Ray Ray Rides Again and Again - Cover

Ray Ray Rides Again and Again

by Openbook

Copyright© 2005 by Openbook

Erotica Sex Story: The ninth story in the Caddymaster saga. Jackie's brother Ray learns some valuable lessons about the kinds of girls he chases.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Teenagers   Consensual   Humor   .

Chapter 1

By the time my brother Ray got to be a junior in high school he already had a reputation for being the seducer of many girls. It was his hobby as well as his main passion in life. He was always on the look out for his next conquest. I remember one particular Sunday when my mother had gotten all of us up and dragged us off to an early mass at St.Joseph's over in New London. My family didn't go to church very often, so my mother liked to go to different parishes when we did go. That way, if people ever commented on not seeing her at mass for awhile, she'd simple name another parish, not too far away, and tell them that's where we went for mass now.

We were about halfway through at the mass and I was starting to think about where my fiancee, Ellen and I would be going after I picked her up at noon. It was then that I noticed my brother making eye contact with a very cute dark haired girl that was sitting in the same row we were, about three people down from Ray. She was with three or four other family members and, after a few minutes of them making little faces at each other, I saw her mother leaning down and hissing something in her ear. The girl started looking forward right after that and I thought that Ray had struck out with her. We were heading out of church and Ray had closed the gap between himself and the girl and was introducing himself as they waited for the people coming out of the aisles ahead of them. As luck would have it, Ray caught a big break when the priest and the girl's mother got into a long conversation about some charity bazaar that she was on the committee for. By the time she and the priest were through talking, Ray had gotten her phone number and had promised to call her soon for a date.

My brother had started caddying up at Shennecossett Golf Club when he was around twelve, like I had before him. He made about eight bucks a day most days, not from caddying, which he seldom did, but from playing Tonk and rummy with the other caddies. He was a great card player and took pride in never cheating anyone. He loved five handed Tonk the best, because he claimed he averaged two bucks an hour profit when he played it. He kept elaborate records of his profits at cards, writing down all the information he remembered after each days play. He kept track of what tendencies players had in saving certain kinds of cards in their hands. I stopped playing with him his first year as a caddy, because I could never win when he was in a game. Lucky for him, most of the other caddies figured he was just lucky. My father sometimes took Ray out to the Sub base and let him sit in on the poker game over at the Chief's Club. Ray usually did pretty well there, but he lost sometimes too. Once Ray caught an old Chief cheating the game by holding out cards. Ray didn't say anything, but when he got up to go to the bathroom he stopped at the bar and told my father about what he had seen.

Fifteen minutes after my brother had returned from the can and had resumed playing, a couple Chiefs came by and stood behind the cheater. My father told Ray it was time to leave and head home, so he cashed in and left the game. A couple days later my father gave Ray about fifteen dollars and told him that was one eighth of the money the Chief had on him when they caught him red handed after Ray was gone. He never said what happened to the Chief that got caught, but I'll bet it wasn't pretty.

After we got home that Sunday from mass, my brother was on the phone and talking to that girl, whose name I'd learned on the way back home, was Kathy. They talked for about ten minutes and then Ray put down the receiver and came into our bedroom where I was changing clothes.

"Jackie, you heading over to see Ellen?" When I told him I was, he wanted to know if I wanted to go to a carnival over in New London and take him along, and he'd get back home on his own. I told him that we'd give him a ride over in any case, because we'd probably be going out that way anyways. He ran back and made his arrangements with Kathy. It turned out Ellen liked carnivals so we went and spent the day at the carnival too. We got there and I parked my big truck about a block away from the empty field where the carnival had been set up. Ray thanked me for the ride and ran off to try to find Kathy. Ellen and I walked around and stopped to get something to eat. All the food was being made and served by the ladies from St. Joseph. They had the food concession at the carnival. If they hadn't gotten it, or another group like them, the carnival wouldn't have been allowed to set up. That's just the way things got done then.

