DISCLAIMER: I don't own any of the characters.

(Jack x Elsa) Late in the afternoon, Jack goes on his first date with Elsa at the local ice hockey arena after closing, leading to a steamy intercourse out on the ice. That's when Elsa gives him her offer to sleep with numerous woman that she picks for him for the entire month.

CONTENT WARNING: Blowjob, vaginal sex

DAY 1: Elsa Arendelle

Downtown Suburbs
February 1, 2020
Saturday
8:03 PM

Sitting quietly in his room, Jack doodled away in his notebook absent-mindedly, just one of the things that helps relax his mind and give him something to do than just lazing around in his room. His drawings were mostly spot on and he etched very creatively. It was a mild juxtaposition to painting a picture of the ocean or a mountain in Colorado, you take your pick. There was no denying that his mind was spiraling at the moment. After so many months of sitting back, trying to mow through his insecurities and get that chance before it was gone forever. It was a window that would not stay open for long. But today was going to be the day. Today he was going on his first real date with the school's most alluring alpha female, Elsa Arendelle. It was a dream come true.

He could remember it like it was yesterday when he first laid eyes on her, basking in her beauty. She was very well-known around the entire school, the faculty, social media, she was practically a celebrity. She had so many friends, so much praise and dozens of horny men attempting to woo her and get into her pants. But Elsa was your average Mary Sue, but she was no prude either. Rumor has it that she banged Hans Westergaard from the ninth grade. He had her wrapped around his finger and she was like putty in her hands. She only gave subtle details to this proclaimed encounter, but not one person could have predicted her to have fallen for the whims and wiles of Hans of all people. The guy was a real prick, an obnoxious skirt-chasing sociopath with no differentiation of right from wrong. In fact, one time he and Snotlout locked Jack in his closet and he was stuck there until Hiccup helped him out. But despite such an encounter, she and Hans were no power couple or any kind of couple for that matter as far as she was concerned. Hans was probably using her for his lecherous needs and wanted something to brag about to his friends as if he had won first place in the Olympics.

Currently, Jack's mother was working late in the office and his father was passed out on the couch in front of the TV after a long morning shift in the office. His sister, Emma, was having a sleepover with some friends at Riley's house, so it was just them guys. He also has an older brother named Michael who is in college right now, studying history and geometry. They usually keep in touch via text messaging and FaceTime. But it mostly takes forever for Michael to respond to his brother's messages, either he's too busy studying, partying at the frat house or just hanging out with his roommates for all Jack knew. While drawing, he was texting with Hiccup who was at the arcade with the rest of the guys.

Hiccup: You sure you got this?

Jack: Of course.

Hiccup: Ok. Just don't blow it or else. ANd remember to use

Jack: STFU

Hiccup: 😂 😂 He heh. Rotf

Jack: Anyway, I should be ready to go soon. I'll see where the road takes me.

Hiccup: Hopefully inside Elsa. 😏

At this point, Jack was done with the foolishness of the conversation as he placed the phone and readjusted his desk lamp to better focus on the delicate pencil strokes on his notebook paper. He wants it to be just right. And he messes up, he'll just have to erase and start over. Just when everything was falling into place, his phone rang. Breathing a sigh, he looked and was surprised to see the caller ID, it was Elsa calling him right now. Gulping and clearing his throat, he slowly accepted the call, pressed the phone to his ear and let out a fragile, "Hello?"

"Hey, Jack. It's me." came Elsa's voice on the other end. "So listen I'm ready for our little outing this afternoon. Meet me at the river by the bridge in one hour. Don't be late, okay?"

"Okay, see you then." Jack answered.

"Excellent. Bye." Then she hung up completely.

Right away, Jack bookmarked his notebook with a mental note to return to it soon and shot up from his chair to get ready. He grabbed his coat, beanie and gloves because it was going to be chilly out at this hour. Though he made sure to head downstairs slowly since his father was still napping on the couch with the television left on, static and all. The man needed his rest after working so hard all day. Any amount of noise would startle him awake. Step by step with the stealth of a mouse, Jack tiptoed over to the front door and left the house, closing the door behind him with his father thankfully not noticing a thing. And just as he expected, it was as freezing out there than it was akin to Antarctica with thick layers of snow all around. So Jack journeyed off through the neighborhood, listening to his boot-clad feet crunch in the snow-covered sidewalk. Jack kept walking down the block until he found the pathway between two houses that led to a shortcut which cut through the woods, connecting the suburbs to the streets of town.

