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Destinee Holland
Destinee Holland

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Session 𝓞ne-Hundred-One

Session 101:

“The Set Timeline”

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There was this familiar tension in the air as we walked together toward her bedroom.

She walked in front of me, guiding me, rather than walking by my side.

I knew it meant our dynamics had shifted.

She holds the power here.

I missed this feeling.

The warm knots that tickled my lower stomach as I got undressed beside the bed.

I didn’t realize how much I craved them until I felt them again.

It's incredible.

I didn’t bother peeking at what Monroe was grabbing from the closet.

I wanted to be clueless.

It would make this moment even more tense for me.

And Monroe will drip all the built-up tension right back out of me.  

I couldn’t tell if I was trembling from being cold and naked or out of pure excitement.

Monroe held a variety of things in her hands upon exiting the closet.

I noticed the dildo first.

Then a couple of leather black straps, I think?

And a gag—I was pretty sure it was a gag.

“Open your pretty mouth for me,” I heard her softly murmur, carefully setting the different items down on the end of the bed.

I didn’t hesitate to part my lips for her, staring up at her beautiful face.

It was indeed a gag just as I predicted.

Monroe secured the rubber ball between my parted lips, forcing my mouth to open wider.

Then she tied it at the back of my head, almost purposely tight.

Or it felt purposeful.

She looked calm, taking her time to secure the gag.

She even caressed the sides of my arms for a moment, openly eyeing my naked body.

Then she grabbed one of the leather straps.

Or I thought it was a leather strap.

It was a collar instead?

I realized after she wrapped the cold material around my neck, making me mumble incoherently.

I wasn’t sure what to say—I just had the urge to say something.

Mostly, because this was really fucking degrading.

Especially when she secured the leash onto the collar wrapped around my tanned neck.

I felt like a fucking pet.

The gag in my mouth didn’t help.

I couldn’t stop drooling.

And to think it couldn’t get worse—

“On your hands and knees, Liberty.”

I looked at her for a second.

I mean, really looked at her.

Because this was insane.

It’s insane, right?

Wrong.

At least with how Monroe was looking at me.

She was patient.

And I couldn’t tell if that was a good or bad thing.

Is she adding onto this punishment the longer I take?

I suddenly lowered down before I could think it through, shaking my head as I kneeled before her and pressed my hands to the cold floor.

“Is there something you’d like to say, Liberty?” Monroe asked, noticing that I was shaking my head.

So I shook my head again, not wanting to make the situation worse.

But this felt pretty fucking close to the worst outcome.

“Lovely,” she murmured, taking a step forward.

I was confused about where she was going.

Then I was lightly tugged forward, and then I realized.

She’s walking me… like a pet.

I clenched my jaw, crawling beside her as she walked at a calm pace around the room.

I didn’t say a word.

I just focused on breathing and trying not to drool too much with the fucking rubber ball in my mouth.

I’ve never felt so fucking degraded in my life before, which says a lot given I kissed her fucking heels before.

And it wasn’t just one lap around the room—Monroe kept going.

She kept walking me, humming softly to herself as her slippers pattered against the shiny floors.

She was fully dressed in the black bodysuit and those dark jeans from earlier.

Meanwhile, I was fully naked, drooling, and being walked around the bedroom like her pet.

My knees began to hurt.

And the cold floor pressed sharply into my palms after a while.

I didn’t want to complain or say something that might worsen the punishment.

I wanted to take this, especially since the reward would satisfy me for weeks to come.

I just needed to behave.

I tried to contain my whimpers after endless minutes of being walked around the room, crawling weakly for her.

My unconscious whines and whimpers seemed to satisfy Monroe.

I could tell by the subtle tilt of her soft lips.

I swear it had been thirty minutes by now.

Probably longer.

Monroe doesn’t seem bored in the slightest.

I squeezed my eyes shut, trying to lose track of the time as I continued slowly crawling on my hands and knees.

I’m not sure how much more time passed by—I completely lost track.

By the time Monroe stopped beside me, my knees felt bruised, and my hands were as cold as ice.

But I did it.

I felt really proud that I did it, especially with the look of approval Monroe had on her face.

