Kylie and Chrissy

By k darling

Published on Feb 3, 2017

Highschool

(Thanks for all of the amazing feedback,suggestions and ideas: keep it coming! Here's part 4 - enjoy)

PART 4 - RABBIT HOLE

The two friends chatted like nothing had changed. Although the subject matter was very different than it had ever been before. Music, skateboarding and hot girls were gone, replaced by girl's clothes and crossdressing. Although they did fall back upon an old tried and tested classic in their relationship: dating talk. Chris revealed how he had met Vicky, his rebound affirmation to convince himself that he was normal'. He admitted to liking her, but not being crazy about her -- She's a bit stuck up at times, and she gets pissed off really easily' he admitted. Chrissy, in true sissy style, complimented her fashion sense and agreed that she was `pretty'. Although she much preferred her slightly alternative clothing and makeup choices to her physical looks. Kyle couldn't work out if that was a compliment or jealousy rearing its ugly head.

Chrissy revealed her own experiences after their incident'. She briefly admitted to hooking up with a much older guy that she had met through a dating app. He was quite fit, and he made me feel so fucking feminine' she admitted, but as soon as I wanked him off, he couldn't stand to even look at me: he actually left me in the carpark half-dressed in girl's clothes, covered in cum and with a long walk home. What an asshole!' she explained. I've had shitty post-climatic experiences', she put on pretend sad eyes aimed at Kyle. `Bitch!' Kyle hissed playfully.

She went on to explain how she had ended up meeting and sort of dating' Zack. They had met during their first week at college and shared the same media class. They were social opposites but ended up working together on their first project for college. They had to film, edit and upload a video, using skills they had been focusing on in class. Nothing happened between them the whole time they worked together, they had just been friends. Oh Shit, yeh I forgot to tell you, I've been doing YouTube videos' Chrissy explained, Makeup tutorials and dressing videos, nobody's really seen them though..... except Zack - by accident.' She continued to retell the story of how she had used her email address to upload their media project to YouTube, and when a couple of months later she started making videos, she reused the same account, he then obviously stumbled across them looking for the project again. How did that lead to you hooking up?' Kyle questioned. Chrissy went on to explain about how he had sent her a message, just straight up telling her the truth -- he had seen her videos and thought she was hot. `He took a shot, I guess' Chrissy smiled. She was reluctant to go into too much detail about their dating experiences, as she knew it had caused Kyle to react so angrily at the party. Instead she skimmed over the details, said they'd hung out a few times, got quite intimate on a couple of occasions. Kyle pushed for more details but she batted his questions aside.

Kyle eventually took the hint, and decided to swerve the conversation in a different direction.

"I want to try it again" he blurted out, "the dressing up thing", he added.

"Really?" Chrissy was excited at the thought. She let her mouth open wide, she instantly went in to ultra-feminine mode. Her mannerisms became bigger and more purposeful. Her cock stiffened in her little panties.

"Yeh, I've kind of done it a little bit, well once, since you know we... did it the first time" he was becoming nervous, but decided to carry on.

"With Jodie's lingerie that you wore home?" Chrissy began connecting the dots, like a crossdressing detective. She became playful again in her mannerisms.

"Actually no, that's hidden still" he confessed, "It was with Vicky's things"

"Did you make Vicky's panties all sticky?" Chrissy teased.

"Yeh, kind of..." he blushed.

"What kind were they, was it just panties? Oh, do tell!" She flapped.

"These pale pink, ruffled ones, and some stockings -- it was pretty hot" he blushed again, his face glowing red in his confession.

"Well what are we waiting for?" Chrissy imitated Micky from Rocky II in the scene before the big training montage, the gravelly voice sounding strange coming from such a feminine sissy.

"What do you mean?" Chris was confused.

"Let's fucking do it. I'll doll you up, see how it feels" Chrissy was excited and began tapping her hands on her stocking clad thighs.

