Buying a dress, wearing a dress

Reina gave Jerri’s arm a light squeeze, practically glowing as she steered her further into the boutique. The girl needed a lot of work, but was already coming along nicely, that and her willingness to spend money made Geraldine her favorite client. The waist trainer was doing its work already, giving her that delicate inward curve, softening her shape beneath the pink SpaFreu top and in time it would help her in many ways to achieve the body she wanted. ‘Now came the fun part.’ Reina told herself.

“Leggings, tops, a pair of shoes… We have the meal replacement shakes, and the waist trainer…” Reina slowly went over what they had taken care of so far before nodding to herself. “Since we’ve got the basics out of the way, ” Reina said sweetly, “let’s pick out a few specialty pieces.”

Reina saw some hesitation in Jerri’s expression. Reina could practically feel it in how the girl’s shoulders tensed. ‘I feel so bad for her… I can’t imagine what she had to endure growing up, I am absolutely going to help her get comfortable in her own skin and expressing herself fully.’ Despite her hesitation Reina was happy when the girl followed her over to another rack of clothing.

Two dresses hung prominently on side-by-side mannequins, both tailored to flatter the feminine form while still fully gym-appropriate. The first was a clean, white collared tennis dress, soft polo fabric with short sleeves, a fitted waist, and a flared skirt that stopped mid-thigh. Something similar to what Reina herself was wearing. Simple, sporty, elegant.

The second dress was even more fun far as she was concerned, soft lavender, high neckline, with thin crisscross straps that bared the shoulders and upper back, making it perfect for spin classes and dance cardio alike. Reina reached out and gently lifted both dresses off the rack, holding them up teetering her hands side to side as she moved the dresses about slightly next to her. “I just love these, do you think their cute?”

“Umm, yeah, I mean… you look great in what your wearing. Did…” They had already gotten him more gym clothes and Jerry didn’t know why she was showing him the dresses, but then he believed he was able to put the pieces together. “Did you want me to buy them for you?”

His eyes went to the price tags, seeing they were more expensive than the leggings he had gotten. Jerry had never been around a girl so forward that they directly asked him to buy them outfits. “Maybe one… they are a little pricey.”

Reina laughed. “Sure if you just look at the price, but come on Jerri, with girl math they are a bargain.”

“Girl math?” He asked, wondering if that meant from her perspective of him paying for it meant it was cheap and hated himself a little for thinking negatively of the pretty young woman.

“Here.” Reina pressed both dresses into the girl’s chest. “The leggings we got you are thirty nine, ninty five, the branded tees are twenty eight ninety nine. So for an outfit you are basically paying seventy dollars and for one of our athletic wear dresses it is only slightly over fifty dollars. So…” She drew out the word, rolling her hand in the air.”

Jerry nodded, getting where she was going. “You are paying twenty dollars less for one outfit. Right?”

“EXACTLY!” Reina said excitedly. “This will give more variety to your wardrobe and you get to wear something more feminine, something to help you feel cute.”

The gears in Jerry’s mind seized up as his eyes went wide, finally realizing she had meant for him to wear the dresses. “I…I… I can’t wear a dress!” His instincts made him want to drop the clothing right away and step away like it was a snake ready to bite him, but the light material felt nice in his hands and he found himself instead just holding them up and looking them over.

It is okay to show your feminine side. You feel more confident being feminine.

Having a feminine body makes you more confident. You love what you’re becoming.

Giving Jerri a perplexed look Reina took in a deep breath Reina stayed silent for a moment instead of just reacting, realizing she hadn’t fully understood just how bad off the girl was. “Okay. You don’t have to do anything you don’t want to, but let me ask you a few questions.” Reina said nodding, one of the first sales training classes the gym taught was to nod or shake your head when asking a question to put the person you are talking to into the mind set of responding accordingly. “You said you like the outfit?”

“Yes, but…” Jerry stopped talking when Reina held up a finger.

“You also think I look good in it?”

Once more Jerry nodded, feeling a light blush come to his cheeks, very much liking how she looked.

Stepping closer Reina reached out and gave a light reassuring squeeze to Jerri’s bicept. “I know how I look, put together, confident, but we aren’t so different. I swear I have more days where I feel less than… less than others, less than myself. It takes effort, sometimes I hate the way I look, my nose is too big, my ears stick out too much, but I still put on my makeup, do my hair and get ready to face the world. By the time I get to work a lot of that stress melts away, this place makes me feel safe and I am able to let those insecurities go. Wearing something like this…” Reina took the purple high neck dress back from her client. “Helps me feel confident. So it may feel like it isn’t something you want to wear, you rather hiding your body away, the waist trainer is going to help and a dress like this is a step in making you feel how special you really are and I know you want to feel confident. Right?”

