The Sad Boys Series: Leroy and Rex Date #2 Part Four Dating Disasters written by Jimmy

 

The Sad Boys Series:

Leroy and Rex Date #2 Part Four

Dating Disasters

 

By Jimmy

 

 

 

Rex is on his skateboard, he’s smiling as Leroy approaches having just left his ‘date’ with Jayden moments before. Leroy is still shirtless, a little bit of sweat gathers at the nape of his neck and his lower back but it feels so good in the sunlight that he does not care.

 

He twists the board at Leroy’s approach and kicks off, pumping his sneaker into the pavement. Rex spins around him and screeches to a full stop in front of him, kicking up bits of gravel that pelt off of Leroy’s legs.

 

“Finally, you came.”

 

“Yeah, it’s your turn. So you’re a skateboarder now?”

 

“Maybe.”

 

Rex kicks it up under his arm. “Want me to show you some tricks?” A sly foxlike smile glides across his face, his dazzling amber eyes alight with mischief as Max’s eyes meet Leroy’s. 

 

“Go on, show me what you got Rex.”

 

He does not need to be told twice. Rex’s smile hits his face as he throws the board to the ground.  Jumping on Rex spews pebbles behind him as he speeds towards the nearest ramp and slowly lowers himself as he rides up the inclined ramp. In a fantastic jump off, Rex manages to spin the board before at the last moment as he lands, coming back towards Leroy smiling all the way. The forever June sunlight casts him in the shadows of dusk as he ducks and swings around facing him slightly breathy, Rex’s smile this time gleams from his crooked grin. 

 

“Not too shabby, Rex. That’s—-” but another voice stops him as he shrieks past and jumps almost over their heads. 

 

“You think that’s cool, you should see me do this!” 

 

One of the classic Ballbusting Boys stars spins around, bare chested, jeans riding low showing off his bony hips, and pronounced V-shaped abdomen with more than a hint of underwear flashing. Leo jumps fully in the air, spinning and knocking board across the metal railing sparks shooting off and flaring off at the end and landing with a perfect smack of his board.

 

Rex’s smile does not drop, but it twitches. 

 

“Not bad,” he admits. 

 

Leroy looks impressed and says “That was sweet, man.”

 

“Yeah, I know. Name’s Leo, I’ve been showing him the ropes.”  

 

“For a fee,” Rex mumbles almost inaudibly. And idea strikes Rex and he scoops up his board moving between Leroy and Leo, and winking over his shoulder at Leroy. Rex’s mischievous grin is back. “You know, I got one more move to show you.”

 

While walking backwards the wheel of his board smacks Leo right in his bulge with a hard smack and Rex spins around full circle in surprise just as registration dawns on Leo’s face and the other side of his board hits him in the same exact spot.

 

“OOOoooomph!” Leo exhales, reaching down and grabbing his jean clad boys.

 

“Oh…my bad, Leo. Didn’t see you there…either time!”

 

Skipping off Rex leaves Leo just barely standing, holding his crotch a slight tremor trembles next to his left eye as his bottom lip juts out.

 

Leroy winces watching this play out, amusement makes him chuckle and he asks “You good, man?”

 

“Not even close,” Leo admits trying hard not to sink to his knees, as he rubs his right nut. A slight dent and bruise is already starting to develop from where the wheel struck it.

 “Fuuuuuck” he groans hair falling around his face.

 

Leroy looks up as Rex shouts “Watch me, Leroy!”

 

From the top of the ramps Rex jumps off, and goes low on the board swooshing down the ramp and jumps up at the end, airborne and manages to spin both to his delight and surprise as he goes all the way back up and comes off shooting towards the two. Rex pumps one fist in the air, and smacks Leo on the back “Couldn’t have learned that move without you, see you next week bro!”

 

Leo mumbles “No…problem.”

 

Leroy and Rex watch him stumble off to bench still holding his nuts in agony.

 

“Maybe it hurts more as you get older,” Rex announces, shaking his shoulders. “Something worth exploring as he teaches me.”

