Rite of Passage Ch. 03

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Jamie's corruption furthers with help from his crush, Kelly.
9.1k words
4.72
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Part 3 of the 4 part series

Updated 06/08/2023
Created 02/17/2017
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No characters depicted in the story below are under the age of 18.

*****

Confusion and anxiety dominated Jamie's sore, battered body and mind. It was hard to maintain a positive outlook on things when your positive outlook became, 'I hope it doesn't hurt so bad next time.' There was nothing to look forward to anymore. And the fresh horror that was the mystery of his upcoming birthday present only served to set him even more on edge.

His fear of Caitlyn's wrath, however, now twice experienced, spurred him on to quickly finish his shower and start toweling off, grateful for the steamed up mirrors, allowing him to avoid his own image, something he couldn't bear to even glimpse right now as his mind was dark enough without adding the vision of himself, downtrodden and beaten.

He stepped out onto the landing, the towel wrapped tight, almost guarded, around his waist. He shuffled as stealthily as he could towards his bedroom, hesitating near the top of the stairs, hearing voices. He gently brushed his warm, wet hair away from his ear and bit his lip, trying to listen in.

"...And I just thought you would be better to help with this than me?.." came his sister's voice.

"Oh, the poor little thing. I had no idea!" someone else, though he almost recognised the muffled voice, which paused before continuing, "Well, actually it's not that surprising.. But I would be so happy to help! It's going to be so much fun!"

Jamie blinked as the voice finally rung true in his mind. Kelly, no doubt about it. Kelly was one of Caitlyn's friends from the last few years, she was around the same height as Caitlyn, her eyes and hair the same dusky darkness as his sisters own. She wasn't quite so toned and athletic and while she shared Caitlyn's slenderness and curves, her body lacked the definition of muscle. An aspiring actress, he remembered.

She had also been Jamie's first and longest running crush, the girl of his dreams. She was so similar to Caitlyn, he guessed, who up until recently had been both secretly desired and forbidden fruit, Kelly had offered the budding sexuality of a boy someone to jack off to, guilt-free. That and she had always been sweet on him. Something he desperately needed right now.

He made his way to his bedroom and was quick to dry himself off, his blonde hair was still damp with moisture as he pulled on his clothes but he didn't want to miss her. He found himself having to wiggle as he slid the tight jeans over the curve of his hips and selected a t-shirt from a pile of rather crumpled clothes. It wasn't exactly the perfect ensemble for greeting his crush but he was low on options.

He hurriedly made from his bedroom towards the stairs before stopping for a second, he had to remember that whyever she was here, she was here because of Caitlyn, which made him fear it could only end badly for him.

He quietly stepped down a couple of stairs, trying to see if he could steal any snippets of conversation before they noticed him.

"Mmhm! Back to the house no later than ten. That way our mom will be out again.. Will that be alright?" His sister asked.

"Deal. I'll keep an eye on my phone." Kelly responded, though the context of their conversation still evaded him.

He stepped downstairs and into the living room, finding his sister leaning against one of the coffee tables, nodding and smiling at Kelly who sat in the armchair, leant forward, eyes wide and eager! As he stepped into view, he looked cautious, anxious, maybe even a little afraid, the sight of his sister instilled that in him now.

"Aww! Jamie you poor thing come here." Kelly stood and crossed the room in a flash, wrapping her arms snugly around him and pulling him into her warm embrace, her full C cup breasts pressed close against his face. She'd never really paid him much attention and he wasn't exactly sure what Caitlyn had said to her, but this seemed good at least?

She pulled back and smiled brightly down to him, running her fingers through his damp hair to straighten it into some semblance of decency after he had hurriedly dried it. "You're so incredibly brave. God, we're going to have such an amazing day today! Just you and me!"

He blinked from Kelly to Caitlyn, expression blank and uncomprehending, he could see Caitlyn hiding a smirk.

"I told you, Kelly, that he would be very shy and insecure about it.." she said with faux concern lacing her voice, "But that's no surprise, coming out as trans is a big step for anyone."

His eyes widened at her words. She had told Kelly that he wanted to become a woman? He opened his mouth to protest but stopped just in time to consider his situation and whether or not speaking up would be a smart move. If he went against Caitlyn now it would not bode well for him. And what was it Kelly had said right now? Just him and Kelly all day? That... That sounded like a pretty good birthday present if he was completely honest with himself.