She looked satisfied.

That’s what mattered to me.

My thighs were sore, and it was a little hard to walk, but it was all completely worth it to me.

Especially as Monroe stood with me in the bathroom, gently cupping my face as she carefully wiped the drool from my chin and around my mouth.

She looked at me in a way that made me feel so fucking warm inside.

I never wanted her stare to drift away from me.

But eventually it did.

Only to meet my dark eyes again through the mirror.

Monroe had positioned herself behind me, eyeing me through the bathroom mirror.

She openly admired the black leather collar still wrapped around my neck, gently caressing my shoulders.

“I’ll be back, darling,” she softly whispered in my ear.

Then she pulled away from me, leaving me to stare at myself in the mirror.

The gag was no longer in my mouth, and the drool was gone, so I was a little more relaxed.

Not fully, though, especially as I wondered what Monroe walked off to grab.

It turned out to be the dildo I noticed in her hand almost an hour ago.

The sight of her with it was enough to make me press my thighs together.

That’s when I processed the wetness gathered at my core, dampening my inner thighs.

I didn’t realize being walked by a leash on my hands and knees would actually turn me on… but here we are.

Maybe it’s that Monroe did it.

She can do anything, and somehow, I’m dripping wet for her.

“Spread your legs for me,” Monroe said, stopping directly behind me.

I slid my foot further away from the other almost immediately.

But it only earned a dissatisfied look from my girlfriend behind me.

A gasp echoed from my lips when she used her foot to slide one of mine further away from the other.

She slid my foot so far that I grabbed the sink in front of me for stability.

“Monroe,” I breathed out when she pressed me down against the sink.

“Wrong name, darling,” she corrected, tangling her fingers in my hair and—

I whimpered when she lifted my head away from the sink, forcing me to meet my own stare in the mirror.

Then I felt it.

The pressure skimming my wet folds, teasing me in a way that made me squirm.

A moan vibrated in my chest the moment she pressed the toy past my folds, dipping it inside of me.

I felt so tight around it and—

“Fuck,” I breathed out, “Monroe,” I whined when she pressed it deeper.

A choked moan spilled from my lips when she purposely angled it against my spot.

“I'm sorry,” I quickly forced out, realizing that’s probably what she wanted all along.

Monroe hummed softly, “There’s my good girl,” she praised as I stared into my glossy eyes in the mirror.

“Oh my god,” I forced out when she went faster and faster.

It completely contrasted how she touched me earlier.

This was the roughest she’s ever been.

And somehow I liked it.

It made me wetter.

Dripping, actually.

All the way down my inner thighs, I was dripping purely for her.

My body couldn’t get enough.

I arched and squirmed every time she thrusted deeper or went harder, and Monroe held me in place by my hair through it all.

I couldn’t even keep eye contact with myself in the mirror after a few more strokes.

My eyes rolled to the back of my head whether I could help it or not.

And then it hit me.

My orgasm.

It was chaotic, and it stole my fucking breath.

I couldn’t breathe.

It felt like there wasn’t enough air to at least.

I’m not sure.

Everything was hazy.

That’s how fucking intense it all was.

I fully crumbled against the sink, my body going limp as she kept sliding into me over and over again.

So much so that it made my body rock back and forth, uncontrollable moans spilling from my lips as she sent me up to a second orgasm.

It was pure fucking pleasure, and all I could do was lie there and let her give it all to me.

 But by the time I came down from my second orgasm, that was it.

I couldn’t take another.

“Monroe-Monroe,” I rushed out, reaching around me to steady myself.

Glass soap containers clattered as I tried to grab the cold sink faucet for some type of stability.

“You can take a third one, Liberty,” I heard her say, angling further against my spot and earning the deepest whimper from me. “I’ve trained you better than to give out now.”

I mumbled incoherently, unable to even string proper words together.

All I could get out was her name repeatedly as I rapidly approached my peak.

My face felt wet too.

That’s when I registered that I was crying or that my legs felt almost numb from how tingly they were.  

She tricked me.

This was the real punishment right here.

My body twisted to the side the moment my orgasm hit me like a pound of fucking bricks.

