Big Boy Undies: Pool Boy

 

 

“Ramiro, bring some watermelon over here please.” A voice called out to the young man. A jovial guy sat at the edge of the pool kicking his feet, Dave Beckinsale. The man wasn’t dressed for the water, rather a casual hang. His jeans were rolled up so his legs could soak. He had that strong dad build, broad shoulders, clean cut, square jaw. A few specs of gray hair but was undoubtedly entering middle age gracefully. His hands rested between his legs, right above a huge bulge Ramiro couldn’t take his eyes off of.
 
He walked through the pool, to present the small bowl. He wasn’t in swimming trunks, just a pair of tight black and gold imperial undies, mandated as his uniform. As was Ms. Gretchen’s will. She enjoyed hosting neighbors, to flaunt off her wealth. The house, the land, the pool, all symbols of her status. The pool boys were the eye candy. Or more, if she so desired. The choice of underwear was to show off their best qualities, their asses and cocks, once the water soaked their lower halves.
 
Dave was here because Ms. Gretchen was Daddy hunting. She had all this money but wanted a man to stuff her with a baby. The lady of the house however could be quite…greedy. Currently she retreated to her room under the guise of changing clothes but was undoubtedly getting her pussy wet on Agustín’s cock, Ramiro’s older brother. There was nothing she loved more than riding her favorite pool boy. For the past 4 nights, Ramiro heard Agustín sneaking back into their pool guest house. The shower would turn on then he’d walk in as if cracking their employer’s back wasn't a big deal. For all their escapades, Ms. Gretchen never seemed worried about getting knocked up with Agustín’s baby before finding the man of her dreams. 

Ramiro was here to entertain and assess Mr. Beckinsale. See, if he was worth Ms. Gretchen’s time. Sure, she wanted him but didn’t mean he met her standards. Anyone could see Mr. Beckinsale was handsome but was he kind, caring, rich? That last one was really important, but not as important as how full his bull balls were and how huge of a load did he shoot? Ramiro didn’t know the answer to any but knew it wasn’t going to work out for his employer. From the moment he stepped onto the property, Mr. Beckinsale only had eyes for the Moreno brothers. The man was gay. Ramiro knew it for a fact, but Ms. Gretchen would want evidence.
 
The Hispanic pool boy stepped in between, Mr. Beckinsale’s open legs, resting the bowl on the man’s thighs. The guest was shocked as Ramiro fed him a piece of watermelon. The larger man had to lean over to take a bite. Then Ramiro slowly took his own bite from the same piece, eyes on Mr. Beckinsale. The man’s cock hardened inside his pants making an even more visible print. Took a lot of strength for Ramiro not to pull it out. Although they were having a moment, the man still believed he was here for innocuous reasons. He could pop boners all day long, but until a line was crossed, he was still on Ms. Gretchen’s list. And if they did prefer men, Ms. Gretchen was a fan of her pool boy drawing out the sexual tension. Also left her more time to have sex. 
 
“Would you like anything else, Mr. Beckinsale?” Ramiro asked.
 
“Dave, call me Dave.” He requested. They finished off the rest of the watermelon eating the other pieces the same way. Ramiro got out of the pool, feeling Dave’s eyes on his ass. He turned back, as the man nervously looked anywhere else. Then he did a stretch purposefully thrusting his crotch forward. Before turning back inside the house. The look on Dave’s face…Ramiro wanted to kiss it so badly.  The older man was just a bundle of good vibes and nerves, even if he was straight, Dave would still be out of his depth on Ms. Gretchen’s property. Ramiro had his struggles being around the man, and not all of it had to do with what was under his clothes.
 
—
 
Last week, it hadn't been a struggle for Ramiro to be around Dave. Ramiro hadn’t even existed last week. 7 days ago, Ramiro Moreno had been Ian Beckinsale. Dave’s son. The same golden blonde hair and blue eyes. Him and his dad were direct neighbors to Ms. Gretchen. They didn’t concern themselves with her. Not in a cruel way, Dave would always wave and make small talk, but it was often clear she was a woman who moved with purpose. She had places to go and people to talk to. Not to mention the litany of men she often had leaving her place.
 
Ian Beckinsale, however, was more curious than his dad. He’d often take a peek over the fence and see a pool waiting. Unused. Unloved. Sometimes Ms. Gretchen would be out there tanning with a guy, walking around the pool. Neither ever seemed that interested in the actual water. So, at night when the coast was clear, Ian would sneak into the yard and play in the pool. He was cautious those first few times and would never splash too loud. But it became clear on the nights, the yard was vacant, no one was coming to check on him.
 
