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Match Play Twosome

Category: Gay Male
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I stood on the tee box looking out across the 1st fairway, wondering where everyone else was on such a beautiful afternoon. High stratus clouds pulled long and wispy, a steady breeze, 72 degrees and low humidity. The many shades of green painted against the deep blue horizon looked crisp and brighter than usual. Hoping for an opening (I didn’t have a tee time), I had anticipated a long wait even though it was a weekday. But the parking lot was dotted with just a handful of cars. What a pleasant surprise to have the starter say, ‘The tee is yours! Hit ’em straight.’ This will be a great afternoon!

When I play alone, I play two balls, especially on a low traffic day like this. The luxury of enjoying my own pace of play adds to the day’s enjoyment. I keep score on the first ball (for my handicap, 11) and mark down the second for comparison. You get the picture, yeah?

I was playing very well – definitely above average. Through the 7th hole, I was 1 over with 2 birdies and 1 bogey. (and parred the second ball on that bogey hole) I was ‘in the zone’, playing as I imagined I would were I a scratch golfer. I was tempted to call one of my weekend golfing pals and brag a bit, but why jinx it? Balls seemed to explode off the club face with little effort. I’d reached 6 greens in regulation. My usual 25 foot target radius for approach shots seemed to magically shrink to 15 feet. And putting was, well, easy.

Pretty darn good for an overweight middle-aged guy. I’m from Irish heritage, 5′ 11″ 205 lbs., thinning blonde hair, trimmed goatee. My wife says my legs are my best feature, well-shaped and smooth. I’ve been called handsome – I’ll take the compliment. And a golf lover – I would play every day if my employment as an IT manager didn’t take priority. (My wife of 31 years would probably notice the lack of income) Before we’d met, I’d dated quite a few girls, and discretely fooled around a bit with a few guys, nothing serious. It was curiosity and fun, and I shelved that hidden part of my life once we were hitched. Over the years, the urge to fulfill my bisexual desires disappeared.

I teed off on the 374 yard 8th hole, a dogleg left with tall pines about 190 yards out protecting the left corner. This was a wide fairway with lots of space to bail out right, but that leaves a longer second shot to the medium sized, well bunkered green about 20 feet below the fairway. I hit the driver on my first ball, landing left center and rolling out to the far side of the fairway just short of the rough and cart path, about 245 yards.

Now – let’s see if I can turn the corner with my second ball, hitting the 3 iron from the shorter white tees.

Greedy me – I guess you know what happened next. Not quite a duck-hook, but my ball sailed into the pine boughs near the top of the tallest tree. I heard it hit something but didn’t see the ball drop. That’ll teach me.

I rode down the fairway, turned left past the trees on the corner and parked in the pine straw. There’s a collection spot behind the pines, a drainage gulley. Carrying my 8 iron just in case, I began looking for ball number 2. No luck – it probably ricocheted into the dense stuff. Oh well, I still have ball 1 in play.

As I started my cart back across the fairway, I glanced to my left – bingo! There’s my ball, about 15 yards ahead in the rough! I drove to it with a chance to get two balls on the green.

As I’m lining up the shot, I hear the sound of someone teeing off behind me. I couldn’t see the tee from my position. I backed off a few seconds and heard the ball land in the fairway about 30 yards down. Dead center. Wow, nice shot around the trees! I took a few seconds to get my shot aligned then hit it about 15 feet past the hole.

It was obvious that the guy on the tee couldn’t see me around the corner, so no harm, no foul. I was driving across to my first ball as he was coming up the fairway. I waited for him to approach but he stopped about 50 yards short, got out of his cart and yelled, “Sorry about that. Didn’t see ya.”

“No problem.” I waved him up.

He arrived as I was getting set to hit, sitting quietly in his cart. My wedge stopped about 10 feet below the hole, just past the apron. “Nice shot!”

I replied, “Thanks. Hey, no worries on your drive. I know you couldn’t see me. And THAT was a great drive!” I said, pointing to his ball.

“Thanks! You want to play together?” he asked. Darn. He didn’t realize I’m taking my time, playing two balls. And based on his drive, I’m thinking he’s probably a lot better than me. But on the golf course, I’m a social liberal. “Sure. I’ve been playing two balls, but that’s ok.”

“I don’t want to ruin your party, man…” he smiled. “How’re ya hitting ’em?”

Ah, a chance to brag about my round! “I’m playin’ way over my head. It’s such an awesome day out here, and I’m kinda in the zone, you know?”

“You sure it’s ok?” He looked like he was hoping I’d agree. I smiled.

“Yeah, it’ll be fun. I’m Brian.” He extended his hand, “Jack. Nice to meet you, bud.” He seemed nice enough and, strangely, kinda looked like me – over 50, same height and nice face, goatee, slightly heavier than me. We were even dressed alike, white on top, dark blue shorts. “OK, you’re up”, I said. “Hit a good one!”