I gasped and wheezed for air, crying between each moan that she drew from me.

And then suddenly—

I felt her slide the toy out of me.

And her grip fell away from my hair.

Then I was just lying there—completely naked and bent over the sink.

My body was buzzing with this incredible warmth, one that I could only lie there and bask in.

I kept my eyes closed—even as Monroe gently unhooked the collar around my neck and guided me away from the sink.

“Sleep,” I mumbled as she lifted me entirely into her arms.

“We’ll sleep, darling,” Monroe whispered, softly kissing my forehead as I leaned against her chest with my eyes still closed

Eventually, I could feel her lay me down in the soft bed, pulling the covers over me before her footsteps pattered away from me.

I just relaxed entirely, not even worried about where she’s going or what she’s doing.

She ended up coming back countless minutes later with pasta.

I could smell it.

It smelled incredible.

And she even fed me a few bites as I lay there with my eyes closed, ready to fall asleep.

Monroe had propped my head up so it was hard to fully drift off.

But once she grabbed a toothbrush and a cup of water to brush my teeth, I was ready to knock out.

After I was settled, Monroe left me to go shower, and I flipped on my side to go to sleep.

I’m not sure what happened after that.

I remember feeling her soft, naked body slide under the covers behind me, pulling me flush against her.

Then the next thing I knew, I was waking up to the sound of a phone ringing.

I thought it was an alarm at first, but then I heard Monroe say hello.

It was enough to drift me away from my sleep, wondering who she could be on the phone with.

“We can’t make it to breakfast,” was all I heard my girlfriend say.

Then it was a few silent moments, making me grow even more curious.

So much so that I peeked my eyes open.

Yes, I’m nosy.

“No, we—”

My girlfriend suddenly cut herself short.

Then a scoff fell from her lips.

“What happened?” I asked before I could help it, turning around against her soft body to face her.

Monroe shook her head. “We apparently have breakfast with my parents,” she said, her jaw noticeably tight as she leaned down—

And softly kissed my lips.

“Good morning,” she whispered, making me smile slightly.

“We’ll make it a good morning,” I assured her, leaning in to kiss her lips again.

Monroe hummed softly, kissing me even deeper.

“If you can walk properly,” she subtly murmured against my lips, making me chuckle.

“I probably can’t,” I admitted as she gently grabbed my neck, pulling me in even closer.

“I know you can’t,” Monroe added, making me chuckle again, especially when she started placing repetitive kisses on my lips.

“Ro,” I whispered, smiling even wider.

“I’m obsessed with you,” she said, her lips twitching up slightly, “Quite literally.”

All I could do was smile like a fucking idiot, letting her kiss my lips over and over again until she was satisfied.

God, she was the cutest.

I hate that her parents just randomly pushed breakfast on her like this.

She weirdly seemed fine with it.

Even while we were getting ready.

She picked out our outfits and ran our shower.

We washed each other and even did each other's hair and makeup.

It was a really nice morning.

Then we got in the car...

And Monroe went silent.

She let me talk fully, not even bothering to grab my hand to hold or place her hand on my thigh.

I gave her all the space she wanted, though.

If she wanted physical touch, she would grab me.

I know how tedious she is, and I never want to make her discomfort worse.

So I slowly went silent, letting her have some quietness to sift through the confines of her mind.

I also didn’t open my door once we made it to the restaurant.

I sat there with her until she was ready to open her door and get out of the car.

We sat there for a few moments, not in an uncomfortable silence, but a mutual one instead.

I waited for her.

Always.

Because I get her, and I want her to always feel that.

“They have something up their sleeves,” Monroe finally spoke, her voice so much more rigid compared to earlier.

I probably hadn’t heard her talk for the entirety of thirty minutes.

“Whatever it is, we’ll work through it, baby,” I assured her. “We’re a team. I got you. You know this.”

Monroe nodded a few times, “A team,” she whispered almost to herself, her brows furrowed.

I extended my hand out to her, still not touching her. “A team,” I repeated again.

Monroe’s blue eyes drifted down to my open hand, remaining silent for a moment.

A really long moment.

But I was patient.

I waited countless seconds until she finally lifted her hand and put it in mine.

