Jerking With Reggie After Work

The summer after we graduated from high school, a few friends and I took jobs as lifeguards at the community pool. It was easy work – long days sitting under an umbrella and watching for signs of trouble. While on duty, we weren’t allowed to have any books, magazines, or newspapers … and smartphones weren’t really a thing yet. So, to pass the time, we turned people watching into an Olympic sport. From behind our sunglasses, we would spy on our friends, neighbors, schoolmates, and random strangers, attempting to uncover hidden significance behind perfectly innocent and completely banal happenings.

Of course, very few things of note ever actually occurred. Most of our “discoveries” were nothing more than the imaginative musings of bored teenagers looking for a voyeuristic thrill. However, on a certain day in the middle of July, something momentous transpired. It was late in the afternoon – I was working the concession stand while my friend, Reggie, sat in the lifeguard chair. Then, Jenny McDaniels walked into the pool area.

Oh, Jenny McDaniels! She had been a senior when Reggie and I were freshman. With her cascading golden hair, perfect breasts, tight butt, and long, slender legs, she at once excited and terrified every adolescent boy in the way that only an attractive, older woman could. Capitalizing on her stunning good looks, she had left town after finishing high school to pursue a modeling career. No one had seen her since, but she was just as I remembered. After reaching her seat, she opened her cover-up to reveal the skimpiest black bikini I’ve ever seen.

Reggie’s jaw went slack at the sight of her nearly naked body; though his eyes were hidden behind mirrored aviators, it was clear that he was gawking at her. He continued staring as Jenny, no doubt aware of her audience, began to apply sunscreen in a very deliberate, meticulous fashion. Afraid that Reggie was perhaps being too obvious, I coughed loudly from the concession stand to get his attention. He turned his head toward me and flashed a mischievous, unrepentant grin. I returned it with one of my own. Then he dropped his sunglasses to the end of his nose, looked right at me, and mouthed, “DAMN!”

Jenny remained at the pool for the next couple of hours, soaking up the summer sun. I eventually got my turn in the lifeguard seat, but by then people were beginning to filter out. Jenny left soon after Reggie took his final shift in the lifeguard chair. By then, it was a little after 5:00, with less than an hour left before the pool closed. The pool manager, a middle-aged municipal employee, had left around 5:30, trusting Reggie and me to put everything away and lock up. At exactly 6:00, Reggie blew the whistle and announced, “The pool is now closed. You don’t have to go home – but you can’t stay here!”  

After Reggie and I put the equipment away, locked up the concession stand, and cleared out the stragglers, we walked to the shower area in the men’s locker room. Here, we stripped off our trunks and proceeded to wash off the day’s accumulation of sweat, chlorine, and suntan lotion. I should point out that neither of us viewed this activity as strange or novel – Reggie and I had been on the swim team together all four years of high school and had seen each other nude hundreds of times. We didn’t shower together after every shift … but later that evening, we were planning to meet some friends in town after work. Rather than waste time by returning to our respective homes, it made sense to clean up at the pool.

I should also mention that Reggie and I were part of a group of boys from the high school swim team that would regularly jerk off together. This had started during our freshman year, when the five of us were at a sleepover. After being shown some porn on a laptop and having no private place in which to do the deed, we decided it wasn’t a big deal to masturbate in front of each other. Thereafter, jerking off became a regular event whenever some or all of us would get together. This was especially true throughout our freshman and sophomore years.

However, these sessions became less frequent beginning our junior year, when a few of the guys began to start dating and become sexually active with girls. Reggie was the first person in my friend group to lose his virginity and had causally dated a string of girls throughout his last two years of high school. Similarly, I had begun dating my first serious girlfriend, Chloe, during the final months of my senior year. By the time the events of this story took place, it had been over a year since the last time Reggie and I masturbated together.

As Reggie and I showered side-by-side in the open, white-tiled room, I couldn’t help but wonder what the future held. In a few short weeks, we would be off to different colleges in different states. Many of my close friends were likewise leaving our small, Midwestern town to pursue their education hundreds of miles away. What would become of the people I had known my entire life? Would we keep in touch? Or would we be like Jenny McDaniels and only come home once every couple of years?

“Yo, Alkibiades.” Reggie’s voice summoned me back to the present. “What are you thinking about, buddy?”

Unsure of how to express my sentiments, my mouth blurted the last thing that crossed my mind. “Jenny McDaniels.”

