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Author Topic: A Bet to Lose  (Read 30077 times)

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Jacqueline

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A Bet to Lose
« on: May 20, 2020, 05:42:43 PM »
[Readers who didn't like what happened in my last story can rest assured that no such thing happens here.]

Zoe did not like her life very much.

Heather, her mother, had given birth to her and her little brother Richard just ten months apart, the perfect age for him to be just immature enough to be annoying and just old enough not to be easily dealt with. Their father had to make a choice between his family and heroin when she was just three years old, and he had come down firmly on the side of heroin. And she'd just recently learned, less than half a year ago, that she couldn't really rely on her mother anymore, either.

But her mother wasn't there that day, and her brother was, and they were arguing over the list of chores she had left behind.

"I know what you're going to do," she told him after he suggested a division of labor. "You're going to go over the house doing a lazy-ass job for fifteen minutes, you're going to dust by wiping a cloth real quick over some things, then you're going to mow the lawn by running back and forth for another fifteen minutes, and then you're going to play Starcraft while I'm doing all the laundry, and drying the dishes properly, and scrubbing the toilet. Which will take me a lot longer than it will take you." Things weren't always quite like this between them, but last Christmas, and his thirteenth birthday two months ago, had soured her on both him and her crazy, stupid mother. Fortunately, her mother had told her that Zoe was free on her own upcoming birthday, and she also hadn't taken her children to the wedding that she had flown out to, saving money by flying out Monday afternoon and coming back Thursday morning.

"I'm not lazy like that, and you're playing that game, too!" he argued. She'd taken it up last month, half to see what he liked about it so much, and half to be somewhere that she wasn't being treated like the girl her mother wanted to treat her as.

"I've seen you sluff chores so many times. There's this this thing called diligence, I have it and you don't. I'm actually practicing that game. Are you even diligent enough to do that?"

The expression on his face changed a bit, and he leaned his head back in a haughty expression. "Have you even looked at the professional Starcraft players? They're all men, literally all of them. Girls can't play this." Her face screwed up in shock. She thought what he said on Christmas was bad, but this... "This just isn't a game for females, Zoe. You can't beat me, I've beat the computer on Harder! There's no way you'd win!"

Zoe blinked. She'd been using the computer, rather than human opponents, to practice. He'd actually offered to help but he did not want him looking over her shoulder, not after those two "celebrations". And now he'd just admitted, although he clearly didn't know it, that she was better than he was, despite him having had it for years and her just starting last month. She'd been watching videos in between practicing 1v1s against Very Hard and had defeated Elite. "You really are a waste. Get upstairs, right now, and sit your ass at your computer and wait for me to beat it."

"Wanna make a bet?" he offered right away.

"Fine. Loser does all these chores, all of them, the right way."

"While wearing a dress!" he yelled at her.

"Fine, you little shit! While wearing a dress!" She was upset, she was deeply upset, and she realized that it had to be intentional, him trying to throw her off her game while thinking he had the chance to humiliate her further. If this little shit thought he was going to make her wear a dress, let alone the same junior prom dress she'd worn on his birthday, or that Christmas abomination...

Seething with rage, she followed him upstairs, and played him 1v1 in Starcraft 2, her Terran and him Zerg. He kept sending individual Overlords to scout, kept sending in small units to probe, but he didn't expand properly, and then the overconfident little bastard had sent his whole army straight into the teeth of her defenses and got destroyed. She'd rolled over him just like the tanks she sent. "Get in here!" she shouted, and waited at her open door for him.

"Before we start, before we even start, I'm going to remind you of last Christmas, just to make sure you know why I'm about to do this stuff to you," she said as he approached. "Mom was telling me that I needed 'more practice in being feminine', and I was telling her that I didn't want to wear that God damn dress because it's awful. But then you said, AND I QUOTE, 'You're lucky you're a girl, because you get to enjoy being pretty,' just rubbing it right the in. And then she AGREED with that, she agreed with that, and she threw me out there and said I was grounded from everything if I wasn't the perfect hostess in a jingle dress. And you know who else was at that party, those cousins, those college cousins who stared at me like they wanted to rape me AND I'M THIRTEEN YEARS OLD. And I swear to God, one of them stuck his tongue out at me, like he wanted to lick my candy cane legs. I told Mom that I was done, I was just done, and I even tried to tell her about the cousin who did that, and you know what she said? She said I wasn't going to get any presents if I kept acting that way. What kind of threat was that? She never gets me anything good, she never even gives YOU anything good. So I came up in here and closed the door."

Richard stayed quiet, his lips pursed and eyes closed.

"But then she comes into my room, and says, 'why didn't you just listen to your brother, Zoe, why couldn't you just enjoy it because you're a girl, why do you keep making a big deal out of nothing', with me in that jingling dress from hell after my literal cousins AND YOU had been staring at me like a piece of meat?" He looked at her like he wanted to dispute that, but she kept going. "And then she tells me that I'M the one who ruined Christmas?" He was going to say something, but she overrode him. "Do you have any idea how hurtful it is, when someone is doing something to you that you hate, that you should just learn to accept and enjoy it, that it's not that bad so you shouldn't take it so hard and should just go along with it? Do you have any idea at all how awful it is to be told that? It's like if..." She didn't finish her sentence, and she realized that she was practically screaming at him and forced herself to calm down.

"I didn't mean..." he started.

"I don't care what you meant," she snapped. "You stared at me on Christmas and you stared at me on your birthday when you weren't playing with your stupid toys. You want to staring someone wearing a dress so much? Here you go, here's your chance. The whole thing, just like I wore it." She furiously dragged a cardboard box out of the back of her closet. "Enjoy your Christmas in May, you sexist shit." Her brother started hyperventilating, just a bit. She grabbed the hateful candy cane-striped tights out of the box and thrust them at him. "Take off your clothes, and I mean all of them, just like I had to, put these on in your room, and then get your sad ass right back here."

"Can I start with that part too?" he asked quietly, pointing to the vest/petticoat, a white concoction from hell that looked like a little girl's dress all by itself. "Just so you don't see my dic-k?"

"Fine. You got it," she said, shoving it at him as well, and he retreated to his room to put them on.

She wondered if he was actually going to wear it. She half-expected him to come back, smirking, and go 'Did you seriously think I was going to?' She couldn't actually make him do it, and, at some level, he had to know that. Her mother would flip her wig if she saw this, and Zoe had seen enough cop videos to know that even if she were twice his size, she certainly couldn't have physically forced him to wear it. Besides, there really wasn't anything stopping him from ripping up what she'd given him or cutting or tearing the dress apart later when she wasn't looking. (She wouldn't have really minded that much if he did. She hated the thing, after all.) The only reason she had worn it was because Heather had threatened to take everything away from her if she didn't, and she burned with anger and humiliation at the thought and wished that she had torn it apart anyway, right in front of her mother's face.

