Tomboy's Folly/June 13th
Tuesday, June 13th
It was past noon when Riley's mom decided she'd moped enough and stormed into her room, throwing the curtains wide to let in the midday light. Riley had decided she didn't want to get out of bed ever again and burrowed underneath her pillows.
"Riley, I know you're upset but it's time to get up! It's past noon, for goodness sake!" She tried tugging the blankets off her 10 year old daughter, but Riley refused to let go. Her mother wasn't very strong, and she couldn't get the blankets away. Finally she gave up with an exasperated sigh.
"Fine, wallow in pity! Life isn't always fair you know, Riley!" her mother stormed out, slamming the door behind her. "Let her be, honey." Riley heard her father say through the thin walls of their house. "She'll come out when she's ready."
Several hours passed before Riley was momentarily jerked out of her loop of pathetic self-pity by the sound of their doorbell. "Probably just another of my dad's 'work buddies'..." she grumbled under her breath. A moment or two later she heard a small knock at her bedroom door. Riley ignored it. A minute passed, then she heard her mother's voice through the wall. "Go on in - if anyone can cheer her up it's you."
The door opened. Riley scowled into her pillow, wondering who had come to bother her now. Was it her uncle? He wasn't as funny as he thought he was... Still grumbling, she let out a yelp as something slammed into her back.
"I knew you would be devastated by the news, Riley, but c'mon! Get up, come outside and play with me!" Riley knew that voice all too well, and unlike her mother and father, her best friend Megan Johnson would not leave her alone until got what she wanted... which in this case was Riley dragging her sorry ass out of bed.
"Meg... I'm not in the mood!" Riley growled. Meg only shrugged and whipped the pillow out of her best friend's grip after Riley let her guard down. Snarling, Riley flipped over and grabbed for the pillow. Meg hopped off the bed and out of her reach. "You want it - come and get it!" she said with a grin, standing with her feet braced and flapping the red pillow like she was trying to taunt a bull into charging.
Riley's mouth twitched, almost smiling. Meg always knew how to cheer her up. She flipped onto her hands and knees and put two fingers up by her ears like they were horns. "Grrr!" she said, pawing at the bedsheets with her knees like she was a bull pawing the ground. "Toro, toro!" said Meg, and Riley launched herself off the bed at her friend. Instead of whipping the pillow away, though, Meg reached out and caught her friend, and the two of them slammed into the wall lightly, both of them giggling.
"Girls! Take the roughhousing outside!" Riley's mother called from the kitchen. "Sorry, Mrs. Wendel!" shouted Meg. "We'll go outside!" Meg turned her attention back to Riley. "Now get dressed stinky, I found a new trail for us to explore!~" She gave Riley a noogie, making the girl flail out of her grip. "Fine, fine!" she said, stalking over to her dresser.
Riley and Megan had been nearly inseparable since Riley's family had moved in next door to her six years back. They were closer than sisters and did everything together, and she was the main reason Riley was such a tomboy when her parents were such big delicate indoor flowers.
"I asked your mom if I could come over and see you." Meg said. "She said it's fine!~" Riley shook her head. "Oh, and of course it never even DAWNED on you to ask my opinion..." she grumbled as she threw open her dresser and started grabbing clothes out of it.
"Of course it dawned on me. I just didn't ask cuz you might have said no!~" Meg said with a grin. With clothes in hand, Riley spun around and stuck her tongue out at her friend. "Pfft, sooooo considerate..." she rolled her eyes, which only made Meg snicker.
Riley tossed her change of clothes onto her bed and started to strip off the clothes from yesterday she'd slept in. They were not bashful about being unclothed around each other, so Riley didn't even spare a moment's thought. The shirt Riley was currently wearing was probably Meg's anyways, as they shared their clothes so often they would tend to lose track of whose was whose.
There was one article of clothing they didn't share... and Riley was reminded of that fact once again as she stripped off the football shirt she'd been wearing. Her chest was still completely flat at age 10, much to her annoyance. Meg's breasts had already started filling in last year, and she already had a collection of cute bras that Riley couldn't share with her yet.
Riley scowled down at her flat chest, her back turned to Meg. She didn't really care about the breasts themselves, and she wasn't looking forward to all that messy womanly stuff she'd have to put up with when he hit puberty. It just irked her that this was now the one thing in her life that Meg couldn't share with her.
