The Ballad of Leo

by Bear Stories

30 Jul 2023 1222 readers Score 9.4 (20 votes) PDF Mobi ePub Txt


I woke up in bed alone.  The birds were chirping, the sun was shining, and Damon left a note on the door.  It was just the two of us and the landscapers.  Everyone else was out until tomorrow.  I looked outside at the work area sure enough I saw one of the guys fully naked other than a hard hat, boots, and gloves. His name was Bolton I believe. I knew Mike and Henry's names for a while now, and the fourth was called Ford. 

It's been a nice ego boost the last few days having the four watching, and even cheering for me as I rammed my dick up the ass of their boss Frank. Frank had started pimping himself out to me, and the others enjoyed watching. Frank made his rules clear.  For one thousand dollars I can do anything I want to him as long as it doesn't cause visual harm or prevent him from working.  And I can go until I climax or an hour passes after that it's another thousand.  So far, I've never lasted more than six minutes.  I called out to Bolton.

Me: Hey handsome! Where is Dan?

Bolton: I think he's inside.

Me: Thanks!

I left my room without anything other than a pair of shorts. I looked around the house and found Dan in the garage working on a car.  Surprisingly he had coveralls on. He was working on a car that was mostly covered by a tarp.  

Dan: Mornin'.

Me: What are you working on?

Dan: Just some final touches.  Then this baby is ready to roll. 

Me: Nice it looks like a beautiful car.

Dan: Nice is an insult.  I've been restoring it ever since I left the CIA.  I finally finished it!

He pulled the tarp off revealing a red 1980's sports car.  With a convertible top of course.

Me: Damn that's a nice car!

Dan: I know!  Her name is Veronica…. The only woman I will ever love…. Want to take a ride?

Me: Definitely!

Dan closed the lid to the car and stopped off his coveralls.  Underneath he was only wearing a camo speedo and a watch. He hopped in the driver's seat and started the engine.  The car roared to life 

Dan: There you go girl!  Leo, hop in!

I got in without a word.  The seats were very comfortable. Every part of the car was spotless and well maintained.

Dan: Buckle up buttercup! 

He hit the gas and the car flew out of the garage!  I actually felt like we got air on the way out despite how flat the paving was.

Me: Holly crap!

Dan: Yee ha! Now this is what I've been waiting for!

He drove us on to the road and started driving faster.  His car was incredibly fast.  I was wondering if you modded it with something to get better performance.  The wind in my hair and the handsome, practically naked, bear of a man at my side, I felt like life couldn't get much better.  

Dan: Guess what!

Me: what?

Dan: I'm taking you to the beach!  I got a speedo for you in the glove box, put it on!

Me: Change now? But people can see us!

Dan: No they can't! Come on!

Me: No way man… 

Dan reached down to his speedo and pulled it down letting his cock hang out on full display. 

Dan: See! It's cool!  Just keep it low and no one's gonna see it.

Me: Okay fine, put that away.

I got the speedo out, it was blue and very small.  I pulled my pants down while making sure to keep my junk low.  But as I was naked we stopped at a red light and a huge pickup rolled by… the driver looked over at us.  He took a second look adjusting his sunglasses to get a better look.  His eyes darted from mine to Dan's and back.  He gave an awkward smile…. I was unsure if he was aroused, amused, or just uncomfortable, he then turned onto the next road without missing a beat.

Dan: Woo!  Should we go chase him down and see if he wants a quickie?

Me: No! Now put your speedo back on!

Dan: Come on! No road head?

Me: People will definitely see that.

Dan: Fine.

He pulled it back up, but really what's even the point of wearing anything when it gives you a bulge that leaves so little to the imagination.  I got mine on and didn't say a word the rest of the drive.  Before long however we arrived.  Dan hopped out and grabbed some towels from the trunk.  He handed one to me as I got out.

Dan: Let's go!  

We hit the sand fast, and after it burned our unprepared feet, we hit the water faster.  The beach was big but not many people had arrived yet the beach was almost empty.  We started splashing each other with the cold water.  It was already a hot day, but it was only getting hotter by the minute so the water was very refreshing.  

We ended up in a spontaneous wrestling match.  I was a bit taller than him but dunking was not easy to do.  He was also clearly going easy on me seeing he had the ability to pin me to the floor and shater my spine before I even touched him.  

He ended up dunking me a few times, one of which he got me in a position where I got a face full of his crotch.  I grabbed his speedo and pulled it down his cock sprang out, slapping my face.  I stuck it in my mouth and started sucking as it throbbed. Dan let go of me and I came up for air.

Dan: That was a dirty trick!  I was about to start moaning if I let you continue.

Me: I learned your weakness and will exploit it.