But Richard did no such thing. Instead, he knocked on his sister's door, even more softly than last time, and when she told him to come in, he stood there, looking very demure and very nervous, with his candy-cane legs and his white petticoats. Maybe he'd felt sorry for her - she knew he hadn't known about that thing with that one cousin - or maybe he thought she'd go easy on him if he quietly complied. She didn't know and didn't care. She had the chance for revenge and was not going to waste it.

"What are you worried about?" she asked spitefully. "I mean, you might not be a girl - yet - but you should feel lucky you get to look pretty wearing this stuff! So let's get you in it, just like I was." She pulled out the dress itself, and took a second to marvel at how stupid, how insultingly ridiculous, it really was, and he submissively put up his hands so she could lower it onto him. The bulk of the dress was similar to a Christmas tree, with little bells taking the place of ornaments, but since they couldn't ring freely against the fabric, an entire line of bells had been sewn along the hem, so the wearer- HIM, now, would jingle everywhere HE went. She buttoned up the front, the buttons made of Santa heads, and the long sleeves matched the tights with their candy-cane stripes. She smirked as the somewhat stretchy velvet fit him almost perfectly, although not quite the same way as it had her. A pair of red mittens with white fur cuffs was threaded with a string through the sleeves, and she made sure that the string stayed in front of his chest just like it had hers. "Hands in mittens, and I don't care what you're doing, you keep them in there, just like I had to," she told him, knowing that he had only been a small part of the problem. She wanted to find a way to do something much worse to her mother. "Here's your Santa hat, don't let it fall off your head!" It was just like a regular Santa hat, only with a bell in place of the top pom, and she secured it firmly around his head. "And your boots, we really can't forget your boots, little sissy!" The boots were also red with white fur, with little bells hanging from the tops and three-inch heels with a small platform, and he passively tugged them on one at a time. She couldn't remember if she ever told her mother what she thought of the whole ensemble: that it made the wearer look like an eight-year-old whore.

She wasn't done with him, though, and moved her swivel chair to the vanity she got on that very unmerry Christmas. She'd never used the thing, and she grinned sardonically at the fact that he would be the first. He stumbled slightly in his boots as he sat down on the chair. She applied generous amounts of foundation and dark red lipstick - she'd never used it, she was surprised it hadn't totally dried out - and decided not to continue with more because she didn't want him to look gross. She wanted him to look cute. She pulled out her phone from her pocket - a thing his dress didn't have - and snapped a picture once she was done.

"Are you gonna blackmail me?" he asked in surprise, a lilt in his voice.

"Blackmail is when you threaten to send it. I am not threatening to send anything." She pushed a few buttons on her phone, uploading it to her private, four-person Discord chat. "There. Now The Squad knows." Zoe and her three closest friends had named themselves that, after the political counterpart, shortly after she had met them a few months ago.

"If Mom ever sees that, we're both in deep shit," he said nervously.

"She won't," Zoe said curtly. "We keep our secrets. No, that's just for us, to forever memorialize my little shithead brother as a pathetic sissyboy wearing the world's most girly Christmas dress in May." He pursed his lips and looked downwards, not wanting her to see his expression. He shifted on his seat a bit. "But you know who it's really for? It's for you, because this IS you. As much as you don't deserve them, you'll be back in your boy clothes after Mom gets home, but no matter what happens later, you will always be the little jingle boy who let his sister dress him up like a candy cane tree, for the rest of your life." She reveled in the pure catharsis, the sheer vindication of taking all the humiliation of the last two parties, that totally wasted Christmas and his shitty, friendless birthday party - those cousins were the only males there other than him - and throwing all of it straight onto him instead. There weren't any surviving pictures of her in that damn dress - a very fortunate glitch had deleted the entire album they were saved in, on all devices - but there would always be at least one picture of him. "Well, go on, Jingle Boy! The house isn't going to vacuum itself! Make sure you don't trip over your heels!" Taking uncertain steps in his fur-lined girly boots, he quietly, obediently, minced out of the room, bells tinkling, under Zoe's mocking glare. "Don't worry, there will be someone here playing your game, you don't need to anymore!" she called out as he jingled down one stairstep at a time.

She briefly felt that maybe she was being a bit too harsh, but that monstrosity was what had been done to her and what he'd clearly wanted to continue doing to her. If this wasn't the very definition of karmic justice, what was?

She put on her headphones and played two games, the hum of the vacuum cleaner a pleasant background buzz. The first game, she'd lost, but she wasn't familiar with the limited map and blamed it on that. The second game, she won, not entirely decisively, but enough to feel like she'd proved herself. She heard a light knock on the door just as she was mopping up, and with the biggest, smuggest expression on her face, she opened it.

There stood her little brother, holding the vacuum cleaner with his velvet mittens like the perfect little sissy housewife, pursing his painted lips. "Can I come in?" he asked in a timid, soft voice.

"Ask politely to do what you came here for, and I'll let you in."

"May I please clean your room, Zoe?" he quietly asked, looking at the ground and demurely holding the vacuum cleaner to himself.

"You certainly may. Don't even think about opening anything, and be careful with the cords."

She considered continuing to play while he worked, just to rub it in some more, but it was much more fun to sit in her swivelchair and watch him instead, her in T-shirt and jeans, headphones around her neck, and him in his stupid Christmas outfit. He actually did vacuum her room diligently, using the edging attachment for corners and even using the dusting attachment for other surfaces, slowly and delicately doing everything with the velvet mittens inhibiting his grip and making sure that his dress didn't brush against anything, his petticoats resting against his candy-cane legs as he got on his knees to reach under her bed, the bell on his Santa hat touching the frame. It was exhilarating to watch, and she took a couple more pictures of him doing his chores like the little maid he was. The only thing she regretted was that she couldn't hear the jingling of his bells over the noise of the vacuum cleaner.

Eventually, he finished, and started to jingle away. "Well?" Zoe asked abruptly, and Richard turned to her in confusion. "You asked politely to clean my room. What do you say now that you're done?"

"Thank you for letting me clean your room, Zoe," he meekly said, looking at the floor again.

"You're very welcome, Jingle Boy. Once you're done with the rest of the house, you can go do the laundry." She gestured to her full hamper, and he picked it up and walked out with it and the vacuum cleaner, taking short steps in his heels.

