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.
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.
“A-ah.. What?..” he started, breaking from his reverie.
“Shh.. Trust me.. I’ll make you cum.. I promise.. I promise okay? Just trust me..” she pleaded, just needing to get in on the heat and intensity of the scene, leaning down to spit on his ass and on the tip of her cock, rubbing it up and down.
“B-but.. I’m not..” he started to stand up too but felt one of her hands settle on his back.
“Don’t think, just feel..” She insisted, gripping his hip with one hand, the other gripping her cock on the middle, guiding the tip, lining it up, pushing forward..
He gasped, making eye contact with himself, watching the play of feelings across his face. He wanted to hate it, wanted to say stop, wanted to shove her off, but he couldn’t deny what he saw, the face in front of him was one of a beautiful, gorgeous woman driven to lust and loving every second. How could he deny that visage the pleasure it was so clearly receiving?
“G-good girl..” she panted as the thick tip of her cock popped into his hole. He might not have been a virgin thanks to his sister, greedy bitch, but that just made this easier, that and given his initial fear she doubted he’d ever been fucked with lube before, even if it was just spit, it made the world of difference.
With her cock lodged firmly inside him she moved both her hands now to grip his hips, she wanted to say so many reassuring things to keep him placated, but he seemed to be lost in a trance with himself, she didn’t want to break that for fear of his realising the situation he was in.
Jamie felt her push forward, for the second time in his life felt a cock push inside his ass, using him for pleasure, but this was different. This felt good. He felt as she sank inch after inch, slow and cautious into him, felt it expand and fill him, felt himself squeeze and hold her, eliciting a moan from her.
He stared at himself in the mirror. This time yesterday he had been Jamie, the slightly girly guy with a sister who doubled as his best friend. He’d had girlfriends sure, but he’d never gotten anywhere with them. That Jamie was less than twenty-four hours ago. Now he was being fucked for the second time. Wearing makeup, feminine clothes and hair extensions, he looked hot. To top it all off the girl currently exploring him was the girl of his dreams Kelly, the curvy brunette who had been the focus of so many of his late nights and early showers.
She stared down at him, eyes fixed on her thick cock sliding between his cheeks, delving deep into him, she didn’t stop, couldn’t stop, pushing her hips forward and pulling him back until every inch of her cock was buried deep inside him, surrounded and encapsulated by his ass, the pleasure pulsing through her body so extreme, enhanced by the mental dominance. She was the boss of this sweet little sluts ass. And he was getting off on her cock, that much was written across his face as clear as day and that alone almost made her cum then and there.
She pulled back and pushed forward, not shy to start off with a not so slow rhythm, they both needed this now, the more she gave to him the less he could find the room in his thoughts to question what he was doing, to hate himself, to wonder what he’d gotten himself into.
The small stall echoed with the sounds of their lovemaking, her pelvis slapping into his cheeks, his whole body rocking backwards and forwards, his panting little moans, her whimpers of pleasure through gritted teeth, part of her worried that even with having the two stalls either side of her locked by Lucy that people the next stall over would overhear them, but she couldn’t care less.
She urged him down slightly and arched up on her toes, so her thrusts angled down into his body, positioning her cock so it would rub against him in a very specific way, she bit her lip as she looked down at him, as much as her own pleasure was her goal, she wanted, if she could, to keep her promise and make him shoot.
He moved as she directed him, parting his legs further to lower himself, not understanding why she was changing position when it had felt so good. This thought lasted until she pushed into him again, fireworks going off in his mind as a whole new pleasure lanced through him. He felt weak and in an instant, Kelly found herself all but holding him up as she fucked him. She might not have been as strong as Caitlyn but this boy toy was a waif, and she knew how to pound a prostate.
She fucked him hard, his head starting to loll from the constant assault, soft painted lips parted, electric jolts of pleasure ravaging his body, her beat was constant and relentless, he wanted to move his hand down and touch himself, but his arms were weak, he needed them to hold himself up. He started to push himself back against her, wanting more, wanting it harder, wanting the pleasure to never end.
Kelly raised a hand to move a few strands of hair that had fallen in front of her face asides, feeling herself drawing closer, every movement threatening to push her past the point of no return, she let out a gasp! He wasn’t.. Was he? He was! She stared intently down at him, the little slut was pushing back against her, she bit her lip and slowed a little, watching as he picked up his pace to keep the beat steady.
