Trailer Trash Pt. 07

I hope you enjoy this story. Best understood if you read the proceeding parts. This part of the story is being told by Cherry, Merilee's daughter.

Edited by DRGriffin

Cherry escalates her control of Randy

Well, I'll be darn. In reading Mom's account, I realize that Mom is finding herself, not just becoming a trailer trash slut but also finding her own identity. It is a coincidence that at the same time she is figuring out that she likes being controlled by Jake, I am finding that I like controlling Randy.

You see, Randy and I are becoming an item, and not just sexually. In our case, I was growing as the dominate to Randy. I was also figuring out that it takes a lot of work to be the dominate. It is strange that this extremely smart guy, so commanding at his studies, is so subservient to me in ordinary things. I considered that he put all his energies into his studies and just wanted to be told what to do in the ordinary.

Randy and I had been screwing every chance we got since that first weekend by the pool. As we were both learning about sex together, I took responsibility for the growth in our relationship. It did help to have Sid around. We were talking on a regular basis. She had obviously had a lot of experience in certain areas and was encouraging me to be more adventurous.

She said, "Make him want it so bad he would do anything for you just for your favor."

I said, "Really?"

Sid said, "Yes. The more you control him the more he is going to like it. Don't ask him because he probably doesn't know what he wants. Part of the control is to be more provocative in your dress. Remember how the red bikini worked? Why don't you try Teddy's Specialties? Buy provocative clothes to wear when you are with him. Make him drool. Make him beg. In fact, I am willing put my money where my mouth is. I will call Teddy to authorize a budget for you to spend."

"Oh no! I just can't take anymore from you. That is too generous." After reading Mom's story I realize Sid was playing me. She just couldn't help herself. She had to manipulate the situation. She was turning me into a dominate. But in this case, she was helping her son and me.

Sid smiled a sweet smile, "Think of it as a gift to my son. I am sure he will like this. I also think you should raise the bar on restraints and pain. I saw you spank him. I could also see how turned on that made him. I have other ideas of what he may like. Try making him wear nipple clamps. You may even see if he likes wearing an anal plug while you screw. I am going to make you a grab bag of toys I think you may like."

I was taken aback by this tack but I also wasn't turned off by the idea. Sid sent Melville over the next day with a basket of stuff. I had to research what some of these things were on the internet.

I did go to Teddy's shop. Teddy was a very nice lady who gave me great deals on everything I bought. She also seemed very curious about me. I now know that part of her inquisitiveness was because she remembered Mom and Jake. I think she figured that I was Mom's daughter. At the time, I thought she was just being conscientious.

The weekend Mom was helping Jake with his bid for business I decided to put some of Sid's advice in action. Randy and I would be together most of the weekend, studying for mid-terms. Randy and I had both agreed that we wouldn't let anything get in the way of our studies. We both wanted to be successful and were both driven. I think that was one of the things we liked about each other.

On Saturday morning, I had the weekend planned. I was anxious for several reasons. I had no experience with teasing. I also knew I was running a risk of losing him if I went over the line. But so far it seemed the more dominant I was with him the more he liked it.

Randy and I were going to the library Saturday morning. I wore one of my new outfits from Teddy's. I put on a thong that barely covered my now completely shaved genitals. A very thin red lacey bra. I started to go braless but decided to do that later in the weekend. In this bra, my areolas were still very visible. I had the same areolas as Mom's, small, very red and with nipples that could extend like pencil eraser. My breasts were firmer and stood up more than Mom's and Granbern's but not as large. They were at least G's and I was a full D.

I wore a pair of very tight white short shorts with red knee-high socks that covered my knees and a thin red tank top that barely covered my bra leaving a lot of cleavage. In looking in the mirror, thinking about going in public looking like this, I got excited. You could see the crease of my big ass as the shorts were so short and my nipples were extended because of my excitement. Plus, I could feel the moisture creeping out between my thighs just from the anticipation. The shorts were cutting into my labia.

Just before Randy knocked on the door I almost chicken out of wearing this outfit. I opened the door, hugged Randy and said, "How do you like my outfit?" I made a quick spin. "Is it too much? Do you want me to change? Will it embarrass you if I go to the library dressed like this?" I was talking very fast because of my excitement and fear.

