Shoplifting Has Its Consequences
Copyright© 2025 by Rachel 42
Chapter 8: Another Day
True Story Sex Story: Chapter 8: Another Day - 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 next day I went to school and as I was getting my things from my locker, I was approached by Bob. I assumed that when I saw him coming towards me that he wanted me again, and of course that would have been just fine with me. So, when he got to me, I asked: “When do you want me, Bob?”
Bob surprised me by saying, well that’s not what I need to say right now, but sure, we will get together again one day next week okay. But really I want to make sure that you don’t say anything to anyone about what we have done together, I don’t want it getting back to my girlfriend, I know I can’t control what my friends and I did that day with you, but as for yesterday, can we just keep that as our own secret?”
I assured him that I wouldn’t let on about what we did, it was our naughty little secret, but then I asked him: “Bob, what do the other boys say about me, do they call me names, do they ever say anything nice about me?”
Bob was hesitant in his answer, but then said: “Well Rachel, some of the guys that think that you have fucked some of the guys, well sometimes I have heard them refer to you as a slut, but other guys say how sexy your tits are, and how much they would love to see them or touch them, I’ve heard some guys say you have a nice ass. Rachel, I think you’re a nice girl, and I have loved the time we have had together, so I just think you are such a hottie, such a nice girl, and I really thank you for yesterday.”
It was Friday morning and mom said she was going to take me to the city this afternoon, I was looking forward to it for a couple of reasons. First, I had a bunch of money, and I wanted to buy some new clothes, and second, mom had talked about selling sex on the street. I was curious to see how that worked and if guys would actually want to pay me for sex.
To get into the city and have time to do some shopping first, I was only going to school until noon, and then I would go home, and mom and I would go into the city together. I was looking forward to it.
When I got home just after noon, mom was sitting at the kitchen table waiting for me, I couldn’t believe how sexy she looked. She was braless, her tits were easily visible through the while tank top she was wearing, and her skirt was only a couple of inches above her pussy. I had seen mom topless before and I had seen her braless, but that top she was wearing was sheer material, and her boobs looked spectacular. If she had put that on to attract men, I think she was going to do alright.
I didn’t have anything like that to wear, but I could find something in the city when we got there. I just wore the skirt and blouse that I had worn to school, along with my new black bra and a pair of silky red panties that once belonged to Bob’s mother.
Going to the city to turn tricks never made me feel like a prostitute. Instead, it was just a way for mom and me to make some money. It was the same way I felt with the boys, I just wanted to make a little extra money. I never considered myself a prostitute. This was something that didn’t happen a lot, it wasn’t like mom, or I were regular street hookers. I don’t think mom had done this very often in the past, and it wasn’t something that either of us did again more than a few times.
We got into the city, and we went to a few places to do some shopping, I found things that I had never dreamed of. I bought a package of panties, seven pairs, all different colors and each had a day of the week printed on them, I thought they were so cute. I bought 2 skirts, both quite short, and one of them was black imitation leather, I would wear that one tonight. I also spent money on a few tops, including a black almost see thru sheer material. It was very sexy and would go with my skirt.
Mom had told me a few things to keep in mind, she told me how much to charge the guys, and a few other hints and things to keep in mind. I changed into the outfit I was going to wear that night. I had my black bra under the sheer black top, but mom said it would be easier not to wear a bra, and with my rack being as big and desirable as it was, it would make guys want me a little more. I decided to go braless, and this wasn’t something that I did very often when I was out.
As we got to where we would be hanging out, I noticed a lot of the other girls standing on various street corners’, some were real pretty girls, some were older, and the thing that stood out the most was how some of them were dressed. There were chicks there that were nearly topless, more of their boobs were hanging out of their tops than were covered. There were a few that appeared to be in their panties. I felt a little intimidated at first, but mom was supportive and just told me to try to stay away from them and not to get involved in any conflicts with them.
Mom parked the car in a parking lot beside where she said we would be working that night. She explained how easy it really was. I wouldn’t have to do anything; the men would come to me. Mom was right, and it didn’t take long at all before the first man came to me. He pulled his car over and asked me how much I wanted for a blowjob. Mom had told me to ask for forty bucks for a blowjob, sixty for a lay, and eighty for a little of both. I answered him with what mom had suggested and told him it would be forty bucks. He agreed and told me to get into his car. I got in, and he pulled around the corner and into the same parking lot that mom had parked in.
