Trailer Trash Pt 04

I hope you enjoy this story. This part of the story is being told by Cherry, Merilee's daughter.

Edited by DRGriffin

Cherry meets Sid's son

On the Monday that Mom came to the Woolsey's to get fucked by two men with large dicks in front of an audience as she described in the previous part, my life took a turn. Until this week, boys hadn't been a part of my life. None had interested me. I was a virgin.

The pool outside the door of the Woolsey's guest house was heated so it was usable all year round. For the first three weeks, I stayed at the Woolsey's, I hardly did anything but go to school and work. Hence, I hadn't used the pool although I love to swim. I'm not a good swimmer, I blame my body shape for that, but I love to swim.

As I walked up to the guest house that Monday afternoon, I saw someone at the pool. There was a boy just about to dive in. He was five-feet eight, thin, blonde and interesting looking. Just before I opened the door to the guest house he waved at me and gave me a big smile. I decided to go and meet him.

Still wearing my school back pack, I entered the indoor pool area. As I extended my hand, "Hi, I am Cherry."

As we shook, he said, "Hi, I am Randy. Mom said you were staying in the guest house."

I was shocked. I had no idea Sid had a child. After I recovered from my shock, I said, "Sid is your mother?"

Randy said, "Yes, that's right. You are going Charles University, to become a nurse?"

"That right. With help from your Mom, I am in the four-year program. You?"

"I got my pre-med from Charles. I am in the last year of Medical School this semester. Luckily I can do this semester mostly at Charles."

I asked, "How old are you?"

"I just turned twenty-one. You?"

"I just turned nineteen. How did you get through Medical School so fast?"

"I worked hard. Really haven't done anything else, plus I took some college classes at sixteen."

"Gracious, you must be smart." Randy made no acknowledgement of this.

Randy was a small man with small features. He was very pale and hairless. He was wearing a small speedo, that left little to the imagination. I found him somewhat feminine looking and clearly very shy. He was pretty with gold locks and blue eyes. Something about him made me a little tingly.

Randy said, "I was going to swim some laps. Want to join me?" I felt like he struggled to ask me to join him but something about this attracted me to him.

I said, "I would love to but don't expect much. I like swimming but am very bad at it."

"I do it for exercise myself. Mom is a gym rat and has tried to get me into body building but I like this much better."

I realized, even though he was a small man he did have good definition. I gave him what I hoped was a seductive smile and said, "Let me change and I will join you."

He stood staring at me until I said, "Please go ahead. No need to wait for me. I will be back in a few minutes."

Randy said, "Ok," just before he jumped in and started his stroke. He could swim quite well.

I hurried to the guest house, excited and changed into my swim suit. I only had one suit and it was an embarrassment. It was an old-style floral one piece with a skirt built in. Mom had bought it for me when I was sixteen. It was well worn. My breast no longer really fit in the suit very well. My ass was too large for it but with the skirt I was covered. I decided that I had to buy something better.

When I got back Randy was well into his swim. I joined him trying to keep pace but he swam twice as fast as me.

Just as I was about to give up, Randy got out of the pool and grabbed a towel. I followed. As we dried off, Randy's eyes were glued to my heaving breasts. There was a good portion of my breasts showing because of the ill fit and shining from the water. I hoped he didn't notice how outdated the suit was.

I said embarrassed, "I know I need to buy myself a new bathing suit. I have had this one since I was sixteen and I have grown some."

This seemed to embarrass him. He stammered, "I, hah, think, hah, you look fine."

"Why thank you Randy. That was so sweet."

He turned red but said with his head bowed, not looking me in the eye, "Can you stay and talk for a little while?"

I said, "Sure but I have to get something to eat and study tonight."

He said, "Me too. Mom has something else tonight so I am on my own for dinner."

I said, "Want to grab our books, have dinner and study together."

He finally looked me in the eyes and quickly said, "Yes, I would like that. I will be back in a minute." He ran back to the house before I could say anything.

I went to the guest house and changed back into jeans and a tee-shirt. I had barely gotten dressed when I heard the knock on the door. He was dressed in jeans and a button-down shirt carrying a back pack.

He said, "Where would you like to eat?"

"I can't afford anything much and I do have a lot of work to do. Want to go to the Wendy's? It is close."

Randy said, "Ok but I would like to buy dinner."