Shaking her head to clear it, she went back to undressing, pulling off her loose fitting basketball shorts. Riley was quite lean for a girl as athletic as she was. She was only four feet tall at age 10 - another sore spot between her and Meg, who had begun shooting up and now towered over her at nearly five feet.
Clad only in panties and socks, Riley walked over to the mirror on her dresser and stared into it, running a brush through her dark brown hair. Riley's skin was quite fair like her parents, though she had some intense tan lines from all the time she spent outdoors in the long summer months. Freckles dusted her face and upper arms, on her flat, muscular belly, her lithe legs, and all around her slim shoulders.
Riley looked into the mirror, her amber eyes flashing in vexation on her small face as she worked out several knots from her shoulder length hair. Meg's voice broke through her vexation. "Did you hear the bullshit? The boy scouts' trip through the mountains is still going to happen. That means my stupid brother still gets to go on his trip with his troop."
Spinning around, Riley dropped her hairbrush. "WHAT!?" she shouted. "That's so unfair! How come they get to go!?" Riley seethed in anger, her fists clenched together so hard that her nails dug into the flesh of her palms. "I know right!?" Meg said, hopping onto Riley's bed. "I kinda wish we could just go with his troop... but they'd never allow that."
Meg looked over Riley's body as she stomped around the room trying to work out her frustration. 'She still hasn't bloomed at all...' Unbeknownst to Riley, Meg was actually jealous of HER for not hitting puberty yet. Her breasts were annoying, and got in the way of things far too much. "Riley, you're so lucky you don't have to deal with THESE." She said, grabbing her stupid breasts and letting them drop. "I.. hate them... and I wish I still had a boyish body like yours."
Boyish body... Those words made Riley half, an insane idea forming in her mind. "Meg, that's it!" she whooped, and ran over to hug her friend. "I'll pass as a boy and join the boy scouts on their trip!" Meg blinked at her best friend. "You... you can't be serious?" she said warily, studying Riley's small face. Recognizing the determined look in her eyes, Meg thought to herself 'Uh-oh...'
"Riley, c'mon that will never work." Meg said, thinking she should at least try to stop her friend before she did something crazy. "I mean... you'd never be able to fool your parents!" Riley put her hands on her hips. "Can so! I'll just.. Ummm..." She stopped, trying to work out how she'd actually pull this off.
Meg sighed.. They were in the same Girl Scout troop together and Meg was as bummed about not being to go on this trip as Riley was. Part of her wanted to stop this before it got out of hand... but if there was even a chance they could still go on this trip, she was going to try it!
"Sigh, I know I'm going to regret this..." Meg began. "...but I think I know someone who can help. I was going to surprise you with this later, but you know my big sis April who I always told you about? Well she's finally got time off and is actually visiting us for the first time in like EVER!"
Riley's jaw dropped. "April is here? I've always wanted to meet her! But what does that have to do with our plan?" Meg giggled. "C'mon, I told you why my parents got fed up and set her to boarding school. She's like, some kind of expert at fooling parents. If anyone can hatch a plan to pull this off, it's her, right!?" Riley's face brightened. "Do you think she'd help??" Meg snickered. "Only one way to find out. Hurry up and get dressed and I'll introduce you!~"
Riley let out a whoop, hugging her best friend tightly before leaping off the bed. In her haste she tried to take her panties off too quickly and stumbled with them tangled around her legs. Meg giggled and tugged her friend onto the bed with her, trying to help her untangle her panties. She refused to acknowledge the warm feeling that flooded over her as her best friend giggled and squirmed in her lap, though she was acutely aware that the tips of her growing breasts felt tight...
Laughing, Meg helped Riley out of her panties and shoved her off the bed, her breath catching in her throat. What was wrong with her... Buck-ass naked, Riley stuck out her tongue at Meg with her hands on her hips, not noticing that Meg's face was a bit redder than usual beneath her red locks. Meg was only half a year older than Riley and they were still in the same grade. Red curls framed her small face and contrasted wildly with her ice blue eyes. Her build was a bit stockier than Riley's, with broader shoulders and hips than her friend.
