Getting Ready for a Change

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Chrissy Crawford gets ready to become a woman.
3.7k words
4.08
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Part 1 of the 2 part series

Updated 09/24/2022
Created 05/11/2013
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Setanta84
Setanta84
14 Followers

Chrissy Crawford was psyched. It was the eve of her twenty-first birthday and she was planning to get hammered. Yes, now that she was legal, she was going to get hammered for the first time ... the first time with the sanction of the state, at least. Her parents had given her free reign of the house for the whole weekend for the occasion, with the little proviso that the party was to be supervised by her older brother, Matt. Matt was cool, he had been able to legally drink for a year now and Chrissy was sure that their parents did not know how much he liked to party. He was not the kind of person to get in the way of his little sister having a good time. She was going to get the most out of this celebratory weekend.

Smiling at herself in the bathroom mirror, Chrissy--'Cee Cee' to her friends--stood five feet and two inches tall barefoot and five and a half feet tall in heels. She almost always wore heels. Chrissy's eyes were big and brown and shaded by naturally long, thick lashes. Her lips were small but pouted just a bit at the corners, making her virtually impossible to resist when she begged for something. She was slender and slightly pale in complexion, with perky breasts that just about fit behind her hands when she cupped them. Chrissy wished she had more of an ass, but genetics just did not have that in the cards for her. Curling her long chestnut brown locks with a curling iron, she admired herself and hoped men would admire her in the same way tonight.

Her twenty-first year would be a big one for her sexual development. Chrissy had only had sex with two people before tonight. She was going to make a good faith effort to broaden her experiences. The beginning of that effort had been inviting nearly every attractive guy in the zip code to her party, through her friends and social media. If her experience was going to broaden with the help of perfect strangers, that was fine. If it happened with friends that was fine by her as well. But it was going to happen. Chrissy was a bit nervous about all this despite herself. She was going to need a bit of liquid courage.

Unplugging the curling iron and carefully putting it aside, Chrissy shuffled into her bedroom. She contemplated what she would wear for her party. Guests were set to start arriving in an hour. Matt was busy downstairs getting the food and drinks together. She loosened her curls with her freshly manicured fingernails on her way to her closet, wearing only the black bra and panties she had put on after her shower.

Crashing noises suddenly came from downstairs. Chrissy sighed, calling down to Matt to come upstairs for a minute. She looked through her closet as she waited for him, not bothering to cover up. Chrissy was comfortable with her body. Besides it was only her brother. She wanted an update on what he had been up to downstairs. Matt told her he would take care of everything. She was counting on him to make this a very special birthday weekend for her.

"Matthew, you are to spend this weekend supervising Christine's party." That was verbatim. Their parents always used their full names--even though neither of them preferred that--with perfect but flat delivery, like goddamn sociopaths. They had ordered Matt to do this, they had not asked. He was pissed. Even though he was a graduating college senior, they still treated him like a toddler because he lived at home. Matt did not know who Chrissy was inviting or how many people and he did not care. He was going to let her do whatever she wanted. Fuck his parents.

" I go to school on a fucking football scholarship, I'm fucking six feet tall, I am a goddamn Chemistry and Earth Sciences double major graduating on motherfucking time; I am a motherfucking grown-ass adult, fuckers," Matt grumbled as he stomped up to Chrissy's room. Due to the tight schedule he had to maintain to juggle his responsibilities to the team and the requirements of two majors without crapping out on either, Matt had had only four previous sexual partners in his entire life. "Fuck it, if they want to treat me like a fucking child, I'm going to act like one. At least one of Chrissy's little friends is getting fucked by a fucking blue-eyed, handsome football player tonight."

After he had arranged the assorted cases of beer and liquor and the food tables, Matt had bumped into a stack of wine while moving some of the furniture into the garage; all the boxes crashed to the floor and some of the bottles had broken. Matt hoped Chrissy either had not noticed or at least had the good sense to pretend she had not noticed as he approached her doorway. "Yeah Chrissy," Matt said, just before she stepped from the closet and he saw she was only wearing a bra and panties.

Chrissy turned to face Matt, tilting her head slightly to the side, causing her loose curls to fall around her shoulders.

"I heard a noise downstairs ... what happened?"

