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Big, Black and Beautiful [Man to Big, Beautiful Black Woman TG]
🕑 Added 2025-05-02 22:45:53 +0000 UTCCommissioned Anonymously
When Jesse is karmically transformed into a heavy-set black woman, he decides to take it in stride. His best friend, however, struggles with the fact that Jesse is now walking around as his dream woman.
~
Prologue
Tray popped two aspirin out of the blister pack and downed them, following quickly with a swig of too-bitter coffee from the office machine. Hamish snickered as he watched and sipped at his own coffee smugly.
“Big weekend, hm?”
“Oh yeah.”
Tray grinned; his head was still thumping from the hangover, but it had been worth it. Mitch’s stag do had been the party to end all parties. Now that he was in his late thirties, Tray had begun to suspect those wild days were behind him. It used to be that he and his best friend Jesse used to do this sort of thing every weekend. They’d drink and party till they dropped, then dragged themselves into the office, head pounding, with stupid grins on their faces, ready to recover over the week and do it all over again.
As it was, it had been months since the two of them so much as got a beer together. So when Mitch had invited them for a wild weekend of booze and women, they’d both vowed to treat it like the old days. The last few hours of Sunday were nothing but a blur; Tray had woken up at home, sprawled across his bed with a puddle of drool on his pillow; he could only imagine that Jesse had been in the same boat and would come stumbling into the office kitchen any second, begging for coffee.
“Mitch already called in sick.” Hamish said, “Too hungover.”
“He was doing jello shots off that stripper's back half the night; I’m not fucking surprised.”
“What about you?”
Tray took a strategic sip of his coffee to hide the red in his cheeks; he’d gotten distracted by the beautiful, curvy black performer up on stage. Unlike most of the strippers at the club, she had some actual meat on her bones and while her tits and ass had been huge, you could tell they weren’t silicone. She had been the real deal. Beautiful black women were absolutely his type, though he tried to hide it. While the others did shots, he’d been busy knocking back beers and watching her dance.
“I was watching some other lovely ladies dance.” He said after a movement.
“Damn, I hope I get invited to Mitch’s next stag party.”
“He’s getting married.”
“Yeah, but if the stories I’m hearing are true, I doubt he’ll be married for long.”
Before he could reply, a woman stepped into the break room and did it for him. It took all of Tray’s self-control not to choke on his coffee.
“Glad to hear you have faith in him.” She said with a roll of her dark eyes.
The woman walked across the room, heels clicking against the linoleum. Her dark, curly hair flowed down her back and Tray found his eyes glowed to her swaying ass as she passed by. She was thick and bottom-heavy, without being fat, with a gorgeous pear-shaped figure. Her dark skin was perfectly smooth, and her bust threatened to escape her blouse, which, oddly enough, buttoned on the wrong side.
“Tray, dude, pick your jaw off the floor before you start drooling. People’ll get the wrong idea.”
She leaned back against the benchtop and took a swig of her coffee; it was as if she’d been here for years.
“S-sorry, are you a new hire?” Tray choked out, and the woman laughed.
“No, dude. It’s me. Jesse.”
“What!?”
The woman, Jesse, apparently, raised her eyebrows and shrugged.
“Well, if you think you had a wild weekend, you ain’t got nothing on me.”
~
Everybody knew there were three things to keep in mind when attending a stag night. To try and avoid a hangover, to not let anybody take photos and to be on the lookout for witches with a twisted sense of karma. It was rare, but every few months, there would be some article online, or somebody would mention a friend of a friend who said the wrong thing at the wrong time and offended a witch. They almost always ended up cursed and stuck in the body of some busty woman; sometimes, they even had their minds changed to match.
All that in mind, Jesse really should have seen it coming, but after too many shots and being wound up by Mitch and his guys, it may have slipped his mind. All he’d done was joke about Tray’s fetish for big black ladies; it hadn't even been that offensive. Life didn't care about fair, though, and neither did the witch who lured him out into the back alley and changed him.
One second, he’d been Jesse, pale-skinned, brown haired, average Joe who’d had a few too many drinks. The next his thighs were expanding, his tits had grown in and his skin had turned a rich dark colour. His ass had expanded and his hips had widened to an almost ludicrous degree and he’d been left dressed in a skimpy, tight fitting pair of booty shorts and a tube top. He’d been out on his ass. Literally, so the only thing he could do was make the most of it.
