and I could tell that Roger thought so too. He made it obvious to me that he loved looking at mom’s nakedness.
Mom walked over to the coffee pot, poured herself a cup of coffee and then went over and sat at the table without bothering to put anything on or to cover anything up. That was normal for her, she just didn’t care who saw her body, probably because she was quite proud of her body. She had the attitude that if you didn’t like her body, then don’t look at it.
Roger and I rolled out of bed, Roger was still covered in his cum from getting jerked off, and we were obviously both naked. I walked over and got myself a cup of coffee while Roger went to the bathroom to take a shower and get cleaned up. I poured the coffee and went and sat with mom at the table.
Mom told me that she was so proud of the way I looked, she liked the fact that I had developed so young and that my body, like hers, was in great shape, I wasn’t overweight, and she said that I looked fabulous. Hearing those words from your mom is very satisfying.
I really wanted to know about last night, especially the part about being with a married man. So, the first thing out of my mouth was a question: “Mom, how does it make you feel knowing that the man you let fuck you last night was married?” Mom just smiled at me and quickly answered: “Rachel, as you get a little older you are going to learn a lot about men and how they think and how they act. If I didn’t fuck that guy, then some other slut would. He was out to get his rocks off, he didn’t care that he was married, so why should I care if he is married. I only wanted him for an hour or so and he only wanted me long enough to fuck, so now it over and nobody cares.”
I smiled and told her: “You know mom, before I am sixteen I wanna let a married man fuck me, and I wanna fuck my brother Roger. I might even try to get two guys at once, have you ever done that mom?”
“Rachel, I have done a lot of things in my life, yes, I have had more than one man at a time, and it’s happened a few times. It is great, but you need to be careful. As for fucking a married man, that won’t be hard at all, and fucking your brother, just make sure he uses a condom, that is one guy you need to make sure doesn’t knock you up. Those are some easy goals.”
“Well mom, I was thinking of going back to the grocery store and seeing if that store manager would be willing to pay me some money if I let him fuck me, and I thought I might be able to convince him to come over and fuck you too, would you like that mom?”
“Oh fuck Rachel, that would be cool, of course I’d like to fuck him, and I think he just might want to do that, mem are men, they like sex and they are willing to do a lot of things in order to get what they want, and there is no harm in trying.”
Later that day Roger and I went uptown and were wandering around until we came to the pharmacy store. Roger looked at me and said that he was going to go inside and see if he could steal some condoms. I told him that I wanted to steal so me too in case I wanted to get fucked and the guy didn’t have one of his own.
Roger went into the store and after waiting a minute or so, I went in also. I looked around at a few things and then went to the area where the condoms were located, as it happened, the pharmacist behind the counter was busy doing something else, so I picked up two packages of condoms, lifted my skirt and stuck them in my panties. Then quickly let my skirt fall back into place. I wandered around a little more and then left the store. Mission successful.
I met up with Roger outside the store, he had also been successful and had also stolen two packages of three condoms. We giggled a little as we walked back down the street.
I looked over at my brother and asked if he was now ready to get his first piece of tail. He had a huge smile on his face as he responded: “Oh yes Rachel, I am so looking forward to fucking you, I want it so fucking bad.”
I answered him: “Well little brother, let’s do it right, and have it in bed, unless of course you would rather we did outside somewhere.”
“I just want to fuck you Rachel, I don’t care where, I just really want to fuck you.” Roger said. Then he looked at me as he stopped walking and added: “Mom is out for the day Rachel, why don’t we go home and do it now?”
Without letting him know that I wanted his cock as much as he wanted my pussy, I hesitated a little and then answered him: “Sure Roger, lets head home and see how good you can be.”
Roger’s response was quick and to the point: “Let’s go Rachel, but you have to help me and show me some of the things that girls like too.”