Sweet Boy

“Uncle Drew! Look, I got a unicorn!”

Drew grinned at his niece through the camera. “That’s the prettiest unicorn I’ve ever seen Kenny! It’s almost as pretty as you.”

Kendra grinned back, sassily flipping the pink hair of the wig she’d picked to wear that day. Drew made sure she’d gotten dozens of wigs to pick from the minute she started losing her hair from the cancer treatments. “That’s cause I’m amazing!”

“Yes you are!” He wished he could hug the girl, could be there for her through all of this, but he knew his sister had everything under control at least. “Hey, can I talk with your mom for a bit Kenny?”

“Okay Uncle Drew.”

There was some movement and sounds from the phone, and soon he was looking at his sister’s face. “Hey Drew. Thank you for sending that money-”

Drew quickly cut her off with a shake of his head. “Don’t even mention it Al. I mean it. I’ll do anything I can to help Kenny out. So, have they gotten back to you with the test results?”

“Not yet. It’s driving me crazy. I know everything should be just fine, and she should be in remission now, but there’s always that chance-”

“Not with Kenny. She’s strong, a fighter. If anyone can beat it she can.”

His sister smiled at his confidence, though Drew could tell she was tired. “I wish you could have been there with us Drew.”

“Al-”

“I know why you can’t, I understand better than anyone else, but I still wish you could be there for her.”

Drew felt the familiar guilt that hit every time he talked with his sister, with anyone really. “I know Al. Look, I’ve got to go get some work done, okay? Tell Kenny I love her, and let me know as soon as you get the all clear.”

“Okay Drew, I will.”

Once the phone went black Drew sat in silence, simply staring at the little machine as he tried to imagine another life, a life where he could have been there for his family, where he could actually go out there and actually live. Finally he shoved the phone into his pocket before heading to his walk in closet to figure out what to wear for the day’s video. He hesitated at the sight of the dresses and skirts some of his fans had sent him, before grabbing a pair of shorts and an oversized hoody with bunny ears. Knee high socks and bunny slippers finished the look nicely, and Drew grinned as he studied himself in the mirror. He took a moment to put on some lip gloss and the tiniest bit of mascara, though he ignored the rest of his growing makeup collection, just as he did the dresses and skirts.

Once he was sure he was ready he went to the second bedroom, where everything seemed to be pastel or pink or frilly. Even his computer was pink and white. It was amazing how quickly everything had changed in the two years since they found out Kendra had cancer. Drew had done okay before that, making enough money with his streaming to pay his bills and keep up the maintenance on the little two bedroom house he’d inherited from their parents. It wasn’t like he had a lot of expenses really, just his computer system, bills, and his grocery delivery.

The day Allison told him about his niece’s cancer everything had started to change. Drew had started an OnlyFans, determined to do everything he could to help his sister pay for Kendra’s treatments. What he hadn’t expected was a growing collection of fans who had decided he was cute, and encouraged him to grow out his hair, to embrace the pastel colors that actually suited him so well, and to start exploring his feminine side, something he’d never been brave enough to explore on his own. Drew was surprised at how much he’d been enjoying his new style, and often wished he could get up the nerve to wear the dresses, but just like with leaving the house, it was just more than he could force himself to do. He was a coward, but at least he was a coward who had done enough to keep his sister out of debt.

Drew shook his head to clear the worries and stress away before turning his attention to the computer and logging into his Only Fans to start up a stream. “Hello everyone! I hope you are all having just as wonderful of a day as I am. Now, let’s see what we’re going to do today.”

Back before he’d started the Only Fans he’d found that it really didn’t matter, as his fans mostly just wanted to interact with him. If anything they encouraged him to do more than just game in his videos, and Drew had finally settled on a randomizer to decide. They were up to half a dozen items, though he knew his viewers enjoyed some more than others. Gaming was one they didn’t actually tip for as much as the others, though they did seem to enjoy the cross stitching hobby Drew had picked up, and he was currently working on a unicorn for Kendra. There was also painting or baking, though Drew was truly terrible at baking, something his fans didn’t seem to mind at all, as long as they got to watch him try.

Finally there were the fan’s two favorites, reading stories off reddit, and, well, it was OnlyFans, and the fans he’d gained there were always pushing for as much as he’d give them. Drew had never been brave enough to do more than rub himself off through the panties his viewers sent him, but it always got him the most tips, and he’d even found that his fans would pay for him to ship the soiled panties to them. It wasn’t something he’d have ever done if it weren’t for Kenny’s cancer, but he was willing to do almost anything to keep her safe.

