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Chapter 23 by Nicegent42

What's next?

Little stretch largely turned on

Reina gathered the last of the glossy SpaFreu shopping bags, two filled with new athletic outfits and the third holding Jerri’s original clothing, and stacked them neatly on her rolling cart beside the boutique counter. She turned back to the petite blonde girl in the lavender dress with a bright, effortless smile.

"Why don’t I keep all this at my desk for now?" she suggested, brushing a strand of hair from her cheek. "No reason for you to carry these around the gym."

Jerry looked at the bags, then at Reina.

Part of him felt an immediate spike of anxiety. Those bags held the clothes he had come in wearing. If he kept them with him, he could change back at any time. He could end this challenge early. He could retreat if things got too embarrassing.

But if he let Reina take them, he would be fully committed to staying in the dress until she brought them back. No escape. No quick switch back to pants and a shirt.

That thought made his stomach tighten. At the same time, carrying a stack of bags around the gym would look ridiculous. More importantly, Reina was trying to be helpful. She was smiling, being kind, going out of her way to make his experience easier. Saying no would seem rude, or ungrateful, or insecure. He did not want her thinking he was backing out already.

And he had already proven he could put on the dress.

If he immediately changed back out of it, he would just look cowardly.

He swallowed and nodded. "Yeah," he said softly. "That would help."

Reina’s smile deepened with warm approval. "Perfect. I will keep everything safe for you."

Her voice carried that gentle, confident tone that made him feel supported, as if she was guiding him step by step. It was comforting in a way he had never expected.

Stay, you feel safe here. The faint subliminal hum blended into the boutique’s background music. Jerry hardly noticed it, but his shoulders relaxed a little.

Reina tucked the bags securely onto her cart. Watching her roll them away made Jerry’s chest flutter again, a mix of nervousness and determination. Without those bags in his hands, he no longer had the option to change back. He was really doing this. He was walking into a gym in a dress. And he was doing it in front of Reina.

He straightened slightly. He had committed. Now he needed to look confident about it, even if he didn't feel it, but at the same time wearing the athletic wear dress made him think that it proved he was more confident so he must be.

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

Reina gestured toward the boutique door with an encouraging expression. "Ready?"

Jerry adjusted the light skirt of the lavender athletic dress and felt the activewear corset hug his midsection, guiding his posture upright. This was not humiliation. This was a challenge. A test of confidence. A chance to show Reina he was not afraid to push himself.

He nodded. "Yeah. I am ready."

He followed her toward the sliding door. Each step sent the skirt brushing lightly against his smooth legs, an unfamiliar sensation that still felt strangely… purposeful. Like this was what stepping outside his comfort zone was supposed to feel like.

None of the women in SpaFreu reacted to seeing him at all. They had smiled, moved on to their work outs, or simply continued what they were doing. No staring. No whispering.

‘Maybe the women here were simply accepting and open minded. Maybe they respect someone who challenges themselves. Maybe they even feel safer around a guy who was not afraid to show a softer side.’ the thoughts went on and on in Jerry’s mind when no one acted like it was odd at all to see a man in a dress and it really did feel reassuring.

Stay, you feel safe here

The soft whisper of the subliminal blended with the rush of cool air as the boutique door opened. Jerry breathed steadily, lifted his chin a little, and stepped deeper into the main room of the gym.

Reina pushed the rolling cart out of the boutique and guided it to the front reception desk. She gave the attendant a cheerful nod, then lifted the bags one by one and placed them behind the counter.

"Keep these here for Jerri, please," she said warmly. "I will pick them up after her sessions."

The attendant smiled and tucked the bags safely away. Jerry watched them disappear behind the desk, and his stomach tightened again. Seeing the bags physically stored out of reach made everything feel more real. His comfortable clothes were not just out of his hands now. They were handled by staff and locked away. His option to change back had slipped even further out of reach.

The entire time Jerry watched the bags like a hawk, less so for the new purchases, him not wanting to let go of the clothing he came in wearing.

Reina clapped her hands lightly and gave Jerri an encouraging grin.

"Alright. Now that you are not weighed down by anything, let us get warmed up."

Jerry nodded, though his heart was beating too fast. He had wanted to keep his clothes close in case he lost his nerve. But Reina was being helpful, and she was proud of him. He did not want to look ungrateful or scared now.

Reina gestured toward his earbuds.

"Go ahead and put those in, Jerri. Music helps you focus."

Jerry reached into the small pocket on the side of the lavender dress, his fingers brushing the smooth fabric. The earbuds felt reassuring, almost like stepping back into something familiar. Yesterday, they helped calm him. Today, he needed them even more.

He placed them in his ears. The soft chime of connection played, followed by the gentle rhythm of the SpaFreu playlist.

Underneath the beat, a faint whisper eased into his mind.

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

He did not process the words consciously as words. Instead, he felt a small shift inside his chest, like a knot loosening. His earlier anxiety softened into something steadier.

He followed Reina into the open gym space. The lighting was bright, and the room was filled with steady motion. Women jogged on treadmills, stretched on mats, lifted weights, and chatted quietly with one another.