Feeling like the queen of everything, Zoe turned back to play another practice game before she went out into the big leagues, and got utterly crushed in both tactics and unit production. The other player was just that much better, she couldn't figure out what she had done wrong. Wasn't Very Hard supposed to be the equivalent of a really good human opponent, wasn't that what that meant? Who the hell were these people? She remembered that he had his own username and looked him up in the rankings, just to compare; if she was having this much trouble against initial human opponents, surely he was even worse. (It crossed her mind that this would have been a much smarter thing to do before she had challenged him.) She couldn't believe her eyes and thought she was misreading: he was in the Diamond league. Diamond, while she was having trouble winning in the practice maps. "What the hell!" she half-whispered, not understanding. All he said was that he could beat the computer on Harder! Had the little shit just gotten someone else to rank him up or what? That made even less sense.

She noticed that the vacuum cleaner had been turned off, and wondered if he'd finished with that particular task. She thought about how obedient and quiet he had been while she had dressed him, even while he had partially dressed himself, even while he had cleaned her room. Then she got to thinking about what, exactly, he had said on Christmas and what he had been staring at, during both Christmas and his birthday. And then she remembered whose idea this bet had been in the first place.


Jacqueline

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Re: A Bet to Lose
« Reply #1 on: May 20, 2020, 05:51:02 PM »
"Oh no, Br'er Fox, please, whatever you do, don't you ever throw me in that there briar patch," she said aloud, pissed at him and absolutely furious with herself for not realizing a whole lot of things, about Starcraft, about his behavior both previous and recent, about why he'd put on the petticoat so she wouldn't see the outline of his dic-k. He probably still had a throbbing erection. Closing the game in fury and tossing her headphones onto the desk, she got up from the computer and stomped downstairs, hearing a slight tinkle of bells from the laundry room. She threw open the door hard enough for it to bang against the springy rubber stop, and he jumped in surprise, bells tinkling again, and turned from his clothes sorting to face her, a sheepish look on his face. He knew she knew, and she knew he knew she knew, and he knew she knew he knew she knew.

"You lost on purpose," she accused him anyway. If she could have spat venom, she would have done it right then.

"I threw the game, yeah," he replied, in an ordinary voice totally bereft of all the timidity he'd shown - roleplayed - over the past hour. He'd felt lucky that his plan had worked at all and was hoping that she wouldn't figure it out so soon. The boots, while super cute, were a size too small and were pinching his feet, but he loved the sound his little bells made, loved the slippery-soft feel of his velvety mittens, loved the soft feeling of his dress and petticoats on his skin, loved how cute he was as he looked down at his pretty Christmas tree dress and childishly striped candy cane arms and legs, smiled every time he saw his made-up reflection anywhere, and enjoyed the thrill of doing chores while dressed like this in front of a girl, even if she was his sister. He'd even enjoyed the sensation of being dominated and mocked. He figured that she was certainly going to strip him of all of it now that she knew. At least it was nice while it lasted.

"You little pervert. You got your sister to fulfill your fantasy. I hope you're proud of yourself."

"You wanted to do it, too!" he replied. "You were enjoying doing it! If you didn't want to, why'd you take the bet?!"

"Yeah, because I thought you didn't want to be-" She stopped abruptly, not liking how it made her sound. 'I only wanted to put you in a humiliating dress because you didn't want to be in one' was something a Grade A bitch would say. Still, though... "I didn't know you were getting off on this! Your sex fantasy is of something that made me hurt, you know that, right?"

"I know YOU hate wearing it! That's why I deleted all the pictures Mom took on Christmas, because I knew you didn't want to see yourself like that again." He'd felt enormously guilty at the time, both for saying what he said and for secretly wanting to wear something that had actually, seriously, humiliated his big sister.

"Bullshit, she said she got an email from support," Zoe said, unsure. That had been an awfully convenient glitch...

"I deleted the whole album off the cloud, then her phone and computer, and then sent her a bogus support email with fake headers. I even had to fish it out of the spam folder myself and mark it unread. You'd know it was fake, but of course Mom believed it." Their mother, as she would be the first to admit, was generally incompetent with technology and had previously needed her children to avoid getting suc-kered; they'd even talked her out of sending money to a Nigerian prince a couple years ago. She had zero concept of computer security and wasn't good at keeping track of her phone. "I bet she still has it in her inbox somewhere." He looked at his sister, his heels putting his eye level somewhat above hers. "Think about it, a glitch deleting just one album from both her cloud and local storage on her phone and computer?"

"You would've been in so much trouble if she found out." Because their mother had some idea of just how susceptible she was to falsehoods, that was the kind of thing that would get him grounded, no computer, no TV, no games, no anything, for months. "You could have told me."

"You were really upset," he replied. "I didn't know what you'd do, I thought you might have told her because you were still pissed off at me for saying you were lucky, and then later I figured it'd just be safer, I guess, if you never knew." He took a deep breath, the velvet moving as he did. She knew his big, dirty secret and could already get him in deep trouble, so there wasn't much point in keeping more from her. "Also, after my birthday party, she wasn't the one taking the pictures so I couldn't delete those, but I told her that I'd saw some research saying that two-thirds of all lesbians.. um..." He tried to remember exactly what he'd made up. "'were excessively feminized by their mothers, including forced wearing of dresses and other female paraphernalia.'" Zoe's eyes widened somewhat. "You know she'll believe anything with big words in it. She probably thought that meant that there was a two-thirds chance you'd turn into a lesbian if she kept doing that to you. That's probably why she left us at home instead of dragging us to that stupid wedding, because you'd have to wear a dress if you went." Like most of the rest of their family, their mother was someone that some people would call 'traditionalist' and others would call 'homophobic'. Being convinced that her own actions were actually leading her daughter to become less feminine instead of more had changed her approach immediately.

"And why she's going to let me do whatever on my birthday. Ricky, I don't know whether I want to slap or kiss you, well definitely not kiss you, you're still a pervert, but... okay, I know your secret, now you're going to know mine, and you never tell anyone this." He nodded. "I'm bi. Bisexual. So when you told her that, you might have made her start looking for signs of it, and do you know what the hell she'll do if she ever finds out?" He fumbled for an answer. "You don't know. Neither do I. If you actually do care about me, you'll keep that secret and I mean secret. Also, why did you say all that shit about girls earlier?"

"All of that was just bait so you'd take the bet," he replied, holding his mittens up innocently. "I didn't mean a word, I swear."

