Yuki dressed like a girl and a special toy.

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All characters are 18 years of age or older. This is a work of fiction and is meant to be read as such
Basically Yuki is sinking deeper and he still doesn't know it yet.

Now, Maddy knew she could be a bit bolder with her suggestions, but they weren't yet in deep waters. For now, the fact that Yuki was willing to dress like a girl for her private viewing pleasure was a big step.

Yuki called out from the closet, "This is more embarrassing than I expected. Do I really have to do this?" "Of course not, baby, but it would make me really happy if you did. Don't you want to make me happy?" Yuki did, so he reluctantly walked out.

He wore a maid costume, in fact. "Why did you even have this lying around?" "You're not the only boyfriend of mine, Yuki, who's worn things for me. Plenty of guys do it, so don't be so shy."

Yuki tried pulling down the skirt, embarrassed that it might reveal his panties too easily. His hair was again done into pigtails, and he wore makeup and heels. "Just look at you, you're so cute and pretty!" She squealed as she brought in the mirror for Yuki to see.

Yuki looked at himself in the mirror. He did look like a full girl, and a really cute one at that, the type he would only dream about talking to. He couldn't help but feel himself get a little hard in his panties at the sight of himself. This only caused him to pull harder on his skirt to keep Maddy from seeing, though in truth, she probably wouldn't even notice.

"You know I bet nobody would even know your a boy if we went out." "Don't even joke" Yuki said as his face flushed. He would die of embarrassment if he went out dressed like this, not to mention if anyone did find out he was a boy he would never be able to show his face again. He knew about cross dressers and he had no idea how they did it.

Maddy got close to Yuki and began to kiss him. "It almost feel like I'm kissing a girl you know." He rolled his eyes, she said she wasn't gay but maybe she was a bit curious about it after all. But he was kissing his crush and he felt so happy about it. The worry of how he looked and his hesitance sort of melted away. This was totally worth it.

Maddy left the room to go get them some drinks and Yuki kinda sat on the bed and continued looking at the pretty girl in the mirror. He scooted on the bed to feel something hard under the covers.

He moved them to reveal a dildo! It wasn't very large, which caused Yuki to feel a little better about his size, though it was a good three inches bigger than he was. It wasn't very thick either and very pink. It seemed to have a vibrating function.

Yuki thought about Maddy using it on herself. Why was it here, too? Did she maybe forget it? Suddenly, the door began to open, and Yuki panicked; he quickly shoved the dildo into one of his pockets.

"Hey, everything okay?" "Yeah, no problem. I was just a little startled," Maddy smiled at him. She made a special note of the flipped-over covers. It seemed Yuki had taken the bait. She was hoping he would find it. She had planned on suggesting some ideas of him using it, but it seemed he had quickly stashed it.

Just as well, she thought. He would be more inclined to explore it at home. She sat next to him on the bed as they kissed a little more and watched some Netflix while sharing some alcohol. After the movie, they hugged, and Yuki left to go home. Maddy smiled as she lay in bed. Things were going great. She was sure Yuki would play with the toy. Maybe not the way she intended, but it was best he got familiar with it. He would be dealing with much bigger, manlier, and warmer ones in the future.

Maddy began to consider what to do next. Maybe she could influence his porn or have something playing on her TV by accident that he could watch involving black dicks. She should also get him some really cute outfits. Going out in public while wearing them might be too much of a big step still, but maybe for Halloween or even a convention would be fine. It was almost Halloween anyway.

Yuki got home and threw the maid outfit onto his bed, a gift from Maddy. Suddenly, the dildo fell out of the pocket and lay there on his bed, almost as if it was staring at him. Yuki meant to put it back when he got the chance, but the opportunity didn't present itself.

He picked it up again, and it seemed clean anyways. He wondered if Maddy had left it there by mistake. Maybe she was going to use it but hadn't yet. He sniffed it; it didn't smell used, it didn't smell like anything but latex/silicone. He got undressed to take a shower.

He looked at the dildo again. He clicked a button, and it started to vibrate. With each click, he accessed a different setting. Some were faster, some pulsed. His first thought was not to play with his butt. His dick, on the other hand, the vibrator looked like a shower/waterproof kind. He decided he would try it out.

He hopped into the shower and clicked it to the first setting. He was going to use it on the head of his cock, and he was amazed at how good it felt. He was beginning to understand why girls used these things. He flipped through settings, creating new sensations that drew soft moans from his mouth. If Maddy could hear him now, she would say he even moaned like a girl.

Yuki held it against his small, hard penis. Not even four minutes went by, and Yuki began to shake. He whimpered as he suddenly shot small ropes of watery cum. He was so turned on; he really liked this toy. "Surely she won't miss it," he said to himself. Girls must have plenty of them; what's one missing.

Yuki lay in bed as he stared at the vibe again, flicking through the settings. He couldn't help but wonder if maybe Maddy would use it on his penis. She didn't want to do any sex stuff for some reason. Would this count? He still could only dream about it. Now he wasn't finished just yet though. He began to use it again in bed as he flipped open his laptop and began to surf the web for something to cum to.

He looked for blonde babes and then some lesbian porn until he finally decided to write "pink dildo" and see what came up. The first one looked like a really cute girl in the video with a dildo similar to his in her hand. He clicked on it. He found her lying on the bed, dildoing herself. Her legs were shut. He expected to see her open them. She was already moaning like such a slut. But when she did spread her legs, as Yuki started to cum, he noticed it was a trap.

The hot girl spread her legs wide open to show a cock, probably as small as his, hanging limp as she shoved the dildo in and out of her ass. Yuki couldn't hold back as he shot again.

He was a little disappointed; this is what he came to, but he looked back at the screen, curious. He actually watched the whole video through. She was really hot. He wouldn't even know it was a dude had she kept her cock hidden. He began to feel a little ashamed as he was also passing. But something about it, he couldn't look away. She seemed to really enjoy it. And when she came hard, she kept going. He decided to research and found that boys can cum multiple times like girls using their butts.

Yuki was going down the rabbit hole; it was better than Maddy could have hoped for. It may have been that Yuki was already naturally inclined and Maddy had simply nudged him in the right direction. But as he looked into it more, the thought began to creep into his mind. Would he cum just as hard if he used it on his butt too? Yuki almost caught that thought before he decided it was time to sleep. But the seed had been planted.

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