I tapped him on the shoulder and said, "You are so sweet but I really think we should make this Dutch."

He again looked down and seemed downcast. I reconsidered, "But if you really want to then fine with me. I am always short of money."

He smiled a broad smile and looked me in the eyes for the first time quickly before looking away. We had a quick dinner and studied until 10pm.

We repeated this pattern, school, swim, eat and study, until Thursday afternoon. On my way home, I bought myself a new swim suit. It was, well, a Walmart two piece, so, conservative.

After we swam our laps, Randy said, "Melville is going to bring dinner here by the pool."

"Oh, that sounds good."

We were talking when Melville brought us dinner. Melville set up an outdoor heater making it very comfortable for us. I was really beginning to like Randy. He was the most unusual person I had ever met. While not being handsome he was pretty. Perfect complexion, nice hair and somehow, he appealed to me. But I couldn't understand why he hadn't made a pass at me. But I thought that was because he was very shy.

After Melville came to collect our dishes, Randy and I sat next to each other in lounging chairs, enjoying the sunset.

Randy said, "Isn't it pretty out here?"

"It sure is. I have enjoyed our time together. You?"

Randy said, "Very much. I like you."

"Do you really?"

Randy said a little hurt, "Sure, I thought you knew that."

"I guess but I am wondering why you haven't made a pass at me. Most boys want to grab my breasts on the first date. Are you gay?"

Randy frowned, "I don't think so. Cherry, I haven't had much experience with girls or of any kind. Mom, has been consistent that no girl is good enough for me. But, honestly, I don't think I am good enough for you. You are so pretty."

"Thank you very much. Have you ever experimented with guys?"

Randy said, "No. But I have also never really kissed a girl either."

"You are rich, attractive, twenty-one and never kissed a girl?"

Randy still not looking at me said, "I guess that is correct. I usually can't talk to girls. I have talked to you more in the last four days that any female except Mom."

"Would you like to kiss me?"

Randy said, "Very much but I'm not good enough to touch you."

I got the craziest thought, "Want to earn it?"

Randy brightened, looked at me and said, "What do you want me to do? I'll do anything."

"Anything?"

Randy said, "Anything."

I took a chance and said, "Remove your swim suit and massage my feet." The thought I had was that Randy wanted to be controlled. I had read about people who were into that and maybe Randy was.

Randy smiled, looked me in the eye and said, "Yes Miss, I would like to do that."

Randy pulled down his suit. He had a beautiful dick, about five inches long flaccid and small balls. His was the first dick I had seen since going through puberty. There was no hair on his body anywhere except his head. I started to get a tingle between my legs. A part of me already wanted to fuck this boy but another part thought about Mom and GranBern's warnings.

Randy got on his knees as I was stretched out on the Chase Lounge. He started to message my feet. He was doing a really good job of it, making me excited. After some time, he asked, "Have I done well enough to kiss your feet?"

I opened my eyes, smiled at him and said, "You may kiss my feet."

He kissed both my feet until he had covered every inch. I felt my vagina leaking into my cheap Walmart bottoms. I said, "Randy, you've been a very good boy. You have earned a kiss from me. Kneel by my head and kiss me on the lips."

He knelt by my head and kissed me gently on the lips. He was rock hard now and about seven inches long. I thought this was a long dick for such a small man but what did I know?

After we had kissed for a little, I reached down to my bottom and rubbed my now very excited twat. I said, "I would like to see you stroke yourself. I want to have an orgasm and think you have earned one also."

He said, "Thank you Miss Cherry. You are very good to me."

Randy stroked his penis while I slipped my hand into my bottom, finding my pleasure spot. I had a nice orgasm about the same time as he ejaculated. It didn't take long. His jizzum splashed on my torso.

Randy looked down and said, "I'm sorry Miss Cherry. I got my nasty stuff on you."

While it didn't bother me, I had the thought he might like being punished. I said sternly, "I didn't give you permission to get your nasty junk on me. Lick it off."

He didn't hesitate. He licked me clean, swallowing his own discharge. Again, for some reason I couldn't explain to myself this excited me. It was so sensual to have this smart, rich, and pretty boy doing my bidding. I was afraid I would screw him if this continued. So, I decided to end it but wanted to try one more thing.

I said, "I don't think that was punishment enough. You have been a bad boy. Bend over, I think you need to be spanked."

