Par for the Course A Transgender Tale A Very Short Novelette By Tara Nicole Miller Copyright © 2024 Tara Nicole Miller All Rights Reserved. Word Count 7,800 Image from Adobe Stock: FILE #: 791166611

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Beautiful days are almost a given at Olympic Pines Golf Club. Even when it rains it’s gorgeous, unless you’re a caddy carrying thirty pounds or more of golf paraphernalia over two miles of hilly terrain. I’ve been caddying here for two years now, since I graduated from high school. It’s a full time job for me, although there’s a lot of downtime where there are no wealthy patrons who want my services. I get offers from them for other types of services, but I’m not one to indulge in sexual escapades.

I’m sure that half the time they think I’m a girl, and it’s not just because I have thick blonde hair down nearly to my perky bottom. The puberty fairy never visited me and it’s looking as if he never will. I’ve gotten used to my androgynous look over the years, so the prospect isn’t as painful as it used to be. I just wear shorts and the club polo shirt, size extra small, on my 5’4” frame. I used to have dreams of a golf career, but never getting muscles or growing to even an average height put the kibosh on that. But, I love golf so much that I’m very happy to caddy at such a lovely and exclusive club as Olympic Pines. And the tips aren’t anything to sneeze at either.

Things are pretty much the same here day after day, but I get to meet many interesting people, mostly men, and wildlife (not just the men) tends to congregate on the fairways. Just this morning there was a herd of deer on the third fairway. Nope, no gophers at this golf club, sorry Bill Murray. Things were going according to Hoyle until Joshua Stern showed up one day. He had just sold his popular social media app for an obscene amount of money and was apparently looking for a hobby to fill his now empty calendar.

“I’m told you’re the best caddy at the club and even give a lesson to kids now and then.” He said to me, without introduction.

“I’m okay,” I deprecated. “I love my job, I know that much! Lindsey Gardner at your service (my parents were Fleetwood Mac fans, even if they spelled my name wrong).” I smiled and offered my hand.

“Don’t sell yourself short,” he said. “You need to have confidence, or you’ll get nowhere in this world.” He sermonized. “Stand up straight. Stick your chest out.” O-kaay, this guy’s kinda weird.

“Yes sir.” I obliged. You always nod and agree when your tips depend on it. “How can I help you…?” I asked, hopefully prompting for a name.

“Joshua Stern.” He provided. There we have it. “I need a caddy, and one that can teach as well. You would fit the bill, if you meet my exacting requirements. I will pay you $500 today to play a round of golf with me, choose my clubs, read the breaks, critique my game play. If you pass muster, I would put you on retainer for $1000 per week. How does that sound?”

How does that sound? Are you kidding me? That’s double what I get caddying two rounds per day all year round. “That sounds amazing, sir.” I replied. “Shall we go get a tee time?”

“No need, they’ll let me in when I’m ready. Let’s go hit the driving range.” He insisted. Wow, this guy’s got a lot of balls. And not the little white dimpled kind, either.

So he was hooking and slicing all over the place and I adjusted his stance and his hand placement and things started to straighten out. I took notes on how far he hit the ball with different clubs, etc. “I think you’re getting the hang of it sir.” I told him.

“Thanks to you. You’re already paying off. And call me Josh, okay? We’re not in the boardroom.” He snickered.

“Yes sir, I mean Josh.” I blushed.

“Okay, I’m warmed up, let’s go hit the course.” He prompted.

On the first tee, things started getting weird again. He said, “If this is going to work, I’m going to need you to dress more appropriately.” I looked down at myself, wearing the same shorts and polo I always wear, and shrugged. He continued. I don’t go for the slacker vibe these days. Girls always wore dresses or skirts and had their hair up in a visor cap.” Why was he telling me this? It’s true enough, though. Lots of women players are now wearing pants and shorts instead of the cute outfits they used to wear in times past. “And a little makeup wouldn’t go amiss. Gotta put your best foot forward. Make a good impression. That counts for a lot in this dog eat dog world. Okay, kiddo, I’m up first.” It was a long par four and his distance wasn’t that great yet, but we’ll get him there. He did hit it down the middle of the fairway, but he was a long ways back from the green.

“Well done sir.” I told him.

“Josh. Yes, thanks to you. That’s probably the best drive I’ve ever hit.” He said. “Okay , you’re up. Let’s get you up to the women’s tee.”

“Why?” I asked.

“Well, that’s the way it’s done, isn’t it. You can’t hit it as far, that’s why it’s there. Go use it. Don’t go easy on me now. I wanna know what I’m dealing with.”

