Like most kids, all through high school I suffered from having too little money and no sex. When I turned 18, in the spring of my senior year, my father said he thought he could land me a caddying gig at the country club. I figured that would at least help on the money front, but my first weekend I didn’t even get out on the course, so of course I made no money.
Before I left Sunday, I told the caddy master, “I know this game.” He said, “Kid, you’ve got to pay your dues. Maybe next weekend.”
That weekend was cold and blustery. I figured some of the regular caddies would stay home, but it also meant a lot the golfers did. I decided to wait it out. What else could I do, go home and jerk off? I played cards with the other caddies, but there was enough play that in time I was the only caddy left.
I was thinking of going home when the caddy master came in the caddy shack, looked around for an experienced caddy and said, “Shit, are you the only one left?”
I said, “Really, I can do it.”
He thought a bit, then said, “I guess I have no choice. Here, grab the bags for Mr. and Ms. Kent, and kid, don’t fuck up. Mr. Kent is the club president, and Ms. Kent is—well, you’ll see. Just try not to stare at her tits, okay?” He added, “And the way she looks today, it’ll be tough. Hurry up, I gotta go jerk off in my office.”
“Okay,” I said, recalling my dad saying the caddy master was a little off. But it was a chance to earn some money! I lugged the bags out to the first tee. I saw an older guy and said, “Hi, I’m Ben.”
“Yeah, okay,” he said. “I’m riding in a cart. My wife, as you’ll see, likes to keep in shape, so she’ll be walking.”
All the talk about Ms. Kent had me intrigued, but really, how hot could she be, married to this old coot? I pulled a ball, a tee and her driver from her bag and waited. I noticed a gathering of guys around the first tee. There were caddies who’d finished, and also a lot of members waiting in the cold. Could she be that hot, that they were all waiting for her?
I got my answer in a second—a resounding yes! Holy shit, I thought as a woman of about 25 made her way out of the women’s locker room, about five feet six, with long blonde hair pulled back in a ponytail hidden under a golf cap, dressed in a blue skirt, matching golf shoes and a blue golf sweater that contained a massive rack. Shit, the caddy master was right! I looked toward his office and saw him staring at Ms. Kent lecherously. And I knew what he was up to!
I was surprised the rest of the horndogs didn’t break into applause when Ms. Kent approached. I had to admit she was beautiful, and her tits were tremendous in her sweater. I handed her her ball, tee and driver and introduced myself.
“Very nice, Ben,” she said. I detected a Southern drawl. “Aren’t you cute? You just call me Cathy.”
I sprinted down the first fairway and awaited their tee shots. The old man duffed his, and I heard him swear. As I awaited Cathy’s shot, I wondered, how good can 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. “Looks like we have some work to do here,” I said, breaking the basic tenet of caddying to only speak when spoken to. But I thought she was nice.
“Yeah, we’ll get better. I’m always really nervous on the first tee. There’s always this big crowd gathered. And for what? I don’t know.”
Could she 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. But it took me a few seconds to find the ball due to the fact that I was watching her tits sway in her sweater well after she hit the ball. Be*fore I could say, “Nice shot,” her husband shouted, “Get over here and watch my ball.” I did, and got to watch another bad shot followed by a couple more.
When they both finally got their balls to the green, Cathy said, “Ben, we’re only going to play nine holes. It’s awfully cold.” Then she whispered to me, “Can’t you tell?” As she said this, she thrust her chest out and I saw huge nipples protruding from her sweater. Shit, I thought, is she like this with everyone? I calculated I’d have a hard-on by the third hole and be beating my meat by the fifth.
I tried hard to concentrate on my job. Cathy 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, “Cathy, try and hit it right here.”
“Hold it,” the old man piped up. “His first time caddying and he’s reading your putts? And why the hell is he calling you by your first name? Young punk!”
“Calm down, dear,” Cathy said. “I told him to call me Cathy, and I think he’s cute. I’m going to listen to him.”
I was nervous when Cathy pulled her putter back, but she stroked the ball right where I said, and it fell in the back of the cup! She jumped up excitedly, and I swear her tits hit her in the face! Hell, I know I saw her face vanish behind the mass of flesh in that sweater. She put a hand on the sweater between her tits so they wouldn’t jiggle so much, but continued jumping up and down.
After her tits came to a stop, she bent over the hole to retrieve her ball, and for the first time I noticed how tight her ass was. You could crack walnuts on it! Hell, it looked now like I’d have a hard-on by the second hole.
She got the ball from the cup and high-fived me. She said to her husband, “Hon, let Ben read your putt.”
“Oh no,” he grumbled. He missed his putt badly.
We played the next couple of holes without incident. I tried to pay attention to the old man so I wouldn’t get in trouble with him or the caddy master. At the fifth hole he picked up his ball early. As Cathy was about to putt, he said, “Hurry up, dear, I want to get back to the clubhouse and have dinner.”
