Trailer Trash Pt. 08

I hope you enjoy this story. Most of this is told by Merilee but watch for the change to Cherry's voice. Really need to read the preceding parts to understand the storyline.

Edited by DRGriffin

Jake has Mark punish me

I awoke Monday morning, sore from being screwed in all my holes over the weekend by Jake and his son Josh. I was glad that Jake had given me a couple of days to heal up from the sex marathon. He had me on the normal routine with the exception I didn't have to diddle myself after exercise.

With my exercise routine, I was really in shape. Twice a week, I was running six miles. Every other day I ran three miles. On most days, I did calisthenics on my front patio then ran almost two miles to a park Jake had shown me, used the exercise stations set up in the park and ran back home. In total, it took me an hour or more every day. I was in so much better shape and my ass was considerably larger but firm and my stomach was flat.

Mark joined me on the days he didn't have to do breakfast at the shelter. He was getting in better shape also but couldn't keep up with me. I usually left him behind on the runs but he would catch up while I was doing the park stations. I also had accumulated an audience. Particularly in the park. It was routine to have several men waiting for me at the stations.

On Tuesday morning, my body was healed and my twat was beginning to rebel against my abstinence. This morning I wore a new outfit I made. I cut one of Mark's thin white A-shirts and cut it to where the bottom covered to the bottom of my bra. Because it was Mark's shirt the arm holes and the neck line was loose. I had to wear a bra to run comfortably. I cut the material out of a sports bra except for a couple of inches to keep my large breast from drooping too much. I wore a pair of thin nylon shorts Jake had given me without any panties. Yes, truly trailer trash.

Mark seemed to be used to my displays. There was no doubt I flashed him every time I bent over. And in the park, six men and Mark watched me use the exercise stations. I flashed them for fifteen minutes before starting my run home. This time a couple of the men followed us all the way back to our trailer.

The strangest thing happened, when I closed the door to the trailer, I found myself fantasizing about inviting them in and having a gang bang. I went directly to my phone and text Jake with a picture of my outfit.

Me: 'What do you think of my homemade outfit?'

Jake: 'Looks like you could attract a wolf pack.'

Me: 'Ha, I did. Can I have an orgasm this morning as a reward for initiative.'

Jake: 'Is Mark there?'

Me: 'Yes.'

Jake: 'Yes. But Mark has to watch and tell me about it.'

I was ready to do almost anything.

Me: 'I will tell him.'

Jake: 'Come to work thirty minutes early this afternoon. Sid and I want to talk to you.'

Me: 'Yes Sir. Anything to worry about.'

Jake: 'You are going to have to learn to be more positive. Have Mark give you five strokes with the leather paddle and tell him why you are being punished. Wear your largest anal plug. Have Mark report to me on the punishment.'

Me: 'Yes Sir.'

It excited me that Jake was going to make Mark punish me and then report back to him.

I came back into the living room/kitchen where Mark was drinking water. I took one of Jake's sports drink.

I said, "How do you like my outfit?"

Mark answered, "It is something. You know that those guys were watching every move you made."

"I know. Mark, it turned me on and I want to have an orgasm. Jake gave me permission to have an orgasm if you watch and report back to him on what happened. Want to watch?"

"If I can get off doing it."

"He didn't say you couldn't. In fact, if you will give me five licks with the paddle and watch me have an orgasm, I will give you a blow job."

Mark smiled and said, "Deal."

I said, "Let's get naked and go to the bedroom."

I got Miss Bi, my large anal plug and lube out. We both took our clothes off. I handed the paddle to Mark and said, "Give me five whacks. I took a negative attitude toward Jake when he asked me to do something simple. This is my punishment."

I handed Mark the paddle and put my hands on the bed. Mark hesitated. I looked back and said, "Are you going to hit me?"

Mark said, "I'm not sure I can. Your ass is so beautiful."

I pleaded, "Please hit me with the paddle. Jake commands it."

Mark hit me a soft lick. "Thank you. Please give me another harder."

Mark asked, "Would you do anything Jake tells you?"

"I think so."

This lick was much harder.

I said, "Thank you. Please give me another. I think you meant that last one."

Mark said, "I know my place but it does make me a little mad."

