Trailer Trash Pt. 07

I took nipple clamps, pinched the tight flesh of his hard pics and clamped his nipples. I looked at him and whispered, "Does that hurt too much?"

He whispered back, "It is okay. I will tell you if it gets to be too much."

I nodded and placed an elastic cock ring around his nut sack and penis. This made his genitals stand up even more.

I said, "Now you are ready to watch your Miss Cherry pleasure herself."

I pulled the tank top off leaving me only wearing the red thong. I placed my hands under my large breast, pushed up and asked, "Are these what you have wanted all day?"

"Oh yes, Miss Cherry, I have thought about seeing them all day. But the mental picture is nothing compared to the reality of them. You are so beautiful!"

I could tell the discomfort of the nipple clamps and cock ring was only making accentuating the experience for him.

I sat on the chair, closed my eyes and massaged my sensitive breasts. I moaned as I pinched my nipples to make them extend as much as possible. I was so turned on just this came close to giving me an orgasm. I took one hand off a breast and rubbed the small cloth between my legs.

I whimpered, "Oh gawd, that feels so good." I started having an orgasm. With my eyes still closed I said, "Can you see that Miss Cherry is having a nice orgasm."

I opened my eyes to look at him as he said, "Oh yes, Miss Cherry I could see that orgasm. I want to put it in you so badly."

"Nasty boy, I am going to fuck you not the other way around. It will be soon, but first."

I stood pulled my thong off, sat back down, spread my legs and felt an already drenched pussy. I looked at him and asked, "Do you like my bald pussy?"

"It is the most beautiful thing I have ever seen. I love your white flesh."

"Wouldn't you want your penis here?" I pushed three fingers into my pussy and had another orgasm.

"Oh, fuck yes, I want it in all the way."

"Did you see that orgasm?"

"I saw that you had a nice orgasm." He was squirming.

I wasn't sure how much more of this he could take. Or for that matter me. I decided to let him know I was close to fucking him. I retrieved my medium sized rabbit vibrator, one I had been using for a long time and said, "This is my favorite vibrator. I have been using it for a long time. I thought you would like to see how Miss Cherry has managed to be a virgin when we fucked. After that I am going to stick your nasty rod up my sensitive hole."

"I want to see how Miss Cherry has pleasured herself."

I turned the rabbit on. I opened the clitoral hood with my thump and finger and lightly touched my clit. I couldn't take much of this without another orgasm but it set me up to be on the verge of a big orgasm.

I slide it all the way in. I looked at Randy and his attention was riveted to the vagina sucking up the gyrating phallic shaped silicon device. I closed my eyes to enjoy this beautiful boy watching me give myself pleasure. It wasn't long before I started a long spasm. I had the rabbit pushed all the way in to hit my G spot but also had it shoved squarely on my clitoris. My hips were rocking back and forth with the gyrating device. My breasts were rocking back and forth. I could feel them hitting my biceps. I kept up this motion for as long as this orgasm lasted.

I also lost track of what I was doing. It didn't seem that this one would end before I would lose consciousness. I felt the fluids quashing from my pleasure hole. I could feel it running into the crack of my ass. But the volcano between by legs finally stopped erupting.

I opened my eyes to see that Randy was in a trance watching me give myself this giant orgasm.

I pulled the vibrator out and put it back on the towel. I smiled at Randy, walked up to him, straddle him and said, "Did you like that?"

"Yes, Miss Cherry. I have never seen anything like it."

I sat on him with my labia barely touching the tip of his penis. I asked, "Are you ready for me to pleasure myself using your extension?"

"I am yours to do with as you please. Anything you want."

"Would you like for me to remove the cock ring before I start fucking you?"

Randy though for a minute and said, "I want to try it on. If it hurts too much I will tell you. But I want to touch you. Will you remove the handcuffs now?"

I said, "Not quite yet but soon."

I took his penis and flicked it over my clit. I was surprised how quickly I was ready for another orgasm. I was so sensitive there it seemed any pressure stimulated me to the point of eruption. He was squirming wanting his penis in my waiting hole. I shifted forward just enough to let a little in. I had an orgasm and I could feel my vagina contract tightly around his penis. He let out a moan.

Once the orgasm had finished I said, "Tell me how much you want to be all the way in me."

"Miss Cherry please push it all the way in. Your pussy is so tight when you have an orgasm I can feel it and it feels so good."