The only feminine clothing he had were the ones the witch gave him, so he’d forced his new body into a pair of slacks, a pair of his ex's heels and his work button-up the next day and been surprised with how good it looked, even if his nipples were showing slightly. If nothing else, the look on Tray and the other guy’s faces was going to be priceless.
~
“You’re kidding me.”
“Yes, Tray, this is all fake. It turns out I have secretly been a Hollywood make-up artist this entire time.”
“Okay, point taken but…you’re just okay with this? Shouldn’t you be freaking out?”
Hamish picked up the coffee mug he’d dropped and shook his head.
“I’m freaking out!”
Jesse chuckled to himself; he was right, their reactions were priceless.
“What can I do, man? At least my mind is intact. I’m still me, just…a black lady.”
“And you’re just going to go on with your life.”
“Pretty much, yeah.”
Tray shook his head in disbelief.
“Man, I knew you did too much pot in college. Nobody should be this chill.”
Jesse threw back his head and laughed; it was funny; even laughing felt different now. He felt the vibration in his chest, and his tits wobbled slightly. It felt kinda nice if he was honest.
“Look, I’m not thrilled about this, but it happens,” Jesse shrugged. “Just gotta deal with it. Come on, let’s get through the day, eh?”
“R-right.”
Tray looked like he would rather do anything else, but Jesse ignored that. His friend was just going to have to get over it. Once he saw that nothing had really changed except his appearance, things would probably go back to normal. A few people around the office were staring, naturally, at first he thought it was just because of the change but then his first button started to strain.
“Maybe I’ll have to get some new clothes…” He muttered to himself before flopping down into his chair.
Or rather, attempting to. Because his newly wide ass didn’t make it to the cushions, instead, they got caught on the arms, and hot coffee splattered all over his shirt and slacks.
“Crap!”
“Oh shoot, are you alright?” Tray asked.
Jesse rubbed at his sore cheeks and glowered down at the office chair.
“Yeah, fine, it was lukewarm…did you just say shoot? Since when do you not swear like a sailor?”
Tray blushed and muttered something under his breath. Jesse would have questioned him further, but he had bigger problems.
“I can’t work in wet clothes all day…”
Tray blinked and went even redder in the face.
“Real useful today, man.”
Jesse went in search of the floor manager, Gina, who almost bust a gut when she saw him. Of course, the gossip spread through the office like wildfire.
“Holy shit, I didn't believe it at first! What did you do to piss that witch off so much?”
“Is that really important? I need to go get new clothes. Can I take a half day or something?”
“Only if you tell me what you said. I mean, I have heard of this happening, but I never thought I’d see it!” Gina grinned like the Cheshire cat, “So your ass is seriously so big now you can't sit in a new office chair?”
Jesse grit his teeth and held back the flush in his cheeks.
“Yes…so while we’re at it, if I could swap with somebody who has a bigger chair, that’d be great.”
“Oh, go on then, come back with a pencil skirt or something. I want to see the fellas' jaws on the floor.”
“Aren't you supposed to be discouraging workplace harassment?”
Gina shrugged.
“Probably.”
Jesse rolled his eyes again and turned to head out of the office, cursing when his ass knocked a pile of papers onto the ground, causing Gina to burst into cackles once more.
“I’m going to assume I can go shopping!” he called over his shoulder and headed straight for the elevator. If he was honest, it was nice to have an excuse; these clothes didn't feel good at all. They stretched in all the wrong places and he could feel the fabric rubbing between his ass cheeks thanks to the natural sway of his hips now. His ex's heels didn't fit right either, and the arch of his foot was starting to ache.
It felt strange walking to the women’s section when he arrived. He wandered through the department store, dragging his hand over the racks of clothes. He had always heard that women’s clothing had so much more variety, but when it came to office wear, it seemed like much of the same. But then something caught his eye. A flash of deep red fabric shimmered under the store lights.
He stopped in his tracks. The dress was stunning. It wasn’t particularly modest; there was a daring neckline that dipped low and a hemline that barely brushed the tops of the mannequin’s thighs. Not exactly workplace attire. The fabric clung to the body almost sensually, and he couldn’t help but imagine what it would look like on his new, curvy frame.
It would be a waste of time to try it on; it wasn’t the sort of thing he could wear to work, but curiosity burned inside him. With a deep breath, he grabbed the dress and marched to the fitting rooms.
