The Ballad of Leo

by Bear Stories

18 Jul 2023 1096 readers Score 9.3 (24 votes) PDF Mobi ePub Txt


Zack slammed his hips into me over and over.  His cock was riding along my prostate right where I liked it.  His beat kept getting harder and harder as he approached cumming.  My face was pressed into the leather of the chair I was kneeling on.  His hot seed started flowing inside my ass as he gave his final thrusts.

Me: That was amazing bro!  Blow me on the barstool!

Zack: Man, give me a sec.

It had been two weeks since I moved into Zack’s.  I had been taking full advantage of the situation.  We’ve been having sex daily. ...well, more like hourly, but that was unfortunately coming to an end.  His parents were coming back tomorrow and he had signed up for a night school to finish his degree and go to college this next semester.  We had both been accepted into the same college, but with the condition he gets his diploma before the deadline.  Being rich he had some strings he was able to pull. But he promised that our arrangement would continue at college.  But for now we were having as much sex as possible, on as many pieces of furniture as possible.  

Zack: This is so much fun man.  Drew was nowhere near as fun as you, but he also didn’t let me near his ass. 

Me: Are we going to have time for this at college?

Zack: Yeah, it’s just a formality for me.  I am already prepared for the classes I’m doing.  I’m going to have a ton of time this semester.  But next semester I do need to focus.

Me: I’ll be busy as soon as I arrive, but I’ll come over as much as I can.

Zack: Alright, I also see us spending a lot of time together after college.  We’ve been friends our whole lives, we're not going to stop because we’re friends with benefits now.

Me: No, I imagine the opposite actually.

Zack: Alright! Blowjob then I get round three!

I wish I still had the stamina I had back then.  The next morning Zack woke me up early.  Very early. I was not happy getting up and moving after all the… exercise I got the previous night. 

Zack: My parents are on the way and the maid said she’s going to be late.

Me: So?  The house will be a little messy, it’s the maid’s fault.

Zack: It's not the maid’s fault, she cleaned this house nicely yesterday and last night we messed it up again during our sexcapade!

Me: Shit! Right. We need to clean fast.  But give me five more minutes… 

Zack stared at me as I flopped back into bed.  He didn't move.  I watched the clock closely, it ticked ever so closely.  Zack didn't move… once the clock showed five minutes passed I got up.

Me: Okay let's do this. 

Zack: Most of it was in the basement, so if we keep them from going down there we’re fine.  The rest of it is easy to clean.

We ran around like madmen as we grabbed cleaning supplies, used the vacuum, arranged the pillows and everything else we knocked over that night.  I ran outside and made sure the lawn was all clear.  In about 20 minutes we got the place looking new and shiny.  His parents arrived shortly after.  The first one out of the car was a man with a hefty build and a thick beard.  He wasn’t tall, but he had thick arms that clearly had a lot of muscle.  He had black slacks a white dress shirt and a black vest.  He opened the backseat door.  Zack’s mother stepped outside.  She wore a white dress with a fancy hat.  She was difficult to look at in the sun.  her husband came out after her.  He was tall with a fancy mustache.  He looked like a cartoon villain.

Mrs Telthorn: Zack, my handsome boy! How are you?

Zack: Hello mother!  I’m great!

Mrs Telthorn: How was your graduation?  I’m sorry I missed it!

Zack: Oh, trust me you didn’t miss a thing.

Mrs Telthorn: I will make it up to you.  I have to have your father come down this summer to have a celebration.  Anyway frank and I must head to bed… Our private plane  was damaged and neither of us can sleep on a public plane and our hotel was canceled… and…  wait… who is this?

Zack: This is Leo.  You’ve met him before!  He lived in the town we were in before you married Frank.  I promised he could stay with us until he heads to college.

Mr Telthorn: Marvelous!  Lord knows you need to spend more time with friends.  

Zack: I was like, the most popular guy at school…

Mr Telthorn: Oh,   …I apologize, I must have been thinking of my other son in england.  You two look so similar!

Zack: I’m half Asian…

Mr Telthorn: All races are the same in my eyes boy!

Zack: Um… that’s good… I think…

Mrs Telthorn: Come on darling!  Let’s get some rest. We have a plane to catch tonight!