 

Laughing Leroy grabs Rex’s shoulder tight, “That was sick man.”

 

Rex’s smile widens and he licks his lips. “Come on, I got another surprise for you.” Rex touches Leroy’s hand on his shoulder and gently takes it off, but he does not let go as he pulls him along.

 

Leroy has to tell Rex to “Slow down kid!” he laughs, as Rex almost runs out of the skate park, while shadows descend all around them as night creeps in closer eating up the day. Leroy has to almost run to keep up, Rex shows no stopping as he drags him along.

 

A few breathless moments later Leroy finds himself back at the ocean along Bartlet’s shore, but not at the dock. The two are at the beach, and the sun has almost made its final descent into the ocean beyond.

 

“Duck!” Rex commands yanking on Leroy’s arm until their knees hit the sand and it’s as if the sun is already gone. Leroy knows that it’s still there but Rex brought them to a hole in the sand that he must have dug earlier. The bottom is wet and his skin smarts from the bottom and the sounds of the ocean are gone from above and it almost appears that night has taken them hostage as Rex turns to look at Leroy. Rex’s warm amber eyes are on his searching, and the look that he gives him makes Leroy’s breath hitch.

 

“Don’t move… and close your eyes.”

 

Leroy almost says not but Rex comes in close, saying “Please bro, it will be worth it.”

 

He hesitates for a moment, but Leroy does as he’s asked wanting to see where this may lead.

 

The instant that he does Leroy’s cast in further darkness. A slight shuffle is heard above him and he hears Rex climbing out of the pit and kicking around sand. He’s back not before too much time is past and shuffles around the hole kicking around wet sand. Leroy’s skin begins to prickle, goosebumps blouson on his arms and chest and his teeth clack as a shiver runs down his back. He’s cold, and wanting out of the pit.

 

“Ready?” Leroy asks.

 

“Almost.”

 

Rex says it quietly in Leroy’s left ear, and he almost jumps.

 

“Just one minute more.”

 

About thirty seconds later Rex has stopped moving in behind him, and he puts his arms around Leroy’s waist. He’s shirtless too now and his small nipples are hard against his back, and Leroy shudders at the unexpected touch. Rex’s voice is soft and in his same right ear asking him to “Go on, you can open them now.”

 

Leroy does.

 

He finds himself in almost complete darkness. Rex has somehow covered the sand pit, and he glances up seeing a blanket or towel overhead and the smell of the wet sand is almost overpowering but it’s joined with the scent of Rex’s sweat, his own, and the chlorine from the pool. Leroy takes in a deep breath and relaxes against Rex. Leroy is taller, his chest wider and with bigger shoulders than the boy behind him. But Rex is steady, and his hands start to roam up, and along his sides as Rex watches him look around.

 

“What are we doing down here?” Leroy asks.

 

“I wanted to be alone with you, and that’s difficult because we both have noisy parents that I am sure will wonder about all the noise.”

 

“What noise?”

 

Rex slowly walks around Leroy until the two are toe-to-toe and he grabs him hard in the middle. Rex is only wearing his sky blue speedos and Leroy can barely make out the features of his face as he says “Rematch baby,” and shoves him hard so that Leroy lands on his back soaking the back of his shorts.

 

“Arrg!” Leroy yells, but the sound is muffled by the sand around him, and the blanket.

 

“No one can hear you scream, so do it as much as you want!” Rex jumps on top of him landing around, and steals all the air from him as he lands on his stomach. Leroy gasps and tries to sit up but Rex’s hands are around his throat.

 

“You aren’t going anywhere, bub.”

 

Anger flares in Leroy and he shoves at Rex, while Rex’s small fingers hold and squeeze his throat tightly, slowly increasing in pressure. Rex stays stubbornly put, despite the shove. The advantage of straddling Leroy is too much and the shove against Rex’s bare chest seems ineffective. Switching tactics, Leroy quickly feels the need for air forcing him to get creative as his chest burns with desire. Panicking Leroy rears his hips up and spots the small mound in between Rex’s widespread legs and fires his fist like a launched rocket straight into the sweet spot.