He swept a beautiful wedge shot to about 7 feet, stopping on a dime. As we drove up, I said, “Nice! Someone’s looking at a birdie!” He noticed my two balls on the green and chuckled. “So are you!”

As I leaned over to pick up my second ball, he stopped me. “No, go ahead and putt it. You earned it.”

“Thanks, Jack.” Nice guy. I rolled my second ball a foot past the hole, and my first ball stopped on the edge, almost teetering in. I made both for pars, keeping the great round going!

Jack made his birdie. “Good putt! How’s your round going so far?” I asked.

He grinned. “Well, I’m doing great – I’m 1 over through eight, a lot better than my usual.” 

I laughed. “Really? I’m 1 over with my first ball, and that’s way better than my 11 handicap.”

Jack smiled. “I’m an 11 too. Let’s make a match of it!” While I’m not inclined to gamble when I’m certain I’ll lose, his handicap made it a friendly match that seemed harmless. “OK,” I said, “let’s play the 9th for a drink on the turn, and figure something out for the back 9.”

I failed to get up and down from the beach on the 9th hole, and Jack holed his 10 footer for par. Not a good start. We headed for the clubhouse, and Jack insisted on buying. “How about a beer?” It wasn’t too hot out and I had no place to be after, so I agreed.

“Great,” he said, “I’ll get it. You turn in your cart and we’ll ride together.” Sure, makes sense. Again, he flashes that big grin.

I strapped my bag to his cart then ran my cart to the shed. In the back of my mind, I thought that meeting Jack just made the day a little better. He was friendly, seemed like minded, and hey, we’re golfing. Beats working!

Jack picked me up and we headed to the 10th tee. “Grab your beer, it’s in the back.” I look over my shoulder at a small soft-side cooler filling the cart basket. I unzipped the lid to find it packed with ice and at least a six-pack, maybe more. Uh oh, there’s no way I can handle more than a couple.

“Jack, I appreciate the beers, man, but I need to be careful. And I don’t want to ruin this great round I’m having.”

“No worries, man. Let’s just have fun and enjoy the day.” OK, I can get behind that! “By the way…” He points to the front of the cart. “I figured you might be hungry, too.” He’d picked up a hot dog with mustard and relish, my favorite.

“How could you possibly know I like my dogs this way?” Now I was grinning.

“I didn’t, but I figured I’d get it the way I like it and if you didn’t eat it, I would!” We both laughed out loud as we headed to the 10th tee box. I’m beginning to feel something, maybe a bond? I’m very slow to make friends, so it was, at least, unusual for me. We took a couple of minutes to pop open a beer and inhale the dogs.

The back nine on this course heads out into the woods, with more undulations and tighter fairways. It’s laid out for future development so there’s a lot of untouched forest separating the holes that run 5 outbound, 4 inward. Many of the holes are canyon-like with the dense trees surrounding them. This creates some beautiful settings, with picturesque greens set against the darker woods behind.

We played the 10th hole even par, but I had to scramble. As we approached the 11th hole, Jack reminded me about our match. “Slipped my mind,” I lied. “What’re we playing for?”

“Well,” he said, drumming his fingers on the cart’s steering wheel, “I bought the beer and hot dogs, but that was my treat. What do you want to play for? We gotta do something to keep it interesting!” He said that in a sly way, and when I turned to him, he winked at me. 

He winked at me? Could he possibly know? I’d always been extremely careful not to show my buried inclinations, and had not had a man to man experience since before my marriage. No, he couldn’t know. There’s no way! But maybe HE was so inclined and was just taking a shot in the dark. Wait, maybe that’s what I was feeling a few minutes ago – his vibe? Could it be?

I needed time to think. “Let’s play this hole and give it some thought.” I hoped I’d said that without any hint of interest in what I supposed his plan might be. Jack replied, “No worries, bud.”

The 11th hole is a beautiful par 5, 530 yards straight away. Jack hit a low roping beauty about 260 down the left side. I followed with a shorter, loftier ball that floated down the center about 10 yards behind his. As we drove down the fairway, he slapped my thigh. “Great shot!”

“Thanks, you too…” I mumbled. OK, was I reading too much into this? This is crazy. I had to concentrate. In spite of the ‘vibe’ I perceived from him, I wanted to keep my game together.

I decided to lay up by hitting an easy 6 iron about 175 yards, leaving me a long wedge shot to the green. At least, that was the plan.

I topped the ball with just enough on it to advance about 125 yards. Damn it! Where the fuck did that come from?

Jack has obviously decided on the same strategy. He hit a beauty about 180 yards, right center, position A. Wow, I was beginning to worry about betting anything at this point! Were my wheels coming off, or what?