She nodded. It really was unlike him to say things like that, especially given what he'd really meant on Christmas. "I sure did throw you right into that briar patch, Br'er Rabbit." Her expression softened a bit. He really was a tricky little bastard, but he'd only been tricking to help her avoid what she didn't want and get what he did. It was her mother who'd been hurting her out of some misguided ideals, and he'd put an end to that, at risk to himself and without even expecting any thanks. If, instead, he'd held real malice in his heart towards her, he would have stomped her in the game, although, she had to admit to herself, she probably would have welshed on the bet. She felt deep love towards her little brother, despite the fact that he was a colossal pervert; after all, a lot of people would call her sexuality perverted as well. She was actually relieved that she'd been playing to his fetish the whole time, as that was better than having actually hurt him. She felt a bit of swiftly dissipating guilt. She'd intended to punish him for hurting her and had actually rewarded him for helping her. No harm, no foul. "Hey, if my friends came over here and saw you like this in person, would you be okay with that? And I'm sorry about sending pictures without asking, that was a bitchy thing to do."

"It's okay, I was trying to piss you off," he reminded her. "And yeah, sure, as long as they don't do anything too weird."

"They won't," she assured him with a smile. "It's funny, because last week, we were talking about boys in dresses, and Susie said some kid's babysitter put him in some weird bondage dress thing and his twin sister almost blew the babysitter's head off."

He rolled his eyes. "Bullshit, video or it didn't happen."

"I said the same thing! Susie swears it's real, though." That was a reminder to check her phone, and the chat was lively, with all three of her friends gushing over how cute he was, and he smiled a bit as she let him read it. 'He lost on purpose', she texted to them, and the chat grew much livelier; she invited them over to watch a movie, and the chat grew livelier still. Then, abruptly, she threw her arm around her little brother and took a selfie with him, both of them smiling widely for the camera. Caroline abruptly stopped chatting; she was the only member of the Squad with a driver's license, and she'd just jumped into her car to pick the other two up as fast as she legally could. Zoe then noticed the piles of laundry Richard had made, and something was off. 'Gtg, see you when you get here,' she texted, and put her phone back into her pocket. "You're separating the laundry wrong."

"How, it's whites and colors, right?"

"Oh my God, I'm glad I came down here." He knew how to vacuum, but he did not know how to wash. "This house, it's regular whites, regular colors, delicates, and permanent press, and I'll show you what gets what." She went through and explained fabric labels, materials, and dyes, and he patiently listened in his sweet dress, trying not to jingle too much when she talked.

"Four loads, that's going to take a while," he noted at the end.

"Yeah, well, normally you're supposed to be doing other stuff at the same time," she pointed out. "But, huh. You did the dusting with the vacuuming, and I bet you don't want to get your dress or mittens dirty by doing the dishes or the toilet, do you?" He shook his head. "I bet you'd love mowing the lawn like that, wouldn't you?" He blushed deeply and looked away. "You really are a pervert." She smiled at him, shaking her head a bit. "We have days to do all that stuff anyway, and my friends will be here in like twenty minutes. Staying on those boots that long is bad anyway."

"Yeah, I think they're too small."

"Then we definitely have to get those off you. I know you love them, but that's really not good for you. And... I still kinda don't like how you did it, but thanks for getting Mom off my back, little bro."

He curtsied, placing one heeled foot in front of the other and pinching the sides of his dress with his mittens, making all the delicate little bells tinkle. "Thanks for dressing me up, big sis."


babycakes

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Re: A Bet to Lose
« Reply #2 on: May 22, 2020, 04:02:26 PM »
Even better story than "Like Father, Like Son", and ever more realistic.  Both your stories are like Aesop's Fables for this genre.  There always seems to be a little moral to the tale.  Bravo and thank you!

dolly bo peep

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Re: A Bet to Lose
« Reply #3 on: May 25, 2020, 10:22:57 AM »
Jacqueline,

I like this story and hope you plan to continue it.

I can't wait to read what Zoe's friends have in store for Richard.

Jacqueline

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Re: A Bet to Lose
« Reply #4 on: May 26, 2020, 12:55:26 AM »
After she helped pull off his boots, letting his tights-clad feet breathe and relax, Zoe and Richard talked until her friends got there. She'd asked him how long he'd been interested in such things, and he explained that he'd always wanted to do it, that he'd always wanted to try on dresses and look pretty, even though, as he carefully pointed out, he didn't actually want to be a girl. It was an erotic thing for him, but that wasn't entirely the reason. "This is why I never let you see what character I'm playing in some games," he added, and Zoe understood. She explained that she'd only become interested in girls recently, or maybe she just realized that she always was. Both of them stumbled over their words a lot, with awkward silences in between that were filled by Zoe's texting with her friends, and they were interrupted by a message on Zoe's phone telling her that the car had just pulled up. Richard pulled his boots back on and minced to the door to greet them.

Coming down the path were three girls. To Richard's left was a tall, well-developed blonde in a white t-shirt advertising a mechanic shop, jeans, and sneakers, and she had the sort of permanent grime that gave the impression of long experience with manual labor. To his right was a slightly, somewhat less-developed, brown-skinned girl with shiny, long black hair, wearing an expensive-looking purple shirt and skirt set with elegant flats. Unlike him, neither of them were wearing heels, which was just as well because the girl between them could never have worn them.

That girl looked to be about eleven or so, with red hair and a sea of freckles. Like the taller girl, she wore a shirt, jeans, and sneakers, but her jeans had bell bottoms and were obviously oversized to fit something under them. She walked like a frail, old woman, taking one careful step at a time, and Richard immediately realized that this girl had serious mobility problems and was walking between them so that she could be caught if she fell. Before they arrived, Richard had envisioned girls very similar to Zoe, of the same attributes and general height as her, with the same brown hair and blue eyes he and his sister shared. It hadn't really occurred to him that they might look completely different from her and each other, and it certainly hadn't even crossed his mind that one of them might be disabled.

"He is so cute, he is soooo cuuute!" the girl on the right squealed on seeing him as the middle girl smiled at him deeply, her mouth opening in sheer joy.

"Wowwww. I thought those were Photoshopped. He's actually wearing that, no, he actually WANTS to wear that. Holy shit, Zoe," the girl on the left said.

Zoe introduced them from left to right, and he jingle-curtsied to each in turn. "Richard, this is Caroline, who just turned seventeen, Leslie, fourteen and a half," Richard was surprised but understood at once: whatever disease had done that to her had also stolen her puberty. "Susie, fifteen and a half. Be careful, there's a step," she added.

"Zoe, I wet on the way here," Leslie said softly, as her friends gently, carefully moved her up the single step, a step that Richard had taken thousands of times without even thinking about it.

"Our only bathroom's upstairs," Zoe replied. "I'll get you in the kitchen." Richard saw that Zoe did some things with the braces on the girl's legs, lowering her onto the floor, and then he looked away.

