Kitty Kat Nip Ch. 01: Mile High Sissy

Kyle couldn't imagine a more boring graduation gift. While everyone else was headed to Cabo or Europe for a quick backpacking summer trip with friends, the family decided to rent a resort condo in the Dominican Republic for 3 weeks. This could have been bearable if it weren't the fact that they only afforded this trip by inviting every conceivable member of the family to pitch in, so the 3 weeks would essentially be an extended thanksgiving. Kyle could already feel the headaches coming on from the expected arguments and dysfunction made worse from the hot weather and extended time.

Worse yet, he couldn't imagine how his cousins and uncles would hound him for not being "manly" enough. Graduation had been a godsend to Kyle, and the promise of a faraway college was often the only thing that kept him from the deepest aspects of depression and angst. Making it worse was how trite his situation was; Kyle was short at 5'6, and scrawny at 120 lbs. Once he got his acceptance letter he started letting his already shaggy hair grow out, and now in the May air it was about chin-length and a bright brown color all around. He didn't feel like being a man's man, and this would simply be unacceptable to his Neanderthal family who only respected drinking more than machismo.

The day came to meet everyone at the airport. It would be 14 hours total trip starting from LAX to Kennedy, then down to land in the capital San Juan. His younger sister by a year was at his side, and they met with their parents who were already at the airport, herding the aunts, uncles and cousins into a manageable mob for the flight. His sister groaned at how heavy her carry-on bags were, and whined to both Kyle and anyone in earshot to trade loads since Kyle only a small tote to carry. Kyle knew not shutting up his little sister would only make his family bemoan how "ungentlemanly" he was being, so with a scoff he agreed to trade his comfortable tote for not only a purse but a luggage that took every inch possible allowed for carry-on, and as Kyle dragged it along, he was sure made every advantage of the maximum weight as well. Kyle tried to zone out and listen to his mp3 player and was unaware of how the plan would begin to fall apart, in retrospect; it would be explained to him like this:

Aunt Trudy assumed you bought the tickets one stretch at a time, meaning Kyle's father had to stay behind to fret and manage the altercations. This knocked out fair amount of the family right out the gate. Then at Kennedy Airport Uncle Harry had got into a shouting match with Uncle Dennis about attempting to sneak duty free cigarettes and hard liquor which was unknowingly slipped into everyone's bags before security. This ended in a fistfight between Harry and Dennis which got everyone involved apparently detained to cool things down. Kyle was either deeply in a book, on his mp3 player, or playing on his handheld and marched along passed security ready and waiting for his flight to board. as he handed his ticket to the attendant, his phone rang.

"Hello?" Kyle said,

"Kyle, where are you? Your mother said you were in isolated confinement after the brawl. You're not being renditioned are you? They treating you okay? Don't tell me you keistered your phone..." His dad rambled.

"What? No dad, I'm getting on the plane. How's the mess with Trudy? What brawl?" Kyle stammered, finally looking around to realize he didn't see a single familiar face.

"The plane? Kyle you're a genius! You're going to need to man-up and explain to the hotel that our condo reservation needs to be pushed back or augmented. I'll let you know what we can work out but it'll be great to have you there in person on our behalf! We might just save this vacation after-all!" his father cheered. Kyle thought for a moment, he would have a great vacation after-all. a few days in a resort town in the Dominican Republic sounded like a glorious retreat for a graduation present. He decided to play his hand the best he could.

"You know dad, I'll do everything I can for the family, but they might not hand over the keys to a full house to some kid who doesn't even speak Spanish and who doesn't have two quarters to rub together. I mean, how would I even get there from the airport?" Kyle did his best to sound cautiously concerned about the plan.

"Holy smokes, you're right! I'm going to wire you over some cash right now. I'll also call ahead the resort, you'll at least have a place to lay your head down when you get there and don't forget you need to try to get the resort to push our reservation back a few days so the family can get situated and join you over there. Think you can handle it?" His dad sounded concerned, and for the first time like something Kyle wasn't really familiar with, was this pride in his voice?

"I'll do my best, dad. Thanks for looking out for me, I'm sure we'll figure it out. I gotta go, no electronics on the plane. I'll let you know when I land. Okay, bye dad." Kyle tried not to smile too broadly as those last sentences left his mouth.

