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Up To Something

Author: bestie
last update Last Updated: 2025-07-30 02:45:13

"Guess who I ran into today at work?" Cass asked, pausing the show we were watching that evening.

"Who? Someone from work?" I joked.

"Silly you. No, Neil showed up. I don't know if he knew I worked at that hotel, he looked kinda surprised."

My first thoughts immediately went to -

"Did something happen?" I asked, turning towards her. Cass giggled at my reaction.

"Don't worry, I was a good girl. Though it was very tempting."

"Tempting?"

"Yeah. It's so hot going around being such a naughty little girl. Submitting to him like that, it's getting to me," Cass teased.

"That is why I think it's hot, didn't know you were this into it too," I said.

"I'm as surprised as you are. Acting like this... in such a taboo way is such a huge turn-on, I can't help it. And you are into it as much as you are, so going around almost behind your back is such a thrill. Not that I would ever actually go behind your back, we both know that. I guess I share the fantasy. And your trust in me is just out of this world, to let me do all that. To have so much fun."

"Fuck yeah. Seeing this side of you is so... adventurous. And you're getting pretty creative with it too. Like both doing it in the car and in my own office bathroom? Jesus Christ."

Cass smiled at that.

"I don't know why he was there, though. At the hotel. We just exchanged looks and a nod, then I was off to do my duties," she said.

"Well. I guess he does things outside of work," I said.

"Yeah, anyway, I was just telling you because I wanna be open with you. Like you've been saying, trust is important. And especially with the kinks we're out exploring."

I nodded in agreement.

"Also, he's really good with his tongue, so it was really tempting," Cass teased, gave me a peck, then turned the series back on. I shook my head and turned my attention back towards the TV.

The next day was Sunday, which meant work at the food pantry for me. I was met by a small cheer by the volunteers. Apparently more shit had broken down, and I had become the designated repairman apparently.

"Just call me when it happens. Don't let it pile up," I said cheerfully. The crew nodded.

Monday it was back to work. I was getting bunched with loads of paperwork for this huge report. It was a true bitch, but important for some client or some bullshit. I didn't really know. I had gotten this job from connections through my dad. I just needed to keep my head down, do the work and move up to an even more cushy job where I could enjoy life, I guess.

At least that was the master plan.

In reality, sitting in an office had never been an aspiration of mine, and it wasn't all that motivating to have that as a plan for the foreseeable future. Perhaps that was why I involved myself way more with other stuff. And with the charity work. And fishing. Kinks. And everything that was not this boring, but well-paid job.

And it kept a roof over me and Cass' head, which was much needed while she was still studying. Speaking of Cass. It was finally lunch. This was the only day of the week she'd be able to see me lately.

I looked over at her as she handed me my lunch salad. I guess I was kind of lucky she was even here. Cass was usually the one who brought what we ate, so we often ended up eating pretty healthy, her being a former athlete. Cass truly was a light in a gruesome Monday, even if the lunch was only shared for this single day.

As always, she looked splendid. Dressed in light blue tight-as-hell jeans, and a loose-fitting green crop top. She looked both sporty and hot, but still maintained a lot of decency.

However, our moment of appreciation was short-lived. The vacuum alerted us to Neil's arrival. Though, it was certainly different this time around.

Cass seemed slightly flustered, as if she was blushing, as she exchanged a look with Neil. He even was so bold as to raise his eyebrows expectantly. Did he really proposition my future wife right in front of me? I guess in his mind I was clueless to the... situation. Fuck, the boldness of this bastard.

I looked at Cass again. She was now lightly biting her lip, shifting in her seat. Was really this crass, gross nuclear waste of a janitor turning Cass on with his mere presence? I couldn't help but feel a bit jealous at her physical reaction to him being in the room. I also couldn't help but become turned on by it. Intimated even.

Despite being flustered, Cass had a devious smile. She smiled at me and nodded towards the big window facing the parking lot. I looked at it. Cass nodded.

"What?" I mouthed.

"Get distracted," Cass mouthed back. She was up to something.

I slowly got up and headed over to the window, standing so that I could see Cass from the corner of my eye. Wondering what she was up to. Neil was out of view, but he seemed to have paused his vacuuming a bit. Maybe to see what Cass was up to too.