The door closed behind him, and Jesse stood in front of the mirror, eyeing himself with a mix of uncertainty and curiosity. He still wasn't used to all his new features: the full lips, the long lashes, the rounder face. He was…gorgeous. Despite being on the heavier side, there was a definite appeal he’d never entirely understood before. Maybe Tray’s fetish for bigger black women wasn’t so strange after all.
Jesse gladly stripped off the ill-fitting clothes and stepped into his new dress. The fabric felt so soft against his skin and clung in all the right places. When he turned to look at himself, he barely recognised the reflection.
The dress clung to him in places he never thought would look good. His hips, fuller than the mannequins he’d seen, created a curvier silhouette. His generous cleavage was on full display and looked utterly divine. Jesse’s heart gave a strange flutter. He had been trying to relax about this whole experience. He’d dealt with the shock by telling himself that nothing had changed, but he couldn’t say that anymore. Looking feminine had never called to him like this before.
He turned slowly, watching how the fabric shifted with his movement. His face flushed as he thought about how exposed he felt. But then he straightened his back, lifting his chin.
“I look… amazing.” Jesse’s voice was barely a whisper, almost as if he couldn’t believe it himself. But it felt good to say.
He stepped out of the fitting room, dress in hand, and headed straight to the counter. Sure, he couldn’t wear this to the office, but if he was going to be in this body for a while, he might as well get a few outfits that suited it.
As he walked out, he glanced down at the shopping bag in his hand. The dress was a start, but he felt like he needed more. Jesse walked into a cosmetics store, his heart pounding a little faster as he stared at the makeup shelves. If a dress had made him feel at home in his new skin, maybe make-up was worth trying. A sales associate, noticing his hesitation, approached him with a friendly smile.
“Looking for something special today?” she asked.
Jesse scratched the back of his neck and felt his soft hair; he still wasn't used to it being there.
“Um, I’m not really sure what I need. I’m just… trying something new.”
“Got it. Let’s start with the foundation. I’ll help you find your perfect shade.”
The saleswoman didn't seem put off in the slightest by his lack of knowledge. The process felt strange at first: brushes against his skin, the cool touch of foundation, and the gentle swipe of blush. His cheekbones shone under the gentle care, and the deep shade of purple-red lipstick really brought out the fullness of his lips. Jesse smiled to himself. It was funny; such a small touch made him feel bolder, more confident.
“So that’s what women meant when they called lipstick war paint…” He whispered, adding a touch of lip liner to really make them pronounced.
After picking up some makeup, Jesse wandered over to the jewellery section, where he found delicate necklaces and bold earrings to match. His excitement grew as he realised all the possibilities and combinations he could create with a change of shirt or accessory. His smile widened as he remembered the businesswear section where he’d started; maybe he could make all those simple garments into something more appealing…
~
Tray was beginning to think that he’d done something to offend the universe. It was the only explanation for him being tortured like this. He hunched over his desk and watched as Jesse walked in. He was still the talk of the office, even weeks after his change. Or rather, her change. An email from HR went out last week explaining that Jesse was fine being referred to by either masculine or feminine pronouns.
“I can't blame anybody for calling me a ‘she’ when I look like this, now can I?” She’d joked, leaning back in her extra-wide chair and indicating to her body. She’d taken to wearing tight blouses that showed off her chest. It was that perfect balance between not so revealing that it wasn't office appropriate, but enough to make men’s eyes wander. It was such a tease, one more button and they’d have a full view of her lovely tits. It would almost have been kinder if she were in more revealing clothing, then Tray’s mind wouldn’t fantasise quite so much.
What made it even worse was that Jesse seemed totally oblivious to just how much he was teasing his best friend. He’d sashay through the office, hips and ass wiggling without a care in the world. When Mitch asked if he had to walk quite so suggestively, he’d just shrugged.
“I am just walking, I can't help it if I happen to be sexy.”
Tray had nearly died then and there. It was one thing to be teased with the vision of your perfect woman and another to have her turn around and start talking about the upcoming football game. Having his best friend in his dream girl's body was a unique form of torture. He didn’t want to be attracted to Jesse, but he was just so hot he couldn’t help himself.
More than once, he’d been forced to dash into the bathroom to try and will himself from getting harder and more times than he would like; he had to take care of business or risk walking out with an erection. He bit his knuckles as he stroked himself, trying to picture anybody but Jesse, but in the end, his mind always ended up there as he spilled over his fingers in the stall.
