The Halloween Costume Debacle (part II)

Welcome to the second and final part of our Halloween's special!

Let me know if you would enjoy more short stories in the future, or if you would like for Dennis and Leonard to return!

The Halloween Costume Debacle!

Part 2: The only way it will fit

I return to my work station, a little flustered.

This is a euphemism not to say that I am beyond excited and that my hands are shaky.

I have a job to do and I try to ignore the naked hunk on my bed. My dick though is clearly hard.

I believe that he can see it but Leonard is back to scrolling on his phone and sending vocals to Marissa.

Now that I have his measurements, I cut the pants already turned into a pair of shorts to make them into an even smaller pair of underwear.

I have taken this seriously; the black latex piece of fabric should fit him nicely.

“Are you ready for the fitting?”

At this point, he is lying in my bed, one arm behind his head, the other busy on his phone. He has remained stark naked and his enormous black cock is lying against his thigh.

I am in awe.

As soon as I talk though, Leonard jumps from a bed like a lion. His cock faps against his legs. It hits so hard.

Dang… Why does he have to have such a heavy meaty cock?! Even limp, that thing looks HUGE.

“Always ready!” He claims.

I hand him the tiny leather boxer briefs.

“Here you go.”

“Wow… You weren’t kidding… That doesn’t leave much to the imagination.”

“It’s still more fabric than what your girlfriend’s wearing.” I point out.

“Fair.”

He takes the boxer shorts but very quickly struggles to put them on.

“Do you need any help?”

I try to mask the sound of hope in my voice.

I do not think I am very good at hiding my intention.

Leonard may be a jock, but he is not that dumb or naive. Especially when it comes to knowing when someone is into him.

“Sure… How do you want to proceed to get my fat ass and large cock into that thing?”

His smile says it all. He enjoys this very much.

“Let’s do this step by step. Get on the bed and give me your feet, we’ll start by getting the boxer briefs through your ankles.”

If you can believe it, he has not even managed to get to that part yet.

One may even think he has been clumsy on purpose so I would have to give him a hand…

But then, in all fairness, the fabric was sort of difficult to handle and putting the latex outfit on could be considered a two-man job.

Leonard sits on the edge of the bed and lifts his leg in the air. He really is shameless.

Doing so, he offers me an unencumbered view to his slightly hairy asshole.

That literally takes my breath away.

“What are you waiting for dude?” He asks joyfully, his feet in the air.

“Sorry… I… I’m on it…”

I grab both the shorts and one of his feet and I stretch this thing out to make it slide.

(Just so we are clear, I am talking about the outfit here.)

To get it through his feet, Leonard has to reassemble his legs and not spread them so wide.

That is a shame but the best is yet to come.

I pull the fabric through his ankles and lower legs until I get to his knees.

“Dude, it will never fit!” He complains.

“It will! Those things are meant to be tight. It will stretch on you.”

I sound confident but I am not. I am starting to doubt my own measurements. Maybe I have played too much with the limit? Leonard is a huge guy and I have cut the costume without leaving any margin of error.

Once we get over the knees, we can move on to the real difficult part, getting the shorts over his large thighs, big butt, and XXL cock.

“Maybe I should stand up now?”

“Yes, go ahead.”

As he moves, his dick dangles and faps again his left thigh.

I wonder if his third leg has not gotten chubbier since I have first gotten him naked.

In fact, I am pretty sure of it, I have been checking that cock like a hawk on a hunt since he has walked into my room!

I suppose Leonard likes to show off too much and he is getting a little excited.

I find myself on my knees as he towers over me. I look up; his big black cock is obstructing the view to his face.

The foreskin is so close to my lips.

Blessed be the remaining uncut guys in the U.S.!

“What should I do now?” He asks.

The pair of latex mini-shorts seems stuck right above his knees, but then I have a genius idea.

“I swear the fabric can smooth and be easier to work with. We just need to… Well, to lubricate it a little.”

“Wait… What do you want to lubricate now?”

I swear I catch his cock reacting so slightly as he says that.

“The costume!”

As crazy as this might sound, yes, I was still talking about the damn cut-off Batman shorts.

Although… Anything is possible on Halloween night.

“Bro, this is getting weird.” He says, but he has his usual grin on his face.

