Training a Precocious Merchant for Her Dreams
The contract period with Sierra passed smoothly. Of course, "smoothly" was strictly from my perspective; for Sierra, it was probably the most grueling time of her life.
Take the third day, for instance—the day I finally claimed her mouth.
"Slurp, *shup*, *ngh*, *ghhh*..."
I spent half the day prying open her tightly closed lips with my cock, thrusting it deep down her throat. To ensure she wouldn't develop an aversion to my member, I smeared cream over it and rubbed it all over her face, which was already messy with pre-cum.
I also made her breathe only through her nose while keeping my cock stuffed in her mouth, or had her rest my shaft on her fully extended tongue, letting her drool and stimulate it using nothing but her tongue. Whenever she resisted, crying out, "Why on earth should I do that!", a single pinch to her trembling nipples would send her into shivers, forcing her to eagerly take it back into her mouth.
"*Suck, slurp*...!"
Near the end, when I offered to reduce her contract by a day if she could make me cum, she knelt on the floor, rested her hands on her thighs, and sucked on my cock with absolute desperation. But Sierra, who had only ever been on the receiving end of my thrusts and had no idea how to blow a man, failed to make me ejaculate even after an hour.
"Ngh... Why..."
Sobbing as she clung to my shaft, she kept her mouth clamped tightly around it, her face contorted in frustration even after I handed down her death sentence: "Time's up." Seeing her look of utter despair as she sucked my cock after her overconfidence cost her an extra day on her contract—it was absolutely exquisite.
I tried to teach her how to kiss as well, but her stubborn refusal to kiss me was so unyielding that I settled for teaching her how to use her tongue in more detail. I often wondered—with her and other women alike—isn't sucking a cock technically more repulsive than a simple kiss? But hey, it was their choice, so who was I to complain?
Since she had become a natural at sucking cock in just a single day, I began to thoroughly explore Sierra's voluptuous body starting on the fourth day. Though she was on the shorter side, stripping her bare revealed a truly magnificent figure hidden beneath her clothes.
"Ngh... Why am I doing this in front of you...!"
Click-clack, click-clack.
After stripping her down to her birthday suit and making her put on high heels, I ordered her to do a model walk. Sierra placed her trembling hands on her hips, having nowhere else to put them, and obeyed. Her plump, well-fleshed thighs jiggled beautifully with every step she took, and her heavy breasts bounced up and down.
After doing a lap around the room, she finished her routine by turning around, grabbing her own buttocks, and thrusting them toward me. The exquisite harmony of her plump pussy and soft, round ass made me want to reach out immediately, but I was the type of man who saved the best dish for last.
Squeeeze.
I laid the naked Sierra down on the bed and squirted some oil I had bought from the Krafton shop onto my hands. Enjoying the slick, viscous texture of the oil, I first placed my hands on Sierra's soft, pillowy breasts.
Squish, squish.
"Ghyahhh...! ♡"
After two days of intense sensitivity training, her breasts had become incredibly sensitive. The moment I kneaded her oiled breasts and pinched her nipples, a loud, echoing moan filled the room.
As I massaged her glistening, oiled breasts and repeatedly flicked her shiny nipples with my fingers, Sierra's pussy began to drench itself in her own juices, slick and wet even without any oil.
Slather, slather...
I thoroughly coated her soft skin with oil, savoring every inch. The merchant's luscious body was delightfully plump, yet lacked even a single trace of unsightly fat. With my fully erect cock on display, I climbed on top of her and slowly massaged the oil into her skin.
Gulp...
Lying as meekly as a fish on a cutting board, Sierra seemed to enjoy my hands sliding over her skin, but her eyes were locked onto my cock. Having tasted it on the third day, she was trying to act indifferent, but it was clear she couldn't stop thinking about it.
"You really have a lewd body gifted by the gods, Lady Sierra."
Squeeze, squeeze.
As I kneaded her slick, oiled thighs and teased her, Sierra's face flushed crimson, and she spat back defensively.
"Who has a lewd body...?! I've never met anyone as vulgar and depraved as you in my entire life!"
Wiggle, wiggle.