He was starting to count the minutes to quitting time even more than usual. He could tell Jesse was hurt; she kept trying to talk to him and goof off the way they used to, but Tray just couldn’t bring himself to do it, at least not with the same enthusiasm he used to. Jesse kept saying nothing had changed, but how could he say that when he had tits big enough to rest on his keyboard when he leaned forwards.
The weekend was welcome, and Tray settled down on his couch to try and distract himself with football. What he needed was a good evening of manly sport. That would distract him from these confusing feelings for his best friend. The game was just about to start when the doorbell rang, and Tray felt his eyebrow twitch in annoyance.
“How hard is it to get some peace…” He muttered, opening the door, fully expecting some charity bucket. Instead, Jesse was standing there, one hand on her massive hip, the other holding a pizza box.
“Delivery!” She joked with a wink.
What fresh Hell was this?
“Jesse? What are you doing here?”
Jesse raised an eyebrow.
“It’s the quarterfinals? We always watch the last few games of the season together.”
“Oh yeah…” Tray awkwardly stepped aside and let her in. “I guess I forgot.”
“We’ve been doing this every year for almost a decade; how could you forget?”
Jesse walked into the lounge room and bent over to place the pizza on the table. Her shapely, perfect ass was in the air, perfectly presented for Tray. Her cheeks were on full display thanks to the tight-fitting yoga pants she’d put on under her too short skirt. Tray bit his lip and tried to think about football.
~
Jesse adjusted herself on the couch. The cushions were slightly sunken from years of use and her heavy ass was practically crushing them flat. She leaned over and got herself a slice of pizza, licking the cheese from her fingers as it dripped and only half-watched the game. Things had been off between her and Tray ever since the change. She knew Tray had a thing for bigger black ladies, and now that she was one, things were bound to be awkward. But she’d assumed he would be over it by now.
Even as the game started, Tray didn't reach for the pizza. He kept fidgeting, avoiding eye contact, his fingers drumming nervously on the armrest. Jesse tried to ignore it, focusing on the game, but the tension was thick and obvious. She huffed; enough was enough.
“So are we gonna talk about this, man?”
Tray cringed.
“Can you not call me that?”
“I’ve always called you that, man. And don’t change the subject.”
“Fine, what is it you want to talk about?”
“You know what, you’re being weird!”
Tray threw up his arms in frustration.
“I’m being weird? You’re a chick! A curvy, busty….chick!”
“It’s just the outside; I’m still the same-”
“No, you’re not! You’re even going by ‘her’ more than ‘he’ these days! You’re dressing like a woman! Your tits are practically falling out of that shirt and I can see your bra through it!”
Jesse blushed; maybe she had been going a little crazy with the skimpy outfits, but it was all so new and exciting.
“Maybe I got a bit swept up in the whole clothing situation, but it’s fun to dress for this new body. I’m trying to be cool about it, but it is weird having a whole new build. Dressing to fit it helps me feel…good about myself.”
“And that’s fine.” Tray sighed, rubbing at the back of his neck. “But you can’t expect me to just accept it.”
Jesse felt her heart sink. Making friends as an adult was hard, and she didn't want to lose Tray. Her eyes burned slightly, and she quickly blinked away the tears.
“So we can't be friends?” She said quietly.
He turned to face her, his eyes searching hers, and for a moment, she saw the vulnerability she’d never noticed before.
“You’re… you’re my dream girl,” he blurted out, the words rushing together like he was afraid he’d lose his nerve. “Physically, I mean. You’re perfect. But it’s weird, right? Having a crush on your best friend? Especially since you were a man a few weeks ago…”
“Oh…”
“Yeah…”
“I knew you liked ladies like this…I think that’s why the witch made me this way, but I never thought…Well, I assumed I would always be your buddy over everything.”
She tried to laugh it off, but Tray looked so vulnerable and unsure that her heart softened. The truth was, she had been curious about what it would feel like to have sex again. She had entertained the idea of going speed dating in lesbian circles, but a little voice in the back of her mind had stopped her. At first, Jesse had assumed she was still just self-conscious about her new body and not knowing how to use it, but now she realised that hadn't been it at all. She’d been scared to touch herself, because she didn’t know what she was doing. As a man, she’d felt women up, but doing it herself felt…weird. Perhaps they could kill two birds with one stone here.
“It’s… unexpected. But hey, why not give it a shot? Life’s too short to wonder ‘what if,’ right?”
“What?”
“You and me, let’s get all this tension out of the air. Worst case scenario, we make it worse, but that’s a future us problem.”