I let him hang there and search in my bedside table for some lube.

I could have used something more professional we use in class to work on some similar materials but I figure I could as well use the lube normally dedicated to make my asshole more fuckable.

“Don’t worry, I’m a professional.”

I say, toying with him for a change.

“I bet you are.”

Just for the fun of it, he shakes his pelvis and makes his large cock fap his thighs even more.

By this point, there is no way he can miss the huge tent in my pants as I believe that my cock has never been that stiffed.

I am pretty sure that it is leaking in my underwear.

I start lubricating part of the latex fabric and part of his thighs.

“Hmmm…” He lets go of a faint moan.

“You’re okay up there?” I ask as I apply the lotion generously.

I need to make everything slide.

“Yeah… Hmmm… That’s just… This area of my thighs… It’s a bit sensitive.”

I am getting closer to his groin.

Maybe I am pushing this a bit too far? He is clearly getting excited now.

“Oh… Sorry, look, if that makes you feel uncomfortable, maybe I can…”

“I’m comfortable, dumbass! I always am!”

I laugh.

Of course, a guy like Leonard cannot show the slightest bit of nervousness, this would not be “manly”.

“Okay, I’ll just keep going then, I can see the fabric loosening up.”

“Yes, I feel like I’m getting looser indeed.” He replies, jokingly.

I take this as a green light to continue and I get even more daring as I go. I mean, he is obviously letting me have my way with him, I would be an idiot not to have a little fun with it.

Besides, my college experience so far has shown me that this is not because a guy is “straight” that he does not want to try new things.

“See, I can now easily get the shorts higher. We’re almost there.”

As I pull the micro-shorts up, my right hand smashes against his dick, while my left hand is still very much wandering in the groin area.

“Damn… You’re right, it also doesn’t feel too bad… The fabric against my skin… I…”

Before my incredulous eyes, I witness his cock growing even bigger, reaching a firm semi.

“It looks like it even starts to feel good!” I dare say.

“Hmmm… Dude, what have you done to me? Like… The friction… That’s a lot, as I said, I’m a sensitive guy.”

“Sorry, I didn’t mean to…”

As I am speaking, I do not remove my hand from his inner thigh.

His cock keeps growing, it is like I have released or woken up the monster.

“Besides, I’ve been saving myself for Marissa, I’m horny as fuck right now!”

“Man, I can see that.”

“Shit, it’s going to be impossible to get this thing to fit now. My dick is way too big.”

I gulp.

Leonard has a point.

“I… I have to admit, I had not accounted for your erection when I took the measurements earlier.”

He starts stroking himself mindlessly, as if to check if he is really that hard.

“And bro, when I’m like that… There’s nothing I can do to get it down.”

I think I am practically drooling there. I am still on my knees and his dick is erecting like a bouncy castle. An unstoppable rise.

Frankly, it is just a marvellous sight and this gives me the confirmation: Leonard is as much of a shower as he is a grower.

What surprises me the most is his attitude about the whole thing though, it is as if he is purposely letting things derail.

“But what are you gonna do? We should both already be gone right now and… Leonard, you don’t have a costume anymore, we teared it up.” I tell him.

“Fuck… I know… Do you reckon that it would still fit if my dick was not that massive?”

He really wants me to say how big he is!

“What’s your point? We cannot really cut your dick off, man.”

He holds his dick tighter.

“Bro, don’t say shit like that, don’t talk about cutting a man’s dick off, even as a joke. No, I meant, if my dick was not hard, would the shorts suit me?”

“Yes, of course. If you weren’t hard, I could get it over your ass, with the lube, it’d be just fine.”

“Okay then, let’s do something quick, let’s get my massive dong to go down. I need to go to that party or someone will snatch Marissa away from me!”

I am starting to get where he is going with that but I cannot allow me to think about it.

I must be imagining things. 

“How though? How do you want to tame that huge cock of yours…?”

His dick throbs again and at this point, he must be close to full mast.

I promise, this slab of meat is more than nine-inch long, maybe even bigger than ten inches. Properly huge.

I have never witnessed such a gigantic cock in person. I thought this only existed in porn, and most of the times, I even suspected the camera angles to alter my perception of the performers’ genitals.

