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Journal of a Brief Wearing Bunny

Tighty-Whitie Challenge

Chapter 1: The Eight Pack

Sharie Bunbury, more often known as "Mom" to her kids, had just returned home from her errands, and had begun putting the food away in the fridge. Her mind wandered a bit as she began to think about think about the man in the store who flirted with her. While she was quite flattered, and with him being quite handsome, it surprised her a little bit as she turned down his offer for a date. After all, she was aware of what would usually happen after each date, and it's why she's a single mother of four children.

Still, she loves and adores her kids to death, and would absolutely do anything for them. That's why after she put the food away, she would go over to the other bags, which would contain the other items from the other part of the store she went into. Magazines, toilet paper, fabric, blankets, and other similar items. Sharie reached into the bag and pulled out something else. She looked over it some, sighing a little. "Well, he is growing up," She said to herself, beginning to head into the hall, carrying the thing she took out of the bag. "I doubt he wants to wear such silly underwear all the time, anyways."

At this point, she had made it to the door of Dylan's room, using one hand to open the door and slowly peek in. "Hey Dylly, you in here?" She'd begin.

The male bunny was reclining on his bed, reading through a book when his mom had stepped through. Dylan looked up at her and replied, "Oh heya, Mom. Need something?"

She shook her head and stepped inside a bit more. "Well, not exactly. See, I got you something today, and I think you'd appreciate it," She continued, holding up the package she removed from her bag. Dylan's eyes widened some, but he was also somewhat confused.

It was an eight pack of plain, white briefs. While Dylan certainly appreciated it a lot, he knew that he could never get her to budge about buying plain underwear for him before. So why now? "Uh, well thanks Mom, but uh... can I ask why?" The bunny asked.

She gave a soft smile at her son before answering him. "Well, since you're getting older now, I figure you'd prefer to wear something more simple. You are in high school after all," She went on. "I'll need to wash these first, but you can wear these once they're done. On one condition though," She said.

"What is it?" Dylan asked her, rather curious as to what she'd say. What would be the circumstance he'd have to do to wear underwear?

Sharie replied to him, saying, "You must keep them in top condition. No rips, tears, anything like that. I know about your uh... well..." She said, moving the hair out of her eyes awkwardly, not wanting to bring up his engorged length. With how Dylan gave an embarrassed look, though, he understood what she meant. "...so you have eight pairs in total, and if you can keep at least one in good shape by the end of the week, I'll hand make some special tighty whities for you."

Dylan smiled a little and nodded. "W-well, thank you Mom. I'll be sure to keep them nice and tear-free," He would say, making his mom smile and giggle some.

"Glad to hear. I'll leave you be for now, Dylly-Willy," She'd coo, stepping out of his room and shutting the door behind her. Sharie walked down the hall and into the washroom. From behind a slightly open door, another bunny was peering his eye out so he could listen in to the conversation across the hall. Stevie quickly shut his door and snickered to himself, pulling out his phone to text the other older siblings of the house. He had a bit of a plan to have some fun with Dylan.

Awhile later, Dylan would be in the shower, cleaning himself off. His mom would drop off a load of clothes on his bed, eight clean pairs of tighty-whities resting on top of t-shirts and shorts. In the back, one little slit would be cut through, so that his cotton tail wouldn't be confined in his briefs uncomfortably.

The bunny left the bathroom after drying himself off and blow drying his hair and fur. All he would have around his waist was a towel to hide his groin. Dylan looked at the bed and smiled a bit, seeing the clean clothes waiting for him. He walked on over and let his towel drop. He then lifted up a single pair of briefs, stretching them gently in his fingers as he eyed them. Pristine and white, ready to be tried on. Dylan peered down to his crotch, seeing his flaccid, yet still quite big, length hanging in between his legs. He didn't know just how well these briefs were going to fit, but he wanted to at least try them on.

Dylan lowered them to his feet, stepping into them and slowly pulling them upwards. He tucked his package into his undies and waggled his tail so that it went through the slit in the back. With one final tug, he snapped the waistband and looked over himself. In all honesty, despite how large his bulge was, they still managed to stretch and fit themselves to the bunny's body rather perfectly! They felt quite thin, but Dylan had no complaints about his new underwear.

Dylan looked at himself in his full body mirror for a little. Naturally, he was quite slender and tall, but he couldn't help but look over himself in his new "mature" underwear. As far as he knew, this was probably the first time he ever looked at himself and he wasn't wearing undies with bunnies, stars, pumpkins, apples, or cartoon characters on them. He beamed and even posed a little. "Heh... I think I can do this..! One week is no big deal," He said to himself, feeling his bulge twitch some.

He peeked down and bit his lip, remembering his fat dick, ready to spring out if it got too hard. "Hah... better be careful though," He said to himself quietly. At that moment, he heard his phone buzz. The half naked bunny turned and saw that his girl-friend, Cindy, had sent him a text. He held his phone and read what it was.

"how's it going?" it read.

Dylan began to text her back, standing in the middle of his room. "Just chillin, wearing some new briefs my mom got."

After a few seconds, his phone buzzed again. "can I see? >/////<" Cindy had sent to him.

