JOABWB: The Jockstrap

Story by BunnyBriefs on SoFurry

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#20 of Journal of a Brief Wearing Bunny

Dylan goes through his losing bet and is forced to wear nothing but a silly looking jockstrap. The problem is, his mom is having company over! Will he be able to keep himself hidden?


Journal of a Brief Wearing Bunny

Part 8

The Jockstrap

"Kids, could you bring your dirty clothes to the laundry room please?"

Dylan's ears perked up as he heard his mom calling. He sighed and scooted out of his desk chair, heading towards the half filled hamper in the corner of his room. Normally, this type of chore would be nothing but a small, semi-boring walk to the laundry room to drop of his laundry. However, there was one little hitch that would make this small trek a much more humiliating act than it needed to be...

"Hey, Dylly-Willy, here's my pile!" Called the voice of the oldest brother, Roger, tossing a large ball of dirty clothes into his hamper as if it were a basketball. Naturally, he made it perfectly, though the stench of Roger's workout clothes didn't really make the bunny any happier. Usually, he'd just toss it right back at him, but Dylan couldn't do that. He lost a bet with his other brother, Stevie, and now he had to do all the chores of his siblings.

"Yo, Mommy's Big Bunny, don't forget mine!" Stevie called, dumping his dirty clothes into the hamper as well, weighing it down further. Dylan's cheeks flushed as his tail twitched in annoyance. There was another part to his wager, though. He had to do all the chores and walk around the house in nothing but a very skimpy, embarrassing looking jock-strap. The pouch was white, but covered in a rainbow assortment of lipstick kiss marks. It didn't help that the waistband of it read boldly and proudly, "MOMMY'S BIG BUNNY" in bright purple letters. Clearly, the attempt at flattery from his own mother made him even more embarrassed to even put on the piece of clothing. At least it provided support and comfort.

"Mine, too, Dyl," Melissa called, dumping her own clothes on top of the hamper, making it even more cumbersome for the youngest sibling. Before allowing him to walk off, she gently slapped his rump, making him flinch and yelp out. She responded to this with a laugh of her own before shutting her door. Dylan groaned and continued his way into the laundry room, located right near the dining room. Thankfully, the door was open, so he wouldn't have to worry about setting down the heavy hamper or shifting it around to try and keep it up with one arm.

He was greeted with the loving, doting voice of his mom, Sharie. "Aw, did you want to help your siblings, Dylly-Willy?" She cooed, helping him out by taking the hamper from his arms, setting it to the side and starting to sort. Her eyes roamed over his half-nude form, particularly over his jock-strap, smiling happily. She was the one who made it for him, and was quite happy that she saw him wearing it quite often this week. She still had no idea that Dylan was working off a bet, but he didn't want to tell her that.

Instead, he gave a small smile, looking down shyly. "...yeah, you could say that," He replied, starting to turn around and leave. Before he could, though, a sudden finger tugging at Dylan's thick waistband got him to freeze, his cheeks burning a bit brighter.

"By the way, bunnykins, would you like me to wash your jock again?" She asked him sweetly and innocently.

Dylan's ears flopped downwards a bit as he laughed awkwardly. "Haha... n-no it's fine, mom. You did just wash these yesterday," He replied. While his statement was indeed true, the real reason was because he knew that his siblings would take an opportunity to make fun of him if they saw him walking back completely nude. Sharie leaned down and smooched her son's cheek.

"If you're sure, Dylly," She replied, going back to sorting out clothes. Dylan hurried off back to his room, both hands trying in futility to hide his bulge, which was starting to swell up slightly. He didn't know why the fantasy of him running naked in embarrassment riled him up, but he knew it was best to hide in his room before his siblings saw.

The day continued on in relative normality, which included any time Dylan got teased about strutting around in his goofy underwear while he was trying to do something. Nothing too unusual. It wasn't until around dinner time that their mom would speak up. "Oh, by the way, tomorrow I'm going to have a few clients over that have commissioned me to do sew them some clothes!" The other bunnies were mildly impressed, congratulating their mom. After all, it was quite an accomplishment and a step in the direction of gaining more steady work and eventually making her business bigger. "Thank you so much, kids! Just remember to not stop by my sewing room until they've left. They'll be naked and I don't think they'll appreciate anyone peeping in," She said with a giggle, her cheeks flushing a bit.