Meanwhile, Elsa sat on the bench with a cup of caffè mocha in her mittened hand while facing the frozen river which had a nice view of the skyscrapers on the other side. Said bench she was on sat near the large cobblestone bridge which had a flight of stairs on both sides and a walking path that stretched underneath it. Just a couple meters behind her was a copper statue of an American war soldier. And as she idly sat waiting for Jack to arrive, she hummed a soft, relaxing tune to herself, allowing the cool vapors to flow from her mouth.

"~ Into the unknown. In the unknown. Into the unknown! ~"

After what seemed like minutes, Elsa finally heard the familiar sound of feet crunching in the snow behind her approaching closer and closer. Elsa intuitively guessed who it was and didn't need to turn her head around.

"Hey." Jack greeted her as he sat down beside her.

"Hey." Elsa greeted back with a smile towards him.

"So you ready?" asked Jack.

"Of course." nodded Elsa with inconspicuous eagerness. She downed the last gulp of her coffee and tossed it in the trash can beside her. "So do you know where this ice rink is?"

"It's just down the road from here. Only a mile and a half." answered Jack as he pointed in the direction on the right of them. Elsa then stood up, already ready to have some fun with her friend, and offered her hand to him.

"Shall we, then?"

Jack smiled and accepted her hand and allowed her to help him up, while at the same time, feeling another blush paint his face from actually holding his crush's hand. It was just getting better and better as he was already beginning to suspect that Elsa was intentionally giving him not-so-subtle hints that she digged him. He allowed Elsa to lead the way when she claimed to have been there from time to time in the past. Jack knew how to get there, too, but perhaps he wanted her to walk in front of him just so he could have a few of her from behind, especially her gorgeous round derriere in those tight jeans, which truly accented her thick curves. Unknown to him, however, Elsa already knew what was on his mind as they ventured to their destination and held a mysteriously smirk on her face. If only Jack knew what she had in mind for him. And she had a feeling it will help change his life forever for the absolute better.

It took a while, but they finally made it to the place they wanted to be. It was the local ice skating arena where hockey teams have played before. Memories flooded Jack's mind when he remembered going with Emma and Jamie to attend Riley's first hockey game. She scored twenty points for her team and it helped them win the game. Unfortunately, Jack realized that the place was deserted. No cars in the parking lot, all the lights were off and it only meant one thing.

"Aw, damn it. The place is closed." Jack groaned in exasperation and utter disappointment, feeling let down by this turn-of-events as he was really hoping to learn skating.

"Not on my watch." Elsa objected with a sinister grin on her face as she carried on towards the building. "Come on."

"Elsa, forget it. We're too late. It's not-" Jack had to go keep up with her as the girl walked even faster like a child wanting to get into the candy store. "Elsa, wait! Wait up!"

"We're still getting in." declared Elsa mischievously to him with determination.

"Elsa, they're not open. The place is locked up tight." Jack attempted to gently dissuade her from the situation and hopefully steer her towards a walk in the park instead. However, the snow-haired girl had other ideas.

"You wanna bet?" asked Elsa rhetorically with a disturbing Grinch smile, which began to put Jack on edge as the realization struck him like a runaway car.

"Are you suggesting we….break in?" asked Jack with shock.

"Oh, come on." Elsa begged. "I wouldn't call it breaking in. We just sneak inside, have our fun and get out. Don't worry, we won't be hurting anything."

"That's what I'm afraid of."

"Hey, you're not gonna flake on me now, are you?" She asked with a hand on her hips as if to guilt-trip him into play along with her plan. Once again, it took forever for Jack to ask her out and this was his chance to prove himself to her and he didn't want her to think of him as some kind of loser. And furthermore, it was his idea to come here in the first place. He darted his eyes around until he noticed a window that was serendipitously left slightly ajar.

"What about there?" He asked, gesturing towards the open window.

"Good thinking, Frosty." Elsa joked, giving him a tap on the shoulder before they marched over.