Tray looked like she’d just suggested they jump off a bridge.
“...HUH?!”
Before Jesse could overthink it, she leaned in, closing the distance between them. Tray’s eyes widened, and for a moment, she thought he’d pull away. But then his lips met hers, soft and hesitant at first, before deepening into something hungry, something urgent.
The kiss was electric, sending a jolt through her body. Tray’s hands came up to cradle her face. His touch was almost reverent, like he’d been dreaming of this moment for years. She melted into him, her curves pressing against his lean frame, and for the first time, she saw him not just as her best friend but as a man: a man who desired her. Gods, it felt good to be desired.
“Oh god, you feel even better than I imagined.” Tray breathed, “Those lips…I never thought I would get to touch a woman like you.”
Jesse felt a thrill go through her at being so wanted.
“Well, now you have. So… what’s next?”
Without another word, he leaned in again, his lips brushing hers in a series of soft, teasing kisses. Tray’s hands cupped her heavy breasts, stroking them through the thin bra and shirt so that her nipples poked through even more. Jesse’s hands found his chest, her fingers splaying over the firm muscles beneath his shirt. She pulled him closer, her body aching for more, and he responded eagerly, his kisses growing more insistent.
They ended up sprawled on the couch, clothes discarded in a hurried mess. Tray’s hands were everywhere, tracing the curves he’d always admired from afar. He ran his hands over every inch of her, especially her ass, as if he were trying to memorise every curve. He squeezed the cheeks hard enough that a pinch of pain joined the pleasure and made it all the sweeter. A soft moan escaped Jesse’s lips, and he felt himself stiffen in shock.
For a moment, they paused and broke apart. Jesse felt his whole body tinge red in embarrassment; he had no idea he could make such sinful sounds. Tray’s eyes burned into her.
“Do that again.” He said roughly and squeezed once more.
Jesse meant to bite back with some quippy comeback, but their dynamic had shifted now, and all that escaped his mouth was another moan. She let out a soft moan, arching into him, and he smiled against her skin, his lips hot as he kissed his way down her neck.
Jesse’s hands wandered lower and slid down his legs. Her hands brushed his member, and even Jesse was surprised by the spike in her own arousal. She’d never found men attractive before; maybe it was this body, maybe it was that the witch made him Tray’s dream girl. It didn't matter; what mattered was the growing heat and wetness between her legs, threatening to seep onto the couch. She reached out, wrapping her hand around him, and he let out a sharp gasp.
“Fuck, Jesse,” he groaned. “You have no idea what you do to me.”
She smirked, stroking him slowly, enjoying the way his muscles tensed beneath her touch.
“I think I’m starting to get the picture.”
His hands roamed over her body, his fingers dipping between her thighs and brushing her folds. He slipped a finger inside her, and she moaned into his mouth, her hips rocking against his hand.
“You’re so wet.”
His eyes locked onto hers, dark with want, and he leaned down to capture her lips in another hungry kiss. He withdrew his fingers, and before she could protest, he was pushing her back onto the couch and positioning himself at her entrance.
“Ready?” he asked, his voice hoarse.
She nodded, her heart pounding in anticipation. There was no point backing out now.
“Yeah. Do it, Tray.”
He thrust into her, slow and steady, filling her completely. Jesse gasped, her nails digging into his shoulders as he stretched her. For a second, they stayed together, and Jesse gave a breathy laugh.
“I guess I did change a little on the inside.”
Tray just groaned and gripped her wide hips to anchor himself as he started to thrust. The couch creaked beneath them as he moved, his hips snapping against hers. Jesse met him in the middle, her body moving in perfect sync with his, her breasts bouncing with each impact. Tray’s fingers turned white as he gripped her, his fingers digging into her soft flesh as he pounded into her relentlessly.
“Fuck, Jesse, you feel so good,” he groaned, his voice strained. “So tight, so wet… I’ve dreamed of this for so long.”
His words sent her over the edge, her orgasm crashing over her like a wave. She cried out, her walls clenching around him, and Tray followed, his thrusts becoming frantic as he spilled deep inside her. Jesse panted, chest rising and falling as she tried to catch her breath. That had been so intense, she couldn’t believe it had really happened.
Tray seemed to be in a similar state of awe as he slowly pulled out and shuddered. His face was a mix of satisfaction, sheepishness and delight. Like, he couldn’t decide which emotion to go with. Jesse was suddenly hit with the realisation that he’d just made his best friend's fetish dreams come true, and what was weirder…he didn’t mind. In fact, he felt an odd sense of pride.