She roamed his body with her eyes, forgetting about her clothes for the moment, approaching him with concern.

"You're not hurt, are you?"

Chrissy gently ran her fingers along his arms, checking for any obvious marks and Matt just watched, slightly stunned by both the view and the contact.

"Everything is fine. I just knocked over some boxes heading to the garage. I'm fine, sis."

She smiled up at him, continuing to lightly rub his arms. "My big brother's working so hard for me, isn't he," she cooed. She leaned against him, wrapping her arms around his neck, tip-toeing up to peck his cheek. "You're the best, Matt." Matt nervously smiled, figuring she was acting like this because she was excited for her party.

"Yeah, I am working pretty hard; It's all set up and ready to go, and there is a surprise for you down on the counter," Matt said with a grin. While setting up for the party, Matt had found their parents' stash of top shelf liquor. The best bottle of bourbon and the best bottle of vodka were on the counter as his present to his sister.

"You got me beer? Tell me you got me beer!" She looked at him with pleading eyes, anxiously tugging on the back of his neck. Matt started laughing. "You'll just have to wait and find out. That's the point of a surprise silly," he said as he backed out of her room slowly.

"Maaattt," she followed him to the doorway, pouting. "Can I please have a beer now? Pleeeasse?" She bit her lip, batting her eyelashes. "Just one ... just a tiny sip?" She took his hand in hers, swaying from side to side. "Please, big brother?"

Watching her pout and give him those puppy dog eyes, he let out a sigh. "Alright, alright. Fine. Just a sip though!" He started walking towards the kitchen.

She squealed with joy, letting Matt go get her beer. "Thank you!" She turned on her heel and headed back into her closet to sort through her clothes once again. She had to look hot. No, she had to look better than hot. Fuckable. That is what she was going for. "Hmm," she wondered if she shouldn't wear a bra.

Matt went into the kitchen and grabbed a beer out of the refrigerator. He briefly flirted with the idea of bringing Chrissy the liquor instead but thought better of it. A surprise like that was best for the party proper. He grabbed a Pyramid Heffe for her and a Sierra Nevada Torpedo for him and made his way back up to his sister's room.

Chrissy unclasped her bra, letting it drop to the floor in her closet. She folded her arms across her chest, covering her nipples as she browsed her clothing selection with just her eyes. She heard Matt returning to her room and called to him from inside the walk-in closet. "I don't have anything to wear," she sighed. Nothing she had was quite sexy enough. Nothing really said "Come here, I'm down to fuck."Matt sat down on her bed.

"Ha, well just take your time. You have plenty to wear, sis."

Stepping out of her closet, Chrissy playfully covered her chest as she stood in front of her brother. "I just looked," she moaned. "Everything I have I've worn a million times in front of my friends ... maybe I should just go naked."

Matt's eyes widened as he saw his sister walk out of the closet with just her arms covering her breasts. "Yeah that's not a good idea," Matt said as he nervously quaffed his Torpedo while trying to casually trying to keep a sideways glance as his sister's unexpectedly tight little body going. "Who cares if they saw you wear it a million times. Does that really matter?" Disdainfully nodding, Chrissy went about setting him straight.

"Of course it matters. You're such a guy to say that."

Chrissy noticed Matt's eyes widen from slightly behind the bottle at the sight of her almost bare breasts. She couldn't help but like the attention, even if it was from her brother.

"Help a girl out, big brother," she nearly whispered in an oddly seductive tone. "If you were a guy at my party, what would I have to wear to get you to go from wanting to fuck just any girl at this party to trying to fuck me?"

Matt almost choked as he heard what she said. "Well to be honest, anything you wear you would look good in."

Cooing at her brother as she approached him, Chrissy smiled. "Aww Matt." She carefully freed one arm from her breasts, keeping her nipples out of sight with the other arm stretched across. "Yeah, you're probably right," she gently placed her fingers around the neck of the beer she assumed was meant for her, brushing Matt's fingers in the process of taking the beer from him. She grinned, lifting the beer to her lips, taking a big sip. "Mmmm."

He was trying his best not to glance at her chest as she removed one of her arms and took the bottle. Matt noticed she was doing her girlish best to chug it. "Hey, hey, slow down now, you have guests to entertain, sis."

