Daddy Dominates Boy By The Pool

My family didn’t intentionally plan their vacation during the weekend of Denver Pride. It was a surprise to all of us. When we arrived, there were loads of queer people at the hotel. My Uncle copped to this after a quick phone call. We were using his time share.

I had just turned 18, so I was able to book a separate room for me and my girlfriend, Sara. She was arriving later that evening.

I wanted to drink in the meantime. At the lobby bar, the bartender kicked me out because I wasn’t 21. I barely looked 18 in the right light.

But I was determined. I didn’t want to use the room mini bar, because my parents could find out. I considered the swim-up bar on the other side of the hotel. It had different staff. I determined, so I went upstairs to change into a bathing suit.

I started to pull the red bathing up my legs past my big ass. “Shit.” It was too small. I had gained a little weight senior of high school, especially around my glutes and buttocks. My friends joked that I should bring butter to go with these two huge loaves. Fuck them. I was able to pull up the bathing suit with some force, though my friends were right. It looked like I was smuggling in two large loaves of bread. It was frustrating just looking at it.

My ass was the main reason Sara and I started fighting. Specifically, because ever sense my butt got bigger, my girlfriend, Sara, had been wanting to peg me. She wouldn't let me fuck her until we were married, but she wanted to peg me because 'pegging doesn't count.' Can you believe that? I had never even heard of pegging, and when she explained it, I was so flabbergasted I stormed out. I had no interest in doing that and wondered what suddenly had gotten into her. She responded, “I don’t know. There’s just something about that ass that’s begging to be fucked.”

I bent over to get my shirt from my suitcase and that’s when I heard a riiiiiip.

“Fuck.”

I looked at my ass in the mirror. I saw what I already knew to be true. My shorts had ripped, exposing half my ass crack.

Still, I was determined to get a freaking drink. I decided I would put on a baggy shirt that covered everything. All I had was an overly large, white T-shirt that reached my thighs. I looked like a kid in his dad’s t-shirt. Whatever.

When I stepped out into the bright, blinding sun I remembered it was Pride weekend. Fuck.

Everything seemed to be going wrong. The pool was full of gay men. I hadn’t put on sunscreen. I left my sunglasses up in the room. There was no shade. And all the men: men in rainbow hats with scant bathing suits. Men with muscles bigger than my head. Men with salty-gray beards. Men applying sunscreen to other men.

I found the steps to the pool. I had never swum with a shirt on. It didn’t occur to me that when my white shirt got wet, it would be completely see-through. I guess that’s why frat parties sometimes had wet t-shirt contests. Everyone could see through my shirt as it clung to my stomach and nipples. It didn’t even occur to me until later that my shirt was even see-through where my swim trunks were torn, thus revealing my ass crack and nullifying the only reason I wore the shirt in the first place.

I floated for a few minutes. Maybe it wasn’t all bad. With a pool full of gay guys, I was sure someone one would be willing to buy a drink for me. I scouted. That’s when a tall, burly, beefy man in a black speedo and matching cowboy hat started walking towards me. He had the face and build of a lumberjack model. He tipped his cowboy hat at me.

“You look lost.” His Texan accent made the word ‘lost’ come out like ‘laaawst.’ I was stunned. I had never heard such a strong, baritone voice before.

“Oh, I’m just hanging out.”

“You’re as white as ghost, do you need some sunscreen?” He pointed with his thumb towards his cabana. Bold move, if I was being honest. But there was no way

I was getting in that cabana.

“I’m fine. But thank you.”

“Here. Hold on to my hat, just in case. Get that sun out of your pretty little eyes.”

He removed his hat, revealing a nice head of gray hair. He put the hat on me without even asking. The hat was a little loose on my head and no matter how I tried to fix it, it sloped down.

“Name‘s Hunter.” He reached out his hand out for a shake.

“Jake.”

Considering the size of his muscles and his machismo attitude, I assumed that Hunter was going to squeeze my hand super hard. I prepared for a tight grip and squeezed Hunter’s hand as hard as I could. Truthfully, I was feeling a little insecure in front of this man. The problem was that I squeezed too hard and too early causing me to miss Hunter’s palm, and ultimately squeezing his knuckles.

“Oow boy.” Hunter shook his hand. “Some grip you got.”

“Oh, shit, I’m so sorry.” I felt awful. I couldn’t believe I injured this man just after he lent me his hat.

“It’s fine. You can make it up to me by letting me buy you a drink.”

I hoped I hadn’t given Hunter the wrong impression. I couldn’t believe how well this was going. “Sure. Vodka coke,” I said, grinning.