 

Rex’s amber eyes widen in alarm as Leroy’s knuckles strike his whole package into his pelvis, squashing his dick and balls in one horrid fluid move.

 

“My balls…oh fuck…that hurts!” Rex’s eyes roll, as a second wave of agony rushes over him, and Leroy’s fist keeps on pressing deeper flattening his little peanut M&M’s even flatter. Rex falls back onto the wet sand himself landing with a splash. The tide is slowly coming in and the water in the pit starts to rise. Rex grabs his sore balls, and squished penis dipping his groin into the cool ocean water feeling some instant relief as the frigid temperature acts like an icy pack as it numbs the contents of his Speedo’s.

 

Leroy grabs at his throat and croaks “What the actual fuck, Rex?” This was not what he expected this night to be like. He sits up, a cough barreling out of his chest as he keeps a steady watch on Rex slumped at the bottom of the water. Leroy’s eyes have adjusted to the darkness and he can make out the grimace on Rex’s face and tension in his brow as the aftereffects of the low blow flood his systems.

 

“Didn’t…haven’t you…always wondered who would win?” Rex asks, his eyes blinking and staring upwards not meeting Leroy’s.

 

“Ummm no?”

 

“Well…I have. That day at the pool…I was so close, and I wanted a rematch. And I got one!”

 

Leroy is standing now, grabbing the rim of the pit about to pull himself out, as Rex’s legs wrap around his ankle and pull. He yips as he tumbles back to the sand pit on top of Rex the two boys lose their collected breathes as they connect chest to chest. Leroy’s head spins as it lays on Rex’s shoulder, his lips against Rex’s skin almost kissing the warmth of him and an urge to do something dirty with him here in this pit overwhelms his senses as his hormones hit him hard. Leroy starts to feel himself hardening against Rex’s thigh.

 

“Thanks man.”

 

“Huh?”

 

“Now I know exactly where your balls are, your dick led the way.”

 

Dread fills Leroy and he’s too late in closing his legs as Rex shoots his thigh upwards plowing into his soft and plump lump at the bottom of his Speedo. “OOooooouuuugh!” Leroy grunts.

 

Rex keeps his leg right in between Leroy’s legs, and thumps the nestled nuggets with the tail end of his kneecap feeling the nuts glide around in Leroy’s scrotum trying to escape his ravaging knee. Wrapping his arms around Leroy’s lower back, he uses the advantage to bring his knee in and out between Leroy’s thigh snapping at the hanging swinging fruit with full advantage. Three quick strikes in a row sap Leroy of his strength, and his boner fades back from its full glory and wilts as Rex rearranges the contents of his scrotum so thoroughly.

 

“Oh god…fu….fuuuuuck….REX….st…..stoooop!” Leroy pleads, snapping his legs closed and preventing Rex’s leg to swing into his bulge again. Leroy’s balls pound fiercly in their fleshy sack, and he feels slightly ill as Leroy falls off of Rex next to him with a thud reaching down to protect his privates but Rex straddles him grabbing his hands and pinning them both above his head in one quick flourish. The school boy pin leaves Leroy in trouble as Rex’s amber eyes are fiercely enthralled by the meat between his legs as his eyes are cast behind him at the well-filled Speedos.

 

“What if I…?” Rex wonders out loud as he scooches back his hips, his bony but sliding along the contents of Leroy’s groin feeling the shift and sway of the cock and balls as the crack of his ass shimmy’s over Leroy and past his hips.

 

Leroy gasps at the intimacy of the touch, and even that slight trace along his most intimate parts causes him to moan in pain as his balls squish even further into his body. Rex delights at the sensations along his bottom and spreads his thighs a bit further as he moves his hips upwards and along the sizzling piss tube starting at Leroy’s tip and riding it back to the root. Unfortunately for Leroy, he takes the nuggets with him in his upward trajectory and the roll and tumble as Rex’s hard ass squish them. At one point they both wiggle and pop out from underneath Rex’s cheeks. At each pop, Leroy gasps and grunts his body tensing in agony as it waits for Rex to go back down again. Rex aims to be predictable, especially as he feels Leroy hardening yet again underneath him.

