Becca the Bold: Cumming Switchbac

A continuation of the Becca the Bold journey. While not required, previous works will help understanding and are published in order accordingly.

The door to her room opened, Becca sitting up with a jolt in her penthouse bedroom, as a man shuffled in and announced his arrival.

"Good morning! I am Vincent, Miss Hannah has provided you these clothes for your day," he proclaimed, dropping some clothes on a chair in the corner. Just like every other hotel room, this one had the cuckold chair in the corner as well. Even on in the penthouse, people enjoyed being dirty. "Clean up and get dressed, breakfast will be in the car, we leave in less than thirty minutes."

Having showered the night before, she rifled through the pile to see what she had been given. Excited, she realized it was all designer clothing, brand new and the right size, perhaps a little snug. Miss Hannah had provided her with hiking boots and good socks, a pair of yoga pants, sports bra in her size, and a black, silk thong with the word SLUT embroidered in gold on the front. The final item included, with a twinkle that caught her eye, was a small metal anal plug with what looked like an actual precious stone in the handle. The green rock shimmered in the light, Becca eyeing it greedily. Snatching it up with her hand, she stuck it directly in her mouth, sloshing it around before refocusing on getting dressed.

Still with the toy in her mouth, she put all of her clothes on except for her socks. Sliding the toy out across her lips, she pulled her pants down a little, reaching between her legs under her thong, and sticking a finger in her throbbing hole. Sopping, just as she thought. Taking the finger from her snatch, she brought it to her nose and smelled her juices, before sucking her finger into her mouth. Still holding the butt plug in her hand, she fingered her juices into her backdoor a bit, stretching herself slightly. Taking out her finger, she placed the toy at her tightest opening, making tiny thrusts until she reached the midpoint. She felt her ass closing around it as she slid it in a little deeper, feeling the pressure inside her loins.

Pulling her pants back up, she sat down gently, feeling the toy adjusting and moving slightly alongside her shifting. She grinded her ass into the bed a bit, before taking a breath and calming herself down. Not without permission, she thought. Putting her socks on quickly, she slid into her boots and hopped up, heading for the door and proud that it had only taken her ten minutes. In the penthouse lobby, Vincent, the same man who had awoken her, was waiting with a smile. Tall and handsome, Becca found him easy on the eyes. Appearing well built she admired his physique before noticing his snug pants, and the bulge lingering in the front. The elevator's arrival once again snapping Becca from her daydream, the door opened and they boarded, riding down as silent as she had been the day before.

Downstairs in the hotel lobby, they headed for the front door where the car was already waiting outside. He opened the door for her and she climbed in, a waiting Miss Hannah scrolling through her phone on the far side of the back seat. Pausing, she looked up at Becca and smiled.

"Finally," she said, spreading her legs immediately and pulling up the front of her skirt, toying her pussy at the sight of her Slut. "I had wondered if maybe the experience wasn't right for you..."

"Quite the opposite actually," Becca responded, noticing the rest of what Miss Hannah was wearing.

Dressed in matching outfits, except for the lower half, Miss Hannah looked Becca up and down and nodded with a smug look.

"Come on now. We have views to see."

Becca fastened her seat belt and noticed a fruit tray on the chair across from her. Reaching for a piece, Miss Hannah slapped her hand. Immediately understanding her mistake, Becca decided to try again.

"May I please have some breakfast, Miss Hannah?"

"Of course," she replied, as if the hand slap never happened and the food was for her the whole time. "You need to be full for today's hike. Big things ahead."

Becca proceeded to enjoy her breakfast, even remembering to ask for a bottle of water before reaching for one. They departed the city and took the highway for a bit, reaching their exit in about 45 minutes. Still traveling in silence, they drove another 15 minutes before arriving at their destination.

Parked, Vincent turned off the car and exited, standing guard outside the side door.

Miss Hannah finally broke the silence.

"Slut, make me cum before we hike. Down on your knees."

Still sitting with her skirt up, she opened her legs wide, putting her right foot up on the chair in front of her, her hiking boot pushing into the seat. Lunging up, Becca was trapped by the seat belt for a moment, snapping back into her spot. Fumbling to unclick, she twisted in her seat before freeing herself and practically falling to the ground, burying her face into Miss Hannah's snatch.