“You got it, boy.”

As Hunter swam towards the bar, I looked around. People were glancing at me sideways. Red swim trunks, white t-shirt, black cowboy hat —I’m sure I looked ridiculous. I started to feel very self-conscious and swam so that my back was against the edge of pool. The only thing behind me were cabanas.

Hunter came back with more drinks than I expected. “I went ahead and got each of us two drinks. Or you, three, and me, one. If you want to catch up.”

I smiled. This was going really well. “Thank you. Glad you found me.”

“It’s hard to miss the only boy in a white shirt and cowboy hat.”

“That’s true I suppose.”

“I can’t in good conscience let you keep that white shirt on.”

“Oh- I gained a few pounds. I’m trying to hide it.”

“You’re not fooling nobody. Plus, you should be proud of your body. Confidence is the most attractive quality.”

“Maybe. Just not yet.”

Hunter reached his arm out over me and held the edge of the pool. He kept his drink in his other hand. He was slowly cornering me. I stepped sideways.

Hunter leaned in to tell me, “Well, just to give you a heads up, I tend to get my way.”

I was starting to think I should tell this guy I’m not gay. I was only here for the free drinks. But I decided against it. I wanted to at least finish the drinks he already bought. Plus, telling this guy I’m only using him for drinks did not seem like a good idea.

“Can I finish this drink first?” I don’t know why I was asking permission.

“Sure thing.”

Hunter used his finger to tilt the cup to my mouth. He lifted my cup until my head was thrown back and the ice clanked against my lips in the otherwise drained cup.

“All right. Looks like it’s finished.”

I didn’t want to make this guy mad. So, I opted instead to take off my shirt and rest my ass against the pool wall. No one could see my torn shorts this way. I was still getting free drinks. I just needed to create a boundary. I needed this guy to want to keep giving me free drinks, but also needed him to know that nothing was going to happen. If all else failed, next time Hunter went to get drinks, I could just bolt. I was confident I still had the situation under control.

I reached my arms up to get the shirt over my head, but the shirt was sticking to my back. I could feel Hunter looking me over, hungrily. After a few seconds of mild embarrassment, I felt Hunter’s hands on me. I hadn’t felt such big and manly hands on my body ever before.

Hunter helped me take off my shirt, but in the process Hunter’s, I felt something jab at my side. I couldn’t believe that was Hunter’s dick. I was thinking that must be a knee or elbow, but because the shirt had been covering my eyes, I had no way to know for sure. Well, almost no way. I was 100% straight, but I was wondering if a man’s dick could actually be THAT big. Uncharacteristically, I moved my arm in motion under water to see if I could “accidentally” hit it again. I was only curious. My arm didn’t hit anything at first swing. And for some reason that I could not determine, I felt disappointed.

Hunter said, “That’s better. Now you look like you’re in the right place.”

Someone brought over four more drinks and set them down next to me.

Hunter said, “Bottoms up,” and we both chugged another drink. I was starting to feel light-headed and blissful. The sun on my face was warm and relaxing. The water was cooling.

But suddenly I could feel tiny splashes breaking me out of my stupor. Hunter had started to stroke something in the water, which was too big to be his dick. Or so I thought. Could it be that it was actually his dick? I stared for a little too long, trying to make out the size and girth through the water and under his swimsuit. Hunter caught me staring. I pretended to look away.

“You shy, boy?”

“I… no…” I stammered. “I just don’t want to give you the wrong idea.”

“I’ve only got wrong ideas. Very wrong.”

The words scared and tantalized me at the same time. I was frozen stiff except for my rapidly beating heart.

Hunter moved slowly, pushing his weight up against me. He sandwiched me between him and the wall. I felt Hunter’s large erection. I shook my head in fear but was otherwise speechless. He pushed the cup so that I was chugging the last of my third drink. Then he placed the empty cup on the ground. He leaned down and kissed me square on the mouth. I leaned back, but my head hit the wall. I tried to wiggle away, but Hunter held my chin firmly in position. He held my mouth in place. His beard rubbed against my face. I had never felt something so manly. Next came Hunter’s tongue dipping and diving my mouth. I grabbed Hunter’s shoulders because I needed something to brace myself. I feebly tried to push Hunter off me, but Hunter wasn’t budging.

Hunter ran his hands down my body, grabbing my lower butt cheeks, and lifting me up towards the kiss. Hunter forced my legs apart so they opened up around him. From this angle, Hunter’s dick was lined up with my hole. I couldn’t believe it. Everything had happened so fast. One second, I was in control, and a second later, Hunter’s swimsuit was the only thing separating his dick and my hole.