Okay, if that’s what he wanted, I wasn’t going to argue. I always have trouble with this hole because of the length. Gaining thirty yards will be a nice change of pace. Maybe I can finally birdie the darned thing. So I addressed the ball and smashed it fifty yards past Josh’s ball. All he could say was “wow!” Wow indeed. That was kinda fun. I think I’m gonna like the women’s tees. I only have 150 yards left into the green, so I have a good shot at getting it close to the pin.

I took the opportunity to give him some advice on his approach shot. “Now, the pin is back right, so you want to fade it in from the left. It goes uphill from front to back, so don’t worry about the roll out. Your three-iron should do the trick. Now, to fade it, bring your hands in and take a weak grip, that’s counterclockwise on the grip, okay?”

“Gotcha.” He took a couple of practice swings and I complimented him. That caused him to smile, then he bore down and let ‘er rip. I’m not kidding, that thing faded perfectly between the bunkers, bouncing in front of the green and rolling toward the hole nicely. I couldn’t have done it better myself. Beginner’s luck, I thought. He was only ten feet away below the hole - so, perfect. He was in shock. Well, truth be told, I was, too. “Wow,” he said, “You’re a great teacher. I’ve never hit a shot like that before. You keep this up and you’ve got yourself a job.”

Well, knowing this course as well as I do, I knew how his putt was going to break, and it was uphill, so I had him adjust his practice strokes to match and he poured it right in. I was golden. Omigod, I’m gonna feel so rich with his retainer! So, it went like that - well, not always so perfectly, but he had a decent round after birdieing the first hole - he scored an 85. “Beat my best by ten strokes!” He admitted.

“Well done Josh!” I enthused. I scored a 70, which was my best score ever on this course, mainly because I got to hit from the women’s tees.

He walked up to me with his hand outstretched. “I’d say you’ve got yourself a job!” He said, shaking my hand, then pulling me into a hug. “That was simply amazing! You are amazing!”

“Thanks Josh,” I blushed down to my little Nike spikes.

“So, tomorrow,” he began, “I’m gonna get you some proper attire in the pro shop. Be here at eight, then you can change and we can do it all again. I think I wanna play one more round with you before you caddy for me. Is that alright with you?”

“Yes sir,” I reverted. “That’s very alright with me,” I smiled. I get another $500 plus some new clothes. That’s very very alright!

He handed me five $100 bills and patted me on the shoulder. “See you bright and early then.” He said and whistled his way toward the pro shop. I still had time to caddy for another patron. This is gonna be the best day ever!

This one guy saw me with Josh, so he was anxious to get me to caddy for him. “I saw you with Mr. Stern,” he said. “You were spectacular, young lady.” Wonderful. He thinks I’m a girl, but the patron is always right, so…

“Thank you sir.” I said. “Would you like me to caddy for you?”

“Oh, yes! I’ve been looking to up my game and I think you would be perfect. Should we give it a go?” He asked.

“Yes sir.” I said, grateful that I wasn’t going to be playing this round. It takes a lot out of you when you’re essentially playing two rounds simultaneously.

He had already hit a bunch of balls on the range, so we went straight to the first tee. He was doing everything wrong, so I gave him some tips. He still hooked it into the rough, though. He’ll never make it to the green from there. This guy wasn’t going to be as easy as Josh. I kinda felt a tug toward the women’s tee. As grateful as I was to not be playing, there’s this siren song that calls to you, to tee it up, to rip it down the fairway, to get it into that little cup. I could feel my forearms twitch. But, this was Mr. Fairbanks’ round. I need to try to get him up to snuff if I want a nice tip.

I was disappointed that he ended up with a 105. That’s just horrible. 33 over par. But he comes up to me and says with a smile, “Beat my best by five strokes.” You’re kidding me. “No kidding! You, my dear, are worth your weight in gold.” I wonder how much 105 pounds of gold is worth? I giggled to myself. I did a quick calculation - that’s over $4 million! Okay, hotshot, pay up! Giggle.

So, I went home with $1000 in my pocket! I never made $500 for a round in my life, then it happens twice in one day! Thank you Joshua! I went to my favorite Mexican restaurant and got the shrimp on rice dish that I’ve always wanted to try. It’s $20 so I never felt I could afford such an indulgence. And it was worth every penny. I even got two glasses of Pepsi^TM, which I never do! I felt so rich! I walked back home and had the best night’s sleep I could remember.