The others looked over at Dylan, grinning to themselves. Dylan squirmed in his seat, feeling flustered by their accusatory glances. He knew better than to walk in on people changing, but his siblings often loved to treat him like a big pervert. He kept his hands to his crotch, keeping his bulge from growing (or rather, showing itself). Of course he'd still be sitting in his jock-strap, so it'd be easier to spot. Once they all agreed to not walk in on the clients and dinner continued. Dylan made sure to do dishes, since that was his responsibility as the loser of a bet. He didn't mind so much, though he did wish that Roger, Stevie, and Melissa didn't slap his ass as they walked by as a way to show their 'appreciation' for his kindness.

After taking a shower and indulging in his hobbies for a little bit, Dylan soon went off to bed, knowing that he'd have to stay in his room most of the day. Mostly for the fact that he didn't want any strangers staring at him while he walked around in his embarrassing jock-strap. All he knew was that tomorrow would be the last day of the bet, and afterwards he wouldn't have to do everyone's chores half naked.

Next morning, after eating breakfast, Dylan went off to his room. Fortunately, his siblings didn't have any chores for him to do, so he could stay in his room for most of the morning. Strangely enough, when he texted Cindy and Cutie, neither one of them seemed to immediately respond to him. This concerned him, but they were probably busy with something, so he didn't worry. Eventually, he heard knocking at the front door, which was answered by his mom. He heard speaking from various women, but he didn't bother to poke his head out. One of the voices sounded quite familiar to him, though.

It wasn't until there was a small knock at his own door did he figure it out. He quickly shimmied a blanket over his half naked form and blushed. "Who is it?" He'd call out.

"It's us, Dyl!" Squeaked the voice of Cindy. He sighed and relaxed a little, but not by much. After all, despite the fact that they had seen each other nude before, it was still a bit embarrassing that they'd walk in on him wearing... this. He knew that they were aware of his lost bet, especially Cindy. However, he had not shown what he was supposed to wear the whole week, and was almost hoping they'd forget about it. Of course they'd be right outside his door. Still...

"Oh, c'mon in, girls," He sighed, watching the door slowly open up, revealing the mouse and bunny girl. Cutie lifted an eyebrow as she looked over him, as he had draped himself in his blanket to cover up. Cindy flushed and shut the door behind her as they stepped in. "So uh, I'm gonna assume your parents are here for a fitting?"

"Yup. Cindy's mom is friends with mine, and she decided to bring her over plus another family friend of ours," Cutie replied, sitting herself right next to him. The girl bunny wore a simple skirt and a jacket, with some form of tank top on underneath. Cindy sat to his other side, wearing the same thing, except in a different set of colors. "So I'm guessin' this is part of the wager you lost?" She teased, using a hand to playfully tug at the blanket, which Dylan tried to keep up, laughing shyly.

"Er... yeah... today's my last day though, so I won't have to walk around half naked around the house after today."

Cindy smiled and leaned herself up against him, nuzzling against his cheek and flushing. "Y'know, Dyl, we haven't gotten to see what you were made to wear..." She trailed off, her own hand moving to his lap, gently placing it against his crotch and rubbing a little. Naturally, his bulge started to form underneath the blanket, making him groan out.

"Gmmf... g-girls, please... it's embarrassing..." He mumbled, accidentally losing his grip on the blanket, allowing Cutie to tug it down. Once it fell to the floor around his feet, both of them gasped gently, seeing the jock-strap adorned on their bunny boyfriend. Dylan peeked down shyly, rubbing his arm as his bulge slowly stiffened outwards in arousal. His heavy balls hung in between his legs, covered up by the pouch. Even while he was sitting, the two girls could easily see his exposed rear. The two looked to each other, grinning as they reacted in the best way the knew how.

They leaned up against Dylan, starting to kiss at his cheeks lovingly, making him squirm. They also placed their hands on his growing underwear tent, making him groan out a little more. His dick twitched some as the two cooed and teased him. "Damn, Dyl, you're like, the king of making goofy undies look incredibly sexy, huh?" Cutie giggled, batting her eyelashes at him.