It was only five inches above their heads. Elsa volunteered on going first. She had Jack lift her up to reach it. In the process of elevating her off the ground, Jack got another, more up-close view of her butt in his face before Elsa grabbed onto the window and pulled herself in. After some struggle, Elsa helped Jack climb inside as well and before they both knew it, they were inside the arena. It was, naturally, dark as could be in there. They pulled out their phones to use as flashlights to navigate their way in the pitch black darkness. They managed to find one of the ice rinks inside. Scoping around with their phones as their only light source, Elsa finally found some light switches to the entire room. Flipping them on, it bathed the entire rink with light.

"Well, this is amazing." commented Elsa as she removed her coat. "Take your coat off, it's not that cold in here."

"Okay." He agreed, removing his winter apparel.

It didn't take long for Elsa to find some ice skates. She put them on and began to skate onto the ice with Jack watching her. Elsa was just a natural. She's been skating on ice since she was a little girl. She and her sister. It was like the one thing she was good at. Skating and dancing around using graceful moves that would make Michelle Kwan jealous, she curved and spun around like a majestic ballerina princess, all the while Jack enjoyed it from the middle row on the bleachers. Reaching the center, she finishes her performance with a twirl at the center before landing on the foot, striking a pose. Jack applauded her from above and she gave an exaggerated bow. Elsa then invited Jack to join her out on the ice. Jack was hesitant at first, but it took some….persuasion.

Getting his skates on, Jack cautiously placed one foot on the ice with Elsa by his side to guide him along the way. Once he was on the ice, he immediately slipped, but thankfully Elsa was there to hold onto him. To be honest, Jack was having a tough time skating on ice as it required perfect balance. Elsa held onto him tightly as they glided across the rink together, helping him keep it steady. After some practice, he was beginning to get the hang of it. But Elsa remained, in case he still slipped. Jack was really starting to have fun with this experience. Here he was, learning out to skate with his crush. This was starting to be the best day of his life. The two were enjoying each other's company, skating together in each other's arms. Afterwards, the two sat on the bleachers at the very top row, relishing the night's events.

"Can I tell you something?" asked Elsa, breaking the ice (no pun intended).

"Yeah, what?" asked Jack.

"You remember Hans Westergaard?" Elsa began with a serious tone, turning her head toward him.

"Yes, why?"

"Well, let's just say he and I never really had sex." confessed Elsa. However, Jack was not at all surprised by this since she didn't seem like the kind of person to end up with a planet-sized douchebag like him. Her sister, maybe. But certainly not Elsa.

"Are you serious?" He asked her.

"Uh-huh. We were never even together to begin with. Though, my sister had a crush on him once." Elsa explained, shrugging her shoulders. "Until she realized what a pompous asshole he really is."

"What a shock." sighed Jack. "Did you know he stuffed me in my locker once?"

"No. He actually did that?" gapped Elsa with an appalled expression.

"Yeah. I was getting my text book out of my locker, then all of the sudden, he pushes me inside and locks me in. I was stuck in there for like four hours before Hiccup came to help me out."

"Jackass." grumbled Elsa angrily. "Well, thank god for Hiccup, right?"

"I'll say." Jack stated in agreement. "We've had each other's backs as long as I can remember."

Elsa nodded as the two sat there when a still pause settled in before Elsa decided to get to the real topic and ask him something much more personal.

"How long have you had a crush on me?"

Jack widened his eyes as if he had just witnessed a murder, seriously taken aback by Elsa's sudden frankness on a sensitive matter. But nevertheless, he had to provide her with an answer.

"Very…..very long time. Why do you ask?" He stammered.

"I think it's pretty obvious." Elsa reminded him, completely turning to face him. "Why else would you ask me out here tonight? I mean, it's written all over your face. And don't think I haven't noticed you sneaking peeks at me recently."

"W-What? I mean, I…" Elsa only giggled at his hilarious reaction; stuttering his words in his quest for a feasible explanation to her question before standing up and walking downward off the bleachers.

"Where are you going?" asked Jack.

"Back on the ice." Elsa called back matter-of-factly before she stepped foot on the rink without her skates.

"But you're not wearing your skates." He reminded her with concern that she may slip and hurt herself.

"I know." Was what she could only say as she maneuvered out onto the ice, surprisingly not slipping or falling. Perhaps the ice wasn't very slick. "Relax, it's not that slippery. Come on out. Just be careful, though."

"Um, okay. If you say so."