That day mom had finally been able to get me on the pill, so I didn’t have to use condoms anymore, however mom told me that if a guy wanted to go bareback, that I could get more money out of him, usually another ten or twenty bucks.
After the guy had parked his car in a dark corner of the parking lot, he turned to me and asked: “I’ll give you fifty if you get topless and let me see and feel your tits while you blow me.”
I answered him professionally: “Okay, can I have the money now please.” he opened his wallet, took out a couple of twenty-dollar bills and a ten and handed them to me. I tucked the money into my panties and then asked him to undo his pants. I pulled the top I was wearing over my head, exposing my braless tits.
He undid his pants, and pulled them down, he reached for my boobs and began playing with them, I then went down on his cock in the front seat of the car. This was the late in the 1960’s, and the front seat of the cars was a lot different than it is today. I could easily rest my head on his lap while giving this guy a blowjob.
This was my first trick, but it didn’t feel any different to me than doing this with a boy at school, it didn’t feel any different even if I didn’t do it for money.
I asked him to put his condom on, and he did as I asked, and this was the first time I had ever sucked a cock that had a condom on it. I stroked his cock as I sucked on it and felt him feeling me up, he was gentle and seemed like a nice man. I would say he was in his forty’s, but he was nice. I sucked his cock for several minutes before he started showing signs of getting close.
After a few more strokes of my hand and some up and down on his stiff cock, he began to cum. He moaned in delight, and I knew that I had done a good job on his cock. I sat up, and reached for my top, I pulled it back on, looked over at him, and then I said goodbye as I opened his car door and got out and walked away. I stopped at mom’s car and put the money I had just made away.
As I walked back over to the corner, I noticed that mom was gone, I smiled to myself knowing that mom was busy earning money too, I smiled knowing how easily I had made that fifty bucks. I thought to myself: Who’s next.
I got back to my corner; I stood waiting for about ten minutes when another man stopped and asked what I charged. I told him my prices, and he offered me less to give him half and half, a partial blowjob and he would finish by fucking me. I turned him down. He drove away, saying he could get it from someone else. I felt good about saying no, I didn’t want men that were going to act like that, I had the goods to sell, and I was proud of them. I had no intention of going with him for less money.
It wasn’t long before another car stopped, this time the guy said will you suck my cock and then let me fuck you for a hundred bucks. This was more than I was going to charge, I answered him with a yes, and got into his car. We drove away to a dark back alley a few blocks away. As we were driving, I noticed a babies car seat in the back, and I wondered if that meant that he had a wife and small child at home.
We stopped and he turned the car off, I asked how he wanted it to go, and he bluntly told me what he expected. “I want you to get undressed, then I want you to suck my cock, get it nice and hard, and then ride me until I cum, I will sit on the passenger side, and you can get on me., and fuck me that way.”
I agreed, then asked for the money, which he handed over to me, I put it away, and took my blouse off, then my skirt and panties, as I disrobed for him, he was doing the same. Once we were both naked, I leaned over and placed his condom over his cock, I began sucking on it, this guy had a big cock, probably the biggest I had ever had at that time. I sucked him and played with his balls, and he got hard quickly, I kept giving him the head he wanted, playing with his balls and stroking his hardon.
He told me that he was ready to fuck me, He quickly changed places with me, he got in the passenger seat, and I climbed on him and straddled his cock. I lowered my pussy onto his cock and slowly bounced up and down on it. He played with my boobs as they bounced in front of his face. Then he commented: “You have such big and beautiful tits, I like that.” I managed to say: Thank you, enjoy them.” as I continued riding his cock.
Again, I noticed the car seat in the back seat as I rode his cock, but I didn’t ask anything about it, I just let my imagination tell me the story. He whispered that he wasn’t far from cumming. That encouraged me to tighten the grip of my pussy as much as I could and ride him a little faster, then he told me that he was cumming, and how good it felt.
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