"What do want to wear, and how far do want to go?" She giggled excitedly. "I've got so many ideas...."


A plan was hatched:

Since Chrissy had gone the whole way and dressed up in full, Kyle decided that his next feminine appearance should be honoured by going all out'. Since his Dad was away on business and his Mum was still fucking Jerry' (his code for the fact that his Mum had left home and gone to live with a bald, ex-military turned car salesman named Jerry, who Chris absolutely detested), Chrissy was eager for Kyle to stay the night and play dress up like two girls at slumber party. But as tempting as that sounded, Kyle had agreed to go out with Vicky's family for her sister's birthday; he couldn't cancel and knew that if he did he would never go back to her again. He wasn't quite ready to take that step right now. `Just fuck her off, tell her you're sick!' was Chrissy's mischievous suggestion, but Kyle knew that would cause a major argument and he couldn't handle that when his future with Vicky hung so delicately in the balance. Instead they agreed on a couple of hours of sissy dress up time before he had to leave, and that was fine with both of them.

"Right, you go have a look at some of Jodie's dresses, I'll run the bath so you can.... shit, will you be able to shave your legs, with Vicky? She'll think that's weird, won't she?" Chrissy pondered.

"Umm, probably, yeh..." he admitted. "Will it be the same?"

"Nah -- it won't feel as fucking electric wearing stockings -- but it will still work, you've not got that much hair anyway." She reassured him, neither wanting to spoil the moment. "Okay, wigs -- I have only 2 options I'm afraid, and the first isn't that great. So it's just the one. Let's go grab that first and I'll sort your makeup out" she led him by his hand to the dressing table of Jodie's bedroom.

"No peaking until you're fully done, we're going for the full transformation reveal scene -- like Blind Date with two sissies, or Body Fixers with a sexy tranny at the end of it, or some home improvement show without all those burly builders...."

"...I get the idea" Kyle sniggered.

She giggled in response: "Sorry, I'm just excited!"

She went to work on his face, first applying a coat of -- what Kyle assumed to be -- foundation, rubbing it into his skin, asking him to close his eyes and tilt his chin when necessary. She then padded at his face with a round sponge coated in beige dust, paying particular attention to his lower eyes and nose. She riffled through a polka-dot bag and retrieved a brush, dabbed it into a few different pots of powdered colours and carefully swept it across his cheeks. It smelled intoxicating, the aroma of his Mum's bedroom, the perfume of kissing girls for the first time, the scent of something too delicate and feminine for his male brain to process. His eyes closed, Chrissy began the delicate and surgeon-like procedure of applying makeup to his eyes. He twitched, and blinked and flinched: it felt strange not knowing when the next layer would be added. "Quit it! Stop moving your eyes!" Chrissy hissed: "You'll look like Alice Cooper if you don't sit still". The most difficult bit was applying eyeliner; it smudged and ran, but Chrissy persevered -- if not a little bit frustrated. "Right, flicks - do you want any?" She enquired. "... Sure" he responded, uncertainly: he didn't have a clue what she was talking about. "Like Amy Winehouse -- bits that flick out from your eye..." she explained, still deep in concentration "well you're having them now, too late. In fact with the wig, that's kind of the look we're going to go for: a bit rock-chick but a bit retro and classic too..." she mused.

Chris was excited and he couldn't help but grin in anticipation. This felt incredible, it felt dangerous and sexy, it felt intimate and secret, and it felt right.

"Now pout", she commanded, as he awkwardly scrunched his lips together. "Woh! less than that! I said pout, not do a Sid Vicious" she laughed. "Which is ironic because you're looking a bit Nancy at the moment..."

`The lips are the best bit', he thought. It was the almost hint of kissing, the taste and texture of desire. It was incredibly erotic. He wondered how girls did this without turning themselves on.

"Right, now together -- mwah!" she smacked her lips together in an air-kiss and he imitated her action. It felt so girly to be doing this.

