A/N: This is based on a prompt from dailyAU DOT tumblr DOT com:

"My friends dared me to buy 20 condoms but i didn't realize that the cute cashier would be working tonight so i avoided eye contact as i piled them onto the counter and please stop laughing so hard, oh my god it's for a dare okay i've never had sex in my life and once you stopped laughing, i swear i fell in love with that sparkle in your eye as you grinned wildly at me and asked me out for a drink" AU

My friends Twigman242 and InsertACreativeNameHere also wrote drabbles based on this prompt. Check them out as well!

When he picked up a box of Durex Intimate Feel condoms from the store shelf, Hiccup decided he hated his friends. Hell, he wasn't sure if they were really friends. Didn't friends do fun things on Friday night? Go out, drink, have a party? Not that Hiccup liked doing those things, the very smell of beer made him gag, but he'd prefer it over… this.

"Oh look, these are perfect for you, Hiccup!" Snotlout said, pushing a box of B Close: Smaller Condoms in the shopping basket. He groaned, but decided not to put them back. The sooner the basket was full, the sooner he could forget this ever happened.

"Are you sure those are small enough? I think these should fit!" Tuffnut said, tossing a box at Hiccup. It narrowly missed the basket, clattering to the floor. The sound echoed through the aisle, and Hiccup was glad it was nearly closing time, at least. No families with small children to glare at them at 8 PM.

He bent over, careful not to spill the contents of his basket, and rolled his eyes when he picked up the box of Finger Condoms. Feels better than wearing nothing!, the box said. This one he really wanted to put back, but what was the point.

It wasn't like he was ever going to use these anyway. He'd just… go to the cashier, have the most painful horrific awkward minute of his life, put the condoms in his backpack, and throw them all in the trash when he got home.

Stupid dare. Why had he agreed to do it again? Oh right, because he couldn't resist peer pressure, especially when Snotlout and Tuffnut started teasing him over his… lack of experience with condoms. And honestly everything condoms were associated with. And then Ruffnut joined in, saying they would get him started on his 'journey to not being a total virgin'.

And according to her, the first step on that journey was… going to a supermarket on Friday night and buying twenty condoms. He had protested, of course, but when they asked if he really had anything better to do on Friday night, there was little Hiccup had been able to say.

Fishlegs dumped a box in the basket, and Hiccup was pulled out of his daydream to see a simple box of standard condoms. Well, the size still said 'Large', but from what Hiccup could tell those were average sized. What dumb scale went from 'above average' to 'extra extra large'?

The box had a picture of a man and a woman in bed together. The blonde woman reminded Hiccup of the fact that while he hadn't had plans for tonight, that didn't mean he hadn't had plans for plans.

He had been so close to getting a date. Astrid was there in his class, this morning right before lunch. He had it all planned out. They'd sit next to each other, laugh at Professor Bucket's antics, and then when the bell rang, he'd ask her out.

Of course, his plans never worked out. His bike had a flat tire, making him late for the class, and the only empty spot had been two rows behind her. And then when the bell rang, Dr. Bucket stopped him, wanting to talk about his art assignment.

By the time he had reached the cafeteria and saw Astrid surrounded by her friends, his courage had dried up.

So now he was here, being dared by his classmates to buy condoms he'd never use because the only person he could imagine using them with would never go out with him before the expiration date… three years away. Seemed about right.

"Ooh, a surprise pack. Never know what you're gonna get!" Ruffnut cackled, throwing a large brightly colored box in the basket. Hiccup frowned when he examined it, but the content count sparked anger.

"Hey, this one already contains 40… uh, thingies!" he shouted, cringing at the echo. "You said I only had to buy 20!"

"Twenty boxes, young Hiccup. Twenty boxes. You don't want to run out before your training is complete, do you?" Ruffnut said, overly calmly like she was talking to a toddler. Hiccup glared, but decided not to push back. This was not a good place to make a scene.

