Shoplifting Has Its Consequences
Copyright© 2025 by Rachel 42
Chapter 18
True Story Sex Story: Chapter 18 - 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
The new school year was approaching, it was 1969, I would be turning sixteen in less than two months and starting the eleventh grade. This year was going to be different; I would be going back to school with a nice wardrobe, and my confidence in myself and my body was better than it had ever been. A lot of my schoolmates knew I didn’t wear falsies by now, and those that didn’t, would find out soon enough, I was determined to make sure that the clothes that I chose to go back to school in showed enough cleavage, my tops would make it obvious that my boobs were real.
Mom and I had decided that we would go to the big city tonight, turn some tricks, and then do my shopping tomorrow. I was excited about the shopping trip, I had planned on spending a lot of money on blouses, skirts, bras and maybe even a dress. Mom’s rent was due again, so she needed some extra money for that, and she was also going to add to her wardrobe. We would have a good time together.
We left home in the afternoon, and we went to a Holiday Inn and reserved a nice room for ourselves. We had a light lunch late in the afternoon, then went up to the room to change into our slut gear, as we liked to call it. When we were satisfied with how we looked, we went to work.
It was a good night for us both, we made a lot of money doing our normal things, a few blowjobs, half and half with a couple of guys, some guys just wanted to fuck. We worked all night and went into the early hours of the next morning before packing it in.
The one trick I turned that I remember so well was with a younger guy, probably in his late twenties that sat next to me and told me his story before paying for a blowjob followed by a piece of tail. He told me that his wife had come home about a week ago and told him that she was leaving him for another man, a man that she had been fucking for several months. He was devastated by what she had told him, and he cried as she packed her things, and he watched her walk out the door. He then said that he needed to have sex with a girl to help him get on with his life, and that is why he flagged me down.
He talked as I was sucking his cock, telling me that I was only the second woman to ever suck his cock, and that other was his wife, he had never had sex with anyone else. I got him so hard so quickly that he couldn’t wait to go from getting his cock sucked to sticking it in me. Once inside of me, he didn’t last very long at all, I hope he felt that he got his hundred bucks worth. The other thing that I remember from the night was a man that offered me a hundred and fifty for anal sex, of course I turned him down. I am not really sure why, but I think I just wanted my first anal experience to be with someone I knew.
Mom and I hit the stores in the morning to get our shopping done. It was such a fun time, I found the tops I wanted, a couple of skirts, and even a nice dress. The trickiest part was finding bras that fit my boobs; they had grown, and the bras I had were getting tight, so I was quite shocked to find that I was now wearing a 42DD size bra. I bought three nice bras; they were quite expensive. I spent something like five dollars each for the bras, about the same for three blouses, I bought three skirts for about the same and I paid about eight dollars for the dress. My shopping spree had cost me about sixty dollars with the tax included. I had earned just over five hundred dollars the night before.
Mom also bought a few things for herself, and for the first time, I was going to be handing over a couple of my nicer bras that I had grown out of to my mom.
Later that day, I treated mom to a nice lunch at a very nice restaurant in town. We sat and talked for a long time. She asked about Bob’s family and how they seemed to be taking up a lot of my time, I told her how nice they were, how we had engaged sexually, and how they indicated it would be nice if she would come to their place for an evening of swimming or just to meet them.
Another topic was my boobs, and how I was always being mocked or made fun of because of the size of them, I told her that I was going to school this year with an entirely different attitude about my tits. If they want to mock me, go ahead, but I have something that all the guys wanted, and I was going to use that in my favor somehow.
We talked about Roger and how he was getting to be increasingly interested in sex. I asked mom if he had wanted sex from her anymore since the one time I knew about. She told me that he hadn’t but was paying a lot more attention to her body than he had in the past. She also said that she knew he had quite a collection of men’s magazines stashed away in his room. I told mom that at one time he brought one of his magazines out and showed me how some of the girls had shaved pussies and asked why I didn’t do it. I told mom that and she just laughed about it. Mom said that she was aware that some women liked to shave, but it wasn’t something that she was into, not yet at least.
After lunch, we hopped into mom’s car and headed home. The drive took about an hour, and we had some more good conversations on the way home. Mom confided in me that she had dated a nice guy about four or five times now, and that they were getting a bit serious about each other. I liked hearing that. I wondered when I might meet this guy.
Later that afternoon, I met up with Laura and we decided to meet in the morning and walk to school together, I told her about my trip into the big city and my shopping trip, I was excited to finally be able to wear nice clothes to school and not feel inferior to the other girls because of my wardrobe.