"H-Hurry up and get dressed!" she said breathily, tossing the clothes Riley had left on the bed to her. Riley caught them with a smirk and grabbed the panties, bending over to put them on. As her best friend bent over, Meg found herself staring at Riley's hairless slit now visible from between her slender, muscular legs. The feeling only lasted for a moment before Riley pulled her panties up to her hips... Meg was now more confused than ever. She'd seen Riley naked hundreds of times... what had changed?
Riley tugged the short shorts she'd picked out for today. They were starting to get a bit too small, and rode up on her tight little ass a bit. When she struggled to get the shirt on over her head, Meg had hopped to her feet and started trying to help her without thinking. "H-Here, let me help..!" she said, blushing as she tugged the shirt down over her friend's smaller frame.
"Ah, thanks. I guess I'll have to get rid of this one soon, sigh... Remember when we bought this shirt together after mowing everyone's lawns?" Riley said, lost in her reminiscing. "Y-Yeah..." Meg mumbled, shaking her head to clear it. "Things seemed so much simpler then..." Riley blinked at her friend. "What do you mean by that?" Meg shook her head. "Um, n-nothing! Let's go see my big sis!~
"Wait, what about your brother?" Riley asked. "How are we gonna convince him?" Meg shook her head. "Let's just say I got some dirt on him right now, tehehe. Just leave him to me."
...
"So this is the famous Riley I've heard so much about! Nice to finally meet you!" April extended her hand to Riley, who shook it eagerly. "It's so nice to finally meet you, April!" Meg had told her so many tales about her badass older sister. April was 23 years old, and Megan had always looked up to her. She'd followed her big sis around everywhere when she was little, until her parents got fed up with her and decided a boarding school would be the only thing in the world that could possibly sort her misbehavior out. From what Meg had told her of her sister's last few years, though, Riley was preeeeety sure that idea had failed.
April was almost 6 feet tall and solidly built, her arms and legs muscled so heavily it made Riley jealous. April's passion was free climbing, and she'd been climbing mountains with her bare hands all over the world between her tours as an enlisted soldier. "Now, tell me what's going on... How the hell did your big hiking trip get canceled?" April ushered both girls into her room in Megan's house and closed the door behind them.
Riley and Meg told April her the story about what had happened on the trail. "So, some little snowflake didn't follow the rules and broke her arm, and now you girls can't go on your trip? That's insane! I should pound that good for nothing mom for ruining my baby sis and her best friend's trip!" April pounded her fist in her hand. "That's not even the most bullshit part, either!" Meg said. "The boy scouts still get to take their trip! It's only our troop that was affected!"
April scowled. "Wow, that blows! This is a real shit show, Meg! I wish there was something I could do to help." Meg looked away slyly from her older sis. "Well... maybe there is something you could help with." April's eyes narrowed and flicked back and forth between the two girls. "Shhh..." she said, and went to the door, opening it gently and sticking her head out into the hall. Closing the door just as quietly, she grabbed both girls by the forearms and dragged them into the private bathroom her room possessed.
Thrusting both girls inside, she closed the door behind them. "I know what you're thinking..." she began. Meg put her hands on her hips. "No you don't!" April chuckled as she looked down at her little sister. "Yes, I do. You're thinking you could pass as boys and go on the boy scout's trip." Meg's jaw dropped. "How could you..."
April laughed. "Oh c'mon, sis don't look so surprised. There's only one way you could go on that trip now, and the only reason you'd come to me would be if you needed a brilliant and sneaky plan." She folded her arms on her chest, thinking. Riley and Megan looked at each other, waiting patiently while April considered. This would be a real challenge to pull off... she liked that.
"Alright, I'm in." she said finally. Both Riley and Meg's faces lit up. "You'll help!?" April nodded. "A few rules first! Rule number one: you do everything I say, without question! Is that clear!?" Both girls stood at attention. "Ma'am, yes ma'am!" they chorused in unison. "Rule number two! I was not involved in this plan! If you get caught, you're on your own! Got it?" Both girls grinned. "Ma'am, yes ma'am!" they said together again.
"Very good! Now strip off your clothes, both of you!" Riley and Meg both took a step back. "What!?" exclaimed Meg. "Why..?" Riley asked, her face flushing slightly. "I said no questions, ladies! I need to see your bodies out of those baggy clothes to see if you can pass as boys!" Riley looked at Meg, who shrugged at her and grabbed the bottom of her shirt, pulling it off over her head and exposing her bra. Riley felt a little uncomfortable, but shrugged and figured if Meg didn't mind then she didn't either.
