The Perfect Fit

“Gemma!” he exclaimed, turning to his sister who stood behind him. “I’m you and you’re me! Something must’ve gone wrong when we traveled to the past to relive that family vacation.”

Gemma, now in Ryan’s body, looked just as stunned. She reached up to touch her own face, her fingers tracing her features as if she couldn't believe what she was seeing.

“I’m wearing your favorite dress… When you were 15…” he said, his voice trembling with disbelief.

“Ryan, this is insane! How are we supposed to fix this?”

“The Time Machine was set to two weeks. Now we’re stuck in each other's bodies…”

“Which means we have to act like each other,” Ryan's heart raced as he glanced down at the colorful sundress that swirled around his—no, Gemma's—legs.

“We have to get through these two weeks without anyone noticing,” he replied, his voice sounding higher and softer than usual.

Gemma bit her lip, her eyes darting around the room, “Right. Just a normal vacation with Mom and Dad, right? Easy peasy.”

Ryan felt a flush of embarrassment as he looked down at Gemma’s cleavage, the neckline of her dress dipping lower than he was used to. He quickly crossed his arms over his chest, trying to hide the unfamiliar curves.

“Ugh, I can’t believe I have to spend two weeks in this body,” he muttered, feigning disappointment.

But, secretly, Ryan couldn’t wait to get some time alone to …intimately explore Gemma’s 15-year-old self…

The truth was, while Ryan was a straight man, throughout his teenage years, he would sneak into his mother’s and sister’s rooms while they weren’t home to crossdress.

He remembered seeing Gemma grow up, how she had blossomed during puberty. Now, being thrust into her body at the peak of his crossdressing years, it was like a dream come true. He could actually be Gemma, and time paradoxes meant he could do whatever he wanted without consequence.

As the realization settled in, a thrill rushed through Ryan’s veins. He was no longer just playing dress-up; he was living out a fantasy he had kept hidden for years.

He could finally wear the clothes that had once felt so forbidden, and now, they were his. Or were they hers? He shook his head, trying to clear the confusion swirling in his thoughts.

“Ryan, are you even listening?” Gemma snapped.

“Sorry, I got a bit lost in thought,” Ryan replied, forcing a smile, “What were you saying?”

Gemma rolled her eyes, “Never mind. We should probably head back to the hotel. I don’t really want to be dealing with this in a public park.”

Ryan nodded, trying to suppress his excitement. Each step felt surreal as he swayed slightly in the sundress, the fabric brushing against his skin in a way he’d only fantasized about during those secret moments alone.

The thought of the hotel made Ryan giddy. He thought about getting undressed, taking a shower, and trying on clothes from his sister’s suitcase.

When they reached the bustling lobby filled with families and vacationers, Ryan took a deep breath, trying to channel his sister’s confident demeanor. Spotting their parents chatting in the lounge area, Gemma quickly nudged him.

“Smile! Just act like you’re having fun.”

Ryan plastered a wide, cheerful grin across his face, mimicking the way he had seen Gemma smile in the past. It felt strange but exhilarating, each facial muscle stretching in ways that felt entirely new. He glanced at Gemma, who was doing her best to keep a poker face despite her obvious stress as they approached their parents.

“Hey you two!” their mother called out, waving them over, “How was your walk?”

“It was great!” Ryan chirped, forcing his voice into higher registers and attempting to infuse it with the enthusiasm he remembered Gemma usually displayed, “We saw the lake, and the ducks were so cute!”

“Ducks?” their dad chuckled, raising an eyebrow, “Only you would notice the ducks! What do you think about heading out for dinner soon?”

“Sure!” Gemma replied with a hint of nervousness that mirrored Ryan's own, “I’m starving!”

“Alright then,” their mother said, glancing at Ryan and then back at Gemma, “You should probably go up and get ready.”

Ryan's heart raced at the thought of what awaited him.

“Right! I’ll just… go freshen up!” The words tumbled out of his mouth before he could fully process them, but the prospect of being alone in the hotel bathroom sent his heart racing.

As they made their way up in the elevator, he stole glances at Gemma, who stood quietly beside him, her eyes wide with disbelief. The sound of the elevator ding echoed like a drumbeat of their shared secret, and Ryan felt a surge of excitement—this was not just a chance to walk in his sister's shoes; it was an opportunity to truly become her.