Dan: Is that so?

Dan took a step closer to me pressing his belly against mine, his boner poking my full sized bulge.

Dan: You gonna jerk it off?

Me: Dan, we're in public…

Dan: Sure, sure… but remember what I taught you about leaving a cock hanging?

Me: Yes, but seriously, we can't, it's too risky.

Dan: I think your time with that landscaper has made you rather disobedient… I need to teach you your place again.  Now, reach under the water and jerk me off a bit.

I reluctantly reached down and positioned myself so no one could see from shore.  I took his cock in my hand and slowly started pumping it.  It was a bit exciting.  His scent was strong from the sweat that was building up.  He pulled me in for a kiss.  He was a great kisser, but this was his downfall.  He was distracted, I moved my foot and used it to knock him off his balance and I grabbed his arm, twisted it and threw him into the water.  He flipped over as he fell showing his naked ass to the world.  His speedo also came fully off during the fall and I grabbed it. He quickly popped back up.

Dan: Fuck, my leg!  Shit, you kicked it hard.

Me: Who's been put in his place now?

Dan: Okay, okay, come help me get to shore?

I went to him concerned that I may have hurt him more than I thought.  As soon as I took his hand to help I was once again under the water.  He pulled off my speedo and pulled me back up.  He pressed my back to his chest and wrapped his arms around my shoulders and neck putting me into a headlock.  

Dan: So predictable… Now what kind of fun can two guys have together in a position like this? Perhaps if I...

Dan pressed his cock against my ass.  After a little searching it was pressing into my hole…

Me: You won't give up will you?  And I thought you weren't into butt stuff…

Dan: I enjoy a change of pace now and then…  don't worry if anyone is watching they will assume we're wrestling…

He started pulling me around and making it look like a fun struggle, but as he did so he started pushing his cock inside my ass.  Zack had fucked me before, but even though Dan's cock wasn't much bigger or hurt significantly more…. It was amazing how easy it was to get in… Dan was definitely a pro at this.  Just as I started getting into his groove, I saw a guy looking at us…

Me: Dan, I think we should stop.  Seriously…

Dan let go.

Dan: Okay, if you're not comfortable…. But I need to finish this back at home… let's get a drink, I'm thirsty.

We put our swimsuit on and once our boners dropped we headed back out. There was an area with a small bar and a bathroom.  A volleyball court was nearby with a couple of men in swimsuits playing.

Dan: I left my wallet in the car. I'll be right back…

As Dan was gone I watched the volleyball players more.  One was heavy set with long blond hair and a bit of a stubble growing.  The other one was the real looker of the two.  He was very muscular with thick arms and a fat ass. His black beard was just starting to get bushy and his head was shaved. He was in a short red swimsuit.  Not a speedo, but close.  He had a baseball cap on as well as a pair of military dog tags around his neck, and a pair of sunglasses over his eyes.  After a few minutes of me staring at him he looked over and noticed…. I got really scared, until he lowered his sunglasses and I realized who it was… my old football coach Arnold bangle…

Coach: Leo!?

Me: Hey coach! Odd meeting you here.

Coach: I'm here all summer!  I've been enjoying my life on the beach.

I could smell alcohol on his breath.  The guy he was with started approaching to see what was going on…

Coach: I haven't heard a word about you since you graduated.  How have you been?

Me: I'm good.  I've been accepted into college and I'm staying with Zack for now…

Coach: Really? After what he did to you?

Me: Yeah, he's been making it up to me…. He's also getting into college.

Coach: Good for him. And are you playing football in college?

Me: I don't know… I'm not sure if I'm good enough for college teams…

Coach: Of course you are… you were my third best player, and half the team is playing in college.  You just need to get into shape.

Me: That means a lot coming from you, coach.

Dan: Hey! Leo, who's your friend?

Dan was right behind me suddenly.

Me: Dan! You scared me! Don't do that… Anyway, this is my old Coach, Arnold. Coach this is my… umm… this is Dan!

Dan: Nice to meet you, Arnold!

Coach: Great meeting you, and this guy always lurking around me is my husband Brandon.

Brandon: Sup…

Me: Wait! I didn't know you were…. Married…

Brandon: You were going to say gay weren't you?

Me: What? Nooo….  I…

Coach: It's okay! The school didn't like me being open about my sexuality.  You know, it was a whole deal explaining to parents that "gay" and "predator" were completely different things.  So we just got married recently! Right after I quit the job.

Me: You Quit?

Coach: Yeah.  I got some options lined up… but I need to live the way I want for a change.

Me: That's nice!  I hope the best for you.

Dan: Arnold, By the way, I can't help but notice the tags on your neck… are you ex-military?

