Fore! Play

When I was younger, I played golf, not just for pleasure, as I do now, but as my employment. I was an Assistant Professional at several golf courses before I left the business.

At one of those courses, there was a female Assistant Professional, as well. Our boss, the Director of Golf, had nicknames for us. My name starts with D, and I was the older (22) and senior Assistant, so I was D1. Dorothy, the other Assistant, was D2, or Dot.

And Dot was hot. I always thought she looked a lot like Diane Lane, but with more freckles, and curlier hair. Oh, and much bigger tits. That may have been another reason for her D2 designation, but DD would have been selling her magnificent chest short.

Playing golf with Dot could be very, very distracting. She was 21, about 5'4" tall, with a nice firm ass, and decent legs. I would guess she weighed maybe 120. She was also very flexible, and her follow through, in the classic reverse C position, pointed her huge knockers up to the sky. Put simply, no one who played with her ever watched her shot, as that finish position put her big tits on display. I know I was always peeking, and she knew it.

She was also a tease. She would flash her ass, under her short skirt, while bending to pick up her ball.

I worked with her for three years, and toward the end of that time, her teasing increased. It was then I decided to act on it.

We were pretty evenly matched, game wise. I had the obvious length advantage, but that was largely equalized by the shorter Ladies Tees. I hit better wedges; she hit more accurate mid-irons. She was a great chipper; I was the better putter. All in all, it was a toss up.

This club we worked at was a private club, so it was pretty quiet a lot of the time. I was off that day, and Dot had worked the morning shift. We teed off about one.

Dot was leaning on her driver, waiting for me to tee off. "So, what are we playing for?" she asked. Usually, it was lunch, or something along those lines.

"I don't know," I replied, "but I think we should make it more interesting than lunch." We usually played skins, and match play with a stroke total kicker. That made 18 individual bets, with the match play winner as the 19th, and the stroke play winner making 20. We also paid bonuses for birdies or better. Plenty of chances to get even. "How about 'truth or dare'?"

This obviously came as a surprise to her. A surprise, but not a problem. It only took a few seconds of calculating the odds for her to agree. She extended her hand, and we shook on it.

The first hole was a 565 yard par 5, dogleg left off the tee, over a nasty bunker in the corner of the dogleg. I had planned to hit a draw, over the corner, off the right edge of the bunker, but I tugged it a bit left, and didn't catch it solid. I was fortunate not to be in the bunker, but I was in the rough left of it.

Dot walked up to the ladies tee, 50 yards ahead, while I grabbed the cart. As I drove up, I saw Dorothy's ball arcing beautifully over the bunker, before landing in the fairway and scooting a further 20 yards. Advantage Dot, a fact her smile confirmed on her return to the passenger seat.

I had about 310 left, from a reasonable lie in the rough. I figured I could get a low, running hook out of here. I took my 5 iron, pulled the ball back a bit in my stance, and hooded the face. I lashed at it with everything I had, and as planned, the ball screamed out in a low hook, doing its best Eveready Bunny impression as it ran out, to within 100 yards of the green.

"Nice shot!!" Dorothy called out from her position in the fairway. She hit a nice little fairway wood 10 yards past mine. We were pretty even.

My third was a spinning lob wedge that landed about 15 feet past, took one hop and jerked to a stop right there, leaving me about 20 feet, slightly downhill, breaking right. Dot hit a wedge that scooted up, 12 feet short. Her putt was uphill, right to left.

I was a bit worried she might draw first blood in our little game, but we both 2 putted our way to pars. Carry over.

The second hole was a downhill par 4, about 390 yards. Pretty straight, but O. B. right, with a pond left front of the green. I was on in regulation, but about 40 feet away. Dot missed right, but her chip left a 5 footer for par. My lag putt, usually one of my better aspects, slid about 8 feet past, meaning I had to putt first. But I had a good look at the line as my first putt went by, so I was able to put the pressure back on her by making the comebacker.

Dorothy lined up her putt. There was some pressure on this one. If she missed, I would have control of the first two questions in our game. She hit a good putt, but it died right and spun out.

"Fuck me!" she cried angrily.

"Not yet, Dot. Perhaps later, " I said with a smile.

She plunked down in her seat, obviously pissed about losing the hole. We drove to the third tee, a 180 yard par 3 for me. Dot started to walk up to her tee.