I shifted all the way forward so that my stomach was pressing into his. I could feel his balls pressed hard against my thighs. "Do you want the cock ring removed?"

He looked at me, smiled and said, "It hurts too good. Leave it but could you remove the nipple clamps. I think I have lost feeling."

I said, "Sid told me it would hurt when I removed them so get ready for the blood to return."

He nodded. I removed them and he yelled, "Ouch that hurt. Please rub them for me."

I rubbed both his nipples then kissed each of them. The redness quickly went away and he said, "That is good."

I said, "You have taken your punishment so well, I am going to give you a reward. How would you like to suck on Miss Cherry's nipples?"

"Oh, please may I Miss Cherry. I have been imagining it all day."

I leaned forward so that he could get his mouth on either breast. He sucked on first one and then the other. Even though I wasn't moving on his penis the pleasure of his dick in me, the slurping sounds he as making and the pressure his teeth were making on my sensitive nipple, I had another orgasm.

I said, "Oh my gawd. I just had another one just from what you were doing with your mouth. I think I am ready to have your hands on them."

Randy said, "Please Miss Cherry let me touch them."

I reached behind him and hit the cuff release button. Each hand grabbed a handful of tit but he still didn't release the nipples from his mouth. I started a slow rock back and forth. He was hard and long and felt so deep inside me. I now couldn't distinguish when one orgasm started and ended. It seemed to be continuous. I was so glad he could last. I am sure if I hadn't given him a blow job earlier in the day he would have been already finished.

I wanted his hands on my ass, so I took them off my tits and placed them on each of my prominent mounds of flesh. He obliged and took a full handful of each cheek and helped me pump his elongated member. I was in heaven, having continuous orgasm.

He said, "I am going to cum."

"Fill me full my sweet boy."

With that he came. There was still a good volume even though this was his second orgasm today. I wrapped my arms around his head, squeezing my large breast around his head. As his ejaculation started to subside, we kissed a hard-deep French kiss as my pussy continued to milk him of all he had to give.

When he was clearly finished, I continued to hold him. Finally, he said, "Miss Cherry, I need to get the cock ring off."

I laughed, raised up off him and gently removed the constricting device. I grabbed a towel, handed it to him and said, "Clean me off and then go get us some water."

He wiped me off, I took the toys back to the bedroom, and sat on the towel on the couch as he brought us both some water. Neither of us bothered to put clothes back on as I think we both knew that we were going to screw once more. I sat on my knees with my arm draped around him so that my breasts were brushing against his arm.

As we drank our water I said, "Did you enjoy that?"

He smiled a big smile, "I don't know how to describe it. It was wonderful. Almost out of body. Did you?"

"Well yes but I was in control. Was there any of it you wouldn't want repeated?"

He said, "How would you like another glass of wine. I saw you had the beer I like."

I said, "Sure."

He came back, handed me my wine and took the same place, only this time one hand held a beer and the other was placed on my thigh. His penis never really quite went flaccid.

"Miss Cherry I liked it all. I loved the teasing even though it made me ache. I loved watching you pleasure yourself and if I hadn't been handcuffed I couldn't have kept my hands off. The nipple clamps and cock ring hurt but it seemed to enhance my pleasure. So as far as I am concerned it was perfect."

"Did it really not embarrass you for me to dress like I did today?"

"No, I loved it. It made me ache but that only made the release better. As far as I am concerned you can dress like that anytime you think it's right."

"Sid told me we probably needed a safe word."

I had finished my wine. I placed it on the table and started to rub his chest.

Randy said, "We probably do. Let's think of one."

I began to rub down his hard stomach. He was small but ripped. Swimming had made him hard and lean. With my big ass and tits, we were probably close to the same weight. He finished his beer and sat the can down. He took me in his arms and kissed me as he started to rub my still sensitive breasts.

I let out a moan, "Oooooooo..."

I found his now hard penis and said, "It didn't take you long, did it?"

He said with his face close to mine still feeling up my breasts, "I have been ready for you since the day I saw you at the pool. The attraction for me was almost immediate. I love your body."

I said, "Me too."

He pushed me back on the couch. He slipped his dick in my still gushing pussy. It felt so good for him to be taking me. He raised on both arms and looked down on me. He said, "Miss Cherry, I am falling so hard for you."