The wheel spun for a while, finally settling on baking, and Drew made a little face at the sight. “Okay, so baking today, which means we get to spend time in the kitchen! I want to try and make bread again. I’ve had this silly sourdough starter I’ve been feeding for weeks now, and every time I’ve tried to use it I can’t get it to taste good.” He stood before leaning forward to the camera and blowing them a quick kiss. “I’ll see you in the kitchen in just a minute.”

Drew didn’t have to grab a laptop or camera, he had wired everything in his house for recording except his bedroom and the bathrooms, though he had been considering adding the master bathroom off his main recording room. He was the only one in the house, and didn’t have any pets, so they were on a motion sensor, allowing his fans to follow his movements without Drew having to do a thing. He even had monitors that connected to his computer in key places, one in the living room beside his television in case he played a game out there, one on the kitchen counter, and one in the little hallway. None of the other rooms were done up as much as his studio, but he’d slowly been bringing in more and more pastels and pinks throughout the entire house.

Once he got to the kitchen Drew smiled at the camera and gave a little wave before setting his attention to trying to follow the bread recipe while also entertaining his fans. Multitasking had never been his strong point, and at one point he tried pouring a cup of potato flour into the mixing bowl while his kitchen aid was on and mixing the other ingredients he’d already added. The powder hit the spinning paddle, sending the flour flying everywhere and dousing him in white as he squealed in surprise. Once the mini explosion came to an end he turned off the mixer, staring at the camera in shock for a few moments before shaking his head. “Well, I guess today isn’t the day we finally get this figured out.”

Drew grabbed his hand towel, trying to wipe the flour off of his face, though he only succeeded in smearing it around. “Thank you for the tips. You all are so kind.” A small sigh of disappointment escaped Drew as he looked over the kitchen, but he patiently grabbed a container of wipes to start cleaning up the mess. “I’m not really sure how much of the potato flour made it into the mix. Do I just add another cup or give up for today and try again?”

Replies chimed in, along with a few more tips as he looked over the responses, reading a few off and joking with the invisible strangers. It wasn’t really fair, how easy it was to talk and even flirt with so many strangers over the internet when he couldn’t even hug his niece or have a conversation with his sister face to face. Drew wasn’t sure how it started, but even as a kid he’d always preferred playing inside and had struggled to make friends. His sister wasn’t much help, since she was ten years older than him, with no interest in playing with her baby brother. As he grew up it got worse and worse, until his mother finally decided to home school him through high-school so he stopped having daily panic attacks. They’d tried therapy a few times, both when he was a kid, and even once he’d become an adult, but leaving the house kept getting harder and harder as everyone seemed to judge him every time he did manage to go out.

His parents died in a car accident shortly after he’d graduated high-school, and he’d hardly left the house in the four years since. Luckily his parents had gotten Allison a home of her own as a wedding gift, back before her husband’s cancer took him while Kendra was just a baby, and when they died he didn’t have to move, he just had to figure out how to pay the bills. There had been a couple years where he hadn’t actually had a real conversation with someone, just the little mostly one way conversations with his fans. That changed when his sister called him with the worst news ever, a call that changed his life.

Drew gave a little shake of his head, accidentally sending more flour flying about as he tried to shake away the memories. “I’m sorry everyone. I think I’m going to have to call it here for today, but I’ll be on at the same time tomorrow, and remember, I’m auctioning off a one on one cam session with one lucky fan!” Those always seemed to go well, though Drew tried to limit it to once a month. His fans had never been upset with their purchase however, always praising how well Drew took direction as they told him how to play with himself. There were limits as to what they could ask him to do of course, but his viewers were respectful of Drew’s limits, only pushing him at the speed he was willing to go.

Once he’d shut off the stream Drew took the time to properly clean the kitchen, then take a shower to get the flour out of his hair. He was just stepping out when he heard his phone ringing and quickly ran to answer it. “Al! I take it you got some good news.”

He saw her tears just as she answered with a sob, his heart instantly dropping to the pit of his stomach. “Al-”

“It’s gotten worse Drew!”

Drew shook his head, tears springing to his own eyes. “That’s not possible! She’s done chemo five times now!”

“They said it isn’t helping her.”

“So what will help her?”

Al shook her head again. “They don’t have anything. The doctors said there’s an experimental treatment, but there’s no way our insurance would cover something like that. They didn’t even want to sign her up for the last round of chemo!”