Reggie smiled wide. “My man!”

I crinkled my nose in disgust. “Not like that, you perv.” I paused for a second to collect my thoughts. “It’s just that … no one has seen her in, what? Three years?”

Reggie shrugged, “Something like that.”

“Doesn’t that seem weird to you? She doesn’t even come back for Thanksgiving or Christmas?”

“What’s your point?” Reggie asked.

“I guess … I don’t know. Will that be us from now on? You, me, and the rest of the guys? This time next month, I’ll be in Ann Arbor. You’ll be in Madison. Chris will be in Chapel Hill. Tim is going to Clemson – and Seth will be in fucking Santa Barbara! Will we only see each other every few years? Once this summer is over, will we only get together at weddings and funerals?”

Reggie looked pensive for a second. Then he closed his eyes and shook his head, sending water droplets in every direction. When he opened his eyes again, he looked at me with a serious expression. “Let me be real with you for a second, bro.” To emphasize the point, he raised his right hand. I gripped it with my own. “I don’t know what’s going to happen … but you, Chris, Tim, Seth – I grew up with you guys! We may only see each other a few times per year, or once a decade, but we’re best friends for life! If you ever need anything, I’ll be there!”

“Thanks, man – I really appreciate that,” I responded. We then pulled each other into a hug.

Reggie and I were about the same height, he perhaps being one inch taller. He whispered in my ear, “You’re my boy, Alkibiades!”

At this, we each threw our left arm around the other’s shoulders and pulled closer. We had done this hundreds of times before … a simple bro hug. But we were both naked. The combination of flesh-on-flesh contact and warm water caused our cocks to swell. At the same time, we both became aware that our penises were touching. We jumped apart.

We stared at each other for a couple seconds, laughed nervously, and went back to showering. To diffuse the tension, after a minute or two I said, “Sorry Reggie, I didn’t mean to get all heavy on you. One phase of our lives is over, the next is beginning – and I don’t quite know how to feel about it.”

“Don’t worry about it, Alkibiades,” Reggie responded. “Believe me, you’re not the only one. But …” He cocked an eyebrow, “How could seeing Jenny McDaniels possibly make you think of THAT?”

“Hey,” I put my hands up in a gesture of surrender. “It’s not that I don’t enjoy looking, but it’s not like I would fuck her. I have a girlfriend now, so there’s no point in fantasizing about it.”

“I don’t believe in labels,” Reggie said breezily. “That way, when opportunities arise, I’m free to pounce on them.”

“Uh huh,” I snorted. “And how many girls have you ‘pounced on’ in the last couple of years?”

“I don’t keep count,” Reggie answered without a hint of modesty. He shrugged, “More than ten, fewer than twenty.”

“You’re a slut, bro.”

“Don’t be jealous.”

“I’m not jealous.” I sighed, “But this entire conversation is stupid. It’s not like either of us would ever have a chance with Jenny McDaniels.”

“Speak for yourself, Alkibiades.” Reggie turned toward me, flashing a smile and throwing his arms wide open, shamelessly exposing his naked body. “When Jenny left, I was only a boy … but now,” he motioned up and down the length of his torso, “I am a man. How could she possibly resist this?”

I stood still for a second, taking in the sight of him. The only thing Reggie wore was a puka shell necklace with a small shark tooth that dangled at the base of his neck – a souvenir from a trip he took to Florida over spring break. He was tall and tanned, with hazel eyes and a shaggy mop of light brown hair. Reggie’s physique was lean but not overly muscular; he still possessed that adolescent litheness typical in young men who haven’t entirely filled out. His penis was thick and circumcised, slightly engorged from the warm water of the shower and thoughts of Jenny McDaniels. It stuck straight out, resting on his large, shaved balls. Despite having thick hair on his lower legs, the rest of Reggie’s body was bare. The only exception was a well-groomed bush above his dick, which tapered into a treasure trail that ended at his navel.

I couldn’t deny that Reggie was handsome … even still, he was no Adonis. His large, crooked teeth and facial acne belied that comparison. Plenty of other guys from our school were better looking or more athletic. Rather, what set Reggie apart was that nameless quality that ensured he was always the center of attention, the life of every party. While I was shy and awkward, Reggie never hesitated with a joke or pithy comment. Where I struggled to fit in, Reggie was effortlessly cool. For as long as I can remember, people had been drawn to Reggie. It’s what made friendships and romance so easy for him. Truth be told, that’s actually the reason I envied him – not because of the number of girls he had bedded.