The fit woman smelled of blueberries, an aroma that only made Becca hotter for some reason. Reaching into her tights, she pulled her SLUT panties to the side and buried a finger, deep in her slit. Pleasuring Miss Hannah made this hot in and of its own, the finger in her pussy just made it better.

The car door suddenly opened, Miss Hannah pushing Becca back and getting out of the car. Still playing with her pussy, Becca fell back, the toy in her ass reminding her of its existence. Briefly remiss, Becca pulls herself together, quickly getting up and following Miss Hannah out the door.

The July heat was intense at that point of the day. The two women made for a blue trail marker and started up the path. They maneuvered silently, Becca making sure to keep just a few steps behind Miss Hannah. Staring at the ass in her face, her boss's skirt fluttered in the breeze, occasionally exposing her flawless butt and giving a glimpse of her pussy lips. Becca longed to reach forward, perhaps touch her skin and give it a squeeze, maybe even fondle her flesh gently in her hands. Becca dreamt of how soft the touch might be.

They continued to hike in silence, the sounds of nature a refreshing change from the sounds of the city. The singing of the birds a pleasant reprieve from the angry sounds of her neighborhood. Approaching a clearing, Becca got her first glimpse of the city on the horizon. Breathtaking, she thought to herself, in awe of the beautiful skyline before her. She took a deep breath, grateful for the experience, her eyes catching a sign indicating that the scenic view was just ahead.

Finally, at the half way point of their hike, they reached the full view of the city. Skyscrapers decorated their view, smaller buildings surrounding the medium buildings around it. Becca and Miss Hannah stood there, admiring the sight ahead of them. Miss Hannah reached for Becca's hand and took hold, squeezing it tight for a solid three count.

"Thank you for sharing this with me," Becca's boss warmly pined to her, releasing the squeeze. "My husband doesn't care much for the outdoors, but he's a good man from good money."

Becca looked to Miss Hannah, smiling and showing an appreciation for the personal information she felt comfortable to share. Letting go of her hand, Becca hugged the woman next to her, sharing the special moment.

"Enough," Miss Hannah snapped, making Becca think she may have overstepped. "Take off your clothes, down to the SLUT thong."

Hearing her, but giving a second look, Becca hesitated just a moment too long.

"NOW!" her boss yelled, the mood suddenly changing. Reaching in to her bag, Miss Hannah pulled out a golden chained leash, with a leather collar at the end, and threw it on the ground.

"Put it on Slut."

Taking off her top first, Becca exposed her tanned breasts to the natural sunshine for the first time. Virgin tits, she thought to herself, basking in the freedom this place provided. After using a tanning bed for years, she enjoyed the feeling of the natural sun on her tits. Continuing to undress quickly, she pulled down her leggings, struggling to pull the pants over her shoes. She sat down on the ground, pulling off one leg before tugging off the other, her SLUT thong glaring back at Miss Hannah.

Standing back up, Becca took the collar and latched it around her neck, picking up the leash handle, taking a knee before presenting it to Miss Hannah. Grabbing hold of the leash, Miss Hannah started back on the trail, giving it a tug and telling Becca to keep up. The sunshine warming their skin as they abandoned Becca's clothes at scenic overlook.

"Ahead of me now," Miss Hannah instructed, not utilizing the leash just yet.

Becca hustled to get ahead, making sure to keep pace a few steps in front of Miss Hannah. Continuing on the trail, they hiked silently, Becca naked and leading the way. Suddenly, up ahead, movement caught her eye. Two hikers were on their way up the trail, seemingly unaware of the naked leashed woman hiking down atop them. Miss Hannah gave a tug on the leash, making Becca pause in her place, her tits jiggling briefly. They waited silently.

"Well shit, if it isn't Miss Hannah," one of the men proclaimed, seeing the woman walking a leashed person in front. "Thanks again for letting us mount your beautiful trails here. Say there, who you got here Miss Hannah?"

"This is Slut," she answered back, seemingly knowing the men she was speaking with. Becca stood there and moved slightly to cover modesty, Miss Hannah giving a quick tug on the leash to make her stop in her tracks. Dropping her hands to her side, she looked away.

Catching a hint of shame in Becca, Miss Hannah pushed forward. "Introduce yourself honey."

"Hello, my name is Slut," Becca stated, matter of factly. Still not making eye contact with the men.

