Shoplifting Has Its Consequences
Copyright© 2025 by Rachel 42
Chapter 23: More Entertainment for the Team
True Story Sex Story: Chapter 23: More Entertainment for the Team - 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
Laura and I were ready to make some good money giving the boys from Bob’s football team a sexy show, and to be honest, Laura, a little more than me, was looking forward to making out with me. It wasn’t that I minded; it was just that this was strictly about making money, but if it looked realistic, it would be a much better show.
Laura had a little trouble getting over the breakup with her boyfriend, Norm, but she was young and I had been encouraging her to get over it and move on, but now she was showing that interest in me. It wasn’t that I minded of course, I had already had lesbian experience with my mom and with Jean, so why not, it was just going to be business for me.
Later that afternoon, the day before we would be doing our show, I ran into one of the boys from the football team. I was walking down by the river when he and I met on the pathway. His name is Kelvin. He stopped me and we talked for a while; he was one of the boys that had taken part in my gangbang. He said that he was planning on watching Laura and I performing for them and questioned me about being bisexual.
I told him a little lie and said that Laura and I would both be doing it for the first time. We didn’t really think we were bisexual and that we just wanted to earn some money by giving the boys a show.
He then shifted his questioning to my relationship with Bob. I told him that Bob, and I were just good friends, to which he replied: “Friends with benefits?”
I smiled and answered: “I guess you could say that.”
Kelvin was bold with his questioning; he was a confident guy, very good looking and built solid. He was already over six feet tall and weighed about one hundred and eighty pounds. He had longer blond hair, and sexy blue eyes. He was very attractive. Then he asked: “So tell me Rachel, what else do you do for money?”
I looked at him, knowing that he had probably figured out or been told that I was no stranger to prostitution, I wondered how to answer his question, then I just blurted it out: “Well Kelvin, let’s put it this way, if you want me, it’ll cost you fifty bucks.”
Kelvin grinned, but he wasn’t surprised, and asked: “And what does fifty bucks get me, Rachel?”
I answered him with a question: “Well maybe I should ask you what it is that you want.”
Kelvin was now getting serious: “I want to take you down stream and into the woods, I want to see you get undressed for me, I want to see and play with those huge tits of yours, and then fuck you in private instead of in front of a bunch of guys like the other night.”
Having heard what he wanted, I answered: “I can do that for fifty bucks.”
Kelvin was a little shocked but anticipated the excitement, and he said: “Okay Rachel, let’s go.”
I was total business for a few seconds when I responded: “Fifty bucks Kelvin.” as I held out my hand.
He pulled out his wallet and paid me with no questions asked, and we walked down the path about a hundred yards and then went in behind some trees, where we could have some privacy. He sat on a stump and watched as I looked at him with a smile and said: “Enjoy Kelvin.” Then I began slowly stripping off my clothing. First was my top, then my jeans. I stood in front of him in my underwear for a minute or so before moving on to remove the rest of my intimates.
Even though he had seen me naked before, he was looking at me and enjoying what I was doing like he hadn’t seen me naked before. I took off my bra and then my panties and stood in front of him totally nude. He got up from the stump, and walked towards me, his hands went right for my boobs, I allowed him to play with them for a while and then his hands fell to my hairy bush. I was surprised that he was as gentle as he was; he really seemed to appreciate what I was giving him.
As I stood there, I felt his finger enter my hole, it felt good, I liked it and I liked how he was being as gentle and caring as he was. I had to tell him that it felt good. Then I said that he should probably take his clothes off, too. He did as I suggested, and we were together naked, and now laying on the leaves behind a tree, somehow it felt romantic, and I had to remind myself that this was business. Just let the guy fuck you and get it over with. But I liked it, and I couldn’t help it. I didn’t want to rush it, I wanted it to last, I wanted his cock, and I wanted it deep inside of me.
We laid on the ground, in the leaves; he held me. He cuddled me, and he held me so close. We kissed, and it felt so good, what the hell was happening. He had turned me on, and it was supposed to be the other way around; that was my job. I felt his warm hands on my tits, again he was so gentle, it felt good to have my boobs played with like this, then his mouth was on them, he kissed them and began to suck on my nipple, I loved it. We took several minutes doing this and then I felt his finger moving through the hair on my twat, again it was so relaxing, he was making everything so easy, so natural, he was good, so fucking good to me.
He whispered into my ear: “Suck my cock Rachel, I would love it if you would suck my cock.” I didn’t hesitate; I went down on him and took his cock into my mouth. I held it in one hand as I licked the sides of his hard dick and occasionally took it deep into my throat. I sucked his cock, I licked his cock, and I fondled his balls until he couldn’t wait any longer, he rolled me onto my back, and gently spread my legs, he had a good-sized cock, not overly big, but a good size. I felt it slowly enter the hole that he wanted.
