Tomboy Best Friend’s Perfect Pussy

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He accidentally sees friend (F19) naked in secluded cabin.
2.6k words
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Constructive criticism appreciated. I understand this story is largely self-indulgent and won't be for everyone. All characters in sexual situations or described sexually are 18 or older. Thanks to HeyAll for his formatting and grammar suggestions.

*

"Hey, bro!" Michael called to Billie as he trotted up a gravel and dirt driveway to the little old log cabin he'd be staying in for the weekend with friends Billie and Matt.

To some it'd be strange to hear Michael call Billie "bro" since she wasn't a boy, but to Michael and the gang she was just one of the guys. A makeshift basketball hoop was set up on an old post at roughly the appropriate height for a basketball hoop. Like most things inside and outside the cabin, the hoop setup was quite rustic.

Billie was taking shots at the basket with an old basketball while waiting for Michael and Jim to arrive. She drained a 20-foot shot before turning in Michael's direction and smiling in greeting, the ball bouncing off a piece of gravel into a group of pine trees.

"Hey, man! Want help bringing anything into the cabin?" she called.

"I think I'm okay, just the one duffel bag, but thanks," he responded, mirroring her smile.

Michael and Billie had known each other most of their lives, being close in age at 20 and 19, respectively, as well as living on the same street in a small northern Midwest town as far back as infanthood. They had walked to school together, practiced sports together at the neighborhood park's basketball court, and even often got in trouble together.

Billie headed to the group of tall pine trees for the ball, pushing branches and walking on cracking twigs in the process. Crashing back out through the branches, she pulled some pine needles from her fiery red hair, twisting her face in annoyance.

Usually described more as pretty than beautiful (not that she liked either description), she had a thin face with striking green eyes, semi-prominent eyebrows that match her red hair, a small sunburned nose, often-flushed cheeks with a dimple on one side, sunburned ears, and a cute chin cleft--although most never dared to describe her as "cute" to her face.

Michael had once suggested actress Sadie Sink as her closest celebrity doppelganger, and Billie didn't appreciate the comparison. She just wanted to be one of the guys, and to be fair, that's how Michael and the rest of her friends saw her. She had always hung out with the guys, seeming to never get along with any girls for any significant amount of time, and that was fine with her.

Raised by a single father, she had always had more traditionally masculine attributes, whether that be her interest in sports, her mannerisms, or how she often dressed in comfortable loose gym shorts and t-shirts in the summer. She sure as shit wouldn't be caught dead in a dress and avoided clothing that would show off her figure, not that she had much figure to show off, being flat chested and having little in the way of flesh on her butt or hips. She preferred it that way, but that didn't stop her from getting into fights with students in school who made fun of her lack of feminine body proportions.

Satisfied she had removed the majority of pine needles, she passed the ball to Michael while he was approaching the cabin with his bag. It was a hard pass that Michael barely saw coming in time to bring up his shoulder as a protective reflex. The ball rebounded off his arm, compressed air echoing inside the ball at the impact. Michael half-grimaced, half-smiled at the unexpected attack as he dropped his bad and rubbed his reddening shoulder.

"Hey, maybe wait until I'm ready and don't have a bag in my arms," he complained.

"Nah, you should always be ready for a pass from your teammate, bro," Billie retorted with a wicked grin.

Michael gave Billie a playful glare while giving his shoulder a few more rubs.

Billie had always been the harder worker when it came to practicing sports. Hell, she was more athletic too and was toned from consistent exercise.

Michael wasn't in terrible shape himself. He wasn't bulging with muscles and didn't have a six-pack, but he got plenty of exercise trying to keep up with Billie over the years. He kept his dark brown hair at a couple of inches, unstyled, and often a bit messy. His pleasantly warm brown eyes and the easy smile he often wore could be described as inviting and friendly.

"Oh, by the way," she said as her mischievous grin transitioned to scrunching up her face in disappointment, "Matt called to say he can't make it tonight since he has a stomach bug, so I guess it'll just be the two of us, unless you want to go back home and come back up here a different weekend."

"Well that's a bummer, although I suppose we shouldn't be surprised; Matt's immune system always seems to be reacting to something," Michael sighed. "I'm up for still staying the weekend though."

After all, Billie was just one of the guys, so it wouldn't be weird for it to be only the two of them in the cabin. Billie's dad might take exception if it were anyone else, but he knew there was no way Michael and Billie would ever get up to any funny business, not the least of which because his daughter seemed to be asexual, having never displayed any romantic interest in anyone.

