Trailer Trash Pt. 01

Cherry's comments. As told by Cherry

Mom is right that I was a virgin when I graduated from High School. She and GranBern, my grandmother, had me so scared about sex that I wouldn't even talk to boys. I did have a lot of girlfriends and lots of boys asked me out.

Mom is wrong about me being the pretty one. She and GranBern were far more striking than me. They are taller, slimmer and that red hair made them stand out. GranBern was amazingly beautiful for fifty-two. I was more ordinary looking and while we all had large breasts, I was much closer to normal.

I badly wanted to be a nurse. I was prepared to work my way through school even if it took years. I knew that Mom and GranBern were willing to help anyway they could. Dad was an okay father but couldn't help us financially. I knew that he and Mom never had sex after I became old enough to notice. I mean the trailer was small enough so you could hear everything.

About the same time, Mom and GranBern were discussing my future, Sid Woolsey came in the club while I was cleaning and asked me to come to her office.

Sid Woolsey was also about GranBern's age. She obviously was a body builder. She was about five-feet two but extremely muscular with little body fat for a female. She had biceps that she showed off every chance she got. She would wear yoga pants and tank tops and/or sports bras almost all the time. Most of the time her midriff was uncovered to show off a muscular stomach. She had pronounced abs for a woman and a navel ring. It also looked like she had muscle where her breasts should be. She wore her blonde hair in a near boy cut. Her facial features were hard. She was oddly sexy looking in a butch sort of way.

After Sid asked me to sit she asked, "So what are you doing here?"

I scrunched up my face wondering what she meant. Finally, I said, "I am trying to make enough money this summer to go to nursing school. Mom and GranBern are both chipping in to get enough money for me to attend this fall."

Sid shook her head, "So you want to be an RN? Have you always wanted to do this?"

"Actually, I would like to get my BSN but for now, I would be happy with an RN. The BSN is a four-year degree."

"Yes, I am aware of nursing schools. How close are you to having enough money now?"

"We have enough to pay the tuition but not much else. I really need a car. It is a long way from the trailer park to the nursing school."

"Which school are you going to?"

"I am enrolled at Charles University."

The Charles University was primarily a medical school. It is closely associated with Charles Hospital. The complex was located on the other side of town from Mom and GranBern.

Sid gave me a very pleasant smile which caught me a little by surprise. She said, "You know we have been friends with Bernice for a very long time. I would like to help you. We have a home in that part of town with a guest/pool home we would be happy for you to use. We also have an old car you can use. We leave it there just in case we need an extra vehicle. Additionally, you can have a job in the bar as a cocktail waitress and continue to make some money. I would be surprised if you didn't make more money in tips that you do cleaning for us. You can work Friday and Saturday nights, right?"

I was taken aback. It took me a few beats to consider a response. I said, "That's correct. I would love to work Friday and Saturday nights. That is so generous. I don't know what to say. I mean, I hope this doesn't insult you, but why are you doing this?"

Sid smiled again. For such a severe hard woman, I was surprised that she could be warm and generous. "Two reasons really. First, Rod and I really like your GranBern. Great name by the way. Secondly, Rod and I had advantages because of our father that others haven't. It just seems right that we help others. You aren't the only person we have helped. Think about it. No pressure and honestly we have no expectations."

I smiled, stood and reached out my hand to shake, "Thanks so much. I will talk to Mom and GranBern and let you know."

I consider options to help Cherry pay for school. Remainder is told by Merilee

Cherry got home that night all excited saying, "Mom you will never guess what happened today."

"What baby?"

"Sid Woolsey called me into her office and offered to help me. She offered her guest home close to Charles along with a car I can borrow. She also said I could work in the bar on Friday and Saturday nights as a cocktail waitress. What do you think?"

I was taken aback and afraid they were somehow wanting to take advantage of Cherry. I said, "I don't know baby. We hardly know them."

"Mom, Sid said that she and Rod were good friends with GranBern. Can we ask her?"

"Sure baby, let's have GranBern over for dinner. I don't think your Dad will be home."

So Bernice came over came over for dinner. Cherry told her about the offer from Sid ending with, "What do you think? Sid said you were friends."