I couldn’t help saying: “Fuck me Kelvin, fuck me babe, fuck me like the dirty fucking whore I am.” He did just as I asked, but he was slow, he made every stroke of his cock feel so good. I laid back, and rocking slowly with him, we made love for several minutes, and then he stiffened up, and I knew he was close, and so was I. “Fuck me Kelvin, go faster and make me cum with you, fuck me babe, fuck me faster.” Kelvin sped up and within a few seconds we were both having a wonderful orgasm, mine was dribbling down my legs, and his was overflowing out of my cunt hole. We laid together, naked for a long time, he knew that he had turned me on, something that rarely happened, for once I wasn’t the one turning a guy on, he had me so horny and so turned on, I felt guilty about taking his money.
So, I told him: “That was so good Kelvin, I feel a little guilty about taking your money, but then again, you got a real nice piece of tail and I got laid.”
Kelvin then asked: “Do me a favor Rachel, let’s not tell anyone about you charging me for tail, let’s just keep it between you and me, and by the way, I would pay you again if you don’t mind doing me again.”
I answered: “Any time Kelvin, anytime.” then after a minute or so I asked: “Are you one of the guys that will be watching Laura and I tomorrow night?”
Kelvin answered: “I wouldn’t miss it Rachel, wouldn’t miss it for the world.”
I smiled and got up to get dressed, then looked at Kelvin and asked: “Do you want my panties Kelvin, it seems to be what guys want these days.”
Kelvin smiled and said: “Yes, that would be nice, thank you Rachel.”
I gave Kelvin the panties I had been wearing and then pulled another pair out of my purse and got dressed, I had started carrying an extra pair because of how often guys wanted my panties. We finished getting dressed and then Kelvin took my hand and walked me back out of the woods. It was an unexpectedly good day.
Once we got back to the road, Kelvin asked if he could kiss me, I agreed and leaned into me and gave me a nice kiss with his arms around me, he was a guy that I had a great deal of respect for, just because of the things he would say and because of his gentleness. After that kiss, we went our separate ways.
Later that afternoon, I met up with Laura, and she told me that she had second thoughts about doing the show in front of all those guys. It was going to be something she had never done before, and she was getting cold feet.
I looked at her and said: “Well Laura, Bob has put a lot of time and effort into setting this up for us, but if you don’t want to do it with me, then that’s okay, you don’t have to. I will give the guys a solo show.
Laura hung her head and answered: “Rachel, you know I want to be with you, it’s just that I feel intimidated in front of a lot of guys, what will they think of us?”
I answered: “Look Laura, think of it this way, what will people think of them for paying so much money to watch a couple of chicks play with each other.”
It didn’t take much talking before Laura agreed to go ahead with the performance that evening; she had never done anything sexual with any more than one guy, and she wanted me, more than I knew at that time.
I left Laura and met up with Bob the next day. We talked a little about that night’s performance, and I assured him that all was good to go. He told me that he had pretty much the same group of poor little rich kids that he had last time. One of them had backed out, but there would be several guys watching, and that he had collected four hundred dollars for Laura and I to split. To me, that was good money for a show that wouldn’t last much more than half an hour.
I left Bob, and met with Laura again, and told her to remember to bring any sex toys that she had, and that’s when she told me that she didn’t own any sex toys, so i told her that I would bring the ones that I had previously purchased when I was in the big city.
I left Laura and went home to my mom’s house. She had prepared dinner, and we sat and enjoyed a nice few hours together. We talked about a few things, and she told me that she had a date that night and wasn’t sure if she would be home or not. It would depend on whether he took her to a motel or if they came back to our house. I knew he was a married man, so he wouldn’t be taking her to his house.
I went into the bedroom and packed my sex toys and some lingerie into a small bag and came out and said to mom: “Have fun tonight mom, I will see you tomorrow.” Then I walked out the door and went directly to the motel where Bob would be waiting.
When I arrived, Laura was already there, I told Bob that his teammates would all have to wait outside until Laura, and I were ready for them. We would go inside, change into our lingerie, and prepare for our little show. Once Bob collected all the money, they could come inside, and we would do our thing.
Laura and I went inside, and we closed the door behind us. We made sure that the blinds were closed as we both took a chair and discussed what we were going to do. The plan was set, and we both undressed completely, and then put our lingerie on. Laura looked good, she had a sexy little baby doll top that was pink and didn’t hide very much of her firm boobs, her panties were also a matching pink and were also see-thru.
I was wearing a longer top that fell below my ass cheeks, it was also see-thru and matched my blue panties. My huge boobs were very visible.
Once the group had all arrived, Bob entered the motel room, handed me the money and said that the guys were ready. I told him to tell them to come in and to remember that there would be no touching either of us. This is a show, and that is all it is.
The group came into the room, eight of them and Bob; they all stood at the end of the bed against the wall. Once they were all in place, Laura and I were ready to start our show. This show would be totally spontaneous, no rehearsals, no planning, just do what was to come naturally.