Tomboy in Trouble

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“There’s no way I can borrow that!” Blake recoiled from her friend’s offering.

Amira playfully waved swim trunks in front of her friend. Blake was visiting her over the summer. Normally everything would move smoothly but at the airport her luggage containing most of her clothes went missing. All she was wearing came from Amira’s closet, but most hung from her slender frame in formless blobs. This was likely the only swimsuit in the house that would fit.

“You can always wear a shirt with it. No one cares, and even if they did no one would notice.”

Blake crossed her arms over her chest. She was never the most feminine girl, and easily would describe herself as a tomboy. Her body, although slender, remained as flat as a board. Even though she was in college, she never developed any curves. 

“I can’t go out like that, no way in hell!”

“Ali will be there, gotta take all the time you have until you’re shipped back to school.”

Blake’s eyes widened. Ali was Amira’s friend that she only saw from afar. Ever since then Amira was always trying to find a way to introduce Blake to him. But everytime she got close, she was too embarrassed to even get near him, let alone speak.


Blake slipped off her sundress. Beneath she wore a matching pair of white bra and panties. Amira playfully pulled at her bra strap. 

“What’s the point of even wearing this? It’s not like you have anything to support.”
Blake covered her nonexistent breasts with her hands. They barely created any contrast against her toned body. She was proud of her athletic achievements, they even got her a full ride to school, but would immediately give them up for a body like her friend’s. Blake eyed her friends double D’s with envy. If she even could fill up to a B cup, she wouldn’t be mistaken for a boy as often as she did. 

“Look when God created me and you, he dumped all of the boob stats into you and ran out when he came to me.” She said as she unhooked her bra and let it fall onto the floor. 

“At least you don’t have back pain.” Amira retorted as Blake slipped on the swim trunks. “See you look fine.”

Blake twirled in front of the mirror. The baggy trunks made her seem more adrogenous and boxier than usual. It wouldn’t be her first pick but it would have to do. 

“Now about your hair…” Amira snatched Blake’s bob and cut off a hunk from the back.

“Hey! We never said anything about a haircut.” 

Blake turned around to examine the damage. Her once perfect shoulder length bob had a huge dent in the back. There was no way of saving it.

“You look much better in shorter hair, besides its summer. Live a little before school starts again. You can give me a haircut too if you feel like.” Amira said as she carelessly dropped a four inch lock onto the floor. 

Blake slumped over. Where Amira cut it left only a short patch of bristles. Even if she hid her hair in a ponytail, it would take months for it to get even again. She didn’t have a choice. The damage was already done. 

“Alright, but I get to decide what to give you.”


Blake sat down in front of Amira. She made no hesitation as her friend’s tresses rained down around her. Blake’s eyes widened as she realized that Amira placed the scissors above her ears. She watched as her healthy hair fell to the ground like trash. 

“How short are you cutting it?”

“Enough so you can actually pass as a guy.” Amira retorted as another three inch hair slithered to the ground. She worked quickly, sensing distress in her friend. If she got angrier, the plan would fall to pieces. 

Amira quickly turned on the clippers. They roared as they mowed through what was left of Blake’s hair. Blake flinched a little, feeling the foreign feeling of clippers tickle her head. The short hairs trickled on Blake’s naked body. Slowly a shaggy modern pixie cut formed. The longest pieces just fell to Blake’s eyes. It was layered and textured to create more volume. 

Blake ran her fingers through her new haircut. She could barely tuck the top layers behind her ears. But everything on the back and sides was a uniform black lawn. Amira shaved it close enough that Blake’s pale scalp shone through. 

She looked more boyish than ever. It was quite short, but still fashionable. Amira was right, now she could easily pass as a guy with her swimsuit. With luck she could grow it out to her chin by the end of summer. She would have to wear more makeup and earrings to bring out her little femininity until then.

“Alright my turn.”