"Hi Slut," the first man responded. "I'm Derek. This is my friend Austin. I feel like you may be missing something about the property."

"I am new to the property," she responded, Miss Hannah giving the leash a gentle tug of approval. "We're here to mount this beautiful trail as well. Would you please tell me the right way?"

"Well, you see," Derek smiled. "This is a free use property and anyone naked is actually available for fun."

"Oh, I see," Becca responded, looking back at Miss Hannah, being greeted with a knowing smile and shrug of the shoulders.

"My ass is plugged. But otherwise, please use me freely."

This was all the encouragement the two men needed. Approaching Becca as they undressed, she stood there with her hands by her sides, the leash tethering her to Miss Hannah nearby. Derek and Austin started caressing Becca's body, touching her all over and squeezing her bits from time to time. Austin was the first to reach inside of her SLUT thong, laughing out loud at the ease that his finger slid in.

"Oh man dude, she is wet," he proclaimed. Becca stood there as they touched her beneath the hot afternoon sun. She started breathing heavier, aroused by the attention these two men provided.

"She's hot for it," Derek added, being the first to take out his dick from his pants. Rubbing his growing member in his hand, it quickly grew to a solid six inches. Becca wrapped her hand around it, taking over with a jerking motion and happy that she could grab it completely in her hand. Optimistic it wouldn't stretch her open too much, she shifted her body and guided it towards her hot, dripping opening. Feeling extra full between this cock and the toy in her ass, Becca started eagerly rocking her hips back. Standing in place and fucking back on Derek, Miss Hannah gave a tug on the leash to remind Becca that she was still there.

Being pulled back against Derek, Austin saw his opportunity to approach Becca and start sucking on her nipples. The sharp as tack appendages were needy of attention, attention that Austin was all too willing to provide. He slapped Becca's left breast before pinching her other nipple in his hand.

"Welcome to the property slut, maybe we'll see you again sometime."

Completing his wicked burn, Austin grabbed Becca's head and pulled it down, jamming his cock into Becca's mouth and cumming immediately. Swallowing his load as fast as she could, she couldn't even taste the cum as it passed right through her throat and into her stomach. Whipping her hair back, she caused her leash to fly through the air for a moment. Remaining still, Becca gazed out the corner of her eye to see Miss Hannah playing with herself while she watched the show. Disappointed at not tasting the cum, but satisfied at a job well done, Becca cleaned the remaining juices from his cock, eager to show this immature man the time of his life.

Watching the show in front of him, Derek jammed his cock deep into Becca, lifting her up on to her toes briefly. Reaching her arm back, she grabbed his neck and pulled him towards her, kissing him on the lips and darting her tongue into his mouth. She felt his dick pulsing inside of her, first one and then two shots of hot cum priming the walls of her insides. Counting the third and fourth shots filling her up, she started cumming on Derek's dick while he tried to hold her up. Kicking her legs out, she balanced on his cock, savoring the release as it washed over her, feeling the warmth on her skin from the brightly shining sun.

As she finished pulsing, her naked body fell to the ground, enjoying the feeling of the grass beneath her skin. Suddenly remembering her leash, she gave it a tug to find the other end still unattended. Hopping up, she grabbed for the handle while searching for Miss Hannah. Finding her sitting over in the shade, Becca brought her the leash, taking a knee and presenting it to her once again.

Playing with herself, Miss Hannah looked at Becca, a single glob of Austin's cum still lingering on her cheek. The image was too much, causing Miss Hannah to erupt in an orgasm, her pussy squirting out juices all over the space in front of her. Seeing her pussy pulsing, Becca dove down between her legs and started lapping up her leaking liquid, drinking in the taste of the boss that brought her these newest experiences. Still enjoying the show, the two men began to straighten up, watching the women as they gathered their gear.

Being decent again, Austin and Derek gave a wave and continued up the trail, aiming to visit the same scenic peak that the two ladies had just come from.

Miss Hannah, standing and now feeling relieved a bit, picked up the leash from the ground, giving it a sharp tug. Becca stumbled briefly, before sliding over and taking a knee next to Miss Hannah. With a quick pat of Becca's head, Miss Hannah began down the trail again, leading her cum covered slut behind her now. Trying to catch up at first, Miss Hannah shot Becca a look that told her stay back a bit.