“Alright,” I conceded. “If anyone from our grade could bang Jenny McDaniels, it would be you. If you manage to do it, I’ll buy you a drink once we’re 21.”

“You’re on!” Reggie laughed. He threw his head back and closed his eyes, allowing the water from the showerhead to hit him squarely in the chest. “Mmmm … Jenny is so fucking hot! Those tits, that ass! Her suit today didn’t leave much to the imagination. You know she’s gotta be wild in the sack. Bet she could even teach me a thing or two.” He sighed, eyes still closed. “There’s nothing quite like it, am I right?”

“I’ll have to take your word for it,” I replied.

Reggie’s eyes shot open; he turned his head to face me with a questioning look. “What does that mean? Don’t tell me you’re still a virgin.”

I nodded.

“How?” Reggie asked, amazed. “Haven’t you and Chloe been going out for like four months? Surely that’s enough time.”

“Dude, it’s not like that,” I said. “I actually love Chloe. She’s very religious and wants to wait for marriage, and I’m completely fine with that.”

“Huh,” Reggie grunted. His expression changed, becoming more contemplative. “Don’t take this the wrong way, Alkibiades – but do you believe in that stuff? I mean, I’ve known you for a long time and you’ve never struck me as a particularly …” he paused as he struggled to find the appropriate term, “spiritual person.”

“That’s a fair question.” I sighed. “Look, I’m not trying to make a profound philosophical argument or anything, but here’s what I know. Chloe could have any guy she wanted – and for some reason, she chose me.” 

I shrugged. “There has to be a god.”

“Who am I to contradict such unassailable logic?” Reggie responded in a joking tone. “But speaking of momentous revelations,” he continued more neutrally, “did you just use the L-word?”

“Yeah, I guess I did,” I replied, somewhat abashed. “Chloe and I haven’t even said it to each other yet, but it’s how I feel.”

“Good for you, Alkibiades – I’m happy for you, truly,” Reggie said.

“Thanks, amigo.”

“One question, though …” Reggie motioned to my hairless, cut cock. “Why are you still shaving your pubes if you and Chloe are waiting for marriage? Swimming ended months ago, surely you’re not just doing that for your own enjoyment.” He looked at me expectantly.

“Well … Chloe’s not THAT religious,” I responded with a lascivious grin.

“Hah, I knew it!” Reggie exclaimed. “What kind of stuff do you do?”

Knowing I couldn’t squirm out of this line of questioning, I decided to give in and satisfy Reggie’s curiosity. Although I didn’t think Chloe would approve of me sharing the intimate details of our relationship, I doubted that Reggie would tell anyone. I also figured that anything we had done surely paled in comparison to his own exploits.

After a few seconds of hesitation, I said, “Basically everything except actual sex.”

“Fingering, hand jobs?”

“You know it.”

“Oral?”

“Yup.”

“You both perform and receive?”

“Uh huh.”

“Nice, man.” Reggie thought for a second. “Toys?”

I laughed. “Yeah … I got her a vibrator for our two-month anniversary. If I’m struggling to get her off, that thing helps me over the finish line.”

“Damn, wasn’t expecting that. Who’s the slut now?”

“Definitely still you.”

“Eh, you’re probably right,” Reggie admitted. “Okay, last question – does the carpet match the drapes? I’m curious because I’ve never been with a redhead.”

“Wait, you mean … I’ve had a sexual experience that you haven’t?!” I exclaimed. Reggie reached over and gave me a light shove.

After I recovered my balance, I said, chuckling, “Yes, the carpet does indeed match the drapes. Chloe is very self-conscious about her pubic hair and prefers to be completely bare, but I asked her to leave a little patch because I think it’s sexy.”

“Obviously,” noted Reggie, pointing down at my now-erect six-inch penis.

I waved my hand nonchalantly. “I get turned on by my girlfriend, so what? Besides, it’s not like you’ve never seen my boner before … and you’re sporting a chubby yourself!”

Reggie reached down and began tugging on his dick. In a few short moments, it ballooned to its full length. It was about as long as mine. However, while my penis was straight, of average girth, and topped by a large, flaring head, Reggie’s cock was thick at the base and tapered toward the top – almost like a torpedo. Reggie’s hand continued sliding up and down his shaft even after he had become totally erect.