Randy said, "Yes Miss, I do need to be spanked."

He bent over, as I stood to give him four quick smacks. Randy said, "Thank you Miss."

I said, "Now put your swimsuit back on."

He did and sat back in his lounge. I said, "I have to work tomorrow night but would you like to spend some time together this weekend?"

Randy looked at me square in the eyes, "Miss I would like that very much. I have enjoyed this very much. I'm not worthy of the generosity of your time. Please can we?"

I said, "I will tell Mom that I need to study which is true. We can study together."

"Miss Cherry that would be so great. Thank you."

I said, "Good. Let's say goodnight and I will see you Saturday."

Randy said, "Can I have a goodnight kiss?"

I smiled and said, "Yes you may but that is all."

We kissed a deep loving kiss. I knew I was falling for this strange boy.

Sid confronts Cherry about the episode with Randy

Friday night, there was a note on my locker to come see Sid before my shift. I was early and Mom hadn't made it in yet. I changed into my outfit and went to see Sid. Sid's door was open and she waved me in before I could knock.

Sid said, "Good to see you Cherry. Have a seat."

We sat next to each over on the couch. I was nervous, afraid I had done something wrong.

Sid smiled, "Relax, there is nothing wrong. Did you know that there are surveillance cameras all over our property?"

I thought and realized I should have. I said, "Oh my Gawd. You saw what Randy and I did yesterday. I am so sorry. It just got out of hand. It won't let that happen again."

Sid laughed, "You should wait to hear what I have to say. I liked what happened yesterday. Randy is an unusual boy. And I think you are probably not typical. Randy is extremely smart but very shy. I have been a horrible mother but Randy has turned out really good. I am so proud of him considering he grew up without a father. Oh, Rod tried but he is, well, Rod."

"I am sure you did your best."

"Do you really like Randy?"

"I like him very much. He is, well beautiful."

Sid again smiled, "He is, isn't he? But so are you. Like I said no pressure but I certainly want to encourage you to explore what was started yesterday."

"I am not sure what I did or how it happened. It just happened."

Sid held up her hand, "I love my son. Probably the only person I honestly love. I thought before yesterday he was gay. Which is fine with me. He knows that I am very flexible when it comes to sexual preferences. I have given him every opportunity to tell me his. But I suspect it is not so much about sexual orientation. I think he sees you as someone who could take the lead in a relationship. And that is my advice. Take the lead. I think that would be good for him and maybe you also."

I looked at her in the eyes, seeing she was being earnest. I said, "I think I understand. I will try."

"Randy told me that the two of you are going to spend time together this weekend. Correct?"

"Yes."

"Does Marilee know?"

"I haven't had a chance to tell her about anything. I was planning to tell her that I need to study this weekend but not tell her about Randy yet."

Sid shook her head and said, "I think you should tell her the truth, you have met someone."

"I'm not ready. She is afraid for me to be with any boy. I know I am nineteen and it would be natural."

Sid said, "Ok, but remember I told you to be honest with Marilee. I sort of believe that Marilee may be changing her views."

"What do you mean?"

Sid said, "Just a feeling. After all your mother is dressing differently these days."

"That is true. Maybe you are right but I want to see her in person before I spring something like this on her."

Sid stood to give me a hug and whispered, "I hope it works out between the two of you."

I didn't know what to say, so I said nothing.

When I got back to the dressing room, Mom was dressing.

"Hi Mom," I said.

"Hi sweetie."

I said, "Listen I have to study this weekend, so I am going to stay at the Woolsey's this weekend. I will for sure be home soon."

Mom said, "I hate to hear that but you do what you need to do."

"Thanks Mom. I will call you."

I felt guilty about putting Mom off like this but I wanted to see what would happen with Randy.

My weekend with Randy

Randy knocked on my door at ten Saturday morning.

"What would you like to do this weekend?" he asked as soon as he entered.

"I have to work at the club tonight but can we catch a movie before. Let's have lunch a quick sandwich here and study until we go to the movie?"

"Okay."

"Tomorrow afternoon let's just hang around the pool."

"Okay," Randy said.

We had a quick lunch and studied in my living area. He was very focused on his work and barely looked up. I did occasionally catch him looking my way. I wore my most revealing tank top. It showed a little cleavage. I wore this top seldom as I normally don't like to show myself but it excited me to know he was staring.

