Rite of Passage Ch. 03

She leant forward a little bit, offering Jamie a view of her lush cleavage as she reached her hands behind her, fingering the clasps on her dark bra, pursing her lips as she struggled to unclasp it.

Jamie bit his lip as he watched, his heart fluttering in his chest as he watched her bra go loose, her hands running over her skin as she brought the straps over her shoulder and let it fall to the ground, her hands moving to her hips, her breasts on full display to him, one perfect eyebrow raised.

Jamie stared at her, eyes wide like a deer caught in the headlights, her breasts were full and heavy, their shape naturally curved.

"Ever seen a real pair before?" she asked demurely, sauntering forward, leaning over slightly so they hung enticingly just before his gaze.

Jamie blinked and shook his head looking up at her. "N-no.. Just on the internet." he lied, not wanting to recount his adventures that morning in the shower with Caitlyn, while it had been his first real experience, he would want to remember this one as his first.

Kelly placed her hand on the mirror behind him, her lips by his ear as she spoke, "They're so much better than online aren't they?" she spoke softly, her voice soothing as she bent over, giving him a view he had fantasised about so many times before.

Tentatively he reached up a hand but found his fingers laced with hers as she moved to hold it. "Mm. You can feel them and help me out of my jeans.. Just as soon as you've gotten changed."

Jamie looked up at her again, her hopeful face, beautiful and kind. He nodded. Eager. He'd have worn anything to see her in all her glory, to touch her was a bonus he'd dreamed of a thousand times but never thought would become a reality.

"Good.. Now.. Strip, please?" She said, standing once more and turning her sleek back to him, not with the intention of providing him with any modesty but so she could start going through the assortment of clothes she had picked out for him.

Blushing he started to strip his clothes off, placing his coat and shoes in a corner before adding his shirt, pants and socks to the heap. Before long he was stood in just his underwear, which, after some prompting from Kelly, he removed too. It was only after that that she started to hand him clothes, her eyes drinking him in.

First, she passed him some dark black leggings which she showed him how to put on correctly, he bit his lip as he rolled the soft fabric up to his thighs where they stopped with a lacy band.

Next, she passed a tight blouse, black and white with vertical stripes, it had a low neckline that would've shown off any cleavage, had he had any, as well as being quite revealing in that it relied on the sleeves and tightness to hold it on, having no shoulder straps.

She followed that up with a knee length black skirt that flared outwards some at the hem and a pair of cute, low-heeled shoes with straps that fastened over the open top. All in all the effect was incredibly feminine, stylish and a bizarrely good fit.

Before he had time to process his new look Kelly was standing over him, makeup kit in hand. She applied foundation, eyeliner and mascara with deft, practised movements. She pursed her lips as she dabbed at his full plush lips with her red tube of lipstick. She had decided not to apply any blush of her own from her makeup kit as Jamie seemed to be flushed with colour enough as it was.

She bit her own lip softly, eying her result and tucked her makeup kit away, nodding keenly. "Yeah.. Yeah, wow.. That's your look.. You look.." she paused, putting her hands on his shoulders and turning him around slowly to face the mirror. "Well.. Just look for yourself."

And he did, turning his heart skipped a beat. There was no doubt as to what he saw. A busty brunette, topless and smirking, standing just behind and off to the side of a slender, gorgeous girl, which had to be him. His outfit cute, stylish and girly, the top clinging to his slim chest. While that served to highlight his obvious flat chest, the full effect was disarmingly feminine. The skirt hung down to his knees, his thigh-high leggings extending down beyond that to his modest heels.

He looked like a college girl, long blonde hair, complementary but not overpowering makeup, kinda showy but not kinda slutty clothing, well, besides from that fact that under his skirt above his dark thigh-highs there was nothing but breeze.

"Well?.." she prodded him, curious as to what he was thinking as he stared at himself.

"I... I look so.. Girly." he said, at a loss for words, his voice soft and uncertain. He'd always maintained that this wasn't him, just a charade to placate Kelly and in turn, Caitlyn. But he looked so natural in his femininity.

Kelly giggled a little and squeezed his shoulders. "I knew you'd look gorgeous but gods.. It suits you so well. You're a perfect little sweetie!" she smiled and turned him back around to face her. "So er.. I guess I owe you the second half of my bargain. Wanna sit down and help me with my pants?.."

