Suck her dry, you trained for it

You get on all fours and move closer to her meat pole, lazily swinging in the air, until her glistening head is but an inch from your face.

"You know... I think i could get used to this"

She tilts her head a little, a puzzled smile crossing her face, but stays quiet, resting again on the plush pillows.

Here we go...

You welcome her smooth head in your mouth, sucking on it gently as you lay your hands on the shaft, rubbing her length gingerly, one hand after the other.

By a rough estimate, her length at full mast is twelve inches, I barely managed to get four the last time...

Let's aim for six and see what happens

You begin bobbing your head up and down, pushing the underside of her cock up with your tongue to get a little breathing room. Every time you go down, you take a little more of her impressive cock inside you, and when her head punches your uvula, you suppress the gag reflex, counting down from a thousand;

Nine hundred and ninenty nine,

Nine hundred and ninety eight,

Nine hundred and ninety seven...

You got this Liam

Her pulsing pleasure rod pushes through your previous limit, and you feel your airflow get severed as her girth effectively plugs your throat shut. You withdraw, take a breath, and push it deeper again.

"Hmm, your virgin throat feels so good, honey"

You dive on her cock again and again, clumsily at first, eventually managing to turn it into a fluid motion. After a while your throat starts to feel sore, burning as her rock hard dick slides in and out; you reach a point where you just can't take it any deeper, and touching your neck you feel her bulging member, stretching your pharynx thin at the height of your adam's apple.

My god, there is still so much cock... I just can't...

You grunt as you pull it out of you, slobbering her knob to catch a breath, massaging her shaft; you hope that's enough to make her happy

Esmeralda is unusually quiet, she barely let out a couple pleasured moans as you fucked up your throat for her

Why the hell does this irks me so much?

"Don't be sad, cutie. You were good, really! But I had a long day too, you know..."

she starts to count on her fingers

"I scrambled Janice's pussy after breakfast, and Mei put on a pair of really skinny pants, her thick ass was just begging to be plowed, so i bent her on the table and fucked her senseless, twice. After lunch i started thinking about you, so i jacked off, and Mei was there with me, so of course she got hard, and we made a bet on who could last longer, she obviously lost and i got to stick it in her juicy butthole again... Oh, and I cranked one off while you two were getting to know each other. So i jizzed a total of... Six times today. My dick is a little numb now, if you want to make me cum, you'll have to put in a little more effort..."

I'm fucking spent girl, my throat is on fire. What more can i do to fucking please you?!

She makes an O with the thumb and index, fingering it with the other hand

Oh...

Hell no

I just got used to giving head, you can't be fuckin serious

"You DO want to make me cum, don't you sweetie? You want to hear me moan, squirting my love juice all over your naked body.... If you didn't, you would have walked away right after dinner, right?"

Wait, was that an option?

Esmeralda kneels in front of you, stroking her cock

"Turn around cutie, don't make me beg"

"WAIT!"

You can barely recognize your own voice, rugged and raspy

"I could barely take half of your cock in my -groan- throat, what makes you think my ass could do any better?"

Esmeralda laughs in your face, as her unoccupied hand, sliding down your side, rests on your buttcheek, groping it tenderly.

"I know I'm too big to go balls deep at the first time, don't worry"

She gets closer, and whispers, nibbling your earlobe: " i just want to pop you cherry tonight, and i'll be gentle, pinky promise"

The last time i heard those words it didn't end well;

"Aren't you a little curious? You boys do have the cum button right up the ass, after all..."

They say you shouldn't knock something off until you try it at least once...

Fuck it

My future self is going to hate me for this though.

"O-okay, but... just the tip"

Esmeralda smirks

"I won't promise you that, sweetie. I have needs too"

Off to a bad start already...

You gingerly turn around, knees bent, resting your weight on your elbows.

At the foot of the bed, just like in your room, there's a window: gazing in the dark reflection of the glass, you see Esmeralda sucking on her middle finger.

She puts both hands on your asscheeks, spreading them apart

"Hmm, what an enticing sight... I love to be the first to pop a boy's virgin ass"

You feel her wet finger testing your hole; she slowly pushes it in, fingering you first with one, then two, eventually three fingers.

You grit your teeth

Okay, this is... weird, but not as painful as i imagined

"Good boy, just like that"

She takes out the fingers, and you feel the warm head of her dick kissing your anus

"Take deep breaths with your mouth, and don't clench your asshole, it'll only hurt you more"

Esmeralda squeezes her shaft, moving from the base to the tip, a warm blob of cum wetting the entrance of your man-cave

Guess thats all the lube I'm getting tonight

"I love you sweetie"

"Love... you too-nngh-"

As she penetrates inside you, your anal rings stretches around the invader, burning like hell

Both your moans fill the room; Hers of pleasure, yours of pain.