I was excited to greet the day ahead of me. Another $500 and hopefully payment of the retainer. I may have to ask him about that. I made a bagel with cream cheese to jump start the day. A cup of coffee got me all the way to take-on-the-world mode. So I jumped in the shower and washed and conditioned my hair. I didn’t dare skip a day when I’m seeing Joshua - he would just read me the riot act. Don’t want to risk this set-up for anything.

#

I got to the club at seven since I would be meeting up with Josh at eight. Maybe he’ll be early and we could work on the driving range and practice putting. I just wore my regular attire since Josh was gonna buy me some new threads so I don’t look like a ‘slacker.’ Jeez, it was always good enough before. He sure is a stickler. I guess hundreds of millions of dollars will do that to a guy. You can get whatever you want. Why not have it just right?

Josh pulled up right after me and he got out with a box in his hands. “Good morning Lindsey. Got your outfit for you!” Who calls it an outfit?

“Cool. Thanks Josh, and good morning to you too!” I enthused, reaching for the box.

“Just go ahead and change and I’ll meet you on the range in a few minutes, ‘kay?” He said with a stern expression. ‘Stern,’ get it? Giggle.

So I skipped to the locker room, sat on a bench and opened my box. The fabric was pink! Not shocking pink, but it was pink nonetheless. Oh well, he’s the boss. So I pulled out what I thought was going to be a shirt and it just kept going. It was a dress! Omigod, he so totally thinks I’m a girl. What am I gonna do? I can’t wear a dress! So, I went back out to talk to Josh. But, what if he doesn’t want me after I tell him I’m a guy, or that I won’t wear the dress? Oh god! The money!

Well, they say that money talks, so what I did was turn around. I went back to the locker room and sat on the bench, trying to work up the courage to put on the stupid dress. It was cute, though. It had the Olympic Pines logo on it and everything. But I’m a guy! Gaah!

I decided I better go into a cubicle to try on the dress. I didn’t want anyone to see me if it was totally ridiculous. Of course it’s going to be ridiculous, but at least they won’t see me putting it on. I was glad that I wear tightie whities as I pulled the dress down over my hips. It didn’t look like you could see my underwear through the fabric. God, I can’t believe I’m even considering this. What’s wrong with me? Oh, yes, money is what’s wrong with me. The root of all evil and all that. But this isn’t evil, right? It’s just embarrassing. I could live with a little embarrassment in order to live comfortably, right? Gack!

After I got the dress all sorted, I pulled my hair up into a high ponytail and put on the cute visor that Josh also provided. I then put on my size five spikes and was glad for the first time that I have small feet. Okay. I still haven’t heard anyone else in the locker room, so I cracked the door and peeked out. The coast was clear, so I snuck out to look at myself in the mirror, bracing for the horror. But, what I saw was a girl! A cute girl! What the heck? I actually had hips, and the built in padded bra gave me a little up top, so I actually looked… for the first time in my life I actually thought of myself as attractive. But, as a girl! I was getting really confused.

I then heard a couple manly voices head into the locker room and I froze. I thought I was going to pass out. The voices quieted and one of them said, “um, sorry young lady, but you have the wrong locker room. The ladies’ is across the hall.” I’m sure I turned beet red.

“Oh! Sorry.” I said, and quickly made my way out the door and into the lobby. I sat on the edge of a big fluffy chair in order to gather my breath and my wits. Josh is going to be waiting for me. I need to get going, but everyone is going to see me like this. But would anybody really see a boy in a dress? To me, I looked totally girl, so maybe this wouldn’t be the nightmare it seemed to be. So, I got up and slowly made my way outside, peeking left and right and looking for odd reactions or screams of ‘lookit the boy in the dress’ and all other sorts of nightmare scenarios. But, none came.

Josh was on the practice putting green and he looked up after a particularly bad putt. Something new to work on today. He saw me and smiled. He actually smiled upon seeing me! I relaxed just a little and made my way over to him. He said, “ahh, that’s a perfect fit. I knew you’d look good in proper attire. Now we can get down to business.” He glanced at my legs and then back up to my face. “Don’t you shave the peach fuzz on your legs? You girls nowadays!” He shook his head. “You’re gonna need to shave that and put on a little makeup for pete’s sake. And I can see your panty lines. Don’t you have proper underwear, either?” I blushed profusely. He went on, “Golf isn’t just a game; it’s a chance to make business connections and you’ve gotta look good. First impressions and all that. Please, for tomorrow, be shaved and have at least a little makeup on.” I swallowed the lump in my throat and just nodded.

“Yes, Josh, sorry. Is there anything else?” I don’t know why I asked that. It’s like I’m inviting more of this strange makeover.