He blushed some and let himself be guided down to a sitting position, his face around about at the height of her crotch. He nodded some, he had been so engulfed in the vision of himself he'd forgotten about her promised reward for his good behaviour.

After setting him down she moved her hands to her curved hips and eyed him expectantly, waiting for him to make the move Kelly and she knew Jamie, was waiting for.

Determined not to let this opportunity slip through his fingers he raised them to the front of her tight jeans, his small delicate fingers easily unbuttoning the front, the only sound for a moment the slow run of a zip as he unzipped them. He could see from the smooth skin of her pelvis showing that she too, wasn't wearing any underwear.

He felt himself blush as he ran his hands across her thighs to her waist, fingertips hooking under the edges of her jeans and started to pull them down across her smooth skin.

His heart pounded in his chest, he'd dreamed about this so much.. Fantasised about it.. Desired it above all else. And here she was. Before him. In all her... ...Glory.

"Surprise?.." She giggled a little anxiously as her soft, hefty member was revealed to him, falling free from the tight prison of her jeans to hang between her thighs, her jeans falling to the floor to lay in a bundle around her feet.

She tilted her head and bopped him on the nose with a finger, "Sweety? I know it must be a big surprise... Finding out I'm just like you.. But we're girlfriends? No sense in hiding it?"

Just like me, he thought as he stared at it. Then up at her, fear and worry in his eyes, it started to make sense. This was all just a ploy, to get him looking like a girl so she could fuck him. He half expected Caitlyn to walk into the stall at any moment, laughing.

To his surprise, Kelly just looked just as worried, even ashamed. Embarrassed? Humiliated? What? Her hands moved to gather up her jeans, which she started to work back up her legs.

"W-what are you doing?.." he asked, voice soft and shaky, expressing the confusion that dominated him.

"You hate it! You hate it and you hate me." she said, her voice sounded as weak as his own, as if she were on the verge of tears, tugging her jeans up over her knees.

"What? W-what no!" he said awash with guilt, she'd revealed a secret to him and he'd looked at it in horror, he could only imagine what she was thinking, this girl whom he had crushed on for so long had revealed herself to him and he had looked at her like he looked at Caitlyn.

"N-no?.." she asked, looking at him again, soft and watery eyed, jeans around her thighs, just below her soft member. "You dont.. You don't hate me?.."

He shook his head. "N-no! Of course not! I just.. I just thought you were going to... Going to." he looked down and bit his lip, going silent.

She pursed her own lips, speaking softly now, "Going to what?.. Hurt you?.. With this?"

He simply nodded. Hands clasped in his lap and shoulders hunched he looked so small and vulnerable.

"Oh, gorgeous... We're girlfriends! Remember? I'd never hurt you." she smiled gently and let her jeans fall to the floor. "Let me guess. You had a run in with Caitlyn.. Didn't you?.."

He looked up at her sharply. "You know about her.. Her thing?"

She laughed a little and moved to sit beside him on the small chair, forcing him to scoot up so she would fit. "Well duh.. A fitness freak like her and a girl like me? What did you think we had in common.." she paused and slid a hand gently around his waist, holding him comfortingly, "Well.. Asides from a mutual attraction for you I mean.."

He flushed with colour, looking up at her still as she sat beside him, feeling the reassuring presence of her arm around his waist. "You.. Think I'm attractive?.." he asked, meek and confused.

"More than you know.. This morning when I saw you walk in I thought I'd died and gone to heaven.. A whole day with you! Can you believe that?" she said, practically echoing his own thoughts about her. "But now that I see you like this.. How mistaken I was.. If that was heaven then, now you're a whole choir of angels.." she bit her lip as she eyed Jamie over and he couldn't help but notice her cock throb, swelling slightly as she eyed him.

He looked up to her, his anxiety written across her face.

"Gods.. Caitlyn must really have done a number on you? You're not the first little doll she's turned out.." voice sounding anguished for a moment, "But it's nothing to be afraid of. Girls like us really should stick together, you know?" she said, voice soothing now, a hand giving him a light squeeze.

He sighed a little and looked away from her. Had Caitlyn put her through the same stuff as she was putting him through? As much as he feared Caitlyn he couldn't lie to Kelly, not here and now.. "Kelly.. I'm not.. I'm not a girl like you.. I'm not even a girl. That's just her plan. If I don't behave today and do as you tell me, she'll hurt me worse tonight.. I know she will. I'm not a girl.."