He wasn't moving much but I still had another orgasm. "Did you feel what you do to me?"

He said, "Yes, I did."

I said, "I am falling for you also. But let's not get too far ahead. We have so much school. I like how things are progressing. I'm not ready to use the L word."

He said as he slowly started pumping in and out of me. "No but I want to make a commitment to you. I want you to be my girlfriend."

I pulled him down on me and kissed him, then whispered in his ear, "Oh yeah, I want to be your girlfriend."

He started moving even more and said, "I want us to be committed to each other."

I said, "Oh gawd, that feel so good to me." He was taking long slow strokes in and out of my pussy. He was so light on top of me but his penis filled me up so nicely. "I am ready to make a commitment to you. Let's just not say L yet."

He said, "Okay Miss Cherry."

Now he started moving faster. My orgasms were now coming faster. I could feel him so hard inside me. He pumped me for a long time and I enjoyed every stroked. He finally came for a third time that day inside me. This time it was a smaller discharge.

We laid on me for a long time, before I said, "We need to get to sleep."

He got dressed, but I didn't. I said, "You know Sid has invited me to have lunch with you tomorrow."

"She told me. That sounds fun."

"You know she told me that she wanted me to wear one of the revealing outfits she paid for. Are you okay if I do that?"

He smiled, "I am always fine with that. Dress as sexy as you want. Make Mom jealous and Rod wish he was me."

"Okay, I am going to study tomorrow morning."

Randy said, "Me too. I will see you at lunch. Let decide on a safe word tomorrow."

We kissed goodnight and Randy went to the main house to sleep. I didn't bother bathing or putting on clothes as I went to bed so happy.

I have lunch with the Woolsey and swim with Randy

Lunch at the Woolsey's main house was at one.

I had purchased four outfits at Teddy's to choose from. The most obvious was a tunic style white beach dress. It fit loose with over the shoulder straps to hold it up. It was cut to show a lot of cleavage and draped on the side which allowed a peak of side boob. It draped to about mid back. It ended about mid-thigh with a black lacy pattern. There was no way to wear a bra without it showing. The material was thin enough to be see though in certain light, so Teddy had sold me a pair of bikini cut silk panties to go with it. I wore white sandals and a white straw hat with outfit.

I knocked on the door at one. Melville said, "Good afternoon, Miss. The others are already on the patio."

I followed Melville to the covered back-yard patio. Already seated at an outdoor table for six were Sid, Rod and Randy. They all stood to welcome me.

Sid said, "Well aren't you pretty in that dress. My goodness Cherry when you dress up, you certainly can turn heads. Is that from Teddy's?"

I said, "It is. Randy, do you like?" I made a 360 degree turn to show it all off, then removed the hat and handed it to Melville.

Randy smiled a big approving smile, "You are beautiful Miss Cherry."

Rod chimed in, "You certainly are a delight. I am so glad you are joining us." I had only met Rod once.

I said, "Sid, thank you for buying the clothes for me. I feel so guilty."

Sid said, "Please sit. Melville go ahead and serve lunch. I hope everyone likes salmon. I like to have fish for Sunday lunch."

Melville placed a plate in front of us already with a large piece of salmon and a salad. He put vegetable and bread in the middle for us to serve ourselves. He poured wine for us all.

Sid said, "Enjoy everyone. Cherry, please don't feel guilty for our help. Rod and I have helped many young people like you. Haven't we Rod?"

Rod said, "Yes. May I call you Cherry?"

I said, "Yes you may Mr. Woolsey."

Rod smiled, "Rod is fine. Sid and I decided long ago one of the ways we would give back is to find deserving young people and help them out. I never had a kid and in many cases, we have relationships with people for a life time. In fact, as we speak there is a very smart young man named Jerome that we are giving similar assistance. Randy has met a few of them."

I said, "I think that is so good of you but so many people are helping me; Mom, Granbern, you and Sid. I just wish I knew how I would pay you back."

Sid said, "Make good grades and get you nursing degree. That will make all of us happy."

The meal was very good. For a while, I found out a lot about the Woolsey businesses. I had no idea that they were into so many things. I knew they were rich but I think I may have underestimated how much.

After we finished desert, Randy said, "Cherry and I have made a commitment to each other. Neither of us wants to go any further than to say we are in a committed relationship but it is getting a little more serious than just friends."