"Wow..! Y-you should ask your mom to make you more jock-straps..!" Cindy sighed cutely, letting her other hand go down to shyly feel his butt, making him jump at her touch. Of course, he didn't pull away from either of them, clearly enjoying the attention he was receiving from the two. His own arms found their way around their waists, pulling them in closer. His hands reached down to grope their asses, reaching under their skirts. Neither one minded, as they began to grind into his palms.

Just as Dylan's fat cock got as hard as it could, stretching out the pouch of his underwear, the door was soon opened. "Hey, Dylly, could I borrow you for a- oh goodness!" Sharie gasped out, blushing brightly as she walked in on her son having a lewd moment with his two girlfriends. The three of them froze after letting out a yelp of surprise. His erection didn't die down, but he still felt royally embarrassed. Cindy seemed to try and hide her face into Dylan's side while Cutie merely looked away, as did Dylan.

Sharie quickly peered away, hiding her smirk with a face, also stifling back giggles. "Ahehe... uhm... sorry that I'm... haha..! Interrupting something... but I gotta borrow you for a second, Dylly-Willy..." She giggled. Dylan looked between his girlfriends, all three of them looking confused. He looked back up bashfully, his face as red as an apple.

"Uh... can I get dressed and have a second first, mom?" He had a bad feeling that whatever he was needed for, it had to do with the clothes fitting she was doing. Unfortunately for him, his mom quickly reached over and grabbed one of his hands, quickly tugging him up and making him squeak out.

"Actually, I think how you're dressed now is the perfect example! Excuse me, girls," She cooed to the two girls on his bed, quickly walking out of his room with the hung bunny in tow. Dylan began to stammer out excuses, yelping as she quickly dragged him to her sewing room. His massive cock and large balls bounced heavily beneath him, using his one free hand to try and hide his exposure, but with no luck. It wasn't long before she brought him into her sewing room. Dylan shut his eyes tightly, awaiting the sound of three women gasping.

Sure enough, that was the sound that met his ears as they folded back in humiliation. As his cock twitched in his embarrassingly dumb jock, he soon heard one of them go through a loud fit of giggles. Immediately, he knew who it was without even opening his eyes.

"Ooooh my oh my! Dylly-Willy really can stretch it out, huh?!" Laughed the voice of Molly, Cindy's mom. He knew from past experience that she had more than just a small crush on him, having brought him to her bed one night during a sleepover and fucked him senseless. She knew first-hand just how large he could get.

"Gracious me... how incredible that he doesn't even rip it past the seams! I do have to wonder what caused his... package, to become so engorged, hmmm?" Purred the voice of an elegant sounding woman. Dylan slowly opened his eyes, wondering who it was who said that. To his horror, he noticed that all three women were sitting in chairs, and all of them were covered in only a simple towel, their clothes folded up elsewhere. To the far left, he noticed Molly, both hands covering her mouth as she stared quite blatantly and excitedly at the half naked bunny. The towel barely fit around her large bust, it seemed, though he figured she wouldn't care if she accidentally flashed him.

To the far right sat a tall, thin bunny woman, who Dylan assumed to be Cutie's mom. Her hair was styled in a very regal manner, as the woman herself had a very rich, wasp-y vibe to her. Her own chest was very small, though it only made her look more elegant. A small thought entered his mind of wondering how Cutie managed to avoid acting like a hoity-toity rich girl with a mother like this. She was also staring at Dylan, an eyebrow cocked as she smirked in amusement. She was looking at his crotch in a way that almost said, 'Oh dear, you actually wear those?' While she was certainly not as busty as the other mother, she was still quite attractive in her own way.

As for the woman sitting in the middle, he had no idea who it could possibly be. Most likely that 'family friend' Cutie brought up earlier. She was a buff, muscular looking woman, who was a black panther. Her hair was cut extremely short, but her own eyes were staring at his package, eyes wide open. Her chest was quite huge too, barely fitting in the towel given to her to wear. With a somewhat deep voice, the woman spoke up to his mom. "Very impressive, Mrs. Bunbury. It's obvious you know your way around a sewing machine if you can make something to fit... him." Dylan couldn't help but notice that she looked directly in his eyes as she said the last word, almost purring it out to him. He gulped as his dick twitched a little.