“All right,” she said. “I just want to make this putt. What do you think, Ben?”
I told her what I saw. “It’s only nine inches. You gotta hit it hard and firm.”
She stopped and looked me in the eye, and it dawned on me what I had said. “Nine inches, hard and firm, is that what you’ve got?” she said.
I gulped, then said coolly, “Yeah, that’s what I’ve got.”
She drew her putter back and made the putt. She jumped up again, and this time didn’t even try to hide her bouncing tits.
“You rammed it right in,” I said, again not even noticing the double entendre!
Cathy looked at me and said, “Wait a minute.” She walked over to her husband, and I saw they were arguing. After a minute she stroked his arm and gave him a kiss. Then she came over to me and said, “Were going to finish all nine holes.”
During the last few holes Cathy and I talked while the old man grumbled. On the seventh fairway she said, “A cute fellow like you has to have lots of girlfriends, right?”
“Not really,” I said.
The truth was, I’d kissed a couple of drunk girls at parties, and had a minor hook-up with a slutty girl from a different high school that led to her putting her hand on my cock through my shorts. She said, “Damn, what have you got in there?” But before she could find out, her friends found us and took her away.
So I had an idea that I was kind of large, especially when I was hard. In fact I’d measured myself just a few weeks ago while looking at some of my dad’s girly magazines. I was nine inches.
“Here,” Cathy said, breaking me from a trance. “Teach me how to hit this shot.” She was deep in the rough. I noticed that her husband had ducked into one of the bathrooms on the course.
I stammered, “I’m sorry?”
“Stand behind me and show me,” she said.
I’m sure she saw my eyes widen. I looked once more at her tits in her sweater and my cock began to stiffen. As I approached her from behind, I tried to keep my distance and still teach her how to execute the shot.
She laughed. “You’ll have to get closer than that.”
My cock continued to grow. There was no way that she wouldn’t notice it when I pulled her closer. I pulled her tight in order to get my hands on her club, and as I did, my hands brushed her sweatered tits. “Sorry,” I said. At this point my nine inches could have cut glass, but I pulled her tighter and my cock pressed up against her pants. She had to feel its size.
“Oh my god!” she gasped, then stepped away and stared at my shorts. With her hand over her mouth, she said, “Hurry and teach me before my husband gets out of the bathroom.” She swiveled her ass back toward my cock and ground into me.
“Okay,” I said, “let’s do some practice swings.” I put my hands on top of hers, and we swung the club.
“More,” she said, pressing her ass harder into my cock.
“No, we’ve got to hurry,” I said, somehow showing restraint. “Now swing hard.” As I pulled my hands back, I let them rest a second on her tits. She swung hard and hit her best shot of the day. She looked at me and shook her tits. She said, “I see we both have something the other desires.”
Before I could respond, I heard the bathroom door open and Mr. Kent yell, “Hon*ey, what’s the holdup? I want to go to the clubhouse and eat.” I untucked my shirt from my shorts so the old man wouldn’t notice my erection. Cathy laughed and said, “No worries. It happens to my caddies all the time.” She added, “Just not that big.”
We finished that hole, and then the eighth. By the ninth green my hard-on had dissipated when Cathy stood next to me and said, “I’m sorry I’m not that good. At least I can dress the part.” And before I could reply, she said, “I take it you like my outfit.”
“Yeah, very color-coordinated,” I said. “I particularly like your sweater.” And she cooed, “I’ll remember that.”
My erection was returning, and I was adjusting my shorts when I saw the caddy master making his way toward the green. His eyes were fixed on Ms. Kent’s sweater as the Kents putted out. When they finished, he rushed up—to kiss a little ass, I figured. He said, “So how did it go?”
Mr. Kent said, “Fine. Whatever. I’m cold. I want to eat.” He stuffed money in my hand, got in his cart and drove off. Cathy walked past me, and as she too put some money in my hand, she whispered, “Be here next weekend.”
The caddy master looked at me dubiously and said, “Tuck your damn shirt in, for God’s sakes. Did you get a hard-on looking at her tits? Probably the last time you’ll see them. She’ll never use you again, I bet.” I thought it best not to say anything.
It’s funny, but that week in school I had new confidence with the girls, and even got the phone number of a cute one. But all week my real focus was on Cathy.
I arrived at the club early Saturday, not knowing what time the Kents would play. The caddy master saw me and said, “Do me a favor and go home, kid.” My heart sank. He continued, though, “But be back at 3:30. Ms. Kent is playing as a single, last tee time of the day, and she asked for you. Fuck if I get it! She never plays without Mr. Kent on weekends, and why the fuck would she ask for you? But you just have her bag ready by 3:30.”