Whack. "Thank you. Please give me another. Mark, I think we are just forming a different relationship. You are still my husband but Jake is my Master."

Whack. Mark said, "I know and truthfully I am happier than I have been in a long time."

"Good. Thank you. Please give me another."

Whack. And this one was hard. "Thank you, Mark. That last one made up for the first. Is my ass red?"

"Yes."

"Take a picture and send it to Jake in your report. I want him to know that I was really punished." I could feel my juices running down my legs. I knew that Jake would see it. Mark took the picture on his phone. Still bent over I handed him the lube. "Please lube my ass hole and shove this in."

Mark stuck two fingers covered in lube into my butthole and pushed the large anal plug that was about the size of Jake into it. As he pushed it in, I fantasized this was Jake's big dick. I thought about Jake's beautiful dick deep in my ass while Josh fucked my pussy. I was so ready for an orgasm.

Mark finally got it all the way in. I said, "Take a picture of the plug."

I laid back on the bed and shoved Miss Bi to the hilt. I had an immediate orgasm. I jerked and squealed for what seemed like minutes. When I came down I looked over at Mark sitting in the chair watching me pleasure myself. The pain from inserting the large anal plug had turned to a pleasant feeling that I knew made my orgasm that much better.

I smiled at him as he was slowly stroking his little member. I said, "Come over here and let me help you with that." Miss Bi stayed impaled in my dripping vagina as I sat up. Mark came over and stood in front of me. I took his little dick in my mouth and started sucking. I didn't stop moving my hips with the long prong of Miss Bi rubbing on my G-spot as the little extension pressed into my clit.

I put my hands-on Mark's hips to control the rhythms of his strokes in and out of my mouth. I sucked hard on Mark's small member. He didn't last long and I had one more really nice orgasm before he came in my mouth. It was easy to collect his cum without any spillage.

When Mark finished, I said, "How did you like that?"

"It was very good; you are becoming quite the cock sucker. Your technique is really good and you seem to enjoy it."

"I do Mark, I like men's cocks. I can't believe it took until my mid-thirties to figure out that I like it so much. Mark, are you still okay with what is happening?"

"Actually yes. Sometimes I get just a little jealous knowing you are screwing other men. But I am just glad to still be here. And let's face it I am getting more sex now than before you became a, ah—."

"Slut. No need to deny it. I am trailer trash slut. What's more I like that. I liked teasing those men this morning. Jake didn't make me do that. I like that I have a husband that will let me do anything and I like being controlled by such a powerful man as Jake."

Mark hugged me.

That melted me a little toward him as I said, "Now I am starved. Fix me lunch. I need the calories and carbs."

Mark fixed us lunch. We discussed Cherry's coming home on Friday. I told him I was going to admit to being a slut with a master. Mark went to work.

I arrived at Mistress Sid's office at the time Jake instructed. As I entered, Jake and Sid were sitting on her couch talking. I bowed my head and said, "You wanted to see me."

Sid said, "Here come sit in the chair. You are to be Merilee for this conversation."

I sat in the chair across from them. Sid said, "Jake wants to take over the obligation we have to each other completely. If you agree then I want it completely forgotten that Rod and I ever did anything. You are no longer to treat me as a Mistress. Jake."

"Here is the deal, I take over the agreement you made with the Woolsey's. She no longer has any obligation to you. I pay for whatever happens. Additionally, I want you to come tomorrow and interview with Gannon Security. If you get the job with us, then you will no longer work for Sid. If you work for Gannon Security part of the compensation is a commission on business you help win including Lutz. It may be possible for you to secure Cherry's four-year degree and have a new occupation within a week. What do you say?"

I said slightly taken aback, "There are a lot details left out but I am really at your mercy. So, sure."

Jake said, "I will tell you everything tomorrow afternoon. All you need to do is show up at our office at four, in your most impressive slut outfit, and ready to do whatever it takes to get a job with us."

"What if I don't get the job?"

Sid said, "You continue to work here. But I am giving you the rest of the week off. I think you will win Jake's job. If not, be here next Tuesday."

I said, "Okay, I will be at your office tomorrow afternoon at four, dressed to impress."

Sid said, "One last thing. I want your assurance that you will never mention being my sex slave."

