Dressed up Itten

This story contains graphic sexual content, strong language, and has a lot of very strong sexual content in it such as Crossdressing, Kitten Play, Fingering, Mirror sex, Handjob, Begging, Size Difference, Size kink, Butt-Plugs, Creampie, Aftercare, and Subspace. Mentions: Free-Use, Somnophilia.

Fun fact: Aspen is Demisexual; only feel sexually attracted to someone when they have an emotional bond with the person. Also, Mykal's honorific is Alpha, I just wanted to do something different than the traditional ones.

All characters depicted in this story are over eighteen and have fully consented to everything that is happening.

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∂яєѕѕє∂ υρ кιттєи

A S P E N

Mykal had gone out with Ezra to do something. Aspen had been distracted when Mykal explained everything in full detail, but he got the main points down. One, Mykal was going to do something outside of the house. Two, Mykal would be with Ezra, and three, from the moment he walked out the door, he only had three hours before he would return home. Aspen sucked in a deep breath and swallowed around a knot that'd formed in his throat, his eyes squeezed closed as he stood in front of the giant mirror that was built into the wall. He was convinced that this was a dumb idea.

It wasn't even just dumb this was next-level dumb. Especially because he couldn't really remember when Mykal had left, nor how long had passed since he'd gotten showered and dressed. He was just standing anxiously in front of the mirror while Cameron did his hair, trying to avoid looking at himself but also insanely curious. He felt off, but not really in a bad way, either. He didn't really know how he felt.

Aspen was surprised by the amount of arousal he was feeling at the softness of the lingerie caressing his skin, and the feeling of the skirt hitting the top of his thighs was making his heart race. He couldn't stand to look though, he was too embarrassed. He had been so sure about this when he'd asked Cameron for his help, but now he just wasn't sure. Cameron pulled off looking feminine, but he probably wouldn't. And if Mykal saw him and he looked ridiculous... that was a horrific and embarrassing thought that somehow made desire burn hotter in his veins. He felt himself stiffening in his panties, his breath catching in his throat at the sensation of the soft fabric against his cock as he shifted a little. This was a bad idea.

"Aspen, you're turning blue. You have to breathe, darling!" Cameron chattered as he ran his fingers through Aspen's hair. Aspen let out a shuddery breath and bit his lip. "You are so pretty, I'm so jealous of your hair. It's so soft and bouncy." Cameron said as he pulled a section of his hair back and carefully put a rubber band in it, copying on the other side so that he could have a place to clip in the ears. Aspen squeezed his eyes tighter as he felt them slip onto place on top of his head.

Aspen wasn't sure what had made him decide to come up with this surprise anyway. Maybe it was simple curiosity, maybe it was because he thought Mykal would like it, or maybe it was just that Aspen had spent a year and a half watching Mykal's streams and fantasizing about him taking Cameron's place. Okay, that sounds bad but that wasn't how he meant it. He obviously wouldn't picture himself in Mykal's place given that he was the one he wanted, but it still made him feel bad. He'd been so envious of Cameron because he was everything that Aspen had always wanted to be but was much, much too shy to be.

Aspen wanted to be stronger and more confident like Cameron, but Aspen was painfully aware of his own movements and comments so much that it made his skin crawl. Any moment spent around anyone he was unfamiliar with and he became a stuttering, confused, jumbled-up mess. His anti-anxiety medications worked somewhat, but even so, it wasn't foolproof, and he still had anxiety on bad days--and around groups of people, and when he was alone and outside. Mykal helped a lot with his anxiety though. When Mykal was around, he felt infinitely safer than when he was alone, so even if he felt anxiety it wasn't as bad because he knew Mykal would take care of him.

"Alright, I think I'm done with hair and makeup. Are you ready to look?" Cameron asked, and Aspen stiffened. He had to look ridiculous and he was cursing himself. This was ridiculous, he was ridiculous. The outfit was a maid outfit--Cameron and Ezra had picked it out together, and it was short and skimpy, definitely barely covering his panties and he could feel the collar of it around his throat, but it was loosened enough that it didn't seem to be hindering his ability to breathe like he had first thought. He could feel the weight of the bow tied around his neck resting on against the white shirt, and the tops of the thigh-high stocking around his thighs--and the garter belt resting on his hips. He couldn't look.

"I have to look so silly," Aspen said, reaching his hands up to cover his face. Cameron wrapped his hands around his wrists before Aspen could put his hands on his face.