"Ahem. There is the little matter of a wager to settle." She dropped her head and turned to walk back to me.

"Alright... Get it over with." she resigned herself to her fate.

"Truth or Dare?"

Dorothy thought about it for a few seconds. "Truth", she decided.

"Just how big are your boobs?" I asked evenly. I looked her straight in the eyes, then looked down at her chest, then back to her eyes. Her mouth was opening and closing silently, obviously flustered. She had to answer, otherwise the dare could be worse. She finally caved in.

"34F" she admitted, reluctantly.

"Really? Nice!" I said. Dot was blushing. She knew I had one more left. "Truth or Dare?" I asked again.

"Christ!" she said under her breath, "Dare." she decided, hoping it would be easier than another truth. I let her off easy, for now.

"One more button, please" I grinned.

Dorothy had on her uniform shirt, which had a four-button placket, plus the top button. The top and first buttons were already open. One more wouldn't show much more. She flipped it open.

I hit my shot in the bunker, and made bogey. Dorothy made an easy par. As we walked up onto the tee of the par 4 fourth hole, she was almost giddy, knowing she was in control. "Alright," I said, "Truth". I knew she was probably trying to find something really embarrassing.

"How often..." she paused for effect, "... do you jerk off?"

So, no question about whether I do or not. Just how often. Maybe I could have some fun with this one.

"On average, or maximum abuse?" I asked.

"Jesus!" she giggled, then shrugged. "Your choice!"

"Well," I answered, "I would say four to six times a week, but I think I have done it that many times in a day, as well".

"Really?" she queried. The answer seemed to take her by surprise. At least the second part did. There was a little glint in her eye as she thought about it.

I was still thinking about her 34Fs when I teed off, and a couple of bad swings led to another bogey, while she made par. She was in control, and one shot ahead overall. I thought about going with a dare, but decided to see what else she could come up with.

"Truth" I said as we walked onto the fifth tee.

"Okay, let's see... What do you think about when you are jerking off?" she asked. She seemed to be genuinely interested.

I was beginning to see a pattern to her questions. "Clarification? What, or who?"

"I guess I mean who. Who do you think about when you jerk off?"

Now that I could use to my advantage. "Well, lots of women. Some from porn, or Penthouse, or Playboy. Sometimes it's you. Now that I know how 'big' you are, you will probably be more often".

That had the desired effect. She blushed, and turned away. When she turned back, her nipples were partially erect, showing little bumps through her shirt.

I absolutely bombed it off the tee on the par 5. The ball carried over the crest of the slope on the right side of the fairway, bounding down the hill to get me in position to reach the green with my second shot. Dorothy seemed a bit... distracted. Her tee shot was left, her second still left of the fairway, and her third just off the right side of the green.

I had a great chance here. My 4-iron landed just short of the front edge, and bounced on. It ran back toward the pin, but the slope of the left bunker pushed it off line to the right a few feet. When it stopped, I had 20 feet for Eagle. Dot hit a great chip, nearly catching the pin, and leaving 3 feet for par. She made it.

I had a good look at this putt, from all angles. It paid off, because I gutted it. It went down like a homesick gopher. "Yes!" I yelled, with a big fist pump.

"No!" she yelled back, knowing she was in trouble again. "Nice putt... Great Eagle 3" she added in sportsmanship.

With one putt, I had gone from one behind, to one ahead. I won the hole, so I had control. And the Eagle carried with it a bonus. I had a double coming.

Dorothy was waiting on the cart. We moved to the sixth, a 140 yard par 3 over a pond. "Dare" she said.

"Two more buttons," I said, holding up my fingers. She sighed, and popped them open.

Her shirt was now wide open. Her cleavage was on display, and since the placket of her shirt extended about 2 inches below her bustline, her bra was visible as well. It was black and lacy. And not doing a great job of disguising her hard nipples. I would definitely be paying rapt attention from here on.

Six was halved with pars, as was the par 4 seventh, and the short par 3 eighth. Every swing she made gave me a great view her creamy, freckle topped breasts. Watching her line up putts was equally interesting, as I could see right down her top. I didn't even pretend I wasn't looking, and she didn't even pretend she didn't know I was looking. There was a lot on the line for the ninth hole. Three carry overs and one for the ninth... a four bagger.

Two rather lacklustre bogies did nothing to solve the issue. That put five holes on the line on the tenth, another par 5. I was eager to go.