He looked me up and down. “Just, those socks don’t really look right. Maybe wear those kinds that don’t show? Those really short ones? And maybe a ribbon in your hair. I always thought that looked cute with a golf outfit. That’s just a suggestion, though.” I was writing all this down in my yardage booklet. Didn’t want to mess up again. There’s a lot of money riding on this.

“Gotcha.” I said. “Are you ready for some putting tips, or do you want to hit the driving range?” I asked.

“Putting is where my game went south yesterday, so let’s start there.” He said with authority. I nodded and reached into my bag to grab a bunch of balls. I tossed them all around the green and we began. I straightened out his stance and stroke and then told him how to read the greens and the specific foibles of this course. How most putts break towards the creek in the valley, that sort of thing. Then we warmed up on the driving range. I had to readjust him after he went back to some of his old habits, but then we were ready to go.

I had to make sure to bend at the knees so I didn’t show off my inappropriate underwear. Otherwise, the dress was actually way more comfortable that my normal clothing. I think it helped me shave two strokes off my handicap. I could get used to this. His putting was much better this round. I helped him read his putts and he was almost to the point of being able to do it himself by the end of the round. He scored an 80 this time. “At this rate, I’ll score a 59 by the weekend.” He enthused. “You really are a miracle worker Lindsey.”

I blushed and giggled, “Thanks, Josh. But you’re an awesome student. I don’t think I’ve had anybody pick up on my pointers so quickly.”

A group of well dressed men gathered around as we came off the 18th green. They were all clamoring for my services. I joked with a big smile, “Okay, I’ll caddy for the highest bidder.” Then one guy actually bid $1000! I was only joking, but, what the heck. He bid the highest and he was actually the youngest and cutest of all the guys. Did I actually just think that? Must be the dress. Weird.

On the first hole, he squeezed my butt as he was going up to the tee box. He actually squeezed my butt! I was about to protest, but then I thought about all that money and zipped my lip. As long as he didn’t take me behind the bushes, I could put up with just about anything. So, I didn’t have any yardages for this guy. His name is Matt by the way. I had to build this plane in midair - guessing his yardages by the length of his first drive, which was 250, just like Josh’s was at first. But, this guy wasn’t as big or fit as Josh, so I figured I would go one club longer on each of his intermediate shots. That worked a charm. And his posture and grip was all wrong, so I adjusted that right away and he did a bit better. Wasn’t as quick a study as Josh, but who is? Josh is one of a kind. And he hasn’t pinched my butt even once!

Anyways, we get done with Matt’s round and he tells me that he did twenty strokes better than he ever has? OMG! He shot a 95, and that’s his best? He’s gonna need a lot more practice with the new techniques I gave him. I don’t know if I wanna teach him anymore after all the pinching and flirting he did. This guy was incorrigible! But it did make me feel pretty good about how I must look. I was desirable in a way, I guess. And I kinda liked it. I never felt desirable before. I’ve never had a date in my life, so… yeah, not the most masculine of dudes.

I was kinda scared to go into the lockerroom when we were done, after what had transpired earlier; so, I just wore the dress home. I would change there. So, I get home and immediately strip to take a shower. I took a good look in the mirror. I guess my body is a little feminine. I never considered that before. I always just thought of myself as a tiny skinny dweeb. But, in that dress…

After my shower, I put on my regular daily uniform so I could go get something to eat, and I guess some makeup and socks, too. My outfit felt kind of off now. I had lost some of the confidence I had built up throughout the day. So, that’s weird. I just looked wrong now, and yes, slackerish. Josh was right, after all. Why do I keep thinking about him? Must be the money and the weird stuff he has me doing. That dress was really comfortable though.

So, I first went to YouTube to watch a couple makeup tutorials. I had only worn makeup once, like ten years ago, when my friend Janie got me ready for Halloween. I was super little then and really did get tons of candy for my efforts. Lots of ‘cute’s and ‘awww’s too. I blushed thinking about it. Armed with knowledge from the tutorials, I made for CVS. It cost me around $100 for all the makeup and some girly razors, but that was a small price to pay considering I just got paid $2500 today. That was lawyer-type money! Well, almost. And I get paid all that to do something I love in the most beautiful setting imaginable. I couldn’t believe my good fortune.