Bernice thought for a minute before saying, "We have known each other for a long time and yes I would say we are friends. You are sure they didn't want anything else from you?"

Cherry said, "No ma'am. She said that she was doing it out of friendship to you and wanting to help people with fewer advantages than they had."

Bernice looked and me, shrugged and said, "No way can you turn that down. It solves the transportation problem, free housing and let's Cherry continue making money without interfering with school."

I nodded but didn't like it. "Cherry you are a grown girl. If you want to do it this, then I am fine with it. I will make sure Ms. Woolsey knows how much we appreciate it."

Cherry jumped up and hugged first me and then her GranBern. "I can't thank you two enough. I think this is going to work."

There was someone at the door trying to get in. I knew it was Mark. I went and opened the door. He fell face first on the floor. He was passed out drunk. The three of us got him to bed with him mumbling something about losing the dishwashing job.

I was disgusted. We sat back down as Cherry said, "Mom, I know you have stayed with him all this time for me. Isn't it time you end this and start your life over? You are so beautiful; you could have any man you wanted."

Bernice shook her head agreeing with Cherry but I said, "Baby, it isn't that easy. I feel like I owe your father." But I thought more about maybe taking Bernice's advice and try her lifestyle. I mean, like Mom said, 'What did I have to lose?'

Cherry said loudly, "No you don't! He has been a horrible husband as long as I can remember. I don't think I can remember a time where I thought you two loved each other. It is long enough doing things for me? It is time to do something for yourself!"

Bernice said, "I think the child makes sense. He is nothing but a burden. Time for you to have a little fun. And I think I know how you can do that."

I knew what Bernice was talking about but Cherry just looked quizzical. I said, "Ok, leave me alone you two. Let's first get Cherry in school." But I was now seriously considering going to see Sid Woolsey.

I walked Bernice back to her trailer. I said, "Mom, I am seriously considering going to see Sid. Would you go with me?"

"Sure baby. Cherry is going to be gone leaving you with Mark and me. Cherry is right about losing Mark. If you are going to do that anyway, why not sow some wild oats and secure Cherry's future. I know the Woolsey's are good to their word. You're not going to like what they have to offer but you may find you like it."

"But you said they would hurt me."

"They probably will but so what. What is a little physical pain for giant orgasms and money? I believe it will release something in you that has been dormant. I can tell you I am glad for all the pain they gave me. I wish I could do it again."

"I hope you are right."

Mom and I go see Sid and Rod

Mom and I met the Woolsey's, Sid and Rod, at their club office Saturday afternoon. I got a good look at the cocktail waitress outfits. They were similar to playboy bunny outfits without the tails and ears. I thought that maybe that would be okay for Cherry to wear. Cherry was bigger up top than most of these girls, the cleavage was tasteful and they did wear fishnet stocking under the high cut bottoms.

We knocked on the office door and were asked to enter. Rod and Sid were both sitting at their desks. They had several comfortable couches and chairs sitting in the large office. They owned both the hotel and the adjoining bar. The bar offered a limited menu served out of the hotel's large restaurant. Both the hotel and bar were upscale with most of the clientele being business people during the week and then romantic getaways for couples on the weekend. They advertised a lot for weekend couples wanting a night out.

Rod like Sid was a muscle builder. To my knowledge, neither had been married. They seemed to always be together. Rod was about five-ten and maybe 150 pounds. He also had the same severe haircut and facial features as Sid. Even though they were fraternal twins, they looked like the opposite sex version of each other.

Sid took control immediately, "Please sit on the coach." She and Rod pulled up a chair close to where Bernice and I sat.

Sid continued, "I am so glad you called us. We have been wanting to talk about your girl. We are very impressed with her."

I said, "Cherry is really an outstanding person. She told us that you want to help her and that is what we want to talk about."

"Did Cherry tell you what we are offering?"

"Yes, Cherry wants to accept your help. We all appreciate it. Just don't know how to thank you. Mom tells me that there may be another kind of help you could offer if I am, hum, willing to do certain things."

Sid smiled and looked at Bernice, "Bernice has been working both of us I see. Do you understand what we want?"

"Well, Mom has tried to tell me but I am sure I don't understand."

