Patreon LogoYour support makes Blue Moon possible (Patreon)

Appropriate Attire (Ookami & MaxxyBoy)

As a kid max had never been really good with girls, he always got nervous when approaching them. He just always thought that they looked so pretty in all the different and brightly colored clothes they wore, that he actually felt intimidated by them. The only girl max ever talked to was his sister. Max had always fantasized about trying on some of her clothes, but never actually acted on it. One day however, when his sister had went out of town for a trip with friends, and Max had just gotten home from school, he decided to give it a shot.

Now Max never had a reason to act on his thoughts, but that day he was around some girls and he heard them talking and one thing specifically he heard them say was, "You know Max over there is always looking at us, but he never approaches us about anything and he only seems to look at our clothes, maybe he likes are clothes?" right after which another girl jumped in saying, "Would he look SOOOO CUTE wearing girls clothes, I mean just look at him." Max had always been a small boy. At only 15, he was 5'2" 105 pounds, and had a very odd feminine shape, he was also strangely hairless on his body except for his head which he had long light brown hair that came down to about the middle of his back, and something he never told anyone was that when he first his puberty he began developing really sensitive nipples that when touched were strangely arousing.

So after getting home, he went to his room to drop his stuff off then walked to his sisters room. The door was closed so he stopped for a moment, maybe he should rethink this, but knowing his sister was gone didn't back up that logic so he pushed open the door. He had never really been in his sister's room, but it what you would expect for the room of a 18 year old girl. He opened up her closet and found a nice pink blouse and threw it on the bed, he began to fumble through her dresser careful not to make his presence to noticeable, and found a nice green skirt and a matching pair of lace panties and a bra.

He began putting on the Panties and bra in front of a full length mirror on the back of his sister's door. Already he began to feel himself getting a little hard, but with only a small 3-4" penis it didn't bother him much. He started putting on the skirt and the blouse followed by some makeup, which he found at his sister's vanity and was amazed by how well he did. After looking in the mirror he was amazed that it was still him. He was just glad he was the only one home, he couldn't imagine what would happen if his family saw him like this.
 
Kyle tapped his foot impatiently as he stood infront of Max’s house. Knocking lightly a few times and getting no response. Max’s sister was supposed to meet him at the door, but after ten minutes of waiting outside and idly twiddling his thumbs, Kyle had started wondering if the silly little blonde even remembered that they were supposed to go out on a date today.

In truth, Kyle barely knew the girl. She’d randomly asked him out of the blue whether he was single at the moment, and when Kyle had absent mindedly told her that he was, she’d asked if they could go out Kyle figured that a bit of dating and messing around couldn’t hurt. She was pretty cute after all, and he had no intentions of turning down such a generous offer. That’d been a week ago, and today was supposed to have been the big day.

A small smirk playing on his thin lips as he shoved a hand in his jeans, patting down a string of condoms he’d purchased, fully intending to use them before the day ended. Kyle stood at a much higher height of 5’8” weight just over 145 pounds, he considered himself pretty average for his age (18), but people came in all sort of shapes and sizes these days, it was hard to determine what was and wasn’t normal anymore.

Brushing his hand against the door handle, fully expecting it to be locked tight. He was surprised when he found that the door handle turned without any resistance, the door opening with a soft click as Kyle looked around the deserted area to make sure no one was watching him. He wasn’t really breaking in, but it felt awfully similar to that one time when he’d snuck into an adult shop as a young teen.

Wasting no time, he headed right for Max’s sisters room, tip toeing the whole way and trying to keep as quiet as he possibly could, if he came across anyone other than Max’s sister, he’d probably have a hard time explaining himself at first. Hell, if he wasn’t careful they might mistake him for a burglar and pounce on him. While the thought of Alice’s family jumping on him was amusing, it certainly wasn’t appealing, and within moments he arrived at Alice’s room, the door opened wide enough for Kyle to see a small feminine arm sticking into his vision, he didn’t even think how it might have been someone else.

Figuring she deserved some payback for making him wait, he pushed the door open swiftly, taking a quick step into the room before grabbing Max by the arm, pulling the blonde into his chest, before leaning down and placing his lips against Max’s, not even giving the boy a chance to pull away or complain. Sucking on his soft lips gently before pulling away with a smug smile on his face. “Sorry, but consider it your own for looking so pretty” he joked, completely oblivious to the small penis, the lace panties obscured from Kyle’s sight by the skirt Max had put on.
 
(Wait so does Kyle not know it's Max or that he is a boy?)

As Max looked at himself in the mirror he couldn't help but feel aroused, He wanted to start touching his nipples, but before he could, the door swung open barely missing him, and a guy Max had never seen before grabbed him by the arm pulled him close and kissed him gently, much to Max's surprise.