We ran into Ray and his friend right after we got done eating, they were waiting in line for the ferris wheel and Ray already had his arm around her shoulder. Everybody got introduced all around and Kathy and Ellen started talking together. Just standing there I got a lot of information about Ray's new friend. She was sixteen, had quit school after finishing tenth grade, had been engaged to be married, but had caught him fooling around with another girl and dumped him. She worked as a waitress in her uncle's restaurant, but just until she met somebody and got married. Now, to me, that all seemed like bad news, and she was someone I'd probably want to stay clear of, but Ray just stood there smiling and nodding at her, his arm around her shoulders and his hand toying with her earlobe and behind her ear. She kind of slapped his hand away from her ear, but was giggling when she did it.

"Don't do that Ray, I told you what that does to me. Can't you even wait 'til we're on the ride?" She was turning and leaning into him as she said that, her boobs pressed tight against his chest. Ray was a fast worker, but even he wasn't that fast. This Kathy was a real pistol, and I was afraid she might get my brother into some trouble. I decided that the four of us would hang around together so that I could make sure they didn't go off the deep end wind up doing something stupid. He had known her all of two hours now and he was already further along with her than most guys expected after a few dates. Maybe she was afraid that we'd think she was too young and innocent or something, but it wasn't long before Kathy turned to Ellen and resumed talking. "You know I only got engaged to Tony because I was running a little late with my period, it's not like I really loved him or nothing. And then, after my 'friend' finally came, I didn't want to hurt his feelings and break it off right away, you know? I just wanted you to know that I'm not broken hearted or nothing, or on the rebound. I'm ready to start a new relationship now."

"When did you and Tony break it off?" I loved Ellen, but the woman was a devil, always stirring up trouble.

"Friday night after I caught him right in front of his house in the back seat of his car with my cousin Tina. She's only thirteen, the little tramp!"

"Hey, a girls got to start sometime, I was only twelve, and it was with two brothers I'd just met in the movies. They took turns, but I only liked the cute one."

Ray and I looked at Ellen as she went into telling her little fantasy story. Ray didn't know this about Ellen, that she made up stuff all the time and pretended that she was actually like that. Even Kathy looked over at Ray and I trying to see how we were taking all of this.

"Ellen, remember that time over at the creek when we was all skinny dipping, when Ray got all excited and you had to do him to get him to settle down so we could do it? I'll never forget that look on his face when you played with his little noodle. How old were you then Ray, twelve, thirteen?"

"I remember that time Jackie, and it wasn't so little. I thought for awhile that he was going to come out the other side. You should be so little, is what I say. Especially lately, right Ray?" By now Ray's face is all red and he's looking from face to face, not knowing whether to shit or go blind. "You're a lucky girl Kathy, you got the big brother here, even if he is shorter and not as old. Just a little advice from girl to girl though, always make sure you got a pillow under your ass with this one, especially outdoors. I was pulling out little pebbles stuck to my butt cheeks for days after that time at the creek. It was worth it though, because he really knows how to make a girl feel good. Ray, why are you so embarrassed, I'm just giving the devil his due." I noticed that Kathy was squirming around and now had her arm wrapped possessively around Ray's waist. Ray was just quick enough on the uptake that he understood that all of this was working in his favor, so he didn't say anything at all.

We stayed close to the two of them for several hours and then Ellen had the idea that we should all leave and go out to dinner together. When Kathy saw how big the truck was and how little room there was in the cab, she suggested that she and Ray ride together in the back. We drove around for an hour, I was looking for a restaurant that we'd never been to before. When I finally found a place that Ellen agreed was OK, we stopped and parked and waited a few minutes for the two lovebirds to get themselves buttoned up and pulled together. Ellen had told me that she'd taken some peeks back at where Ray and Kathy were sitting and said that Ray must have hurt himself in his dick, because Kathy had it out and was kissing it to make it all better.

After we were all settled in at the restaurant and the waitress had gotten our orders, Ellen started right back in with her playing games again. "Kathy, I bet I've done it with more guys than you have. I'm already up to forty one. And that doesn't even count the ones that I only." She put her thumb in her mouth and pushed it in and out. She and Kathy shared a good laugh about that.

"No, you're way ahead of me. Forty one, that's a whole lot. You're really bad! But I like you anyways. So when are you and Jackie going to get married?"