Then, as I watched Jack walk over and pick up his divot, long suppressed thoughts crept into my head. I was staring at his crotch, observing how he moved, looking him over. ‘Shake it off, Brian!’ I thought to myself.

I had about 155 yards to go. I stood over my ball saying to myself, ‘Think, think. What do you do here? God, concentrate!’ I looked over at Jack.

“What are you thinking?” he asked. “You look lost.” No shit.

“I got it.” Angry at myself, I grabbed my 8 iron, choked down an inch, checked my aim and swung down hard on the ball, compressing it just right. My ball hit the green about 8 feet left of the flag then spun right, ending up inches from the hole.

“Holy shit, Brian! Shot of the day, man!” Jack exclaimed. I was bursting – it was a great shot and I was somewhat lifted, forgetting the thoughts of the last few minutes. Birdies will have that effect!

Jack took a moment to assess his options, selected a club, and let it rip. He must have been pumped or took too much club because his ball landed at the back of the green, rolling off onto the fringe. “Shit, shit, fuckity shit!”

“Hey, you’re OK, man,” I said. “You can still putt that one in.”

As we parked beside the green, we each popped open another beer. Jack said, “I glad we didn’t have a bet going on this hole!”

On the green, I tapped in for birdie then tended the flag for his effort. He was at least 40 feet from the hole, downhill but breaking right to left, which I’ve always thought was an easier putt to read. Jack walked around, assessing the green for any secrets hidden in the bent grass. As I watched him, I began to really look him over, watching him move around. Checking out his legs, his back, his ass? OK, I’m doing it again. Stop!

Jack stands over his ball, makes a smooth stroke and sends the ball on its way. It actually broke twice, something I didn’t pick up looking from the hole, and it had a lot of pace on it, enough that I thought he may roll off the front. But his line was good. Really good! Fucking GREAT! I pulled the pin and watched his ball hit the back of the cup, pop up a few inches then settle into the bottom of the cup.

We roared simultaneously. “Yay!” It was a helluva putt, and for birdie, no less. We were tied once more.

“Man, did you see the break on that thing?” he said. “That might be the best putt of my life!” I replied, “That was ridiculous! I’m glad I was here to see it – you can say you had a witness!” We floated off the green.

We sat in the cart while Jack recorded the scores, finished off our beers and popped open another. “Let’s just sit here a few more minutes and enjoy this, OK?” Jack sighed. “I’m having such a good time. You?”

“Yeah, I am. This day seems so surreal, with the weather and the course. And the way I’m playing? God, I’ve never played this well, ever!”

We were interrupted by the sound of an approaching cart. The ranger came chugging his way down the cart path, stopping beside us. “Hi there!” said the old-timer. “You fellas are the only ones on the back nine. Can you believe it? And on a day like this?”

We agreed, and started to tell him so, but he cut us off. “Look, can’t chit-chat boys – I gotta run. Since there’s no one out here, they’re letting me off early so I can play a round.” He started to pull away. “Have fun, see ya!” And off he went.

We chuckled together. “Good for him!”

We sipped our beer and listened to the sound of the breeze through the pines. Jack started the cart and headed towards the next tee box, stopping in the shade halfway there. “So, where were we on the match?”

I hesitated. “Um, we were, ah, trying to decide what the bet should be. I guess it’s safe to say that money is off the table since we’re starting late. Besides, it could ruin a day like this, right?” I smiled slightly, not looking his way.

“Yep, I agree,” he said. “I do have an idea that’s kind of out there.” He paused for a moment. “I mean, I’m thinking you and I are getting along so well, right? And we’re having fun?” He’s looking right at me. “And this would be a real kick if you’re up for it.”

Here we go. I’m nervous, fluttering. And I want to know… “Let’s hear it.”

“OK – lose a hole, lose clothing.”

What? My mind is racing now. I’m doing the math, assessing what that would mean, what that could mean.

“Are you serious?” I ask, somewhat timidly.

“Yeah, c’mon Bri!” says Jack. “It would be a blast. We’re out here in the great outdoors on a glorious day, no one else around – we have the whole place to ourselves, not a care in the world. It’ll be like we’re teenagers again. I’ll bet neither of us has ever done anything this crazy before, right?”

“Not even close.” I asked, “So you’re saying if I lose the next hole, I have to take something off? And what, leave it off, or put it back on if I win a hole?”

Jack replied, “I hadn’t thought that far ahead, but yeah, sure. Lose, it’s off, win, it’s back on. Sounds fair, yeah?”