Despite her sharp words, her pussy was already drenched in the juices she had squirted while her nipples were being teased. I placed my hand over her wet mound, deliberately taking my time to torment her, until she finally surrendered.
"Fine, just... hurry up and put some there too...!"
Always trying to have the last word, aren't we? Still, a feisty woman like Sierra was always a welcome challenge. A little resistance only made the conquest that much sweeter.
I grabbed her mound, parting and closing her thighs as I thoroughly massaged oil into her labia and mons pubis. Admiring her engorged clitoris, I stared intently at her opening, which immediately responded by weeping another gush of sweet nectar.
"Haaah..."
Embarrassed by my intense gaze on her most private area, Sierra let out a soft sigh and tried to close her legs. I blocked her by wedging my knee between her thighs, then stroked her pussy with my oil-slicked hand.
Squelch, squelch.
A wet, squelching sound echoed through the room, fueled by the oil and her own juices. Her pussy, which had been leaking just from being watched, began to overflow now that my hand was in play. While caressing her soaking wet slit, I pressed my fingernail firmly against her swollen, throbbing clitoris.
"Ghyahhh!"
With a violent jolt, Sierra arched her back off the bed, forming a bridge. Her oil-slicked body tensed up as she squirted a stream of fluid, her hips trembling before she collapsed back onto the mattress.
"My, my... aren't we sensitive?"
"Hah, ah... no more..."
Having reached a massive climax from just a simple pinch of my fingernail, Sierra shook her head frantically, begging me to stop, clearly shocked by her own sensitivity. Having found her sweet spot for the day, I squirted more oil and reached back down to her groin.
Despite the inn's excellent soundproofing, Sierra screamed so loudly during her clitoral and vaginal training that the innkeeper gave me a warning when we checked out. I always knew she had a strong voice, but she ended up completely hoarse the next day. At her tearful plea, I decided to give her a day of rest.
On the fateful fifth day, when I showed up with an enema kit and an assortment of dildos, Sierra pointed a finger at me and unleashed a torrent of curses.
"Did you think I was joking when I called you vulgar?! How dare you bring such things in front of me?!"
"I will absolutely not allow this! I never agreed to anything like this!!!"
"I am never letting you use that filthy hole, so get the hell away from me!!!"
She hadn't complained at all when we discussed it beforehand, but now she was throwing a fit. I tried to reason with her calmly, but her resistance was relentless. In the end, I had to contact Tsuruka and summon Undine before I could finally begin her anal training.
"No pussy, no ass... then which of your holes am I supposed to enjoy, Lady Sierra?"
"Mmph!!! Mmmph!!!"
Gagged and drooling, Sierra thrashed wildly. Even though I had explained everything beforehand, she still resisted, and I forced it upon her anyway. Perhaps the contract deemed it a draw, as there was no change to the remaining days.
I pinned down the wildly thrashing Sierra and asked Undine to assist with the enema. After soothing and sending back a whining Undine—who had burst into tears, complaining, "I'm working so hard for Master Casano, but what is this?!"—I was finally able to resume my conversation with Sierra.
"No! Absolutely not! Anything but this!"
I cornered Sierra against the wall as she crossed her arms in an 'X', resisting to the bitter end. Trapped in my embrace, with her upper body pinned, she still kept her chin up and refused.
"Then can I take your pussy instead?"
"That's...!"
Sierra gritted her teeth, her eyes darting around. Her virginity was her ultimate commodity as a female merchant—that seemed to be her golden rule—but the thought of anal sex was so far out of the question that she actually hesitated.
I swirled the Healing Water I had received from Undine in my hand and spoke to her.
"You know, there is a way to restore your hymen..."
Having concluded through my conversation with Undine that it was entirely possible, I revealed my card without hesitation. Sierra swallowed hard as she stared at the sloshing Healing Water. Her trembling eyes darted between the water and her own body, until she finally let out a defeated sigh.
"My backside... do you really have to touch it...?"
She asked as if pleading for me to reconsider, but I was firm.
"Stop complaining and spread your cheeks."
Gritting her teeth, Sierra turned around and parted her own buttocks, which were already slick with the oil I had applied earlier. Her tightly puckered anus was trembling.
