Coach Tom's Rookie Mistake Ch. 01

"Come in," I answered the knock on my door.

I really hoped this one would actually work. Who knew finding a high school baseball assistant coach would be so damn hard? So far I've gotten several unqualified fathers of players who are way into the game, clearly living out their high school fantasies through their kids. I've gotten a few others here and there, mostly kids fresh out of college with no experience whatsoever.

Please let this one be different.

The door opened and a younger guy stepped in. I don't know what it was about him, but my breath hitched when I saw his physique. The kid was incredible. Reddish blond hair like light copper, with a few freckles across his nose, he had a bit of a babyface thing going on. But he definitely had the body of a man. A man who seemed to live in the gym. His biceps strained against the sleeves of the tight compression shirt that he was wearing, which hugged every inch of his torso. His pecs jutted out, the fabric clinging to them underneath, framing them perfectly. I could even make out each ridge of his abs through the tight, thin material.

The shirt was clearly too small for him, evidenced by the fact that it left a thin sliver of skin bare around his waist. The kid also had a sharp, defined v-line as well. I'd never seen abs like that on anyone before.

Not only that, but he was wearing too-tight low-rise jeans that showed off his bulging quads, beefy thighs, and I could even tell from the front that his glutes were impressive - jutting out so I could see them. I could see the waistband of a clean white jock peeking out from the top of his jeans.

As he stepped forward, extending his hand, I had to wrestle my thoughts away. I was just admiring this absolute specimen of muscle. That's all it was, one athlete appreciating the physique of another.

"Hey man, what's up? I'm Victor Callahan." I stood up from my chair and met his hand with my own, making eye contact with him. I saw him giving me a cocky smile - like he knew I was just checking him out - er, admiring his physique. Clearly, he was somebody who loved to show off his body, but could I really blame him?

"Nice to meet you, Victor. I'm Tom Connors, but the students all call me Coach Tom. Please, have a seat."

The jock lowered himself onto the chair in front of my desk, and it actually creaked under his weight. I could see that the sides of his ass were spilling out of the seat too. Huh, maybe I needed to get a bigger chair?

"So, Victor, why do you want to be an assistant coach?"

Victor had a glint in his eye as he leaned forward. "Can I be honest with you Coach?" I nodded him on. "I've admired you from far away for a while. I'm not from this town, but one nearby. My team actually played against yours when I was in high school. My coach was okay, but nothing compared to you. I loved watching you work your magic with your players. I've been dying for a chance to work with you."

I balked at the praise this young guy was heaping on me. Now, I didn't think I was a bad coach, but I definitely didn't think I was good enough for a rival team's player to want to work with me so badly.

"I see... well I appreciate the flattery. I try my best. But flattery isn't going to get you the job." I said with my sternest voice. I couldn't have an assistant coach who was too cocky, I needed to have one who would defer to my judgment when necessary.

Victor leaned back in his seat. "Of course, Coach. That wasn't my intention at all, just being honest," finishing off with a wink.

What was going on? If I didn't know better, I'd say this young jock was... flirting with me? No, that definitely wasn't the case. It's probably just that these younger guys are more touchy-feely than back in my day. I just turned 40 this year, so I'm not that old. But being around teenagers all day definitely makes me feel ancient.

"Alright, Victor. Did you go to college?" I could have easily found this information on the resume he had submitted, but for some reason I didn't really feel like looking down at my desk right then.

"Yup, I graduated three years ago, Coach. Actually was a business major, concentration in sports management. I was team captain in college, too."

I was actually impressed. He seemed like a cocky jock, a real 'bro', but I knew from his resume he graduated with a 3.6 GPA. He definitely took school seriously.

"Three years ago? It looks like you have a gap on your resume from when you graduated until now."

"Yup, don't worry though, I wasn't just lazing around. I was just doing some... freelance stuff. You know, self employed."

What kind of freelance work could an aspiring baseball coach do? I guess he might have been giving private lessons.

"Do you have any experience coaching?"

Victor grinned at me again. "A little bit, Coach. I volunteered at a summer camp for underprivileged kids, teaching them baseball. It was more about wrangling the kids than actually playing much ball, but it's something."

Wow, my first impression of him was totally wrong. Just goes to show you shouldn't judge a book by its cover.

I asked him the rest of the standard interview questions. The more I got to know him, the more impressed I was. He seemed level headed, and didn't take himself too seriously. Definitely he knew he was hot as hell, though. Guys like him can't help but want to show off their muscles to anyone, which is why I caught him subtly flexing while we talked.

I set my clipboard down on my desk. "So, final question: what is the real reason you want to be my assistant coach? With your credentials you could work anywhere you wanted, why here?"