“I get you,” I whispered, bringing our tangled hands to my lips, “Never forget that,” I added softly, gently kissing the back of her hand.

Monroe’s chest visibly sank as she let out a deep sigh, nodding a few times.

“Okay,” was all she said, rolling her tense shoulders back.

I could tell she was still in her head, but it was nice to know my words made a slight difference for her.

Especially since she made the first move to step out of the car, her shiny black stilettos clicking against the pavement.

She wore her usual black dress pants and a matching blouse, keeping her hair in a low bun with her bangs framing her face.

 She also picked out my outfit to match hers, so I wore all black too.

I had on one of her silky button-down shirts for once with a cute black skirt that hit my mid-thighs.

I wore short kitten heels, and my bun was slicked into a high bun, curls framing my face.

I felt very… business casual.

Sort of, since the skirt should be longer to consider it that.

But it was nice.

It gave me a glimpse into how I would dress after college.

I would officially be at my big girl job, experiencing adulthood.

I let out a deep sigh as soon as we walked into the elegant restaurant.

Chandeliers sparkled, the chatter was respectfully low, and the fancy carpets looked like they were from France.

I glanced around as we passed a couple of round white-clothed tables, lingering with noticeably wealthy people.

I honestly didn’t know this restaurant existed here, and I knew nearly every inch of Seattle.

Just not the wealthy parts, obviously.

This kind of wealth was a fuck-you-money kind of rich.

And Leon and Clarisse Leclair fit right fucking in.

Clarisse wore white, her clothing logo-less, but still cost no less than a brand new Mercedes.

Her wrist was lined with two elegant diamond bracelets, and her neck glistening with a matching teardrop necklace.

Pale blonde waves spread past her shoulders, precisely tucked behind her ears.

Leon was in his usual button-down shirt and dress pants beside her, his bald head reflecting the chandelier lighting.

I hope being bald isn’t a choice for him.

I hope he was forced to be bald.

I don’t know why, but that’s some kind of karma.

“Monroe,” Leon addressed his daughter first with his usual narcissistic grin, “Ms. Fierro,” he said, glancing at me.

I didn’t force a smile.

I didn’t even nod.

I just sat down in the chair Monroe pulled out for me, allowing her to push me closer to the table.

Then she silently sat down next to me, still not bothering to say a single word to her parents.

It was definitely… awkward.

“This is a decent restaurant, oui?” Clarisse spoke through the awkwardness, bringing the delicate china tea cup to her lips.

I feel like they’re oblivious to the fucking awkwardness here.

Or they just choose to ignore it because I guess they have that option too.

“Decent,” Leon agreed, grabbing one of the menus, “We’ll see if the food has potential.”

I blinked blankly at them.

I couldn’t help it.

This place looked freshly out of one of those fancy architecture magazines.

The kind of restaurant you’d see inside The Ritz or something.

What the fuck is wrong with them?

“Potential is a great topic,” Leon suddenly spoke again, opening his menu even if his dark beady eyes drifted to his daughter. “We should discuss your potential, Monroe.”

My girlfriend didn’t respond.

But I couldn’t help but draw in a deep breath, wondering what they were about to fucking say.

It’s never predictable with them.

“This summer,” Leon determined, lowering the tall menu away from his face. “We’re making the transition. You’re taking over Levane.”  

My face fell—really fucking fast.

I couldn’t help it.  

Monroe even looked displaced by his words.

They weren’t a threat this time.

No.

They were a promise.

Monroe is taking over Levane come fucking summer.

Can he do that?

Of course, he can.

There’s too much on the line to fight back.

And there’s no dragging it out anymore.

Now there’s a set timeline.

That’s it.

So much for our current plan.

I’m not even sure what new plan we could formulate at this point.

Leon has too much power.

If he wants Monroe to take over Levane come summer, then she’ll be forced to.

Everyone at this table knows that.

This changes everything.

Session 𝓞ne-Hundred-One

Comments

BRO WHAT THE PET THING IS CRAZY

.

When Liberty said she hopes that Leon being bald was forced on him, I cackled 🤣🤣🤣🤣🤣

ShadsNM


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