Amira eased out of her dress. She wore nothing underneath. Her giant breasts bounced when she pulled off her clothes, as if taunting Blake. Amira had almost perfect brown ringlets that ended at the bottom of her chest. She could cosplay as a mermaid if she wanted to. Blake was always envious of Amira’s perfect hair. Hers never cooperated and refused to grow past her shoulders. 

“Why are you-”

“I don’t want hair to get stuck on my clothes.” Amira handed the scissors to Blake. “I trust you, don’t you trust me?.”

Amira turned and sat across from Blake, her brown eyes widened with anticipation. Blake was still a little annoyed at Amira’s spontaneous makeover. This deserved retaliation. 

Blake moved the scissors to the left side of her head and slowly cut. Sheets of brown ringlets rained down. What was left only hung down above her shoulders, exposing her breasts. 

“Not holding back are we?” 

“Live a little, right?”

Amira laughed as Blake worked her way around her head. Blake wasn’t as well of a hairstylist as Amira. The rough bob was still uneven. It made her seem older, more attractive.

“Damn, never knew I could pull off a soccer mom cut like this. Do I look like a MILF now?”

Amira twirled her head, her short hairs bouncing in the sunlight. The longest hairs just reached the tips of her chin. The dramatic bob drew attention away from her hair and back onto her face and body. Blake shaved her nape to keep the bob as sharp as possible. She looked much more mature.  

Blake glanced back into the mirror in front of them. This could work, now it was time to see if it could actually work.


A lifeguard’s shrill whistle blew. 

The two girls both turned around. It was Ali smiling at the two of them. 

“Hey Mira! Whoa you look great with short hair.”

Amira mockingly twirled her short hair with her fingers. “If you like it so much, why don’t you tell my new hair stylist? This is Blake. Blake meet Ali.” 

Blake awkwardly waved. She crossed her arms over her t-shirt. The people who let them in didn’t say anything about her looks, neither did anyone around them. Was this working? 

“Hey uhh…Blake, I hate to be a wet blanket but we have a policy of not letting people wear shirts in the pool.”

“But I can’t-”

“Sorry bro, rules are rules.” 

Bro? Blake’s face flushed red again. He definitely thought Blake was a guy, but there was no getting out of this. 

Amira’s jaw dropped as Blake shifted out of the shirt, slowly revealing her flat chest. Her nipples pinched out slightly as they slowly became erect in the cool shade. Blake blushed and turned her head. Out of all the things to happen that day, the surprise haircut and meeting Ali, becoming an exhibitionist wasn’t one of the things she couldn’t have predicted. 

“Anyways,” Amira said, “We wanna hit the slides before they close so we gotta bounce, see ya Ali.”

Amira and Blake turned to walk away before -.

“Wait.” Blake turned around, face still flushed. “What’s your routine? I’ve never seen anyone with pecs like yours.”

Ali reached out and rubbed his thumb on Blake’s breast. Soft fat gave way to his calloused fingers. Blake squeezed her eyes shut. Surely he would figure it out by now. 

“Nice. I’ll see y’all after the shift.” He slapped her ass as she practically ran away. 

Once they rounded the corner, Blake crouched immediately into the fetal position. Amira burst out in laughter. 

“I can’t believe he actually thought you were a boy. Especially after groping your tit.”

Blake grumbled from her legs. “The first time I got to second base…was by someone who thought I was a guy.”

Amira ruffled her short hair. “Well next time we see him, I’ll doll you up and it’ll be a hilarious story to tell later on.”

“Later on? This is so embarrassing now!”

“Let’s go on the slides. That’s what we came here for after all.”

Amira took her hand and dragged her to the slides. There was a short line so they each could ride at the same time. 

When she crashed into the pool below she felt at ease. It was great to be in the water again. The water on her bare chest felt so foreign, yet so natural. Maybe she should go topless more often. She stood up and slicked the water from her legs. Her bare legs.

She panicked and looked down. The oversized trunks were gone. Her carefully shaved pussy was out for all the world to see. She crouched back into the pool, hoping no one would see her. The day just kept getting better and better. The people around her didn’t seem to notice the naked girl.