My spirits lifted, and my cock hardened. She was playing alone, and she had asked for me! I wondered what she had in store for me. On my way out of the caddy shack a couple of older caddies grabbed me. Word had spread! One said, “I heard you got blue balls today.” An*other said, “Yeah, the Ice Queen.” He laughed. “She’ll make you hard looking at her, but you’ll be lucky if she gives you the time of the day. Keep it in your pants, kid.”
“I’ll be sure to do that,” I said. When I left the course, I gave that girl a call, and we hung out at the mall for a while. We got along, and she gave me a kiss and said she wanted to hang out. I did too, but all my thoughts were on Cathy. I got back to the club early. A lot of caddies were milling around. The talk was all about Cathy.
“Christ, did you see what she had on today?” one guy said. “I saw her on the practice green. She’s wearing this tight-ass pink number I’ve never seen before. My bet is it’ll fucking explode before the fifth hole. Christ!”
I pulled Cathy’s bag, cleaned her clubs and went through the bag to make sure she had enough balls, tees, etc. I pulled open the compartment that usually holds rain gear, because the weatherman called for late-afternoon storms. The first thing I saw was a pink wool sweater. I pulled it out and held it up. It still had the price tag on it. I could only imagine how her tits would fit in that sweater. Then I remembered that caddy saying she was wearing a “tight-ass pink number”! Hearing some of the caddies coming my way, I folded the sweater and put it back in the bag. I slung the bag over my shoulder and practically sprinted out to the first tee.
The crowd was bigger than the week before! I waited patiently. All conversation stopped as Cathy made her way through the throng. I noticed that along with a pair of shorts she was indeed wearing a “tight-ass pink” sweater identical to the one stored in her bag, minus the price tag.
She smiled and said, “*Afternoon, Ben. It’s a little chilly again today.”
I smiled, handed her her driver and headed down the fairway to spot her tee shot. She hit her drive well, and when she approached me on the fairway, I could see she was happy to see me.
“That first tee is never easy,” she said. “Always a big crowd, and I never hit it well—except today! You’re my good luck charm.” She paused, then continued, “Why do you think all those people come out to watch me play?” She arched her back and wiggled her tits right in my face. I began to get hard—one of what I thought would be many hard-ons for the day.
Cathy hit her next shot, and we fell into easy conversation for a couple of holes. I was really starting to like her. But I was also getting hard looking at her, though she wasn’t doing anything suggestive other than playing golf with the finest tits I’d ever seen and wearing the tightest sweater.
I began to wonder if those caddies were right. Was she the Ice Queen? Then on the fifth tee she said to me, “I wish I was playing better. Could you help me with my swing again?”
My cock began to harden and I swallowed hard as I walked behind her. I held her arms and we took a cou*ple of practice swings. My cock was a rock. “Just meet the ball and follow through,” I said professionally. God, my cock had reached up out of the waistband of my briefs! I had to untuck my shirt to try to hide it.
She hit the ball down the middle of the fairway—the best shot I’d seen her hit. She let out a little scream. As we got to her ball, she made a show of smoothing down her sweater, then said, “Funny, I didn’t think my sweater would make it this far.” I think I let out a moan, but I couldn’t be sure, I was so focused on her tits.
Then she hit her shot well, but into a trap next to the green. “Great shot,” I said. “You know, if you get out of that bunker and make you’re putt, you’ll have a birdie!” I really was excited for her.
She said, “I don’t even know how to hit a sand shot. Just pick it up!” She seemed mad at me, but as we made our way to the green I said, “I’ll help you with this shot.” I did want her to make a birdie, but I also had a raging hard-on. I figured it was now or never on both accounts.
I pulled out her sand wedge and motioned her to come near me. As I pulled her toward me, I made sure she noticed my nine inches against the crack of her ass in her shorts. I said, “Hey, I thought that sweater would explode by the third hole.”
Cathy ground her ass on my cock. I felt her knees weaken. Breathlessly, she said, “Teach me this shot.”
We took a couple of practice swings. I told her to hit a couple of inches behind the ball and make sure to follow through. Then I removed my arms from hers and set them on her sweater and caressed her tits. She turned around and kissed me. She began to French-kiss me but broke it off, saying excitedly, “I want to make this birdie.”
“Go into the trap,” I said. “Get your stance, and dig your feet in the sand an inch or so.” She did. I said, “Trust yourself, and execute the shot.” She gave me a wink, then swung the club the way I’d said she should. The ball lofted out of the sand trap onto the green and skidded right next to the hole!
Cathy jumped up and down, her tits bouncing with her. She got out of the bunker, took her putter out of her bag before I could get it for her and sprinted toward her ball on the green. I met her on the green and pulled the flag stick from the hole. I said, “Looks to be about nine inches. Just pull your club back and ram it in the hole.”