"Aw hun.." she said softly, raising her hand to his chin, turning his face up towards her. "Of course you are.."

He looked a little taken aback, his lips parting about to protest but she cut him off, "Look at you! You're absolutely gorgeous. I'm genuinely jealous of how cute you look.." She smirked slightly, teasing, "And you take it so naturally, did you notice you were swaying your hips a little after you got your hair done?.. And I saw how you looked at yourself in the mirror. You're loving this! You were born to be a girl."

"N-no.. I mean.. I can't.. I mean.. Ah.." he floundered for words as she teased her fingers over his waist through the soft fabric of his top. "That doesn't mean anything.. It certainly doesn't mean I like.. I like that sort of thing.." he said with a dismissive wave towards her tool, now semi hard between her thighs.

"No?.. How would you know if you've never tried?.." She asked.

"You know I've tried it.. Cait-"

"Ah!" she cut him off again, "I bet she fucked you like she would jerk off with her hand. I bet you've never been made love to before by a girl like me.. Hardly the same thing.."

He swallowed. As a matter of fact, he'd never made love to anyone, let alone a girl like her. "Well, no.. But-"

"Then you don't know that you won't like it do you?.."

He pursed his lips, annoyed at the constant interruptions. He opened his mouth to speak, but she beat him to it again.

"How about we make a sort of bet," she said, smiling then. "Let me do whatever I want with you.. And if at any point you want me to stop.. Say stop. If you say stop, I'll let you fuck me.." She winked playfully.

He flushed brightly at that, "W-what would you win?.." He asked, a stupid question he knew, but it was better than just sitting there with his mouth agape.

She giggled a little and nudged him playfully, "If you don't say stop, trust me, we'll both win a prize better than anything else.."

"S-so.. All I have to do. Is say stop. And I can fuck you? Actually, fuck you?.." he asked, his eyes going wide.

"Yup!" she said cheerily, then pouted cutely, "Though I'll be very very upset if you say stop without actually wanting me to.. Just.. Give me a chance, alright?.. I want to make you feel good. Really good."

He frowned a little as he thought. This wasn't like with Caitlyn at all. Worst case scenario, he fucked his crush. Actually, fuck her! Whether she had a dick or not, that wasn't a chance he could pass up, his eyes trailing over her nude, feminine form, her full breasts, her smooth skin. He could fuck Kelly. That one thought ran through his mind, again and again, erasing any suspicions.

"...Fine.. I'll give you a chance.." he said, he wanted to trust her, wanted to have someone in his life at the minute that didn't want to see him hurt.

She let out a delighted little squeak and leant down, kissing him quickly before standing and beckoning for him to stand too.

"Up! And turn around, face the mirror.. Just kneel right there on the edge.. Here.." She scooped up his old clothes, rolling them and placing them on the wooden bench to give him something soft to kneel on.

He followed her directions, a part of him just wanting to scream stop and have her fulfil her bargain. But that sounded like something Caitlyn would do, dishonest and deceiving. And he didn't want to disappoint Kelly, she seemed so invested in actually making him feel good.

He knelt on the edge of the chair, his hands placed against the mirror and his back arched, a blush on his cheeks as he all but realised he was presenting himself to her.

He felt her fingertips sliding up the leggings-clad smoothness of his thighs, under his skirt, flipping it up over his bare rear. With his knees spread as they were, he felt a sudden chill, she could see-

"Oh! Not hating his as much as you thought you were, hm?" Kelly giggled as she moved her hand down between his thighs, her soft fingers wrapping around his hard cock, pointed downwards, throbbing eagerly in her grasp, noting how he arched his back for her, like a girl in heat.

"A-ah! W-what do you expect... You're naked.." He protested weakly, trying to defend himself though even he knew that wasn't the only source of his arousal.

"Mmhm sure sweety.." she smirked and bit her lip, soft hand slowly jerking his cock, slow gentle motions, working him up so he would be more pliable with what was to follow.

As she moved her hand over his cock she glanced down, noting her phone poking out from her jeans pocket on the floor, biting her lip she squeezed and stroked his cock, eliciting a little whimper from the boy who closed his eyes briefly. Moving carefully knelt down behind him and grabbed her phone. Behind him, like she was, even with the mirror he couldn't see her hand below the edge of the chair. She had a text.