At the movie, he again took glances at me but kept his eyes averted most of the time. About half way through the movie, I took his hand in mine, looked in his eyes and smiled. He smiled back. I whispered, "Do you like this?"

He quietly said, "Yes, Miss Cherry. Do you like for me call you Miss Cherry?"

"I do and I really like being here with you. My sweet pea."

He said, "Thank you Miss Cherry. I think you are beautiful."

"Thank you very much Randy."

From behind us was a "Shhhhh."

Randy looked back with a glare I didn't know he had. I said, "We do need to be quiet."

When we got to the front door of the hotel/club, Randy said, "Thank you Miss Cherry for being with me today. I really had a good time."

I said, "I had a really good time also. Want to meet at the pool tomorrow afternoon about four? That way I can really spend the morning studying."

"That would be nice."

We stood quietly holding hands. I knew he wanted to kiss me but was afraid to. I said, "Would you like to kiss me?"

"Yes! Miss Cherry I would but I am afraid to ask."

I smiled, "Well go ahead."

He lightly touched my lips with his. It wasn't enough for me so I reached around him, pulled him into my breasts and kissed him long and hard. I held him close enough that I could feel his manhood already hard in his pants. I ground my hips into his groin. We kissed for a long time. Toward the end, I put my tongue in his mouth and moaned.

As I released him, he had a lustful look on his face. My panties were moist and my breasts were heaving out the top of my tank top.

Randy said while staring at my chest, "That was a really good kiss. Thank you, Miss Cherry. Was it ok for you?"

I said, "It was a wonderful kiss. Randy, I want you to wear your little speedo trunks tomorrow afternoon."

"Yes, Miss Cherry."

I said, "I think I will wear something special for you also."

He grinned and said, "I will look forward to seeing what you have on.

"Good night," we both said.

That night I masturbated to a nice orgasm thinking about his perfect hairless body in his Speedos.

My cherry gets broken

Sunday morning, I knew I should drive over to see Mom but just wasn't ready to admit to her I was falling for a boy. I decided I wanted to go buy a real bikini instead of the Walmart thing I had. Just as I was getting ready to leave there was a knock on the door. It was Sid.

"Hi, Cherry. Thought you might like to try out this new coffee."

I said, "Well isn't that nice."

"I thought maybe we could talk."

I said, "Sure have a seat and I will pour us a cup of your coffee."

I took a sip and said, "This is really good. Thank you."

"It is a special blend we are trying from a local roaster. I thought it was good also. So, did you have a good time yesterday with my son."

I said, "I did. Did Randy say anything?"

Sid gave me a you know better look but said, "Randy doesn't really communicate that sort of thing. My son is not the talkative type anyway. Too much going on in that brain. It is up to us females to decide thing anyway. Don't you think?"

I said, "I am beginning to think that. But you know he has opened to me some. Is that unusual?"

Sid said, "He talks to me more than anyone I know of. Yes, it is unusual. Do you two have plans for this afternoon?"

"We plan to go for a swim and then hang out. We both have to study tonight."

Sid said, "Why don't you come to the home and have lunch with us?"

"Oh, I don't want to get in your way."

Sid said, "Nonsense. We would love to have you. Come at 12:30."

"Ok I will."

Sid had brought a package with her. She reached in it and said, "I brought you a gift. I saw your swimsuit and thought this would be better on your figure. You have a beautiful body, as does your mother and grandmother, and I thought this would show it off better."

She handed me a red bikini with a gauzy white cover. I said, "I can't accept this. You are doing too much for me as it is."

"Oh, nonsense. I don't remember where this came from but I clearly can't wear it. I mean after all, look at my top and this bikini. You know they don't go together."

I had to admit that there was no way she could wear it. I held it up and thought it might work.

Sid said, "Go try it on."

It was very sexy. Lots of boob showing above the U-cut neckline and a lot of ass cheeks showed. But it was not slutty. While being too large for Sid it was too small for me. But then it would get Randy's attention which is what I wanted. I came out of the bedroom for Sid to see.

She said, "Cherry, that really looks good on you. What do you think?"

I said, "It is more risqué that I would usually wear but it isn't really slutty looking. Is it?"

Sid frowned a little before saying, "There is one thing you need to do. You have a little pubic hair showing. You need to trim some."