I couldn't help but chuckle at Sierra's desperate attempt to protect her virginity. We still had eight days left. Yet, her training had already progressed to her breasts, mouth, and clitoris. I had already thoroughly fingered her pussy, but that was far from enough.
"You chose this yourself, remember?"
When I asked if she wouldn't regret it, Sierra bit her lip hard and silently pushed her rear toward me. Knowing how exceptionally sensitive her body was, I had a feeling that once her backside was thoroughly broken in, she would eventually beg me to take her front.
Squeeeze.
I squirted lube onto the smallest dildo I had brought. With her face buried in the bed, she wiggled her hips toward me. I deliberately made heavy footsteps as I approached her.
Twitch, twitch!
Though her face was hidden, her plump, protruding buttocks and twitching anus made her nervousness painfully obvious. After lightly tracing her tightly closed slit with the dildo, I slowly pressed the toy against her anus and pushed.
"Heeek...!"
At the cold sensation of the lube and the foreign intrusion, Sierra's anus clamped shut, refusing to yield even a millimeter. I gently stroked her lower abdomen with my right hand, kneading her soft flesh. While massaging the area over her womb, I rubbed my rock-hard cock against her tightly closed pussy.
"You can't put it in...!!!"
Terrified that I might actually penetrate her, she pleaded frantically. I patted her stomach reassuringly and slowly pushed the dildo further in.
Schlip.
"Haaah... It's really inside..."
Grip.
Her hips trembled as she gripped the bedsheets. I continued to rub my cock against her pussy while gently patting her shaking buttocks. Keeping up a steady, soothing rhythm, my left hand slowly pushed the dildo deeper.
Squish, squish.
As I coaxed her and pushed slowly, Sierra's stubborn anus gradually began to welcome the dildo. Marveling at her tight passage's capacity to adapt, I slowly began to pump my hand.
Squelch, squelch, squelch.
Even though it was a thin dildo, Sierra was already highly responsive. Her hips trembled, and her pussy twitched open and shut. Admiring the fierce squeeze of her anus, I pushed the dildo all the way in, gave her butt a playful slap, and pulled it out in one swift motion.
"Haaah...! ♡"
Squirt!
The sudden extraction caused a torrent of her juices to splash onto the floor. Shaking uncontrollably but refusing to let go of the bedsheets, Sierra buried her face in the mattress and let out a whimpering, animalistic cry.
"Ngh, ah... what is this..."
"Shall we try fingers instead of toys now?"
Schlip.
"Mmmgh... ♡"
When I pressed my heavily lubed middle finger against her twitching anus, it greedily sucked it in. Even with just one knuckle inside, the grip was so tight it felt like it would snap my finger. Gritting my teeth, I slowly pushed deeper and swirled my finger around to loosen her up.
"Haaah... ah, no... not my butt..."
In the end, Sierra's choice was proven right. Her blessed, lewd body adapted incredibly fast; within twelve hours, her anus had adjusted to every dildo I brought, as well as my fingers. Squeezing with incredible force, her tight rear pushed out the last dildo with a wet slide, pulsing open and shut as if boasting of its newly unlocked potential.
"Haaah... Haaah..."
"Impressive."
"Ngh... to think it would stretch open so shamelessly..."
Pucker.
Once the stimulation stopped, her anus, now loose enough to accommodate my cock, slowly began to contract. Tracing her puckered, flower-like opening with my finger, I flashed Sierra a satisfied smile.
"To adapt this much in just one day... you really have a spectacular body, Lady Sierra."
"Who... who would be happy about that..."
Panting heavily with her face buried in the bed, Sierra trembled as I patted her buttocks and pressed my cock against her. Feeling the blunt tip pressing against her anus, she shook her head frantically, trying to stop me.
Squish, squish...
A vice-like grip clamped around my shaft. Having barely managed to slip the head inside, I felt her anus squeezing as if trying to choke my cock, but I gritted my teeth and pushed my hips forward.
Squelch, squelch.
Every time I made some progress, Sierra's thrashing forced me to pull back slightly. And when she calmed down and I pushed back in, the sheer, crushing tightness made me fear my cock might actually snap, forcing me to retreat again.