Without thinking max's right leg bent up as he was kissed and leaned into the kiss, before the man pulled away. Max had never considered him self gay, or even thought of guys in that way, up until now. He really wanted to kiss the man again, even if he didn't know who he was, it was just so nice the first time. By now Max had completely disregarded the fact that he didn't want anyone finding out his little secret.

After hearing the man's compliment he couldn't help but blush, which was accented by the light makeup he had put on. He knew he looked like a girl, and for anyone seeing him for the first time may have thought the same. Max briefly wondered if this man knew after he had pulled away. Not sure if the compliment was mean to a joke or not, as hard is was to tell if he knew the truth, Max decided to let it go for now, he figured he would find out eventually.

"Don't be sorry..." Was all Max could manage, before he caught himself and managed to make his already feminine sounding voice even more so. "It was actually kind of nice" Max said as he smiled, not even thinking about asking for the man's name or telling him, his/her own.
 
Kyle took a moment to look the ‘girl’ over a bit more carefully, a faint frown on his lips as he tipped his head to the side slightly to look at Max from a slanted angle, she looked…. Different? In a good way too. Her lips had felt much softer than he’d imagined, but even her facial features seemed a bit different… probably the result of her nicely done make up. Kyle wasn’t all too familiar with makeup to begin with, and if Alice was going to go the extra mile to pretty herself up for him, he had no intentions of stopping her.

Dully taking note of the way Max leaned into him, and the rather flirtatious words that soon followed. Kyle couldn’t help but smile at her. A mischievous bratty grin that made him look much younger than he actually was, he’d thought ‘Alice’ would be a bit harder to crack, but the way she was acting, he’d probably be able to push her over and do her on the spot right now if he wanted. But then again, it didn’t hurt to be careful.

Lifting his hand and grabbing Max by the chin, he gently brushed his fingers over her lips, tracing the soft tissue of the flesh he’d been kissing only moments prior. From the sounds of things, no one was around, and even if they were, a click flick of a door lock would be enough to give him the privacy he wanted with the beautiful angel held in his arms.

“Glad you liked it, I thought you tasted delicious too” he smirked, lifting her chin up and lowering his own lips to rest an inch away from Max’s. He stood stock still for a moment, soaking up the cute boy’s appearance while literally breathing his hot breath down Max’s neck.

“We could do something that feels a lot nicer if you want?.... Actually I lied, we’re going to be doing those nice things whether you agree or not.” His lips once again pressed against Max’s, this time sucking and biting on his lips with enthusiasm, while his free hand roughly grabbed Max’s left ass cheek. Pulling him closer so that his semi hard cock rubbed against Max’s lower stomach.
 
As Max watched the man look him over, he began to realize something he had forgotten. He was in his Sisters room! So this man must think that Max was Alice, they did look similar at this point with only a few subtle differences. Max was debating on whether to tell the man who he really was, but decided against it for the moment.

As the man traced Max's lips with his finger, Max could not help but think of how hot this man was along with what he was doing. Not even trying anymore to rid himself of those thoughts, he decided to embrace the moment, because heck this was one hell of a moment that Max could not get enough of, and he actually wanted more, but didn't know where to begin.

As he looked up at the man who held him close, as he commented on the kiss, then lifting Max's chin up to raise his/her lips to his own, Max could not resist, he wanted to kiss this man again, because it was so good before. As the man stopped just an inch away from Max's lips, max go scared that he may have caught on, but as he looked into the mans Eyes he realized he was just observing how beautiful he was.

As the man spoke again, Max had gotten excited. When the man continues Max couldn't contain himself anymore, he didn't want to fight it or resist it, just wanted it to happen, and was happy to let it. As the man moved closer to kiss max Max moved closer as well. As they kissed, max getting more and more turned on by the biting and having the man's hand on his ass, which made Max jump at first but then lean into it. Soon Max could feel the man's cock pressing against his stomach, and wanted nothing more than to see it in all it's glory.
 
It was actually quite surprising how Max was acting. In Kyle’s mind he’d expected a bit of a struggle, but the ‘girl’ before him seemed to be giving in to him completely. He’d actually been partially be prepared to receive a scolding for entering the house and sneaking up on her, but the eyes that looked up at him, while afraid, looked as if they were begging for him to keep going. A cute look that no man would possibly be able to refuse.

His hand slid down from Max’s chin, and along his shoulder grabbing him lightly before his own feet stepped around the boy in a bit of a dance before shoving Max against the door. Blue predatory eyes watching Max’s reaction carefully so that he wouldn’t take things too far and ruin the good thing they had going.