Jerry felt flabbergasted, there was so much to mentally unpack with what she said. Reina seemed like the type of girl who was always popular, the type of girl that was excited at school as she ran around in her cheer squad uniform on game days, not the type that had confidence issues. “You want me… to wear a dress?” he asked all while the subliminal messages ran through his mind, altering his reactions, some being present in his mind for longer having more effect than the more recent messages.

Stay, you feel safe here. Join SpaFreu.

You trust your personal trainer. They want to help you, be the real you.

It is okay to show your feminine side. You feel more confident being feminine.

Your waist trainer keeps you supported and looking fit. You love how it hugs and defines your shape.

“The only thing I want Geraldine is to help you, so I want you to want to put on the dress. How about we try it on and if you hate it, then we can put it back on the rack.”

"You want me to want to put on the dress? Is this some sort of confidence test?" Jerry asked, his voice wavering slightly.

The question hung there, honest but defensive. As soon as the words left his mouth, Jerry tried to steady his breathing, his mind racing. He thought about how some men were so secure they could joke about stuff like this and shrug it off, actors, performers, rock stars. Confident guys. Men sure enough in who they were that nothing shook them. Then there were the other… fragile, the type that would snap at even a suggestion of something like this.

‘I'm not that kind of guy.’ he thought, his mind drifting off to a few years ago when he let one of his nieces paint his nails when he was watching them so his brother could have a night out without having to pay a babysitter. She had made a mess, and there wasn’t any sort of uniform color used, he was able to laugh it off then. ‘It is just a piece of fabric… Reina is testing me. If she thinks I’m so insecure that I can’t put on a piece of clothing would she even want to go on a date? No… she isn’t so superficial, I trust her and I should, I can do this.’

If anything, the only thing Jerry was sure of was confident in was his intelligence. He wore baggy clothing for a reason… his thoughts drifted off to the mental statement about being confident in his mind, but even there, he knew others in his field who were sharper, more successful. Confidence wasn’t exactly an area in his life he excelled at.

Reina nodded slowly at her, reading her hesitation as vulnerability, not resistance. ‘Poor girl.’ she thought. ‘She just needs some help breaking through this little wall.’

“It’s just a test of confidence, sure,” Reina said gently, her voice warm. “Fake it till you make it, Geraldine. You’ve already been doing that every day you’ve walked into this gym, and look how far you’ve come.”

She gave their arm an encouraging squeeze.

You trust your personal trainer. They want to help you, be the real you.

Jerry swallowed, tightening his grip on the soft fabric of the lavender dress.

‘It’s just a confidence test.’ he repeated to himself. ‘And… and Reina believes I have it in me. She wouldn’t have asked me on a date if she didn’t see something in me. She thinks I’m cute. She’s rooting for me.’

His pulse hammered. Every instinct told him this was crazy. But how could he say no when Reina easily one of the most beautiful, confident girls he'd ever met believed in him?

Stay, you feel safe here. Join SpaFreu. The message rolled gently under the surface of his thoughts, smoothing out his anxiety like a steady hand on his back.

“If I hate it,” Jerry said nervously, “I can still say no, right?”

“Absolutely,” Reina promised with a smile. “No pressure. You have full control.”

That word “control” settled his nerves a little. She wasn’t forcing him. He was choosing, he told himself even if he had no idea how much he was being influenced.

You feel more confident being feminine.

‘And besides,’ Jerry rationalized, ‘It isn’t like everyone is going to see just Reina… the beautiful girl who I have a crush on… well fuck.’

He nodded, almost convincing himself. “Okay. I’ll try it.”

Reina’s face lit up as if Christmas had come early. “Perfect! The fitting room’s right over here.”

Jerry stepped into the fitting room, taking note they didn’t bother separating them by gender. It was all the same anyhow, he had even noticed the gym only had bathrooms, not men’s and woman’s rooms before. The curtain for the changing room itself falling softly behind him. The lighting inside was warm, almost flattering, and the scent of lavender still hung in the air.

He pulled off his pink SpaFreu shirt, folding it carefully and placing it on the nearby bench. The waist trainer hugged his torso snugly beneath the skin, shaping his middle. The tightness was still strange, but oddly reassuring at the same time.

Your waist trainer keeps you supported and looking fit. You love how it hugs and defines your shape.