Chrissy giggled when Matt told her to slow down. That was the opposite of what she planned to do tonight. "Yeah, yeah, sure." She took another big swig, over-tilting the bottle a bit, causing some beer to slid down from the corner of her mouth. "Mmm, oops." Watching her pour it all over herself, Matt laughed a little bit. "I know that's not your first beer, but it looks like it."

Rolling her eyes at him, Chrissy licked the trail of beer that dripped down the corner of her lips. "Well, good thing I had it now then." She turned from him, flipping her hair over her shoulder, heading back into her closet. "Hmm, I maybe I'll wear a skirt. A really tiny one so I can barely bend over," she said while making a wild and naughty expression towards Matt.

"Like I said, you would look good in anything." Matt watched as Chrissy re-entered the closet. "You're not making me stay up in here for a motherfucking fashion show are you?"

Gasping, Chrissy nearly squealed her response. "Oooh, that's a good idea. Don't move!" Matt sighed and rested his forehead in his free palm as she told him not to move. "Should have kept my motherfucking mouth shut." Chrissy grabbed a few things off their hangers and started to get dressed. Pulling on a short black skirt that hugged her hips and a dark purple halter top that really accentuated her perky breasts, she smoothed her hands over her sides and stepped out to show Matt. "What about this?"

As Chrissy stepped out of the closet Matt immediately noticed how the skirt hugged her hips and how her top showed off her breasts. "Uhh ... looks good, sis." He had a hard time keeping his eyes from roaming down her body again. This is your goddamn sister standing in front of you, motherfucker. Save these thoughts for her motherfucking friends. But Matt found he could not stop thinking how good she looked or what he would like to do to her.

Pouting, Chrissy was profoundly underwhelmed by Matt's reaction. "Looks good? That's all?" She moved closer to him, determined to get a better reaction. Turning in profile, Chrissy bent over steeply, making a lewd display of herself. "How's my ass look when I do that? Can you see my panties at all?"

Matt began to wonder why she was doing this. But those thoughts did little to restrain him. He could not help himself, Matt glanced down at her ass and spied the fringe of her little panties and the bottoms of her tight cheeks on full display. "Fuck, Chrissy. Yes, I can see your panties. Your ass looks fine ... I guess. It's just a little weird with you asking me these questions, on the account that you're my little sister."

Amused. Yes, that was the word. Chrissy was amused to see her brother so uncomfortable. "It's just a little skin, Matt. It's not like I asked you to touch me or anything." She glanced at him, wondering how he'd react if she did ask Matt to touch her. Chrissy shrugged it off for now. Standing up, she squeezed his thigh and smirked. She was fairly sure her fingertips had just grazed the length of a hard-on for the first, but hopefully not last, time this evening.

Matt felt as hung as he had looked in their shower most of the mornings of their entire adult lives. At first, it had been an accident. Chrissy had been in a rush to get to class the first morning of her senior year in high school and dashed into the bathroom to get her compact. She had not expected to find Matt lathering his hair with shampoo while facing the open door of his shower. The kid had a body of a Greek god, not an ounce of fat, not a single imperfection. But he had the cock of a Roman grotesque. It was huge. Fucking huge. Thick. Beautiful. Chrissy had been ashamed when she realized her pussy was clenching and her thighs were wet. She had backed out of the room as discreetly and quickly as possible and rubbed her pussy during the entirety of the drive to school.

She had had to make herself climax twice before she was decent enough to make it through the parking lot. It was the start of many mornings of walking by an "ajar" bathroom door or "forgetting" her smartphone on the counter corner directly opposite the shower. Her smartphone that had a camera, water-proof case, and a tendency to be leaning against the wall with the camera side facing the shower.

Chrissy resolved to head back to her closet and continue this little game. "This outfit is going into the Maybe pile; I'm gonna keep looking." She hoped she had not sounded weird just then, those memories had gotten her really worked up. "Alright, well, while you do your fucking princess thing and dig out another outfit, I'm gonna go grab another beer," Matt groused. Heading downstairs, he felt like he needed something stronger than a double IPA after that little show. He grabbed another Torpedo, but it was going to be a chaser for a shot of Everclear this time. If he learned one thing during the few nights he allowed himself to go out during college, it was that Everclear was a useful response to troubling thoughts.