I started doing the math again. We’re about to tee off 12, so that’s 7 more holes, and if one of us goes on a winning streak, one of use could end up…

“Um, Jack, I’m thinking that it is possible one of us could end up naked. There’s 7 holes left and…”

Jack cut me off. “Well, six actually. I think 18 is out of the mix, seeing how the clubhouse is in view, and vice versa. And obviously, hats, shoes and socks are necessary. But otherwise, yeah, it’s possible. Very possible!” There’s that grin again.

“C’mon, just a couple of guys enjoying the outdoors, playing golf and having a little naughty fun as a bonus. Live a little! When do you think this could ever happen again in your lifetime?”

I grabbed my beer and took a huge swallow, then another. How weird is this situation? Something I would never have considered, and yet, here I am thinking about it. And I have to admit, I’m getting excited at the prospect of being naked, or seeing Jack naked. I’m turned on. 

“Fuck it – let’s do it!” I take another long gulp. Jack slaps me hard on the back. “Yeah! This is gonna be fun, man!” He drives us to the 12th tee.

And I lose the hole. Done in again by a sand trap. Jack’s par beats my bogie. Shit.

We walk back to the cart, and I’m trying to decide what to remove. I can sense Jack looking at me expectantly. If I take off my shirt, I’ll probably become sunburned quickly as I’m very fair skinned. If I take off my shorts, it’s less likely. And I reason with myself – ‘I can play in my underwear, right?’ Thank God I’m wearing extended briefs and not tighty whities. And it’s exciting in a weird way.

As I start to undo my belt, Jack is watching intently. “Not your shirt?” he asks. I point upwards and grimace. “Ah, yes – got ya.” I unzip and shuck the shorts, folding them small and stuffing them behind my seat. This feels good.

“There, ya happy now?” I laughed. Jack does a little air circle with his finger, indicating I should pirouette for him. “Fuck off!” We both laugh. “I will say this,” Jack said, “You have nice legs!” And as I sit in the cart, I can feel my cock starting to firm up. We headed to the next tee.

The 13th hole is a par three, 175 yards uphill. It’s very challenging for me, and I’m sure for Jack as well. He has the honors, so he’s up. He hits a straight ball right at the pin, but we cannot see how it finished due to the elevation. 

As I walked up to the tee, I could feel my semi-erection pressing against my briefs. As I bent over to tee up my ball, Jack pipes up jokingly, “Nice ass!” I don’t know why I did it, maybe in the silliness of the moment, but a wiggled it back and forth. Then I pulled the trigger on my 4 iron, hitting the side of the green and bouncing off left, out of sight. Crap!

I’m back sitting in the cart, in my underwear and aroused. I look down at myself and realized my hardening cock was almost visible. It felt naughty – a bit like skinny dipping. I’m nervous as we drive up to the green. Jack’s ball is about 10 feet in front of the pin. My ball is in the rough about 15 feet off the green, pin high, downhill lie. Oh man.

I grab my 58 degree wedge with the intention of flopping the ball behind the pin and letting it float down. But the rough grabbed the club, killing most of the forward motion. My ball trickled onto the fringe. I’m still away. I lined up my putt, and tapped it lightly. It picked up speed, missed the hole and came to rest on the front of the green, well onto the fringe. Shit. I’m still away.

I looked over at Jack, and caught him looking at my legs and whatever else was down there. As I stood over my ball, considering my 4th shot, I could feel his eyes on my ass. I stroked it smoothly, my ball coming to rest a foot right of the cup. I tapped it in for my 5. 

I pulled the pin and said, “Go ahead, dude. Put me out of my misery!” He paused just a couple of seconds over the ball then drained it for a birdie.

Oh boy. Now I’m thinking about the next hole – pasty white, overweight me playing in just my underwear, in front of Jack. And again, it feels fucking exciting.

We stowed our clubs. No sense delaying, I guess. I sit in the cart, reach down and pull my shirt over my head. I look at Jack and smile. “Give me another beer please? I’m gonna need it.” He walks around to the back of the cart. I hear the cooler unzip then YOW! Ice cold water dripping down my back. “Jesus, Jack, that’s cold as hell!” I hear him chuckling as he hands me the beer. Then I hear him rummaging in his bag for something.

“Come here a sec, Brian?” He’s holding a can of sun block spray – how thoughtful! “Turn around.” I turned and put my hands on our bags. Jack started at my shoulders, lightly covering me, working his way down my back to my briefs. I started to say that I might win the next hole, which means I could put my shirt back on.

He says “Shhh” as I feel him touch my lower back, spreading the spray around a bit, his fingers pushing down the back of my briefs just a bit. Now I’m getting hard, my briefs bulging enough that my arousal was obvious. He squats down and starts on my legs. “I’m not too worried about my legs.” Again, “Shhh.”

He sprays up my left leg and down my right, using his hands again to spread it around. “Spread your legs just a bit, Bri.” I do so with nervous anticipation. Jack slides his hand up and down the inside my left leg then my right, almost touching my balls. Oh my God, I can’t believe how incredible this feels.