The first day of school came, Laura and I met up and walked to school together, I had on a sleeveless white blouse that showed a good portion of my cleavage, a short black skirt, and I was wearing a black bra and panties under my clothes. I felt good and when I arrived at school, I was getting looks from both boys and girls. Of course, there were those that chose to tease me about the size of my boobs, but I didn’t care. I had what I had, and if some of the other students wanted to be jealous or tease me, then so be it, I had gotten to the point where I just didn’t want to let it bother me anymore.
The first week of school went fine, I had made a couple of new friends, and we were hanging out together, I was still spending time at Bob’s house, but at least now I had some friends that accepted me for who I was. However, there were still those that looked at me and treated me like I was a freak of some sort.
Laura came to me one day and said that the school was holding tryouts for the grade eleven volleyball team and that we should try out. I had played volleyball during gym classes and at noon hour, and I did enjoy the game, however I had one big disadvantage, or should I say, I had two huge disadvantages. I wasn’t overly tall, but I was tall enough. Volleyball isn’t a game made for short people; however, my boobs flopped around a lot with all the movements in the game, and I was constantly putting my boobs back into my bra properly. Laura, however, convinced me that we should try out for the team, and the tryouts started after school the next day.
The night before the tryouts, I was with Bob at his house, and I told him about the volleyball tryouts. He was excited for me and thought it was a good idea. I told him how I felt about my boobs being a problem, and he was sympathetic about it, but thought that it would be good for me to be with the other girls and maybe make some more friends of the same sex. Bob was always so good to me, and I soaked up his encouragement.
Bob looked at me that night and said: “You know Rachel, I would feel the same way about you, as I do now even if you had no boobs at all, I really admire you for you, not your big tits.” I liked hearing that, and I believed him; he was a good friend. He wasn’t always trying to get in my pants either, but I knew he wanted to.
I answered him: “I know Bob, you have always been such a great friend, you and your parents have helped me feel better about myself.” Bob and I had a long talk that evening about school and how some of the kids still teased me, but how it seemed to be getting better, we talked and didn’t engage in any sexual activity at all, I liked that Bob was able to treat me that way. In fact, it had been almost two weeks since Bob and I had any type of sex together.
After school the next day, Laura and I went down to the gym together to attend the volleyball tryouts. I expected that the team would consist of about thirteen to fifteen players. There were about twenty-five girls that were trying out.
Laura and I sat next to each other in the change room, and I looked around the room to see who was all there trying to make the team. Therre were some girls that I considered shoo-ins to make the team, both because of their reputations as good athletes and their height, at the same time there were a couple of overweight short girls that I didn’t think had much chance of making it. I felt that I had a chance to make it, but would really have to play well, and somehow find a way to work around this big boob problem I had. Of course, I did notice some of the girls staring at my boobs, especially as I sat on the bench in my bra and panties.
When you are in a locker room with twenty-five other girls, and they are all sitting around in their bras and panties waiting for the team coaches to bring our practice uniforms, you realize that not all girls were created the same. More girls had bigger boobs now that I had reached eleventh grade, just not as big as mine. There were still some that were extremely flat chested; they would have an easier time playing this game than I would.
The coaches arrived and handed out the practice uniforms, and gave us instructions on what to expect, and how we would be practicing. I was quite excited, I liked playing this game, and I wanted to make the team. I pulled on the tight shorts and the top that clearly showed off the stomachs of all the girls, I don’t think that the two overweight girls with big stomachs liked them much, but like me, when you’re not the same as everyone else, you need to accept it.
We all went up to the gym from the locker room and started out just hitting the ball back and forth to each other, nothing too strenuous yet, but after a while we began doing drills that included jumping and moving quickly to the left and then to the right. That is when I began having boob problems, they didn’t want to stay in one place in my bra, and in fact popped out of my bra a couple of times. This was a time before the advent of sports bras, so there really wasn’t much I could do about it. Our practice lasted about an hour and a half, then we went back to the locker room where we showered and changed back into our street clothes.
I no longer hid or tried to avoid anyone seeing me naked in the change room, I took everything off and walked over and got under one of the showers and had my shower as if I owned the place. I noticed a few girls look at me, but I didn’t hear anyone mock me or tease me about the size of my boobs, I found that to be a good feeling.
Our practices went on for a few weeks, and then after two weeks of practice, the coaches made six cuts and then were going to make six more in a week. I survived the first round of cuts, and I thought I could have a decent chance of surviving the second round as well, but I wasn’t confident that I would be a starter on the team. There were some really good players on our team.
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