After taking the shot and chugging half the beer he opened, Matt grabbed another and headed upstairs. Pausing for a second before re-entering her room, Matt thought over why Chrissy would be doing this too him. Hopefully, she was just really excited for her party and didn't yet fully understand the effect she had on men. He made his entrance and sat back down on her bed.

While Matt was away, Chrissy had changed her underwear, putting on a lacey black pair with a hot pink trim. She grinned evilly. This will make Matt even more uncomfortable than the last pair did, I can't wait to see the look on his face. Chrissy no longer cared if this was inappropriate, if she ever had. She was having fun. That was the whole point of her big birthday weekend after all.

"Back?" She called from the closet, already dressed in a tight, light gray mini dress with her new panties underneath. "I think this outfit has potential," she said, sauntering out of the closet, posing in front of him.

Finishing off the first of the two beers he brought back with him as Chrissy came out of the closet, Matt took in the criminally tiny dress his sister had chosen to present to him It hugged her body so nice. It really shows off her luscious little curves. Chrissy was still was not wearing a bra and Matt could tell her nipples were hard. "Wow." Matt cracked open the second beer. They still had a good amount of time until things got going and neither of them seemed in a rush to leave.

Grabbing the Torpedo, Chrissy stuck her tongue out at Matt. On the first day of my twenty-first birthday party, the asshole grabs two beers for himself and not a single one for me. Typical fucking male. Sipping it carefully, not wanting to stain her dress, another mischievous thought came to her. That evil smile once again crossed Chrissy's lips.

For a white jock from a privileged family, Matt had odd tastes. He was one of those people who really got into The Wire half a decade after it left the air. He even had started talking like the "harder" characters. It could be worse, she consoled herself. Matt was a kid using his natural talents to make good and insisted on rising on his own steam, working for what he got. The show definitely had a soft spot in its heart for kids like Matt. The character he reminded her of was Nicky Sobotka. It wasn't like he was fucking Barack Obama, proudly announcing that he loved the show and Omar was his favorite character. That just proved he either did not actually watch the show or did not watch it closely enough to understand the show held low opinions of both politicians and Omar. What if I danced for Matt like one of those club girls on The Wire?

Slowly Chrissy started to move her hips to a beat in her head. She turned her back to Matt and again bent over deeply, again making a lewd display of herself. This time, however, she did it slowly, gracefully, and seductively, like an experienced dancer at a higher-end club. She started to shake her tight little white ass in his face in time to the music. She closed her eyes and imagined his hungry eyes on her gyrating ass and on her little black panties.

Chrissy started to fantasize about him taking it all in and knowing it was all for him. She started imagining him getting hard and began fantasizing about the dimensions of her brother's cock. That huge, beautiful cock. Chrissy was now re-imagining herself entering the shower that morning, only in the safety of fantasy, she did not run out of the room. No. Chrissy imagined herself getting on her knees and taking that monster in her mouth and down her throat. She started to get wet. Very wet.

Matt's eyes widened as she bent over. He could see right up her dress. She had changed into a tiny, nearly sheer pair of black panties. As she started shaking her ass he could not take his eyes off it. Matt sat there in rapt awe, half-heartedly trying to snap out of his sister's lustful spell.

She bent over more, backing up in front of him, almost enough to press her ass against the front of his pants. She smiled, reaching back to rest her hands on his knees when she noticed him staring at her panties. "So, Matt, did I succeed in going for the 'fuckable' look?"

Her brother could not answer her, he could only stare at the spectacle Chrissy was making of herself. She smirked, playfully bumping her ass against his crotch just for a moment. It sent a jolt through Chrissy's whole body. Something had hit her pussy when she did that. Something hard and large. Chrissy's grip tightened on Matt's knees as he weakened and she started a nearly involuntary circular grind of her mound on his bulge."Yes or no," she nearly hissed into the air. Chrissy glanced back at her brother, giving him a sweet yet dangerous smile. "I need to know, Matt."

Panicked, Matt grasped her wrists and hoisted his sister of his body "Y-yes. Okay? Fuck. Yes, you are definitely a fucking fuckable female. If I weren't your brother, I would fuck you. Now that you got your answer, does that mean the motherfucking fashion show is over?"

Setanta84
Setanta84
14 Followers
12