"What's...?" Richard asked quietly.

"Duchenne muscular dystrophy," Caroline replied solemnly. "Very rare in girls, Leslie just happened to get unlucky. She's had it since she was nine. It hasn't hurt her brain, thank fuc-king God."

Richard took a breath. He was an intellectually gifted and unusually internet-savvy thirteen-year-old boy, and he thought of himself as as a true swimmer of the waves, having experienced all the sick and disturbing content that he could find just because he was thirteen years old and wasn't supposed to be looking at it. A small fraction of that was diaper fiction, some of which involved genuinely horrific scenarios. A few times, he'd been so disgusted with the story, and himself for reading it, that he'd stopped reading out of fetishy interest and continued out of pure morbid curiosity, simply because it was there and he wanted to see how bad it would get. For someone to actually inflict that kind of total, permanent helplessness on someone else would be unfathomable, Mengele-tier evil that couldn't be adequately described with the word 'sadism'. This disease had done that and more to a nine-year-old girl without giving her so much as a safeword.

"Totally incontinent?" he near-whispered. He knew it was bad manners to talk about her behind her back, but to say this stuff out loud was unthinkable.

"She lost bowel control earlier this year," Caroline said quietly. "The urine's bad enough." There was silence, for a bit, as Zoe applied wet wipes and powder.

"You're already wearing a dress, do you want to know what this is like?" Susie softly asked, straight-out. "Personally?"

The Christmas dress was still just clothes that his sister had been threatened into wearing only once; the idea of fetishizing part of someone's actual disability, in person, was appalling and disturbing. "Wouldn't that be making fun of her?" he whispered.

"Let's ask her," Susie replied as Leslie and his sister came back from the kitchen. "Hey, Leslie, Ricky wants to know if it's okay for you two to be diaper buddies," she said blithely, and Richard stared at her in surprise.

She smiled at him. "Sure, I'd like that," she replied in her weak voice.

"Just so you know, Ricky, I did this for a week," Zoe added. He went from staring at Susie to staring at her - his sister was in diapers for a week, and he never knew?! "It was gross and terrible even though I changed myself, I wouldn't wish it on anybody, and I was worried that you or Mom would find out," she continued, to his shock. "And in case you didn't know, I've been putting absorbent stuff in my pants for a few days every month for almost a year now." At first, he didn't know what she was talking about, and then abruptly he did.

"You keep dressing like that, and you'll learn more about that last part," Caroline teased him.

"I'm not really a girl, and I'm not gonna be," he said, and his slightly pouting, made-up face garnered light giggles, particularly from Leslie. "Leslie... will this actually help you?"

"I just want the people I'm with to know what it's like," she said. "Just a little part of it. You can stop whenever." There was a very faint trace of bitterness. Her friends got to stop wearing diapers whenever. She did not.

"I'll do it until Mom gets back," he agreed. "She'll probably find out if it's me doing it near her, and if she finds out about this, any of this at all, it's gonna be..." He looked to the girls, trying to think of suitable words. "Catastrophically, cataclysmically, grounded-forever bad." He tried to put his finger across his throat in the cartoon throat-cutting gesture, but he was still wearing his mittens so it just looked silly.

"Then we should make the most of the time we have," Caroline said. "Do a twirl for us." Richard did so, spinning his dress around while turning on his heels, and although he was sure he didn't do it properly, the girls clapped anyway. "This isn't even embarrassing for you, is it?" she asked.

"It's not. If other things were different, it totally would be, but it's not."

"Good, because unlike what your" Caroline did not really say the words 'crazy-ass', but Richard heard them. "mom did to Zoe, we are not going to humiliate you in public. But what we are going to do, is, well, Susie?"

"We're going shopping," she said as the washer dinged.

"Perfect timing. Ricky, go put the clothes in the dryer, but don't put another load in the washer, we don't want the clothes to mildew," Zoe told him.

He could have said no, that any going out in public dressed like a girl at all was actually humiliation, that this was seriously going way too far, and Zoe's friends would have accepted that because they were people, not monsters. Instead, jingling to their amusement, he minced off to put the wet laundry into the dryer like his sister had told him to.

Since all he was doing was moving clothes from one machine into another, even with his mittens, it didn't take him that long, so he returned to the living room as Zoe came back down with clothes, both his and hers. He stood off to the side, enjoying the thrill of letting them pick for him. Leslie, he noted, was making the decisions, and he was surprised at them. His sister's shoes were too small for him, so he'd wear his white sneakers and a somewhat skinny pair of his jeans that he usually eschewed. He'd also be wearing one of his sister's shirts, a pink one embroidered with blue waves, that he'd never seen her actually wear. A pink ponytail placed on top of his head and a change of makeup, turning the red lips into something more subtle, completed the effect. Leslie had been spot-on with her choices; in the mirror, he saw nothing but a modestly dressed girl a bit younger than himself, somewhat tall in stature but who hadn't yet hit puberty and wasn't trying to be super girly.

"You get shotgun," Caroline told him as they walked out together, the others helping Leslie down the step. "You're the broadest of all of them, and Leslie needs room." The front seat was definitely comfortable, and he realized that he wasn't worried at all about being seen.

"Speaking of which," Susie said as they got into the back seat, "No, wait, first, Zoe, did you tell him Rule 1?"

"I didn't, I figured you should," Zoe replied.

"Okay. Richard, Rule 1 of being my friend is that you cannot talk to me about money. At all. You cannot ask for it, you cannot ask for anything gained with it, you cannot so much as mention it. This rule is absolute. I have lost so many friends over this stuff and I don't want to lose more."

"I understand," Richard said. He didn't just understand the rule, he understood why it existed. He got the impression, just looking at her, that she was very, very rich. If he were very, very rich, he would probably have a similar rule to keep moochers away from him.

"Okay, I have heard from a trusted friend that a babysitter tried to sissify a ten-year-old with a bondage dress and his twin sister grabbed a shotgun and almost blew the babysitter's head off with it. Do you believe this happened?"

"I don't. It's not that I think you're lying, I just really doubt whoever told you about it," Richard explained. "And I know there's weird real stuff out there, I've seen some of it online." That was an understatement. He had seen very real human monsters, even had one on his Discord friends list, because he had gone looking for them. Knowing that such things existed made being seen in girls' clothes seem much less frightening.

"Right, fine, I'll see if I can get better proof," Susie replied, shrugging. "Maybe you all are right, maybe she really is BS-ing me." She shifted the conversation over to what Zoe has asked him, how long he had worn dresses and how long he had wanted to wear them, and he found the questions only somewhat easier to answer the second time around.