Both girls stripped off their shirts and shorts in front of April while she watched. "Take your bra off, too, Meg. You can both keep your undies on for now." Meg nodded and unhooked her bra, letting it drop to the floor. Her breasts had grown quite a lot already, and were very noticeable against her chest as opposed to Riley who was still pretty much completely flat.
Once they were both stripped down to their undies, April walked over and looked down at both girl. She lifted up Meg's arm and shook it, watching her breasts jiggle, then did the same to Riley. Then she ran her hands down their sides, feeling the curves of their hips. Riley felt a bit weird feeling April's callused hands running over her mostly naked body, but she held her tongue. She was determined to see this through!
April grabbed both of Megan's growing breasts and pushed them around. "Sis, do you really need to do that.. it feels weird..." she complied, her face flushing slightly. "Hey, I'm just being throughout!" she said, still massaging and tugging on her little sister's breasts. "When'd you get so big?" she said, making Meg blush. "This year... I hate them. Can you pull them off for me?" April chuckled. "Oh you'll want these later, trust me." she teased.
April let her sister's breasts drop and stepped back, moving closer to Riley. "I'm sorry Meg, but I don't think you can pull it off. Riley definitely can, though." Grinning, she looked at Riley again. "I mean heck, are you sure you aren't actually a boy? You sure look like one!~"
Meg pouted and crossed her arms over her annoying breasts. "I'll.. I'll bind them flat! Yeah!" April shook her head. "Have you ever tried doing that? It will hurt like crazy, trust me." Meg scowled at her big sis. "I'll do it! You'll see!" She raced out of the room, leaving April alone in the bathroom with Riley.
April leered down at Riley, who gulped. Meg's big sis was so cool... but really intimidating! "Tell me the truth - you really are a boy, aren't you?" she teased, making Riley blush. "O-Of course not! I'm a girl just like you..!" April snickered. "Really? Well I want to be sure!~" Riley backed up until she met the cold tile of the far wall. "H-Huh? What do you mean? You don't believe me?" April advanced on her until she loomed over her small girl.
"I just wanna check, I mean can you blame me - you've even got a boy's name!" She slid one of her big hands down to the young girl's belly. "R-Riley is a girl's name, too!" she said indignantly, blushing red as April slipped her hand down lower.
"Well I'm just going to check real quick... I'm sure you don't mind." she slid her hand down underneath Riley's panties. "H-Hey, I d-do mind! I'm not a b-boy!" she stammered. April ignored her protests and slid a coarse finger down the little girl's slit. "Hmm... I don't feel a penis. But you're so young that I can't tell." She grabbed at the lip of Riley's panties and pulled them down a bit.
"S-Stop..." Riley mumbled, feeling funny. April admired the young girl's hairless slit, pinching it with her fingers. "Ah, I guess you really are a girl. Coulda fooled me, ehehe!~" April patted her on the tummy. A voice from the door made April flinch. "April! I need help tightening this!" April quickly pulled Riley's panties back up and turned as her sister walked back in, trying to bind her chest flat with medical gauze while walking.
April went over and tried to help her. "Oww!! OWWW!!!" Megan cried as April tightened the gauze. "Meg, sweetie, I really don't think you can do this..." Megan scowled. "Y-Yes.. I c-can!" she said, pain filling her voice. Riley looked and saw that her friend's boobs were flattened, but even so there was still a noticeable bulge. "Sorry, baby sis. It's still too big, and you're in way too much pain to do that all the time."
Meg sighed, her shoulders drooping. "Oww... I k-know you're right. Cut me loose..." April undid the bindings, and Meg's boobs flopped back down to their full size. "Riley could definitely pull it off, though. What do you say Riley, you still game to pull this off?" April said with a wink. "Y-Yes..! I want to go more than anything in the world!" she said, her small face filling with iron-clad determination. "Just tell me what to do!"
April chuckled to herself, thinking how cute Riley looked with her game face on. Meg sure knew how to pick a best friend, she had to hand it to her!
"Aright, so here's the plan!" April said to the two girls shivering in their undies in the cold bathroom. "Your parents have never met me before Riley, so this should be easy. I will post as a girl scout leader from another town, and say that we heard that your troop couldn't go on the trip and decided to take your spot. I'll say that we have space for one more girl and I'll tell your parents I talked to your leader at a meeting last night and she mentioned how sad you were that you couldn't go, and offered to take you with my troop."