"Ooh, flavored ones! Which one does A- uhm, Hiccup like?" Tuffnut said, and Hiccup whipped around to look, immediately recoiling at the… exotic tastes people came up with.

"It doesn't matter, does it? He's not the one who will… experience that part," Fishlegs said awkwardly, grabbing another generic box to put in the basket. 8 boxes in there now. Just a few more.

"I don't know, at his dating rate he's gonna have to suck his own-" Snotlout said, before Hiccup shushed him. Sure, the store was practically deserted, but there were limits dammit.

"Just grab one of every flavor. Strawberry, chocolate, vanilla. Hehe, they even have banana flavor," Ruffnut said, pulling Hiccup's arm holding the basket closer to the shelf so she could push a whole row in.

"So are you guys gonna pay for this?" Hiccup asked after gulping at seeing the price of the surprise box.

"Dude, it's your journey, you're gonna pay for it. Besides, your dad gives you tons of cash, you can afford it," Tuff said, and Hiccup rolled his eyes. A lot of money to waste on something he was gonna throw away, but there was no getting out of it now.

"And I think that's about it! The started pack for Hiccup's Journey to Becoming a Man!" Ruffnut said, tossing a box of 'Trojan: Fire and Ice - warming and tingling sensations for both partners' in the now overflowing basket. Hiccup used his free hand to stop the peach-flavored ones from falling out, and sighed deeply.

Time to get this over with. This wouldn't be so bad. It was just a retail worker. They're used to crazy stuff. Hiccup was sure the cashier wouldn't even register the stuff he was buying! Like some random guy would care that a random stranger was buying condoms. Even if it was an… interesting assortiment of condoms.

He took a deep breath, before walking out of the aisle towards the registers. He had taken two steps towards them when he froze.

There was only one cashier. That wasn't what scared him. It was normal for there to only be one around this time. No, it was the fact that he recognized that hair, that braid, even as she was turned away from him.

Hiccup heard his 'friends' snigger behind him, and he knew he had been set up. Ruffnut was friends with Astrid. Hell, Hiccup had seen them together at lunch today!

In less than a second Hiccup decided to back out. She hadn't seen him yet, he could put everything back and buy something normal. He doubted she was in on the prank.

But when he turned around and saw his friends' heads peeking out behind the shelf, he hesitated.

"Come on, become a man!" Ruffnut whispered loudly, and he quickly glanced over his shoulder to make sure Astrid hadn't heard that. But she was focused on a book she was reading. She looked pretty like that, off in her own world. And Hiccup suddenly felt a fire inside him, something that made him turn back around and walk towards the register with big steps.

The moment she heard his footsteps and looked up he regretted everything in his life that had led up to this moment.

"Oh, hey Hiccup! Here for some late-night shopping?" she asked, putting her book down and marking the page. He couldn't possibly run away now.

"Uhhhhh… something like that, yeah," he said resisting the urge to put on his hood to have something to hide behind, and instead just putting the basket upside down over the belt.

Astrid was deadly silent when the boxes bounced all over her belt, thankfully not falling over the edge. He refused to look in her direction, instead staring at his basket as he put it on the pile of other shopping baskets.

A few seconds passed during which Hiccup desperately waited for the beeping of the scanner to start, but instead he heard a chuckle.

"That's quite a haul," she eventually said, and Hiccup involuntarily looked up to see her barely holding in her laughter.

His brain went into overdrive trying to think of something, anything to say, but all that came out of his mouth was a choked grunt.

"Is this all for you? There's… a lot of different sizes in here. Are you sure that's what you want? They gotta… uhm, fit," she asked, finally starting to scan the generic boxes.

Oh god, oh god, oh god, he couldn't say no! That'd be backing out of the dare! But if he said yes, what would she think? That he was buying them for friends? That he had crazy parties?

What if she thought that they were for his… partners?! Partners who had parts that needed condoms? Enough partners that he needed so many different sizes? That'd put quite a damper on his plans to ever ask her out. Of course, this entire event had already pushed that back by like 2 years before he'd even consider it, but now he could never look her in the eye again!

