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Changed For The Better (DarkDreamer9110 x kinky-sub)

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DarkDreamer9110

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Joined
Feb 22, 2013
Lucas Gray had finally gotten free of his family. Now in college, he was finally at a point where he could start working things out. Now if only he could get up the courage to start. He had spent nearly half an hour already trying to get up the nerve to go into the women's clothing section. He would walk by it, pause indecisively, wander off somewhere else in the store, and come back, staring longingly at the clothes within.

So close, and yet the fear was there. The shame, the transphobic rhetoric, the toxic masculinity, it all made the idea of what he was considering nearly impossible. All he had to do was walk in, find pretty clothes, buy them and leave. Plenty of guys probably shopped for their wives, girlfriends, daughters, sisters. What was he scared of? That someone might guess, that he might be mocked and bullied? There were plenty of women he could be shopping for, as far as anyone knew. But he was trying to shop for himself, and that somehow made it taboo, forbidden.

How hard could it be, really? He was paused outside the section again. "Come on, Luke. Just do it." He told himself quietly. And yet he remained frozen, unable to enter.
 
Alice Reed had just entered the store ten minutes ago only having come here for a few things intending it be a quick trip before heading back to her apartment and relaxing for the rest of the day. That was until she saw Lucas catching him staring at the women's clothes before he wandered off again to repeat these steps again. Looking at him she was reminded of an old childhood friend who told her that first time shopping for her true self was awkward and anxiety inducing. She didn't want to make any assumptions about the him and she was of the opinion that clothes don't have a gender.

Alice almost walked away wanting him to find the courage on his own but then she spotted two Karen types near her and could hear them whispering about getting security called to this section. She shot them a dirty look as she approached Lucas gently placing a hand on the small of his back."Relax and just play along." She whispered to him gently not wanting to startle the poor thing. She was about five years older than him as she was about to graduate college and begin a career soon something she was thankful to already have lined up. " I told you wait for in the shoe department honey. What were you thinking of getting for your sister's birthday?"She asked projecting a bit so the two other women nearby could hear her. They rolled their eyes softly only half buying it but it was enough to get them to wander off to another section of the store.

Keeping her hand on his back Alice started walking towards the women's section coaxing him along to finally begin shopping and hopefully ease some of his nerves. "I'm Alice by the way nice to meet you."She said softly breaking contact with him once it looked like the two were alone in the section. "So do you know what size she is or do you need help figuring that out?" She asked smiling at him softly.
 
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The hand on his back and the gentle whisper got a confused glance from Lucas, but he was relieved as the slightly older woman seemed to give him an excuse to enter the section, in fact goading him along to it. He smiled at her as she spoke. "Lucas. Nice to meet you, too. And thanks. I, uh, needed this." He said softly.

Her next question got a shrug. "I, uh, I'm not actually entirely sure. Never got the chance to figure it out." He said. "So, yeah, I, uh, have no idea what I'm doing."
 
"You're welcome Lucas, and no worries I saw you struggling. Just take it one day at a time. And a good tip if you act like you don't belong people will think you don't, so fake it till you make it."She joked walking the section with him trying her best to turn this day around for him as best as she could. "Let's see if I remember correctly for bottoms just take twenty of your waist measurement, as for tops we can eyeball it and do some fine tuning once you try them on." Alice explained tapping a finger on her chin lightly.

"Also something you may not be used to but check the pockets to see if they're real." She joked motioning to her own jeans which looked liked it had a few but non of them could hold more than a tooth pick."Don't get me wrong I love how i look in these but not always needing a bag would be nice" Alice added grabbing some leggings off the shelf and holding them up to him as a suggestion. "So are you looking for complete overall or just something more fem?"
 
Lucas nodded as she explained the sizing, then his brain finally caught up to things, and he shook his head fervently, almost more by instinct than anything. "No, I, uh, look, I'm not ... They're, uh, not for, uh ..." He sighed, then glanced at her. She already seemed to have pegged him for someone looking for himself and not a woman, so no point in denying it. "I don't know. This is all new to me." He said. "Don't know what I like or anything. How could you tell I wasn't actually shopping for someone else?" He asked.
 
"Sorry my bad, I shouldn't have assumed that you were looking for yourself. " Alice apologized truly feeling bad about it. " you looked lost, and anxious. Someone buying a gift would have just waltzed in. Plus seeing you reminded me of a friend of mine. The sizing and fits were all new to her too."Alice explained softly hinting that she had a vague idea of what could be going through his head and that she was hear to help.

"Finding your style will take time, best to start with some basic items and if something more extreme jumps out at you try it own." She added gently placed a hand on his shoulder." My friend also mentioned she could have used a friend shopping from day one."
 
Lucas shook his head as she apologized. "No, you were right. I just ... Like you said, I was acting like I didn't belong. I mean, it's not that ... I don't know if I'm, like, actually not really a guy ... All I know is doing this is something that my parents would disapprove of. But I can't just keep acting like this isn't an interest of mine, like I don't need to try this. And thanks. I could use a friend for all this."

He took the leggings she had offered, giving them a look over. "I dunno. What do you think?"
 
