Shoplifting Has Its Consequences
Copyright© 2025 by Rachel 42
Chapter 12: Tyler
True Story Sex Story: Chapter 12: Tyler - A young teen is caught shoplifting and pays the price.
Caution: This True Story Sex Story contains strong sexual content, including Teenagers Blackmail Fiction True Story Incest First Masturbation Petting Squirting
I woke up the next morning, and quickly realized that I was leaking down below, I had my period. I knew it was due any day, so I had worn panties to bed. Mom didn’t get her period any longer, she had her tubes tied shortly after the birth of my brother. I reached into my dresser drawer and realized that I only had one tampon left. I did what I needed to do, put the tampon into my vagina, pulled on a clean pair of panties and went out to the kitchen to make some coffee.
Mom got up a little while later, and joined me at the table for coffee, mom had also put on a pair of panties, and we sat together having coffee. She told me that she had decided to go into town that night, probably staying over and working again tomorrow night, the rent was due soon, as were some of the other bills, she told me that I was welcome to join her if I wanted to. I told her that I would have liked to, but that morning I had woke up with “the curse”. She knew exactly what I meant. “Well, then unless you just want to give men blowjobs, I will go alone.” I hadn’t thought of doing that but decided against it. “No mom, unless I can do it right, I will pass on this trip, but I want to go again, I would love to make some more money.”
We sat together enjoying our coffee and talking like girls do with their mothers, a short time later we were joined by my brother, Roger. He came out wearing his jockey underwear and nothing else, I looked at his cock area, and I was pretty sure he was hard or very close to it.
“Can I fuck you today, Rachel?” he asked me without any thought of how direct he was. I answered him: “No Roger, not today, not for the next couple of days, it’s the wrong time of the month, sorry.” He looked disappointed, but he was wise enough to know exactly what I was saying.
“It’s hard waking up in the morning, walking out here into the kitchen and seeing you and mom sitting there with your big fucking tits, I get horny looking at them.” he said to us as he got up to get his coffee. Then I was surprised when mom said: “You can fuck me if you want to Roger, have you ever considered fucking your mother?”
I was shocked, so was Roger, I don’t think he had any idea of how to respond to mom’s offer. I knew he wanted to fuck her, but I didn’t know if he was ready to admit it. “Are you sure mom, are sure you want to let me fuck you mom?” Mom smiled and looked at him: “Yes Roger, if you want to, you can fuck me today, I can’t get pregnant or anything like that, so it will be okay, you have grown into quite the little man, and I am willing to give you what all young men need and want, so yes Roger, you can have me this morning.”
I had a few things that I wanted to do this morning too, I had to go to the pharmacy and get more tampons, I wanted to open a bank account and put my money in there, and I had to return the clothes I had borrowed from Bobs mom. After finishing my coffee, and knowing that Roger and mom were going to get it on, I went into the bedroom and got dressed, I counted out my money that I had been stashing away, I had six hundred and forty dollars, so I decided to keep the forty and deposit the six hundred. I put on one of the white bras that I had gotten from the department store, it looked nice on me, I wore a button up pink blouse and a short black skirt, and told mom and Roger to have a good time, and that I would see them later.
My first stop would be at the bank, I needed to open an account, something that I had never done before, or ever thought that I would have any money to deposit into an account. The teller looked a little surprised when I handed her the money that I wanted deposited. However, she was very helpful, and I walked out of there feeling a lot better about what I had just done.
Then I started walking towards Bob’s house to return the clothes his mother had lent me. Bob and his mother seemed to be quite surprised, but also happy to see me. They invited me in for a coffee, and I accepted and joined them at their poolside table. Bob’s dad had already left for work, so it was just the three of us. Bob was so excited to see me, and after all this time, his mother finally told me her name and asked that I call her Jean.
“How have you been Rachel, we have been thinking of you and hoping that you would drop by for a visit.” she said.
I responded: “I have been fine; I decided not to tell them anything about getting busted at the department store. Just getting a few things done today that I need doing, I opened a bank account today, my first one ever, so that made me happy, I had to bring your clothes back, and now I have to stop off at the pharmacy and get some tampons, it’s that time of the month, I am sure you know exactly what I am talking about.
Bob looked at me and asked: “Do you want to take a dip in our pool Rachel?” I quickly answered: “Well Bob, as much as I would love to, I don’t have a swimsuit and like I said, it’s the wrong time of the month.” Bob looked confused, and then Jean said: “I don’t think he knows what you are referring to Rachel, I will explain it to him later.” Again, Bob looked confused.
My visit lasted for over an hour and then I left and went to the pharmacy to get my tampons. It was about a fifteen-minute walk. I went inside, thought about stealing them, but then decided against it, and I paid for them and left the store.
As I was walking down the main street, a familiar boy that I knew from school as Tyler stopped and asked: “Hey Rachel, I’m Tyler, I remember seeing you around school a few times, I always thought you were a hottie, anyway, tonight I was planning on going to the drive-in theater, and I was wondering if you would like to be my date?” I did remember him from school, although he was a few grades ahead of me and probably at least eighteen years old. I was flattered that he would just ask me out on a date, I had never been asked out on a date before, just had guys that wanted to mock me or fuck me.
I thought about it for a few seconds and then said “I guess I could do that, I have never been to the drive-in theater before, so it sounds like fun.” He had a huge smile when I agreed to go out with him.