"Dorothy... You may want to button up while we go past the clubhouse", I suggested. She laughed and nodded, quickly taking her tits off display.. We stopped to get a few drinks for the back nine. Then it was off to ten.

The tenth tee was clearly visible from the pro shop, so Dot kept her top buttoned as normal while we teed off. However, by the time we were ready to hit our seconds shots, ... and without any input from me, I might add ... her tits were available for inspection again. It might have been my imagination, but it almost looked like she had pulled her shirt even lower.

When I stuck my wedge shot inside 2 feet for birdie, Dorothy knew she was done like dinner. She made par and conceded my putt for birdie. I won five holes, to go six up with eight to play in the match. I also picked up a shot, to go two ahead, and the birdie gets a bonus.

Dot braced herself for six rounds of truth or dare. She just shrugged, defeated. "Okay... what do you want to know, or what do I need to do.?" She was sitting beside me on the cart.

I rubbed my hands together and laughed like a villain. Dorothy just cringed. Let's start with your... ", she looked anxious, " ... Bra. I'd like to see it... "she quickly pulled her shirt aside, showing me the black lace through the open neck. " Let me finish... I'd like to see it in the dashboard of the cart. Take it off. "

Surprisingly, she really didn't protest much. She just pulled her shirt out, reached behind and unhooked it, then did the 'pull it out the sleeves' routine. Her uniform shirt was dark green, so, even without her bra, I couldn't see the colour of her nipples, but I could sure see the shape of them. Two very stiff buds of flesh stood at attention like little soldiers.. "Five more?" she said.

Without the support, her tits rode a little lower on her chest, but there wasn't much sag. I had to touch them. It's almost as though she knew what was next. "Yes, you can touch them...", she said anticipating my request, "... But it'll cost you two."

A pair for a pair, sounds fair. I nodded.

Dorothy took a deep breath, preparing to be groped. I took a deep breath, preparing to do the groping, but with permission. Begrudging permission, but permission just the same.

I reached out and took her big, beautiful breasts into my hands. They were warm, firm and heavy. I fondled her gently, moving closer. Her breathing became a little bit irregular, and her nipples stiffened more. She was starting to enjoy the contact. A barely audible moan came from her throat. "Three more." Her voice quivered a bit when she said it. Not in fear, but excitement.

I looked at her, and she rolled her eyes. "Okay," she said to my unspoken request, and grabbed the bottom hem of her shirt, lifting it up to her shoulders.

Her nipples were dark pink, easily half an inch tall, and as big around as the tip of my finger. Areolas about three inches in diameter, and slightly lighter in colour, surrounded them. A sprinkling of freckles adorned the rounded curves that led down into her cleavage, but faded on the outer portions of each breast. I touched her again.

"Damn, those are absolutely beautiful breasts, Dorothy!" I offered.

"Thank you for the compliment." she replied. Her voice was very shaky, and she was breathing raggedly. "Two more". She smiled.

Well, the next logical step is...? I leaned in and took a nipple between my lips. The moan this time was clear and loud. It got louder as I sucked the bud in, circling it with my tongue. I continued to fondle her other breast, while I furiously suckled this one. Then I switched. Dorothy started to squirm a little, in addition to her moans of pleasure. Her head was resting back against the roof support of the cart, and she released her shirt, placing her hands instead on the back of my head. A few more seconds, and I heard her say, very quietly. "Oh god... One more."

For my last round, I lifted my face away from her chest, and brought it up even with hers. I brushed my lips over her lips, and her tongue speared my mouth eagerly, which led to about two minutes of feverish tonsil hockey. Her shirt was still pulled up above her boobs, and I was still fondling them mercilessly, but she didn't seem to care. As we broke the kiss, she looked at me and firmly said. "Okay, let's play golf." and pulled her shirt down. She was still bra less, but at least covered.

The activities of the last few minutes had left me with a severe handicap, namely a full blown hard-on that verged on painful. It did not go unnoticed by Dot.

"I don't suppose you want to whip that thing out and show me how you jerk off to visions of my body?" she asked suggestively.

"I'd love to, but you are going to have to earn it." I responded.

"Fine by me" she retorted.

Dorothy won the par 4 eleventh with a bogey. My concentration was compromised, not only by the visions I had running through my mind, but by the sight of her bouncing and jiggling around without her bra. She had been provided with an unfair advantage by my own hand, and she intended to use it fully.