Zack: You’re leaving again?

Mrs Telthorn: Yes there is a last minute wedding we forgot to book but we must attend!  It’s in the country so we’re leaving Dan here this time.

Zack: Uncle Dan is staying!?  Yes!

Mrs Telthorn: We’ll be back in a week or so…  we are not taking any more public planes after tonight!  The jet will be fixed by the end of the week and we will fly back properly!  Have a good day and enjoy yourselves.  You will see us off right?

Zack: Absolutely!  I’ll see you when you wake up.  Sleep well!

His parents headed inside as I realized I had not said a word…  the thick bearded man approached me.  He had a dark coat slung over his shoulder and a pair of dark sunglasses.  His body really filled out his slim fit suit.  He held out his hand.

Dan: Name’s Dan.  Nice to meet you.

Me: You’re Zack’s uncle? He talks about you all the time!

Dan: Yeah, but also no… His mom is my step sister.  

Zack: He's kinda my uncle, kinda my butler, but mostly the only real father figure I ever had.  

Dan: Shit kid… don’t say that!  You make me feel bad for leavin'.

Zack: Never! You do what you gotta do!

Me: It's a bit odd that you work as your sister’s butler.

Dan: I serve that role if necessary, but I served 6 years in the navy and another 5 in the CIA.  I’m an international security agent.  I keep them safe when out of the country.  I have the experience needed for the job.  So I was a natural choice.

Me: Damn that’s a resume… 

Dan: Anyway.  Gotta check the perimeter right away. We need a security upgrade here. You gonna be around?

Me: Yeah, until classes start.  I’ve got nowhere to go.

Zack: He's sleeping in the spare room.

I was not, but I guess that Zack didn’t like the idea of telling him we were sleeping together.

Dan: I guess we are bunk mates then…  I’ll see you tonight.

Dan headed off to check the perimeter of the property.  I turned to Zack.

Me: Really? He sleeps in the place where you said I’m sleeping?

Zack: It's cool.  He is a good roommate.  We aren't going to have the opportunity to mess around for a little while anyway.  I need to spend time with my uncle as much as possible.  Let’s go inside.  The cooks are probably going to be here soon to prepare lunch.  

Later that night we ate dinner with Zack’s mom and her husband.  His mom told hilarious stories about the trip as Dan added some technical aspects that she was unaware of that made it even funnier.  They told stories together well.  It was great that Zack got to spend time with his mom and uncle, but before long she headed out to her next flight.  But the fun didn’t end.  Zack got out one of his video game consoles and brought it to the big TV.

Zack: Dan! You said you’d give me a rematch in that game!

Dan: I was wondering when you would mention it.  Let’s race!  Leo you should join in.

Dan: waved you over.  It was hard to resist anything this man suggested as you always feel like he could snap your wrist with his pinky finger.  Given his history, that may have been true.

Me: Sounds fun.

I sat down next to Zack and grabbed a controller.  The first race went very poorly as I didn’t realize how the motion controls worked.  But I learned quickly.  The second race I actually got fourth place right behind a ‘COM’ with Zack in second and Dan in first.  Dan’s rain as the front runner ended as it seemed like every racer decided to team up on him at once.  He screamed in a way that would be comical if he wasn’t so intimidating.  Zack took first, Dan took third, and I was fourth again.

Zack: Yes! If I take this win I beat you once and for all!  This is also the only track in the game that I’ve seen you consistently miss first.  But I on the other hand have practiced this track and found the ideal cart!  The future is now!

Dan: Don’t choke icarus…

The race began.  Dan and Zack went head to head right away.  I was behind them for the majority of the race, but I got a seeker rocket and knew a perfect moment to use it.  There was a turn where I noticed they both hit the outside edge of the track almost falling off the edge.  So on the third lap I fired and it hit both of them at once sending them both off the edge.  They both screamed and I passed them before their carts could reset.  I passed the finish line shortly after. Dan took second and Zack in third.  The ending score had Dan at the top, Zack second and myself in fourth.

Zack: God damn piece of shit!

Dan: Ha! Nice shot kid!  That almost cost us both the lead.  If we were passed by the computer and you placed better in the first race, that would have earned you the win!