As he glanced in the mirror, he paused again. The waist trainer really did pull in his stomach to make him look slimmer even giving him a gentle curve to his sides. His stomach looked flatter than it ever had before. He still didn’t feel great about the sports bra, but it was a requirement for the gym he hoped they faced out sooner rather than later, but even without taking off the pants the lack of body hair, not that he had a lot of it changed the way he looked in a subtle way.

Body hair is for men… not someone as feminine as you, Geraldine.

The contradiction flickered again, but instead of outright rejection, his mind spun it into another half-truth ‘I mean…’ he peeled the tight pants down after pulling on his sneakers, now looking at his thin pale hairless legs. ‘Plenty of athletes shave. Swimmers, cyclists, bodybuilders. Being smooth doesn’t mean anything.’

You want to take better care of yourself. Body hair is for men, not someone as feminine as you, Geraldine.

He carefully stepped into the lavender dress. The material slid easily up his legs and over his boxers, then the waist trainer, settling into place as if molded for him. The skirt flared gently around his thighs while the high neckline hugged just under his collarbone.

Jerry adjusted the crisscross straps at the top, feeling them rest over his shoulders. Then he finally looked in the mirror.

His breath hitched again.

“Oh God...”

The waist trainer gave him a more defined figure, pulling his waist inward into a subtle hourglass shape rather than the straight V-line most men carried. The dress hugged that new contour easily, the soft fabric gliding over his frame without resistance. Across his chest, the fabric rested smoothly against the light shaping of the sports bra beneath, nothing dramatic, but enough to round the line of his upper torso ever so slightly. It partially created the impression of real breasts, thought it mostly softened the flatness just enough that the dress didn’t hang like it would on a man. The skirt flared out over his bare, smooth legs, the hem swaying gently with every small movement. Above it all, his high ponytail, still tied back with Reina’s pink scrunchie, bounced playfully as he shifted, adding a light, almost flirty sway to his silhouette. In the boutique’s warm lighting, his reflection seemed softer, his features more delicate. Almost… pretty.

‘It’s… it’s not permanent. It’s just a confidence test, he reminded himself quickly. Just something to prove I can fake confidence... I mean, be confident . A lot of guys couldn’t even do this much. That makes me braver, right? Right?’ his mind rambled on, even as a part of him did feel a little more confident, proving to him the **** of sheer will he could over come his personal issues.

Having a feminine body makes you more confident. You love what you’re becoming. The subliminal message pulsed again in the back of his mind. His nerves warred with an unexpected glimmer of pride.

‘If Reina thinks I can pull it off… maybe I can.’ Jerry told himself, running a hand down his side, eyes looking at the small bumps in the front of the dress. He had noticed them in the pink tee as well, the sports bra wasn’t exactly a pushup bra, pretty much the opposite, but it still had an effect that seemed more prevalent in the tighter dress.

“Everything okay in there, sweetheart?” Reina called gently.

Jerry exhaled. “Yeah… I think so.”

“Come on out, let’s see!”

He drew back the curtain and stepped into the open space, despite his better judgment saying to not let anyone else see him like this, but he couldn’t help smiling slightly and blushing when he saw the reaction he got.

Reina’s eyes lit up instantly, her face glowing with approval, her hands folding together as she beamed at Jerri. ‘She’s coming along beautifully.’

“You see?” Reina whispered, stepping up behind her client, hands lightly resting on Jerri’s shoulders as they faced the mirror together.

Jerry stared at his reflection, pulse thumping loud enough that it felt like someone was pounding those large massive drums just to play out inside his mind. “I… actually… don’t look terrible?” his already naturally soft voice went up an octave as the statement changed into a question.

“You’re beautiful, Geraldine,” Reina whispered, her tone proud and sincere, the light grip she had on the girl changing into a hug on impulse.

Jerry opened his mouth to object, to say something but the words stalled as he felt the embrace from behind, Reina’s breasts pressing into his back as she hugged him. The weight of the moment held him still. His gaze flicked in the mirror from Reina appearing so happy, to his own waist, the ponytail that still swayed above his head and then back to her. “I... guess it’s not as bad as I thought,” he finally admitted, voice barely above a whisper.

Reina smiled warmly, giving his shoulders a gentle squeeze as she stopped the hug. “That’s because you’re seeing the real you,” she whispered into his ear.

“The real me?” he questioned, seeing himself wearing the dress looking more feminine than he ever had before.

“Yep!” Reina declared. “Someone who is confident enough to wear a dress, and a cute one at that. Why don’t grab your clothing, and you can then put on your new sneakers, you can wear the dress out.”

“Wear it out!?”

Pointing in the mirror at Jerri spoke in a commanding voice, wanting to rile the girl up a bit, she looked cute and needed to know it was okay to be so. “Look at yourself, I see someone ready to face the world, to show everyone that you can dress the way you want, that you can wear a dress with the confidence you deserve!”