"It is quite simple. You will be our plaything for some period of time for enough money to send Cherry to school. It is not much different than what our Dad did for Bernice more than twenty years ago. Bernice has been our plaything several times since. If I remember correctly, the first-time Dad had Bernice was for what three or four months? I remember that Bernice found it exhilarating. Didn't you Bernice?"

Bernice smiled, "It was certainly that. I found out a lot about myself. I also think Merilee will find out a lot about herself. There is also no way to tell her what will be done to her. I did assure her that if you found out she isn't submissive you would stop. I also told her that anything you do to her is really something she wants even if she doesn't know it."

Sid said, "We don't want to work with anyone that is not a submissive. Merilee, I am positive you are. I am equally sure that Cherry isn't or I would have offered her a deal."

I said, "I don't want Cherry involved in this."

Sid countered, "I personally think she deserves to know what her mother is doing for her. Cherry is a big girl. But as I said, it is up to you. Now for our deal, you will do whatever we want you to do for a month and for that month we will cover one semester of Cherry's college expenses. If after that month you want to continue we go for another month for another semester and so on. We will probably tire of you after a few months. If we tire of you before you decide to end it, then we will cover two years total for Cherry and you are free from our agreement."

I looked at Bernice as Bernice said, "What about $10k a month?"

Sid smirked, "My sweet baby, you know better. When did you get so assertive? Oh, I know being a submissive has nothing to do with this negotiation. I say with us providing transportation, housing and Cherry a job, then $5k a month."

Now Bernice smiled, "Let's make it $8k a month and I will throw in my services once a month for free. It might be fun for you to make a mother and daughter play your dirty games. And you will not interfere with Merilee's ability to work."

Sid said, "Since I am going to have her work as a cocktail waitress, instead of as a maid, then that is no problem. We will combine our playtime with her work. We accept the terms. Now we will require a legal agreement."

Bernice smiled and said, "Well that is new."

"We had a problem with someone that thought they could take advantage of us. We want you to agree to not sue us no matter what and never reveal anything we do. Anyway, here is the agreement. Take it, consider it, and Bernice should be able to answer most of your questions about what we want."

I said, "I will look it over and let you know."

Sid said, "Now as a matter of good faith, I want to see the merchandise. Get naked."

I froze. Sid said, "Oh come on. If you can't at least get nude in front of Rod and I, then no way you will be able to do this."

I shook my head in the affirmative, stood, and I started unbuttoning my blouse. Sid said, "Go slowly." I took it one button at a time. Pulled the shirt out of my jeans and slipped it off.

Sid said, "Not a very sexy bra, take it off quickly."

I unsnapped the bra and let it slide to the floor. Sid asked Rod, "Well what do you think?"

Rod said with a smirk, "Those are very squeezable. Can't wait to get my hands on them."

Sid said, "Very nice dear. Continue."

I unsnapped, unzipped and slid my jeans to the floor. Sid said, "Oh my goodness, get those ugly panties off. Is that the best you have to wear?"

I answered, "Pretty much."

"We are going to have to something about your wardrobe. Hurry get those off and I never want to see them again."

As the underwear hit the floor, reflexively I put my hand over my pussy. I had the instinct to cover my breasts but resisted it.

Sid said sternly, "Take your hands away. That pussy is mine as soon as you sign the agreement?"

I removed my hands and placed my hands on my hips.

Sid said, "Spread your legs."

I placed my feet about a foot from each other making my pussy lips visible.

Sid said, "Rod, do you remember where we have seen that color before?"

Rod smiled an evil smile, "How could I forget a pretty pussy I fucked so many times. It looks like Bernice's when she was young. I think I am looking forward to seeing if Bernice still looks like that. I bet that pussy can't even take my dick without being stretched out first. I think we need to test it before we agree. Let me dip my cock in it tonight."

Bernice said, "You can look but not sample until we have an agreement."

Sid said, "Merilee, you need to trim your pussy hair for us. Bernice knows what we like. Bernice, show us how yours is trimmed?"

Bernice smiled and said, "Yes Mistress." She pulled her skirt up and showed her neatly trimmed auburn haired panty less pussy.

I asked, "Mom, do you not wear panties?"

"Not often baby."

Sid looked at Rod, "This is going to be fun. Isn't she lovely?"