Continuing down the trail, Miss Hannah gave a tug from time to time, reminding Becca that she was still the one in charge. Becca basked in the freedom of hiking nude, feeling safe and provided for in a world that had eaten her up and spit her out. She felt her skin starting to grow moist, her skin becoming slightly shiny from her cooling sweat. The two carried on a bit, before arriving at a clearing where a picnic table was set up and apparently, waiting for them. There was a lunch spread on the table, looking delicious to the starving Becca who had already burned countless calories that hike.

"Anything I can do for you before lunch?" Becca longingly asked Miss Hannah, still eyeing the feast on the table.

"There is actually," Miss Hannah responded. "Since it's so nice out here, I'd like you to take some pictures of yourself with this phone. I think I want to share you with my husband, Mr. Noah."

The thought of this made Becca exponentially hotter. After dreaming of fucking her boss Kevin and his pregnant fiancée Justine, here was a woman offering up herself AND her husband to Becca. Knowing this was her opportunity to make a statement, Becca decided to pull out all the stops.

Taking the phone from Miss Hannah, she squatted over it, her tender, well-fucked pussy becoming the first close up shot. Pulling the phone up, she lifted it up above her head next, taking one picture aiming at her pretty, well-fucked face, before scooping up the glob of cum from her cheek and taking another with her fingered covered.

Picture four was her jamming that cum covered finger in her mouth, the fifth a clean finger and her smiling face.

Without realizing it, all of the pictures had featured the leash. As an idea for one more, she grabbed the chain with one hand and pulled it up, choking herself slightly. She tugged on it a few times to make sure it appeared tight as could be, wrapping the leash around her hand a few times. Sticking out her tongue while choking herself with the leash, she took a selfie capturing the depraved expression on her face. Looking at the picture and noticing another glob of cum on her ear, she decided she was satisfied with the outcome. Approaching Miss Hannah again and dropping to her knees, she extended the phone to her once again masturbating boss.

"Finished Slut?" she asked while toying away.

"I think so Miss Hannah," Becca replied. "Unless I can do more?"

"Well actually," she paused, eyeing the pretty slut before her. "Vincent, our driver? He thinks you're very sexy."

"Thank you, Miss Hannah. I'd be happy to help him for you, if you'd like."

"Would you let him fuck your pussy?" she asked Becca, becoming aroused at the conversation.

"My pussy is yours Miss Hannah," she replied. "I'll do as you wish."

"You'll fucking eat my pussy right now then," Miss Hannah instructed, grabbing the willing Becca by the hair and pulling her down to her hot fucking lips. Never could she have imagined finding someone so committed to this lifestyle, Miss Hannah thought.

"And he can't have your pussy Slut, don't worry, we don't give that to the help. Just suck him off as fast as you can, but not until I say. Now sit there and cross your legs."

"I will," Becca responded, sitting down nearly naked on the ground beside Miss Hannah, patiently awaiting whatever, or whomever, came next. She rocked herself a little, the toy in her ass still filling her up while her SLUT thong filled with another hiker's cum.

The two waited in that position, Miss Hannah enjoying some lunch in her outfit, occasionally feeding a piece of cheese or pepperoni, to her petite Slut. Suddenly, from the road just beyond the trees, their ride pulled up to the picnic, the man Becca knew as Vincent getting out to greet them. Briefly shielding his eyes from the sun with his hand, he quickly noticed the naked woman attached to his boss with a leash. Knowing he may be in for a treat, a bulge started forming in his pants.

Becca crawled forward, the man slowing as she approached him and reached for his buckle. Without a word, he recognized the situation for what it was and let her pull out his dick. Packing a surprising amount of heat, Vincent the driver unloaded a cock that was identical to the 12 incher Miss Hannah had in her briefcase.

The things rich people buy, she thought to herself.

Stopping before him on her knees, he laid his shaft on her face, his massive member stretching from chin to hair as it blocked the sun briefly from her eye. Becca giggled to herself as she felt his balls tighten on her chin, this wouldn't take long at all, she thought to herself. He waved it up and down a few more times, slapping it gently on her face and savoring the hot, greedy slut waiting for his seed.

She licked her lips obediently, waiting for the green light to suck this man's cock.

"Go," Miss Hannah called out, playing with her clit at the table while she took a sip from her wine. She loved watching this raunchy behavior, easily worth the measly $5000 that her new slut requested, not that money had come up again yet.