Dave actually struck up more of a friendship with the pool boy, Agustín. The young man was her best kept secret. Dave happened to be trimming his tree when he got a look over the backyard fence. Agustín Moreno was out back in his underwear, skin tanned by the sun as he cleaned the pool. A conversation was struck up, then another the next day, and the next. Until Agustín had both Beckinsales in Ms. Gretchen’s backyard during the day.
 
“Are you sure this is okay? I don’t want to get you in trouble.” Dave said standing behind Ian, one hand on his boy’s shoulder.
 
 Agustín sucked his teeth, “She doesn’t mind who I let use the pool as long as it’s clean.” 
 
With that Dave let Ian take off into the pool as the two talked. When they joined Ian, they had a three-way race, a splash off, then the day ended with Agustín playing his guitar. The sun was setting, a soft breeze was blowing, and Agustín and Dave were sitting super close. Ian had been too preoccupied with himself at the time, but looking back, there was no mistaking the look in his dad’s eyes: He wanted to fuck Agustín BADLY. Ian had known his father was gay but hadn’t once thought about his father’s desires.
 
Ian, however, didn't stop his nightly trips, if anything he felt more compelled to sneak out of bed and hop in the pool. At the time he never knew where Agustín disappeared to on those nights, but the pool house being dark was always a sign the coast was clear.
 
Soon the three of them were in Ms. Gretchen’s backyard every day. 
 
“Why do you wear those?” Dave reached over and snapped Agustín’s wet underwear band. The three of them were drying off after an afternoon of swimming. “Should I get you some actual trunks?”
 
“Oh, Ms. Gretchen’s just a fan of it.” The young man laughed, sitting up, “lets her see,” His eyes flew to Ian, he cleared his throat. “You know.”
 
“Ah,” Dave nodded. 
 
Ian was dozing off, but he saw the way his dad eyed the underwear. Were they really that cool? His eyes were closed before he knew it. Ian didn’t know how long he slept, but he woke up a little after he felt his dad’s presence leave his side.

It was dark out.

He listened as the older males' voices got further and further away. Slowly he began to rise, rubbing his eyes. Ian wandered to the pool house where a light was on. Sliding into the open door he walked through the darkened humble abode. He saw Agustín standing around in the bathroom, playing in the mirror. 
 
“It’s a pretty nice place you got here.” Ian's dad came out of the bedroom.
 
Agustín spun quickly on his feet and took another position. For a moment Ian saw how his dad viewed Agustín.
 

 

 “Glad you like it. You could always stay the night.”  Agustín added.
 
“Ehhh, I think that might be pushing it with Ms. Gretchen. And I should get Ian to bed, I don't want him out there too long.” 
 
“Well, if you change your mind.”
 
Ian couldn’t see what happened next, but his dad stepped forward and closed the distance between himself and Agustín. Taking the time, Ian walked back outside and laid down stargazing just as his father stepped out of the pool house. Dave squatted down and rubbed his son’s head, “Time to go home champ, looks like you’re getting sleepy.” 
 
Agustín walked them out, then waved goodbye. Ian took one last look. An odd sight for him: to see the pool boy at night. Agustín’s underwear was on Ian’s mind the whole night. Ian had never seen underwear that looked like that nor that people just got into the water with. His dad, however, looked at them the whole afternoon. Dave probably thought Ian didn’t notice, but he did. If his dad liked Agustín so much in the underwear, would he like Ian more in underwear like that? Could Ian be as cool as Agustín?
 
He’d get his answer the following night. When Ian went for his usual late-night swim, he saw them both out there. Agustín and Ms. Gretchen. They ran around the pool until he wrapped her in a behind hug not letting the older lady escape. They shared a laugh.
 
“So, tell me about our new neighbor." She inquired.
 
“Oh, he’s a good one. Got a kid already, so I know he can get the job done, but I gotta tell ya he wants this cock and ass more than you. I’ve been buttering him up for weeks to present to you and he hasn’t taken the bait. Every time he manages to turn it back to me. He’s kinda smooth that way. Definitely think he’s gay, Ms. Gretch.”
 
The lady snuggled in Agustín’s arms, “Well, until you hear him say it, one never knows. He could just be interested in you, or bi, or pan.” She turned her head and kissed Agustín’s face. “That’s what makes you such good bait to weed them out, my bisexual disaster.”
 
“Anything for you, Gretch.”
 