"There's the store," Susie pointed out after a while. The store she pointed to was a thrift store festooned with Memorial Day advertisements and promises of discounts on already cheap stuff. The store had just reopened after the outbreak. No one asked why she picked a thrift store; to do so would be to indirectly violate Rule 1. "It's all luck. You can find nothing or you can find everything," she explained anyway. "But since they've been getting donations they can't sell for the last couple of months, it's probably more everything than nothing."

Caroline parked and Richard did not hesitate in stepping out. This was his first time outside in girls' clothes, but he knew that no one was looking nor cared, nor would they, not when Leslie would catch far more attention with her limping, elderly movements. (It briefly crossed Richard's mind that the actual elderly didn't deserve this any more than she did.)

"Okay, everybody, if you see something you like, go ahead and grab it," Susie said. "Just don't go crazy." This was the flipside of Rule 1. Her friends weren't allowed to question her generosity any more than they were allowed to ask for it.

Zoe went with Leslie, staying close to the disabled girl and letting her pick out anything she thought would be nice for either of them. Caroline simply browsed, looking for knick-knacks rather than clothes. Richard actually took the opportunity to snag some ordinary boy clothes he liked; people would have noticed a boy in the girls' section, but nobody noticed an ostensible girl in the boys' section.

Susie went through the racks of girls' clothes, but she was more interested in the back room, a place of still-bagged clothes that had not yet been processed, and that was where she hit the jackpot. A baby pink, knee-length dress with puffed sleeves and built-in petticoats, a pair of rainbow scrunchies, a pair of pink ruffled socks, and a pair of shiny Mary Janes with one and a half-inch heels were all in the same bag, which was labeled "Donation from GAS". (She chuckled at the acronym but had no idea what it could have possibly stood for.) Excited, she motioned Richard back there to try the shoes on, and they fit perfectly. She squealed in delight. She held the dress against him, and as it was at least approximately his size, she decided to buy it; if it didn't fit, she'd alter it herself. The place was an absolute treasure trove, even better than she'd hoped. She also selected a pair of Santa boots with four-inch heels that also fit him fairly well - they both laughed at the idea that he'd grow into them - another pair of pink, four-inch heels, a pair of wedge sneakers with two-inch heels, and multiple dresses in varying colors and lengths, along with a bright pink purse and a childish pink backpack with sparkling rhinestones.

By the time she was done picking out stuff, the others had been ready for a while, and she paid for them all without question. This was a thrift store offering discounts, so the price for all of it combined was fifty-something; she reached into her well-stocked billfold in her well-stocked purse, handed three twenties to the elderly cashier, and told her to keep the change, to her surprise and thanks. The place was owned by a local charity that had been hit hard by the pandemic, after all. Susie's face was a beacon of pure glee as they walked out with their bags.

They very briefly stopped at a craft store. Susie went in alone and came back out in three minutes. "It's a surprise," she said.

Their next stop was a gas station; Caroline went in to pay with the twenties that Susie simply handed her, and she came back to the car with cups of crappy gas station hot chocolate and small, unhealthy snacks. Between sips, she talked about the last time she worked on her car and what her father had taught her about transmissions. Richard noticed that it was kind of odd listening to a girl talk about cars, but it was probably less odd than a boy in a dress, and she was kind enough to strictly avoid obvious, contextual 'tranny' jokes.

Their next destination was a grocery store, and on the way, they realized that Richard used Discord but wasn't in their group for some reason, and the Squad was then formally a group of five. "I don't think I can walk all this. You don't need to bring me." Leslie said as Caroline parked.

"If you're staying, I'm staying," Zoe said firmly. "You know that."

Caroline popped open the trunk to retrieve a wheelchair, and her voice was a combination of calm and firm. "Leslie, we've been over this. You are not a burden, and you are not a liability. Do you actually want to sit in here by yourself while the rest of us go in there?" She shook her head. "Then c'mon out." She did, and the other girls helped her into the chair. Richard would have helped, except he had no idea how her leg braces worked.

"If you want me to, I'll push," he offered.

"It's okay, Ricky, Zoe's good for this stuff," Leslie said, smiling fondly, and they walked in together. Richard realized, then, that they had made him one of them. He wasn't a circus freak, he wasn't a plaything or a doll to them, he was someone they actually cared about. He was a boy, and they all knew he was a boy, and although they were pretending otherwise to the public, they weren't pretending among themselves. They had welcomed him, not humiliated him, for what he was. He had a group of friends, one he had never had, one he never knew he wanted. He realized that he would have done anything reasonable, as well as a great many unreasonable things, if they had so much as asked. He was expecting them to want to parade him around in frills and lace, and instead, he was walking around like a modestly dressed girl, all the attention on the girl in the wheelchair that his sister was pushing in the grocery store.

This destination was actually Caroline's gift to Susie than the other way around, as she was primarily shopping for herself, selecting ingredients for recipes only she knew. As before, the others bought lightly. Caroline's family had plenty at home already, for Leslie, it was more about what she could and should eat than what she wanted to eat, and Zoe made a point of picking up the burritos that both she and her brother found tasty and easy to make. Susie paid for everything, again, and this time Richard was used to it.

That was all; the group was basically done for the day. Leslie had to get home and take her pills, and Caroline also had to be home fairly soon. "Hey, Ricky, want to spend some more time at my place? You live less than a mile from me," Susie told him to his surprise.

"You want to say yes, believe me," his sister advised.

"She's got a massive crush on you," Leslie told him, and Susie turned to her in exaggerated shock. She wasn't supposed to just blurt that out!

"Okay, you've talked me into it," he said, and they all laughed. Leslie's home was, as expected, on one floor with no steps, and Richard stayed in the car as Zoe pushed Leslie to her door. Her parents thanked Zoe, as Richard was sure they always did, for being so good to her.

Jacqueline

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Re: A Bet to Lose
« Reply #5 on: May 26, 2020, 01:04:09 AM »
They drove back mostly the way they came. Richard's home was in the less expensive part of a fairly large suburban area on and around a hill, with property values and lawn sizes generally growing with height, right up towards a cul-de-sac with one particularly large house, practically a mansion, at the peak. He'd always wondered who owned this enormous house at the top of the hill, and now he knew.

She had the pink backpack, but he did carry in more bags than she did; he was, after all, still a boy. He tried not to stare at the high ceiling, the unimaginably expensive rug, or anything else in the lavishly furnished house; he was actually grateful for Rule 1, as he would have felt compelled to compliment her without it. A small, orange tabby meowed loudly as they entered, the cat wrapping itself around his legs as he set the groceries down next to the large refrigerator.