Kyle attempted to push his overstuffed carry-on bag into the overhead storage and it was clear there was no way it was going to fit. he decided he would relieve some of the pressure of his carry on by shoving items into his purse... Wait, he didn't have a purse. And this was his sister's luggage, which became immediately apparent when he pulled out several pairs of bras and panties from his bag to the curious looks to the businessmen sitting next to him. Kyle's face was crimson as he knew he couldn't explain, and quietly and embarrassingly moved skirts, skimpy tops, and girls shoes into his purse, shoved the carry on overhead, and slumped in his chair putting his ear buds in. That's when gravity of the situation really dawned on him: It would be days of him, alone in a resort, with nothing but his sisters vacation clothes. The thought excited him the more he thought about it. Kyle already shaved from head to toe, and he realized even in his day to day clothes his tight-fitting pants and choice of shirts were androgynous at best. No one would possibly recognize him, his entire family was literally a country away, and while he would from time to time slip into panties and a bra and take pictures for his own sexual gratification, he couldn't help his mind run wild with all the sexy outfits he would be free to wear all day in the warm Caribbean sun! Kyle closed his eyes, bit his lip and leaned his head back enjoying the rush of naughty thoughts in his head. He could dress up like a slutty little teen-aged girl and act however he wanted without the scorn of anyone!

His eyes slowly opened in a happy dream-like gaze to find the businessman sitting one seat away (between them was the empty seat where his sister would be sitting) smiling at him. Kyle's eyes darted forward and his mind raced about what was going on. What's this guy's problem? Is he making fun of me? Kyle's mind reflexively fell into the angsty, defensive thought patterns that were so common in his normal life, he tried to shake off the feeling of the man's gaze, and as the engines started up Kyle realized he had never flown before and it may in fact be scarier than he thought. By the time the plane taxied to the runway, Kyle was noticeably on edge, once again his eyes caught the eyes of the older businessman, who looked as calm as a hindu cow. The businessman leaned over and said,

"My name's Greg. First time flying? Try not to worry about it. It's safer than driving by far. Its only really dangerous during landing and takeoff, and we're almost done with one so you don't have to worry your pretty little head."

"Uh... thanks, my name's Kyle, yeah I keep trying to tell myself that, but I guess I just have nerves."

"No worries, there's two sure-fire ways to get your mind off of it, the first, is to talk about what you're flying for, it gets your mind off of the present and onto the happy thoughts of future plans." Greg mused.

"And the second way?" Kyle seethed through clenched teeth as the plane took its place ready to take-off.

"Oh, that's booze. Works great to clear the mind and loosen up during tense situations." Greg flirted, toasting water-bottle and winking knowingly. "Mind if I move over? You might need a sip."

Kyle nodded, Greg slipped over a seat and handed over the bottle. Kyle knocked the bottle back and quickly regretted it. It wasn't gin, and it was harsher than anything his small amount of experience prepared him for.

"Ever-clear." Greg laughed. "If you're going to travel light, travel right I always say."

Kyle gulped hard, but steeled himself to get himself relaxed. Greg and Kyle shared the bottle and went through the pleasantries and indeed Kyle's mind wandered away from dying in a fiery plane crash and onto the handsome successful gentleman next to him. He smiled easily, and Kyle was probably flushed from the alcohol getting into his head but he felt safe and blushing at Greg's wandering eyes up and down Kyle's young body. Greg was apparently celebrating by meeting a friend of his who was into yachting. Kyle explained his situation as best as he could while trying to keep his speech from slurring too much, he tried to keep up with the happy banter and didn't want to come off as an out of control youth. He mentioned the luggage situation and lost sight of how the conversation got to it's point.

"So," Greg started, "You get to work on your bikini tan by yourself in a resort for a few days? Must be quite the sight."

"What? No, I mean it's not like i don't know what I look like in a bikini, but not having any of my clothes is kind of a drag." Kyle tried to not let his mind wander towards thoughts of him in heels and a girls bathing suit, he sighed and brushed his hair out of his face.

"I bet you'll fit into a lot of those clothes fine, you'd probably make a really sexy girl." Greg was getting bold, and Kyle noticed he was earnestly enjoying the attention and felt comfortable being the pursued. Kyle began feeling deep yearnings he would never admit normally, but that some part of him always knew existed. He raised the stakes.

"Well, maybe if I had the manicure/pedicure thing worked out, I have been known to turn heads when I bend over and my hair is in front of my face."

"I can believe it. I bet you can be quite the little cock-tease with a little makeup and painted nails, I know I'd pay to see it." Greg urged under his breath.