 

“You feel so good” Rex whispers as he rocks his bottom up and down Leroy’s shaft, feeling the pulse of the slender long stick that he buries along the crack of his ass. It fits so well there, and Rex craves for more contact as he grabs Leroy’s hardened nipples and pinching them. Rex is losing himself in the moment and bounces now on Leroy’s lovestick and flattening his orbs as he does so throwing his head back in a moan of his own.

 

Leroy discovers his hands free and Rex so into the moment that he does not notice as Leroy shoves him as hard as he can into the wall of the pit, which shakes sending clumps of wet sand to drop down, landing with a splash all around Leroy. Rex smacks the wall and goes to tumble back right on top of Leroy, however Leroy sends a foot right into the boy’s chest sending him careening back into the wall striking the same place. The double smack of Rex’s body into the wall of the pit causes a ripple effect as Rex loses his balance and tumbles to the pit floor but his arms swing trying to catch himself but only managing to cause the instructional integrity of the pit to falter as two of the sides lose two giant hunks and they fall directly on top of Rex.

 

“Rex!” Leroy shouts.

 

Scrambling to his feel Leroy’s heart wildly pound in his chest as he splashes towards Rex to make sure that he is alight.

 

“Rex!” Leroy stares into Rex’s eyes, he’s half buried in land. Rex’s chest is lost underneath a pile, but his head is clear and the second wall of sand seemed to have fallen on top of his thighs leaving a divet in between both mounds leaving his groin completely free.

 

“I…can’t move” Rex laughs. Only Rex’s hands seem visible and his lower legs stretch out but both are ineffective at stopping Leroy as he crotches down next to him. “You were saying something about beating me again?” Leroy reminds him one cool hand falling on his stomach and rubbing the tight group of muscles there.

 

Rex shifts and tries to push the sand off, his hands balled into fists but his efforts seem in vain, and they reopen like faltering limp dongs.

 

“I…wanted—” Rex starts to say but Leroy drops his other hand just below his scrotum and tickles the bottom of his sack and Rex’s words are lost to him as desire, the need for more flood his system and he grunts. A small gasp seeps from between his lips and the rushing water continues to come into the pit, and Leroy recognizes that if he is going to finish Rex…he needs to do so quickly.

 

“What did you want baby?” Leroy asks, his hand resting on Rex’s stomach lowers, slopping down his navel and spinning his thumb around his belly button pressing deep into it.

 

Rex’s breath hitches “I wanted to prove…” he tries to finish his sentence but his erection is already training upwards, the flagpole obvious as it tents his wet Speedo’s like a beacon. Even in the pit Leroy sees the protuberance.

 

“Prove what,” Leroy coaxes his fingers slipping into the Speedo’s creeping and tip-toeing down Rex’s pubis until it reaches his root and he slowly encircles it giving it a squeeze. “Tell me, Rexy.”

 

“Don’t call me…! Uggggggh!”

 

Leroy squeezes Rex’s balls, the sack is tight like a walnut at the base of his small flagpole and the little peanuts are instantly engulfed in his fist as his fingertips fight to plunge into the nutmeat. There is just not enough of it to satisfy each finger to squeeze and puncture. But for Rex it’s overwhelming and he grunts as his eyes roll back.

 

“Not my….balls!”

 

Leroy let’s up, but only for a moment he wants Rex to feel his fingers as the encircled fingers around his stiff shaft ride all the way to the tip, and back down. Rex’s groan stops and he looks back at Leroy and mumbles “You’re not gonna…” he gulps and finishes “make me cum…are you?”

 

Leroy does not answer as he masturbates Rex, the ease of his fingers gliding up and down the little shaft make it plain to him that he gets to fully control the hardened tool. It turns out that Leroy did not really need to answer Rex, it’s pretty obvious as he moves his fingers up and down the hard shaft, causing the head to flare as he Leroy’s thumb swipes around the tip using Rex’s own pre-cum to slick up fingers.