Zack: Rematch! 

Dan: No, no, no, I gotta get to bed.  I have a security system overall to do tomorrow.  You guys have a good night.  I’ll see you soon Leo.

Dan: left the room heading upstairs.  I felt like I realized that I did not know where the spare room even was.  It wasn’t on the list of places we wanted to have sex, so I didn’t even know it existed.  I went upstairs and looked around for a bit as Zack continued practicing his game. I eventually found a room that was mostly empty other than a bed and a night stand.  It had a private bathroom as every bedroom did in that house.  The shower was running and I assumed that it was Dan as he was the only other person here at this hour.  I entered the room and started getting ready for bed.  The shower stopped and in a minute Dan walked out with his towel over his shoulder.  Nothing else. 

Dan: That’s my side.

Me: Sorry I’ll move

I shielded my eyes as I spoke.

Dan: I’m kidding, I don’t care.  Stop hiding your gaze from me.  It’s awkward.  You should be used to dicks hanging out being a football player.

Me: How did you know that?

Dan: I did a background check on you as soon as I found out you were here.  It’s my job.

Me: That was fast.

Dan: Was it?

Me: I'd say so.

Dan: I told you to stop looking at your hand.  If you're that awkward around cocks, go sleep on the couch.  I sleep nude and I don’t want my roommate freaking out about it.

Me: sorry.

I lowered my hand and turned to look at him.  His dick was nice and prominent through his thin layer of pubic hair.

Dan: Dude, don’t stare either! Come on!  Just do what you would do if I were wearing pajamas or something.

I quickly stopped and just got in bed.  We lay there for a while before I heard him start snoring.  I looked over to him.  He was sleeping on top of the sheets with his simi stiff cock on display.  I imagined touching it, but knew that wasn’t the best idea.  I fell asleep late that night.  The next day I woke up and Dan was already gone.  He was ex-military so that should not have surprised me as much as it did.  I headed downstairs for breakfast and found no one in the house.  Zack had always been there every morning.  I wondered where he could be.  I went outside and found Dan. He was setting something up in the middle of the big open space in the backyard.  He was also half naked.

Me: Hey Dan! Where is Zack?

Dan: He's working on homework for his classes.  He has a lot to do if he wants to graduate on time.

Me: You know about that?

Dan: Who do you think got it set up for him?

Me: That’s awesome of you.

Dan: I know he screwed up, but his step dad would be furious if he found out.  

Me: sooo… What are you working on?

Dan: Science shit.

Me: More specific?

Dan: motion tracker.  The landscapers are coming over next month to make a garden maze or something…  All I know is it’s hard to see through and they don’t want cameras all over, so I got this motion tracker that looks like a tall lamp.  It will track anyone who enters the… whatever the fuck it’s called…  Can you make yourself useful and help me with this?

Me: sure…

I reluctantly went to the spot where he was setting up the device and we started work.  He did most of it but I helped him out by doing the mundane tasks, and we both lifted it into the air.  He held it in place as I bolted it down.  The whole process took about an hour.

Dan: Great job, now we need to run this cord to the house.  I’ll get it set up.  You wait here so I can see if it works.

Me: Sounds good.

A few minutes passed before suddenly the lamp turned on.

Dan: Leo, can you hear me?

Me: yes!

Dan: Good.  I can see where the motion sensor says you are.  Can you walk in a circle around the lamp?  Try to stay an equal distance.

I did as told and made a full circle around the lamp.

Dan: Okay, back away from the lamp slowly.

I did as told.

Dan: Now make another circle.

I did as told one last time and made a complete circle from the far distance I was.  It took about three minutes I believe.

Dan: Pefact!  Come to the security room, I’ll see you in a minute.

When I arrived Dan was hovering over a computer, 

I returned to the house, I was hoping to get out of the heat. As I got to the house I was passing the pool as Dan came out.  He was wearing a speedo and had a towel.

Dan: Heading to the pool too cool off.  Coming? 

Me: Um, maybe next time... 

Dan shrugged and continued on. He continued working throughout the day, but didn’t need any more help from me.  Zack got home late and headed straight to bed.  My body was primed for some good sex, so when I didn’t get it I felt horny as hell.  When it was time for bed it was impossible not to watch Dan out of the corner of my eye as he lay down for bed.  He got in bed next to me and fell right to sleep. 