I said, "You have it. And Sid, I appreciate all you have done for my family."

Sid hugged me, smiled and said, "We are going to be such good friends. I will be so glad when you and Cherry come clean with each other."

I said, "Me too."

As we walked out Jake said, "I got the report from Mark. Sounds like that worked out well for everyone. I loved the pictures. Your ass was nice and red. I worried that he couldn't really give you the punishment you earned."

I smiled at Jake and said, "Oh, he made me know I was being punished. Thank you, Sir, for setting me straight. Thank you also for taking my contract from Mistress Sid, ah, I mean Miss Sid."

Jake just nodded.

I interview for a job with Gannon Security

I thought about my best slut outfit. It was a hard choice now because I did have several to choose form. The one I chose was bought from Teddy's the day Jake and Mark took me. I laid it on the bed after showering and trimming my body hair. I stood looking for a long time trying to decide if I could really either wear it out in public or especially interviewing for a job.

The outfit consisted of a silvery bandeau top that barely covered the top of my nipples but enough support underneath not only to support my G-cups but to push a lot of flesh over the top. It had a band just beneath my breast, leaving my torso bare and back mostly open. The black flared pleated skirt showed my new improved hips. It had an elastic band that held it at my waist. Teddy had added a pair of lace thigh highs with a black garter belt with one suspender on each side to hold the stockings up. It came with a black silk thong.

I put the outfit on and it was definitely slutty. The silvery top looked like it wanted to drop off my breasts as so much protruded out the top. My stomach was now hard and was shown off nicely in this outfit. The skirt was so short that the lacey tops of the stocking with the connected garter could be seen. While my ass was covered standing, if I bent my ass could be seen. Added were a pair of silver four-inch heels and the slave collar Sid had given me, making it a true slut outfit. I put on extra red lipstick.

I decided this was what Jake wanted. Off I went to Jake's offices. His offices were in a warehouse section in a large old building. I parked, got out and had second thoughts. Could I really walk into an office building wearing this ridiculous outfit? But it was almost four and I knew that being late was not an option.

An old guy at a front desk said, "Hi, you must be Melons. Mister Gannon said for you to go right up. His office is on the second floor up those stairs. His office is at the end of the hall."

"Thank you."

"Lady thank you. You're a sight for these old eyes."

"Thanks Henry." I read his name on his shirt.

As I walked up the stairs, I felt Henry's eyes boring into my rear end which I am sure was in full view.

There were a lot of offices which looked empty. You could tell this was an old warehouse being repurposed. I knocked on an open door. I heard a come in. Jake was sitting in a large, very masculine office at a large old wooden desk.

He smiled and said, "Hi, Melons. Right on time and glad to see you." There was that seldom used smile that melted me.

"Hi Sir, glad to be here. Do I look okay? I am so worried that this is not what you wanted. I brought another outfit if it isn't."

Jake said, "Turn around." Jake got up after I made the 360-degree turn and said. "That is exactly right. In fact, that is so good my dick stood at attention as soon as you walked in. Let's start the interview. Come take my dick out and give it your best blowjob."

I got on my knees between his legs, unzipped his pants and pulled out an already hard dick. He was wearing Dockers with the Gannon Security golf shirt. I said, "It does look like my outfit affected you."

I kissed the large tip. I loved his cock. It was huge and smelled good. I pulled his balls out and lightly stroked them as I kissed and licked the head of his penis. He was slumped in his chair, allowing me to get at his genitals. I took the head all the way in my mouth. I slurped and moaned as I enjoyed the sensation of having him in my mouth.

I took more and more in my mouth as I rocked back and forth on his rock-hard shaft. I flicked my tongue around the tip. I was making more and more noise as I got faster on his shaft.

Before long Jake said, "Here it comes. You are getting to be an expert."

I felt his discharge start as I squeezed his large balls lightly. I could feel his contractions. He filled my mouth as fast as I could swallow. I had very little of his jizzum seeping out the sides of my mouth. But I knew my lipstick was gone.

Jake reached down, pulled me upright and kissed me deeply. His kisses were few and each one meant a lot to me.

I heard, "Hi Melons."

I looked around to see Josh sitting on the couch. He had clearly been there as I sucked his dad off. "Oh, hi Josh. Did you enjoy the view?"