 

“Starting to feel good, right?” Leroy asks.

 

Rex’s eyes are half-closed, and his voice is surprisingly tranquil as he tells Leroy “Y-yeah…it feels real good now…but I wanted…to prove to you that I am man enough to dominate you. I wanted it…but now…like this.”

 

The confession, the truth spills from Rex and Leroy finds his lips tugging up. “Man, you didn’t need to prove anything to me.” He leans over, still masturbating him and his lips graze Rex’s cheek. “I want you Rex, and I want to see you squirt. Now put on a show for me before your head is covered by the sea.”

 

Rex’s eyes are on Leroy and he nods. “Okay…but no more low blows.”

 

Leroy’s smile widens and he thunks his forehead. “I almost forgot about these!” He reaches down plunking both nuggets up and into his fist and squeezes it tight again, clutching the balls and tugging a bit. Leroy is not trying to crush them like before, it’s more sensual…but he keeps up a steady squeeze.

 

“Sh…shiiiit!”

 

Leroy curls up next to Rex, finding a comfortable spot as any in the icy ocean water and begins to lovingly masturbate the boy. There is barely enough dick to wrap his hand around, but Leroy does not mention that.

 

“That feels really, really good…” sighs Rex. “But my balls Leroy…come on man don’t squeeze…any harder!”

 

“You sure?” Leroy purrs, and nuzzles Rex’s face next to his ear. “Just lay back and it will get better. Oh wait…you can’t move. Oh well stay still then. You can do that.”

 

“Fuuuck you,” Rex whispers back.

 

Leroy decides that Rex is taking way too long, and decides to lower his head, without giving Rex any warning and engulf Rex’s penis into his mouth and sucking him down fully to the base in one swallow.

 

Rex’s eyes snap open from his haze, and he appears too surprised to react as he stiffens and gasps “Oh god…that’s so….uuuuugggggggghhhh!”

 

Rex’s body seems to hold a new rigor, the feeling coursing through him are even more intense then Leroy’s hand.

 

The advantage of sucking a small dick is obvious: its size gives Leroy complete control over the means of stimulation that his tongue and lips have, and in addition would never tire his jaw unlike the way Aldo’s thickly veined monster did when he gave Leroy blow jobs. The thought of Aldo in this moment makes Leroy grip on Rex’s little pips tighten and he adds a mean twist that leaves Rex panting and fighting back a scream.

 

Rex clearly is not going to last much longer. Already his breathing is growing stronger, creating an audible counterpoint to his own sloppy cocksucking despite the splashing of the water that continues to flood the pit and dip into Max’s ears, as they fill with water. Leroy moans softly around Rex’s and he uses his free hand to roam over Rex’s tightly smooth swimmer’s body of that which he can still touch, which he finds tense and restless. Feeling him stir, and the shift of sand that slides across his neck Leroy looks up at his face realizing what is about to happen.

 

“You…I’m….” the hoarse whisper of his voice fills the sea filled pit and Leroy gives a moan of encouragement, and immediately starts sucking faster, constricting his lips and applying more suction. Rex’s hard little penis throbs with sensations as Leroy can literally suck the finger-sized cock in his mouth with the same action that he would use to suck a cookie blended milkshake through a straw.

 

Rex’s eyes roll shut, and his quick breathes move in and out as he pants, his body held hostage to the feeling and the wet sand piled on top of him.

 

Leroy sucks still faster, and faster as he uses both hands now to somehow separate Rex’s little peanuts in his little sack and roll the orbs in his fingers as he presses just his thumbs deep into the centers, but in reality it’s the whole ball.

 

“Nooooooo!” Rex shouts.