Sharie ruffled Dylan's hair, making him squirm a bit. "Why thank you, ladies! Trust me when I say it was very hard to find stores that could supply his needs. So now that you know I'm capable, shall we get to measuring?" She cooed, letting the three women before them nod their heads. "Excellent!" She planted a kiss on Dylan's head and turned him out, pushing him by the tush out of the room. "Go on back to your room, Dylly-Willy! Don't want you peeking on these women, now!" She giggled, waving him off. He wasted no time in hurrying out, moving his hands to hide his exposed butt, tail twitching behind him as he sped off.

As he left, Molly sighed lovingly and kept staring, even after he left. The panther looked to the rich bunny lady and asked, "What do you think, Francine? You said he's the one your daughter fancies?"

"Oh indeed, Sheila. Carla absolutely adores him," She drawled, smirking in amusement still. "It must be quite a hassle for him to have to lug that thing around, though."

Sheila grinned and looked back to Molly, joined with Francine. Molly still looked love-struck, grinding her large thighs together. "I imagine. Bet he knows how to please a woman with that fat hog, though," She laughed. Cutie's mom joined in with her own haughty laugh.

"Oh, how bawdy of you," Francine laughed, nudging her arm.

Meanwhile, Dylan continued to stumble down the hall, face burning as red as it could. As his stiffy bounced with each step, he grumbled to himself. Why was he always being humiliated in front of hot women? He felt himself to be quite lucky to have already found two girlfriends, because if he hadn't, he had a feeling he'd drive off every woman he'd try to date. The fantasy of being in a fancy restaurant in nothing but a pair of Loony Toons briefs, supporting his fat hog filled his mind. The many patrons in the restaurant were laughing and pointing at him, his date, doing the same.

"Oh my god! No way I could ever date a man who still wears underroos like that!" She guffawed in his mind.

Dylan shook his head, quickly removing that thought from his mind. He opened his bedroom door and sighed out. "Well that was a humiliating-" He froze, stopping mid sentence as he took in the sight before him. Both Cutie and Cindy were now leaning against his bed, showing their asses towards him. The only article of clothing that remained on either one of them were their panties. Cutie's pair would be white, but with a cute pink lace trim to it. She shook her rear teasingly to him, her tail waggling as she stared back at him lovingly.

Cindy's underwear would somehow fit around her fat bubble butt. Her pair was pink, with Daisy Duck stretched out over her ass. She was looking back at him too, though with a lot more bashfulness than Cutie. "Kept us waiting, Dyl..." Cutie cooed expectantly, reaching her hand over to grope Cindy, making her squeak out.

Dylan blinked before slowly moving his arm back, shutting the door behind him and quickly locking it. His embarrassment about being seen by three older women were gone and were instead replaced with lust for his two girls. With both hands, he pulled the jock-strap down and stepped out of it, letting his massive dick flop free. He walked towards the two and pushed it between them, hotdogging their asses as his hands groped their cheeks, tugging their panties in a teasing manner. Of course, the two enjoyed it, tilting their heads and kissing at his swollen, drooling tip as it reached to their faces.

"Mmh.. ooh... I-I've missed this..." Cindy moaned cutely, closing her eyes and kissing his dick more.

"Same here... d-don't think I forgot about that night where you two left me with blue balls..!" He groaned, giving the two a slap on their ass, making them yelp out and jump a bit.

Cutie turned to him grinned. "Whatcha gonna do about it, Dyl? Punish us~" She said in a mocking tone, wanting to push him into a dominant attitude. Sure enough, his two hands roughly gripped their waistbands and tugged them downwards. They shimmied their hips to wiggle out of their panties, kicking them off. In a move that surprised the two, he gently cupped his hands around the underside of their pussies, pushing them onto his bed. Cindy, of course, was already soaking wet, but both of them let out a squeal of a moan. They turned to Dylan as he soon climbed up on the bed, laying on his back and pulling the two close to his cock, panting heavily.

He was flushing quite a bit, but with how much his cock was twitching and leaking, it was obvious he wasn't willing on waiting. He already went almost two weeks without cumming, and he wouldn't make the mistake of holding it in any longer. As long as he had his two naked cuties with him, he was going to make them feel good.