I had to go to Target for the socks, panties, and ribbon. I thought, since I looked so cute, I might as well try for the ribbon as well. I actually got a cute scarf instead of a ribbon - that should look really nice. Maybe it’ll help me rake in some extra cash. Who knows? Lordy, I’m like prostituting my masculinity for cash. Not that I ever had any masculinity. Sigh. Well, as if that weren’t enough, I even bought another golf dress and two sports bras. This was quickly getting out of hand, but I didn’t want to have to wash my dress out every night, so…

The evening was quickly waning, so I grabbed some McDonald’s and ate it in front of the TV, watching a rerun of the day’s LPGA tour. A lot of them were dressed just like Josh said, and I figured I could give most of them a run for their money. Did I just compare myself to other girls? Other? Oy! Well, they sure looked way better than the women wearing pants. That’s just so wrong. I guess I’m a convert to the Stern method. Giggle.

I got up early the next morning, so I would have time to shave my legs and armpits and do my makeup. I have no hair on my face, so I figured I didn’t have to shave that bit. Also, I didn’t feel like washing Josh’s dress last evening, so after getting all silky and smooth, I put on the new one I bought at Target. I think I’ll buy a few more from ThredUp^TM tonight, so I’ll have more choices and won’t have to wash as often. I don’t know how often Josh was going to be golfing, or when, so I’ll probably just have to wear a dress every day just to be safe. I wasn’t as sad about that as I probably should have been. I did look quite good in them after all. It’s cool that club management hasn’t said anything about my new attire - that could be an awkward conversation.

#

I walked to the club wearing my same old trainers and thought that I might want to buy a couple more to match my outfits. Okay, I’m definitely losing my mind here. Why would I need more than just my white ones? But, it would be so much cuter if they matched. Gaah! I wondered what it says about me that I so willingly feminized myself for Josh. Well, no, I feminized myself for the money, there’s a big difference. But still, how many guys would have done it for any amount of money? I bet they would have asked for a lot more before they went as far as I have. But, then again, most guys wouldn’t look as cute in these dresses as I do. So there!

Funny, as soon as I got to the club, I saw Mr. Bell, the president of the club, and he walked up to me with a big smile on his face. Good lord, what is happening? He reached out his hand to me. “You’re making a lot of people around here very happy young lady.” He said as we shook hands. Wow, even he thinks I’m a girl! That’s a relief, I guess. “Keep up the good work. You may win caddy of the year at this rate.” He smiled and I returned it with one of my own.

“Thank you sir.” I said, and he was gone. Must be a busy guy.

Then the head pro comes out of the pro shop. Now what? He saunters up to me, looking around like he’s CIA or something. “What did Mr. Bell want? Everything okay, Lindsey?” He said, looking me up and down. “You look nice, by the way.”

“Thank you, David. No, everything’s fine. He just wanted to tell me how happy he is with the job I’m doing. He says I may even win caddy of the year! I didn’t even know that was a thing.

“Yeah, it is, and we’ve gotten several comment cards from people you’ve caddied for and the reviews are very good. Well done. Must be your change in attire? Did I say you look good?”

I giggled. “Yes you did David,” I grinned and gave him a little smack on the shoulder. “Yeah, Josh Stern was the one to get me started. He said I needed to make a better first impression, so I guess I have.”

“And second, third and fourth impressions as well, I’d say.” David added.

“I guess so.” I said as Josh meandered up to join us in front of the pro shop.

“Hey Lindsey! I like your new dress. It really suits you.” Josh said with a big grin.

“Yeah, she looks good, doesn’t she?” David enthused.

“That she does, but that’s not all.” He looked me in the eyes. “Lindsey has come out of her shell, too. She looks happier and she’s more conversational that when we first met. See? If you look good, you feel good, right?”

“Yes sir.” I blushed.

Josh said, “I’m having trouble getting her to stop calling me sir and mister, though. She’s a tough nut.”

“I don’t know about tough, but I’m a nut alright,” I joked.

“See? She’s a new woman!” Josh said. Oh, you have no earthly idea how new, Mr. Stern!

I had switched to the ladies locker room, just to avoid unfortunate confrontations like the other day. I hope the girls don’t mind. It’s not like I’m being creepy and staring at them or anything. But I do like to see what they’re wearing, so maybe that’s weird. I don’t know. So I went in to get my spikes, so I could go up and down the hills easier. I’m not playing today, at least not this morning, so it’s not like I need them to stabilize my swing or anything. I’ll just be carrying Josh’s bag.

“Where are your clubs?” Josh asked when I met him at the putting green.

“I thought I was just caddying today.” I explained.

“No way! Playing with you is inspiring and I learn so much. It’s fun to watch a pro as I go puttering along.” He said.

“I’m not a pro,” I told him. “I’m just a caddy.”