“They can’t do that!”

“Of course they can Drew! They don’t give a fuck about her. She’s just numbers to them.”

“How much is the treatment?”

“Eighty thousand, and that’s if it works right away with no complications.” She shook her head. “I already put a second lien on our house. I can’t even sell to get that kind of money.”

Drew could, he knew his house was worth it, that he could sell it or even get a loan against it, but there was so much that could go wrong if he couldn’t afford the payments, and interest rates were crazy. Still, it was for Kenny. Drew may not have ever met the girl in person, but he was willing to do almost anything to keep that happy little girl going. “I’ll get the money Al. Sign her up for the treatment. I’ll pay for it.”

“Drew-”

“No arguments. I’ll get it into your account as soon as possible.”

“Thank you Drew. Thank you so much.”

Drew politely said his goodbyes before turning his attention to finding out how to take out a loan with a lien on his home. The interest rates were horrible, and his job and credit certainly didn’t help, but after three days of work Drew was able to deposit the money into his sister’s account, instantly earning himself dozens of heart emojies in response. He smiled at the sight, though it wasn’t enough to wash away the worry. What if it wasn’t enough? What if they needed more treatment? Drew needed to make more money, a lot more money. His gaze flicked to the closet, and he finally sighed before pulling out a pink skirt and matching tank top. He had to do whatever it took to help his family.

Once he was dressed Drew took the time to brush back his hair and pull it into a ponytail, knowing exactly what he was going to do for his stream. It was certainly going to make his fans happy. After a moment of consideration he pulled on a zip up hoody as well, leaving it unzipped, but keeping it as an extra layer if he felt like he needed it. Once he was happy with his outfit he grabbed one of the makeup kits, then made his way to his computer.

“Hello everyone, I hope you are all having a wonderful day. I need to thank DirtyDaddy03 for today’s outfit.” DirtyDaddy03 had found him almost as soon as he joined Only Fans, and was one of his biggest donors, so Drew always tried to be nice to him. He stood, awkwardly spinning about to show off the outfit. “It’s really so cute, and it fits perfectly.”

The tips were already starting, and he took a moment to thank some of the fans, including DitrtyDaddy03, before turning to the next part of the stream. “Now, we’re gunna do something a bit new today, though I really hope I am a lot better at this than baking.” He held up the makeup kit with a nervous smile. “I’m going to attempt to do my makeup. Now, this is my first time trying this, so please be kind if it’s not perfect.”

His fans were wonderful, so many of them giving him compliments and tips, and he even noticed a few new names among the group. When he finally finished he was surprised to discover he hadn’t done a terrible job with the makeup, and his jaw dropped open as he examined himself on screen. “Oh. Oh wow.”

He wouldn’t have recognized himself two years ago, wouldn’t have realized that he was the pretty fem boy blinking back at him. Drew reached back, pulling out the elastic band to allow his hair to fall around his face, softening his features even more. “I’m pretty. I didn’t think I’d be so pretty.”

The sound of a larger tip caught his attention, and he blushed before thanking the donor before addressing his fans as a whole. “You all are amazing for supporting me with this. I don’t think I’d have ever dared try something like this without everyone’s support, and I really love this!”

He was surprised to realize it was true, that he enjoyed feeling pretty, enjoyed all his viewers watching him and thinking of how he looked so much like a girl. Still, he had a job to do, and couldn’t let himself keep getting distracted. “Don’t forget, you have until midnight to place a bid for an hour long one on one session with me, which is only an hour away, so get those votes in, and I’ll see you all tomorrow!” He blew them a kiss before ending the stream, only then turning his attention to studying his face once more. He reminded himself of his sister back when she was in high-school, of Al before first her husband died, then her kid fell sick. It made him feel a little guilty that he could enjoy himself playing with makeup while her kid was trying to die, even if he was doing it to help get her the treatment she needed.

Drew finally turned his attention to how much he’d made in tips, and his mouth dropped open once more. Usually he made somewhere between seventy five to a hundred dollars a day, but his donations were just shy of three hundred dollars. The bidding for a one on one session was also climbing higher than normal, and he had to wonder if they were expecting him to wear makeup and skirt. It wasn’t like it had actually been terribly hard, and Drew was actually enjoying the feeling of the skirt swishing around his legs when he moved.