“Turn around.” I froze for a second. I didn’t realize he intended to continue. “That’s ok, I can do the front.” Jack looked disappointed, but handed me the can. As I started spraying my chest, Jack was stealing glances at my briefs and my obvious erection. As I bent over to do my legs, Jack moved behind me, watching. I finished by doing my belly, and dipped my hand a bit into my briefs two or three times. “Thanks, Jack,” I said as I handed him back the tube, “let’s get on with it!”

I hopped in the cart, sitting in just my briefs with a hard on that was pushing up towards the waistband of my briefs. And I didn’t care. It was exhilarating to be almost naked outdoors with a conspirator, knowing that this could get even better rather quickly. After that caress filled application of sun block, I was surer of his intentions.

The 14th hole was a short par 4. Jack’s drive went awry immediately, off into the woods on the right. As I teed up my ball, Jack said “Nice view!” I turned to see him grinning at me. I have to say, it was a unique feeling standing over a ball, ready to drive, in the great outdoors while in my underwear and sporting a woody to end all woodies. 

Still, I drove my ball down the left center of the fairway. That motion caused my erection to rub against my briefs in an incredibly stimulating fashion. As I held my follow through, I looked down. The head of my cock had popped out of the right leg of my briefs. I left it there and headed to the cart, Jack watching the entire time.

He opted to drop another ball where his drive had crossed, and I didn’t blame him. No out of bounds here, but the woods were thick and his chances of finding the ball were zero. His shot landed short of the green by 10 yards, not too bad. I had 120 to go, a wedge shot. I was standing over my ball, trying to concentrate as my erection was peeking out of my briefs. This is exciting. I hit my wedge pretty well, landing on the green. As I walked back to the cart, Jack smiled, asking, “Looks like you had two clubs to choose from for that shot, huh?” I just smiled back.

As we rode up to the green, Jack was glancing at my ‘condition’ and said, “You doing ok over there? You look a bit uncomfortable.”

“Nah, I’m good,” I said, “with all this fresh air and sunshine. It’s awesome. How are you doing?”

“I’m good,” Jack responded, “just a little uncomfortable.” I picked up his meaning and snuck a glance at his crotch. His cock was snaking down the leg of his shorts, and it was huge! I quickly looked up. Was that really what I saw? Geez!

Before a could take another gander, Jack grabbed a couple of clubs and walked over to his ball – I grabbed my putter. I could now see his erection pressing against his shorts as he stood over his ball. Very impressive. I thought back for a moment to my 20s and my very few bi experiences, and didn’t recall being with anyone larger than me. My 6.5 inch cock was rather thick, but Jack’s obviously surpassed me in both width and length.

Jack flubbed his chip, coming up short. I was away, and took a minute to walk all around the green to assess the putt. As I walked in front of him, he flipped the handle of his club up and lightly whacked me right in the crack of my ass. ‘Hey, I’m trying to concentrate here!’ I joked. He was smiling as he said, ‘Sorry, couldn’t resist.’ Yeah, I’ll bet.

I had two putts to make par, and the best Jack could do now was bogie. I snaked the left to right putt to about two feet above the hole. Hmmm. I marked my ball, turning so that my ass was to Jack as I bent over. 

He elected to putt from the fringe. It was a weird silhouette – Jack bending over his putt, club drawing down to the ball, and a triangle between his hands and his hips where his shorts were bulging. And, as he had done twice already today, he jarred the putt for a bogie. Man, that is some fine putting.

So now the pressure was on me to make my par putt to win the hole. Two feet, slightly downhill. Take it easy, you can do this… nice smooth stroke, keep your head down. Yes! I jumped up, dislodging my briefs enough that they fell slightly, a couple of inches. I returned to the cart without fixing them.

“Nice putt, man. I guess you can put your shirt back on.” I watched as Jack put his clubs in the bag, turned towards me and started undoing his belt. 

“You can take your shirt off Jack, no?” I asked. He smiled at me and said “Well, it’s my choice, right?” as he dropped his shorts, revealing that he had gone commando. Oh my God, there it was. His erection was hanging down in front of him, at least 8 inches, maybe more. And thick. And dripping precum. He stepped out of the shorts, stowing them behind his seat. He grabbed a towel from his bag, put it on his seat then jumped in.

“You gonna put your shirt back on?” he asked. I didn’t answer – I was mesmerized by his incredible dick. “Brian?” 

I answered quickly, “Oh, sorry – umm, nah, it will stick to me because of the sunscreen.” Well, it might. But I didn’t want to put my shirt back on. What I really wanted was to take my briefs off. As we headed for the 15th hole, I stole a couple of glances at his erection. “Um, how does it feel, Jack, you know, out like that?” ‘Out like that?’ Geez, I’m an idiot.

