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Bella & The Boss Pt. 1 - Bella's First Time [CNC] [M20s/F20s/F20s] [Rough]
Author Summary
No-Sink6382 is in Rough
Post Body

TW: There are a few confronting scenes in this story, based on a fantasy shared with me by a female reader of my past work.

Isabella knocked on my office door, poking her head inside. I glanced up and waved her in.

She hurried over to my desk, a manilla folder clutched in front of her, a look of excitement on her face.

“Samantha Jones just left, she's signed all the consent forms and filmed her waiver.”

I took the folder from her and flicked through its contents. Her requests were pretty basic, but gave us a lot of creative freedom for the experience.

These were my favorites, I was going to have a lot of fun.

There was a photo of Samantha in the front of the folder. She was smiling, but looked very nervous. She was in her late twenties, a stunning brunette with bright green eyes underlined by a streak of freckles.

Her top button was undone, showing off the cleavage of her double D's.

I'd seen her last week during her initial consultation, where my cock had throbbed thinking about what she was in for. It was throbbing again now.

Isabella was still looking excited, like she had something she couldn't wait to tell me.

I looked at her, raising an eyebrow.

“Go on.”

“Boss, Samantha wants me to be there too!” She could barely contain her excitement.

I stroked my beard, thinking.

Isabella was stunning, with her Colombian heritage shining through in everything from her looks to her personality. I knew she had her heart set on this, but I'd only hired her for administration work.

“Bella, you know how I feel about you coming along on jobs. We have a great vibe in here, but out there it's… different. It just doesn't feel right exposing you to that.”

“Boss, I'm 23. Are you really worried about exposing me to it, or are you just worried about me seeing how fucked up you really are?” She gave me a cheeky grin, but I couldn't deny the truth in her words.

I was worried about her seeing how fucked up I was, I really liked Bella.

But, I was only 5 years older than her.

“Okay, fine, but you’re on probation. It'll just be the two of us on the day, but get Ben out on surveillance. I want to know all of Samantha's movements, along with her husband's.”

“Yes Boss.” Bella gave me a big grin, before turning and walking out of my office. I watched her ass as she left, her Colombian genetics stretching the ass of her American made pants.

I took the USB drive from the folder and plugged it into my laptop, clicking the only video file on there.

It started, Samantha's nervous face on the screen, kneeling in front of the camera before she began to speak:

“I, Samantha Jones, hand over ultimate consent to the Company for a period of 30 days from the date of this recording. I understand that I can be taken and used at any point, and it is my wish that I be used like the nasty whore that I am. I have chosen “Shane”, as my safe word, as this is my husband's name. Although I doubt I'll need it.”

I grinned with excitement, my cock growing hard in my jeans.

***

2 Weeks Later

When somebody signs up for an experience, we almost never take them in the first week. It's best to stick to surveillance only.

See, they're on alert for the first week, expecting something to happen every time they turn a corner or open a door.

I like to let them settle in a bit, get back to the monotony of their day to day lives, almost forgetting what they signed up for.

The excitement never fully leaves, because I knew Samantha was at her office desk right now, wondering: “Will it be today? Will it even happen? What will they do to me? How will I feel?”

This tension, this unknown will have her getting wet at the sight of every scary looking guy, every car driving slowly by, every bump in the night.

The waiting, not knowing is just as important as the experience itself.

But today was the day to put a plan in motion.

Bella was standing next to me at my desk, her pants and blouse stretched tight in the right places, braided hazelnut hair reaching halfway down her back.

Her perfume was sweet, mixed with the smell of her sweat from the summer heat. She was smiling up at me, her dark eyes and full lips distracting me from the discussion we were having about Ben's surveillance.

“Sorry Bella, what was that?”

“I said; every Monday, Wednesday and Friday night she goes to yoga, then a gym session and dinner with her gym buddy. All we need to do is grab her one of those days, send a text to her gym buddy to cancel, then she's all ours for four hours.”