"You look beautiful, and I know Mykal is gonna love it!" Cameron said, pulling his wrists down so that he didn't mess up his makeup. "Look, I know it's probably going to sound super dishonest because I dress so femininely now, but there was a time when I was only comfortable doing it when I was alone. And there was a time when I felt like I'd look ridiculous too."

"Really?" Aspen asked, unclenching his eyes a little.

"Yeah. And you look much better than I did my first time I can guarantee that." Cameron said with a giggle. "I have to go, you said three hours and it's been two and three quarters. I need to get out of here before Myk gets home and discovers your surprise. Aspen, you look wonderful and Mykal is going to love it. Just take a peek when you feel ready, okay?" Cameron encouraged him and Aspen nodded, gulping a little.

"Okay," Aspen said softly, and Cameron patted him on the shoulder softly.

"I will text you tomorrow to see how things go," Cameron promised, and Aspen nodded again. "Every outfit we've picked out so far has been a hitter. It doesn't matter what you wear, Mykal loves it," Cameron said, and Aspen blushed and nodded.

"You're right," Aspen said, and Cameron giggled.

"Obviously! Now, I'm going to get out of here. Talk soon!" Aspen nodded and bit his lip as he tried to relax. He was too focused to even hear Cameron's footsteps as he walked out of the room and the sound of the door shutting behind him. He had a mantra he was chanting in his head: He could do this. Over and over again in his head until he could convince himself that he could. Aspen had never really experienced attraction before he'd stumbled onto Mykal's content so he really didn't know much of what he was doing. He'd always longed for the release of subspace, and Mykal had content that helped him get there even if he wasn't aroused. He had always had the urge to submit, but growing up and not really being attracted or aroused by anyone kind of made him come to think of his pleasure as secondary--but being able to put himself into the headspace of a submissive in combination with the way Mykal's voice calmed him down had him hooked.

After a little time, he'd even started getting aroused by it and that was exciting for him. But it coincided with him developing a crush on him. It had taken him time--as he listened to him, he sounded so kind and in control, so strong and admirable--but he'd managed to emotionally connect to him somehow. As Aspen had never really been attracted to anyone, he wasn't really bothered by the fact that it seemed impossible for him to ever get him, he was just relieved that someone had caught his attention. He would've probably kept just listening to him forever if he hadn't of heard Mykal speak in class that one time. Everything inside of him had tightened up when he heard his voice--he had immediately recognized him but he was so flustered he'd panicked and had no idea what to do. Mykal had exceeded his expectations and he'd come to realize that his pleasure wasn't secondary, it just came from a different place.

Mykal's touch had always left him on the brink of desperation, he had never been touched before, his own clothes made his sensitive skin feel itchy and uncomfortable and yet Mykal's touch didn't overwhelm him. It felt good. So good, and so relieving. He'd been so impatient in the beginning, his entire body burned in desperation constantly for his touch. His heightened sensitivity had always been a problem for him--but Mykal's hands felt amazing on his skin. Warm and soft, but the tips of them were slightly calloused from sketching all the time. It tickled but sent bursts of pleasure through him that left him shaking and desperate. Which he currently already was and Mykal wasn't even home yet.

He could do this. Right? He was thin enough that even if he didn't look quite right, he at least had some curves to back it up. Right? Right. Stay calm. It's fine. Cameron's right, there's not been an outfit he's worn to turn Mykal on that hadn't worked yet and Mykal complimented him on how beautiful he was all the time. Mykal was always honest with him, so he trusted that if Mykal said it he at least thought it was true. And if Mykal thought he was beautiful... well, nobody else really mattered.

Aspen took a deep breath to steady his nerves and pried his eyes open, looking over himself in the mirror. Aspen's eyes widened a little bit and roamed over his reflection, a blush staining his cheeks. Cameron was really good at makeup. The purple hues around his dark green eyes made them look brighter, and the black around his waterline and tight line made his eyes really pop a bit. His lashes were coated in mascara, but unlike when he tried to do it himself, it wasn't all clumpy and uncomfortable. His face was contoured and highlighted, adding a little glow to his ivory skin. His hair was curled and Cameron had brushed it so the curls loosened into waves, letting it fall down to his shoulders and around his face.