That broke her concentration. She looked me in the eye. I saw that her heart was beating fast. Her sweater looked alive! My cock too! I hoped she made her putt.
She took her stance over the ball, and for the first time I saw why she wasn’t that good a putter. I was pretty sure she couldn’t see the ball over her tits! But she tapped the ball right in the back of the hole. She let out a scream and lifted her hands over her head in triumph, and her sweater rose up too.
Seeing this as a chance to congratulate her for her birdie, I moved toward her, placed my hands around her back, pulled her toward me and kissed her. While we made out, I reached for her bra strap but couldn’t find it. She led my hands to the front of her sweater and broke off our kissing to say, “It’s a front-loading underwire bra. Trust me, someone of my size couldn’t get away with anything else.”
I wasn’t sure what she meant, but I sure wanted to find out! While looking me in the eye, she pulled her sweat*er up, smiling all the while. Once the sweater got over her tits, I saw acres of tit flesh jiggling inside her bra. I found the bra straps and unfastened them. It was as if the bra exploded! Her tits fell into my hands, and I played with them. Though I’d been dreaming about them for a week, I was still stunned.
I moved my mouth toward the left tit and sucked on it. The areola and nipple were so big, I had trouble fitting them in my mouth! I sucked hard, then moved my mouth around the breast, sucking in as much as I possibly could.
I felt a tap on my shoulder and opened my eyes to see that Cathy had slid her right breast in her mouth and was sucking on the nipple! I had no idea a girl could do such a thing! I joined her in sucking on her right tit, and we met at the nipple, then began kissing. After a while I broke off our kiss and pushed her tits together, then sucked on both nipples at once.
Cathy let out a long moan and put a hand on my cock, then began to beat me off through my shorts. “I want to see it,” she moaned, and ripped at my shorts. I took them off, and she took a step back, her tits falling out of my mouth. She stood looking—as mesmerized by my cock as I was by her tits. She put her right hand round the base of my cock and began to run her left hand up and down the shaft. Her hand barely fit around it.
Her eyes widened, and she cried out, “Ohmygod, I didn’t think they made those things that big!”
She led me by my cock to the edge of the green, on a little slope, and lay down. She removed her shorts and panties, and I saw her pussy glistening. As she lay in the grass, she opened her legs, spread her pussy and said, “Go easy at first.” I knelt on the ground and put the tip of my cock in her pussy. She let out a little scream. I watched as I eased my cock in her, inch by inch. Eventually I was able to get all nine inches in.
She moaned, and I felt her pussy cream my cock. “Pound me!” she ordered. “I need to be pounded!”
I began to move my cock back and forth faster. As I did, I looked up and saw that the faster I hammered her, the more her tits were bouncing. I increased my speed even more and thought I was going to split her pussy. Still, she yelled, “Harder!” Her tits were flying, she was moaning, and my balls began to ache.
She shouted, “Fuck my tits,” and I did! I pulled my cock out of her pussy and thumped it between her tits. She placed her hands on *either side of them and pushed them together, *enveloping my cock. Damn, I thought, this was just as good as fucking her pussy! I hammered away hornily on her tits.
I knew I was going to come, and I think Cathy did too. “Blow it on me,” she said. I pulled my cock from her tits and unloaded a stream of come all over her tits, sweater and neck and the grass. My come kept streaming for what seemed like 30 seconds. Once I finished, I leaned back to view my handiwork.
Cathy cried, “Ohmygod, grab a towel from my bag!” I ran down to get her bag, and as I lugged it back, she was licking my come from her tits. I hadn’t lost much of my hard-on, and whatever I lost began to come back. While I watched her lick up my come, I handed her the towel, and she removed the rest of the come from her tits, neck and sweater. She laughed and said, “Oh boy, the cleaners are gonna have a field day with this! Honey, do me a favor. There’s another sweater in my bag. Get it for me. After all, the club does have a dress code.”
I pulled the duplicate sweater from Cathy’s bag and removed the price tag. By the time I turned around, she had taken off the come-soaked sweater and put her bra back on. I handed her the new sweater, and as she put it on, she noticed my hard-on. She rose to her knees and said, “I’ve got to suck you off.” She dug her hands into my ass, pulled me toward her and, inch by inch, swallowed my cock.
The same problem I had with her tits, she had with my cock—she couldn’t get all of it in her mouth. She *removed her right hand from my ass and beat the remainder of my meat until I let out a moan and blew another monster load in her mouth. Amazingly, she swallowed it all, then lay back in the grass. “Yeah, I think I found my caddy for the rest of the year,” she said.
She looked up at the threatening sky, then back down at her tits, then smiled and said, “And I hope it doesn’t get too warm anytime soon. I spent my entire week shopping for sweaters to wear for you.”
I knew then that when I got home I’d have to find a way to thank my father for getting me this job!