Hunter let out a baritone, “Mmmhhhh. Good boy. Fuck, you have such a nice ass. I can’t wait to get more acquainted.”

Finally, I was able to form words. “What the fuck. Please stop. I think it’s time for me to leave.”

“I decide when it’s time for you to leave.”

“Hunter, please, I really need to go.”

“You’re going to address me as Daddy. And you’re going to do what Daddy says.”

“Please. Can we at least get out of the pool?”

“Please, what.”

“Please, Daddy.” I would pretty much say whatever it took to get this over with.

“Okay. Let’s get you out of the sun. I see you’re starting to get a little pink. My cabana is right there.”

I shook my head. “I can just head back to my hotel room.”

“Horseshit. Unless you would rather have your family walk in on you sucking my dick.”

I couldn’t help but be annoyed, thinking ‘This guy is persistent.’ But I wasn’t worried, because once I had a chance, I could just run back to the room.

“No, sir. I’m going alone.”

“I told you to call me Daddy. And you’re going to do what Daddy says.”

“Or what?”

“Or, I’m going to airdrop a video of us making out to anyone in the proximity with bluetooth. Do your parents have iPhones?” He nodded to a friend on the edge of the pool maybe fifteen feet away. Another older, beefy man was holding up a phone and presumably video tapping us. He waved at us.

Oh no. He had more leverage than I realized. Just moments ago, I thought I was in control. But the control was all Hunter's. “Please don’t.”

“Please don’t what?”

“Please don’t leak a video, Daddy.”

“Okay. Let’s get you out of the sun. We can finish the conversation in my cabana. I have sunscreen in there.”

I was drunk. I had to have had at least three drinks by now. I couldn’t think straight. More than that, I needed the video not to be leaked.

“Okay, Daddy.”

“Good boy.”

I turned to pick up my shirt off the ground, but couldn’t find it. “Do you know where my shirt went?”

“No idea,” Hunter lied.

I didn’t know what to do without my shirt. I couldn’t figure out how I was going to get out of pool without letting people see my ass. I couldn’t decide if it was prudent to tell Hunter about it. And I really didn’t want to get in Hunter’s cabana, but I needed help.

“Look. It’s sort of embarrassing. But I tore my swimsuit in the back. I was hoping to get out of the pool without anyone seeing my ass crack.”

“Hmmm. Exactly how bad is it? Show me?”

A pit fell in my stomach, but I also knew it was no time to be demure. I turned so that my ass poked out from between him in the wall. It was still hidden in shadow. Hunter grabbed my waist to turn me even more, so that he could get a proper look.

“Hmm. I think I see what you mean.” Hunter reached down and stuck his finger in the ripped hole, between my butt cheeks and less than centimeter away from my asshole.

I tensed and Hunter pulled back his hand.

“I see your predicament, but I think I have a solution. I have a towel right there, and with some careful coordination, I think we could get you out of the pool and the towel blocking your butt with minimal exposure.”

I was grateful. Sure, Hunter was coming on strong, but he was also nice. “Thank you so much.”

Hunter climbed out of the pool. His huge muscles flexed. His belly scraped the edge. His glistening body in the sun, as he towered over me, added shade for some brief relief from the sun.

I watched Hunter bend over to grab the towel. Out of the water, the outline of Hunter’s bathing suit showed his semi-erect big dick. So, I was right. It was massive. I could tell it wasn’t even fully hard yet, but still looked monstrous compared to mine.

I was hugging the side of the pool, shaking with anxiety. Hunter came over with the towel.

“Okay. Here we go.”

Hunter positioned the towel perfectly, but it might as well had been a red flag at bull fight for all the attention it was bringing. I could feel people staring. I looked sideways, briefly, and realized that almost everyone I could see was looking back at me. I turned red. Surely, there was a better way.

Shit.

As Hunter put the towel in a curtained position, I hoisted myself out of the pool and onto one foot. The ground was hotter than I thought it would be. Unfortunately, in my hurry, I stepped on the towel causing part of it to fall. Hunter held the other corner firmly in place, but it flapped askew, and was caught by the wind. I tripped and fell to my hands and knees in a doggy position, causing a loud riiiiiip. Suddenly, I could feel the cold air on my full ass. I looked back, and could see the outer curves of both white, round ass cheeks because they were fully exposed. My ass was still jiggling from the way I had fallen. The entire crowd of drunk gay men gawked at me.