“Damn Bella, four hours! What do you have in mind for this poor woman?” I laughed.

“I want to make sure she gets her money's worth.” She gave me a cheeky grin.

At that moment, I knew that Bella was just as twisted as me.

I was really looking forward to this.

“Alright, Friday it is. Sam's going to need the weekend to recover.”

Bella let out a squeal of excitement, before looking up at me and asking: “What are we going to do to her?”

I just smiled and put my hand on her shoulder.

“You'll see Bella, you'll see.”

***

Friday

Today was the day, Sam was about to have her darkest, most repressed fantasies become reality.

I was standing with Bella and Ben at the back of our blacked out Ford Transit, pointing at a quiet street on the Maps app on my iPad.

“We'll grab her here, between 6 and 6:15PM. Bella, you'll grab her phone and cancel on her friend. Ben, you'll drop us at the warehouse and wait outside. Clear?”

“Clear.” Ben nodded.

“Clear, Boss.” Bella smiled. We loaded up, Ben in the driver's seat, Bella and I shoulder to shoulder on the floor in the back.

All the vans' seats had been pulled out. Sometimes the job called for the extra space.

Ben slowed the van to a stop. “We're here.”

I glanced at my watch: 5:37PM.

“Alright Bella, mask up. I'm going to wait in that alley opposite. When Sam passes the back of the van, throw open the door and stand in her way. I'll do the rest.”

She grinned at me. “Thanks for letting me come, I promise I won't mess it up.”

I gave her back a rub. “I know you won't.”

Then I walked across the sidewalk and waited in the narrow alley.

***

6:03PM

Show time.

Sam was walking toward us, a gym bag slung over her shoulder, just 15 seconds away. I looked at the van door, slightly ajar and could see Bella crouched in position.

I waited until Sam was level with the back tail light and Bella was halfway out the door before I made my move. Taking three long strides, I made it just as Sam came to a stop in front of Bella, confusion on her face.

I used my momentum, grabbing Sam by both arms, lifting and twisting her in the air, pinning her face down on the floor of the van, with my knee in her back.

Bella followed, slamming the door closed before handing me two zip ties.

I pulled Sam's hands behind her back, zip tying them together. She had started to kick and yell, so Bella tied a gag in her mouth.

I knelt down harder on her back, leaning down to her ear and hissing: “Shut the fuck up, bitch.”

She groaned against the gag, still kicking.

Bella grabbed a fistful of her hair, lifting Sam's head off the van floor and giving her a stinging slap.

“He said; shut the fuck up, bitch.” She slapped her again, before slipping a blackout hood over her head, then giving me a cheeky grin.

We pulled our own masks off, enjoying the cool air-conditioning.

Sam lay on the van floor, silent but shaking from the adrenaline rushing through her body.

I knew from past clients what she was thinking: “Is this real? Is this what I signed up for? What are they going to do to me?”

She was scared, excited and most of all; more aroused than she could ever remember being.

***

Ben backed the van into the warehouse, Bella flung the door open and I pulled Sam to her feet by her arm, dragging her out of the van.

The warehouse had a hallway running down the center, a large bedroom and ensuite bathroom at the far end, along with two large rooms, one either side of the hallway.

I frog marched Sam down the hallway, dragging her into the room on the right. It had vinyl plank flooring and bright fluorescent lighting, an entire wall dedicated to all kinds of toys; whips, dildos, vibrators, strap ons, restraints and more.

There was a couch on the opposite wall and a fridge in the corner. This could be thirsty work, after all.

My cock throbbed, swelling in anticipation.

I glanced behind me and saw Bella's expression turn to amazement. She'd never been here before and I could tell she was excited by the toy wall.

In the middle of the room stood a carpenter's saw horse. I grabbed a coil of rope from the wall, before bending Sam over the saw horse and tying her to it by her waist, hands still zip tied behind her back.