“Why in the world aren’t you a pro? You sure play like one, and your teaching is top-notch.” He related, causing me to blush again. He’s always doing that.

“I was just never good enough. Even in high school, I lost to everybody.” I lamented.

“Well, you should try again. You’re obviously better than you were, if that’s the case.” He said earnestly.

I suppose I could try to get my card. I never even tried after my high school experience. ‘Course, I wouldn’t be playing from the ladies’ tees for that. I wouldn’t really stand a chance, would I? So, I told him, “I’ll think about it.” Even though I wouldn’t. I knew I was too weak to make it. Sigh.

I went back to get my clubs and met Josh back on the greens. We worked on his putting some more, then headed to the driving range. He was working on increasing his club-head speed, so he was now nearing 300 yards on his drives, with pretty good accuracy. At this rate, he wouldn’t need me for much longer. I told him so.

“I like playing with you,” he said. And I just like seeing you every day. You brighten my day, you know that? Since I sold my company, I don’t have a lot of personal interaction and you’re way better than anyone I had there. ‘Course, this is more fun than troubleshooting apps and managing 100 people. That was a nightmare. So when I was offered a giant golden parachute, I jumped.” He grinned. “Plus, this game is kinda, I don’t know, not relaxing exactly, but there’s a lot of in-between time. I’ve had a dozen new Ideas just this week. I could start a new company, that is if I get bored, or you get bored with me.” He looked at me with narrowed eyes.

“That’s hardly going to happen,” I said. “I like playing with you too. And you soak up lessons like a sponge. I have a feeling we’re gonna be on a par pretty soon and we’ll have to start wagering to make it interesting.” I quirked him a smile.

He said, “How ‘bout we start today? I bet you a new dress that I will tie or beat you.” He grinned.

Well, I didn’t figure I could lose that bet but I asked anyway, “And If you win?”

“You let me take you out to dinner.” Oh shit. This was quickly getting out of hand. I mean, I have absolutely nothing to wear for a dinner out with a man who thinks I’m a woman. Ummm.

“I’m sorry, but I really don’t have anything nice to wear for going to dinner. Thanks for the thought, though.” I sighed. I never get to go anywhere nice.

“Well, then we’ll have to go shopping, won’t we?” He offered.

“You really think you’re going to beat me, don’t you?” I said.

“Yes.” He said seriously. Well, that’s nice. He’s overconfident. He’s not that far along. At least I’ll get a new dress out of it, though.

“You’ve got a deal!” I smiled and we shook hands.

So anyways, on the first tee he wiggles his butt at me while he’s addressing the ball. I got a little distracted and had to shake my head to get back in the game. He’s got a nice butt, what can I say? He then ripped the ball 300 yards down the center of the fairway. There’s no way I can reach that, even with my extra 30 from the ladies’ tees. I’ve taught him too well.

I then get up to my tee box and he comes up in front of me, talking about the weather, how it’s so warm and all that. Then he lifts his shirt to wipe his forehead, revealing a perfectly chiseled six-pack. I just stared at it and felt my flat and soft belly. He was still saying stuff, but I have no idea what it was. He finally said, “Lindsey, hellooo! Are you going to tee off, or what?” He grinned.

“Umm, yeah.” So I addressed my ball and proceeded to hook it into the deep rough about 200 yards down the fairway. Great.

It went on like that for the next four hours; him cheating by distracting me, and me duffing the ball left and right. We were tied at 75 going into the 18th. I kinda wanted to go out to dinner with him, but I’m not gonna throw a match for a dinner. My momma raised me better than that. I had every intention of beating him on this final hole. “What if we tie?” I asked.

“Then I guess we do both, dinner and two dresses!” He grinned, way too happy at the prospect.

So I get to the tee and he says, “What if I told you I love you.” I choked, literally. This was a new low, even for a man that’s been distracting me all day long.

“That’s not fair!” I screeched. “Or funny.” I added

“It’s not funny, because it’s true.” He said flatly, looking into my eyes with unwavering contact.

Okay, breathe. Don’t let his silliness get to you. God, he really wants to win this and I’m not gonna let him. I took another breath and calmed my nerves, closing my eyes and picturing my shot. I haven’t taught him visualization yet, so I still have a little advantage over him. This last hole is a reachable par 4 if you’re a long hitter, which I’m not. Did I say? He gets up there and rips a low screamer that must have rolled forty yards onto the edge of the green. Holy mother of god! I am so screwed.

