Match Play Twosome

"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.