"Okay, still no looking, let's choose underwear first..." she led him by the hand to her sister's bedside drawers. He opened the drawer to the most thrilling array of colours and patterns and textures. Both of their hardons tightened at the site.

"Your sister's a slut!" Kyle joked.

"She does like sexy lingerie" he conceded. "Thankfully..."

"Where is she anyway?" Chris questioned, quickly realising the predicament of the situation should it arise.

"She's at work, and then she'll be at David's" Chrissy reassured. "She stays over at his, like, every weekend"

"Lucky Dave..." he joked, their boyish teasing emerging from beneath their feminine appearances.

Chrissy picked out a few options: her tried and tested favourites. The sailor girl looking blue and white frillies with big exaggerated bows on the front. The leopard print thong and push up bra set -- obviously a replacement for the one Kyle wore home the night of `the incident'. The pink satin full knickers with delicate trimming. The classy black lacy ones, see through and swirling-flower patterned.

In the end he chose a red and black satin set, the front a wide triangle of red satin and the back a delicate thong, with black meshing hanging delicately. The bra was matching and had gentle stitched black lace over the red satin cups.

"Okay I'll turn away, put them on... and these..." she tossed him a pair of fishnet stockings. "Remember to tuck your little clitty between your legs" she giggled, turning to face the opposite direction.

Kyle removed what remained of his clothes, and began pulling the satin panties up his legs. He tried to secure his throbbing erection into the front, and snapped the thong into place. It felt amazing, having the soft reinforcement it supplied as it clung to his bottom. The fabric tickled his bum, as his asshole twitched in response. He pulled up the lace fish net stockings, the cold suction of their tops sticking to his legs. He ran his fingers across them, shivering in ecstasy as his swollen dick struggled against his panties. He held the bra up to his chest, undid the clasp and placed the straps over his shoulders. He fumbled to reach the hanging back-straps, and tried in vain to pinch them together.

"Ermm.. little help?" He looked in Chrissy's direction, realising that at some point she had turned around and was watching him with a devilish smile. "Hey, you said no peeking!" he gasped.

"I couldn't help it, sweet cheeks!" she stuck her tongue out over her lips. She loved teasing him.

She helped him fasten the bra, and fought the urge to grab his pantie-clad bottom. She'd have loved nothing more to have pulled it and snapped it back -- using only her teeth.

"So dresses and accessories and the wig and you're done" Chrissy refocused on her sissy makeover session.

She chose the dress for him, taking the lead from his clueless expression -- the consideration of browsing through a whole rail of dresses, let alone choosing one to suit his look, was completely alien to Kyle. He squeezed in to a tight, black, shape-hugging dress. It barely covered his pantied bottom, but looked sluttish and right for the situation. He was zipped into the dress before Chrissy gave him oversized bangles to put on his wrists and a long beaded necklace to put around his neck. He clipped on huge hoop earrings: "these are mine - Jodie's ears are pieced", she explained.

"I only have these heels -- what size are you?" Chrissy enquired.

"A ten..." he said disappointedly, knowing that there was no chance that Jodie's shoes would fit him.

"We'll have to do without then. Just pretend you're walking home from a night clubbing and you've ditched your footwear." She tried to comfort him.

Kyle had gone quiet, and Chrissy tried to decipher his expression as he began placing the wig on his head. It was thick, black, wavy and hung at shoulder length.

"You still okay with this?" Chrissy said in a forced casual tone. It was too late to back out now, she thought.

"...I'm fine. I just...." He struggled to find the right words. "I really like this. I mean fucking really like it. My heart's racing and feel all funny and lightheaded.... thank you" he whispered.

Chrissy blushed, taken back by his honesty. "Stop it, silly!" she stuck her tongue out in response.

She completed her final touches, played with her own hair and applied a fresh layer of pink lipstick to her own lips before leading her friend to the mirror.