The dress moved softly against his legs with every step, and the activewear corset held his waist snug, reminding him to stand upright. The skirt swished lightly, and his boxers shifted uncomfortably underneath. The sensation made him want to tug at them, but he resisted. Confident people did not fuss with their clothes. He needed to look composed if he wanted Reina to see he was serious about this challenge.

Reina walked ahead of him with an easy stride, entirely unbothered by his outfit.

And everyone else in the gym seemed equally unconcerned.

A woman at a nearby machine smiled politely as they passed. Another nodded to Reina and continued her stretch. A pair of women near the water fountain glanced up for only a moment before returning to their conversation. Every person coming into his eye line brought with it another chance to call him out for being a perverted crossdresser and yet no one even so much as gave him an odd look.

Jerry felt a warm sense of relief spread through his chest. "They probably think it is cool that someone is not afraid to show a softer side and still be confident about it." He told himself.

“What was that?

Stay, you feel safe here. The subliminal message didnt come through Jerry’s ear buds but from the background music pumped through the gym for all to subconsciously hear and absorb.

“Just saying how nice this gym is.”

Reina guided him toward a quiet stretching area beside a rack of mats.

"We will warm up here," she said brightly. "A little stretching before spin class makes a huge difference."

Jerry nodded, the nervous energy inside him mixing with pride. The music steadied him, and the dress, strangely enough, felt less like a costume and more like a statement he was making about courage. He stepped onto the mat she offered. The skirt brushed his thighs again, the corset nudged him into proper posture, and he tried to focus on the reason he was here.

‘This is just another challenge, a test. A chance to show Reina I can push myself.’ He inhaled slowly, settling into the moment.

Reina pulled two mats from the rack and placed them side by side. She gestured for Jerri to sit on one while she settled onto the other.

"Let us start simple," she said with her usual bright tone. "Legs out in front of you."

Jerry lowered himself onto the mat. The activewear corset instantly made bending forward feel tight, and the lavender dress tugged upward slightly across his thighs. The skirt brushed softly against his smooth skin, reminding him again of how exposed he felt.

Reina scooted closer.

"Good. Now reach forward. Just a gentle stretch."

Jerry leaned, but the corset stopped him far sooner than he expected. The tension across his waist held him rigid. Looking at the beautiful girl at his side, embarrassment hit him. ‘Reina probably thinks I’m horribly inflexible.’

Seeing her client struggle she leaned in to help. "Here. Let me guide you."

Before he could react, the attractive woman placed her hands lightly on his sides, just above the corset line. She applied the smallest pressure, encouraging his body to hinge forward slightly more.

Jerry felt her chest- her perfect breasts that he put more than a little effort to not stare at brush against his upper arm as she leaned closer to check his form. His entire body froze, his breath catching

A warm jolt shot through him, so sudden he forgot to breathe for a moment. She was right there, close enough for him to smell her perfume, soft and clean and something floral. Her hair brushed his cheek as she looked down at the angle of his stretch.

No girl had ever touched him like that.

He had never been this close to anyone who made his heart race. Heat rushed into his face as he blushed. His stomach fluttered wildly. ‘Is she flirting? Is this what flirting feels like? Or is this just how trainers are? She must trust me to be this close.’

Reina noticed the way Jerri stiffened and held her breath. She smiled gently.

"Relax, Jerri. You are doing great."

Jerry’s heart thumped even harder. She sounded so caring, so encouraging, so close.

The subliminals in his earbuds softened the edges of his panic.

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

He interpreted the feeling coming over him trying to justify the subconscious thought

‘I need to act confident so she does not think I am weird and just do as she says.’

He pushed a little farther into the stretch, the movement making the skirt slide up just a bit more, making him feel exposed. and then he felt it. His boxers bunched sharply between his legs.

He winced and shifted, trying to discreetly adjust without making it obvious. The corset limited his twisting, and the dress only made everything feel more awkward. He tugged lightly at the hem, trying to hide the movement.

Reina noticed instantly.

Her eyes softened with concern. "Something feels off? This isnt hurting you, is it?"

Jerry swallowed. His face felt hot again for a completely different reason.

"They are just kind of… riding up," he admitted quietly.

In his mind this was humiliating, the kind of mistake someone with no athletic experience would make. He imagined she thought he was clueless. Reina, however, saw something entirely different.

She saw a shy girl stuck wearing loose, unfitted underwear under a dress, probably too embarrassed to ask for help or too inexperienced to know better. Maybe her boyfriend left those boxers at her place. Maybe she had nothing else clean. Maybe she simply had no idea what would be more comfortable.

"That looks uncomfortable," Reina said kindly. "Loose underwear can do that during stretching."

Jerry nearly died on the spot.

Reina moved a little closer, lowering her voice in a confidential tone, the way women sometimes shared personal advice."Jerri, have you ever worn something more fitted for this kind of activity? Maybe a thong or seamless athletic underwear?"

Jerry felt every muscle in his body lock up.

‘A thong!?’ For a moment he forgot how to think the question feeling so absurd. He felt hot all over, the blush spreading from his cheeks to his ears. He had never worn anything like that. He had barely even touched a thong once, and that had been while folding laundry at his brother’s house as a favor. The idea of wearing one made his brain short circuit.