“I know where you live Rachel, I will swing by about seven o’clock and pick you up, does that work for you?” he asked.
I didn’t know how he knew where I lived, but it really didn’t matter, so I answered him: “Yes, that works Tyler, I will be waiting for you.”
I continued walking down the street thinking about what had just happened, a boy, and a nice boy at that, had just asked me out on a date, I was excited, I was looking forward to him coming and picking me up and taking me to the drive-in theater, if he even showed up. Then the doubt set in, what if he doesn’t like me, what if he doesn’t like my clothes. What if he thinks I am stupid. I tried not to think of those things, but I couldn’t help it. I walked home and went inside the house. Mom had already left for the city, Roger was sitting on the couch, still in his underwear.
“How was mom Roger, did you enjoy fucking her, did she teach you anything?” I teased him.
Roger said: “Mom was good, she is so experienced Rachel, she sucked my cock for a long time, asked me to eat her out and then she let me fuck her, and fuck her I did, she was hot, she had an orgasm, maybe two, she got really horny Rachel, she is a lot like you are.”
“I am so glad she was good, I knew she would be, did it bother you at all, knowing that she was your mother?” I asked.
“No, not really, I mean I have seen her topless and even fully nude so many times, it was fine, just another good fuck, that’s all.” he answered.
As evening rolled around, and it was getting close to seven o’clock, I decided I better get dressed, I chose one of my newer white bras, a plaid blouse with the buttons on the front, and a short black skirt. I wore my panties that had ‘Friday’ inscribed on them.
Tyler pulled up in his car at seven o’clock sharp, he was right on time, I liked that, I thought that it meant that he wanted me and that he couldn’t wait to be with me. I walked outside and he got out of his car and opened the door on the passenger side for me. I liked that too; he was being a perfect gentleman. I slid onto the car’s bench seat and then slid myself over so that I was seated next to him.
He looked at me with a smile and said: “You look beautiful Rachel, thank you for accepting my date request, it means a lot to me.”
I answered him: “I’m glad you asked me out, I have never been to the drive-in before and I am so looking forward to it, so thanks for asking me out.”
The drive-in was a short fifteen-minute drive away, we got there a little early and found a good place to park, set up the speaker on his window, and then he suggested that he sit on the passenger side so that the steering wheel would not get in his way. He got out of the car and walked around and got into the passenger seat, I stayed where I was. He was leaned up against the door and he put his arm around me and gently pulled me towards him so that my head was rested on his shoulder.
“Tell me Rachel, why did you accept going out with me?” he asked as if to break the ice. I answered him: “Why did you ask me out?”
His answer was simple: “Rachel, I remember seeing you at school, I thought you were such a good looking girl, I wanted to ask you out many times, but I was afraid you would turn me down, then I saw you today, and I just said to myself; what the hell, so I went for it, and here we are.”
I said: “When you asked me out, I was shocked, I wasn’t expecting it, a lot of the guys just wanna mock me or tease me, but you sounded so sincere, so here I am.” then I looked up and said: “Can I kiss you?”
He pulled me a little closer and planted his soft lips on mine, he kissed so good, it felt magical, I loved it, we kissed for a long time. Then he asked: “Do you want a drink Rachel, I brought a bottle of dark rum, I like rum, but if you don’t want any, it is okay.” I remembered the feeling I got from being drunk, especially before I got too much, I loved that feeling, and I craved to have that feeling again.
“Sure Tyler, I will have some if you don’t mind.” he reached under the seat and pulled up a bottle of dark rum, he took the lid from it and handed it to me. I took it, thinking of how gentlemanly it was of him to give me the first drink. I took a pretty good swig from the bottle and then passed it back to him. He took a swig as well and then put it on the floor. We looked at each other and again locked in a long kiss, it was passionate, it was wet, it was awesome. Tyler was wearing a pair of shorts, after all it was a nice evening in early summer, my hand fell on his thigh, just above the hem of his shorts, and about six inches below his cock. I knew where my hand was, and I knew I was not going to instigate anything, but I wanted him, and I wanted him badly. I wanted to make sure that he asked me out again, I liked him that much.
He reached down and got the bottle again, we both took swigs from it, and I was beginning to feel the effects. We kissed more and then I finally felt his fingers undoing the buttons on my blouse, I didn’t care, I wanted him to have me, have whatever he wanted, he was so gentle, and when the buttons were all undone I whispered: “Very good Tyler, you did very good.” then I giggled and said: “Let’s have another drink shall we.”
We took more rum, and I started feeling it more, I was almost to the point where I wanted to be, drunk, but happy, not sick, not passing out, but just a happy little girl. I felt Tylers hand go up my back and under my blouse, I knew that he wanted to undo my bra, and I knew I didn’t want to stop him, so I leaned forward to allow him the space he needed to get the job done. My blouse was undone, my bra was undone, and so I looked at him and said: “Would you like me to take them off or are you going to do it?”
He looked at me and said: Go ahead and take them off Rachel, I will get the bottle, he was feeling the effects too, and we were both so happy smiling, laughing, and really enjoying each other. I removed my blouse and then my bra and laid them on the driver’s seat, and there I was at the drive-in; topless.
To read the complete story you need to be logged in:
Log In or
Register for a Free account
(Why register?)
* Allows you 3 stories to read in 24 hours.