Michael picked his bag back up, walked several steps up the small porch to the front door, and opened the door to reveal the inside of the small one-room cabin. The cabin was so simple that it had no electricity or plumbing, relying on lanterns and the fireplace for light and boiled water from the lake for consumable water.

Three hours north of their town, Billie's father had bought it as a vacation spot. It was the most he could spend on a vacation property, but what it lacked in amenities it more than made up for in the beauty of its natural surroundings. It had a sparkling lake bountiful with fish and an untamed forest for miles, far from the noise and light pollution of the nearest town.

There was a bunk bed and cot on one side of the room. A basic wooden table with chairs stood in the middle. A simple old mirror hung on the wall opposite the bunk bed, above a roughly made dresser. Michael dropped his bag on the bottom bunk before heading back outside.

Billie held the ball and had been lining up a far shot, but Michael snuck up and snatched the ball out of her hands and went for an easy layup before passing the ball back to Billie. Billie, equal parts annoyed and amused, measuredly dribbled the ball towards Michael before suddenly feinting to her left and then driving hard to the right. She dashed around Michael easily and moved under the basket for a reverse layup, the ball rolling in perfectly.

"Maybe you shouldn't defend so tightly on someone who's so much faster than you, dummy," Billie chuckled.

They continued playing until early evening, at which point they put on their swimsuits to rinse off their sweat in the crystal clear water of the very cold but refreshing lake. After drying off, they cooked hotdogs over the firepit outside. Billie put down six hotdogs loaded with condiments in record time.

"You wouldn't think someone so in shape would be able to eat like that," Michael laughed after he had asked how many she'd had.

She shrugged nonchalantly as she began putting together the fixings for what looked like would be a record-setting sized s'more.

It was nearly dark out, so Michael suggested they go inside, start the fire in the fireplace, and play some of the old board games kept in the cabin. After a couple of hours of mostly losing to Billie, they got in bed, with Michael on the bottom bunk and Billie on the top. After talking for another hour about everything from life goals to debating which region of the world had the best food, they both drifted off to sleep.

****

Billie's eyes fluttered open, feeling the mild pressure inside of needing to pee. Hopping down off the top bunk, she tip-toed to the door, put on her shoes and hoodie, and padded outside toward the outhouse in the cold night air. It was quite dark, with no moon to be seen behind the cloud cover, but she knew the way. Various bugs buzzed and frogs chirped from the woods and lake, filling the night air with the sounds of nocturnal creatures. After finishing her business in the outhouse, Billie started walking back toward the cabin.

Hearing the hoot of an owl in a tall pine far above her, she squinted up at the branches to try to spot it while continuing to walk. However, without her eyes on the ground, she didn't notice a hole large enough for her foot to fall into, causing her to stumble into a muddy puddle, splashing mud all over herself.

"Damn it!" Billie whispered fiercely.

"Hoo, hoo hoo, hooooo," the owl responded. Mud-splattered, Billie glared up at the tree, still unable to spot the owl that was apparently mocking her in the dark.

****

Michael woke up with a start to his bed jostling, and he raised his head from his pillow. Billie was standing on the edge of his lower bunk, unknowingly moving his bed enough to wake him. He could barely make out her outline in the dark, as the fire had decreased to red embers and the small cabin windows didn't allow in much light from the cloud-covered moon. Figuring she had just gotten back from using the outhouse and was climbing back up to her bunk, Michael put his head back down and closed his eyes.

After a minute, he felt her step off his bed edge onto the floor. Opening his eyes back up, he sat up and tried again to make her out in the darkness but couldn't. Just as he opened his mouth to ask her what she was doing, the clouds outside broke, flooding moonlight into the small window above the bunk bed. Michael's mouth was still open, but now due to shock instead of in preparation to speak.

Billie stood in the moon's natural spotlight, completely naked, wiping mud off her body with paper towels and wipes. The moonlight was bright enough coming over the bunk bed that she wouldn't be able to see into the dark lower bed to notice that Michael was awake, but she was lit up perfectly for Michael to see the naked body of his best friend. Transfixed by the sight, he didn't turn away, and not wanting to embarrass her (and in truth, he also didn't want to interrupt the scene before him), Michael didn't say anything.

Twisting, bending, and otherwise moving in the moonlight to wipe away the mud on her body, Michael ran is his eyes down Billie's lithe small athletic body that previously he had only thought about in the context of her sports abilities. Her jaw was clenched and lips pursed in frustration at the muddy predicament, her expression for some reason making her hotter.