“Silence is consent right?” he chuckled, parting his lips from Max’s once more, giving him an affectionate lick on the lips before lowering himself to a crouch as fluttered a stream of kisses down from Max’s mouth to his neck. His rough tongue brushing against his soft exposed neck a few times, coating and softening even more with his saliva, before latching on and sucking fiercely, perhaps enough so that it’d hurt Max a bit.

He tasted heavenly, and Kyle simply couldn’t get enough. His lips eventually pulling away to leave a hickey on Max’s neck, in plain sight where it’d be impossible to miss. “You’re mine now beautiful, and I’m not letting go until I’ve filled every single one of your holes with my cum.”
 
Max officially was ready, he didn't care what happened, he would give himself to this man. Not knowing this mans name didn't mean anything right now, he was hot and that's all that mattered, and his kiss was amazing. He wasn't even scared what would happen when this man found out he had a penis, actually he hadn't completely forgotten about it himself for the moment.

As Max was pushed against the door, all he could think about was how great it was to be in this mans control as he takes charge. Max smiled as he looked at the man wantingly as he was against the door.

"Yes." Max said still maintaining to keep the slightly more Feminine voice he had. As his lips were licked Max couldn't help but suck the mans tongue playfully for a bit before he began to kiss Max then slowly move down to his neck where he sucked and licked him. When he bit Max let out a light unintentional moan. It was more arousing than it was hurtful.

Pretty sure he now had the most noticeable hickey, as the man pulled away. He couldn't help but get turned on and aroused even more when the man spoke, even saying. "I wouldn't have it any other way" as he kept his more feminine voice and now sounding a little sultry.
 
Smiling happily at the cute little encouragement Max gave, Kyle’s hand briefly pulled off Max’s ass, flipping itself inside the skirt, and then slipping his fingers beneath the fabric of the lacey panties he was wearing. The snug panties getting a lot tighter at the front due to the extra mass that was now seductively rubbing against his round ass. His fingers creeping forward and teasing crevasse where his puckered pink hole awaited.

Kyle did notice how Max seemed to be straining his voice at times, but he figured the ‘girl’ was just trying to sound cute for him. Paying it no further attention as his others hand flowed down Max’s body, his fingertips brushing against his sensitive nipples as they travelled slowly downward over his stomach and towards where Max’s ‘pussy’ should have been.
 
As the Kyle put his hands in Max's panties starting rub his ass, Max couldn't help but lean into Kyle's hand as he felt his panties get tighter. As Max felt Kyle's hand slowly move toward his tight hole. He slowly but slightly moved to get him closer to where he was aiming.

When Kyle started to brush against Max's nipples, he moaned, this time a little louder than before. As Max felt Kyle's Hand move downward, he had completely forgot about the fact that he wasn't really a girl and that this man didn't know that. Max was just to into it and aroused to even think about it or make it even matter.
 
Kyle loved how cute and willing his supposed new girlfriend was. Her soft round ass feeling absolutely amazing against his hands, he began to knead it roughly. His teasing fingers intentionally teasing his sweet hole before pulling away to prevent giving Max what he really seemed to want. It was extremely tempting to spin Max around and have him bend over right then and there, but he wanted to play with the cutey before him for a bit longer.

Kyle’s other hand was heading down towards the concealed cock, but diverted at the last moment, sliding over his waist and grabbing ahold of Max’s hand. A sly smirk marking his face as he squeezed the hand gently.

“I could feel you up all day, but I’m starting to think you’re wanting something more from me, am I right?” he asked with a wink, his hand leading Max’s hand to the belt around Kyle’s waist, while the other hand drew a light circle to hint to Max what Kyle was referring to.

“I like a submissive bitch, but I also love a girl who knows what she wants, and isn’t afraid to reach for it” he suggested, pecking Max on the lips once more with a light teasing kiss.
 
Max, really wanting Kyle to finger his tight hole, couldn't help but get a tad bit sad, although no noticeable, when Kyle pulled his hand away from his ass. He just wanted this man to take him, and was close to just starting to rub this mans cock through his jeans to let him know this.

Max smiled cutely as Kyle grabbed his hand and squeezed it gently. Max knew what the man said was true, and he knew it he wasn't asking a question, but making a statement. Although Max loved this man feeling up his body, it was ultimately just the tease before the real event. Figuring his real voice was feminine enough he decided to stop trying to make his voice sound more so, seeing as he was never good at voices "You know you are." Max said as the Kyle motioned Max's hand toward his belt and circled it.

Kissing Kyle on the lips briefly, Max began to undo his belt, and then his pants before sticking his small slender soft hand down Kyle's pants to start rubbing his, previously semi- hard, now hard cock.
 
Back
Top Bottom