"It's okay you don't have to have all the answers right now. They'll come to you in time." Alice said squeezing his shoulder softly doing what she could to comfort him. "Yeah parents suck, but you're an adult now and don't need their approval. And there's nothing they can really do to stop you."

"Well if this is just an interest there's no harm in exploring it while you figure things out." Alice said starting to walk around again running her hands on a few things."So I'm thinking we keep it simple for now some skinny jeans, add a bit more color into your wardrobe, you could go a bit more fem for things you wear around the dorm or things people aren't gonna see like your underwear." Alice said as she began picking up a few pairs of tighter jean and handing them to him, as well as some softer tee's that had a deeper v cut on them. "What's one item you've wanted to try on?"
 
Lucas smiled at Alice, nodding. "I know. I just ... What if it's more than just wanting to wear pretty clothes and makeup? My family ... I don't want to lose them." He said, then shook his head. "Sorry. I know you probably don't need someone dumping their shit on you."

He smiled again at her next question, going over to a cute little black dress and reaching over to touch it, then took it off the rack and held it up. "What do you think? Too ambitious? Even just for at my dorm?"
 
"Then it's not, what's important is getting to be yourself." Alice started pausing as she had a sense of pain when it came to his family. "Look you're not losing them, they're loosing you if they don't decide to embrace the new you. I've lost contact with my aunt she hated how I dressed and immoral to date girls." She added trying to relate with him a bit.

She was happy to see him wander off and pick out a dress. "No, you'll get there even if it isn't today. Plus it'll look super cute on ya." She said with a smile holding it up to him."and these will make it pop." She added handing him a pack thigh high stockings
 
Lucas smiled as she told him it wasn't him losing his family, but them losing him if they couldn't accept the new him. He nodded as she related that she'd lost contact with an aunt over her style and sexuality. "That sucks." He said.

Her encouragement got him nodding again, and he smiled more as she handed him the stockings. He looked at her, then glanced longingly at the changing rooms, frowning as he did so. "I, uh, guess maybe I should, uh, go ahead and get this done." He said.
 
Alice caught him frowning a bit seeing that this part was gonna be hard for him. "Give them back to me for a moment." Alice said taking his small pile of clothes as they walked towards the dressing rooms. She grabbed some guy's clothes and placed them on top of what he picked out. "Don't worry we'll put those back." She added as they headed into the hall with the changing rooms.

Thankfully the store didn't have anyone posted there at the moment so Alice coaxed Lucas into one of the bigger rooms before trailing in behind him."I won't watch you undress just tap me when you're in your new clothes" Alice said with a playful wink doing what she could to keep him distracted.
 
It wasn't hard to figure out what Alice had in mind as she added some guys' clothes onto the pile, hiding the girls' clothes under them before ushering him towards the changing rooms. He nodded as she spoke, assuring him that she wouldn't be watching him change.

After she was turned around, he stripped down and, hesitantly at first, tried on the first set of clothes they'd picked out. He took a look at himself in the mirror, and couldn't help the gasp of surprise that escaped his lips. He looked ... Good. And he felt just as good. He tapped her on the shoulder, smiling widely. "What do you think?" He asked.
 
Alice was already smiling as she had caught his gasp seeing himself for the first time in clothes that he wanted to be in. " Judging by your smile you love them. As for my thoughts you look super cute in them. They're subtle but does wonders to bring out that wonderful smile of yours. Plus you look good in brighter colors "Alice said after she turned around feeling the tap on the shoulder. "How are the fits nothing too tight or loose?"She added walking around Lucas smiling just as wide as it was nice to see him happy and that the anxiety and bulid up was for nothing.
 
Lucas blushed as Alice told him he looked super cute. He nodded at her next question as he tested the range of motion the clothes provided, stretching and taking a few steps. "Yeah, they're a pretty good fit." He confirmed, the smile growing.

"Thanks. For helping me get over that anxiety and take the plunge."
 
"Good, glad it fits. We can snag a few more before checking out if you want." Alice said smiling back as she was happy she could help him this much in discovering himself.

"You're welcome, we all need a hand sometimes, and if you want to do this again or need space to be yourself let me know. I live alone off campus."
 
Lucas nodded again as Alice spoke. Her reassurance that he was welcome at her place if he needed a safe space got another blush and an emphatic nod. "I will." He said. "I guess we should trade numbers."

After trying on the next few outfits they'd picked, and feeling more and more comfortable with each one, Lucas looked at Alice as they headed up to the register. "Seriously, thanks. Again. For everything. I can't wait to hang out with you sometime. Maybe ... Maybe next time we can try some makeup?"
 
"That'd probably help unless you wanna just leave it to chance." She joked taking his phone from Lucas putting her number in it with a heart next to the name. After sending herself a text from it she handed it back. She also added in her address too. "All set I put my address in, just in case need or want to have something shipped there. " She said as the two left the dressing room taking the clothes back.