I ran my hand over her ass, up her back and down her arm, before squeezing her bicep hard. Leaning over, I whispered in her ear: “You could scream for days here before anyone heard you, do you understand?”

She nodded.

I removed the gag, making sure to keep the hood in place. She sucked in several breaths of fresh air, before asking: “Is this it? Is it happening?”

I grabbed her throat, squeezing it.

“What the fuck are you talking about?”

I felt her try to swallow, before answering with a choked breath: “Nothing.”

l relaxed my grip.

“Your friend thinks you canceled on her. Your husband thinks you're at the gym. Nobody even knows you're gone, let alone where. You're ours for a while, so we're going to have some fun.”

I walked over to Bella, lightly grabbing her arm, pulling her back out the door. I whispered in her ear: “I know this is your first time, so don't feel any pressure, you can just watch if you like.”

I smelt her sweet perfume mixed with her sweat again.

“If you think I'm letting you have this pretty, prissy suburban bitch all to yourself, you're sadly mistaken.”

Her warm breath made my skin tingle. I glanced down into her eyes and was met by a look of defiance, nervousness and arousal.

She felt she needed to prove herself to me, to gain my approval.

“Well, let's do it then.”

I let go of her arm and took off my shirt, followed by my jeans, now standing in front of Bella in nothing but my boxers.

I caught her looking me up and down, a short inhale and a bite of her bottom lip giving her away.

I looked at her. “Have you gone shy now?”

She smiled back at me, before stripping down herself.

She stood in front of me, wearing nothing but red lingerie, perfectly contrasted against her caramel skin.

I could see the outline of her areolas through her bra and a landing strip through her panties.

It was her turn to catch me out, but she was staring at my cock as it swelled, pushing against my boxers.

She looked up at me, raising an eyebrow. “No wonder we have so many happy customers.”

I laughed. “Let's go make one more.”

***

Sam was wearing her gym gear; a blue crop top and matching yoga pants. I don't know who invented yoga pants, but they deserve a Nobel prize. Her ass and thighs were stretching them to their limit, built by several years of heavy gym work.

I grabbed them by the waistband, ripping them down to her knees with her panties, before reaching around and freeing her gorgeous tits from her top.

She let out a small shriek, surprised at suddenly being exposed, completely naked and helpless.

Bella wound up and landed a loud smack on Sam's ass cheek, instantly leaving a red hand print.

She shrieked again, louder, with a tinge of arousal. Her breathing quickened, coming in short, sharp pants.

“Oh, fuck,” she muttered under her breath.

I knelt down in front of her, squeezing her throat. I reached out and pinched her nipple, teasing it erect.

“I get the feeling you're a real nasty little whore, aren't you?” I asked.

She exhaled, hard. “Yes.”

I slapped her across the cheek. “What are you?”

“A nasty little whore,” she whispered.

Bella delivered another loud slap on Sam's other ass cheek. “Do you know what nasty little whores get?”

Sam squealed. “What do they get?”

Bella grinned. “Well, they get fucked like nasty little whores.”

She slapped Sam's ass again and was rewarded with another squeal.

“Do you know how nasty little whores get fucked?” I asked, tightening my grip on her throat. “No,” she choked.

I answered by standing up and dropping my boxers, my cock springing forward.

Sam couldn't see, but Bella could and she was mesmerized. At 9 inches long with the girth to match, I'd always known I was gifted, but Bella's open-mouthed stare was definitely confirmation.

I lifted the edge of Sam's hood, lifting her head by a fistful of hair and pressed the head of my cock to her lips.

“Open up, slut.”

She obeyed, opening her mouth as wide as she could. I pushed the head of my cock into her mouth, feeling her tongue press against the underside of my shaft, guiding me in.

Placing a hand under her chin to lock her head in place, I thrust forward, feeling her mouth and throat tighten in protest when I hit her gag reflex. I pulled back, watching her cough and gag, saliva running down her chin onto the floor.