DirtyDaddy03 ended up winning the bid, it was the fifth time that year that he had, so Drew wasn’t surprised. He always tried to push Drew farther than he was comfortable with, but didn’t argue when Drew said no. Hell, if it wasn’t for him Drew probably wouldn’t have explored his feminine side as much as he had. DirtyDaddy03 was certainly one of the strongest voices and tippers to lead Drew to the decisions that had him dressed the way he was.

Drew took a couple minutes to make sure he was ready before starting the private video for DirtyDaddy03, leaving the makeup and skirt on. Drew knew he was going to have to make it a regular thing and go even farther if he was going to get enough money to make sure he could pay off the lien on his home and have plenty of extra money for Kenny’s treatments. DirtyDaddy03 was a great sounding board for what his viewers would want at least, and Drew planned to use the private show to his advantage. “Hi there DirtyDaddy. I’m so happy to see you wanted to spend some time with me again.”

“I want to spend so much time with you Andrewsome.” The voice was course, though that was all Drew had to go off of to identify his fan. Even though his viewers had the option to turn on their own cameras for their one on one time DirtyDaddy03 never had.

Drew pouted a little at the use of his username. “You know you can just call me Andrew DirtyDaddy.”

“You look pretty today Andrew. Show me your outfit again. I want to see how it fits.”

“It first perfectly!” Drew grinned, instantly bouncing up to his feet to do as he was asked. The skirt was a bit shorter than he expected, short enough that he knew he wouldn’t be able to bend over without giving his viewers a show. That was the point though, wasn’t it? It was the only way he could help get Kenny the treatment she needed. “Do you like it Daddy?”

“That’s not my name Andrew.”

The voice was instantly angry, and Drew flinched, sitting down once more as he ducked his head, letting his hair fall into his face a little. “I’m sorry DirtyDaddy. I won’t do it again. I want to be good for you.”

The sharp inhale was clear over the speakers, and Drew relaxed at the sound. It had worked, and he wasn’t going to get yelled at for the next five minutes. “It’s okay Drew. You can make it up to me by showing me what’s under that skirt.”

Drew felt a blush flood his face, even as he hesitantly pulled up the skirt of the dress to show the lacy panties covering his cock. He’d been doing things like this for nearly two years now, but it never seemed to get less embarrassing. “Like this?”

“Exactly like that. You’re such a good boy. Why don’t you play with yourself a little as a reward for being so good.”

He’d done this plenty of times for his fans, rubbing himself through the soft panties, and the familiar feeling had him hard almost immediately. “Feels good DirtyDaddy.”

The groan and sounds of flesh on flesh coming through the speakers had Drew blushing before he stood, forcing a little smile as he walked across the room and sat on the edge of the twin bed he kept for his shows, keeping his gaze on the camera with the light that indicated it was the one recording at the moment. “I’m really hard DirtyDaddy.”

“Show me.” It was something he knew was coming, something he’d always turned down before, but this was the plan, to figure out exactly what his viewers would enjoy going forward.

“Okay.” It was soft, and Drew wasn’t even sure the mics would pick it up, but it didn’t really matter. DirtyDaddy03 was going to see either way as he pushed the panties down enough to free his slender cock. Drew ran two fingers down his length, watching what he was doing instead of the camera. “Like this Daddy?”

A sharp yell had him flinching again. “DirtyDaddy. You know that Andrew. You’re just looking to get punished, aren’t you?”

“I’m sorry DirtyDaddy.” His face turned red once more at his fan’s words, and his cock started to soften a little.

“Just don’t forget again. Now turn around and let me see your ass.” Once he’d complied, making sure his panties shifted around his thighs DirtyDaddy groaned in appreciation. “You’re so beautiful Drew. If I were there I’d spank you till your ass turned red for being such a naughty little boy.”

Dirty talk was starting so much earlier than normal, it meant Drew was doing something right at least. He glanced back at the camera, a pout on his face as he whined out a protest. “I can’t spank myself for you.”

“You could, but I’ll settle for you showing me that pretty hole of yours.”

God, it was so embarrassing, but his cock was starting to firm up again as he bent forward and spread his cheeks for the camera. “Such a good boy. I want you to start fingering yourself, stretch yourself so DirtyDaddy can take that tight hole.”

Drew couldn’t hold back his gasp at the words, though he quickly tried to cover them up. “Yes DirtyDaddy.”

He’d made sure to order lube when he’d decided to go farther with his videos, and he carefully started slicking up his passage enough to wiggle a finger inside. “Feels so good.” Weird is what it felt like, but his fan didn’t need to know he’d never put anything in his ass before. Hell, he’d hardly ever jerked off before doing these videos, much less exploring himself in other ways.