It wouldn't take long for the two to get the hint and start having some fun with him. Because of the fact that he could not fit his massive bunny cock inside either one, they had to improvise. Thankfully, they figured out a way to pleasure themselves and their bunny beau. They wrapped their arms around his shaft, pulling themselves as closely as they could to him and started to grind their wet crotches up against his shaft. Cindy and Cutie panted and moaned out, letting their hanging tongues reach out and sloppily lick and kiss at his leaky tip.

Dylan was in pure heaven, eyes often fluttering closed for a few seconds before re-opening to see his two girlfriends hump and grind against his cock in a needy, yet lustful, fashion. Cindy's own eyes were shut tight, her body shaking and shivering in pure bliss. Cutie was also shivering as she humped, but her eyes would sometimes open up a little to stare lovingly at Dylan. With how much he felt like his cock was pulsating, he knew it wouldn't be long before he came all over these two beauties.

Cindy would be the first one to orgasm, squealing and squeaking loudly as she humped sharply and needily against his dick, gasping and shuddering as Dylan felt immense gushes of her fluid squirt all over his length. She clung her lips to his cock, kissing and smooching against it as she rode it out. Cutie watched, laughing in between her own little moans.

"H-hah..! Looks like muh-mousie came fuh-fuh...~ first..! Such a muh...muh... muuuaahaahhh!~" Cutie teased, unable to hold back her own orgasm, unleashing her own ejaculate on Dylan's cock. His ears twitched as he listened to the two moan and squeak in ecstasy, kissing lewdly against his tip. "Such a good dick..." Cutie murmured in between groans. He knew with how heavy his breathing was getting, that comment was more than enough to make him cum.

He gulped and humped upwards in between the girls a little, groaning out and grunting as his dick shot loads and loads of his cum like a geyser. It lasted a good two minutes, splattering his creamy bunny batter all over his stomach and legs, as well as all over Cindy's and Cutie's face and body, completely coating them. Soon, the only noises coming from the three would be groans, gasps, and squishes.

Eventually, the three of them calmed down, resting a little bit. Dylan watched as Cutie initiated a make out session with Cindy, suckling and lapping at her cum coated lips, swallowing any seed they licked across. After doing so, Dylan was pulled up into a three-way hug, which he reciprocated. Despite the fact that this made a big mess, he didn't care. He soon pulled away, panting heavily and placing a kiss on their lips. "That was amazing, you two... god I love y'all..."

"We love you too, Dyl..!" Cindy cooed, beaming at him.

"Yeah..! That was so much fun! We've gotta do this more often, babes," Cutie teased, resting her head against his chest. After a minute of snuggling, she spoke up again. "...we'd better get cleaned up though before our moms catch us."

With a nod, the others agreed and they headed to Dylan's bathroom to clean up. They didn't have enough time to shower, as their wet fur and hair would make it obvious where they were. Instead, Dylan put three towels under water and gave one to everyone, using them to wipe off any mess that was on their fur. Afterwards, he let them share a hair dryer to dry and fluff out their fur.

Even though they all still smelt somewhat... musky, they looked much cleaner than before. As the girls got dressed, the two bunnies watched Cindy tug up her panties, sharing a small grin between each other. "Daisy Duck, huh?" Dylan teased, making Cindy blush and turn her head, looking somewhat embarrassed.

"...my mom had your mom make these for me..." She murmured, making the other two snicker some.

"I think they're cute on ya, Cindy," Cutie said, pulling on her shirt. "I'm just glad my mom doesn't make me wear undies like that." She froze for a second, turning to glare at her two lovers. "And don't you dare go give her any ideas!" The two nodded rapidly before she nodded and huffed. "Good! Last thing I need is my mom making fun of me." Thankfully, they finished dressing just in time, as they heard the voices of their moms call out.

"Cindy! We're heading out! Say goodbye to your boyfriend and let's go!~" Molly's voice rang out.

"That includes you too, Carla. Come along," Came the voice of Francine, Cutie's mother. The two girls turned to Dylan and kissed his cheeks, after having gotten dressed.

"See you two around!" Dylan said, waving as the two left his room.

"Later Dyl! Love you!" Cindy replied.

"Later, stud~" Cutie flirted, winking to him before stepping out and closing the door.

Dylan sighed and stood there for a moment, smiling to himself. He was incredibly lucky to have those two as his lovers. He turned around and went back to his bathroom. He figured it was time to give himself a proper shower.