“It feels fucking awesome!” he said as we pulled up. “You should try it.”

I left the cart, completely immersed in thoughts of running across the fairway naked without caring what anyone else saw or felt. I felt like I was 15 again. As I grabbed my driver, I looked over at Jack. He had taken off his shirt as well, standing next to the cart wearing nothing but his hat, socks and shoes. I had to admit, he looked good. His chest was covered with a medium sized patch of dark brown hair, and his pink nipples stood out. He was moderately muscled with some chubby spots in the usual places, like me. And that huge fucking cock. I was completely erect no, straining against my briefs.

“Um, Jack, what about the match?” I said.

“Fuck the match. I want to be naked out here, and I want you to be naked too.” He stared at me expectantly. “C’mon, take them off.”

I paused about 2 seconds then bagged my driver. I turned back to Jack, grabbing the waist of my briefs, about to pull them down.

Jack asked softly, “Is it ok if I do that?”

I dropped my hands as I stared at his cock then smiled. “Sure.”

He slowly walked over, stopping about a foot in front of me. I stretched my arms above my head then put my hands on top of my head. I expected him to grab my briefs and pull them down, but instead, he circled behind me, coming up close enough that I could feel his cock against my ass. I shivered violently. He leaned in, hands on my hips, whispering, “Relax, Bri. Just enjoy the moment.”

He knelt down close behind me. I was shaking again with excitement. Jack started caressing my ass through the briefs, palming me, squeezing and twisting. He ran a finger up the crack, slowly, achingly slow, until he reached the top of my briefs. Then he hooked that finger over the waistband and slowly drew my briefs down. As the V formed by my briefs exposed each inch of my ass, he would lean in to kiss and lick it. He reached between my legs with the other hand, grabbing the cloth below my erection, pulling the front down in sync with the back. He pulled my briefs down to my legs, then my ankles, exposing me completely to the outdoors for the first time since my youth.

The shaking wouldn’t stop. I turned towards the cart, putting my hands on the roof edge to steady myself. The sun beating down on my exposed ass cheeks felt electric.

Jack stood, coming up behind me again. I could feel his ‘driver’ resting in my crack. He reached around and cradled my cock gently in his hand. “Was I right? Isn’t this awesome?”

I closed my eyes, concentrating on the sensation of his cock against my ass. “Yes,” I replied with some vibrato in my voice, “just incredible.” I pushed back slightly, just enough to show him I was enjoying feeling his body against mine.

Jack stood back. “Bri, your ass is as white as your shirt. I need to put some sunscreen on ya, ok?” I nodded expectantly, staying where I was, leaning on the cart. My erection was bobbing in front of me, dripping now.

Jack grabbed a tube of sunscreen from his bag. “This is better than the spray, better SPF.”

Yes! He dropped behind me again, but instead of applying the cream, he started caressing and kneading my naked ass cheeks. Then I felt him lean in to kiss my cheeks, back and forth. Then he palmed my cheeks and pulled them apart enough to expose my wrinkle. I can’t believe my asshole has sunshine on it! He pulled my cheeks apart further, leaning in more. I could feel his face pressing against me then his tongue against my asshole. I shuddered at the contact. He licked and prodded at my opening, gently pressing, circling. My knees started to shake badly.

After one last deep probe with his tongue, Jack stood. He grabbed my shoulders, turning me to face him, looking me in the eyes with his blue piercing gaze. His hands were on my shoulders, gently pushing downward until I was on my knees. I wanted this, I wanted him.

His enormous cock was hanging down, dripping like a leaky faucet. I leaned in first to sniff around his organ, taking in his scent, so manly and spicy. I gently lifted it up to my mouth. I used my tongue to collect his precum, then swirled it around the head. I pressed forward, taking a couple of inches across my tongue, pressing him up against the roof of my mouth, sheathing him with my curled lips. He was so big, so powerful in my mouth. My jaw was opened wide, my tongue pressed against the floor of my mouth as his cock slid into my soft palette. Then out, then in again, just a bit further. I could feel him shaking now, signaling through his cock that I was doing well by him.

He placed his hands gently on my head as I pressed forward a bit more. His hands on my head almost made me cum. Less than half of his cock was in my mouth now. I started sliding him out and in, maintaining pressure with my tongue. I brought a hand up to caress his balls. I made a ring with my other hand’s thumb and forefinger, encircling his shaft, pumping him as I started increasing my speed.

Now I had more than half of him in my mouth. I knew I could never take all of him, but would try to take as much as I could. I pressed forward again, back and forth, sliding my tongue side to side under the head side as it passed over my bottom lip. I think I had 5 inches of his wonderful cock in my mouth now, pressing against my throat.