So, my turn, and I just hit my normal 250 to within about fifty yards of the green. At least it was on the fairway this time. I’ll have to have a nice pitch to win this hole. His ball is in perfect position for an easy birdie. We were silent on the walk up to my ball. I grabbed my sand wedge. I wiggled my club and my butt, feeling my little skirt swish around my thighs. I kinda liked that feeling. Now, since the green tilts down from front to back, I planned on sticking it past the hole, with enough spin to bring it up the hill toward the hole a little bit. I would leave myself an uphill putt for birdie. What I didn’t plan on was for it to whip back, hit the pin and go down! An eagle! I’ve got it in the bag now.

He had a fifty foot downhill putt with five feet of break to tie me. He asked me to help him read the putt, and since that is what he was paying me for, I obliged. I didn’t figure he’d get within ten feet anyway. The unfortunate thing is that, just that morning, we were practicing long putts. No matter. This was in the bag. Anyways, you can probably guess the improbability of the fact that he sank the damned thing! We tied at 77! Two eagles on the final hole? Impossible. But here we were.

But, that’s not the strangest thing. He proceeded to grab me around the waist and spin me around in glee. “Dinner and two dresses!” he crowed. “Let’s hit the mall!”

“But I’ve still got another round to caddy. I won’t get off till around five.” I said. “Sorry, it’ll have to wait.

He says, “Here. Here’s your payment for the day, plus another five hundred. Still have to work?”

“That’s not the point.” I shook my head. “This is my job. I’m supposed to be here. Sorry, you can’t have me all to yourself.” I was actually kinda sad about that, for some reason.

“Okay. I’m actually impressed by your principles. Another thing I love about you.” He said earnestly. God, I wish he’d stop throwing that word around so casually. I did get all squishy gooey when he said it though. “I’ll just hang out in the 19th Hole with my laptop. I have a million ideas bouncing around in my head. Come by if you get a chance.” I agreed and made my way to the front of the pro shop.

#

Matt was standing there, chatting with a couple of other guys. I sighed. More butt pinching. The money’s good, though. “I’ll be right with you guys. Hafta hit the little girls’ room.” I said, with a little too much ease.

There were a couple other women in there and we exchanged ‘hi’s and ‘hello’s. I peed and tucked and checked my makeup. I still looked pretty good, but I touched up my lips and powdered my nose. I was getting a bit too shiny.

Matt placed the highest bid again, so I steeled myself for more sexual harrassment. Small price to pay, I figured. I didn’t have to wait long. Again, on the first tee, after I adjusted his grip for a straighter drive, Matt pinched me as I went to stand off to the side. Unfortunately, I squealed and giggled. Well, that’s only going to encourage him.

Just a few minutes later, as I was teeing my ball, who shows up but Josh! What was he doing here? “You pig!” He shouted at Matt. “I’ve been watching you through that window over there.” He pointed toward the 19th hole. “If you don’t apologize to the lady, you’re going to regret it.” He said.

“Josh, you don’t have to…” I tried to interject.

“Do it!” Josh demanded.

“Or what?” Matt countered.

“Or I’ll beat the ever-loving crap out of you. Would you like that?” Josh said.

Matt looked Josh up and down, sizing him up and came up wanting. He looked to me. “Sorry, Lindsey. I was just having a little fun. You didn’t mind, did you?” Omigod, what a flipping jerk! I harrumphed and turned away from him.

“The lady has spoken. She minds. And I mind. For god’s sake, she’s carrying your bag, she’s teaching you how to play golf, so show her some goddamned respect! So, try again. Apologize to the lady.” Josh insisted.

“Oh, Just fuck off!” Matt said and began to walk away, grabbing his bag in a huff.

“My money!” I squealed. God, I am such a mercenary. Is that all I can think of right now? Well, yes.

Josh grabbed Matt’s collar. “Not so fast! You’re gonna pay the lady whether you play or not, so open your wallet.”

Matt turned around in a rage, but then looked up at Josh and thought better of it. He opened his wallet, counted out eight $100 bills and threw them on the ground and walked away. Wow. What a jerk. But I got my money. I turned to Josh and hugged his chest, tears beginning to flow. “Thanks Josh. You didn’t have to, but thanks.”

He placed his hand on my cheek and ran it down to my chin. “You don’t need to put up with assholes like him.”

“But the money…” I began.

“No amount of money is worth you self respect, surely.” He said softly.

“Easy for you to say.” I said.

“You’re right, of course. I’m sorry I said that. So, do you need to find another golfer to caddy?” Josh pivoted.

“I should, but I am sooo done for the day! How ‘bout I buy you a drink instead? ” I said. “It’s the least I can do for my knight in shining armor.”