“Of course it does. Your needy hole is just desperate for someone to ram it full, isn’t it slut. Do you have a dildo?”

He hated when people called him that, but didn’t try and correct him. Instead Drew continued sliding the slick finger in and out, surprised to find he actually was starting to enjoy the feeling now that his body was getting used to the feeling. “No DirtyDaddy. I’m so sorry.”

“I’ll send one for you to use. Add another finger for now.”

“Yes sir.” The stretch of the second finger pushing in made Drew gasp. “Oh, it feels so nice.” This time it wasn’t just a show, he truly was enjoying the stretch of another of his slender fingers pushing into his hole.

The sounds from the speaker made it clear that his fan was jerking himself to the show, and Drew’s face turned bright red at the idea. “Please, can I please stroke myself?”

“Fuck yes. Touch yourself for me slut.”

It was an awkward position, kneeling on the edge of the bed with two fingers in his ass and the other hand around his cock, but Drew didn’t care. Everything felt so good, it felt amazing really, and he had to wonder why he’d never tried it before. “Need to cum. Please can I cum?”

He heard the now familiar strangled cry of DirtyDaddy’s own release, the man panting a moment before finally responding. “You can cum.”

It only took a few more strokes before he came with a cry, his asshole clenching around his fingers as his seed spilled over the panties and comforter of the bed. Once he finished Drew pulled his fingers free, sinking onto the mattress with a content moan. He’d never thought that having something inside him would make his orgasm so much better, had never thought he would enjoy something like that, but he had, and he was looking forward to trying it again. “Thank you Daddy.”

“Such a naughty little boy.” The voice sounded more amused than annoyed at least, and Drew heard the sound of a tip being left for him. “Our time’s up. I’ll send you something to fill yourself with for me forr next time.”

“Thank you DirtyDaddy.” He knew that he should get up and keep up the act, but Drew felt boneless after the intense orgasm. “Have a good night.”

“You too Andrew.”

His computer dinged as the timer for their session came to an end, and a moment later it notified him that he was alone on the video call. He needed to get up and log out, then take a shower and get to bed, but he was just so comfortable. Drew could afford to wait a couple minutes before he cleaned up.

The sound of his phone ringing pulled a groan from Drew, and he opened his eyes to realize that it was already morning. He winced as he shifted to grab his phone, and the dry cum pulled at his skin. “Al? What’s up?”

“I’m taking Kendra to the facility, remember? You wanted to talk with her before.” His sister eyed him through the phone, a frown on her face. “What are you wearing?”

“Sorry, I was sleeping. Give me a minute.” He turned off the camera, quickly going to his room to change. His sister rolled her eyes. “Look, why don’t we just call you when she’s done. You’re clearly busy.”

“No, it’s fine. I just need a minute. I was up late working.”

“Uh huh.”

Drew finally turned the video back on, this time dressed in jeans and a t-shirt. “See? I’m ready.”

“Fine.” Allison turned her attention off screen. “Hey Kendra, guess who wants to talk with you?”

“Uncle Drew!” The excitement in the girl’s voice before she even saw Drew was enough to brighten his spirits, reminding him exactly what he was doing everything for. Soon the girl’s smile was filling the screen. “Hi Uncle Drew!”

“Hey there Kenny! How are you?”

She hesitated, walking away from her mother and speaking a little quieter. “I’m a little scared Uncle Drew.”

“What’s got you scared kiddo? It’s just a hospital. You’ve seen lots of those.”

“Not this one. And mama says it’s a different treatment.”

“A better treatment Kenny. It’s going to make you feel so much better, I promise.”

She seemed hesitant, but nodded. “Do you think you can come with Uncle Drew?”

“I wish I could Kenny, I really do, but I promise you’re going to be amazing even without me there. Plus, you can call me any time you need me.”

A little smile crossed over her face. “Okay. I like your makeup Uncle Drew.”

Drew flushed, having forgotten he’d fallen asleep with the makeup on. “I’ll send you some makeup later this week so you can dress up too, okay?

“Yeah!”

“Alright Kendra, it’s time for us to go.”

Kendra pouted. “Okay Mom!” Her attention turned back to the phone. “Sorry Uncle Drew. I gotta go.”

“It’s okay Kenny. You’re going to do amazing. I’ll talk with you when you’re all done.”

He set the phone down once the call ended, fresh determination flooding through him. He’d do anything to make sure that little girl got to live the happiest life possible.