The crowd whistled. I froze. I couldn’t decide if I should run home or hop into the cabana. Shit.

I stepped towards the cabana. Because my bathing suit was ripped, I accidentally snagged it on my foot, causing it to fall halfway down my legs. I fell again. This time I landed on my side. My ass was exposed to half of the crowd and my dick was exposed to the other half. Hunter quickly threw the towel on top of me and lifted me up with a level of ease that I didn’t know existed. I had more trouble lifting a suitcase let alone a person. I wrapped my arms around Hunter’s neck and shoulders. Embarrassed, I hid my face in the crevice of his neck. I couldn’t deny I was thankful for the rescue.

Hunter laid me down in the cabana and closed the curtains on all sides.

“Oh my god. I can’t believe that just happened.”

“Don’t worry. No one knows you here. And, honestly, if I had an ass like that, I’d show it to anyone and everyone west of Dallas.”

That made me laugh.

Hunter just handed me another drink. I swigged. He handed me another. I drank more and more. The alcohol made me numb. I wanted the embarrassment and humiliation to go away. My heart was beating so fast, but one thing that I could not ignore, something I did not expect to happen, something that Hunter and everyone had seen, was that I was fully erect.

Hunter grinned at me from behind his full beard. His eyes were scanning me up and down.

I felt my dick pulsating with an energy I hadn’t felt before. My dick had sprouted the few inches creating a tent in the towel that I was too drunk to hide. I tried, but it was obvious. My limbs felt weak. My head was spinning from the heat, humiliation, and alcohol. My cheeks burned with embarrassment, but also arousal. I didn’t know that being drunk would cause this. I assumed it was the alcohol. It had to be, right? It’s not like I’m gay or like to be humiliated in public, like some sort of weird exhibitionist. It’s not like I actually enjoyed showing off my bare ass.

Or, did I?

Hunter closed the curtains around the cabana. Suddenly, we were out of sight. I felt a lot cooler. I was no longer in the heat. I was no longer squinting in the sun. I could feel myself relax and close my eyes. I felt Hunter lay next to me in the cabana bed, which was barely the size of a twin mattress. The only thing separating me from the rest of the world was a thin towel. Hunter started rubbing my thigh, slowly creeping his hand under my towel.

It felt good. I was drunk. Whatever felt good was welcome. I had no inhibitions. And getting a massage from another man wasn’t gay.

I scooted down so that my head would rest more evenly on a pillow. But it also pushed my crotch closer to Hunter’s hand, which sent a message that I didn’t intend but didn’t want to rescind, either. “Thank you for saving me back there. That was so embarrassing.”

“Well, the best thing to do is to try to focus on something else.”

“Yeah? how do I do that?”

Hunter answered by reaching into Jake’s towel and rubbing his tiny, hard dick. “I can think of something.”

I feebly swiped at Hunter’s hand like it was a fly. I didn’t have the energy or will to do anything more than that. “Wait. No. I’m not gay.”

“Yeah? Well, your dick says otherwise.”

Hunter kissed me and jerked me at the same time. Sensually, at first. Then, ravenously. I could feel his strength as he touched my body. It wasn’t the dainty, small hands of a women. These hands were muscular and broad. The difference was stark. Instead of small hands trying to be powerful and failing to carry weight, these were big hands that carried power effortlessly, even when they were trying to be soft. I quivered below his touch.

That was a new feeling.

My dick was pulsating, trying to grow even bigger than my flesh would allow it. I even stretched and bucked my hips up because it felt so good. My words could deny the pleasure, but my body couldn't. “It’s just being drunk. It doesn’t mean anything.”

“Okay, boy, it doesn’t mean anything. You just like having your dick played with by your daddy.”

“You’re not my daddy.”

Hunter laughed. “Looks like I need to teach you some manners.”

Hunter pushed up my legs, and the towel with them, and exposed my ass cheeks, taint, balls, and dick all in one perfectly revealing view. I wasn’t fast enough to stop him or even fight back.

SMACK!

Before I could register what was happening, Hunter had smacked me hard on the ass. “Oww!”

SMACK! SMACK! He firmly hit both ass cheeks repeatedly. “What do you say boy?”

“Ow! Stop!” I didn’t know what to say. SMACK! SMACK! I just knew that Hunter wanted to be called Daddy. “Fine Daddy, fine!”

Hunter took off his bathing suit revealing one large rod. I couldn’t help take it in. Something about his dick was beautiful and demanded respect. I’m not gay, but it was like a statue in a museum, something to look at but never touch.