Jack tapped me on the head. “You are incredible! I’ve never had a blow job like this. I’m so fucking close.”

I slowly drew him across my tongue and from my mouth, keeping my fingers around him. “Jack, I haven’t done this in over 30 years. It’s this day, man. Everything is better, everything. It’s destiny.”

“I want you to come in my mouth, don’t hold back.”

I could feel his cock expand slightly, and had just taken it back in my mouth when he exploded. I continued taking him as deeply as possible, pressing my tongue upwards as he unloaded in my mouth. He came for at least 15 seconds as my fingers pumped him. His turn to lean on the cart! I kept his cock in my mouth for a couple of minutes until it started to soften, swirling his cum around, bathing him in it. Then I just held him softly in my mouth, no movement, no sound. We stayed like that for a couple of more minutes. I could feel his heartbeat on my tongue. I swallowed.

Jack stood back, looking at me, his eyes sparkling, mouth creased in a satisfied way. I stood up, my cock about to burst without being touched. 

He stepped forward, and gently pulled me into an affectionate embrace. Ear to ear, his hands gently holding my ass cheeks, he whispered, “My turn?” He snaked one hand between us, holding my cock, sliding a finger across my slit, getting it slick.

I warned him. “You’ve got about 5 seconds.”

Jack dropped to his knees, put both hands on my ass, and pulled me into his mouth. I erupted with incredible force. Just as my first cum shot hit his mouth, he reached between my legs and pressed that slippery finger deep into my asshole. I continued coming, unable to open my eyes, unable to hear anything except my body tensing and releasing with each rope of cum. Then Jack pulled me completely into his mouth. I continued coming, feeling his nose pressed against my belly, feeling his finger pumping my asshole. I was shaking again, weak in the knees. 

Jack kept at it until I couldn’t take it any longer. I pressed against his head. He understood, and stood up. There was cum on his chin and cheek. I took his head between my hands, leaned in and gently licked it off. I kissed him lightly on the lips, then said, “Thank you, Jack.” I pulled him into an embrace. “Thanks for making this the most incredible experience ever.” He was massaging my ass checks again.

“You’re welcome.” Jack held me for a minute, continuing his gentle massage of my ass before breaking our embrace.

“Hey, we almost forgot the sunscreen!” he said. I looked down, and his erection was full and pulsing again. He grabbed my arm, turning me around, pressing against my neck until I was bent over the armrest of the cart, forehead pressed against the seat. I was stunned, and frozen in place. Was this really happening? Was Jack going to fuck me, out here, like this? With that enormous cock?

He grabbed the tube and squeezed out some cream onto both cheeks of my ass. Then he pulled my cheek aside and put some directly on my asshole. He used his finger to press some cream into my ass. Then I felt the nozzle of the tube being pressed into my hole. He squeezed out some more. He stopped for a moment. I guessed he was applying cream to his cock. Then the tube landed on the floor of the cart.

“Brian, you have the most beautiful ass I’ve ever seen” he said. He started rubbing the cream around my cheeks. “Are you ok with this?”

I couldn’t speak. Blood was rushing to my head. I was spinning, hanging on a precipice between desire and fear.

I nodded yes.

Jack inserted his finger, moving it around to loosen me up a bit. It felt good. Then what felt like two fingers, then three. Pushing them in as far as he could. It was uncomfortable but tolerable. He continued until he was satisfied I was loose.

Then he moved against me, grabbing my hip with one hand while rubbing his huge cock head up and down against my hole. I felt his cock stop at my entrance, nudging against me, teasing me. He continued this for a few seconds, and then pressed.

It felt like his fist, it was so large. His cock was parting my ass cheeks, pressing outward against them. I could feel my sphincter resisting, his cock pressing the entire anal ring into my body. He pressed firmly against the resistance, no doubt bending his cock with the effort. He backed off for a second, and then started again. Pressing hard, relentlessly. Suddenly, the ring relaxed and the giant head of his cock popped in. 

You know the expression ‘seeing stars’ – it happens. I saw flashes of light at the same instant I felt the searing, almost unbearable pain of his enormous cock penetrating my ass. Oh my God, it hurt. I lurched, trying to move away, prevented from doing so by the armrest. Jack sensed my pain, and pulled out. What a relief, but at the same time, disappointment.

He started rubbing my asshole with his cockhead again, telling me to relax – that we’ll wait a minute.

He started again, pressing his cock head into me, and this time, it entered easier. It was still painful, but much less so. He continued pressing forward, and I could feel myself filling up with his manhood. As large as the head of his cock was, the shaft was slightly larger. And I could definitely feel it expanding my asshole. He started stroking slowly in and out. “How’s that feel?” he asked.

“Keep going,” I grunted, “I need you to keep going.” I really did.