Coach: Navy. I was in for a few years. And call me Coach.  It was my nickname before becoming a Highschool football coach and it will be long after.

Dan: I was navy too. What did you do during your service?

Coach: I was a chopper pilot.  I didn't see any combat, thankfully, but it was a life changing experience.  I mostly instructed the newbies on the stuff they don't tell you about in training.  That's how I got my nickname.

Dan: I definitely was in a few firefights myself… but came out unscathed… Be glad you weren't in any…

Coach: Come on! Let's grab you guys a drink!  On me!

Me: I'm only-

Coach: Shh! I know you are Leo.  But the bartender doesn't, and no one brings ID down here…. Plus with the stubble you're growing no one's going to ask.

We sat at the bar and Coach ordered a round of hard liquor.  I hadn't drank since the incident months ago.  As we enjoyed our cold beverages, the conversation continued.

Dan: So Brandon…. What's your story?

Brandon: Man, I've been driving around America in my van.  Coast to coast.  I don't think I'll be continuing that now that I tied the knot.  Now my winters will be with my husband.

Coach: We can still go on road trips, we just need a camper.

Brandon: It's not the same…. When it's just you and your van you can go anywhere… with a camper it's so official.  Planned.  Plus, there are places you may not want people knowing you are making love to another man.

Coach: That's true…. I definitely don't want to be in a situation like that anymore…

Me: I don't blame you, it must have been hard being gay in the navy. 

Brandon: Yeah, I wish you never had to go through that…

Dan snorted and Coach smiled.  They looked at each other for a moment, then suddenly burst out laughing.

Dan: Yeah! It's so hard isn't it!

Coach: All that seeking around!  Trying to figure out who's interested in cock!

Dan: Hooooo!  Don't forget about after you find another gay and you need to find a secret place to do it without being seen!

Coach: And the punishment when they find out!  So horrible!

They continued laughing uncontrollably for about a minute straight.

Me: Wait, what?

Dan: Look kid, it's not stated anywhere, but when you're on a ship with only other men for months at a time, eventually men stop caring who the hole belongs to.

Brandon: Wait!  Do you mean?

Dan: When you are willing to suck a dick, there ain't a single sailor who will try to stop you.

Coach: You know, I once sucked off almost half the crew in one day!

Coach jabbed Brandon.

Brandon: Okay, okay, I know you're exaggerating.

Dan: ha!  I was stationed on a submarine that was out for eight months only coming up for supplies and fuel.  No one was allowed off the tub. Long story short, eventually we stopped pretending to hide it and I started making rounds taking guys to the side and sucking them off right at their station in front of everyone.

Coach: Once the captain came down to see me hand to hand combat training with a low ranking  admiral and told him, "Whenever you need someone to fly, fight, or fuck, this is the best man we have!"

Dan: So, did he take that offer?

Coach: He seemed rather offended, but within a day I was giving him the old "Southern Corkscrew".

Dan: Classic!  My captain's favorite was always the "Jones' Treatment".

Coach: I've never heard of that one.

Dan: It's like the "Deep seed dive", but you need three people for it…

Me: Brandon, do you know what the hell they're talking about?

Brandon: I have no clue…

Coach: You know, maybe we should… compare notes sometime… 

Dan: No one will use the changing room for a while…

Coach: I bet not…

The two locked eyes for a moment, then, without a word, chugged down the rest of their drinks and got up.

Coach: Babe, can you watch the door?

Brandon: Sure Sugar.

They walked quickly to the men's changing room.  Dan held the door open for Coach, then as Coach entered Dan slapped his ass.

Me: Are they?

Brandon: Yeah… My husband gets horny and bold when he gets a drop of alcohol in him.  I learned to just let him have his fun until he sobers up.

Brandon and I sat in silence for a while, but I eventually randomly brought up a fact about dog behavior.  That sparked a friendly conversation about old family dogs.  We were having a nice time but I couldn't get my mind off Dan and Coach.

Brandon: You're staring at the door again.

Me: Oh, wait, again?  I did it before?

Brandon: You can go in if you're that curious…

Me: Oh, no, I'm just… 

Brandon: Come on, let's make sure your boyfriend isn't choking on my husband.

Me: He's not my boyfriend…

Brandon: Sorry, I meant fuck buddy. 

Me: oh…. That's quite the slip up...

We entered the changing room, and as soon as the door opened I heard the familiar sounds of Dan moaning.  We rounded the corner and saw a beautiful sight…. 

Coach was kneeling on the ground with his back to the wall, his hands grabbing Dan's hips.  Dan's hand wes pressed against the back of Coach's head, pulling him in as he thrust his cock into Coach's mouth over and over.  

