Caddymaster
by Openbook
Copyright© 2005 by Openbook
Erotica Sex Story: A young boy experiences some early adventures on his way to becoming a man.
Caution: This Erotica Sex Story contains strong sexual content, including mt/ft Consensual First .
It was early July in Groton, Connecticut. My family and I had just returned from our 4th of July visit with our cousins up at White Horse Beach, just outside of Boston. I'd had a great time that weekend, firing off two big bags of fireworks that my uncle had bought for us. I'm talking cherry bombs and roman candles here, not the sissy stuff that they call fire works today. This was back in 1954, that I'm talking about. I remember everything about that summer because it all started for me with that trip up to Massachusetts.
I had gotten my very first consensual feel from a girl. Gloria Ludsky was her name, and titties were her claim to fame. Big ones, and she'd let you feel them if you bought her a popsicle. I bought her a popsicle and took her behind the bathhouse changing room and played with those big titties the whole time she was licking that cherry flavored popsicle. She had on a one piece black bathing suit and she'd only let you play with them from outside her bathing suit. It was a hot day, and she was a very quick eater of popsicles, but it was still the best nickel I'd ever spent on a girl.
The first thing I did when we got back home was to run over to the Shennecossett Country Club and go see my cousin Dale. He was a caddy there at the golf course, and he was the family's main arbiter amongst us kids. My mother had nine brothers and sisters, and all of them had at least three or four kids. I had so many cousins in town that it was hard to keep track of all of them. Some of them lived in New London, across the Thames River, and I only saw them once in awhile.
Getting back to my story, I was twelve years old at this time, a tall, gawky, skinny kid, not having quite grown into my body as of then. I was really all arms and legs, but a fast runner, and full of piss and vinegar, as we used to say. I found my cousin Dale playing Tonk with some other Caddies. Caddies used to do that to kill time while they waited for their afternoon loop. Dale was about 16 years old at this time, a top scholar, and well on his way to becoming the first person in our immediate family to go to, and later graduate, from, college.
He was really smart. He was also ambitious, and wasn't going to be content to work over at Electric Boat like most of my uncles had been. Even a job at the submarine base was less than he was willing to settle for. Dale was also totally, completely and madly in love with Yvonne DeCarlo, a busty movie star of that time. Every morning he'd run outside and scream her name out to the world at the top of his lungs over and over again. So anyway, I find Dale and I tell him all about Gloria Ludsky, mentioning that this girl had tits bigger than Yvonne DeCarlo's, which got me a dirty look from Dale. I'm telling him the best part, about her sucking on the frozen popsicle while I'm rubbing those huge melons, when the Caddymaster rounds the corner of the building.
I never knew his real name, but all the caddies called him "Ratman", not to his face, but when he wasn't around. I think it was his teeth, they were a little bucked, but it might just have been his personality. He had been a caddy himself a few years before, but since he'd been promoted to caddymaster, he'd become a real prick. He'd suspend guys for tiny infractions or ban them from the course for little or no reason, just because he didn't like you. In the '50's, being a caddy was a good job. I made a minimum of $8.00 per day and usually more. To put that into some perspective for you, my father was a Chief Petty Officer in the Navy at this time, and I brought home almost as much as he did when I was caddying.
We worked six days a week in the summer, because the course was always closed on Mondays for maintenance or something. Vic Panciera was the Pro at the course in those years, and he could hit the ball a ton. He gave all the lessons and ran the pro shop and the caddyshack. "Ratman" was like an assistant-assistant pro. He had to kiss everybody's asses. The caddies only had to kiss his ass and Vic's ass once in awhile. Caddies also had to shag balls when Vic gave a lesson, and he never paid caddies for doing that. It was like a rent he charged us for keeping our job and laying around the caddyshack while we waited our turns to go out.
I'm talking to my cousin Dale when "Ratman" comes around the corner. He's pissed off about something and he wants somebody he can yell at to make him feel better. His eyes light on me and then move to someone else. I'm not even a caddy yet, so I'm kind of beneath his notice, and not really under his thumb yet either. "You, fuckface, quit trying to hide, get your ass out to the pro shop, you're carrying a single for Mrs. Diamond."