Facing them stood two teenage girls. Their bodies skinny and underdeveloped, their stances slightly awkward and clumsy. The girl with long blonde hair stood behind her friend, her arms resting on his shoulders. "You like?" she grinned. The second girl stood speechless, her mouth open, her eyes wide. She admired herself in the mirror, her black dress clinging to her slim figure. She tugged at the dress to pull it further over the massive bulge tenting out of the front of her panties. She pouted and shifted her head to the side, admiring herself from all angles possible. She was in awe, pure awe and wonderment. Her ears rang with deafening silence, as if her heart had been replaced with a hand grenade.

Minutes passed. It felt like an eternity.

"Kyle?" Chrissy finally broke the silence. "You like it...?"

"No..." she started "It's Kylie now...."

"Fuck..."

She squeezed his hand.


The rollercoaster was racing down the first big drop at a thousand miles per hour. The plummeting sensation, the dizziness, the screams, the thrills, the almost sick feeling in the pit of your stomach. That was how Kylie felt. Her arms around her lovers waste, she kissed, nibbled, slurped at her neck. Chrissy squeezed her bare bum cheek and fingered at the line of the thong panties. Last time had been pure lust, but this was something different: it was loving, it was tender, it was gentle. Their cocks inevitably locked against each other, two tent poles ever prominent through the gentle fabrics of their outfits.

Chrissy pried herself away, she stepped back and starred deeply into her lover's intense gaze. Her hardon raged and her mind raced. She knew she would come to regret this later, but she stood firm: "I'm sorry, but I meant it. We really aren't going to do anything today. This is so amazing and I have never felt this way before. But I really mean it, I can't take the rejection at the end..." she remained true to herself, as difficult as it was at that moment in time.

Kylie didn't say a word. Her eyes looked like she was struggling to restrain herself from ripping Chrissy's clothes off and having her wicked way with her right there and then on the carpeted floor of Jodie's bedroom.

The air was charged with electricity and lust.

"You're right..." Kylie sighed, deep and long.

"It sucks, I know. But I promise this will be worth it in the long term" Chrissy's eyes never left her lover's beaming stare. "I want this to really mean something..." her voice trailed away, her confidence deflating.

"Me too."


The heat of the moment slowly ebbed away, now a slow log fire filling an empty house on a cold winter's night instead of the earlier explosion in a fireworks factory, although both girls couldn't hide their throbbing erections. To an outsider they would have looked like an average pair of cute teenage girls -- aside from the massive revealing bulges their dresses sported. They sat and chatted awkwardly for a few minutes before Chrissy decided that they should take a few selfies and Kylie agreed to pout and pose with her best friend, fuelled by femininity and liberated excitement. They giggled and laughed and teased and joked. Kyle's usual over thinking and self-questioning had disappeared: he was lost in the moment of being a girl. He imitated Chrissy's mannerisms, he spoke softer, and he began to move with a grace and precision to suit his new appearance.

Chrissy connected her phone to the docking station that sat on Jodie's bedside table. A harsh voice blurted from the tiny speakers ("Dear head: shut up, I can't listen no more"), as the song `Rabbit Hole' erupted into a mess of guitars and fast pounding drums.

"Maybe not the most appropriate choice..." Kylie laughed.

"I know, that particular habit hasn't changed -- I still like good' music" Chrissy sniggered (I won't fall down that fucking rabbit hole!'), as the song's chorus clattered away (`I won't fall down that fucking rabbit hole!'). "Mind you, I'm not a fan of the new Blink 182 stuff either" she mused, "...just isn't the same."

(`I won't fall down that fucking rabbit hole!').

"Is this going to become our `rabbit hole'?" Kylie smirked, motioning at their appearances with wide eyes and raised eyebrows.

"Lamest thing you have ever said!" Chrissy laughed, brushing her hair to one side.

"Sorry..." She grinned "Put on something more... `girly'"

"Music should be genderless, I don't buy in to the idea that certain...." Chrissy began her lecture.

