Jay

Mostly rebloging and posting whatever Cash app: $SomeonenamedJay1 https://wishlist.com/ls/Kdlg9A

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@simpingsissygurl how about this for a caption?

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I'll Wear this if you buy me it

Cash tag: $SomeonenamedJay1

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Not sure what caption to put

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Boy to girl cheerleader

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To keep a secret

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You want this

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[sweetsissycaptions]

Sissy Caption: That’s Business

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[thesissyplan]

Mistress Made You a Sissy

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The New Cheerleader pt1

Evan had never been great with paperwork. Forms, deadlines, tiny checkboxes—his brain treated them all like optional suggestions. So when he decided to try something new for the fall extracurricular fair, he grabbed the first clipboard he saw, scribbled his name, and walked away feeling oddly proud of himself.Two days later, he learned he had accidentally signed up for the all‑girls cheerleading team.And by then, it was too late to back out.Evan had been quietly exploring his gender identity for a while—trying on small pieces of femininity in private, wondering what it would feel like to be seen the way he felt inside. But he hadn’t planned on this being his big debut.When he showed up to the first practice, Coach Ramirez looked at the roster, then at him, then back at the roster.“You’re Evan?” she asked.He swallowed. “Uh… yes?”She shrugged. “Alright. Grab a bow from the box. Let’s see what you can do.”The girls whispered, but not unkindly—more curious than anything. Evan tied the pink bow into his hair with trembling hands. It felt… right. Too right.

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The New Cheerleader pt2

Finding His Place

Cheer was harder than he expected. The jumps, the chants, the timing—everything demanded precision. But the team worked with him, teaching him counts, helping him stretch, laughing with him when he fell out of a stunt.And slowly, something shifted.He started wearing softer clothes to practice. Then leggings. Then a sports bra under his shirt.Not because he needed it, but because it made him feel like he belonged. Practices became the best part of her day. She learned to do her makeup with the other girls before games. She borrowed uniforms until the coach ordered one in her size. She even started using the girls’ locker room. Cheerleading didn't just give her a place but a chance to see herself.The day Coach Ramirez handed out uniforms, Eva felt her stomach drop straight through the gym floor.“Sizes are on the tags,” the coach said, tossing folded bundles of red and white fabric to each girl. “Try them on before Friday so we can make adjustments.”When the bundle landed in Eva’s hands, she froze. The fabric was soft, lighter than she expected, and the pleated skirt peeked out from the folds like it was daring her to touch it.Maya nudged her. “You okay?”“Yeah,” Eva lied, clutching the uniform like it might evaporate if she loosened her grip. “Just… nervous.”“First uniform jitters,” Maya said with a grin. “Happens to everyone.”But Eva knew her nerves weren’t the normal kind.She waited until she got home, locking her bedroom door even though no one else was around. She laid the uniform out on her bed like it was something sacred.The top was sleeveless, with the school’s name stitched across the chest in bold letters. The skirt was pleated, swishy, and impossibly cute. She ran her fingers over the fabric, heart pounding.“This is really happening,” she whispered.She slipped the top over her head first. It hugged her torso in a way that made her feel… aligned. Like her reflection was finally catching up to who she was inside.Then came the skirt.She stepped into it slowly, pulling it up over her hips. When the waistband settled into place, she felt a warmth bloom in her chest — a mix of joy, relief, and something she’d never had words for until now.She turned to the mirror.And for the first time, she didn’t see a boy trying to look like a girl.She saw herself.Eva.

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The New Cheerleader pt3

The First Reveal

The cheer squad always warmed up on the track before school on game days. It was tradition: a quick run, a few stretches, and a chance to show off the uniforms.Eva stepped out of the locker room with the rest of the girls, her skirt swishing lightly with each step. She kept her eyes down, heart pounding so hard she could feel it in her fingertips.The first group of students to notice were the cross‑country kids. One of them blinked, tilted his head, and said:“Wait… is that Evan?”Maya stepped forward before Eva could shrink into the turf. “That’s Eva,” she said, voice firm but friendly. “She’s with us.”The boy nodded slowly. “Oh. Cool. The uniform suits you.”Eva nearly tripped over her own feet.By second period, the news had spread.Some reactions were exactly what she feared: confused looks, double‑takes, a few whispered conversations that stopped the moment she walked by. But none of it felt cruel — more like people trying to recalibrate their mental picture of her.A group of girls from the art club stopped her near the vending machines.“You look adorable,” one said.“And your bow matches your eyes,” another added.Eva flushed. “Thanks… I wasn’t sure how people would react.”The first girl shrugged. “Honestly? We’re just impressed you can do toe‑touches. I can barely touch my toes.”They all laughed, and the tension in Eva’s shoulders eased.