"I think she is very fuckable. I think we should fuck her tonight. I think she wants what I have." He grabbed his crotch as he said this.

Sid said to Rod. "I think you should show her what she is going to get. Let your snake loose."

Rod smiled again a lustful smile as he unzipped and pulled out a semi hard penis that was even in its state at least twice as long as Mark's. My mouth dropped.

I said to Bernice, "I can't get that into my pussy. He is more than twice Mark's size. I mean look at it."

As I talked Rod was getting harder. He liked me talking about his large dick. I could feel my pussy starting to seep. I hadn't felt this excited ever and couldn't understand how I could as they talked about me like a mare in heat.

Rod said, "I am going to tear that tight pussy up. I bet you have never been really fucked before by anyone like me."

Sid came closer and asked, "Are you getting wet dear?"

I nodded.

Sid asked, "Can I feel?"

I looked at Bernice and she shrugged. I said weakly, "Okay."

Sid slowly and gently slipped her hand over my pussy which was beginning to drip. It hadn't done that since the night with Eugenia. She let her finger slide over my extended clit. She gently rubbed it until I had a little sensation. I couldn't understand what I was feeling but I wanted her to continue.

She pulled her hand away, "Dearie, you are going to be so much fun. I think you are so ready for someone to really play with you. I could make you cum so easily."

Bernice said, "Okay that is enough. You have seen the goods. Let her get dressed."

Sid said, "Okay, get dressed Merilee."

I quickly redressed. Sid handed the agreement to Bernice, looked at me and said, "Dearie you have a lot of repressed sexual tension that needs to be released. You should do this, even if for nothing more than relief. You are going to love having a real dick to fuck and be played with."

We all shook hands as Bernice and I left.

Driving home, I said to Bernice, "I can't believe how excited I got when they made me strip. I just don't understand it. It was so humiliating but I did it for Cherry. Yet, Sid was right. I wanted her to give me an orgasm. That may be the closest I have come to a real orgasm in years."

Bernice said, "Are you going to do it? Three months may be enough to pay for two years at Charles."

"I think so but I want to sleep on it. If I don't get some kind of relief I won't be able to sleep. Do you have a vibrator I can barrow?"

Bernice laughed hard before saying, "Yeah baby, I will loan you a vibrator."

I started laughing also. I was thirty-six years old, wasn't sure I had ever had an orgasm from being fucked by a man and now I am borrowing a vibrator from my mother. But let me tell you I really needed the nice orgasm I had that night.

I decide to become the Woolsey sex slave for at least a month

The next morning, I knew I would take the Woolsey's up on their offer. The agreement essentially protected them and prevented any disclosure of our activities to anyone except Bernice and Cherry.

"Hi, this is Sid," Sid said as she answered the phone.

"This is Merilee. I have signed the agreement."

"Drop the agreement off at the club office and get measured for your waitress outfit. The manager, Early, will know you are coming. Be at our house Monday at seven and we will start your training."

"You mean the house where Cherry is staying?"

"Well, yes, but she is staying at the pool house. It is separate from the main house. Why?"

"I don't want her to see me there."

"That is your problem. I have already told you my opinion. To repeat myself, which I hate to do, you should tell her what is happening."

"I understand. I will be at your house Monday. Thank you."

"See you then."

As she hung up, I wondered if keeping this from Cherry was the right idea.

My first session with the Woolsey's

I decided I needed to dress sexy for my session with the Woolsey twins. My sexiest bra and panty set were from early marriage when I worried about impressing Mark. I also wore a blue jean skirt that I thought was short, hitting about mid-thigh and a thin white shirt. I put on additional makeup and looked in the mirror. I thought well at least you look like a slut. I had the blouse unbuttoned to show the start of cleavage. Of course, my cleavage starts high so that was only one extra button unbuttoned.

As I drove to the Woolsey's, I was incredibly nervous, anxious and excited. I was afraid of them as they had so much power over my family. I didn't want Cherry to find out her Mom was doing this. It, however, was exciting to me. I couldn't decide if it was sexual tension or that I was doing something positive for Cherry. But whatever it was, I was excited. I wanted to please the Woolsey twins. They were paying me a lot for to be their entertainment.