Then the kitten ears--they were perfectly placed and seemed just by shaking his head a little, much more sturdy than when he'd put them on himself. He couldn't help but feel a little shy and amazed at the same time, he actually looked... good. His body was curvy enough that the cinched waist accentuated his hips, and the bra that Cameron had bought him gave off the slightest impression that he might've had a chest--which he didn't because he was way too bony. Aspen's sensitive skin--namely, his nipples--were straining against the soft fabric of the bra and it made him shiver a little as arousal creeped through him.

The skirt was short--too short for his personal tastes, but it wasn't like he was planning on actually leaving the house in it so it didn't matter. The lace hem of his white panties peeked out from under it when he shifted to look over himself more in surprise. The skirt flowed around him as he moved, kissing at the very tops of his thighs in a way that had his heart speeding up in his chest. Shaving his legs had definitely been a good idea, his sensitivity was even more heightened thanks to it and each little brush of the dress on his skin, and even the feeling of the stockings and the garter strings had him aching a little in his panties.

He kept playing around with the dress a bit, showing himself off in the mirror a little, completely forgetting about time as he trailed his hand down his side and sucked in a deep breath. The plug. He needed to put the plug in. Just as he was about to turn around to do it, the door of the bedroom popped open and Aspen flushed immediately.

"Kitten?" Mykal asked, and Aspen peeked up and met his eyes in the mirror, his heart speeding up in his chest a little. "Jesus fuck ya look so beautiful." Aspen felt excitement pool in his stomach as Mykal closed the distance between them and Aspen whimpered when he felt Mykal's chest pressing against his back.

"Al-Alpha," Aspen stammered, his cheeks heating up as his cock tented the front of the skirt a little as Mykal put his hands on his waist and squeezed a little, his eyes roaming hungrily over him in the mirror.

"Ya look good enough to eat, kitten." Aspen trembled a little as he sank back against Mykal's chest, easily giving himself over to him. He was so horny and so sensitive, and Mykal was so close to him and his brain was absolutely short-circuiting. His eyes met Mykal's in the mirror and his face heated up more as his erection throbbed angrily in the panties. Mykal's hands slid down his abdomen and to his hips, then down to his thighs, gripping into them and massaging them. The pleasure made him lightheaded, but his eyes were locked on his fingers, the contrast of his tanned skin against his paler skin making his mind fog over. Anticipation built up in his stomach, his cock throbbing beneath the skirt and letting out a little bit of precum.

"P-Pl-Please," Aspen pleaded, his head falling back against Mykal's chest seconds later as his plea was answered by Mykal's fingers trailing over his cock through the fabric of the dress before he curled his hand around the head of it. Aspen shuddered as pleasure coursed through him, his eyes trying to close but Mykal tightened his grip around the head of his cock just enough to make his eyes pop open again.

Mykal's hand moved, wrapping around his cock more firmly as he brought the fabric of the skirt around his cock as he started stroking him. Aspen let out a quiet moan as his thighs trembled, the soft silky skirt rubbing around his lace-covered cock was oddly euphoric, it felt so soft and stimulating, and it had his body burning in a way that left him breathless. He whimpered, his eyes watching intently as he sagged back against Mykal more. It felt so strangely good, titillating in all the right ways. Aspen squirmed around a little, his breath catching in his throat as he felt Mykal's erection against his lower back and he let out a moan as Mykal kept moving his hand, the silky skirt still gathered in it. He was so close he felt like he was going to--Fuck, he might actually--

"Alpha waiiit," Aspen whimpered, pleasure consuming him seconds later as he tensed, his orgasm washing through him even as he tried to stop it. His entire body felt like it was vibrating, the different feelings of the clothes on his skin had him antsy in a surprisingly good way and in the aftershocks of his orgasm, his mind cleared enough that he didn't feel as embarrassed anymore.

"Aren't ya just a pretty little kitty, hmm?" Mykal hummed quietly as he released Aspen's erection, and Aspen flushed as he watched the skirt fall and settle, a giant wet spot on the pretty white apron on top of the skirt. He could only imagine what the inside of the skirt looked like, but he was too turned on and embarrassed to really think or worry about it. "Ya always look prettiest when you've just came, such a beautiful flush," Mykal teased as he shifted him a little. Aspen found himself being bent over, his cock springing immediately back to life when he felt Mykal's hands roaming over his ass through the skirt.