"No… I have not," he said, barely above a whisper.

Reina nodded gently as if that made perfect sense. "The right pair can make you feel sexy and confident, Jerri," she said. "I promise."

Jerry’s breath hitched again, but for a different reason this time.

‘Sexy. Confident, Does she think I can be sexy?’ He wanted to feel confident. He wanted her to see him as confident. He wanted her approval more than anything.

Reina tilted her head slightly.

"Do you want to feel sexy and confident?"

Jerry hesitated for only a moment before nodding. "Yeah. I do."

Her face brightened with pride.

"Good. That is what we want. Maybe later this week we can find something that fits you properly. Only if you want to."

Jerry stared at her, dazed.

She was offering to go shopping with him. Out of the gym. Together.

It felt like the closest thing to a date he had ever been offered..

"That… sounds good," he said softly.

Reina smiled again, pleased.

"Wonderful. Now let us do the next stretch."

Jerry nodded, barely hearing anything over the pounding of his heart.

Reina knelt in front of Jerri for one last seated stretch. She placed her hands gently at Jerri’s sides to guide her posture, studying her form from below to make sure the movement was correct.

Jerry’s mind reacted instantly.

The sight of a beautiful woman kneeling in front of him, close enough that her breath could have so easily warmed his stomach and her eyes looking upward, triggered a flash of something he immediately regretted. A memory of porn video. A position he had seen too many times. Something that had nothing to do with this innocent moment.

A sharp jolt of embarrassment and arousal hit him. He hated himself for even thinking about it.

‘Come on… Reina was only helping me stretch.’

He swallowed tightly and looked away, face burning, hoping she did not notice and that he wasn't about to get an obvious hard on.

Reina rose smoothly to her feet, dusting off her palms. "Now we move on to squats," she said cheerfully.

Jerry stood slowly, trying to shake off the confusing tension in his chest. The corset guided his posture upright, and the skirt brushed his smooth legs in a way that kept him very aware of himself.

Reina stepped beside her client, now standing at their level. "Feet apart, about shoulder width."

Jerry spread his feet and tried to focus on the instructions.

"Good. Now lower into a gentle squat. I will help you with your form."

He began to bend his knees. The lavender skirt tugged upward across his thighs, his boxers digging uncomfortably between his legs. His balance wobbled.

Reina moved closer, placing one hand lightly on their lower back as she started to see them wobble. "There. Keep your spine straight. Let me support you." Shifting her other hand to Jerri’s hip to guide the angle. As she leaned in to check their posture, her shoulder brushed, and her chest grazed Jerri’s upper arm again, not thinking anything about the touch.

That tiny touch set him off. A sudden, involuntary pulse of arousal surged through him.

His entire body tensed, His breath caught. His heart pounded so hard he could feel it in his throat. Without meaning to, his hips made a small forward thrust.

It was instinctive and crazy Embarrassing and he hoped she hadn't noticed

"Please tell me she did not see that. Please."

Reina did notice the movement, but misunderstood it completely.

"Good, you are beginning to find your balance point," she said kindly. She adjusted their waist with both hands, believing Jerri was simply learning how to center her weight. "Let us try another one. You are doing very well."

Jerry’s knees nearly buckled with relief, believing she had no idea.

‘Thank God she had no idea.’

The subliminal hum pulsed in his earbuds.

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

He latched onto the reassurance.

"Just follow her lead," he told himself. "Stay calm. She is helping me."

They repeated the squat. Every time she guided the movement, their hips or steadied their back.

Another warm flicker of arousal stirred in him. It was faint but impossible to ignore. He prayed that no physical sign of it became obvious.

Finally, Reina stood upright with a pleased smile.

"Very good, Geraldine. You warmed up beautifully. I think you are ready for spin class."

Jerry nodded quickly, still trying to settle the trembling inside him.

"Okay," he managed.

Reina motioned for him to follow. For a brief moment, as he walked behind her with the music in his ears, he almost forgot he was wearing a dress at all.

Then a rush of cold air from the gym’s ventilation swept across his bare legs.

The chill hit his freshly shaven skin, making goosebumps spring up instantly. The skirt lifted slightly with the airflow. He stopped mid step, startled by the cool brush across his exposed thighs.

‘Right. The dress…. My dress I guess… Hell, everyone can see my legs.’

But no woman in the gym stared. No one reacted at all.

A few smiled politely as they passed.

Reina turned back.

"You alright?"

Jerry nodded quickly.

"Yeah. Just felt the air conditioning."

"You will get used to it," she said brightly, unaware of how flustered he was.

He followed her again, the skirt swaying lightly with each step. Embarrassment mixed with a strange sense of pride. He had made it through stretching. He had made it through her touching him. He had made it through his own humiliating reactions without her noticing.

‘She likes me… I think she wants to go shopping with me, Reina isn't being paid for that so it has to be real.’He repeated the words silently until they reached the spin room door.

Reina touched Jerri’s arm gently, giving the blonde girl a bright smile. "Ready for your first spin class, Jerri?"

Jerry straightened as much as the corset allowed and nodded.

"Yeah. I am ready."

What's next?

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