"We're not really getting married, that's just for my parents, They're really old fashioned, you know? The only way they'd ever let Jackie sleep over at night is because we're engaged. If I want to do it with another guy, I have to go somewhere else to do it. My parents only let me do it with a guy if we're engaged, so I have to sneak around."

"Jackie doesn't get pissed at you for the other guys and all?"

"Nah, Jackie's a good sport. He understands that a girl sometimes has days when she's feeling a little crazy and needs to blow off some steam. Last week he drove me over to Ledyard so I could visit with a few good friends of mine. He even waited in the living room for the four of us to get finished just so he'd be sure I got home in time and wouldn't get put on restriction by my dad. He's really thoughtful that way, aren't you Sweety?" She started running her fingers through my hair then.

"I let you do it, but that doesn't mean I like it." I tried to put on a pouting face. Ellen and Kathy kept up their running conversation. When Ellen kept getting more and more outrageous and Ray and I didn't seem to be getting upset at what she said, Kathy started regaling us with stories as well. It seems that she had started early just like Ellen and, while she had only been with 'about fifteen' guys so far, she was very interested in the whole idea of multiple partners. Not a gang bang she hastened to assure us, that wasn't her style she said, but maybe two or even three guys, she thought that that could be interesting. We took a small break while we ate our supper, but right after, Kathy wondered, out loud, if there was maybe a place we could all go together and 'get us all better acquainted'?

"Are you talking about the four of us all getting together and fucking, tonight?" Ellen had a big smile on her face as she asked the question.

"I don't know, I guess so, if you all want to, I'd be game. But no lezzie stuff, 'cause I only like guys, that's it!"

"I guess we could drive out to this place we go to sometimes and park and all get in the back of the truck. It's almost dark already. But I was kind of hoping that you and I could do some things. I've never done it with another girl, and you're kind of cute, and so I thought you wouldn't mind if I got you ready, like in the mood, while they watched us."

"No, that's Ok, I'm already in the mood, really."

"Not even if I ask you nice and say 'pretty please'? A girl knows what another girl wants and needs. I've been sitting here for the past hour just wishing I was sitting right on your pretty face. Just this once, nobody'll ever know, just us four?"

Kathy bounced up out of the booth and yelled at Ellen "You're sick! Ray let's get out of here, right now!" When Ray kept his seat, Kathy just stormed right out of the restaurant and started walking back towards the carnival which was a good two mile walk. We paid the check, Ray taking care of his half, and left to go look for her and give her a ride back to wherever she was heading. When we got outside the restaurant we saw her talking to a man in a car that had stopped alongside the road for her. As we watched, she climbed into the car and off they went. We were in the truck and heading back home when Ray put his arm around Ellen and asked her if she was ready for her forty second guy.

"Ray, you know I lied about that. You'd be number eighty four, but don't tell Jackie. He still thinks he was the first. I'm really sorry if I ruined it for you and Kathy, she seemed like such a nice girl, too."

"Don't be sorry, Ellen, I had a great time, maybe the best time ever. How old did you say your oldest sister was? If she's like you, I think I'd like to meet her."

"She's ten, Ray, want me to see if she'd like to double with us the next time we all want to go out?"

After we dropped Ellen off and we were driving home, Ray was full of questions about the things I allowed Ellen to say. I explained that Ellen said the things she said as a game, and it wasn't my place to allow it or not. It was one of the things that I loved most about her, the contrast between what she would say and how she really thought. Ray got quiet and was thinking about what he'd seen and heard with us that day. Just as I was parking the truck and locking it up, Ray came around and gave me a playful punch in the arm.

"You always were a lucky son of a gun, Jackie. I really think you've hit the jackpot with Ellen." I put my arm around him and we walked back towards the house. I was glad that Ray had gotten the chance to see my baby in action, she was really something when she got going.


Chapter 2

My brother and I were walking over to Aunt Betty's house to have a talk with Lenny. Clara, Lenny's wife had called and talked to my mother the night before, saying that Lenny was having problems with the pay that I was giving him. I was surprised at that because I was paying him a dollar fifty per cord delivered, and I paid him in cash. I was taking all the long deliveries where there might be a need to stay overnight. Usually Lenny could leave around six in the morning and be home before dark. I had him delivering five loads a week. I was puzzled at what he could be having problems with. He was taking a break from driving for me fairly soon anyway because his job as Caddymaster was starting up again after Memorial Day.