After school, as Eva was packing up her bag, a freshman girl approached her shyly.“Um… Eva?”Eva turned. “Yeah?”“I just wanted to say… seeing you today made me feel braver. I’ve been scared to join drama club because people might think I’m weird. But you looked so happy out there. So… thanks.”Eva’s throat tightened. “You should join. Drama club would be lucky to have you.”The girl beamed and hurried off.Eva stood there for a long moment, letting the weight of it sink in.She hadn’t just been seen.She’d been recognized.---By the End of the Week…People weren’t whispering anymore.They were waving.Smiling.Asking about the next game.Eva wasn’t the boy who joined the cheer team anymore.She was Eva, the girl who nailed her jumps, wore her uniform with pride, and walked through the halls like she finally belonged in her own skin.And the school surprisingly adjusted around her.

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The New Cheerleader pt4

It started during third‑period chemistry.Eva was half‑listening to the lecture, half‑doodling little stars in the margins of her notebook, when the classroom door swung open and Jordan Hale walked in late.Jordan wasn’t just popular — he was the guy. Quarterback, honor‑roll student, annoyingly good hair, the kind of smile that made people forget what they were saying mid‑sentence. Eva had never paid him much attention before; back when she was still presenting as a boy, he’d just been another face in the hallway.But now?Now her stomach did a weird flip when he brushed past her desk.He muttered, “Sorry,” as he squeezed by, and Eva felt her cheeks warm. She stared at her notebook, suddenly very interested in the doodle she was pretending to finish.

The Moment Everything Shifted After school, the cheer squad was practicing on the field while the football team ran drills. Eva was working on her jumps when she heard someone call out:“Hey! Nice form!”She turned — and there was Jordan, helmet tucked under his arm, grinning at her like they were old friends.Her brain short‑circuited.“Oh— uh— thanks,” she managed, hoping she didn’t sound like she was choking on air.“You’re new, right?” he asked.“Kind of,” she said. “I’m… Eva.”“Eva,” he repeated, like he was testing the sound of it. “Cool name.”Her heart did a somersault.Maya caught her staring after Jordan as he jogged back to his teammates.“Oh my god,” Maya whispered, sliding up beside her. “You like him.”Eva nearly dropped her pom‑pom. “What? No. I mean— he’s just— he’s nice.”“He’s Jordan Hale,” Maya said. “He’s not just nice. He’s, like, genetically engineered to be distracting.”Eva groaned. “Please don’t make this a thing.”Maya smirked. “Too late. It’s already a thing.

The next day, Eva was struggling with her locker combination — her hands were shaking from nerves she refused to admit were crush‑related — when someone stepped up beside her.“Need help?”Jordan.Of course.She laughed awkwardly. “It’s fine. My locker just hates me.”He leaned against the locker next to hers. “You looked good at practice yesterday.”Eva froze. “I— what?”“Your jumps,” he clarified. “You’ve got height. Most people don’t get that right away.”“Oh,” she said, trying not to melt. “Thanks.”He smiled, easy and warm. “See you at the game tonight?”“Yeah,” she said, heart hammering. “I’ll be there.”As he walked away, Eva pressed her forehead against her locker door, whispering to herself:“Okay. Don’t freak out. Don’t freak out. Don’t—”She freaked out.Quietly. Internally. But absolutely.Eva didn’t know if it was just a crush or something deeper. She didn’t know if Jordan liked her back or was just being friendly. She didn’t even know if she was ready for anything romantic.But she did know this:For the first time in her life, she felt like she was allowed to have a crush. A real one. A girl’s crush. Her crush.And that alone felt huge.

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Sisters boyfriend