Dylan smiled a little and chuckled a bit, rubbing the back of his head, feeling his tighty-whities stretch outwards a little. Regardless, the bunny pulled up his camera on his phone and positioned himself in front of the mirror, showing off his body and bulge some. He snapped a picture of himself and sent it with the caption, "How do I look?"

After another short pause, Cindy had sent, "OMGG!! they look so nice! 0/////0"

Dylan's rod twitched some more, stretching his tighty whities outwards some more, pitching a little bit of a tent. He bit his lip and tried to adjust himself, realizing that these briefs were nowhere near as stretchy as the ones his mom make for him. If he wasn't careful, he was going to rip them! However, a nice picture of his erection stretching out his underwear would impress Cindy, so he pulled his camera up again, looking up into the mirror and getting ready to take another picture.

There was one thing that he had forgotten, though. He didn't hear anyone open his door, so when the bunny looked back up at the mirror, he let out a yelp as he saw his brother, Stevie, standing right behind him. If getting caught sending nudes wasn't embarrassing enough, Stevie would also grab a hold of the waistband, giving Dylan a nice, hard wedgie. This made him squeal out at the sudden pain of it. To make matters even worse, Dylan heard loud rips as the cheap pair of briefs began to tear from the wedgie.

The bunny's finger slipped and he took a picture of it, also sending it to his girlfriend. The picture was right at the moment the briefs ripped, so his cock was in the shot a bit. Dylan dropped his phone right after he sent it, so he had no idea about it. The bunny just stood there, hands over his naked crotch as Stevie laughed, holding onto the remains of his tighty-whities.

"Hah! Sending pics to your girlfriend, Dylly-Willy?" He'd tease, slapping his ass to embarrass him further, making him yelp out loudly.

"Gah! Stevie, quit!" Dylan began, blushing a bright red as he glared at his brother. "I can't afford to rip these briefs! And don't you know how to knock?!" He cried out to him, seeing Stevie swoop down and snatch up Dylan's phone. "Hey give that back!"

"Oh trust me, I know how to knock," He began, not looking up as he immediately began to rapidly send the pictures Dylan just took to every contact he had (minus his mom, of course). Melissa, Roger, and Cutie would be receiving the pictures, aside from Cindy. "I also know that you're trying to grow out of your funny bunny undies, and we can't have that!" Stevie said, dodging around as Dylan tried to take his phone back.

"Dammit, Stevie, give it back!" Dylan huffed, trying to reach for it. In the end, he was successful, but was too late. His eyes widened as he realized that the pictures he just took were sent to the rest of his family and friends. Dylan could hear loud laughter come from his other two siblings, as they apparently read the texts that Stevie had sent from Dylan's phone. As for Cutie, she would send a few texts to him.

"lol oh wow dude. cute body, though" She had sent to him, which made Dylan's blush grow more.

As Stevie walked out of Dylan's room, he'd turn to him and say, "Oh by the way, Mom says dinner is ready. Better hurry, Dylly-Willy," He'd snicker before shutting the door. The naked bunny was hiding his semi-hard cock in his hands, blushing bright red and huffing.

"Jeez... that's one pair already! I better avoid him from now on," He said, quickly pulling on a second pair of tighty-whities. As he put on his clothes, he'd quickly sent a text to Cutie.

"omg I'm so sorry, my bro did that."

Cutie quickly replied to him, sending, "lol don't worry, but give me a warning before u send more nudes."

Dylan set his phone down and rubbed his head, wondering what she meant by that. The bunny left his room and headed to the kitchen. Once he entered the room, he sat himself in between his siblings, who were grinning at him. He decided to try and avoid their gaze. Thankfully, they didn't say anything to him, as their mom was standing right near them.

Their dinner was uneventful, for the most part. They all talked to each other, talking about how their day was, talking about tv shows and movies and other sorts of interests that they had. It wouldn't be until after dinner that there would be a bit of a commotion.

Once Dylan finished his dinner, he stood up and moved to put his plate in the sink to rinse it off. What he failed to realize is that he sat in the chair that managed to have a stray nail head sticking out. While it didn't hurt him, it did manage to hook into his waistband some. Since Dylan was wearing some very loose fitting sweat pants, they wouldn't get in the way of the underwear. When Dylan moved away from his chair, his waistband got hung and ripped some. While it didn't seem to rip the whole pair off of him, it was very audible, and the sudden movement made his pants fall as well.

As he expected, Melissa, Roger, and Stevie began to snicker as they watched the spectacle unfold before them. "Pff... your undies are caught, Dylly-Willy," Roger said in between his laughs.

Dylan's ears folded in embarrassment as he quickly bent down to pull his pants back up and unhook his torn tighty-whities from the nail. "Thanks," He'd grumble. As Dylan finished putting his plate in the sink, he'd peek back again. The others were still quite amused, and he even saw his mom cover her mouth with a hand, but she was still visibly holding back giggles.

The bunny headed back into his room to review the damage to his briefs. As he tugged his pants down, he'd realize that the current pair of tighty-whities he was wearing would no longer stay up. They fell off of his rear quite often, even if he just pulled them up. He'd sigh and pull them off, tossing them away with the other shredded remains of his previous pair. He'd go to his underwear drawer and pull out another pair, starting to pull it up.

"Two down already. I dunno if these are gonna last six more days," He'd sigh.