"I sure did. My dick wants the same treatment but I think we need to talk first. Dad has no self-control."

Jake growled at his son, "I'll show you self-control boy!" Josh just smiled at his Dad. "But you are right, we need to tell Melons what is going on."

Josh said, "Melons, do you want something to drink?"

"Yes, please."

Josh came back with a bottle of water for each of us as Jake started the discussion. "Let me first tell about our business. I knew the Woolsey's from my days as a detective. We became friends starting with a theft at their firm which I investigated. They talked me into their body building hobby. I attended a few meets, competing on their team. They knew I wanted to start my own private investigation firm and that I was ready to retire. The company that was providing their security services was going out of business.

Anyway, the Woolsey's are very generous. They saw an opportunity to help me and themselves. So, they put together a deal for me to buy the existing company and provide the service they wanted. I can't say enough good about how the Woolsey's have treated me. They loaned me money and their business is the basis of my business. My vision all along was for a more detective oriented business but the security assessment, installation and monitoring is a great cash flow business.

Last year, I paid off their loan, bought this property at a fire sale and the business is now cash flow positive with only debt being for the building. Josh came on board and because of his expertise, he is a natural to take over the security monitoring, expand into cyber, and let me focus on building up the PI side. Which brings us to why you are here. Any questions so far?"

I said, "No, I think I somewhat understand your business but still wonder why I am here. I really don't have any skills that could help you."

Josh said, "I don't think that is true. You are very determined. You have raised a daughter and helping her with college. I also think you have skills you don't know about."

Jake picked back up, "Anyway, two things are happening. I want to focus more on the detective side and if we could get the Lutz Distribution business then the monitoring services side would be in great shape. I want you to consider coming to work as my Investigative Assistant and help me grow the detective business."

I frowned and said, "Is this for real? I just don't see that I can help you."

Josh said, "Melons, you need to be more positive about yourself. If you keep that up, Dad might just turn you over his knee."

I laughed, "And what is wrong with that? I might just like that."

Jake actually laughed. "Melons I know that you would come in and learn. But while you are learning there is a lot of things you can do. I do want you to understand the business better before you take a job with us. Plus, I am very open to you finding your spot. Josh, also, thinks you would be very helpful on the monitoring side. So, Josh is going to take you around and introduce you. There will be three people that need to say yes. Josh, myself and Del. Del in my first operative on the detective side. He is a hard ass like me. He was the one that I thought would be influenced by your being dressed like a slut. Be nice to him. Do you understand?"

I said, "Yes, you want me to fuck Del."

Jake shrugged, "It is up to you. Depends on how bad you want the job."

I said, "What would I do as your Investigative Assistant?"

Jake said, "There is a lot of role playing needed in investigations. You will be surprised how often we can use a street smart, sexy female. Of course, there is a lot of just plain boring sitting watching, sneaking around and taking pictures. The only way to find your spot is to try it. Understand?"

"I think so."

Jake smiled, "Good now go with Josh and let him show you around. Remember, be nice to Del."

Josh showed me the monitoring center. There were about ten monitoring stations with five people working. He explained what these people did. He then took me to an area at the loading dock where a lot of equipment was stored and one guy working. He explained that this was where his guys staged the installations for the contractors. Josh was also suggesting possible jobs for me. A couple did have promise for me.

All along the way it was males. They all ogled me like the slut I am. This was making me so hot.

When we got to Josh's office, we sat on his couch as he said, "Think you understand the operation?"

I said, "Yes, Sir, I think so. But I am still not sure where I would fit in?"

Josh said, "I think to start with, answer phones, help us write reports, and learn how to manage the office. Over time Jake thinks you could help him attract more business. There are several areas in my area you could fit. With the Lutz business, we will have to grow my side quickly. But I must admit, Dad is very keen to build the PI business. That is really his expertise. He is a very good detective and I know he thinks you can help."

I said, "I would hate to disappoint your father. It is such a risk for him to bring someone like me on."

Josh said, "Not really. Dad wouldn't be interested in you if he didn't think you would contribute. If you take a job, you better believe he will expect you to contribute. This is too important to all of us. That's it. You need to be more self-confidence. I think you need to learn the way I did. Bend over my knee."