Jack reluctantly decided to take her advice as he gently moved onto the ice in his sock feet. Strangely enough, he really didn't slip as easily. The entire surface felt pretty sturdy and nonskid at best with Jack now feeling more confident as he moved across the ice toward Elsa at the center of the rink. Elsa smiled that he was able to trust her enough to not chicken out like a pussy and man up to confront his fears. Unfortunately, the moment was short-lived as Jack suddenly slipped and lost his footing, starting to fall backwards. Elsa grabbed onto him to keep him in balance, but ended up being pulled down as Jack fell flat on his back on the ice with Elsa landing right on top of him. And as they regained their bearings, they noticed that their faces were inches close to each other.

They both giggled at this predicament, both red in the face before Elsa realized something. Jack was needing something soft and squishy and looked gobsmacked when he saw that he was holding Elsa's breast. While embarrassed to death, Elsa, on the other hand, was actually flattered. Instead of lifting herself up or giving him a slap to the face for such an albeit accidental perverted move, she leaned forward and connected his lips with her own. At this point, Jack's brain went haywire, his heartbeat going off the charts and his hormones exploding with fire. For all he knew, he was now in heaven where it was just her and him and nobody to disturb them. Jack snapped out of his bewildered state as she slowly accepted the kiss and the two moaned as Jack snaked his arms around her waist, holding her close while Elsa had her arms around his head, delving even deeper in the kiss, both their tongues battling for dominance and individual superiority over the other. Nothing to interrupt this moment. The two wanted to savor it as much as they could.

Elsa smirked and moaned with arousal into his lips once she felt his hand grope her buttocks, needing it gently as if it were made of dough. After what felt like an hour, the two broke apart for her and Elsa stared down at him with a seductive grin before she lifted herself up and felt a familiar throbbing tightness poking against her rear. She had him right where she wanted him. Grabbing the end of her shirt, she slowly lifted it up and discarded it immediately, revealing a pair of D-cup breasts in a dark blue laced bra. Jack could only stare as his face heated up, getting a gander at that smooth, curvaceous, pale and flawless skin of hers just begging to be felt.

"What are ya waiting for, tiger?" asked Elsa with a beckoning smirk.

Jack didn't need to be asked twice as his hands shot up to cop a feel of Elsa's boobs for the first time and, god, it was like no other feeling in the entire world. Nothing could compare this experience with anything else. Elsa moaned sensually as his hands did their work, throwing her head back as her whole body heated up as well, the feeling her breasts being grabbed sending electrical currents up and down from her brain to her beating heart. A sense of euphoric ecstasy was in order. Now it's time to get serious. As Elsa stood up briefly to unzip her pants and remove them, she ordered Jack to remove his own shirt and unzip his fly. Once Elsa was clad in only her undergarments leaving little to the imagination, she slowly slipped her bra and panties to unveil her round boobs and moist pussy to the world and tossed them aside.

She nestled back down to fish something out of Jack's pants and found what she was looking for. There it was before her very eyes; a 12-inch throbbing member that had her licking her lips as she bent down and licked his rod up and down teasingly, causing him to twitch and convulse as she did so. An expected response. After tasting it a few more times, Elsa finally shoved the entire thing in her mouth, moaning as she gave Jack the ultimate blowjob of his life. Jack moaned, too, his hormones sticking dangerously to volcanic-style levels. Elsa bobbed her head up and up over and over, lubing his little friend like a pro. Then she removed it from her mouth before he could get there and licked her lips, smirking at him. Then she lifted herself up and carefully dangled her pussy right over his dick, aligning perfectly in a straight line and then she slowly lowered down, gently sliding his member deep inside of her.

This was now the best experience ever. Both of them held onto each other for support as Elsa slid his member in and out of her. But she needed to keep up if they were both going to reach the finish line. Elsa's moan turned into yelps and into sexually screams as she sped up the process, accelerating a bit faster and faster. Jack held onto her waist like it was a lifeline as his lust-wracked brain controlled his every move with his penis penetrating her snatch. Faster they got, the hotter their bodies got and the closer they were to the climax. By now, Elsa was moved even faster as her screams got even louder since she felt him getting real close and she was, as well. Finally, the train struck. They both hollared out as they both orgasmed together, twitching from the release. Elsa panted heavily, drenched in sweat from the encounter and allowing the fatigue to set in while Jack looked almost ready to pass out with the encounter having snapped all of his energy.