"So... Tight... Hmmm"

Shit

Nope

I bent, I tried, I fucking hate it

Too late to run now

Fuck you, past me; you're a cunt

Esmeralda grabs your hips firmly and pulls you toward her.

"Your ass feel so good, cutie."

With a sharp "plop" her unwieldy head pops inside your ass, she grips the middle of her shaft and begins to rotate it, slowly but surely pushing forward, as it spits a squirt of precum, coating your insides.

You are painfully aware of every movement, as her tip brushes against the walls of your rectum. At this point, you're basically whimpering, tears welling in your eyes.

Fuck... How much time has passed? She's barely two inch deep, maybe less...

Her gargantuan cock has made enough of a headway inside your butt that Esmeralda has started to lightly thrust your hips back and forth, they're barely love taps, but it sends shivers up your spine.

To your surprise, your pecker is so hard that every time she stabs her dick deeper in you, it lets out a dribble of semen.

"Leaking already? Lucky you, I'm barely getting started"

Sigh...

After what feels like an eternity, she stops pushing forward, and begins moving her hips back and forth at a faster rate; she can't be deeper than four or five inches, so she kept to her word, in a way.

Still hurts like a motherfucker though...

Time loses its meaning, her rhythmic thrusts getting faster and faster are the only way of keeping track of it, like a meaty, throbbing, granpa clock stuck inside your butthole.

"Do you like it, cutie? Do you like having my big cock inside your tight, supple ass?" She asks, caressing your back

"I -nhg- really -oow- don't"

"Once we loose your ass a bit you'll love it cutie... You won't stop asking me to fuck your nice round butt" she punctuates the statement by slapping your butt cheek

Fuuuck... How long does this agony has to last? It hurts so much I can't think straight

Esmeralda almost seems to read your mind. She picks up the pace, ramming her dick in and out at top speed, her moaning almost covering your cries of pain

"Hmmm, fuck i could do this all night"

Oh please no...

"C-ahaa- cum..."

"Hm?"

"Cum n-uha-ow... plea-ahaa-please"

"Hear that, cock fairy? Let's grant my cutie his wish"

She jackhammers your sore ass for a good five minutes before finally filling your cavity with a huge load of thick, hot spunk, moaning loudly as you scream in pain.

She bends down and hugs you, breathing heavily; her cock turning soft inside you, cum leaking out of your ravaged hole

"Up for round two cutie?"

You stiffen all of a sudden, cold sweat on your brow.

"Ahahah, i'm just joking, no need to get all riled up..."

"That... That was painful..."

She drags you back, laying on her side, spooning you while her limp dick is still inside your butthole, even when soft it still stretches your burning anal ring.

"You did good, next time you'll enjoy it more... I can leave it in, so we can try again first thing tomorrow..."

"Please... just... take it out... it hurts so much"

She gingerly slides her cock out, giggling; and the still warm semen inside your rectum oozes out.

"Oh... My poor Liam is hurt... My big bad dick hurt him so bad" she mocks, sliding one long, slender leg over yours, pressing her flaccid member against your buttcrack, squeezing her firm tits on your back

"You want to get even, stick it in my bum?"

Is she still mocking me?

"For... for real?"

"Sure, seems fair... You can go balls deep"

She turn to the other side, sticking out her perfect butt.

Fuck... Is this real? Is this really happening?

As you get in position behind her, dick still hard from earlier, you tentatively poke her butthole.

"Hmm, don't tease me like that, just do it"

You push your prick inside her, her anus offering very little resistance, and unlike her, after five inches you're already at the end of your rope, so to speak.

Damn, this feels fantastic!

Its almost worth the agony of getting dicked down like that,

Almost...

beginning to pump inside her, you reach for her breast and grope it.

She pushes back everytime you thrust forward, and clenches her rim around your dick when it's almost out, like she doesn't want to let you go.

"feels good honey?"

"Like heaven... made flesh" you pant, voice still rough.

"That good uh?"

"I... I... Oh God"

You unceremoniously come inside her warm hole, panting heavily. You barely lasted ten minutes inside her, but those were the best ten minutes of your life.

Esmeralda turns back to you, offering a sweet smile

"Feel better?"

"I... I fucking love you dammit"

First rule of the dude club: shut up after you nut

Second rule of the dude club: shut that fucking trap after you nut, goddamit

She pulls you close, stamping a tender kiss on your lips

Thats how you fall asleep, her body wrapped around yours, buck naked on a blanket damp with jizz.

Could be worse