Dan: Fuck yeah! That's the way I did it for the Lt. Commander's anniversary!  

Brandon: Looking good guys!

Dan's head spun around fast.  He looked at us wide eyed.

Dan: Shit!  I didn't hear you come in!

His eyes darted from me to Brandon and back several times.

Dan: Your husband is great with his mouth!

Brandon: That's why I tried to keep him for myself.

Coach pulled himself off Dan's cock with a loud pop.

Coach: This talent needs to be shared!

Brandon: You're such a slut!

Coach: It's called a player!  Now, let's get back to what we were doing, big guy.

Coach started sucking off Dan again.  The look on Dan's face was of pure joy.  He looked cute smiling.  I wished I could make him smile that big with a blowjob.  Brandon pulled his cock out and started jerking off.  I honestly felt kinda uncomfortable.  I was definitely aroused, but my coach was always a hero to me.  Always there when I needed him. 

Me: Hey, I'm going to watch the door, you guys have fun…

Dan: Come on, you gotta try this mouth first!  

Pop

Coach: Yeah! Come on Leo!  I know you want to give your coach a taste!  I saw the way you looked at me in the shower!

He stared me in the eye with a seductive smile.  He licked his lips and like that, I was his…

Me: Okay, I suppose I can try…

I linned myself up to Coach, he opened up his mouth as I slowly slipped my cock in.  His lips locked against my shaft and he got to work.  His moist mouth was unforgiving as he worked my cock.  It felt like only a second passed but I'm sure it must have been longer.  Dan and Brandon jerked off watching us, it didn't bother me as I got used to being watched by the landscapers as I fucked Frank.  I actually liked it.  Made me feel confident. But I snapped out of whatever trance I was in when Coach released me with another pop sound.

Coach: Sailor! Attention!

Dan: Sir!

Coach: There is V.I.P. in need of attention next to you!  Put your training to work, and prepare for oral penetration!

Dan: Sir, yes sir!

Coach got back to work as Dan knelt on the ground next to him.

Brandon: Sure, why not.

He stood next to me and let Dan start sucking him.  

Coach: Now this is a blast from the past! Eh, Dan?

The four of us stayed that way for a while, only the sounds of sloppy wet suction and moans filling the air.  Brandon slapped my ass and I slapped his back.

Brandon: Shit… that's good… God! I need a cock in me!

He ran to a bench and leaned over it.

Brandon: Someone fuck me I don't care who just do it!

Coach: Sailor!

Dan: Already on it, Sir!

Dan got up, ran over to Brandon, and lubed up his cock with spit.  I wasn't able to see him penetrate, but he started fucking Brandon.  I wanted to get a better view.  I never saw Dan do anal before.  I was rather jealous.  Coach stood up and whispered in my ear.

Coach: You're all lubed up… go for his ass!

Me: He doesn't like anal.

Coach: Trust me!  You just got to get him in the mood and he's there now.  Go!

He slapped me on the ass.  I walked up behind Dan and positioned myself.  I knew I couldn't get in while he was bucking his hips, so I grabbed his hips with all my might and stopped them, then quickly shoved my cock in his asshole.  Luckily I got it on my first try…

Dan: Leo!? That was smooth as hell!  How'd you do that?!

Leo: I've been getting practice.

Dan: Damn kid!  That's more than just some practice!  You're a fucking prodigy!

I started to move my hips, but before I could, Coach's hands stopped me. 

Coach: Hold your horses!  I'm joining too!

His hands spread my ass cheeks as he pressed his cock against my hole, I realized that I didn't take a good look at his cock earlier.  As it entered me I knew it was at least eight inches and twice as thick as Zack's.  It hurt as it entered me, but I loved every inch…. He pressed his hairy chest against my back forcing my chest against Dan's.  

We started the four man train fuck, but honestly, I can pretty much as soon as Coach touched my prostate….  Dan either didn't notice or didn't mind.  We went on much longer than we should have.  Eventually Brandon declared that he was cumming, and like dominos, Dan started his usual moaning, and I felt hot jizz in my ass.  When we came to a hult we all gave out a collective sigh, then a collective laugh.

As we were about to get out of this awkward position, we heard the door swing open and some whistling.  A man turned the corner before any of us could react….  He looked like an average Joe, probably some father down here with his family, or something like that.

Man: What the-! What is-!

Coach: Hello! Um… this is awkward… isn't it…The man was in shock and didn't move a muscle, or so I thought, until I looked down… his cock was clearly erect through his bathing suit….  I looked at his face again, I recognized him. He was the guy in the pickup truck who saw us on the drive to the beach...  I looked at Dan and he looked over his shoulder at me.

Dan: Who down for round two?