"W-where.. Where are we going?" he asked, looking up to Kelly, voice soft and anxious. He realised he was playing right into Caitlyn's hands. His timid voice, his demure demeanour, Kelly would see a delicate little woman trapped inside the wrong body, afraid and uneasy to reveal this secret to the world, not the truth, that he was afraid of further tyranny and abuse courtesy of his sister.

"To the mall silly. As girlfriends!" she said looking bright and happy. He'd seen her hanging out there occasionally, flitting from shop to shop with a gaggle of girly girls which very seldom included Caitlyn. The two of them seemed to connect over something deeper than shared interests.

"And it's your birthday little sister. So you better have fun. If you don't have fun and open up, Kelly will let me know okay?" she said, voice light and pleasant, though the undercurrents of her words were sinister. Be good and do as you're told or she'll know.

"I'll.. Do my best?" he said, trying his best to smile and overcome his worries, maybe he could actually enjoy himself?

Perceiving this as bravery, Kelly clasped him into another tight hug! She was seemingly giddy with the idea of spending the day with him, which was something he would never have expected but it made him feel secretly hopeful at the same time. A soft blush teased at his cheeks as he felt himself starting to relax.

"Come on Jamie, let's not waste any more time!" she beamed, taking him by the hand and leading him towards the door. He glanced back towards his sister who stood there with an unnerving smirk on her lips, waving towards him. Something in her eyes made his anxieties flutter.

He moved to pull his shoes and coat on. Kelly meanwhile, was already outside the house and heading towards, what he assumed, was her car. He shot his sister one last parting glance but she merely blew him a kiss and shooed him away.

Sighing he closed the door and walked after Kelly, following her down the driveway. As he walked towards the car she opened the door to the passenger side for him, pursing her lips as she seemed to over-critically eye up his choice of clothing, which he couldn't really blame her for, he wasn't exactly dressed up for a date, male or female in his crumpled casual clothing.

He slid into the comfortable passenger seat and she closed the door politely behind him, treating him like the girl she saw him now to be, making her way gracefully around the car to slip in beside him.

She let out a soft happy sigh as she flopped down in the seat, turning her keys in the ignition to set the car humming. She smiled prettily, reaching across and giving his thigh a soft reassuring squeeze as she pulled her seatbelt on. "Your sister's been very generous with her money today for your birthday, between her and me we've got this all planned out for you!"

As she started to drive she tuned the radio into a station playing a score of pop songs that seemed to be selected from the year's most played and oversaturated tunes. She turned the music up till he could feel the beat thumping through his chest and she started to sing along, practically bouncing in her seat as she danced as best she could while driving, singing with her beautiful voice.

"Hey!" she shouted over the lyrics, leaning in towards him while looking forward, only glancing towards him for a moment as she drove. "Come on, you must know the lyrics!"

He shook his head and blushed a little as she continued to sing, she prodded him in the side, sending an electric jolt up his side and causing him to squeak! "Sing!" she prompted again.

She started to sing, looking at him expectantly as they sat at a red light, her dark eyes deep and beautiful, hopeful. As the lights turned from red to green she glanced at him, looking a little disappointed as he remained stoically silent.

Jamie sighed and looked down a little. This was his day, and as bad as it had started it would only stay that way if he let it. He had an opportunity to change that, no point letting it slip through his fingers because of his embarrassment and anxieties. He raised his chin and joined her in song, which seemed to really perk her up.

They sang together for the rest of the journey, the loud music, her beautiful voice, her smile and happiness pulled Jamie from his worries. He no longer felt his fears weighing him down and he barely found himself thinking about Caitlyn. Just Kelly. He was out on a date with Kelly! Albeit as mutual girlfriends, but all the same he found himself genuinely smiling and looking forward to the day ahead.

As they pulled up outside the mall she turned the radio off and laughed breezily, grinning across to Jamie with adoration in her eyes. "Oh my god! You sing like an angel! You're eighteen now, you're definitely becoming one of the girls. We have a karaoke night every couple weeks, you would rock the joint!"

He blushed brightly and laughed too, he wasn't sure if she was kidding, and he wasn't sure if he wanted her to be. The idea of getting to hang out with Kelly as himself and not just occasionally bumping into her while she was with Caitlyn wasn't an unattractive prospect right now.