I couldn’t sleep, I was hard as a rock and needed some relief, I wanted to go jerk off somewhere, but last time I tried something when I thought everyone in this house was asleep it ended badly.  Dan was naked.  His dick semi hard once again.  He was asleep.  It was a bad idea, the worst idea even, but I was just a horny idiot.  I reached out and slowly took hold of his cock.  I played with it a bit.  As I did so Dan moaned but continued snoring.  I played until it was fully aroused.  I started gently stroking with a rhythm.  His cock was bigger than Zack’s but not by a lot.  I could smell the stench of a true man’s meat.  I wanted to taste it, but no… I could not do that…

Dan: If you want my seed you gotta go harder than that.

I jumped back. I didn’t realize that Dan had stopped snoring.

Dan: Damn, I thought you were finally over your cock-shyness.

Me: I’m so sorry sir, I just, I… I’m going to sleep on the couch…

Dan: You’re leaving me hanging?  What, mess with a cock, get it hard and leave without finishing the job?

Me: Do you want me to continue?

Dan: Duh! I’ve been waiting for this!  Come on suck me dry!

I hesitated.  Was I dreaming?  Was this a trap? Either way, I wanted nothing more than to shove that cock in my mouth. I got back on the bed and positioned myself and plunged on to his cock.  It was so hot, but it lasted a short time.

Dan: What the hell?  Are you biting me?

Me: No…

Dan: How do you not know how to suck a cock?  That’s gay 101!

Me: sorry Sir.

Dan: oh, I’ll make you sorry.

Dan sprung out of bed.  I ran to the bathroom and he chased me.  He cornered me.  I was scared, he wasn’t tall, but still had an imposing stature.  I didn’t know how angry he was.  He grabbed me and pinned me to the ground in a way where his cock was up against my face.

Dan: This is the choker hold.  Now do as you're told and you’ll be fine… otherwise I snap your wrist, fingers, neck…  whatever I want. Now, Start by getting that cock in your mouth.  And do it fast. 

It was hard but I got the cock into my mouth.  

Dan: Good now use your lips and tongue to apply pressure.  Very good. Now suck in without letting your teeth touch my shaft. Perfect…  Lastly, start bombing your head up and down my shaft. That is it.  Keep that going!  Yeah. 

The cock was so tasty.  I never imagined I would enjoy sucking one.  It was incredible, even if my wrist hurt.  Dan's grip was hard.  I felt like my hand was going to pop off.  His hands were warm and rough.  He started thrusting his hips in and out as I continued sucking.  Dan eventually let go, but he just picked me up and tossed me like a doll onto the bed.  He turned me face up with my head to the edge and forced his cock down my throat again. 

Dan: Take it you little slut… this is what you get when you mess with a man's cock without knowing what to do with it…  Hell yeah you're a fast learner. 

I felt his public hairs all over my face with every thrust he made.  That was amazing, but he also put his hands all over my body grabbing and leaning his weight.  It was almost too much already, then he fell onto me and inhaled my cock.  I was afraid I may pass out from his actions, but before I knew it, his cum flowed into my mouth. I heard him groan, that put me over the edge.  We took a moment to swallow every drop of each other’s cum.  Dan got up and walked to the balcony.  He opened the door and stepped out.

Dan: I wish I had a cigar right now. 

He looked at me… A face of worries replaced his normally Farley happy one. 

Dan: Are you alright?

Me: Yeah, but you really hurt my wrist.  And back… and legs… mouth… 

Dan: Shit! Sorry, let me take a look at you.  

He came to my side and investigations on my injuries started.  He was very careful and gentle. His hands were rough but not as much as before.  

Dan: Sorry.  Most guys go crazy for that spec ops shit… I should have known you’re not ready for that.

Me: It’s okay.  I can’t say I didn’t enjoy it.

Dan: Well, that’s good…  but I’ll go easier next time.

Me: That's fine by me.

Dan pulled me into a kiss.  I had kissed a few people, but this was softer, slower.  It was beyond anything I ever felt before… I wondered, could this be what love felt like… But I was so young, I wish I knew better.