Randy smiled, "You look beautiful. Why would I not like to be with you dressed like that? I hope my few friends see us and are jealous that a hot babe like you would want to be with me. Cherry, I love that outfit. The only problem is I can hardly wait until you will let me see more."

I realized then that Sid was right. I gave him a coy sexy (I hoped) smile and said, "You can look but can't touch. You can show me off but you will pay tonight for my favor." I could see his dick harden in his Dockers from this little teasing. I knew I needed to work harder at the tease. Sid was right. Make him beg.

Randy bowed his head and said, "Yes Miss Cherry. I know I am a bad boy and will need to be punished."

I pinched his ear, "You bad boy. You are thinking about Miss Cherry doing nasty things with you. Aren't you? Tell Miss Cherry the truth."

He answered still looking at the floor, "I am thinking about nasty things. I am thinking about what Miss Cherry will do to me. I can't help it. Miss Cherry is so sexy."

"Okay, behave my bad boy. We must study. I expect you and I to ace our mid-terms. Now let's go."

We went to the Student Union for lunch before the library. I got a lot of attention from the other students. I felt self-conscious about the attention I was getting but Randy beamed with pride. I was even beginning to think I was his hot girlfriend. I observed that I wasn't the only girl in the Union wearing an outfit that showed off the female anatomy. In reality, I was only about in the middle of the pack. One girl had ass cheeks hanging out and no bra with a tank top showing off a small set of perky tits. I decided next time no bra.

We then went to the library and really did study.

With an armload of books, I bent to sit them on the desk as he sat across from me. I caught him looking at my ample bosom. I bent over the desk to whisper in his ear, again showing a lot of breast to him, "I know that you are being a bad boy. You are having nasty thoughts about Miss Cherry. Aren't you?"

Randy looked up and grinned, "I can't deny it Miss Cherry. Miss Cherry is so sexy, I can't help myself."

We actually did for the most part study all afternoon. I got up to use the toilet and I glanced back to catch Randy watching my big round buns fight to stay in my short white shorts. When I got back I sat next to him, laid his hand at the top of my thigh and whispered to him, "You like Miss Cherry big round buns. Don't you?"

"Yes, Miss Cherry I had such nasty thoughts watching you walk to the restroom."

"We need to make good grades so I am going to make you a deal. Study real hard for the next hour and Miss Cherry will give you a reward." I slipped my hands between his legs and felt his penis had grown to its full length. I knew he was hurting. I nibbled his ear as I whispered, "I will take care of that for you."

He smiled big and his hand slipped to touch my shorts, "I will work real hard for Miss Cherry to earn my reward."

I moved back to the other side of the table and we did work hard for the next hour. It was now close to six and I wanted to eat. I closed my books, packed my back pack, and said to Randy who had been watching me closely, "Follow me."

I lead him to a unisex restroom. There was no one around as we both slipped in and I locked the door.

I said, "You have been very good the last hour so you have a reward coming."

"Thank you, Miss Cherry."

"First I am going to show you my bra but you can't touch."

I pulled the tank straps off my shoulder and pushed the material to my waist. My tits were barely contained in the thin lacy material of the bra. I reached up and pinched both nipples to make them stand up. "Do you like my bra?"

"Yes, Miss Cherry, I love your hard nipples. May I touch them?"

"You may touch the bra but not inside."

As he rubbed my tits through the bra, I unbuckled his belt and pulled his pants down to let them drop to his feet. I felt his penis with his boxers still on. I felt a nice hard long dick ready to be taken.

"Oh my, I think you are ready for your reward. Miss Cherry has been doing research on how to give a blow job. Would you like for Miss Cherry to give you your first blow job?"

He stopped breathing for a beat, I felt his penis take all the blood from his heart, as he said, "I am not worthy but it would be a great reward."

I continued to rub his penis as he rubbed my bra and breasts. I was so close to an orgasm myself just from the dialogue and him squeezing my jugs. I said, "Funny thing, your mother gave me instructions on how to give a blow job. Your mother is very knowledgeable about sex and has given me several suggestions."

I couldn't decide how this affected Randy but it certainly didn't turn him off.

I said, "I want you to tell me how to do this better when I am finished. That is your job."