They climbed from the car and she locked it up with a click of her keys, walking across to him and taking him by the hand, she smiled encouragingly and squeezed it, looking down at him. "Be brave for me okay? You gotta be brave."

He wasn't sure what he hand to be brave about, this was just a dream come true for him. "I'll um. I'll try?"

The look of delight on her face was almost worth what he had endured so far since midnight. Almost.

She led him into the mall, joining the bustling crowds of people as they walked through together, hand in hand. He looked around, hope beyond hope that he might be spotted by some of his friends so he would have someone to witness that this date was really happening.

"Alright first things first." she stopped him in front of a fountain and stepped to the side, putting her fingers to her chin, tapping it as she eyed him over. "You have such beautiful blonde hair.. But it's a bit short.. You'd look a little dyke like.." She pursed her eyes and winked. "Not that there's anything wrong with that of course.. But come on, we can fix that!"

He blushed brightly at her comment, his mind trying to unravel her words and meaning but again he found himself swept away by her eagerness. They passed through the mall, chatting and relaxing, he found himself coming out of his shell a little and he had her almost always smiling and giggling.

He was so engrossed in the conversation that he didn't notice they had stepped into a store until she broke his reverie by waving down a member of staff. As he looked up he noticed, to his surprise that he had walked with Kelly into a hair Salon!

"Hey, Katie!" Kelly said with a smile to the approaching girl, a short brunette with a styled side shave. "Is Gemma about?"

"Mmhm! She's just on her break. If it's just your usual you're after I can help?" Katie replied with a smile.

Kelly laid her arm around the boy's shoulders and brought him closer, smiling as she presented him to Katie like a prize, causing him to blush as he looked at her, uncertain.

"She's having her first makeover, and you just know Gemma is the hair extension queen.." Kelly said in a conspiratorial tone.

"Oooh.." Katie said, smirking some as she eyed Jamie up and down as if seeing him in a new light. "Mm.. She's going to look divine. I'll tell Gemma you're here, take a seat?" she offered with a hand to a few spare waiting chairs, into which Kelly and Jamie sank.

He looked up to her, voice soft and cautious, "Make.. Makeover?"

"Of course! Our birthday present to you on this special day. Hair, clothes, makeup, nails, you know, makeover!" She winked.

"Oh.. Oooh.." Jamie sank back into his chair a little, feeling suddenly glum. Now it made sense. He had known there would be a catch, and here it was. He would be humiliated, made to look like a poor rendition of a girl for his sister's bemusement and worse, for her pleasure.

"Hey now.." Kelly's voice cut in on his dour thoughts, her fingers gently on his chin raising his head, frowning a little, looking at him with concern as she noticed his shift in expression. "You don't have to be afraid okay? I'm here with you and trust me, after this, you are going to look better than I do." she winked and smiled, then hesitated, before leaning in to kiss him on the lips.

An electric shiver raced through his body at her kiss, her full lips pressed against his own, soft and gentle, but with an intimac, he was unused to. He pressed forward slightly into the kiss, keen.

She leant back, breaking the kiss and leaving him wanting so much more. "Be brave, for me okay?.." she said, smiling, a glint in her dark gaze.

"..O-okay.." he stammered, swallowing.

"Hey girlfriend!" a voice came as a tall dark skinned woman with long immaculate braids stepped across to them both, meeting Kelly as she rose from her chair with a tight hug and a giggle. "Katie said you have something special for me?"

Kelly grinned excitedly and nodded, gesturing down towards the flushed and blushing Jamie whom Gemma eyed over curiously. "Hair extensions. She's enjoying her first day of being her if you catch my drift."

Gemma's eyes lit up and she pursed her lips before nodding, "Mm.. I follow you. I got you on this." she smirked and stepped towards one of the salon chairs, patting it and eying Jamie with a friendly, genuine smile.

Jamie looked up to Kelly who nodded reassuringly and ruffled his hair, "Go on sweetness. You're going to look simply amazing.

He returned the nod and made his way over to the chair, sinking down into it slowly and looked at himself in the mirror. "Isn't my hair a little short for hair extensions?.." he asked cautiously not looking for an out so much as genuinely believing his hair to be too short.