He smiled. “I think I may take you up on that.” He grabbed my hand, engulfing it, and I let him lead me to the 19th hole bar and grill. We sat down at the table that still held his laptop. “You’ll have to order it,” I said. “I’m not old enough.” How embarrassing.

“Oh, well, okay, what’ll you have then? “ He asked.

“I’ll have an Arnold Palmer. Tastes better than alcohol anyway.” I grinned.

“That it does.” He ordered our drinks and grabbed my hand across the table. “I’ve really enjoyed working with you and getting to know you.” He said. “Could I take you out on a date?”

“You know? I think you could.” Oh shit. I forgot I’m not really a girl. He’s not gonna like what he finds down there.

He must have read the expression on my face, because he then said, “Relax, I don’t bite.” And he smiled that beautiful smile. “Much.” He added and I couldn’t help but giggle.

As we walked out to his car (in order to go shopping!), he said, “I don’t want you to worry. I’m aware of… your history, shall we say?”

I gulped. “Wh-what do you mean, history?”

“Well, old habits die hard,” he began. “I did a background check on you before we started our… relationship. Our golfer/caddy relationship I mean. Someone in my position can never be too careful.”

“You knew before?” I was shocked.

“Yes, and I also knew that, despite what the documents say, you are all girl.” He squeezed my hand.

“Well, not all girl.” I whispered.

He waved his hand as if to swat away the idea. “Oh, that doesn’t matter. Really. That’s the least of what this life has to offer. And I like what you have to offer so far. I’d like to get to know you even better, so now, knowing all that, I’ll ask again. May I take you on a date?”

“Oh my god, yes!” I squealed and leaned in for a kiss. He obliged. Omigod, his lips were so soft and tender and his kiss so gentle. He tickled my lips with his tongue, then pulled back, looking me in the eye.

“So, shall we go?” He asked.

“Oh yes, we shall.”

#

We got along famously, and the love-making was spectacular, too. Who knew? I moved in with him after two months and quit my job, because we were golfing together several times a week anyway. He got to where he could beat me regularly and I hardly cared - he’s twice my size after all.

It didn’t take me long to get used to his gigantic house. Our gigantic house, now. I was thrilled to get out of my studio apartment and have some room to stretch out. He had tons of books, so I began reading in our down times. I was never much of a reader before that. Turns out I love Jane Austen! Why he had her books, I don’t know, but he is an old softy. Maybe he just likes classics, because I found a bunch more, including ‘Little Women,’ which I also loved.

My breasts were growing nicely and he was fondling them as we sat in the hot tub, watching the sun rise above the mountains. “So, do you want a June wedding?” He asked.

June is the perfect month for weddings around here, but I wanted to wait until I had my surgery. So we could, you know, consummate. Blush. “My surgery isn’t until next March and I’d really like to be complete for our wedding day. I don’t want that, thing, under my beautiful white gown.”

“I get you,” he said. “That’s okay. Next June then.” He smiled, giving my nipple a little pinch and making me squeal.

I was totally healed by the time the wedding rolled around and I must say, my surgeon was a genius. I had the best orgasm ever on our wedding night. In fact, I had three of them!

A year later, I was allowed to enter the U.S. Women’s Open play-in tournament; apparently I had been on hormones long enough to make it legal. I still felt guilty, though.

“You know, most of those women are bigger and stronger than you. You really have nothing to feel guilty about. You are a woman and you deserve to be there.” Josh pointed out.

I smiled. “You make a good point. Okay. The regionals are next week, so I’ll do it!

“Good.” Was all he said, then he kissed me. “I’ll be there cheering you on!” I kissed him back.

Dang, those girls were good and I didn’t stand a chance. Some of them were hitting the ball 300 yards! Still, I decided to go to Q-school and get my card so I could be a golf pro. I really just wanted to do something for myself. Something I’d been dreaming of since I was a young girl. Yes, I can see my life in those terms now. It wasn’t very hard, looking back on it. I didn’t really make it as a boy and I was pretty damned girly truth be told. I have Josh to thank for making me realize it. Bringing the girl out of the shadows of my melancholy androgynous life.

I came out the door with the card in my hand. “It’s official,” I said. “I’m a pro!”

“I already knew that,” Josh said with a smile and a little kiss.

“Thank you.” I said.

He looked puzzled. “For what?” He asked.

“For seeing me, for believing in me, and most of all, for loving me. I love you, Joshua Stern.” What followed was a very long and passionate kiss. Please, close the door behind you.

The End