"T-Touch me," Aspen pleaded, his skin felt so sensitive that he almost itched for Mykal's touch. It wasn't unpleasant, but it was different, new. He was so desperate, he could feel how empty he was without something inside of him, his entire body was begging to be touched. Mykal kept him stuffed full almost every moment of his day--toys, cum, his dick, his fingers--sometimes, he'd even wake up to Mykal pushing inside of him when he was asleep, and he honestly thought those were his favorite times.

He wanted Mykal to use him, however he wanted, whenever he wanted. It'd taken him a lot of courage to even ask him about free use because it seemed so embarrassing... If it was anyone else, he might have not been able to even utter the words in a sentence together, but he trusted Mykal. Wholly, completely, with his entire heart. He knew he was always safe if Mykal was with him, and that was a big part of it for him. He had never felt safer in his life, he'd never felt more stable, or happier.

The sound of a wrapper crinkling caught his attention and he bit his lip as he looked over his shoulder to see Mykal opening a packet of lube. "Ezra gave me these as a gift," Mykal chuckled as he slipped his fingers into the waistband of his panties and pulled them down around his thighs. "I guess I know why now, he seemed awfully insistent on keeping the three-hour time window." Aspen gasped when he felt a lubed finger circle his entrance.

Aspen leaned his face forward and rested his cheek against the mirror, one of his hands coming up to rest on the surface of it, his eyebrows drawing together in frustration as he pushed his hips back into Mykal's fingers. He was teasing him so much, and he couldn't help but let out a needy whimper his eyes peeking back over his shoulder. Mykal slipped his finger inside of him finally, down to his second knuckle before pausing for a moment and pressing a kiss to his temple before he pushed the rest inside of him. Aspen let out a breath he hadn't realized he was holding, pleasure coursing through him as Mykal moved his finger inside of him.

Aspen was flying, his body wasn't sure what to do with itself in the aftermath of each wave of ecstasy so all he could really do was grip onto the mirror and moan. His fingers smudged the glass a bit as Mykal worked a second finger inside of him and his entire body seemed to be alive with sensation. When Mykal pressed the tips of his fingers against his prostate Aspen moaned loudly as the direct impact onto it made stars dance in front of his eyes. The fingers weren't nearly enough for him, but it felt so good he couldn't complain. He needed Mykal, he needed him inside of him not his fingers.

"I-I'm ready Alpha, please, no more--" Aspen whined, pushing back into his fingers. He just wanted Mykal inside of him, he wanted to feel full and connected and his entire brain was factory dating resetting at the pleasure pulling him under the rip-tides. He couldn't think when Mykal touched him, nothing worked right, he just melted and all he wanted was to rub up against him. Anywhere he could touch him, it always sent tingles racing through his skin and made him tremble in excitement. A third finger pushed inside of him and he let out a sob as his eyes rolled back. He could feel the fabric rubbing against his skin with every slight movement of his body and fuck it felt so good. He just wanted Mykal to fuck him! He wanted more than just fingers inside of him!

"Pl-Please," Aspen pleaded, stopping short to moan as Mykal's fingers rubbed against his prostate, but it quickly turned into a sob as pleasure hit him and his hole clenched desperately around Mykal's fingers. "P-Please, f-fuck me, I-I need you in-inside me, pl-please, I-I need--" He broke off with a whimper as Mykal pulled his fingers out. Aspen groaned and shuddered as his hole tried to close but it couldn't completely. It was a feeling he'd become accustomed to, but he couldn't help but squirm and arch into his touch, desperate to get Mykal inside of him.

"You're so gorgeous... So perfect, kitten," Mykal murmured softly, and the sound of his zipper sliding down made Aspen's heart hammer in his chest in excitement. He sucked in a deep breath and opened his eyes, and put his other hand up on the glass by his head, bracing himself as he felt Mykal's hands settle on his hips, gripping down into his waist where the apron held the dress cinched. His eyes met Mykal's in the mirror as he sank into him. Aspen let out a relieved moan at being filled, his hips immediately trying to rock back and forth.

Mykal's grip tightened on his waist and he whimpered as he squirmed around a little, Mykal's grip anchoring him still. Mykal smirked at him in the mirror, his dark brown eyes roaming over his reflection was desire as he pulled out and thrusted back into him, and then pulled out again, setting a pace that left Aspen struggling to keep his grip on the mirror and crying out his pleasure. Every thrust hit his prostate, only sending him further and further out of his mind with pleasure.