Gemma shook her head and ran her fingers through his blonde hair, measuring it with a keen eye, "Mm.. It only needs to be thirteen to sixteen centimetres, you'll do fine sweetness."

And so his fate was sealed. He sat back in the chair and watched as Gemma applied strands of what she called fusion extensions, though he wasn't sure entirely what that meant he was told it would help them last longer.

One set after the other he slowly watched himself transform. He had already been feminine, there was never any denying that, but the long blonde hair that began to adorn him was something new entirely. A few strands of blonde hair hung over his eyes as she worked, he raised a hand almost absentmindedly, brushing them behind one ear as she brushed at his new long hair.

"That turned out better than I thought it would.." Gemma said, self-satisfaction and pride filling her voice.

"Wow.. Gemma I know you're amazing but that's just stunning." Kelly interjected, her voice low but clearly pleased.

Jamie blushed as he looked at himself. He didn't so much look like a feminine boy any more than he did a boyish girl, a girl with a flat chest and a perchance for masculine clothes.

"I'm so jealous of her cheekbones.. She's just gorgeous isn't she?" Gemma again, smirking across to Kelly.

"She sure is. Mm! How much is that?.." she asked curiously, as Gemma led Kelly away towards the till leaving Jamie to stand as he stared at himself, tuning out of their conversation.

He hated to admit it, but he looked.. Cute.

Lost in his own reflection he looked up in surprise when he felt Kelly's hand on his arm, tugging him from the store. He glanced backwards, noticing Gemma giving him a friendly little wave as they departed. He turned his gaze back to Kelly. "W-where now?"

She looked at him and smiled broadly, "Further down the rabbit hole!"

He blinked at her, swallowing anxiously, but nodded all the same. He was already falling, part of him was curious to see just what would come of this.

Kelly by this point was almost brimming with excitement, all but dragging Jamie through the mall, making a beeline straight towards her target.

He stepped into a world of feminine outfits, a trendy clothes store with a perchance towards up to date fashion for women. He blushed as he looked around, knowing what was to come and in a way, resigned to it.

Kelly swept across the shop floor in a well-practised manner, she collected several items of clothing from hangers and shelves, draping them over Jamie's arms and giving him barely a chance to see what they were before new items were added or removed, deciding as she went, picking out the perfect outfit for him in her mind.

He found himself pushed forward towards the changing cubicles before he had a chance to realise what was happening, herded like cattle towards her goal. "Go! Go! I'll be right behind you!" she urged, patting him on the butt and smiling.

He stepped towards the cubicles, confused as he looked back at her, already she had flagged down a girl who smiled brightly at her, a 'Lucy' according to her name tag and started to talk with her, familiar.

He shook his head and stepped forward into the cubicle, leaving the door open for Kelly and laying the clothes out before him. Skirts? Leggings? Heels? What had he gotten himself into?

He had a few moments to consider the array of clothing before him and where he was before he heard the door click behind him. He turned to find Kelly there, standing with her back to the door, eyes glistening with excitement.

"Strip." She commanded, simply.

"W-what?" he stammered, swallowing as he backed himself against a knee high seat that ran the length of the side farthest from the door. From the seat to the ceiling stretched a mirror which he currently had to his back.

"Strip!" she repeated with a smile, moving to put the clothes up on a railing, "Come on we're girlfriends. There's no reason to be shy with each other anymore." Kelly urged.

Absentmindedly as he was thinking Jamie brushed a strand of long blonde hair back, tucking it behind his ear. Kelly couldn't help but smile as he so easily fell into feminine habits. This was a chance, a chance he had to take.

Finding a shred of bravery he spoke, "If there's no reason to be shy with each other ..You first?.." he asked, somewhat meekly.

Kelly blinked, a look of surprise passing across her features before she giggled. "Oh, I should've seen that coming, hm? You've been crushing on me since you first laid eyes on me.. Mm.." she paused, hands on hips. "Well, I did say that didn't I?"

Jamie nodded, keeping quiet as he sat on the small ledge, looking up at her hopefully.

"Well.. Sure, I suppose." she blushed some but smirked playfully.

She hooked her thumbs under the edge of her shirt and pulled it up and off over her head, revealing the smoothness of her hourglass form, her breasts held high in a black bra, her skin lacking the definition of muscles that Caitlyn possessed, but that only served to make her look more feminine, more beautiful than Caitlyn in his mind.