“That was…amazing.”
“Do you think it cut the tension?” Jesse joked.
“A little.” Tray laughed, “But now I know how good you feel, I don’t think once could be enough. Or twice even.”
“A dozen?”
“Maybe two.”
The two of them snickered, and Tray settled himself down, head pillowed on Jesse’s breasts.
“You realise you have it made in the shade now, right?” Jesse chuckled for a moment. “You have your dream girl, but she is also your best mate.”
“So we’re going to keep doing this? For real?”
The excitement in his voice was palpable, and Jesse basked in her own power. She never realised just how much feminine wiles could really do. In one evening, she’d managed to wrap Tray around her finger. Not that she would ever abuse that power of course, but she could still enjoy it.
“If you want to,” she replied, “Or if things are still too awkward for you, I could try the dating scene…”
“Don’t you dare.”
He raised his head and gave her nipple a hard suck for emphasis, making Jesse shiver with delight and gasp.
“Keep that up, and I’ll never stray.”
“Well then,” Tray grinned, “We’d better start round two right away, don’t you think?”
Jesse didn't get a chance to answer; he latched onto her nipple and began sucking, causing the most delightful sensations to shoot through her. Their dynamic had certainly changed, but Jesse could live with being Tray’s dream girl, especially if the perks continued to be this delicious.
Epilogue
Tray wasn't sure what they were exactly these days. Friends with Benefits seemed like the most accurate title, but it implied things were purely physical. Jesse was still his best friend, but now that she was his ultimate dream girl, he was sort of like her sugar daddy as well. He’d never understood the appeal of paying for a girlfriend, but now that he had one, he finally did.
Not only did he get to enjoy fucking his ultimate woman, but he got to dress her up too. These days, Jesse was embracing all things feminine, and now that they were together, Tray was more than happy to oblige her. They stepped into the shop, and Jesse squealed in excitement. Tray squeezed her arm. He was ready to spoil her with whatever she wanted.
“Ready to model for me?” Tray teased, giving her ass a squeeze.
“You know it, babe.” Jesse winked, “Pick something out; I’ll wear whatever you want me to.”
Those words sent a shiver down Tray’s spine. He was his own personal dress-up doll, and he didn't hesitate to start.
“You’re going to look amazing in this,” Tray said as he held up a beautiful, flowing dress in rich emerald green with a plunging neckline. It was the perfect color for her skin; he could already picture how it would drape over her curvy frame.
“Oh, so pretty.” Jesse cooed, running her fingers over the fabric.
She slipped into the change room, and Tray strained his ears, listening to the rustle of fabric as she stripped off. He knew she had gone commando today, and the knowledge that she was naked only a few feet away sent a thrill through him. A moment later, Jesse emerged in the dress; the plunging neckline left little to the imagination, and the fabric flowed over her hips like water off a cliff.
“Gorgeous.” Tray beamed, “Do a little twirl for me?”
Jesse did so, giggling as the long dress fanned out around her.
“I love it! So freeing. You have no idea how nice it is to have my legs bare.” Jesse grinned. “I can't believe I went most of my life only wearing pants!”
Tray imagined those wide hips, perfectly cupped and supported by form-fitting closing and his mouth watered.
“Pants aren’t all bad, I bet I could find some that suit you.”
“If you’re paying, you can put me in whatever you want.”
Jesse giggled in delight, and Tray went in search of more options. He picked out a chic, form-fitting jumpsuit that caught his eye immediately. The rich midnight blue was the sort of thing people wore to clubs: the sort of outfit that left nothing to the imagination despite covering so much skin. When Jesse stepped out in it, Tray almost moaned. He could see the cleft of her ass and the peaks of her nipples through the thin fabric. It stretched over her in a way that some would think was obscene, but it just made Tray hard.
“We’re taking that.”
“It’s like a second skin; I almost feel like I’m wearing nothing at all.”
That did make Tray groan.
“You’re such a tease.”
“You love it.” Jesse winked. “Now, it's my turn to pick something. You stay right there.”
Jesse disappeared, and Tray settled back in his seat, already buzzing with anticipation. Another woman and her boyfriend appeared. She was stick thin and pale as snow. The boyfriend flopped down on the couch next to Tray and gave her a half-hearted smile as she stepped into the dressing room with half a dozen outfit options. The man turned to Tray and gave him a rueful smile.