Jack started moving in and out a little faster, and I sensed a little deeper with each stroke. After a minute, I could feel his pubic hair up against my ass checks. He was all the way in. I took it all.

“Feel good, Bri?” he asked again as he rubbed my lower back softly. I couldn’t describe all the different senses and emotions flooding me at that moment. My cock was rubbing against the side of the seat, hard and dripping again, and I knew I was going to come again from the thorough fucking I was receiving from Jack’s incredible cock. 

“Fuck me, Jack. Please. As deep as you can, just fuck me. Come in me, Jack. Please?”

He grabbed my hips and started pounding into me, deep and quick, again and again. It was breathtaking, literally. My ass felt the ridges of his cock rubbing against my anal ring. The cart was rocking with our movements.

The he pulled me off the cart, keeping me impaled on his magnificent cock. He took us down to our knees in the grass, grasping my body upright against his. “You’re going to love this” he grunted.

He pulled out then squatted behind me, changing the angle of his cock. He moved up tight and reentered my ass. And he was right, oh so right! His giant rod was rolling across my prostate, causing a new sensory overload. How could this have possibly gotten better? He reached around and started stroking my cock in time with his strokes.

Suddenly, he pushed me forward so that my face was in the grass, my ass up in the air under him. He shifted his position again, now straddling my ass, and started pounding me again. Such hard, deep strokes – stretching me, rolling against my prostrate, touching bottom – loving me.

My cock started throbbing. I was going to come again. I resisted the temptation to touch myself, to see if Jack’s cock in my ass could be all I needed to go over the edge. I yelled, “I’m coming, Jack! Fuck me, I’m coming!” as he pounded away. 

Then Jack grunted loudly, pulling my hips firmly, driving every last millimeter of his incredible cock to the bottom of my ass, coming deep inside of me. That did it for me – I sprayed my cum onto the grass under my chest. He pulled out, then back in again, two times, three times. Finally coming to rest bottomed out inside my asshole.

We stayed like that for a just minute. Then Jack slowly pulled his cock out of my ass. “I can’t believe I’m still almost hard. That was the best fuck of my life, Bri. I mean it.”

I slowly rose to my knees. I reached back, grabbed his cock and dragged him around in front of me. I pumped his firm rod a few times, lightly and lovingly, while he looked down at me. “Jack, I have never, ever, felt anything like that before. I can’t describe it.” Then I leaned forward, taking his softening cock into my mouth, sucking and cleaning him. There was nothing foul, just a little funky.

His huge cock was not fully erect. I grabbed his thighs and pulled him to me, hard. His cock lodged in my throat and I quickly pulled off, gagging. I tried again. This time I was able to hold him in my throat for a few seconds before pulling off. I tried again, this time holding him there without a problem. I started bobbing my head back and forth, feeling his hardening rod sliding down my throat and back out, again and again.

Jack decided to take control at this point, grabbing my head and stroking his cock in and out of my throat. But now I had a serious problem. His giant cock was hardening quickly. When he almost fully hard, I couldn’t take his size any longer. I pulled off, gagging. “Too big, Jack. Too fucking big! Sorry, man.”

Jack pulled me up and walked us around to my side of the cart. He pulled his towel over and sat down. Then he guided me to sit in his lap, facing forward. I leaned over onto the front of the cart while he aligned his cock with my anus then slowly sat me down onto his ramrod. Oh my God, it’s happening again. I’m flooded with unbelievable emotions. My cock starts hardening. My legs are shaking.

He is so deep I can feel him in my stomach. He pushes my ass cheeks, encouraging me to stroke up and down on his prick. Up and down, up and down. Jack reached around and grabbed my cock, stroking me. Wonderful, just wonder…

What was that? I heard what sounded like a golf cart heading out way. “Jack, someone’s coming!” We scrambled to get our clothes back on – what a circus! We finally just grabbed everything and jumped in the cart.

A twosome was coming up the fairway on the previous hole. Half naked, we high tailed it out of there, racing down the 15th fairway, stopping on the path behind the green. We started laughing. That was exciting! 

We took an extra minute to get ourselves sorted out and I realized my briefs were missing. Probably lying back there next to the tee box. Oh well. It was worth it.

We sat quietly for a few minutes before Jack spoke up. “You know, this was the best golfing day of my life. Meeting you was, well, awesome. I hope we can remain friends.”

I took out my phone and said “Call me” as I recited my number to him. It rang, and I added him to my contacts.

“Let’s get going.” As we rode to the parking lot, my ass was reminding me of the incredible fucking I’d received, almost twice, from Jack. “You know, Jack, we have some unfinished business. We should schedule a tee time before we leave. What do you think?” I said, grinning. I reached over and squeezed his cock though his shorts.

“Hmm,” He replied. “What are you doing the rest of the afternoon?”

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