Sid smiled at me, "I think that is great. What does your mother say?"

I said, "She doesn't know about Randy yet. I am going to take care of that this coming week after mid-terms. I wanted to tell her in person and, well, I have been so busy and this has happened so fast I just haven't had a chance. I don't have class Friday. I was hoping that you would let me have the weekend off."

Sid said, "Oh sure, just let the club manager know. Randy, have you met Merilee?"

Randy said, "No mam. Cherry has told me a lot about her."

Sid said, "She is a very nice lady. You will like her."

We continued talking until about four when I said, "I so appreciate lunch and the afternoon. I have really enjoyed it but I am sure you have other things to do. Plus, I wanted to go for a swim this afternoon. Randy, would you like to join me? I have a surprise for you."

Randy smiled big and said, "I finished studying this morning and I was hoping we could find something to do. Swimming sounds great. Mom, can you do without me?"

Sid laughed, "Like I could stop you. You kids have fun."

When I got up to leave, both Rod and Sid hugged me. Sid whispered, "I am so happy for you."

I whispered back, "Me too. Thank you."

The surprise I had for Randy was a new very revealing swim suit. It was a white string bikini I got at Teddy's. The triangles on top barely started a couple inches above the nipples and was only about three inches wide at the base of my breasts. Strings tied behind my back and neck. The bottoms tied on the side with the bottoms barely covering my Mons Pubis and was only about four inches wide covering my bottom. With my broad hips, this left most of my ass cheeks hanging out. I didn't think I could really wear this in public. It came with a thin gauzy beach cover that tied at the neck.

So off to the pool I went. Randy was already swimming. When I got there still with the cover on, he got out wearing his little bit of a Speedo that clearly outlined that beautiful penis I loved. Yes, I loved it.

I smiled a coy sexy smile and said, "Ready for you surprise?"

He said, "Yes, Miss Cherry."

I removed the beach cover and did a 360 turn. "What do you think?"

His penis was beginning to grow. Before he could speak, I stepped to him and placed my hand on his growing penis and said, "Never mind. What I am holding tells me what I need to know."

He said now with a completely hard penis barely covered by the Speedo, "Miss Cherry you are so sexy. I am thinking such nasty thoughts."

I rubbed his penis and thought he was going to cum. I said, "Down boy. We need to get some exercise. I mean swim now but maybe other kinds of exercise later. Jump in and cool off my bad little boy."

He clearly needed to get cool but so did I. I wanted him as badly as he wanted me.

We swam for about thirty minutes. My stamina was getting better but he was still about twice as fast as me. It was now after five. We sat the chase lounges next to each other.

As we sat, I asked, "Are you ready to meet my Mom?"

He was staring at my wet breasts that were mostly uncovered.

He said, "Whenever you want me too. Think we should buy something for each other to signify our relationship?"

I said, "I really can't afford to buy you anything. I want to tell Mom this week but I would rather do that with just the two of us. Maybe I will tell her Friday and have you come over Saturday. I am still working through how to do this. She has been so adamant about boys."

He said, "Whatever you think but it is time. As you know my last test is on Thursday. I plan to take the weekend off anyway."

Randy was practically salivating looking at me. He was turning me on also. His penis was sticking straight up with the little Speedo was nowhere close to covering him.

I said, "You are such a naughty boy. Take your trunks off. They aren't covering anything anyway."

He pulled his trunks off and stood waiting for me to tell him what to do. I said, "I think Miss Cherry needs to have some lotion rubbed on her. Dry my back off and rub the lotion in my bag on my back."

I rolled on my stomach. He straddled me, with a leg on each side of the chair and squirted the body lotion first on my shoulder.

I said, "Now do my legs."

He kneaded my calves and then my thighs. My privates were getting sopping wet.

I said, "Miss Cherry's pussy is getting her new bottoms nasty, untie them and move them aside."

He untied the bottoms and I raised enough for him to pull them off. I said, "Now massage that oil into my gluts. I have had a lot of exercise this weekend and think that will feel good.

He liberally oiled my big ass cheeks. He kneaded from side to side and then sat with his bottom between my spread legs and massaged up and down from my back to my gushing pussy.

I asked, "Do you like Miss Cherry's fat butt?"

"I love Miss Cherry wonderfully round full butt. It's not fat. It is perfect."