“You’re stuck here too, huh? The walking wallet.”
Tray just chuckled.
“This was my idea.”
“What? Does your woman not take too long or something? I hate shopping.”
“I guess we’re just built different,” Tray grinned. “I could watch my woman try on outfits for days.”
“What do you think of this, babe?” The other woman asked as she stepped out.
She had a tiny waist and barely any chest; to Tray, she just looked like a pale string bean in jeans and a crop top. No wonder this poor man never enjoyed himself. As if on cue, Jesse reappeared with a bundle of fabric in her arms. She gave Tray a flirtatious smile before slipping back into the change room. A moment later, she emerged, and Jesse’s breath caught in his throat.
She was wearing a cropped halter-neck singlet decorated with gold rings and a matching pair of dark grey booty shorts. She stepped out, hands on her hips, and Tray felt his eyes almost bug out of his skull. The woman and her boyfriend both went red in the face, and before the other man could even protest, the woman dragged him away while Jesse laughed.
“Guess he just discovered waifs weren’t his type.”
“Who could want a woman like that with you standing there?” Tray said in awe, getting to his feet and circling Jesse. “Gods, you’re perfect.”
“You like this one then?”
“I love it.”
“There is one problem, though…”
“Oh?”
“It’s a little tight; I might need you to help me out of it.”
Jesse fixed Tray with a hungry stare, and a shiver ran down his spine.
“No problem.”
Somehow, they squeezed into the tiny changing room and closed the curtain. Jesse’s back was to Tray’s chest, so he could feel and look at her simultaneously. He hefted her breasts up, watching as the nipples peaked through the tight fabric of the halter top.
“I see what you mean, it’s pretty tight…” he whispered, nipping at the shell of her ear. “But not so tight I can’t slip inside…”
He brought both hands around to slide into the shirt, pressing his fingers against Jesse’s bare breasts and feeling her heart hammer beneath. His fingers pressed into her nipples, and a whimper escaped her lips, which Tray hushed.
“Not too loud now, beautiful. You don’t want to get us thrown out.”
“But it’s so good.” She whimpered. “Oh, Tray, you know just how to touch me.”
“I’ve had a lot of practice.”
Tray continued to play, pressing into the supple flesh and teasing until Jesse’s head fell back against his shoulder. Her hips bucked slightly, searching for friction, and he could see a small stain slowly forming over her crotch.
“We have to buy these now.” He chuckled.
“Mmmm…”
“What? No words?”
“J-just don't stop…”
“Are you about to cum for me, Jesse? Just from me touching your breasts?”
“Ah…M-maybe…ohhh.”
That was new, and Tray was delighted. She was trying so hard not to moan his name. Tray was rock hard and bucking his hips against the cleft of her ass. He loved how horny he made her. Having this curvy, black beauty in his arms, melting under his touch, was the ultimate turn-on. Her chest was rising and falling rapidly under his hands as she got close, and Tray redoubled his efforts, pinching and tweaking the nipples until Jesse’s whole body went tight.
“Oh fuck, I’m cumming…” She whimpered, biting her lips to keep from moaning as her whole body shuddered.
She relaxed back into him, and Tray grinned as he slowly removed one hand. The other stayed in place, gently pressing against her sensitive nipples while the other unzipped the front of her shorts.
“Oh, Tray…”
“Once more for me, babe.”
He dove his hands between her legs and felt the soft, wet heat envelop them instantly.
“Oh fuck.”
She was oversensitive from the first orgasm, and Tray knew just how powerful that made her pleasure. Jesse gripped his arm with one hand and slapped the other over her mouth to try and keep the sounds at bay. It was impossible, though, her breath was coming in loud, ecstasy-filled gasps that had Tray rock hard behind her.
“That’s it, cum for me, Jesse…”
She couldn’t reply, but Tray watched as her eyes rolled back in the mirror and her inner walls squeezed around him. A half-muffled moan escaped through the gaps in her fingers, and she leaned heavily into him as her legs went limp. Tray didn't stop, though; he kept pumping his finger in and out, making her squeal and squirm.
“Let me get you back.” She whispered. “Oh fuck, I can’t…it’s too much.”
“I don’t want your hands…” Tray murmured, “I want this.”