"Drop 'em" was all she said. I complied, unbuckling and unzipping, until my pants and underwear were around my ankles. My erection, nearly 8 inches long and as thick as Dot's wrist, stood straight out. Dorothy conducted a close range visual inspection, but didn't touch me. I could feel her breath on me, but she knew she'd need to win the right to touch, just as I did with her breasts.

After winning the twelfth, she merely looked at me and made a jerking motion. I merely looked at her, put my hands to my chest, and cupped an imaginary rack. She pulled her shirt up again. Then she gestured to me again, as if to say 'your turn'. I tried to look like I was embarrassed, but excitement had overtaken embarrassment a few holes ago. My cock was like steel, and I would have probably been tugging on it whether she had won or not. I wrapped my right hand around my shaft, and began to stroke it slowly. I looked at her, first in the eyes, then very deliberately dropping my eye line to her exposed orbs. She cupped her tits, holding them out for me, as she moved closer. I stroked faster. I was beginning to grunt with excitement. Dorothy was moaning herself, from watching me, pulling on her nipples, and her fingers that had begun to rub her crotch. After about a minute, and just in time, she sighed and said "Okay, that will do". I stuffed my dick back in my pants, and she pulled her shirt down. We drove to the tee of the par 4 thirteenth hole.

When she won her third straight hole, she had her hand on my cock, doing the jerking herself. Somehow, I was having a hard time thinking of this as a loss. I was hardly suffering. It was a beautiful day, and I was on the golf course. By itself, that would be a good day. Add to it the fact that a beautiful, topless, huge breasted girl was wanking my hard dick, and I was getting closer to cumming. Wow. She could feel that I was close to cumming, and she stopped.

She was now only three down, and one shot ahead of me overall.

"You know, it has just occurred to me that you might be throwing this match, to get me to continue playing with your cock." she said.

As if to prove her wrong, I put my 6-iron shot on the par 3 fourteenth hole in to 12 feet. Dot almost holed hers, the ball finishing less than two feet behind the cup. I conceded hers, and when mine curled in the top edge, we had halved the hole with birdies. We each got a bonus.

Dorothy sighed. "What's it going to be?"

"Your panties, please" I said, holding out my hand. She actually grinned as she deposited the tiny garment in my hand. They were wet. Very, very wet.

"And here's what I want" she smiled as she tugged me over to the cart and took a seat. She spread her legs wide, and pushed me down between them. I really didn't need any further guidance. A puffy tuft of red pubes resided above her swollen labia. Her outer lips framed the inner ones perfectly, and the inner lips were long, protruding about an inch. They were glued together by her natural lubricant. Dorothy took her finger and ran it the length of her slit, separating her lips, which spread open wide. Pussy juice oozed from her gaping passage. At the top junction of her labia, her bright pink clit protruded, begging for attention.

"My god, Dorothy... You have a porn star pussy! It's gorgeous!" I said from between her legs She smiled and yanked her shirt off over her head, then placed a hand on my head. Her hips were undulating. I got the impression that, if I didn't get my tongue busy soon, she was going to scream. I took another look at her sexy cunt, then dove in.

Dot shrieked once, then put her knuckle in her mouth, trying to control her volume. I was tongue-fucking her good, licking her lips, sucking her clit, and spearing her with between one and three fingers. She was squirming with glee, and trying to maintain her grip on the cart, so as not to fall off the seat. Her breathing was rapid, ragged and loud. She was groaning, and the hand on my head pulled me closer. I pointed my tongue, and jabbed it into her now soaking pussy.

"Oh fuck,... Eat me!... Gonna make me cum, soon!" she hissed. "Please don't stop!"

I thought about being mean, and leaving her hanging, like she did to me when she was jerking me off. But I quickly dismissed the thought. I wanted to get her off, if for no other reason than to watch her orgasm. Also, she was delicious. Her honey tasted wonderful, and there was lots of it to be had.

"Oh... Uhnn... Fuck... Cummmmmmming!!" she groaned, and her body tensed.

Dorothy had been full of surprises today. I knew her tits were big, but never would have figured F cups. I had no idea that her nipples were so big and erectile. I didn't know she was such a playful, sexy slut. I couldn't have imagined a prettier pussy. And I never saw the squirt coming, or rather, cumming.