“Bro!” I exclaimed, incredulous. “Are you jerking off to my girlfriend?!”

“I appreciate all beautiful women,” Reggie said defensively. “Besides, I’m not jerking off.”

“Yeah … sure,” I responded sarcastically. “You’re just rubbing your stiff cock.”

“Heh, so are you,” Reggie noted. I couldn’t deny it – at some point, I had mimicked Reggie and reached for my own aroused member. We stood in silence for a couple seconds facing the tile wall, dicks in hand, stroking slowly.

“Been a while since we did this,” Reggie said quietly.

“Yeah, feels good,” I replied. “Kinda missed it.”

Reggie audibly exhaled – finally, it had been acknowledged! The apprehension of the previous few minutes dissipated, replaced by a familiar camaraderie. Having been granted implicit permission to continue, we both began to stroke more vigorously.

I’ve never enjoyed masturbating while standing, so it wasn’t long before I turned around and leaned against the wall. Reggie followed suit, and after about another minute, we both sank to floor. It would have been quite a sight to anyone who happened to walk into the shower room – two teen guys sitting on the ground, naked, mere inches apart, pleasuring themselves. Thankfully, we were completely alone and free to pursue our activities in total privacy.

The monotonous sound of rushing water from the showerheads was broken by Reggie’s conversational voice. 

“How long has it been since you got off?”

“Three days,” I said. “Chloe and I messed around the night before she left for her family vacation.”

“How long will she be away?” Reggie asked.

“Another two weeks.”

“Ouch, that sucks,” Reggie responded sympathetically. “Does she know you handle business yourself?”

“Yeah,” I said. “She doesn’t exactly approve but says she understands.”

“That’s a fine woman you have there.”

“Don’t I know it,” I confirmed. “What about you?

“I jerked off yesterday,” Reggie answered.

“And when was the last time you had sex?”

“Ugh,” Reggie groaned. “I hooked up with this chick at my uncle’s lake house right after school ended. But other than that, I’ve completely struck out this summer.”

“Sorry, bro,” I replied. “But hey, college starts in less than a month.”

“I can’t fucking wait!” Reggie exclaimed as he exhaled deeply. He then rested his head against the tile wall, closed his eyes, and began stroke his cock faster.

“Are you close?” I asked.

“Yeah,” Reggie responded, eyes still closed.

I continued stroking but focused my attention on Reggie’s midsection. His knees lifted slightly off the ground, the muscles in his thighs became taut, and several globs of cum shot from the end of his penis. They landed just below his belly button and dribbled down his stomach, making a sticky mess in his pubic hair. The sight sent me over the edge – seconds later, jizz began to pour out of my dick. It didn’t shoot, like Reggie’s had. Instead, it flowed in a steady stream, coating my head and shaft as my hand continued to move. As my orgasm subsided, I sighed heavily and rested my head against the wall.

“Well,” I said after a few moments. “That was intense.”

“Yeah, buddy,” agreed Reggie. “Just like old times … Hey, um …” He hesitated for a second, considering his next words carefully. Making up his mind, he continued, “Speaking of which – have you ever told Chloe about the stuff we used to do with the other swim team guys?”

“Why?” I questioned as I elbowed him gently in the ribs. “Are you afraid it would ruin your reputation as a ladykiller?”

“You know I don’t care about that shit,” Reggie asserted. “Still, I’ve just always wondered – you know how guys think it’s hot when girls do things with each other? Do girls think the same about guys messing around?”

“Huh … I’ve never thought about that,” I said. “But, to answer your question, I’ve never told Chloe about the things we did. I don’t think she would judge me for it or think less of any of us. But that’s just something between bros that she doesn't need to know.”

“I see that,” Reggie answered. He then abruptly slapped his knee. “I think it’s time to meet the others.”

“Yup,” I agreed.

We got up and washed off, careful to ensure that all evidence of our activities had been flushed down the drain. We then changed into our street clothes and headed into town to meet our friends. Reggie and I continued working at the pool for the remainder of the summer, along with our other friends. Nonetheless, by early August, we had all gone our separate ways. To a certain degree, my fears were realized – as the years have gone by, we see less and less of each other. However, Reggie was right too… on the rare occasions when we meet, it’s like no time at all has passed. To this day, I remain grateful for their friendship and am fond of the memories we share.