"How about this? I'll trade you. Let me have the rest of that water bottle and I'll go into the bathroom, and freshen up just a little bit. Promise not to laugh?" Kyle had often teased boys online via webcam in his stockings and panties, but at 35,000 ft, with a man right next to him was exciting him to a whole new level.

"Mmmm laughing will definitely not be on the list of thing's I'd want to do with you. I mean at you, Haha oh lord forgive me, you'll be a beautiful little kitty." Greg leaned over and essentially whispered this into Kyle's ear. Sending shivers down Kyle's spine into his toes.

With the deal struck, Kyle grabbed his purse and intentionally slipped into the aisle of the plane not before sticking his rear close into Greg's face on his way to the bathroom. Locking the door he sat on the toilet and opened the purse to look into what his sister left to him. panties and matching bra which he moved from the luggage, hair ties, glasses, makeup, and a cute blouse which he could switch for his t shirt since both would look good under his hoodie anyway. He stripped down and slipped into the pink leopard print thong, pink leopard print bra, and put his jeans back on over panties, Kyle slipped the "who needs big tits when you have an ass like mine" softball t shirt on and covered with his hoodie. Having been in theater during high school to his family's dismay, he thanked the years of makeup experience he had as he dug into his sister's treasure-trove. foundation, eye-liner, pink lip-gloss, bronzer, and remover as well as enough tissue to make sure he could wipe it all off whenever he needed! As he was finished putting his face on, he found something else, pink nail polish with acetone in another pocket of the purse. Maybe it was the alcohol, but he definitely needed to look perfect for Greg. He finished painting, looked at himself in the mirror, pulled his pants down a bit so the top of the thong peeked out, and cleaned up into his purse to walk back to his seat. He knew Greg would enjoy the view much better this time as he got situated.

"Wow, miss I hate to tell such a beautiful girl that that seat belongs to a cute friend of mine who should be returning any minute." Greg's eyes devoured Kyle's body and this time Kyle leaned into the feeling. crossing his legs and acting as demure as possible as he sipped on his well earned water-bottle. He hoped the flight back would be this much fun.

"Thanks dear, but I'd hope you could still recognize me only being gone for a few minutes. Tell me, was it worth it?" Kyle cooed, as he enjoyed the warmth of the drink mixed with the lurid thoughts going on through his head.

"Absolutely; when you fly as much as I do you always wish to sit next to such a gorgeous young thing like yourself. It's really quite the treat, lets the mind wander and fantasize." reassured Greg.

"Fantasize huh? Like what? joining the mile-high club? Getting to seduce me into jumping into your lap and making some turbulence? That was my first time in a airplane bathroom actually, definitely have no idea why people complain about not having space to fuck in there, I could imagine a few positions we could try." Kyle whispered, leaning closer to Greg, licking around the mouth of the water bottle. He was swimming in the sexual tension at this point.

"Mmm, maybe you should show me. I've never had the pleasure, and I'd appreciate the demonstrations. Knock 5 times, and we'll see if you're a good Kitty or a bad Kitty." Greg said as he stood up to make his way to the bathroom. Part of Kyle's mind was racing, this was all going extremely fast. The majority of his mind however was shivering over how sexy it was to hear Greg's voice call him Kitty. He promised to himself that he would be Greg's good little kitty. He stood up, took a final swig of his water bottle, and got up to follow Greg into the small lavatory.

Kitty barely had enough time to finish the 5th knock before Greg opened the door and pulled him inside and locked the door behind him. Greg pulled Kitty close into him and began kissing him which let Kitty's small arms wrap around the man's neck. Greg kissed down the neck before he got the conversation back on track.

"So," Greg managed between hot wet kisses up and down Kitty's thin neck. "What are some of the way's two people could get it on in a bathroom like this?"

"Well for one, I could totally slip onto my knees and undo your pants with plenty of space. Watch." Any trace of Kyle had been completely consumed by his horny feminine alter-ego Kitty; who was determined to suck her first dick. Kitty kissed down Greg's neck and slid to her knees as she traced her fingers down his sides and met at his belt buckle, with minimal fumbling she slid his pants down and began placing hot kisses up Greg's leg. The young tramp could feel the heat of a real man emanate from the boxers and the scent of a real man egged the little slut on. Kitty pulled down Greg's boxers and bit her lip as she looked up at her partner. They locked eyes as Kitty planted a kiss and a lick on her man's growing member. Greg smiled and brushed hair out of Kitty's face and her eyes brightened up.