I thrust my cock down her throat again, further this time before I felt her gag, cough and splutter. With a fistful of her hair and my hand gripping her chin, she couldn't turn away as I plunged my throbbing cock down her throat again and again, deeper and deeper.

She was drooling down her chin and over my balls, glistening strings of saliva pooling on the floor as she gagged and coughed, her cheeks turning bright pink with the effort and struggle for oxygen.

Looking up, I saw Bella staring, mesmerized. She had a look of awe and lust on her face, biting her bottom lip while she watched me face fuck Sam. Noticing me watching, she looked up and blushed.

I grinned and nodded toward the toy wall. She understood. I watched her rub her fingers up and down Sam's wet slit, spreading her wetness and teasing her clit.

Bella slipped two fingers inside Sam's soaking cunt, making her moan against my cock. She curled her fingers downward, pumping them in and out against Sam's G-spot. The muffled moans against my cock continued, between the coughs and gagging.

Bella stopped, walked over to the toy wall and selected a magic wand, a tube of lube and a strap-on dildo that rivaled the size of my own cock.

She crouched between Sam's legs, strapping the magic wand to the leg of the saw horse, pressed it hard against her clit and cranked it to full power. Sam's hips tried to buck in response, but she was tied down tight.

Instead, her whole body began to quiver and she gasped, before I slid my cock back down her throat, my saliva soaked balls coming to rest against her chin. She gagged, but I kept it there and pinched her nostrils closed.

I felt her gagging and struggling to breathe. I enjoyed the sensation for a good few moments before pulling my cock back out, watching her suck in lungfuls of air, still coughing.

“Fuck…” was all she could gasp between breaths.

I watched Bella, now wearing the strap on, lubing it up and standing behind Sam.

She looked sexy, but powerful.

I didn't expect what came next.

Bella lined up behind Sam, slapped her ass and pushed the head of the strap-on straight into her tight little asshole.

Sam wailed in surprise and pain. I doubted she'd ever had anything that big rammed into her ass without warning.

In fact, I doubted she'd had anything that big up her ass at all.

Bella doubled down, gripping Sam's hips and driving the massive dildo further into her tight little ass. I watched on, shocked, wondering if Sam could take it.

She was wailing, obviously in discomfort, but she didn't say anything, just lay there as Bella stretched her asshole wider than it had ever been.

With one final thrust, the base of the dildo came to rest against Sam's now dripping cunt, all nine inches buried firmly up her tight prissy, suburban ass.

Bella looked at me with smug satisfaction, landing another stinging blow across Sam's ass. She began sliding out of her, before ramming all the way back home, making Sam squeal.

“Now that,” Bella grinned, “is how nasty little whores should be fucked.”

***

With Bella ramming her ass, the wand on her clit and me face fucking her senseless, Sam's body was electrified. She was shaking, quivering, moaning and grunting in sheer sexual ecstasy.

I knew it wouldn't be long before she was over the edge, and Bella knew it too. We matched our rhythms and picked up the pace, pounding her senseless from both ends.

I looked down at her, the veins in her neck bulging. I wrapped my hand around them and squeezed. “Is the nasty little slut going to cum for us?”

I slapped her across the cheek. “Cum for us, you dirty fucking whore.”

Bella slapped her ass. “What would your husband think, seeing us pound your whore fuck holes? Cum for us, you filthy fucking slut.”

This sent Sam over the edge, her body shaking and spasming, I rammed my cock the whole way down her throat, pinching her nostrils closed again, feeling her scream in ecstasy against my cock.

Her orgasm rocked her body, intensified by the lack of oxygen. Every muscle fiber lit up, her hips desperately fighting her restraints as wave after wave of sexual electricity rocked through her body.

I heard splashing on the floor and realized she was squirting, soaking herself, her yoga pants and Bella's panties.

Bella had a look of pure lust on her face, Sam's squirting only serving to turn Bella on even more, pounding her asshole even harder.