Her slender neck sloped to her thin but toned shoulders and her striking bare clavicle. Michael's eyes made contact with Billie's perky a-cup breasts, rising and falling with each breath in frustration at her predicament. Each little breast had a small pink areola and perfect nipple standing hard at attention in the brisk night air. Her belly was tight and smooth, with the smallest hint of some extra feminine softness below her belly button. Natural to her thin build, her waist and hips were slight. Her hip bones were quite noticeable and, to Michael's mind, incredibly beautiful. Michael noted Billie had a moderate arch in her lower back that pushed out what he realized was a delicate, exquisite little ass, more prominent than he'd ever noticed before and, frankly, quite adorable.

Billie turned her hips towards Michael as she twisted while cleaning, and Michael got his first glimpse of what was in his opinion her best feature of all: as her hips turned, a perfect pink bald pussy came into view, the outer labia puffy with an idyllic coin slot slit going down the middle and no inner labia visible.

"She must wax it for swimming," Michael reasoned in a passing thought.

Having apparently cleaned herself off to her satisfaction, Billie looked down at her pile of muddy clothes, and Michael realized she likely needed her clean clothes that were up on the top bunk in her bag. Almost in slow motion from Michael's perspective, he watched as she moved toward the bunk bed, still completely exposed, her beautiful small breasts pointed toward Michael in her direction of travel. She stepped up on the edge of the bed and began rummaging through her bag--her pink cunny now at direct eye level with Michael, inches away.

Without realizing it, he was breathing harder, and Billie must have physically felt it because her thighs suddenly squeezed together and she let out a small gasp. For a moment she moved her hand down to her soft pussy folds, cupping herself in what appeared to be pleasure for several seconds, her thighs tightly held closed. However, she didn't otherwise react and eventually resumed rummaging through her bag, as she must have assumed the stimulation was from a draft in the cabin, which was a fair assumption based on the condition of the cabin.

After she rummaged around in the dark for another minute, Michael noted some moisture showing up from her slit, and he smelled an unfamiliar to him but intoxicating scent. Was she really so sensitive as to be turned on so easily? Michael's cock was already stiff, but this fact brought his cock to a new level of hardness.

Having finally found all the clean clothes she needed, she pulled herself up onto the bunk, where the bed moved as she changed.

After a couple of minutes of silence, the bed above Michael began moving differently--in a rhythmic fashion that Michael suddenly realized was Billie masturbating! Looking at the mirror on the opposite wall, Michael could see Billie up on her bed with her legs spread wide, eyes closed, face contorted in pleasure, and hand moving frantically under her loose shorts, eliciting small gasps of gratification from her.

Suddenly she let out a series of squeaks and grunts, and one of her legs slipped and hung down in front of Michael, twitching in time with her grunts while her toes curled tightly and slim calves became taught.

After a series of seconds of the powerful orgasm with her accompanying little squeals and muscle spasms, Michael heard Billie let out a long shuddering sigh, and her leg relaxed and dangled. He could see her face vaguely in the mirror, and her eyes were half closed, chest rising and falling deeply in recovery after such an intense flood of dopamine, her hand still resting down the front of her shorts.

After a minute, Billie slowly and shakily lifted her dangling leg back up on the bed, cleaned her juices off her hand with a wipe, and curled up and fell asleep in short order, apparently getting exactly what she needed for falling back to sleep.

Michael sat in bed for another hour, hardly believing all that he had seen and heard that night. He had never felt any attraction to Billie before; after all, she was just one of the guys.

Despite his cock being desperate for release and his newfound animalistic desire to be inside his best friend, who was a mere few feet above him, eventually he was able to drift back to sleep.

TO BE CONTINUED...

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14 Comments
InvokeInvokeover 1 year ago

Really loved this

InvokeInvokeover 1 year ago

Really loved this

32aa32aaover 1 year ago

Love the story. Love the description of Billie standing there nude.

Tomboys are a special breed. Comfortable in their own skin. Not caring what others think. And then, on those rare occasions, the tomboy transforms into a 'woman' for her lover. Showing the soft feminine side of her, that only her lover has the pleasure of witnessing and enjoying.

Well done.

MADDOGINTEXASMADDOGINTEXASover 1 year ago

I really liked this short story...details were enough to flesh it out...

Seemed like Billie "may" have suspected Matt was awake?? And she certainly was not too shy to masturbate like that, with him in the lower bunk...

Five**5**Stars, and going to next story, chapter. I hope you post more to this very well-written tale...😀🌠🌠🌠🌠🌠

AnonymousAnonymousover 1 year ago

I love tomboys! I had some great friends who were tomboys growing up, and many of them turned into wonderful, interesting and attractive women. I wish there were more tomboy stories on Literotica! Looking forward to more!

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