Jamie closed his eyes, vision was useless to him now, only the pleasure coursing through his body mattered. His body moved on its own, keeping the pace up, pumping her cock in and out of him. He’d been wrong about her, wrong about this, she wasn’t fucking him for her pleasure, using him, no, he was using her for his pleasure. He felt her bend down over him, breasts pressed into his back heard her groan as she stretched, then stood back up, but didn’t think about it, didn’t care about anything other than the sensations powering inside of him.
Kelly stood again, panting and whimpering, one hand on his hip as she stood as still as she could, her other hand again holding her smartphone, this time as she recorded the whole thing, her not moving, him bouncing on her cock like the trained little slut he was becoming. She couldn’t believe it, even in her wildest dreams she’d never have thought he’d have come this far so quickly, he really was born for it. She wanted to send this video to Caitlyn, to show off and make her jealous, but this was just for her, her personal collection and maybe her personal blackmail. She made sure to catch his face in the mirror, the pleasure, the lust, but still Jamie, that could be useful.
There was no warning for Jamie, he didn’t know what he was feeling, what to expect, what was coming, this was new territory to him. One second he was lost in a mind of bliss as a hard throbbing cock bounced in and out of his delicious tight ass, the next his cock stiffened between his thighs, his mind going white.
His cock pulsed, hot cum shooting out to stain his old clothes that he kneeled on, gasping and moaning out loud and girlish, whimpering, the sudden influx of sensations was soon met by a familiar one, the steely hardening and liquid heat spreading deep inside his ass, Kelly was cumming inside of him, he had made Kelly cum! That alone drove his pleasure to new heights, there and then he didn’t care that he’d made her cock cum with his ass, all he knew was that he had given the girl of his dreams pleasure equaling perhaps his own.
She whimpered, struggling to hold her phone steady as she felt the boy cum under her, his ass gripping and squeezing, milking her cock so incredibly good she couldn’t believe it, the pleasure engulfing her cock and the lewdness of what he had done and the noises he was making were enough to force her to join him in a single wonderful climax, his body grinding back against her, keeping her hilted as she drained herself deep within him, filling him, claiming him. She could begin to see herself fighting Caitlyn for possession of him, with an ass like that there was no way she would remain a pawn in her games. She wanted this all for herself.
Her cum pulsed in jets into him, painting him white from the inside as his cock dribbled the last of it’s much smaller load onto his clothes, ruining them and ensuring he would be walking out dressed as he was.
Still hard inside him she blinked, looking down at him in surprise, he was still pushing backwards and forwards gently, milking every last drop of pleasure from the both of them, she let out a gasping laugh, breathless as she patted him on the ass. “S-stop.. You win.. I give in..” Kelly said with a grin.
He looked over his shoulder at her, panting softly and laughed a little too, soft, feminine, exhausted. He was in such a euphoric state he didn’t even notice as she dropped her phone onto her jeans.
Fuck, that just wasn’t fair. Even after all that he still looked gorgeous, his makeup still in place, his hair framing his face perfectly. She looked up at herself in the mirror, hair a mess, face shiny and flushed. He looked like he could go for hours and still come out looking pristine.
She started to pull herself slowly from him, eliciting a sigh of pleasure from the boy as her cock popped free, semi-hard, a thin line of cum joining them still as they tried to recover.
“I think.. I think we were… Too loud..” Jamie said, smiling softly.
“N-nah.. Lucy.. Lucy said she would cover us.. But.. But you might owe her a blowjob.. Gemma too..” she said teasingly, smirking softly as her hand caressed over his booty, squeezing it possessively, he still had his back arched for her, showing off.
Gods, was everyone a dickgirl? He didn’t even know if she was kidding. He looked down at his old clothes, like his old life, stained with his cum, his cock flagging as he swallowed softly. His mind was a haze of confusion as he again looked at himself in the mirror. Was this look forced upon him a lie? Or had his old life been a lie? Who, or what, was he? Given how much had happened in the last twelve hours alone. He knew in the next few days he would learn who he really was.
Kelly saw the expression on his face, the thoughts sinking in and stood him up on unsteady feet, turning him around slowly and biting her lip. She leant down then to kiss him, pushing her tongue into his mouth, dominating him as she pushed him gently against the wall, her hand running through his long blonde hair, all thoughts were forgotten as he raised his hand to cup and squeeze eagerly at her breast. She wouldn’t allow him to regret what he had done. Not if she was going to persuade him to be her girlfriend for real. Caitlyn be damned.
Hey! ^.^ If you enjoyed this story please consider checking out my Patreon to gain access to my stories 30 days before they’re posted anywhere else and to find out ways you could influence my stories!
I also love it when you to leave a comment, I absolutely adore hearing from everyone and I reply to every comment that gets left! So say hi! Xx