"Whiskers, I know he smells good, but you're going to get stepped on if you keep getting in the way," Susie told her cat affectionately, and Richard pet the tom anyway.

"I didn't see you get any cat food," he noted.

"Cat food? Whiskers does not eat 'cat food', he eats food. Not always the same food, but still food. I'm not giving you a can or a bag of 'people food' for dinner, am I?"

"Oh, okay. We're having dinner?"

"After we put this stuff away, cooking dinner is the third thing we're doing today," she told him. "The second thing is that we're dressing you up. The first thing is that I'm going to teach you the basics of sewing."

He didn't understand what she meant, but once she pulled what she'd bought at the craft store out of her purse, she did. All that she'd purchased was a one-dozen pack of small bells. She pulled the baby pink dress and ruffled socks from the pink backpack, and he learned how to thread a needle - a tricky thing - and how to precisely sew small things without the thread coming loose or falling off. Once they were finished, his prissy pink dress and pink ruffled socks were now a jingly, prissy pink dress, bells positioned equally apart from each other at the hem, and jingly, pink ruffled socks, two bells on each side. She couldn't wait to dress him up in it, and dress he did, his ponytail replaced by the rainbow scrunchies she'd gotten him, his ruffled-sock feet buckled into his shiny Mary Janes. A blissful, content smile reached his face, and it stayed there as he packed his other clothes into the pink backpack; he didn't believe in a heaven, and even if he did, it couldn't have been better than this. She kissed him, right on his nose. "You are so, so cute," she said. "If we had time, I'd have you dance for me like a ballerina. But it's dinnertime, and this is going to take a long time. C'mon." She led him by the hand into the kitchen, and when he walked on tile rather than carpet, he found that his Mary Janes made little ticking sounds in addition to the tinkling of all his bells.

They were making zereshk polom, a name Richard couldn't pronounce, let alone spell. It was a very involved recipe, and Susie bit back a curse when she heard her father's incoming ringtone. "Do not let the rice burn," she told Richard, picking up the phone.

"Hi Dad, I'm in the middle of cooking something," she said immediately. She turned up the speaker so that Richard could hear the other end of the conversation.

"Hey, sweetie." The man's voice was subtly foreign, but there was no true accent at all. "Just checking to make sure that you're doing okay, that you haven't done anything too wild, or brought any boys over, anything like that." There was a smile in his voice, and Richard knew that he was calling just because he wanted to hear her voice.

"Daaaad!" Susie said, affectionately brattish. "Other than Fatima, the only person who's been in the house since you called literally wears a dress," she said, perfectly truthfully.

"Is she there now?" he asked.

"Nope, she's not," she replied, again being technically truthful.

"Okay, honey. Take care. Be careful with the stove. Love you."

"Love you too, Dad." She hung up, and then both she and Richard started breaking up laughing. "What, I didn't lie to him!" They shared laughter some more before continuing to cook.

"Who's Fatima?" Richard asked.

"My aunt, she comes here every morning, early, to check up on stuff," Susie said. "I think my dad's just scared that I'll throw a party that'll trash the place."

He laughed. "Yeah, because that's totally the thing that he should be worried about, right?"

"Don't you laugh, mister," she said in a fake, motherly voice. "You did something bad today, and for that, you must be punished, but we will deal with this after dinner."

"Okay," he quietly, demurely replied. He hoped it wasn't anything to do with how he'd treated Leslie. He'd never had to personally interact with someone that disabled before, and it had been incredibly awkward.

They finished the rest of the convoluted recipe, using techniques that Richard had never seen anyone use on his mother's favorite cooking shows, and although the final result smelled unlike anything he had eaten before - he had never even heard of a barberry before, let alone tasted one - it was, as promised, absolutely delicious as they sat at the family's expansive table, right next to each other, occasionally feeding each other small bites. Even Whiskers seemed to enjoy it. "So, um... what do you think I should be punished for?" he asked once they were finished.

"You tricked your sister to put you in a dress," she said in that affected, matronly tone, "and that was a very naughty thing to do." She marched into the kitchen and picked out a plastic spatula. "Over my knee, sissy." Richard meekly obeyed, laying over her on her expansive couch, and she pushed his dress and petticoats up, exposing his diapered rear to the air. "If you actually, really want me to stop," she added, quietly and seriously, "say the word 'boondoggle'. That's the safeword, just in case something bad happens."

"Okay," he agreed, not wanting to tell her that he already knew what a safeword was.

What she wanted to deliver was stinging slaps that would fade quickly; what she didn't want was to hit him with any real force. After a few experimental, light whacks on each petticoat-framed butt cheek, she found that holding the spatula lightly in her hand let her whip it quickly but gently, producing loud, sharp sounds and reddening his butt nicely. He yelped childishly on each strike, fully in character, as she alternated between cheeks for a dozen times, but even through his diaper, there was no hiding the fact that being dressed up, lovingly dominated, and spanked by this beautiful young princess was turning his dic-k into a tree trunk. And then the spatula slipped a bit, making a quarter rotation in her hand, and she wound up striking him harder than she intended and with the little serrations on the edge rather than the flat.

"Boondoggle! Boondoggle!"

"I'm so sorry, I'm so, so sorry!" she shrieked, dropping the spatula, wincing, and inwardly cursing herself for being so stupid. "Hold still, just let me take a look. Okay, it's just red, there's no bruise or anything. I didn't mean to hit you with the edge!"

He smiled, making himself relax. She hadn't hurt him all that badly and he doubted she even could. "It's okay. I'm sure you'll get a lot more practice," he told her, promising many more sessions just like this one in the future, and that promise triggered her lust. She had the perfect boy of her dreams and she wanted him. She wanted him forever.

"Turn over," she told him, "and I'll make it up to you."

He turned over, and she pushed him along the couch, put her head under his petticoats, pulled down his diaper just a bit, and spent five minutes making it up to him by giving him his very first experience of that kind, using a tried-and-true method of preventing anything from spilling. It crossed his mind that she, being two and a half years his senior, was technically using him to fulfill her own desires. He very deeply wanted to be used just like that, over and over again.

She kissed him when she was finished, and what he tasted on her lips was himself. "You can't stay overnight because of my aunt, so unless you want to walk home in the dark..." Even with the long, near-solstice days, it was getting late.

"Okay, I'm going," he said, and gave her a very deep and heartfelt hug, his chin on his shoulder and her chin on his puffed sleeve. He got up, picked up his cute backpack, and put it on.

"Aren't you forgetting something?!" she asked him as he walked to the door, his bells jingling.

"No, I'm pretty sure I've got everything," he replied. He'd been careful to pack it all.