".... Woh! Chill out, you know what I meant" Kylie interrupted.

She swiped at her phone and new music began to pulse from the speakers, forming an up-tempo pop song with a female singer. They began dancing and swaying and imitating the moves of girls dancing in a nightclub, they giggled and laughed and ground against each other. They groped and grabbed at each other's scantily-clad behinds. Chrissy began rubbing her ass against Kylie's throbbing erection, while in return she squeezed her lover's dick, a tightly wrapped package of satin and silk. It felt like an outer body experience; it was like both boys finally knew what that `ultimate lesbian sex fantasy' felt like. Kylie definitely felt it, it was like she had both become somebody else and was watching somebody else act out a tantalising act of lust and femininity. It felt right, and she dropped to her knees in front of her lover.

Their eyes met and spoke a thousand words, both seeming to read the mind of the other.

"...don't..." Chrissy whispered in a half-hearted attempt.

"This doesn't count, because you didn't want me to cum and get all freaked out. Me. Not you..." She rolled her black silky panties over her suspenders. "I want to do this... for you"

Chrissy intended to protest, but found herself unable to respond. Her dick sprang out of her tiny panties like a jack-in-a-box, as her lover moved in for the kill. Kylie placed her hand around the thick pulsing shaft and moved her lips towards the engorged head. Then all of a sudden she was swallowing and sucking it, saliva running down the penis and onto her chin. It tasted strange, but not unpleasant. A slightly sweet, slightly sour, fleshy taste. She had heard tales of how girls practice and develop blowjob techniques throughout their formative years -- the preparation and planning for the first real time it happens. But that was girls, she was a sissy and she had a cock herself; she knew exactly what to do and exactly what felt right.

She was a natural: careful to avoid catching the shaft against her teeth, and focused primarily on the area beneath the head and the rest of the long pole -- the sweet spot. She gargled, gagged and gulped, her eyes looking longingly upward towards her sissy lover's gaze. Chrissy looked down at her, a stunned look of astonishment and ecstasy, moaning with each bob of her lover's head. There were no thoughts, no questions, no doubts, everything that ever mattered or was important was right there in that moment. Her lips rubbed against the vainy shaft, knees pressing into the firm carpeted floor. Chrissy placed her hand on her lover's head, stroking her hair, encouraging her to continue guiding her journey towards pure oblivion. She licked up and down the full length of the shaft, looking up innocently for her lover's approval. It was her turn to put on a show, her turn to tantalise and tease and torment. Her tongue wrapped around the head, she tried to deep throat but spluttered and gagged. Lipstick smeared, saliva dribbled, eyes watered. It was an act pure lust and love. She regathered momentum, her head bobbing and bouncing on the stiff and throbbing sissy penis in front of her. Chrissy groaned and moaned, before gasping `I'm close, baby. I'm close Kylie...'

"All dressed up and pretty..." Kylie mumbled and struggled to say, her mouth full of erect cock.

"Oh shit... Yeh, I'm going to... I'm going" Chrissy's eyes closed, her butt cheeks clenched.

Even with the vocal cues from Chrissy, Kylie was caught off guard. Chrissy's penis swelled and erupted, sperm shot into her moth and across her lips. She opened wide and let it run down her chin. The gloopy texture and bitter taste was too much, she let it run across her tongue and out of her mouth. She didn't swallow, but savoured the taste. She smiled up at her sissy lover's watching eyes.

"We just might have slipped a little bit further down that rabbit hole..." Chrissy whispered.

Kyle gazed up at her lover, eyes wide, her chin dripping with hot cum.

Suddenly the door cracked before it sprang open, a girl thundered in to the room her expression a look of absolute shock.

`What the fuck is going on here?'

`And why the fuck are you wearing my fucking clothes?'

Jodie Deaton's furious and confused scream echoed through the still house.

The two boys startled, with a look of pure terror. Deer caught in the headlights.


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