Jerry carefully stepped into his new sneakers, the ones he was about to pay for, feeling the new lavender-accented shoes hug his feet with a snug but comfortable fit. The dress swayed slightly as he moved, brushing gently against his smooth legs in a way that still made his stomach flutter. His bare exposed legs making him feel more exposed than a day at the beach wearing just his swim trunks.

Reina was already stacking items neatly on the checkout counter as one of the boutique attendants, a young woman wearing the same lavender color SpaFreu apparel only her own was a polo top, quietly stepped forward. She glanced at Jerry in the dress and the second she looked in his direction alarm bells started to sound in his mind. Only, the young woman didn’t reacti negatively or really react at all to see a man wearing a dress. She only offered a polite professional smile, and continued scanning the tags as if nothing about this was unusual. No strange looks. No comments one way or the other.

Reina wished her coworker would have given her client a compliment, but she was knew and only made an hourly wage. For Jerry on the other hand it both comforted him and unsettled him.

‘They’ve seen it before. I mean… this gym used to be women-only, right?’ he tried to rationalize. ‘Probably plenty of people wear stuff like this. I guess… it’s not that weird here.’

The attendant silently continued ringing everything up. Leggings, shirts, both dresses. His original gym clothes sat neatly folded in a SpaFreu shopping bag alongside his still new, but slightly older shoes. The other employee didn’t blink as she carefully packed the white tennis dress and the remaining items, treating each one with the same mundane efficiency as if Jerry buying a wardrobe full of women's athletic wear was simply routine.

Reina beamed. “You’re going to feel so much more confident having variety, Geraldine.”

You feel more confident being feminine.

Jerry nodded nervously, trying to focus on her voice, not the internal tension still twisting under the surface.

Next, Reina gently slid the white corset onto the counter, the non-gym-athletic wear version she’d ordered for home wear. The fabric was thinner, more flexible, but still shaped to cinch his waist firmly. She had mentioned it before, but talked around the idea that it like what Jerri was wearing was considered a corset. She didn’t know why the girl had such an aversion to some things that were more feminine, but was willing to work with her. She still couldn’t believe she got her to wear a dress, just making her beam with pride at herself and her client. “This one’s for you to wear outside of the gym,” she said casually. “Nothing heavy, just gentle support throughout the day. It'll help your posture even more and help train your waist.”

Jerry blinked. “I’m supposed to wear one… all day?”

Reina smiled like she was explaining something completely obvious. “Of course! It’s part of getting you into shape.” She squeezed his arm reassuringly. “You trust me, right?”

You trust your personal trainer. They want to help you, be the real you.

“R-right. Yeah.”

She gave the girl a proud nod, turning back to the attendant. “The Bust-UP meal replacements will be delivered to her apartment later today, so we won’t add those to the bags.”

“Noted,” the attendant replied with a quick tap of the screen.

Jerry swallowed, watching as his growing pile of purchases accumulated neatly into glossy SpaFreu shopping bags as the numbers on his side of the counter kept going up and up.

Reina glanced over all the products, thinking about her commission. “And now… let’s set you up with your SpaFreu credit account. Easy monthly installments, very low interest.” She gestured to the tablet terminal the attendant handed over. “This just makes it simple, I already filled out everything with the information I had in the system for you. Honestly Jerri, you deserve to feel good without stressing about some large lump sum, you deserve to both pamper yourself and the peace of mind of not killing your wallet.”

Jerry’s nerves prickled again. Debt always made him anxious, but Reina’s voice was soft, calming, reassuring and with how she smiled at him, so proud of his progress, how could he refuse? It wasn’t like he couldn’t afford it, his job paid well enough.

‘It’s an investment in myself,’ Jerry thought, thinking purposely more about the meal replacement shakes and how he wouldn’t have to do laundry every day, trying very hard to not think about the dress he was wearing that was just long enough to not show his boxer shorts.

Stay, you feel safe here. Join SpaFreu.

He tapped through the digital contract and authorized the new credit account, watching as the system approved it instantly.

“Perfect,” Reina said brightly. “Everything’s all taken care of.”

The attendant handed him his SpaFreu bags with practiced ease. Jerry accepted them, the weight of the bags surprisingly light compared to the weight in his stomach.

Reina stepped beside him, lightly brushing a stray lock of hair back into place near his high ponytail. “You’re going to turn heads in that spin class, you know.”

Jerry’s cheeks flushed. “I-I’m still doing that… today?”

“Absolutely.” She winked. “And you are more than ready.”