Elsa slipped his dick out of her, allowing a spurge of white cum to spill out of her entrance and onto his rod. But luckily, she came prepared. Pulling out some wipes from her pants pocket, she wiped away the semen, cleaning herself and her partner before she laid down next to Jack on the ice as they both took a moment to regain their strength. Jack was on the moon. He's achieved greatly at asking Elsa Arendelle out and they got intimate together on the first date. Who would've thought? Jack must really be the luckiest boy in the world to have actually gotten to second and third base with the prettiest girl in school.

"Wow. That was incredible." breathed Elsa with fragile pants.

"Yes, it was." Jack replied with a nod.

"You're really not bad for a first-timer. Are you sure you've never had sex before?" asked Elsa curiously.

"Not really. I've been saving myself for you." admitted Jack with a tired look in his eyes.

"Really? I mean you've had plenty of other pretty girls out there, you know." reasoned Elsa, surprised that this was his first time, too.

"Yeah, but as tempting as that may sound, I've only had you on my mind." Jack reminded her.

"That's sweet." Elsa cooed with admiration, flattered by his compliment.

"So….does this mean that we're, um…..a thing now?" asked Jack, hoping that he was finally in a relationship with the girl he loved. However, Elsa gave a nonchalant shrug.

"Not really." She replied, much to his shock.

"What?"

"I mean, it was the best, but it definitely wasn't the greatest." Elsa replied, turning over to look at him, leaning her head on her arm. "Don't get me wrong, you were awesome and it was magical, but I kinda had to help you through it the whole time. Usually, a woman enjoys a good fuck when a guy has to take control and work his way through it without effort. You did great, but I'm afraid you're gonna need some serious practice."

"Practice?" repeated Jack, not sure how to process that information. "I don't understand."

"Listen, we're not official together yet, Jack. But we will be. I promise." Elsa assured him. "But first you're gonna need to know how to thoroughly satisfy a woman before we get there. So here's what I'm thinking. Starting tomorrow, you will be paired up with one girl after another of my own choosing, a harem if you will, and fuck the shit out of them. Each passing day of the whole month, you'll be having sex with one new girl for each day of the month of February. And by the last day of the month, if you have successfully satisfied each girl, I'll give you a choice to either be with me or with one of the women you've fucked. I won't care who you choose."

"So you're gonna be setting me up with several women just to teach me how to fuck you?" Jack replied, looking toward her, unable to believe what she was propositioning to him. After finally having sex with her, she straight-up tells him that she's going to have him bed a dozen other women before they are officially lovers.

"Well, think of this as like an educational experience. You'll get to know more people along the way and not to mention bang as many hot girls. Believe me, this is a once-in-a-lifetime opportunity. It's too good to pass up. Besides, I'm not taking no for an answer."

"And what if I refuse?" Jack gently asked.

"Well, it's simple. You refuse, then we can't be together." asserted Elsa strongly, which caused Jack to sigh. Then her tone shifted into a more gentler and comforting one. "Look, Jack, I'm not trying to humiliate you or exhibit you as a sex offender or anything like that. This is just to help you understand what certain women expect and I'm giving you my full permission to fuck a variety of attractive women. I know that you've had sexual thoughts about some girls, not just me. So I'm letting you copulate with them before we can be an item, if you want to, that is."

"What if I choose to want all of you?"

Elsa pondered this for a moment before stating, "That's up for debate."

"Alright, I guess I have no choice." Jack finally relented, which made her smile blissfully.

"Great! You won't regret it." Elsa told him.

"I sure hope not."

"You won't. I assure you, my dear." She reassured him. "One more thing. You can't reveal this to any of your friends until the end of the month. For now, we just let this be our little secret, okay?"

"Okay." Jack nodded, still somewhat uncertain.

That's when she gave him a rewarding smooch on the cheek, which at least got something of a smile out of him.

"Let the games begin."

And so we have begun with the one that started it all, yours truly, the snow queen herself, Elsa f***ing Arendelle. So Jack has finally gotten to second base with his longtime crush, but now she's telling him he needs to bed a bunch of other girls Elsa picks for him if they're ever going to be official. Crazy, right? Normally, any man would take this offer no questions asked, but Jack is not that type.

Who will be the next girl Jack will be fucking in the next chapter? Let me know in the comments (and don't be sending me any more complaints about my stories, either) and stay tuned.

Stay safe and avoid the coronavirus!