He said, "Yes, Miss Cherry."

I gave him a deep kiss while he continued to massage my breasts as I slipped his very brief briefs to the floor and stroked his hard-straining penis. I dropped to my knees, stroked his pretty penis, kissed up and down all sides and then focused on the tip. He was moaning. The pre-cum had started.

I said, "I love the salty taste of your pre-cum." I only knew this was what was happening because Sid had told me about it. I gently took the tip into my mouth and flipped my tongue around the tip. I let my tongue explore every aspect of his tip as I gently stroked the shaft. I knew he wouldn't last long if I did much more than a gentle stroke. He had a hand on the wall to help him stay upright.

I placed my hands on either side of his hips and slowly allowed his shaft to enter my mouth. I didn't think I could get it all and decided not to try. Sid had instructed me to be patient, get used to the feel of a dick in my throat and avoid gagging. She had told me my throat had to get accustomed to having something going down it. Each move in and out I let him get only as far as I was comfortable. It seemed like I found the spot that was right. I felt with my hand to find that I had all but about two inches down my throat.

I kept one hand on his hip to control the depth and with the other I unzipped my shorts, slipped my hand into my thong and found my extended clit. I had an immediate orgasm. This seemed to relax me even more about what I was doing. With that relaxation and that I had my release, I started picking up my pace.

Randy said, "Oh, Miss Cherry, that feels so good. You are too nice to your nasty boy."

This just spurred me on, I picked up the pace to as fast as I thought I could go without gagging. I felt his penis get just a little larger in my mouth. I wanted to taste his cum. I pushed harder on my elongated clit and had my second orgasm as he started squirting into my mouth. Since I had never done this before I completely mistimed my stroke so very little of his first gush of fluids went in my mouth. It streamed down my chin, onto my chest and I could feel it getting my lacy bra wet.

I did manage to time the second and third eruptions and swallowed that. I liked the salty taste of him. I pushed him as far in as I could as he finished and sucked real hard like I wanted all of it.

I licked him clean, got on my feet, and said, "You really are a nasty boy. Lick your jizzum off Miss Cherry." I kissed him deeply. He then licked my chin and chest clean of his jizzum.

I hugged him and whispered, "How was your reward?"

"It was great. I can't believe you knew how to do that."

I said back, "Thank your mother. Do you mind if I discussed this with her?"

"Not at all. I know Mom is very experienced. She thinks I don't know about what she and Rod do, but I do. I am glad you two are getting close but be careful."

I said, "We need to talk about that some time but not today. I also know you need to get to know my mother." I gave him a sexy smile, "You are still going to get your punishment tonight. Look you got your stuff all over my bra."

"I am sorry Miss Cherry."

There was a knock on the door and a male said, "Hey, what is going on in there?"

Randy said loudly, "Just a minute." Then he said softly to me, "I will take care of this while you get situated."

I said, "Okay."

He slipped out the door. I heard him say, "Sorry but my sister got sick. It doesn't smell so good in there and she is going to need a few more minutes to get cleaned up. You may want to try the restroom around the corner."

The male said, "Fine. I hope she is alright."

Randy knocked on the door and said, "I am going to get my stuff. See you out front."

I said, "Okay."

I removed my bra, put it in my backpack, pulled the tank top back in place and looked in the mirror. While it was clear that I wasn't wearing a bra, my nipples were making themselves seen, it still wasn't completely out of line to be walking around like this. I thought Randy would like it.

Randy was waiting for me with his backpack, took mine and we walked out of the library.

Randy said as we walked to the car staring at my braless shirt, "Miss Cherry, I am having such nasty thoughts. Your breasts are so pretty bouncing up and down as you walk. I just love them."

"You have such a dirty mind. You got my bra wet and it was uncomfortable. It is your fault I have to go without a bra. Would it embarrass you to be seen with me like this at Tony's Deli? I need to watch my weight and would like a salad. Another pound and I won't be able to wear these new shorts."

Randy smiled, "I would be happy to take you to Tony's just as you are. You are the hottest girl on campus. Plus, you have new skills. That is my first and only blow job but I don't think it could have been any better."

"Thank you, Randy. I will get better."

Randy gave a big grin. We were driving to Tony's as we talked. "So, you are going to do it again? It didn't gross you out."