“Anything huh?” She said smugly. “If I didn’t know better, I’d say you’re keeping him for yourself.” A hand gently grabbed Agustín’s chin and face. “You want him to have you in the pool house where everyone can hear you, don’t you? She brought their faces together and kissed him. “I’ll allow it, but first…” She moved out of Agustín’s arm, then removed her bra walking backwards towards the house, eyes on Agustín. Then after she disappeared inside, hung an arm out and dropped her bikini bottoms. Agustín pulled down his underwear, a muscular ass released into the night, chasing after her as something big swung between his legs. 
 
Ian waited for the voices to fade until it was clear they weren’t coming back. He was confused about what they wanted his dad for but strolled inside the backyard regardless. There he saw Agustín’s underwear lying there forgotten. It wasn't curiosity that drove Ian’s next actions, it was jealousy. A guy moves in next door and suddenly has his dad’s attention? Well, Ian wanted it back and those underwear were going to help him. He took off his own trunks before sliding into Agustín’s. The black fabric was way too big and loose for his body, but Ian was satisfied. 
 
Then all at once, a tremor shook from within him and sought a way out. The first attempt was his ass which popped, bigger and bigger. No escape there. It went to the opposite side as Ian’s cock snaked longer, and his ball hung heavier making his package swell. Frustrated, the tremor dispersed itself across his body, journeying through all the limbs. When it danced on his spine and legs, Ian grew exponentially. There was now more flesh and larger muscles to work through. His shoulder developed into a man’s width, alongside a prominent collarbone that preceded his pecs protrusion. 
 
Ian’s golden blonde hair turned a healthy sheen of rich dark brown. The same color as Agustín’s as the new coloring encroached and imposed itself on his body. His baby blues were done away with as the trademark Agustín-brown stamped themselves into existence. The soft edges of his face matured and elongated into sharper versions. His pecs popped again and their pink nipples turned brown, darker than Agustín’s and larger, begging to be sucked. Abs came in mimicking Agustín’s, as the belly fat was done away with. 

The tremors made his feet and hands grow in size, but there was still no escape. Ian’s body had transformed, getting older and stronger than before. Leaner, but no less fit, than Agustín’s. The tremors coalesced back in Ian’s head as new memories shook themselves into existence. Agustín was his older brother and helped Ian—no, not Ian— Ramiro, get this job. Then he got a flood of desires copied directly from Agustín as images of his own father flooded his head in a new light. Ramiro’s ripened balls couldn’t take the intensity of his brother’s desire and came inside the underwear passing out.
 
The next morning, Agustín woke his younger brother up as the sun was rising. Agustín had no memories of Ian or his father. All the memories the three had made together were only known to Ramiro. The new world Ramiro woke up in had replaced Agustín with himself going after Dave, his former father. The Moreno brothers were a skilled team at weeding out men for Ms. Gretchen, but Dave was Ramiro’s solo target. Mostly because in this new reality Ms. Gretchen wasn’t afraid to ride Agustín’s cock more freely, as there was an extra person to watch the pool. 
 
Today, however, Ramiro would do more than entertain a guest. Once the second plate of watermelon was gone, his lips were around Dave’s cock. The man’s pants flung off to the side. A strange sensation for Ramiro. To suckle on the cock that made him and yet hadn’t. The taste and smell were exquisite as Dave lovingly cupped his head. His former dad didn’t rush or command. The two simply understood each other. Then Dave’s cock exploded, sending Ramiro’s ex-brother and sisters across his tongue and down his throat. 
 
Dave’s legs were shaking as he caught his breath, “I don’t have a pool, but…what if you worked for me?” The look on his face was dazed and love struck.
 
Ramiro Moreno found his way back inside the Beckinsale house. He even got his old room again. From pool boy to house boy. Never once did Dave mention Agustín. Ramiro was the cool one in the man’s eyes. Ramiro didn't even have to do anything, much like with his brother, it was hard to consider what he did ‘work’ in any capacity. Maybe he cleaned the house here and there, but it wasn’t so bad. After all, it helped establish a routine.
 
“Morning, Son!” Dave would say kissing Ramiro on the cheek, he started to really love that phrase and Ramiro never contested it. There was also something he said was undeniable about Ramiro calling him ‘dad’. “Coffee smells good today.” Dave would wrap him from behind.
 
“You say that every day.” Ramiro laughed, pouring a cup of coffee with a hard cock pressing into his ass cheeks. He had a hoodie on for the cold, but the mornings were typically for being pantless. Dave had his own favorite uniform for Ramiro to wear. Something that really put Ramiro’s best assets on display. 
 
“Only because it’s true,” Dave lifted Ramiro up, and sat him on the table, legs spread wide. Time for the man’s favorite question of the day. Who was going to be drinking and who was going to get something more. Ramiro lifted his hoodie as a reminder for what was available, then he asked it:
 
“Alright dad, coffee or cock this morning?”