"I… uh… I... You…" he stuttered as the scanner kept beeping, and from the corner of his eye he saw she had now reaching the more.. adventurous condoms. Oh gods, why was she chuckling? Was that… Is she laughing?!

Hiccup looked up again to see Astrid holding a bright yellow box saying 'Trojan XXXL Extra Ribbed - for that bareskin experience', her eyes darting between it and him.

"Pfffffff, I'm so sor- Hahaha, I really should be more professional but… HAHAHAHAHA" she laughed, and Hiccup wasn't sure what the funny image in her head was. Him wearing it, or him being in bed with someone who was wearing it? His face heated up, and he rubbed his hand through his hair, hoping she'd be done soon.

"Your face is as red as these ones!" Astrid shouted, doubling over from laughing as she picked up the strawberry flavored condoms, and he couldn't take it anymore.

"It's for a dare, okay! I wasn't… gonna use them!" he blurted out, and Astrid dropped the red box.

"I don't even know how to use them," came out before he could stop himself, and Astrid finally stopped laughing. She suddenly turned her head towards the toiletries aisle, and Hiccup heard scrambling as the four teens tried to hide.

"I knew it! Ruffnut was acting weird all day, asking about my schedule!" she said heatedly, and he looked back at her.

Her eyes burned brightly with rage. Her hand was balled into a fist, the big muscle in her arm clenching. Her lips were squeezed together, and suddenly he wanted to do nothing more than to kiss those lips. His breathing became heavy as blood rushed south.

Oh gods, this is not the time, Hiccup! Stop staring at her, she'll notice! Stop staring! You just admitted you don't know how to put on a condom, she'll know you're a pathetic virgin!

Somehow Astrid couldn't hear the voice in his head screaming at him, as she simply smiled when she met his gaze again.

"You know, there's nothing wrong with… not having a use for the condoms," she slowly said, scanning the last few boxes. His head started spinning, and not just from lack of blood. That was not what he expected her to say.

"I'm guessing your friends probably riled you up, eh? I know Ruffnut, she can get intense about these things. But don't feel bad if you're not ready for that yet," she continued, and Hiccup suddenly wondered if she was talking to him or to herself.

"Uh, thanks," he said, grabbing a few bills from his jacket to pay. She chuckled again when he took off his backpack and shoved the condoms into it with as much dignity as he could muster under the circumstances.

"You know, my shift is over in five minutes. If you don't want to hang out with those knuckleheads for now… we could do something together. Not with the condoms I mean, not yet at least-" Astrid slammed her hands over her mouth as Hiccup stared at her in shock. He was pretty sure his eyebrows had disappeared behind his hair, that's how wide open his eyes were.

"Forget I said that, please. My point is… would you like to grab a drink with me?" she said after an awkward minute, and Hiccup nodded, head spinning.

"Okay, great! I'll just wrap this up-" she said, before being interrupted by Hiccup's shocked laugh.

He was not proud of laughing, she probably hadn't even noticed the wordplay, but his brain was too fried to think about anything other than what had just happened and the objects in his bag.

"I, uh, I'll just say bye to my friends. I'll only take a minute," he managed to say, immediately regretting the last part when Astrid laughed instead.

"Not like… Okay, I'll come back here in five minutes, and then can we just… forget this thing ever happened? Start fresh?" he begged, sure his face was red as strawberries again.

"Throw out the old wrapper and put a new one on?" Astrid blurted out, and then they were both laughing. It took a bit before they both calmed down.

"Okay, see you in five," Hiccup said, and as he walked back to the other teens, he couldn't help but be glad he had accepted the dare.

And maybe he wouldn't immediately throw all the condoms away. Just the extra small ones.

A/N: Thank you for reading! If you liked it, please leave a review, and check out Twigman's and Slavic Viking's drabbles! See you later!