“Dude, you know there’s only one way how. I’m telling you, when I’m like that, if I don’t cum, I’m fucked. I cannot focus and Leonard Junior doesn’t go back to flaccid.”

He moves his pelvis slightly and accidentally pokes my face with his humongous bone.

Or was it really an accident?

I feel his cock right below my lips and it takes everything in me not to give him a lick. I pull back just a little to be able to speak without having a mouth full of his junks.

“You want to cum? Right here?!”

I know, I should jump on the opportunity of a lifetime but I can hardly believe or process what is happening right now.

He shrugs his shoulders.

“You need to help me out, buddy. You’re gay, right? You shouldn’t mind?”

Okay.

Now I cannot pretend that I do not know what he wants from me anymore.

I finally gab his dick, my fist can barely surround the entire base of his girthy cock.

“I can make you cum… I mean, it’s the only way the costume will fit!”

“Exactly right… Hmmm…”

I start stroking, because what else am I supposed to do?

“Damn, Leonard, your cock is so damn big.” I cannot help myself from commenting.

“You think?”

“Come on! You know it.”

He spits on the tip of his dick to wet his cockhead. For the first time, I go up to the head and massage it, getting it all slippery.

“Yeah, I’ve heard a lot of people say it’s the biggest cock they’ve ever seen. Is it?”

“Wh… What?”

“Is it the biggest piece of man junks you have ever hold in your hands?”

I nod yes.

I am such in awe that I do not think I can speak anymore…  But thank God, I can keep stroking. I feel some droplets of precum sliding through my fingers.

“Hmmm… That’s nice, bro, but like, you need to accelerate the pace, we don’t have all night!”

Immediately, I comply with the instructions.

I pick up some more lube, use both of my hands, and I wank him off more intensely. There’s so much ground to cover, it is insane.

My own cock is aching in my pants.

“Like that? Is it better?”

“Yes… You’re natural at this, bro…”

“Your dick looks so fucking good…”

“You know, if you want to accelerate the process… Hmmm… even more… You can… Hmmm… You can put in your mouth…”

Is he for real?

“Man? Are you suggesting that I…”

“Wanna taste it, bro?”

I stop stroking for a split second and I look at the hard dick before my eyes. It drips with thick precum. It twitches. It wants my mouth.

Finally, I go for it and lock my lips around the slippery cockhead!

Instantly, Leonard’s moans become more ardent, bestial even.

The tip of his cock already fills my mouth quite well, it is so girthy but it is not my first dick and I am adamant to show the big jock what I am capable of.

I swallow more of his demanding dick.

“Hmmm… God… What they say about gay boys is true…”

I wish I could say something but my mouth is quite busy at the moment.

I go even deeper, inch after inch, I want to attempt to swallow the whole thing until I feel the monster-cock tapping in the back of my throat.

I manage my gag reflex but saliva drips from my lips.

“Damn, who knew you were such a bitch?!”

He starts thrusting his pelvis, making me choke.

I feel the tears filling up my eyes but I do my best to hold on.

That dick is not only looking great, it feels and taste amazing. The precum is now oozing in my throat. I grab his ass to remain steady, scratch his beautiful muscular cheeks in the process.

“Yes, take it… Hmmm… Take it good, cocksucker… Swallow my big fat rod…”

The throat-fucking becomes even more intense until I cannot take it anymore, I gag and I spit a huge chunk of saliva on his drenched throbbing dick.

I need a moment to catch back my breath.

“Was it too hard?” Leonard asks.

He seems genuinely concerned.

I smirk at him.

“Who do you think I am? I can handle this.”

I move my head below him and start licking his massive balls. I swallow his two nuts and roll my tongue around each of them.

I know he is full; he is about to cum so much juicy loads. I cannot wait.

“You are a true certified slut!” He exclaims, semi-laughing.

“You need to cum, right? We have to get these shorts to fit! There’s no other way around it.”

I wink at him; he slaps my face with his cock. Dang. It is so hard, it actually hurts.

It hurts so good though.

I keep massaging his balls as he rubs his bone all over my cheeks, my forehead, my lips, even my eyes.

I am bathing in his manhood and I love it.

“Put in in your throat again, bitch!”