In the end, the grand anal training concluded with thoroughly stretching her with fingers and toys. Though she had resisted with murderous fury at first, an hour before we finished, she was grabbing my hair and squirting as she reached a magnificent climax.
"Uwahhh... I don't care anymore... to cum from such a vulgar hole, sob...!"
She clung to me, weeping loudly as if filled with regret, but since she had shown the most intense pleasure of the past few days during the act, I reasonably assumed she was just acting out of sheer embarrassment.
On the sixth day, Sierra lay on the bed, her entire body glistening with oil. She spread her legs with a tense expression and looked up at me. Feeling a surge of anticipation myself, I looked down at her and slowly brought my throbbing cock to her anus.
After thoroughly warming her up with foreplay, Sierra's body melted into a soft, pliant state. Sensing the perfect opportunity, I climbed on top of her. This was the moment right before taking the final step.
Schlip...
Sensing the impending intrusion, her anus twitched. I pressed the head of my cock against it. Feeling the incredible, vacuum-like suction pulling me in, I gritted my teeth and thrust my hips forward.
Squish... slide...
"Hah... ah...?"
The moment I managed to slip my cock into her tight rear, Sierra let out a breath, her face showing a hint of confusion as she felt the thick shaft slowly filling her.
"It feels... surprisingly comfortable...?"
Though her face contorted slightly from the pressure, she managed to take it all in. She looked up at me, her expression suggesting it wasn't as bad as she had feared. Meanwhile, feeling her tight rear swallowing half my length, my hips trembled. The sheer, mind-blowing pleasure almost made my knees buckle.
Tight, tight.
"Heh... I've never seen you make... such a pathetic face before..."
Letting out a soft groan, Sierra seemed to find the sensation bearable enough to start teasing me. I endured the overwhelming pleasure, slowly pushing deeper. Sierra's twitching legs wrapped around my waist.
"Clinging to me with such a pathetic look... I suppose you have a cute side too... Oh...?"
The moment I buried my cock to the hilt, I seized the opportunity and pulled out in one swift motion. The head of my cock scraped along her inner walls as it slid out, barely remaining inside her anus.
"Oh, ah... h-haaah...! ♡"
The extreme pleasure of having her inner walls scraped sent Sierra's hips arching off the bed. Her smug eyes rolled back, and the mouth that had just been mocking me fell open, her tongue lolling out as drool began to spill.
Overwhelmed by the unbearable ecstasy, Sierra's body collapsed onto the bed. Without stopping, I began to slowly pump in and out.
Squish, squish, slide.
Her rear was as tight as ever, but having grown somewhat accustomed to it, I closed my eyes and pushed through. Sierra, on the other hand, was completely swept away by the unstoppable wave of pleasure. Lying limp like a sex doll, her hips bucked against mine as she let out fragmented, broken moans like a skipping record.
"Ngh, ah, hah... h-haaah...!"
As her anus began to accommodate my cock more smoothly, I snapped my hips and drove myself all the way in. The impact made Sierra, whose tongue had been lolling out limply, throw her head back. She wrapped her arms and legs tightly around me, clinging to my body.
Between the crushing squeeze on my shaft and the intense friction of my cock scraping her insides, we both reached our limits. Holding Sierra—who was now as limp as a broken doll—tightly in my arms, I thrust deep and ejaculated.
Even in her exhausted state, Sierra held onto me tightly at the end. Sharing our warmth, we marked our monumental first anal climax.
Pop! Squirt, squirt.
"Ngh...! ♡"
As I slowly pulled my cock out, her anus let out a wet popping sound before gradually contracting. Even so, a generous amount of semen began to leak from her stretched opening. Watching the semen ooze out, I pressed down firmly on her lower abdomen.
"Hyaaa...! ♡"
Squirt!
At the firm pressure on her stomach, a stream of fluid squirted from her pussy, while the semen gushed out of her stretched anus. Wiping away her dried tears with the back of her hand, Sierra let out a dazed, breathless giggle.
Now that she had tasted such intense pleasure, the next step would be a breeze. Watching Sierra's twitching pussy, I licked my dry lips.