"You're welcome and ofcourse. Ooo I'll build you kit and you can come over. I can teach you the basics."She said smiling brightly. Once they were checked out she escorted him out. "Well guess this is goodbye for now, take care and proud of you for starting this journey." She said giving him a hug before giving him the bag of clothes. " if you need something sooner or just wanna chat text me"
 
Lucas smiled as Alice mentioned putting her address in. "Thanks. Sounds good." He said, taking his phone back and pocketing it.

When they were ready to part ways, he nodded. "Yeah. I'd like that. Maybe this weekend? Give you time to get things together?"
 
The next few days kinda flew by for Alice as most if her classes she could do in her sleep. While her other friends were busy with projects she was happy to have Lucas as a friend as the two spent next few days texting back and forth a fair amount. As promised she went out a d built him a starter kit of makeup including the basics like some lipsticks both liquid and traditional, mascara eyeliner, foundation, concealer and eyeshadow pallets. One pallet being more nude colors and the other having one of each color with a shade lighter a d darker. She also grabbed red pigment corrector to help with any shadow he had from shaving.

The morning of she got up early and did her errands getting him a plain black leather bag to put it all in. Once it was built ahe placed it on the counter and went to do her morning workout though lost track of time. She was back right before he would arrive but needed a shower. " hey my work out ran late I'll leave a spare under the cactus. Just come in and make yourself at home. See ya soon." She texted before she jumped into the shower.
 
Lucas enjoyed the next few days. He and Alice texted frequently and even talked a few times, he had started looking into the local queer community both on and off campus, and he had found himself taking advantage of every moment of freedom he had without his dorm mate present to dress up. He'd spent hours trying on different combinations of the outfits, modeling in front of the mirror.

One day, he'd even experimentally worn and stuffed one of the bras with socks, thrown one of the tops over it, and spent several minutes staring at himself, utterly dumbfounded. It had been shocking how good he thought he looked with the stuffed bra adding some feminine curves to his figure, and more shocking how it had made him feel. It was the same feeling as when he had first tried the clothes on with Alice, only more powerful. Almost ... Right.

After that, he could hardly wait to see how good he would look with makeup done, and found himself eagerly anticipating the chance to spend time with Alice working on his appearance.

He had almost been at Alice's apartment when she texted him that she had been running late and where to find the spare key to let himself in. He smiled. Maybe he'd talk to her about joining her for her workouts in the future; he'd been thinking about starting working out himself, and if he could have a workout buddy to show him what girls did to look good and stay fit ...

He shook his head to clear it. Where had that come from?

He found the key without trouble, unlocked the door, and walked in. He set his bag (filled with a couple of outfits) down next to the couch and sat down to wait for Alice.
 
Alice didn't exactly rush through the shower though but still took what time needed to get herself clean. She could hear the door unlocking and closing smiing a bit as she was looking forward to today too. To see how he's been adapting to the new clothes but also she loved seeing him genuinely smile and begin to love himself more and more. As she finished up her shower she got changed into a pair of black shorts and a white tank top. Her bra showed through a bit but didn't care as if the too were gonna go somewhere she could change quickly.

"Hey good to see you, glad you found the place alright." Alice said coaxing him up off the couch to give him a hug for a moment before letting go. "Okay the black bag on the table is you new kit, a little basic and manly but given your situation I thought it worked the best." Alice said picking up the bag and opened it allowing him to look through. "Also it's nothing super fancy still good products I still use half of them. But it's better to practice with the drug store stuff before buying the really good stuff." She explained.

"So I think the best way is I'll do your makeup here and when were done with you you can watch me mine. that way can see how it should look on you but also ways to apply it to yourself. Sound good?"
 
Lucas returned the hug with a smile, nodding as she explained the new kit and her reasoning for going the route she had with the selection. She definitely seemed to understand his situation. His expression briefly wavered as she called it a bit manly, but the smile returned as he sifted through the kit.

As she explained the reasoning behind practicing with cheaper stuff, he nodded again. "Sounds reasonable." He agreed. When she laid out her plan and thought process, he nodded again.

"Makes sense. Do you, uh, mind if I get changed into something more, uh ... comfortable first?" He said, picking up his bag of clothes and glancing towards the bathroom. "I, uh, figured we should see how the whole thing looks, clothes and makeup and everything together."
 
Alice caught his smiling wavering as she cursed silently in her head making a note to avoid any words like that when describing things for him. " Of course go get changed, I'll be here setting up." Alice said with a smile. As he walked off into the bathroom she began pulling out the make up setting them up in stages so to make it a but more smooth. Once she was fully set up she leaned back into the couch planning out look she wanted to give him.
 
Lucas nodded as Alice approved him changing. He had opted not to make the walk to Alice's apartment in femme clothing for the obvious reason that he wasn't comfortable with going out like that, at least not yet. But knowing that Alice was a safe space for him to dress up and explore this side of himself was a reassurance, especially knowing that there was no chance of someone else catching him dressed up and judging him for it.

In the bathroom, he went through the outfits he had bought, settling on the little black dress he had bought earlier with Alice. Slipping the bra on first and stuffing the cups with a pair of socks each, he then pulled the dress on, and took a few moments to admire himself in the mirror before heading back into the living room. "Okay, let's do this." He said, trying to sound more confident than he felt.
 
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