“We’re kids again, Gemma. Only now…” He glanced at her, a mischievous grin spreading across his face, “Now I get to be you.”

As soon as Ryan and Gemma stepped out of the elevator, Ryan could feel the adrenaline coursing through his body. They walked down the hallway towards their hotel room, anticipation building with each step.

Gemma dug for her key in her purse and unlocked it with a satisfying click.

He walked into the bathroom and closed the door behind him. The space felt new and exciting, yet also familiar at the same time. He couldn’t believe that he was actually going to use his sister’s toiletries and wear her clothes. He stared at his reflection, the soft curves, the bright eyes—this was not just a disguise; it was Gemma’s essence encapsulated in flesh and bone.

Only, this wasn’t Gemma from 2025. This was 15-year-old Gemma from 2014. Ryan leaned closer to the mirror, studying every detail of Gemma's face. The freckles dusting her cheeks, the hint of gloss on her lips, and the delicate arch of her eyebrows—it was like looking into a time capsule. He remembered this version of Gemma from this trip.

With trembling fingers, he started undressing her slowly. He noticed every detail—the curves of his body hidden under layers of clothing, the way his hair flowed past his shoulders instead of being cropped short like it usually was.

Her young body was unmistakably feminine. She donned a padded push-up bra, and Ryan paused, gazing at it for a moment. Being in such an intimate setting while wearing something that accentuated the shape of his—Gemma's—body felt unusual. He was filled with a blend of excitement and hesitation.

"I have TITS!" he mouthed to himself, heart pounding with the peculiar thrill of the experience.

He jumped to make them jiggle, quickly brushed his fingers across his new curves again, half afraid he might wake up from this dream.

He reached for them with enthusiasm, "Holy shit, I’m a girl. I’m Gemma…”

“I’m the real Gemma…” Ryan continued, delving further into the fantasy, “My ‘brother’ wishes he could be me. He would never understand what it’s like to be me, to wear my clothes, to have this body...”

Ryan's hand ventured into her panties. He couldn't believe this was happening; he was actually getting to experience what it felt like to be his sister. His mind swirled with forbidden thoughts and desires he had never dared to act upon before.

He hesitated for a moment, his better judgment battling with the thrill of the situation. But he quickly reminded himself that this was an opportunity that might never come again. With a deep breath, he slid his fingers further inside her panties, moaning softly as he discovered the wetness that awaited him.

"I'm Gemma," he whispered to himself, "A hot 15-year-old girl who's always wanted to experiment with her body. I’m just exploring what it means to be me.”

A rush of excitement coursed through Ryan as he realized that no one would ever know about this secret, hidden away in the privacy of the hotel bathroom. He could explore his desires to his heart's content, all while pretending to be Gemma. The taboo nature of the situation only heightened the thrill.

Ryan continued to touch himself, picturing himself as his sister, Gemma. The wetness between his legs only grew more insistent as he thought about all the times he'd secretly longed to be her... He unhooked her bra, freeing her newfound breasts, and marveled at the weight of them in his hands. He cupped them gently, then not-so-gently, squeezing and caressing them like he'd always wanted to.

Ryan couldn't believe the sounds coming from his mouth—his sister's mouth, now that he thought about it. He'd fantasized about this for years, but never in his wildest dreams had he imagined it would actually happen. He undressed completely, admiring every inch of his sister’s naked body.

Just as he was losing himself in the fantasy, the sound of a knock at the bathroom door jolted him back to reality.

“Ryan! Are you almost done?” Gemma’s voice called from the other side, laced with impatience. “Mom and Dad are waiting!”

Panic flooded through him. He quickly withdrew his hand and turned on the faucet, splashing water onto his face to wash away the embers of that fleeting moment. He frantically wiped his damp hands on a towel and took a deep breath, struggling to regain composure.

“Yeah! Just… give me a second!” he shouted, trying to sound as nonchalant as possible while his mind recoiled from what had just happened.

With a deep breath, he began rummaging through Gemma’s suitcase, pulling out different outfits. He paused on a pastel blouse adorned with tiny flowers that reminded him of their vacation snapshots. He realized he’d worn it before. He remembered sneaking into Gemma’s room once as a teenager and trying it on. Only then, it had been taboo.

Now it fit perfectly.