"Jackie, thanks for coming over, hi Ray-Ray." Lenny met us at the door and led us into the kitchen where Aunt Betty was baking her oatmeal and raisin cookies, and Clara was sitting down peeling some potatoes. Clara was pretty close to having her first baby, which actually arrived on Memorial Day that year, and she had been staying home more and not going out with Lenny on his deliveries. There's a minor thing about my Cousin Lenny that makes him a little different, he isn't stupid, but he looks at things a little different than some other people would, or sees the same things but comes to a different conclusion than most people would. He's a sweet guy and well thought of by most people, but some of his ideas are from out in left field somewhere. I liked him a lot. "Jackie, what I wanted to see you about is the money you've been paying me. I really like driving for you, but the pay's no good. You know I make fifty a week at the country club, right?"

"Sure Lenny, everybody knows that's what the Caddymaster makes, fifty bucks. I don't see why you have a problem."

"Plus, I make another ten bucks a week in tips from the members, on average. And I bet I make another three bucks a week easy from the golf balls I find on the way to and from the course each day. So altogether, Jackie, that's a lot of money, right?"

"It's still only sixty three a week Lenny, and that's for six days a week. You make about eighty a week working for me, and thats only for five days."

"How much do I make when it's snowing and icy out Jackie? How about on days where there's only one delivery and you take it, how much do I make then? Not sixty three a week I can tell you. So what I'm wondering, even though you are my cousin Jackie, I'm wondering why I should have to take a pay cut just to work for you?"

"Lenny, how much do you get paid in November for being the Caddymaster?"

"I get paid nothing, because in November I'm not the Caddymaster. The season is from Memorial Day to Labor Day, that's when I'm the Caddymaster, and that's when I make sixty three bucks every week. I need to have a job that's steady and dependable, Jackie, not one where I don't know whether I'm making any money from one day to the next. I'm sorry as hell Jackie, but you've got to get somebody else to do your driving, this isn't working out for me."

I looked over at my Aunt Betty for some help, but she was stirring her batter and wouldn't look up so I could catch her eye. I looked at Clara but she just looked away and kept peeling those spuds like her life depended on it. I looked at Ray finally, and he just shrugged his shoulders and said. "Lenny's got a point, Jackie, it doesn't seem right he should make less working for you than at the golf course."

"Ray, Lenny, I don't believe the two of you. Lenny I'm paying you eighteen bucks for a days work. By your own admission you only make ten fifty a day at the country club. The way I figure I'm paying you an extra seven fifty a day for working for me. What did we lose, maybe ten days work from when you started 'til now? I bet if you total it all up, the money I paid you, and divide by the weeks since you started, it would still average out to be at least sixty three a week."

"I've made up my mind Jackie, either pay me sixty three a week or I'm done driving for you."

"All right then Lenny, I'll pay you sixty three a week, but you have to be available to work six days a week just like at the country club. I may not need you some of those days, but you got to be available if I do, OK?"

"Sure Jackie that's fair. How about we start that right after Labor Day. I'm glad you could see it my way." Everybody looked relieved when Lenny was happy again. I guess I was relieved too, because I didn't want him to think I was taking advantage of him. When Labor Day came, Lenny was a new father and had just found out that his Caddymaster job had been phased out. I kept him on full time, year round, after that. I started putting aside two bucks per cord for him and paid him $63.00 every Friday after that until he finally went on disability. At the end of every year, maybe a couple weeks before Christmas, I'd take out whatever extra was still in the box and give it to Lenny as a Christmas bonus. It was usually a lot of money, more than he would have made for a whole season as the Caddymaster. After Lenny couldn't work anymore, and things got a little tight for them financially, I used to pay him fifty a week, under the table, as his 'retirement pay'. When the firewood business finally ran down to where it was no longer worth doing, in 1981, I just started paying him from my other business, out of my half of it.

 
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