Meg grinned. "That's a great plan, sis! You always make up the best stuff!" April smiled and ruffled her little sister's hair. "You know it! Now, we still need to make them want to trust me. To them I'll just be some strange woman they don't know offering to take their little kid into the woods with me." she paused, thinking. "Hmmm... if I brought my 'daughter' along, they might feel different. Is there anyone from your girls' troop that Riley's parents haven't met? It needs to be someone you can trust not to spill the beans."
Riley and Meg looked at each other. "Tanya?" Meg suggested. Riley nodded. "My parents haven't met her, she'd be perfect." Turning to April, Riley explained. "Tanya's always getting into trouble for pulling pranks, and loves messing with people. She'd probably see this as one huge trick and be totally into helping."
Hearing this, April chuckled. "Sounds like me kind of girl! Meg, do you know where she lives?" Meg nodded, jumping up and down. "She lives just down the street! I'll go see if she's home! Be right back!~" April chuckled as Megan furiously attempted to redress as quickly as possible. With her clothes back on, Megan raced out of the room. She shut first the bathroom door, then the bedroom door behind her.. leaving Riley alone with her big sister.
April turned her attention back to little Riley and walked over, making her gulp. She relaxed when April stopped a few feet away and extended her hand. "I just wanted to take the opportunity to thank you for taking such good care of my baby sis. My only real regret from leaving was that I had to leave her behind, too. It broke my heart, but I can see I wasn't needed. She found someone just as stubborn and awesome as she was to be besties with!" Riley blushed at the compliment. "Um.. I don't know what to say... I mean... she's my bestest friend in the whole world!"
Riley shook April's hand, gripping it firmly. April shook back, squeezing Riley's smaller hand hard enough to make her wince. "It shows. I'm glad you're here for her, and I am very happy to be able to help repay you a bit for all you've done for her." Noting Riley's face looked a bit flushed as she shook her hand, she grinned internally. "Okay, squirt! Get dressed before Meg get her with Tanya! I'll be in the bedroom." She left the bathroom, closing the door behind her. Riley was relieved she hadn't tried to touch her between her legs again... or was she? She shook her head, trying to clear it, then picked her clothes up off the floor.
...
Riley laid awake in her bed that night, thinking. Her parents had bought the ruse - Tanya had been more than happy to help, and April had successfully convinced her parents. Now she just had to wait two days... she could barely hold her excitement!
However that wasn't the only thing on her mind this evening... She couldn't stop thinking about how April had touched her between the legs. It felt weird... but not in a bad way. Frustrated and confused, Riley pulled her pajama bottoms down underneath her covers. She wanted to know what was going on...
Riley poked at her puffy slit with a finger, and noticed a strange twinge feeling flood her mind. Was something wrong with her? She never felt like that when she touched her vulva after wiping from using the toilet, or when she cleaned it in the shower.
Timidly the young girl ran a finger along her slit slowly from the bottom up. The feeling was odd, but kinda pleasant. She was starting to wonder what else to try when she gasped as a feeling of pleasure she'd never felt before flooded her brain. Her finger had hit some kind of little bumpy and the feeling was amazing!
She pulled the covers down and bent over, pulling her pussy lips apart to look at what she'd hit. Riley examined her little clit, wondering what it was. She poked it again and her eyes went wide, the feeling making the young girl pant. "What is this..." she gasped to herself. "M-Maybe I can ask Meg... or.. or April..."
A fear ran down her spine - what if something was wrong with her that got in the way of their plans!? Taking deep breaths to calm down, she pulled her pajama bottoms back up over her thighs. "I'll w-worry about it in the m-morning!" she decided, and pulled the covers back up, trying to get some sleep.
...
Megan was fast asleep that night when April slipped silently into her room. Creeping up on her bed, she put her hand over her sister's mouth and put a finger to her lips. Meg jerked and flailed, but calmed down when she saw it was only April. She scooted over and let April slip under the covers with her, though there wasn't much room in the bed for her.
April pulled her baby sis up against her and snuggled with her, gently stroking her hair. "Sorry I couldn't help you, sis. You just can't pass as a boy anymore." Megan sighed. "I know... Thanks so much for helping Riley, though! At least she gets to go..."