You have to understand, Mrs. Diamond was the world's worst golfer, the slowest, and hands down, the one person caddies most hated to caddy for. She always paid $1.75 and that was the minimum for 18 holes in those days. She was slow and she used to let anyone behind her play through. No one would ever play with her. She was a terrible golfer. She was in her mid to late 50's and it was no treat to be walking behind her, because she was somewhat obese. Like I said, I wasn't even a caddy yet, but I felt sorry for the guy.
"No can do Caddymaster. I'm handling the round for Judge Avery at 1:30." At Shennecossett, and at most other courses as well, members could make bookings for their regular caddy and the management always honored their requests.
"OK, asshole, you, shit for brains, pro shop now, Mrs Diamond." He was addressing my cousin when he said that.
"Sorry, caddymaster, carrying doubles at 2:00 for Dr. Myers and his wife." My cousin was a top caddy and he only carried doubles, and was booked up for every morning and afternoon for the whole summer. It went like that until every caddy there had given his afternoon booking and "Ratman" was getting the sinking feeling that he'd get stuck with the loop himself.
"Say kid, didn't you tell me you wanted to be a caddy once?" Now his desperate eyes were trained right on me. This was my golden opportunity here. It would require careful negotiation though, and I had to tread carefully.
"I don't have my caddy card yet Caddymaster."
"Fuck that, you don't need one if I say it's OK. Take the goddamn loop and we'll take care of the small shit later." I waited for a few seconds and then heard my cousin Dale speak up.
"He can't carry bags until he gets a card, Caddymaster, thats the rule, always been the rule."
"Fuck you guys, a bunch of smart asses, all of you. You, kid, come with me, I'll get your card signed." In five minutes I was a card carrying caddy at the best golf course in southeast Connecticut. For the rest of that summer, Mrs Diamond had me as her regular caddy.
It all happened because of one innocent suggestion I made to her. That first day we had made it all the way to the fourth tee and she had managed to make a 10 on the prior hole, her best effort so far. A 10 for her was like a birdy for your average golfer. The reason she made only 10 was that she actually managed to make solid contact with a mid iron and put it on the green about six inches from the hole. She made the putt too. You have to understand that I knew nothing about golf, but I did know that if we didn't get moving faster, we couldn't possibly finish before dark. So, I took a shot, what could it hurt, Right?
"Gee, Mrs. Diamond, you really smacked that iron back there. Have you ever thought about teeing off with an iron and not a wood?" Now her average distance off the tee was approximately thirty, forty yards tops. She'd just hit an iron 125 yards on the last hole, so you didn't have to be a genius to conclude she hit the irons better than the woods.
"Can you do that? Is is allowed in the rules I mean?" I took a wild guess and nodded to her in the affirmative, while reaching in her bag and handing her the same iron she'd just hit so well on the previous hole. She teed up her ball and smacked it again, right down the middle, at least a hundred and forty yards out, and was she excited. The rest of her round went very well, a bunch of eights and sevens, the occasional ten or eleven, with her all time best, a three on a par three on the back nine that left her positively trembling with joy. At no time after the third hole did I ever put a wood in her hands. It wasn't a fast loop, but nobody played through us either and it was a four hour round I think. I was cleaning off her club heads before giving them to the assistant to put away and Mrs. Diamond came over and handed me a five dollar bill. "For you, John, you're the best caddy I've ever had, thanks so much. Would it be OK with you if I ask for you by name the next time?"
"Sure Mrs. Diamond, I enjoyed it too. Ask for me anytime, I'd be happy to carry your bag." My career as a caddy was launched and made. As long as I was willing to caddy for Mrs Diamond, my job was also safe. She improved enough, that after awhile, other women agreed to play a round with her, and so I often got to carry doubles with her. I never got another $5.00 from her, but she never stiffed me either, giving me at least $2.50 for 18 holes. The important thing is that it also got me in solid with "Ratman", and that led me to meeting his sister, which ended up with me having a most memorable summer.
It isn't like "Ratman" treated me good or anything, but he appreciated that, as a new caddy, I wasn't booked up like some of the other guys and so I had time available to do him favors. Things like run to the machine and get him a soda or run over to the fifth hole and find Dr. Jacobs to tell him that his wife wanted him home right away. These were little, unpaid, chores that I would do for him that some of the older, more experienced caddies were able to get out of doing.
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