Once again, I oblige without a second thought. This time around, he does not fuck my face, I am the one doing all the work, pumping his dick, I am attempting to reach his pubic hair with my nose.

“Grrl… Grrl… Grrl…”

“Milk me, Dennis… Milk me just right…”

The blowjob keeps going and he does not cum.

And there, I have another idea…

My jaw is aching and I take a break from the hardcore sucking.

“You’re not cumming man.” I mindlessly note.

“Just keep going, don’t stop… I was getting there!”

“Don’t you think we could use an even faster method?” I ask, pretending to be innocent although I am not fooling anyone.

“What do you have in mind, naughty boy?”

“From experience, I make guys explode much faster when they shove their cocks in another one of my holes.”

There, I have said it.

For the first time since he has walked into my room, Leonard looks startled.

Surely, he is not “uncomfortable”, since he never is but he thinks about it.

“I’ve never fucked a guy.” He speaks.

“I’m just saying, my asshole is pretty tight and procures nice sensations, but man, that’s your call.”

Leonard swallows his saliva. His dick is clearly reacting positively to the proposal but is his mind ready to take that leap?

What would Marissa say?

She probably would not care much, fucking another bro is not really cheating, right?

“Fuck… Clearly, I have to make my cock go limp… And we have to do that very quickly if I want to have a chance to win the costume contest… So, I have to cum… I suppose it is a mean like any other to get there as fast as possible…”

I look at the jock convincing himself that it is totally reasonable, and called for, to shove his dick in my asshole.

As ridiculous as he sounds, I go along with him.

“Exactly. This is for the sake of the sexiest couple costume’s contest. Marissa needs you, bro. She needs you to fuck my ass!”

I almost burst out laughing as I say this.

I think we both know that we are telling ourselves a story but Leonard needs this to take the leap.

“Show me your hole.” He commands.

He has not told me that he will do it but I know that I have already won.

Once he gets a good sight, he will not be able to resist my pinkish smooth asshole.

It is shave, clean and prepared, I was getting myself ready to get fucked that night, I had simply not anticipated it would be by the sexiest hunk of the entire campus.

Honestly, as I undress, I am a little self-conscious about my own dripping erection, - I wonder if this could turn Leonard off -, and I am also getting worried about the abnormally large size of his dick.

I have been pounded by big guys before, but this is a whole other level.

In the end though, the excitement triumphs everything.

I want this, I need this… And apparently, so does Leonard.

He spanks my bare ass cheeks. I go on all fours on the floor. I am trembling but I am eager to feel him inside of me.

“Use the lube…” I request, getting a bit concerned.

“Arf… Don’t worry about that…”

Leonard spits on my hole and then, he surprises me as he gets on all fours himself and starts licking me off.

“Hmmm…”

I am stunned!

Leonard Rickman is eating my ass! How the fuck did I get so lucky?!

And he is really going in, - no holding back -, as I feel his tongue searching my insides and bathing in my hole.

He spits again and starts rubbing his fingers against my pucker.

“Damn, bro, your hole is… Jesus Christ… I’m not afraid to say it, your hole looks better than a pussy… You know that I love anal, bro… You must know that…”

“Now I do…” I muttered.

He shoves a finger in my hole. Deep. He does not waste time.

Already, it feels so fucking good but then, he starts rubbing his cock between my two ass cheeks.

“I’m going to drill that ass, bitch… I have to…”

“God… Please, do…”

“You really think my cock is gonna fit… Your hole looks so freaking tight, man… So narrow…”

Apparently, fitting is the theme for this evening.

I am sweating. I feel dizzy.

“There’s only way to find out…” I whisper.

I barely have time to finish my sentence that Leonard pulls his finger from my hole and shoves the tip of his enormous cock instead.

“Let’s find out, then!”

In a grunt, Leonard pushes his cock deeper inside of me.

“Aaaah…. God…”

“Are you good?”

“Please… Please… Keep going!”

He slaps my ass. I am giving him exactly what he wants to hear.

“You’re driving me crazy, bro!”

He gets in deeper and I think, tap against my prostate.

I lose control.

“Hmmmm… Yes… Yes… Fuck me!”

“Oh, fuck yes, I’ll plough your little ass just right… You wanted to make me cum, I’ll breed you all right!”

