I Never Thought Caddying Wood Be So Much Fun. (M) 18 (F)36,DDD

Like any other kid, all throughout High School I was always out of money and completely undersexed. When finally during the spring of my senior year my father helped me land a caddying gig at the posh Country Club near where we lived. My first weekend there I didn’t even get out on the course and made no money. I told the caddy master prior to leaving on Sunday “I know the game well”. But he told me “Kid, you’ve got to pay your dues, maybe next weekend”.

The next weekend was cold and blustery and I figured that meant some of the regular caddies would stay home. Unfortunately that also meant a lot the golfers stayed home. I decided to wait it out (what else was I doing to do, go home and jerk off). I played some cards with the other caddies but there was enough play where soon enough I was the only caddy left. I was contemplating going home when the caddy master came inside the caddy shack. He looked around for one of his more experienced caddies and said “Shit are you the only one left?” “Seriously, I’ll do a good job” I said. He thought for a second and then said “I guess I have no other choice. Here grab the bags for Mr. and Ms. Clark and kid, don’t fuck this up. Mr. Clark is the president of the club and Ms. Clark, well…you’ll see. And try not to stare at her tits okay”. He added “And the way she looks today, it’s gonna be tough. Hurry up I gotta go jerk off in my office.” “Okay” I thought, my dad said the caddy master was a little off. But at least it was a chance to make some money.

I took the bags and lugged them out to the first tee. I saw an older guy and I introduced myself, “Hi I’m Tom” I said, “Yeah okay” came the response from the old guy. “I’m gonna ride in a cart” he said. “My wife as you’ll see soon enough likes to keep in shape, so she’ll be walking.” All this talk about Ms. Clark had me intrigued but seriously how hot could she be married to this old coot? I pulled a ball, a tee and her driver from her bag and awaited her arrival. As I did I noticed a preponderance of guys hanging around the first tee. Some were caddies who had finished and there were also a lot of members waiting in the cold. I thought could she be that hot, that they were all waiting for her? Well I got my answer in a second and that answer was a resounding YES! “Holy Shit” I thought as I saw a women of about 25 make her way out of the Women’s Locker Room. She was about 5’6″ long blond hair pulled back in a pony tail hidden under a golf cap, blue golf shoes with a matching blue skirt and a blue golf sweater that contained an absolutely massive rack. “Shit” I thought the caddy master was right. I looked towards his office and saw him staring at Ms. Clark lecherously, knowing what he was up too. I was surprised the rest of the horn dogs didn’t break out into applause when Ms. Clark approached but as she got closer to me I had to admit she was beautiful and her tits were absolutely tremendous in her sweater.

I handed her, her ball, tee and driver and introduced myself. “That’s very nice, Tom” she said and I detected a southern drawl “Aren’t you cute” she continued. I sprinted down the first fairway and awaited their tee shots. The old man duffed his and I could hear him swear. As I awaited Julie’s first shot I wondered how good could she be with tits that big. She swung and dribbled the ball into the deep rough. I ran up to her ball and waited for her. “It looks like we have some work to do here” I said breaking one of the first tenets of caddying. Only speak when spoken too. But I thought she was nice. ‘Yeah we’ll get better, I’m always so nervous on the first tee. A big crowd is always gathered there, to see what? I don’t know.” I wondered if she could be that naive. Hell I was 18 and had never been laid and I wasn’t that naive. “Okay” I said handing her a seven iron. “Hack it out of here” She let loose a big swing and hit the ball pretty well. Although it took me a couple of seconds to find the ball due to the fact that I was watching her huge tits sway in her sweater well after she hit the ball. Before I could say nice shot her husband said “Get over here and watch my ball”. I did so and watched another bad shot followed by a couple of more. When the two finally got their balls to the green Julie said “Tom were only going to play nine holes today, awfully cold” and then she whispered to me “Can’t you tell”? As she said this she thrust her breasts out and I could see two huge nipples protruding in her sweater. Shit I thought is she like this with everybody? At this point I’ll have a hard- on by the third hole and beating my cock by the fifth. But I tried hard to concentrate on my job. Julie had about an eight foot putt and I figured I’d help her read it. I pointed to a spot about two inches to the right of the hole and said “Julie try and hit it right here”. “Hold it” the old man piped up, “His first time caddying and he reads your putts, give me a break. And what the hell is he calling you by your first name for, young punk”. “Calm down dear” Julie said, “I told him to call me Julie and I think he’s cute, I’m going to listen to him”. I was nervous when Julie pulled her putter back, but she put the ball right where I told her and it fell into the back of the cup. She jumped up excitedly and I swore that I saw her tits hit her in the face. Hell, I know for a fact I saw her face disappear behind her massive tit flesh in that sweater. She put her right hand on her sweater between her breasts so that her tits wouldn’t jiggle so much but continued to jump up and down excitedly. (end of part one)

Source: reddit.com/r/eroticliterature/comments/l9j2qd/i_never_thought_caddying_wood_be_so_much_fun_m_18