Blake frantically began looking for the swimsuit. If she couldn’t find them soon, there was no way she could talk her way out of it. 

So many bodies squished into hers. One guy with a volleyball elbowed her chest. Another person swam between her legs. At one point she swore someone squeezed her cheeks. She was so blindly groped and prodded that she felt violated every time someone came near. 

“Hey, looking for these?” 

It was Ali. He held her trunks out to her. Blake turned red and covered her crotch. He offered her a hand.

“Let me help you dry off.” 

“Ali…if I leave the pool everyone will know I’m naked.” She glanced around her. He shrugged as he tossed the swim trunks in. she hastily put them on.

As she got out, they stuck to her skin. She covered herself with a towel before he could see.

“There’s a changing room this way, Amira gave me your bag.”

They walked over. Blake practically ran in, almost crashing into the locker room walls. She breathed a sigh of relief, finally out of the public eye.  

“Thanks for helping me back there. I would’ve been a goner.” She dried herself off, turning around, hoping to preserve some last semblance of dignity. 

Ali suddenly placed his hand against the wall, leaning in slowly. 

“I never thought that the girl Amira would introduce me to would be this daring.”

Ali’s hand caressed her mound through her trunks, there was no way now she could keep pretending to be a boy. 

“How did you -”

“I knew the second you walked in. Amira was always telling me about you, Blake.” He placed his hand on her right breast again and slowly massaged his thumb around her nipple. “You’re too cute to be a guy. The whole time I was thinking about you shameless whore.”


“What else would you describe a naughty girl who spent the past hour swimming around with her tits out letting the whole town see. Not to mention one who stayed in the pool completely nude.”

He leaned in closer. She could feel his erection press into her swimsuit. 

“To think you would be topless in my pool deserves punishment, don’t you think?”

“But – but what if someone walks in?”

“No one would walk into a closed off area. We have all the time in the world.” He grabbed a fist full of her hair and smirked. “Amira knew I was into tomboys, but you sure surprised me.”

With one hand he eased her out of the swim trunks, leaving her completely exposed in the cold locker room. She was already dripping in anticipation. 

He pulled off his shorts, revealing his erect penis. “God you’re such a tease.” 

He grabbed her sharply and moved her onto a locker room bench. She could feel the metallic lockers press into her back. Ali moved in closer.

“What are you doing?”

“What does it look like I’m doing?” 

He opened her legs and inserted himself inside. The sharp squeeze she felt between her lips made Blake want to cry out but Ali placed his hand on her mouth.

“Say anything and I’ll report your little display to the authorities, or even your school.”

She quickly nodded. His hands moved to grip her hair instead as he rhythmically grinded his hips into hers.

“Thank god Mira left enough for me to grab.” He murmured as his thrusts grew more frantic. Blake starred up into the ceiling, praying that he would finish fast. A small tear fell down onto her hand. Every push hurt, and he wasn’t trying to be gentle. 

He thrusted a few more times before he came. His heavy pants echoed in the empty locker room. The deed was done. 

Blake kept silent, scared he would still do something to violate her further. But he did nothing but slip his swim trunks back on. Right before he left he turned to her, still sat on the bench still trying to process what happened. 

“Hey come back again tomorrow.”

He smiled as he draped a towel over his shoulders. “Yeah, your punishment isn’t over.” 

Blake collapsed back onto the cold locker room bench. She was still heavily breathing from being fucked like an animal. Her body was cold except the still warm cum dripping from below. 

The reality of being Ali’s fucktoy for the rest of summer started to hit. She curled up into a ball and gently touched her hair. Amira and Ali must’ve been planning this from the beginning. 

She groaned. She was still sore from Ali’s jackhammering. One day, she swore, she would make the two of them pay.


Writer’s note: next story will be either another about Sabrina’s adventures or a Christmas themed one

enjoy! (>^_^)>

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