Bella looked at me. “Can you believe this slut? One mention of her husband seeing her like this and the filthy whore is squirting everywhere.”

I laughed, locking eyes with Bella, my rock hard cock still rammed down Sam's throat. “I know, what a nasty slut.”

I could tell Sam was really getting off on being humiliated, so I decided to turn it up a notch. “I think we need to punish her, she's made a mess.”

Bella's eyes lit up and she grinned at me, stepping backward, the strap on making a satisfying ‘pop’ as it left Sam's asshole.

I pulled my cock from her throat and watched as she desperately sucked in lungfuls of air. She panted out: “Oh… my… fucking… god…” A smile spread across her face.

I untied her from the saw horse and pulled her upright by the arm, her hands still tied behind her back. “Don't look too happy bitch, you've made a mess.”

I kicked the back of her legs and she fell to her knees in the puddle she'd squirted. I grabbed a fistful of her hair and bent her over, her face an inch from the ground.

“Clean it up.”

She stuck her tongue out slowly, searching for the puddle.

She found it and tasted her own juices. She let out a small hum, and I knew she liked the taste.

Bella and I sat on the couch together and watched Sam as she lapped up the aftermath of her own orgasm from the floor, still unable to see a thing, her pants around her knees, her tits hanging out of her top. She was obviously enjoying the taste and the humiliation.

Bella's shoulder and leg were pressed against mine. Her skin felt incredible against me, she'd worked up a sweat and it was glistening all over her body, accentuating every curve, every line, every crease and crevice.

It was running down her neck, collecting on her chest and dripping between her gorgeous tits. I glanced lower, watching it trail down her abs and pool in her navel. I'd never realised just how fucking perfect Bella's body was.

Then again, I'd never seen her in lingerie, soaked in sweat.

I watched her squirm, rubbing her thighs together. She was watching Sam intently, getting more and more aroused.

I stood up, walked over to Sam and pulled her to her knees by her hair. “You made a mess of my friend, too.”

Dragging her to the couch, she awkwardly shuffled on her knees to keep up.

Bella looked up at me, a questioning look on her face until I grabbed her knee, opening her legs. She got the message and shuffled forward on the couch, her soaking panties right in front of Sam's face.

I pushed her face into Bella's panties and felt a tinge of jealousy, before stepping back to lean on the saw horse and watch.

Sam eagerly got to work, licking the inside of Bella's thighs clean, before moving on to sucking her own juices from Bella's panties.

I watched Bella's face as she bit her bottom lip, eyes half closed, watching the hooded Sam lap up her own juices. She grabbed the back of Sam's head, grinding her hot, wet mound into her face.

She eagerly pulled her panties aside, now pushing her soaking cunt into Sam's face. “Eat it, slut.”

Sam obeyed immediately by flicking her tongue out, circling Bella's beautiful pussy. I was definitely jealous now.

She kissed, licked and flicked her tongue around, teasing Bella, who now was teasing her nipples through her bra, her breaths coming shorter and sharper.

At that moment, my watch alarm sounded.

Our time was up, we had to finish.

Bella looked at me, obviously disappointed, but pushed Sam back on to her haunches.

I took my seat next to Bella on the couch again.

“As much fun as we've been having, that alarm means the experience is now over, Sam. Your husband will be expecting you home soon and we don't want to raise the alarm. I'm going to take your hood off now, okay?”

She sighed.”Yeah, okay.”

I removed the hood and she squinted, blinking for a few seconds to get used to the light.

Her face was a mess, her eyes were bloodshot, mascara running down her cheeks, saliva all over her chin, along with her own juices.

She looked up at us, a huge grin spreading across her face. “Oh my god, you guys are fucking incredible, that was everything I hoped it would be! It felt so real.”

I reached out and gave her a light slap on the cheek. “Thank you, we aim to please. Let's get you cleaned up, we have a driver waiting to take you home.”