 

The sensations in Rex’s groin grow to a searing warmth, the pleasure-centers in his brain snapping open as a chain-reaction explodes almost too intense to bare. Rex cries out, his convulsing penis grinding into Leroy’s mouth wanting more and to go deeper, as his fingers open and close uselessly trying to grip something tangible. Leroy answers that need by crushing Rex’s nuts in his grasp as Rex’s quivering thighs lock, the muscles taut and the stiff little penis fires full rounds straight down his throat. Seven, eight, nine hard shots of milky thick semen pulse through his shaft, as Leroy sucks ever harder and steals the salty juices from deep within his nuts as Leroy rolls the churning nuggets in his hands.

 

One last gasp comes from Rex’s as his hips rise up and lock and he rears his head back as a gush of water floods the hole cover his face and mouth as he sputters out one last squirt of his juice down Leroy’s throat.

 

“Rex!” Leroy shouts and grabs both hands and tugs as hard as he can. The sand shifts, and more of Rex’s torso is thrown into view, but one last tug is needed to pull him up and out of the water. Rex lands against Leroy’s chest coughing and spluttering as the ocean above splashes and water cascades inward, the blanket soaked and falls ontop of the two boys. The water half-fills the whole and Leroy pulls and yanks Rex free as the two fall onto the beach.

 

It’s fully dark now, and the starry sky above seems to shine down on the two gasping teenagers as they scramble away from the waves. Leroy manages to save most of their clothes, as he dumps their things on the rock far off from the sea as he can get and leans against the sea wall.

 

Rex is on all fours, still spitting sea water onto the sand.

 

“You, alright?” Leroy huffs.

 

Max turns his head and glances up at Leroy, his body shaking.

 

Leroy sinks onto his knees next to him. “I should have—”

 

Max hushes him with a kiss, it tastes of the sea but Leroy doesn’t care as his mouth opens and he shares with Max the salty, tasty remnants of his orgasm.

 

Max breaks away first, he still has not gotten his breath back. “I want…to fucking do that again.”

 

“Really?”

 

“Yeah, well…maybe not that…but I want to with you. Leroy... will you be my boyfriend?”

 

Rex brushes his wet hair out of his face, and his lips are already on his neck kissing him with passion as his teeth nip and bite the exposed skin. It tastes of sweat, and the ocean and smoothness of Leroy’s scent. It makes Rex even weaker in the knees.

 

“Answer me.”

 

Leroy moans, he’s going to get an erection if Rex does not stop and he pushes him back staring at him.

 

“Rex…I got out of a relationship…it was messy. And the time before that…I’ve been burned. A lot. I need to go slow. I can’t say yes right now, but I…want to with you. Can you go slow with me, Rexy.”

 

Rex’s amber eyes flood “Only if you never call me that name again.” Rex’s demand is met with an intake of breath from Leroy as Rex grabs his balls and squeezes. Hard.

 

“Fucking…alright we can work on pet names later.”

 

Rex grins. He releases his nut hold and stands up, he’s still unsteady but dropping his speedos with a wet splat on the sand.

 

“Come with me…into the sea.”

 

“Haven’t you had enough water?” counters Leroy.

 

“I haven’t had enough of you. Now let’s go.”

 

Rex runs, naked in the wind and dives into the sea. He’s like merboy, and comes up with a grin his white skin almost glowing in the moon light.

 

Leroy rolls his eyes and he drops his shorts and speedos in one quick thrust. He’s bare, and the night June air is cool against his skin. He rubs the soft hair above his cock, and finds Rex’s eyes and the boy winks back at him daring him to come in.

 

Leroy does not disappoint him.

 

The two are englaged almost instantly, when Leroy splashes in limbs twisting everywhere and it’s the best kiss that he’s had in a long time as Rex presses himself into him.

 

“I’ll wait as long as I have to, for you.”

 

It’s all happening so fast, part of Leroy longs to run away. But a bigger part of him wants to stay.

 

“You better,” Leroy tells him and takes him into his arms and kisses him before a wave splashes against them breaking them apart. But Rex manages to hold on with one hand, despite the current.

 

He did not let go.

 

 

 

To be concluded in The Sad Boys Series: Max and Shane Part Five Dating Diasters