"Hows it going? Get your dick wet yet? C x"

"Looks gorj, bout 2 fuck, so ez! Thx 4 his sizes, prfct fit! K x"

She set her phone down and smirked happily, leaning in to kiss his full ass cheeks, soft little angel kisses, making him writhe back for more. It was just all oh so easy! Forget about asking for it, Caitlyn's brother was practically begging for it. She couldn't wait to see what else Caitlyn had planned for him, but so long as Kelly was counted in she was happy. This was heaven.

"Still okay?.." She asked, sounding demure and anxious as if she was afraid that he would say stop at any second. Though part of her, the painfully erect, eager part between her thighs almost hoped for that. Then she could drop this charade and have her fun. But she had to play her part, act the cautious curious lover, all affection and concern.

"S-still okay.." he moaned back a little breathy, a drop of pre forming at the tip of his cock which she massaged into the soft skin of his firm shaft.

"Good.." she purred softly, feigning relief. Though if she had her way it would probably be the last time she touched his dick. As often as she been on the receiving end of Caitlyn's thick cock she doubted she would have much to do with Jamie's. He wasn't exactly the pushy forceful type, which is what it took to make a girl like Kelly put out.

She kissed along his full soft ass cheeks, enjoying the sensation of his warm pliable flesh pressing against her lips and face. Moaning softly, eager and keen, fingers still gently massaging his cock she squirmed her face between his cheeks and let her nimble, experienced tongue lap out over his little star.

"A-ah!" He gasped in shock and surprise, leaning forward a little away from her, but her hand on his cock guided him back into place. "O-oh gods.. Kelly.. Kelly that feels.. Feels good.." he said, shame resonating through his voice, mingling with the pleasure in it.

Kelly rolled her eyes, it better have felt good. Lord knew she'd had enough practice over the last couple years on his dominate, high libido, strong willed and strong bodied sister. She rolled her tongue skillfully between his plush cheeks, teasing around his hole in slow sweeping circles, matching the pace to the slow twisting motion of her hand as it glided up and down his manhood.

As Kelly had planned, as she rimmed his cute little girly butt and stroked his soon to be seldom touched cock Jamie, with his hands pressed against the mirror had nothing much to look at besides himself. He stared into his own eyes, so foreign and strange, masked with pleasure and lined with makeup, he looked unrecognisable, he looked gorgeous. He looked like so many starlets he'd watched in porns, faces a shine of lust and desire. With his mind flooded with what she was doing to him, he could see just how much he really looked the part.

He squeezed down as she pressed her tongue forward firmly, feeling her soft tongue work into the hot embrace of his ass, working it around in rhythm with her fingers. Her other hand pressed and squeezed his ass, cupping and groping the tempting flesh, each little motion causing him to fall further and further into her desires, making the word stop seem oh so far away from him.

She moved her hand towards the crack of his delicious cheeks, one of her slender fingers gently probing at him as she kissed and licked at him, spearing him with her tongue, he writhed back, eager like the slut he still denied to being.

She withdrew her tongue and replaced it in one swift movement with her finger. He tensed, gasping and curling his toes in his heels, eyes going wide, "A-ah! St-"

She interrupted him quickly, her tongue running smoothly across the sack of his nuts, bathing them with her tongue as she squeezed his cock and worked the finger slowly but firmly in and out of his little ass, a new wave of fresh sensations causing his word to falter into a gasp! She had to be careful, that had been close.

He stared at himself, his flushed cheeks, his half-lidded expression of pleasure and lust, he'd never been touched like this before, and by Kelly no less, butt play wasn't exactly what he wanted, but it just felt so fucking good, he couldn't help himself but let out a soft girlish moan.

Kelly worked him in a slow building rhythm, hand around his cock, finger working his sweet little hole, tongue worshipping his smooth balls, stroking, licking, pushing, pulling, primal. She felt her own resistances begin to crumble and began to wonder instead how Caitlyn had waited so long before enacting her plans.

She bit her lip, staring at her finger disappearing between his cheeks, feeling the tight hotness of his ring around her finger, the enticing softness of his pillowy cheeks.

She released his cock and stood up, half breathless from her efforts and from her own lust. She ran both her hands over his smooth pale butt and squeezed, her thick cock landing squarely between his cheeks, gliding it between them and feeling him pleasure her for the first time.