She stared at him. "What about your clothes?!"

"They're all in here," he said, smiling and patting his glittery pink backpack. "See you tomorrow, Susie!" And then, with his urges so very happily satisfied and his spanked butt still feeling a little sore from where she'd messed up, he waved and started skipping down the hill as she stood at the door, still staring at him.

Of course, she'd expected him to go out the way he'd come in, walking home as a basically ordinary-looking girl. Heck, he was a boy, and it was getting into summer; if he'd wanted to, he could have washed off his face, pulled the scrunchies out of his hair, thrown away the diaper, and gone out bare-chested and commando in just his boys' pants and shoes, leaving absolutely all the girly stuff in the backpack to be picked up later.

But why would he have ever wanted to go out with a bare face and loose hair when he got to wear makeup and his hair in pretty pigtails with rainbow scrunchies? Why would he have chosen to wear ordinary boys' or girls' clothes when he had a pretty, jingly, baby pink dress that showed the whole world what a cutie he was? Why would he have ever chosen a plain, dark backpack when he could wear a really cute, bright pink one with rhinestones that sparkled in the evening sun? Why would he need pockets when he had his bright pink purse to carry his phone in? Why would he have decided to run or walk in his boys' socks and shoes when he could skip down the sidewalk in his ruffled, jingly, pink socks and cute, clicky Mary Janes?

The question wasn't who would let him. The question was, who would stop him?

He realized he had to pee. He'd been in various states of arousal all day, but now that Susie had so generously taken care of that, he felt his bladder pressing. He could have waited until he got home, but he chose to flood his diaper instead and continued skipping along in his pretty dress and wet diaper, just because he could. He got tired of skipping after a while, so he decided to take dainty little steps instead, not because the low heels on his Mary Janes were making him but because he felt cuter doing it.

He went down a bike path between some houses. A couple of kids were bouncing on a trampoline; they yelled hi to him, and he happily waved hello back. An old man walking his dog passed him, and the man was clearly trying not to stare at the pretty thing skipping past him, who smiled and waved at both him and his doggy. (He'd wanted to say something as well, but his voice would have given him away.) There was a shortcut down a dirt path, but he didn't want to get any of his pretty clothes dirty, so he kept going down sidewalks and on paved paths, where everyone could look out their windows and see him jingling along.

He had to poop, so he squatted down, pretending to be looking at something in the nearby tree grove, and went in his diaper. (He somewhat regretted that. The squishy poop brushed against his butt afterwards and it was actually kind of gross.)

It took fifteen minutes for him to make it home while skipping along and taking dainty steps, and he hadn't even made it to the door before she opened it. He'd fantasized that maybe Zoe would tell him to do a little twirl or something before she let him in, but instead, she immediately gestured for him to get in there right away, closing the door immediately once he did.

"Oh my God. She was serious. You actually did that," she said with a combination of amazement, disbelief, and quite a bit of respect. To force him to do that would have been raw, unforgivable cruelty; for him to willingly dress like that much of a sissy in public, ironically, took massive brass balls. "What if some creep was out there?"

He shrugged. "The bait's too obvious. I mean, if you saw someone else skipping out there dressed like this, would you think that you happened to see someone wearing this out there all alone, or that it was some kind of dare, or benefit thing, or ad campaign, publicity, whatever, and someone was already watching? A real creep would want to come after me in regular clothes, but he'd be a really dumb creep to do anything with me wearing this."

"Okay, but what if one of our neighbors tells Mom?"

"I didn't see any of them looking, and when's the last time you saw Mom talk to any of the neighbors?"

She exhaled. "I swear, you are just the most incredible..." she started but couldn't finish. "I put a nightie on your bed if you want it, you just wear whatever until tomorrow." She suspected, correctly, that he would choose to spend the rest of his day in his pretty dress.

"Can you change me first, please?"

"Change... oh. Okay, Diaper Buddy." She knew she'd be the one doing this sooner or later. She used one of the diapers in his backpack to change him in the kitchen where she'd changed Leslie, using a generous amount of wet wipes and powder. At least he didn't have a hard-on, and she probably would have noped out if he did. "I think you should change Leslie next time," she said.

"Why?"

"You're only seeing half the problem, being changed yourself. It's not just her that's affected by that. It's everyone who takes care of her, everyone who spends time with her."

A suspicion became a certainty. "When you said you were bi, did you mean with her?"

She tilted her head skyward. "God damn, Ricky, you are just... Yes. And before you ask anything else, what my girlfriend and I do and how we do it is none of your business. And you tell no one about this, and I mean no one, not even Caroline or Susie."

"If I figured it out, I'm pretty sure they already know," he said. "They obviously don't hate boys in dresses, I don't know why you'd think they hate lesbians. I thought you said no secrets? Caroline's not going to hurt you, Susie sure as hell isn't." He was as certain as any teenage boy could be that she was as desperately in love with him as he was with her.

"Friendships don't always last, and if Mom finds out... God, the things you did today, we did..." She suddenly felt a wave of fear and regret.

"Your friends aren't gonna tell her, and who else would?" Richard felt particularly confident just then. Maybe it was euphoria from his adventure, maybe an ironic wave of testosterone from what Susie had did with him. He didn't care. Wearing his dress made him feel like more of a whole person than he'd ever felt in his life. Earlier, he had been worried that his mother would ground them forever; after what he had done that day, he didn't. "If she tries something really crazy, I'm pretty sure I can stop it. She's not a monster, she's just stupid."

"I just hope you're right." She finished taping him up and patted his thigh gently. "And by the way, I know that not everything in that diaper was pee or poop."

"What my girlfriend and I do and how we do it is none of your business," he replied with a smirk, and then she started laughing, and he started laughing, and she walked away with her palm in her face.

He played three games of online Starcraft 2, and, even in his advanced league, only one of the opponents gave him any challenge at all. He wondered what they'd say if they knew that they'd gotten trounced by a thirteen-year-old boy in a jingly, frilly dress. (Then again, he mused, they could also be thirteen-year-old boys in frilly dresses. This was, after all, the internet.)

He carefully took off his pretty clothes, put on the soft, silky nightie his sister had left for him, and cuddled under the covers for the best sleep he'd ever had.

dolly bo peep

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Re: A Bet to Lose
« Reply #6 on: May 27, 2020, 09:39:12 AM »
Jacqueline,

Wow! What chapters! They addressed a number of my fantasies.

I started reading your latest sections right after I woke up while I was still wearing my nighttime diaper, which was filled near capacity, and had to change into a fresh one before I finished.

I'm really looking forward to your future chapters.




 

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