Victor's face broke out into another one of his cocky smirks. He leaned forward against, dropping his voice, like he was going to tell me a secret. "You caught me, Coach. I wasn't exactly being totally honest when you asked me that before."

I raised an eyebrow in expectation.

"I wanna be under you, Coach. And I don't mean as a subordinate. Ever since I saw you back in high school I've wanted you. Inside me. I have a serious thing for daddies, and you are the hottest DILF I've ever seen."

I didn't even know how long I sat there, completely frozen with my jaw hanging open. I'd never in my life had someone be so...forthcoming about their interest in me.

Finally, I came back to my senses. "Listen, Victor. I'm flattered but uh, I think that kind of relationship is inappropriate. Besides, I'm not interested in men." I winced a little at that bold-faced lie. After all, every time Luke comes back to visit, I somehow end up balls-deep inside him. And then there was college...

Victor stood up and shrugged. "We'll see about that, Coach. I love the chase. Hope this doesn't affect my shot at the job. Maybe this will help change your mind," he winked while sliding a business card across my desk.

As he turned to walk away, I felt like the wind was knocked out of me. I was right before, Victor's ass was... Christ, it was almost as big as Luke's. Round and meaty, stuffed into those skintight jeans, the top of his ass spilling out over the waist band, and because he was wearing a jock I could see his bare skin, pale and milky white. My dick throbbed in my shorts.

Right before he got to the door he seemed to have dropped something. He bent over to pick it up, and it looked like he was intentionally sticking his ass out, wiggling it a little bit as he took his sweet time picking up whatever he dropped. As he bent down his jeans slid down his ass a little bit - to the point where the jeans were just above his hole. My mouth was getting dry... and I found myself wanting him to bend over just a little bit more, curious about what his hole looked like.

No, wait, that's insane. He's practically a kid for God's sake. And possibly my future employee. I really shouldn't be thinking about him like that. Or any man.

Victor gave me a salute and a grin as he left. As soon as I heard the click of the door closing, I jammed my hand down my shorts to fist my cock. Why the fuck was I so hard and throbbing? I know I have a big dick with a hair trigger, but fuck, I was so horny. I kind of wished Luke was here, but I knew he was away finishing his junior year of college.

But I wasn't going to jerk off in my office, fuck! So I had to let go of my cock, pulling up my shorts and using the waistband to try and tamper it down. I needed to get home ASAP. I don't know how much longer my balls would wait out. I quickly gathered up my things and was just about to rush out the door when I remembered the business card Victor left on my desk. I quickly grabbed it and shoved it in my pocket, then rocketed my way home.

I was so grateful my girls weren't home. Chrissy was away as a freshman at State, while Riley was at soccer practice. I had about an hour to myself before she got home. Which was just the time I needed.

I didn't remember the last time I was this horny. Wait, I did. When Luke had come home for Christmas last year. He and Sammy made sure to stop by my house for a visit, brandishing a wrapped present and a bottle of wine. I knew I shouldn't have drank alcohol with former students... but something about being around Luke made me reckless. Before long, I was buried balls deep in his ass while Sammy stuffed his throat. I dumped multiple loads inside him, each one making Luke hum in contentment and satisfaction. Afterwards, they handed me the present. I protested, telling them it wasn't necessary, but they insisted. When I opened up the present, I was shocked. I thought it was some kind of prank. But Luke said it was for "those times when I need him but he's not around." And now it seemed like it was finally one of those times.

I rummaged through my bedside drawer and found the large tube of plastic. Like a flashlight, but twice as big. What did Luke call it again? Oh right, a fleshlight. It was honestly kind of freaky, since the entrance to the tube was shaped like... well it was shaped like an asshole. It actually looked really similar to Luke's hole, a little bit slit shaped but so damn tight. I pumped out some lube from a bottle and lathered my dick up, getting it nice and slick. With my free hand I roughly pulled off my shorts, which caused the business card to fall onto my bed.

I stared at it for a good while, my cock throbbing the whole time. The front of the business card had the typical information: name, phone number, e-mail. On the back, though, Victor had written something. At first it just seemed like a random string of numbers and letters, but then I realized that it was one of those shortened URLs.

I tore my eyes away from the card to look at my dick. Yup, still hard as hell. I wasn't sure what to do - give into my curiosity about that URL, or work my dick over first. Finally, my brain was able to calm down enough for me to grab my tablet and put the URL in.

JESUS FUCKING CHRIST.

It was one of those membership amateur porn sites. One of those pages for fans of a porn star to watch videos he shot himself. Fuck... why would he send me this?