***

Sam had showered and changed into the fresh set of clothes from her gym bag and was now on her way home with Ben. By the sound of it, she'd had the night of her life.

I walked back to the room to clean up, but found Bella still sitting on the couch, staring at the floor.

“What's up Bella?”

She looked up at me, a smile on her face. “That was so fucking hot, I loved every minute.”

I laughed. “You were great, you really surprised me.”

She blushed, looking a little ashamed. “Guess you're not the only fucked up one, huh?”

I took her hand, pulling her to her feet. “Let's get washed up and chat about it over a beer, alright?”

Bella took first shower, but didn't have a change of clothes so ended up in a pair of my boxers and an AC/DC T-shirt.

I came out of the ensuite wearing just a fresh set of boxers. I figured she'd already seen me naked, so it'd be fine.

Bella was sitting against the headboard of the bed, her feet tucked underneath her. She was sipping at a Corona, the rest of the six-pack on the bed in front of her.

I sat opposite her, cross legged and grabbed a beer for myself.

“So, your first job. How'd it feel?”

She looked at me, took a mouthful of her beer and considered it.

“I was really into it, maybe too much. What does it say about me if I enjoy degrading and humiliating someone like that?” She looked genuinely concerned.

“Well the fact that you're worried about it says a lot. Remember, she approached us and asked for this. Would you do that to someone who didn’t want it?”

She looked down, smiling. “No way, I'd only do it to someone who wanted it. You're right, she did ask for it. Still, if that's what gets me off, it's kind of fucked up, right?”

Her eyes locked on to mine, searching.

“Bella, all kinds of things can get us off in the moment. It doesn't mean you're fucked up. Even if it does, we can be fucked up together.”

I gave her a cheeky grin.

She grinned back at me and I saw her shoulders relax. “‘Fucked up together’, I'll take that Boss.”

“Besides, I'm sure ass fucking prissy suburban bitches isn't the only thing that gets you off?”

She looked down at her beer, fiddling with the label. “Actually…” she trailed off.

“What is it, Bella?”

She drained the rest of her beer.

“Well, the hottest part of it all was watching you. I didn't realize how big you were. Plus, I've kinda had a crush on you since you first interviewed me.”

She kept her head down, but cast her eyes upward, searching my face, waiting for an answer. I watched her chest rise and fall faster in anticipation.

I lifted my beer, finishing it off and putting it to the side.

I knelt up, on to my knees, her gorgeous eyes following me.

I leant forward, placing my index finger under her chin, tilting her head to face mine.

She knelt up, bringing her face within inches. I placed my hand on her cheek, closing the last couple of inches to press my lips to hers.

They were the softest lips I'd ever felt, pressing back eagerly against me. She opened her mouth and I felt her warm breath against my lips, before I opened mine too. Our tongues met, gently exploring each other.

I grabbed her hips, pulling our bodies together. I placed my hand on the back of her neck as our tongues pushed further, passionately embracing each other. I felt her hands exploring my back, pulling me closer.

I pulled back, gazing into her gorgeous eyes for a moment. Lust overtook me, I leaned forward and kissed her neck, her supple skin making my cock throb in my boxers, straining against them.

I reached down, grabbing her shirt and pulling it over her head.

I stopped, taking in the sight of her perfect body. Her petite collarbones, her beautiful breasts accentuated by her caramel areolas and hard nipples, the tiny trail of peach fuzz running from her sternum to her belly button, then down to the top of her boxers, where I knew it met her landing strip.

I grabbed the back of her thighs, pulling her legs forward and sliding her on to her back. Leaning down, I planted a passionate kiss on her neck, followed by another, slightly further down. I kissed my way down her neck and across her collar bones.

Every kiss was met with a small gasp from Bella, her hands holding my head, combing through my hair. “You're so fucking sexy.”

I laughed into her chest, working my way down her breasts, kissing in tighter and tighter circles around her nipples, tracing my tongue around her areolas.

Want a part 2? Let me know in the comments!

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