"I've got an idea!" Kitty said, pulling the hair ties from her wrist as she began parting her hair. within minutes she had two well split, even pigtails. She smiled and shook her head, feeling the tufts of hair bounce around the sides of her head. This ultra girly display as she put her hair up was apparently all the foreplay Greg needed as he grabbed Kitty's head and gently guided it towards his fully erect, thick 7 inched manhood. Kitty opened her mouth and let her tongue slip out to taste the head of Greg's cock once again before the smell and taste drove her wild.

Kitty's mouth worked Greg's cock over as if she'd been sucking cock in middle school. There wasn't an inch that she left out of the tongue bathing. Kitty discovered that sucking cock not only made her little boy-clit extremely aroused; but that Kitty felt right in her place at her knees sucking like a horny slut. The feeling of balls in Kitty's mouth was fulfilling and relaxing knowing that it was bringing pleasure to a real man. And so Kyle's mental objections and hesitations were simply drowned out and overwhelmed by the ecstasy pleasuring a man brought to Kitty. When her man's cock and balls were sufficiently soaked from Kitty's tongue, she slipped his cock into her mouth and began to lovingly tease her man's head with that eager tongue as her lips inched their way up and down his cock. Greg was very gentle with his hand on her head, and began coaching his little slut to be all she could be.

"Oh fuck yes you're such an amazing little cocksucker. Look at those slutty little pigtails bounce around as you slide up and down on my cock. God you must want my cum so bad, you're a cum-thirsty little faggot aren't you?" Greg moaned down to his plaything.

"mmmmhmmm ah aum a kokzuker" Kitty replied not bothering to slip her man's cock out of her mouth to speak clearly. She knew how good humming could be during a blowjob and decided to begin playing the part up, sucking louder and humming out how good and delicious Greg's cock was and how she couldn't wait to have him cum in her mouth. Instinctively, one hand wrapped itself around the base of Greg's cock not only to help pump the hot cum Kitty needed so badly, but also to gauge how far down her man's cock she could suck. It became an incredibly arousing game to her as she could feel Greg tense and enjoy ever extra millimeter she accomplished through practice.

Eventually, neither Kyle nor Kitty was really in control, the minutes felt like blissful hours as she did her duty the way only a happy cock-sucking fem boy can. She experimented for her own sake the different techniques that might better please the cock in her mouth, judging by the moans and pleasured gasps of the man attached to it. She found a quick paced pattern with her hand soaked in spit and pre cum stroking up and down the veiny shaft as her head bounced up and down deep as she could into her throat in a slight corkscrew fashion. Then she felt it. Her motions eventually paid off and to Kitty's surprise the little cocksucker's fellatio gave her spurt after spurt of deliciously hot semen. Her head went dizzy as her mouth kept up the pace, filling up more and more with cum until it began spilling out the side of the young faggots little mouth. She slowly pulled her lips off of his cock all the while flicking her tongue around the head before locking eyes with Greg again with her mouth open as if to showcase the cum floating around her tongue. She played with it in her mouth and enjoyed the smooth thick texture in her mouth before swallowing. Then the two spoke in tandem.

"Good job Kitty, guess you're both nice and naughty." Greg sighed.

"Thank you" Kitty said immediately, since she was talking about the delicious cum she had just received. She decided she wouldn't bother standing up, her legs still wobbly and her head still dizzy from being cum-drunk. Greg slumped into the toilet seat, and looked at the gorgeous young girl in pigtails that still had cum on her lips.

"You look beautiful. You make a perfect girl. I saw that little thong on you, slip out of those clothes." Greg ordered.

"Mm-mm yes sir." Kitty kept a hand on the wall as she got up. slipped off her shoes, and hoodie, and slipped out of her pants. The head of her stiff little cock was peeking out the top of the pink thong. Her girlish figure was accented wonderfully as she slipped the shirt off over her head, and she kept her hands up, playing with her pigtails in nothing but a bra and panties. Smiling at her man and doing little half-turns for his hungry eyes to feast. She bent at the waist to tidy up the clothes at her feet in case he would want a second blowjob and she peeked over her shoulder to see Greg was indeed getting hard again. She could only imagine how much more cum he had for her, and once she had made a little space for herself she got back onto her knees and let her hands rest on his slacks as she began planting kisses on his cock.