“Do whatever… Hmmm…”

He starts the back and forth, the rubbing inside my anal cavity is sending me to places.

I think it is going to hurt afterwards, maybe I will not be able to sit for a few days, but trust me when I say that it is worth it anyway.

“Take… My… Cock… Deep… Inside… Your… Guts!”

“Do whatever you want with me… I… I’m yours…”

He grabs my neck and fucks me harder.

My hard dick is bouncing against my stomach. I think I’m cumming but the anal orgasm I am experiencing is so strong that I lose all sense of what is happening.

At some point, I scream so much that Leonard smothers my mouth with his large black hands.

“Shut up, bitch… You’re my cum dumpster, tonight, okay? You want this… You need this!”

I mumble a yes, somehow.

On the corner of my eyes, I see my phone vibrating. Jason is calling me. I am so late at this point.

Who fucking cares?

When I will tell him about it, he will get it. Better, he will be dead-jealous!

Suddenly, something unexpected happens. I feel myself getting lifted up in the air.

Good Lord, the quarterback is so damn strong. Still buried deep in my ass, he carries me and leads me to the bed.

I find myself facing him, my legs spread wide around his chest and, as he is looking at me right in the eyes, he keeps on banging me.

He is going so hard now, his balls are fapping against my ass.

“Beg me to cum, baby… I want you to plead for my load!”

“Yes, please… I want it…”

“What do you want, bitch?”

“I… I want your cum inside of me…”

“Oh yes, is my big rod making you feel good?!”

“So good… So good, please… Breed me…”

“You like when I go balls deep?!”

“Yeeeeeeees…”

He leans over and for a split second, I feel like he is about to kiss me. Ultimately though, he ends-up licking my nipples.

Good enough, they’re very sensitive and I love that.

“You’re fucking great as a cum bag, you know that?”

He can talk dirty to me, he can make me his bitch, I would do anything for that large cock ploughing my ass.

Besides, I know that I am the one secretly holding the power.

That is the biggest misconception about bottoms, most often than not, we are the ones in charge.

The man fucking me is addicted to my hole, or at the very least, he will be.

I can tell, this is a first time but Leonard will come back for more.

“I’m anything you want me to be…. Hmmm… Honey… I need your juice…” I beg him.

He puts his hand back around my neck, - he is choking me without really strangling me -, and he goes even harder with the back and forth while he does not look away from my eyes.

“I’ll fill you up! I’LL FUCKING FILL YOU UP!”

“Please… Ffflease…” I mumbled.

“I’m coming… I… Fuck… Yes… I… I’m comiiiing…”

And there I feel it, the loads being spilled into my wrecked and drenched asshole.

Leonard thrusts his large muscular hips a couple more times, slowly and hard, and he let his cock deflating in my hole for quite a long time afterwards.

Funny to think we were supposedly in a hurry to get the fitting issue fixed…

Only when his cock has turned back to its flaccid taste, he takes it out from my gaping ass.

Naturally, I kneel down again and slurp all the juice dripping from his junks. Delicious.

“You really like that, do you?” He asks, sounding impressed.

I smile at him and I nod yes.

“Straight men are really missing out.” I say, licking the cum coating around my lips.

“Damn right! No girl likes a cock like you do, man!”

I kiss the tip of his dick one last time.

“Still wanna go to your stupid Halloween party?”

“Hell yeah, I have a prize to win!”

I am surprised he is still serious about that, but that is fine. I am too drained to go for round two.

Not now anyway.

All this time, the latex shorts was still hanging right below his ass. I guess it is finally time to dress him up.

I slide the outfit over his big bum and his prominent limp dick.

Truthfully, it turns out that it is not that difficult and the costume suits him perfectly.

Leonard uses a towel to wipe the sweat and various juices from his body, - I might have poured some of my cum on his rock-hard abs at one point -, and he gets ready to leave.

Before he goes, I ask him to sit and I take a picture of the outfit I have just created.

Mainly, I want a memory of that evening.

He graciously poses for my camera, and then, as if nothing has happened, he stands up and get ready to leave.

“Happy Halloween, Dennis!”

It sure is.

I learn a few hours later that Marissa and Leonard effectively won the contest. Good for them.

[THE END]