Then it hit me. The porn star was named "JockPussySlut", and although I couldn't see anything above the neck, I recognized the body. The tight, muscular body with abs like a cheese grater. The round milky white bubble butt that seemed ready to burst out of his clothes.

Fuck. It was Victor.

That's what he meant about freelancing. He moonlights as a porn star.

It would be insane for me to sign up for his page. I mean, that's crazy. Why would I? I've never jerked off to gay porn in my life. I never look at a guy that way... except for Luke. And that time in college. I'm definitely straight... right?

Fuck, I was a goner.

I quickly put in my credit card info and joined his page. And the very top video on his feed made my cock throb so hard it was painful.

Above the video was a caption. 'Taking applications for daddy dick.' I pressed play on the video, my hands trembling in anticipation. My other hand shot into my cock and squeezed it. I didn't want to blow my load just yet. It was curiosity, that's all. It's not every day you meet a porn star.

In the video, Victor was squatting over the front of a chair, his ass facing the camera. Completely nude. I was right about his hole though. It was shaped similar to Luke's. I noticed right away that his hole was really slick and wet, so much so that droplets of what appeared to be lube were dripping out and down his legs. Wait... is it possible that Victor had Carson's Syndrome too? That would certainly explain why his ass is so big.

I was shocked when Victor started speaking in the video. Even though I was home alone I started to turn down the volume until it was just barely audible.

"Daddy, I need you so bad. My pussy is so wet for you. Need some DILF dick to dig me out. You want some of this jock pussy, daddy?"

Jesus, he wasn't kidding about having a thing for daddies. I tried to swallow, but my mouth felt like sandpaper.

My jaw dropped again when I saw Victor pull a dildo from off camera. It was... enormous. Almost as big as me. And I've had plenty of women cry and scream about how I was far too big to ever have sex. Which honestly was one of the reasons why I hadn't gotten laid in a while.

Yeah, that must be it. I'm just so horny and sex starved that I'd get turned on by absolutely anything. Even a twenty five year old jock with a wet pussy begging for daddy dick.

It was like my hands had a mind of their own. Just as Victor started to slather the dildo in his pussy juice, I grabbed the fleshlight and prodded the entrance at the same time Victor started to push the tip of the dildo into his hole.

The moans coming from the video mixed together with mine as I slid my dick into the toy, feeling the soft insides engulf my dick, sinking down to the root. Luke and Sammy said that they bought the largest size - which I was now grateful for, because even then the tip of my dick almost hit the back of the toy.

With my eyes fixed on the video, I started to pump my dick up and down. Before I knew it, I was matching Victor's pumps of that dildo in his ass, our rhythms in total sync. When he pushed the dildo in, I slid my dick deeper into the tool. When he pulled it out, I slid my dick out. When he bottomed out in his ass and ground his hole against the base of the toy, I did the same thing to the fleshlight.

The wet, slick sounds of my dick pumping in and out of the velvety tight flashlight mixed with the squelches of Victor seriously digging out his pussy, uh, I mean ass. The more he shoved the dildo in and out of his tight hole, the more juice gushed out and onto the toy. His voice switched between moans and whimpers, which seemed to send an electric shock to my dick, as well as groans and a string of 'FUCK' under his breath.

"Fuck yeah, daddy. Give me that big load, gonna make me squirt. FUCK!"

As soon as I heard Victor say those words, my balls drew up and I roared in ecstasy. Our voices mixed together, two men screaming in sexual satisfaction as we both came, me from my dick, Victor from his ass.

I kept firing shot after shot into that toy. I couldn't believe the amount of cum I was pumping into this silicone tube. Fuck, there was so much cum it was spilling out of both the top and bottom of the sleeve, dripping down the toy like one of those drip cakes and pooling around my groin.

As I slowly came down from my powerful, earthquaking orgasm, the reality of what I just did hit me. I just masturbated to Victor absolutely railing himself with a dildo while begging for daddy dick. I'd never masturbated to a man before. But, that was one of the best orgasms I'd had in a long, long time. Not since Luke last visited, in fact.

I felt ashamed. That I would jerk off to a young guy like that. What the hell was I thinking? He's almost practically fresh out of college! Besides, he might end up being my new assistant. I can excuse myself with Luke because he needs my help, but this is different... right?

It might have been the post-orgasm haze, but an idea popped in my head. Victor really was the best qualified of everyone I interviewed. It would be unprofessional if I let personal feelings affect my hiring. And there was no reason why we couldn't keep a professional distance. Any time Victor would flirt, I'd just shut him down.

Yeah, that was going to be easy.