"Oh no. I liked doing it very much. Your penis feels very good in my mouth and you taste so good. I like cum. Next time I will catch more."

Randy said, "I will be a good boy so Miss Cherry will give me a reward."

We sat at a small round table to eat dinner. I couldn't help but give everyone a nice view of the top half of my breasts, some side boob and outline of nipples that were hard pebbles. Randy and every male kept watching me.

As we ate Randy asked, "So you and Mom are becoming friends?"

"I think so. I think she likes me. She has given me a lot of advice about sex. I know I should be talking to my mother but I think yours has far more experience." Little did I know this was changing so quickly.

Randy said, "She does but never discussed it with me. She did her best but Mom is different. Grandfather had a couple take care of me as a little baby and then Mom hired a male tutor that worked with me until I was about twelve. Then she sent me to a school for special kids. It was a little lonely and I did miss home. But I know she has wanted the best for me."

I wanted to cry but managed to say, "Randy, she loves you very much. She wanted you even though she was so young at the time. She is very different. My Mom is normal." Well I thought she was anyway.

"I know Mom loves me. I like that you and she are becoming friends. So far, her advice has been exactly right. You are doing things I wouldn't know I liked but do. I mean, it is exciting me so much to see your breasts like this. I am getting so turned on again. I would do anything to touch you."

I gave him a sexy smile, "You are already in trouble. I will have to make the punishment worst because I can see you are letting that thing in your pants expand."

He whined, "You are so sexy."

We finished dinner and headed back to the guest house.

As we closed the door, I said, "Time for my naughty boy to be punished. Take off your clothes and get Miss Cherry a glass of white wine."

Randy removed his clothes while I watched. His penis was already at standing up. As he went to the kitchen to open the wine, I got the toys I planned to use which Sid had given me. I hid them under a towel.

Randy handed me the wine. I took a big gulp of wine, kissed him on the cheek, took his now fully erect penis in my hand and said, "This is now mine and for my pleasure. I am going to use it any way that pleases me. First thing is your punishment."

I struggled to get out of tight white short shorts, leaving only a red thong to go with the braless red tank top. Randy stared at my near naked bottom.

I did a circle and said, "Look but you can't touch. Yet!" I turned my naked ass to him and said, "Is it as good as your dirty thoughts have been all day?"

Randy said, "No it is much better. Can I kiss it? Please Miss Cherry let me kiss it."

"Admit that you have had nasty thought about my ass and you need to be punished."

"My thoughts have been consumed with thoughts of your wonderful body. Please let me kiss it and make me hurt for being such a bad boy."

"Ok, you can kiss my ass but you can't touch it with your hands."

I jutted my ass out with a slight bend at the waist as his lips touched my right cheek. He kissed my fleshy buns until I said, "Time for your punishment."

I reached under the towel and pulled out a twelve-inch leather paddle. I said, "Grab the arms of the chair and tell Miss Cherry why you are being punished."

He grabbed the chair which made him stick his ass out for me to hit with the paddle. He said, "I have had fantasies about Miss Cherry's body. I thought about her being naked, sticking my dick in her beautiful pussy, touching her full beautiful breasts and feeling her luscious round ass cheeks. I wanted to suck on her beautiful pussy. I fantasized even about Miss Cherry spanking me and making me do things."

I said, "How many licks do you desire?"

"Whatever Miss Cherry thinks."

"Count and ask me for another."

Whack, Randy said, "One, may I have another Miss Cherry?"

Whack, Randy said, "Two, may I have another Miss Cherry?"

Whack, Randy said, "Three, may I have another Miss Cherry?"

With that one I reached around, squeezed his rock-hard penis and said, "This boy seems to think for you. But you know I love it, don't you?"

Randy said, "Yes mam, I know. I want more. Please."

Whack, Randy said, "Four, may I have another Miss Cherry?"

Then continued until, "Ten, may I have another Miss Cherry?"

I said, "No that is enough for that. I have another way to punish you." Now stand up and place your hands behind you.

I got the handcuffs Sid had given to me and handcuffed his hands behind him. I said, "Now sit on the couch. You don't get to touch me until I am ready. I am going to pleasure myself while you watch."