He made a show of running his fingers down the length of her passage and back up again, pressing a soft finger pad to her G-spot. Jesse whimpered as he removed the finger and slowly lowered her shorts, revealing that plump, beautiful ass that he loved so much. Next, he removed the shirt so that her breasts could hang free as she braced herself against the mirror. This was the ultimate show; he could grip her hips and take her from behind while still having a perfect view of her breasts and face.
“You’re going to cum for me again, Jesse.”
“I don’t think I can…”
“We’ll see.”
Tray unzipped himself and took out his length, rock hard and ready for her. She was so wet there was no resistance as he slowly pressed into her hole, sliding up to fill her and watching in delight as she shuddered.
“So good…it’s too good, too much…”
Tray just grinned.
“Too bad.”
And with that, he began to thrust into her, fast and hard, the way she liked it. Jesse braced herself against the mirror, but her body still moved with the force. Her heavy breasts swung back and forth with each thrust, and Tray had a front row seat. It was hard not to cum immediately, but Tray knew he had to hold on. He wanted to take Jesse apart. Show her that nobody would ever be able to give her the pleasure he could.
Her pussy was so tight and hot, despite already cumming twice and her ass was so soft under his hands. Even after all these weeks of experimenting and sex he wasn't over just how amazing it felt to fuck his dream girl. He’d be lying if the idea that that wanton, moaning, sexy mess of a woman used to be a man either. It was the ultimate power fantasy. Jesse was the whole package.
“Oh fuck, I’m close, oh fuck I can’t-!”
“Cum for me, Jesse. Now.”
This time, she wasn’t able to stop the wail from escaping her lips, and Jesse came again. Her passage clenched around him, and Tray saw stars as he fell over the edge with her. His balls tightened as they pushed seed straight through his shaft, and pleasure clouded his vision. By the time he came back to himself, they were both a sweaty mess. Jesse half collapsed against the mirror, her naked body pressed against the cool glass.
After a moment, she muttered, “There is no way we were quiet enough to go unnoticed.” Tray laughed.
“Yeah, I think we’d better pay and get out before security comes.
With a playful laugh, they finally pulled apart, and Jesse put on the green dress from before. Much as they both wanted her back in that shorts and halter neck combo, they were both far too soiled to be worn right now.
They stepped out of the change room only to find the store manager waiting for them with a sour look on his face. Fortunately, they were still allowed to leave with the outfits Tray had picked out. However, his wallet was considerably lighter than he planned, thanks to the fine they incurred.
“Totally worth it.” He said with a contented smile as they walked out. “I am sure we can shop in other places in the future.”
“Agreed. So, what shall we do this afternoon?”
“Hmmm, beer and a game?”
“That sounds perfect.”
Once again, Tray silently thanked the witch who had made this all possible. Not only did he have his dream girl, but she liked all the same things as him and had the same one-of-the-boys attitude Jesse always had. Plus, it was pretty fun having a girlfriend who could take him drink for drink.
“Hey, Jesse…”
“Yeah?”
“What are we now?”
The light mood suddenly vanished, and he felt her grip on his arm tighten slightly.
“I’m not sure. Why?”
“I guess. I was wondering what to tell our friends at the office and if it would be okay to call you my girlfriend. Or if that would make things weird for you.”
Jesse stopped for a moment and sighed; Tray felt a stone form in his gut: had he just ruined everything?
“The truth is…I’m not sure who I am anymore,” Jesse admitted. I was trying to take everything calmly and easily, but it’s still weird being changed this way. Sometimes, I feel guilty enjoying all this girly stuff.”
“Why?”
Jesse shrugged, and Tray pressed his lips into a thin line.
“Well, how about this: we’re best friends.”
Jesse giggled.
“I think we’re a bit more intimately acquainted than best friends usually are.”
“Yeah, well, we’re really good best friends.” Tray chuckled, giving her a quick peck on the cheek. “I’m happy ot indulge whatever whims you have, experiments, all that, and we can be friends and fuck and whatever we want to.”
Jesse put her arm through his again and held him close.
“You know, Tray, you’re actually really sweet.”
“Gross.”
Jesse rolled her eyes but didn’t move away. There was something nice about the heat of her body seeping into his; it felt intimate and not in a sexual way. Tray felt a flutter of something in his chest; it wasn’t love, but maybe the beginnings of it. He had no idea what to expect in the future, what direction their relationship would go, but he was excited to find out. Tray wrapped an arm around Jesse’s waist and took a moment to savour how right it felt there. Maybe they would be more than best friends one day, but for now, this was enough.