Meg felt a big hand tilt her head to the side. April looked at her lil sis and smirked. "You like her, don't you?~" Meg blinked rapidly. "H-Huh? She's my best friend, of course I like her." she replied, confused by April's meaning. April chortled, patting Meg on the cheek. "Nah, little sis. I mean you LIKE, like her! Admit it, I can tell!~" Meg felt her face flushing and jerked out April's grip, turning her face away. "I-I... I don't know what you mean..." she said, though that was a lie: she had realized what her sister was implying.
"Oh c'mon, don't be shy - it's adorable! You two would make the cutest couple, ehehe!~" Meg swallowed. "You mean like, as in... love? I'm f-far too young for that st-stuff..." April chuckled. "Nonsense - I was younger than you when I started!~" Leaning down to whisper in Megan's ear, April smirked. "I think she likes you, too..." Meg twitched, turning her head to look at her sis again. "H-Huh? How can you t-tell?" she stammered, her pretense at denying the claims gone in an instant.
"Experience my dear sister... I can spot the signs." April reached down and began rubbing her little sister's nipples through the thin fabric of her night shirt. Megan flushed deeper and her breath caught, but she didn't try to pull away. April leaned in so close to Meg's ear to whisper into it that her lips brushed the earlobe as she talked. "Since I couldn't help you get into the boy's troop, I did you one better. I got your little friend started for you..."
Meg shivered and trembled at the strange but pleasant feeling of her sister lipping her ear. April smiled and continued, "I bet she's touching.. herself right now. Can you picture it?" Megan found herself unable to resist thinking about Riley lying in her bed touching her gorgeous smooth slit. April moved one hand down from her sister's breast and pressed it against her slit through the fabric of the panties she wore at night. April peeled back the fabric of Meg's panties, noting that she had yet to grow any hair down there before letting the fabric go and moving back to touching her through the fabric, not wanting to push her too far for her first time.
Megan shivered at the touch, imagining it was Riley touching her there... Her pussy grew wet from the thought, and April chuckled softly as she felt her baby sister getting wet. "If she's as curious as you say... I expect she'll ask you about it tomorrow. You can make your move then, ehehe!~" Meg wasn't listening, as her mind was filling up with mental pictures of Riley and her touching each other between the legs...
Suddenly she felt something hot and wild well up inside her. April clearly sensed it coming, because she put a hand over Megan's mouth before she could cry out. Meg came to her big sister's touch while thinking about her best friend's pussy. Her hips bucked as she rode out her first orgasm. April felt very, very hot watching her baby sister cum in her arms. She couldn't help herself anymore - she grabbed one of Megan's hands and pushed it down her own panties. She'd already shaved down there earlier tonight for Meg's benefit.
April whispered into her sister's ear once more. "Hahh... I bet that felt amazing. I still remember my first orgasm." She moved Meg's hand till her small fingers wet pressing against her already wet adult slit. "N-Now that I made you feel good, y-you can practice on me. Close your eyes... imagine you're touching Riley's vulva." Meg did as she was told, her heart pounding as she pictured it. "Oh god..." she mumbled, and her fingers twitched, sending a wave of pleasure through April.
She decided to let Meg try to figure out what to do for a while, as her voice might ruin the illusion for her. Meg played with April's pussy lips, feeling around them. April noted with pride that Meg's other hand had gone down into her own pants without having to be told. 'Heh, she's definitely MY sister.' thought Meg with an internal grin. April gasped as her sister slipped two fingers inside her pussy and began rubbing them around inside. Meg had done the same with her other hand on her own pussy, and was squeaking and moaning through the hand over her mouth.
Meg just imagined what it would be like to put her fingers inside Riley's cunny... and did what came naturally. Megan's fingers went faster as she pictured Riley's little body panting in her grip. April had to work very hard to stifle her own moans as her little sister's fingers brought her right up to the edge.. and over it. April came on her sister's fingers, just as Meg also came from her own fingering. They lie there for a while, breathing hard.
"Ahhh... Did that feel good sis. Sis?" April checked on Megan worriedly, but she'd merely passed out and was fast asleep. Chuckling, April pulled Meg's hands from both their pants and hugged her smaller body closer to her own, snuggling close before going to sleep herself.
June 14th