I heard the chair getting pushed back as Cass stood. I could see her walk around the bin and bend over. Her back was towards me so I got a magnificent view of her tight jeans stretched around her firm ass. Neil got that view too, though much closer. He had moved a bit closer to her, with his back towards me, giving me the opportunity to look a bit better. Though I snapped my head away as Neil quickly checked on me. He moved his body so that he somewhat obscured my view a bit more.

Through the roaring vacuuming, I could hear a muffled slap, as Neil lightly slapped her ass with his pudgy hand. I turned my head in time to see Neil's hand descend another time. Neil then moved his hand up and from the way his elbows rose and lowered again, it seemed to slide his hand down her pants! Fuck, he was pretty bold. Getting pretty comfortable with how to treat Cass. Even here in the room with me just there. Fucking hell.

 

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  • The Secret Pleasures Of Cassandra   I Need That Big Dick In My Life:>Ep16

    It was unbelievable.However, all good things have to come to an end."Get down!" Neil yelled, sliding himself out of Cass's sopping wet pussy.Cass did as she was told. Neil yanked the condom off and immediately shot waves of cum across her face, neck, and cleavage. Even if it was his third round, fourth if you count the first blow job, he was still cumming a whole lot. Though this time not for as long as the last time. Cass' head jolted back from the sudden impact and got her whole face covered regardless."Fffuuuuuck," Neil gasped with jagged breath, barely able to get a single intelligible sound out.He stood shaking over her for minutes after, feeling the bliss of having ravaged this hot cute girl three times in one afternoon. How lucky wasn't Neil, eh? He glanced down at her, seeing his cum spread across her cute face."Those black cheeks and cute brown lips look so hot covered in my cum, I almost wanna go again," Neil said."Heh, I think you've had enough, mister!" Cass laughed

  • The Secret Pleasures Of Cassandra   I Need That Big Dick In My Life:>Ep15

    He was frenching her lips as soon as he connected. He just couldn't get enough of her hot sex, her cute disposition, and her overall body. Neil roughly shoved her pants down over her ankles, never letting up licking her sweet pussy. Soon he had Cass clutching the car seat around her, panting wildly and bucking herself into his mouth as she came all over his face."Well, you certainly put on a great argument," Cass said, still slightly out of breath from cumming so fast."Gimme that phone of yours, I'll prop it on the dash," Neil said.Fuck it, it had already happened, so why not again? Cass reached for her purse, fished out her phone, and gave it to Neil.While he was propping the phone, Cass dove back to Neil's pant pockets and fished out another condom, rolled it on Neil, and jerked him while he was getting situated. When the phone was all good to go, he grabbed his cock and put it at her opening, but as he was about to push, Cass spoke up."No, fuck me from behind instead," Cass pl

  • The Secret Pleasures Of Cassandra   I Need That Big Dick In My Life:>Ep14

    My poor office chair was squeaking as Cass rode Neil with vigor, not holding back. Her athletic background made her pretty agile, so she had no trouble holding her balance, even if it felt like the chair would keel over at any moment. That didn't deter Cass, who frantically slammed her big juicy ass on Neil's dick. She was pretty strong too, so each time Neil's cock ripped into her like a punch. A wonderful, forceful punch.Neil let her do the work, enjoying the feeling of her tight pussy rolling over his cock over and over again. In the meantime, he slid his hands back to her ass again, mauling those glorious cheeks. They felt so soft, yet firm in his hands. Like the muscles were solid, but her skin was like silk. Neil couldn't get enough of her ass, and they both knew it. Even while fucking her, he wanted to shove his tongue up her ass.Instead, he pressed at her cheeks, clutching her tightly against him. She had to shift her feet so that she instead sat on her knees. This shift in

  • The Secret Pleasures Of Cassandra   I Need That Big Dick In My Life:>Ep13

    "Whose pussy is this now?" Neil shoved through his gritted teeth."Wh- shut up... just give it to me! Fuck! Shit!" Cass pressed out through a guttural jagged groan, not really paying attention to all that crap. She was way too busy getting fucked."Who owns this pussy, heh?!" Neil demanded, slowing his thrusts."Fuck, who do you think?!" Cass replied, annoyed by the interruption, trying to press back against Neil."Say it, bitch!" Neil said, pressing hard up against her cervix, tickling her inner portions. She was not yet accustomed getting hit this deep, and certainly not while getting stretched so much."YOURS!" Cass shouted. "It's your pussy!"She silently thanked God that the vacuum was roaring now. Cass was bound to submit to Neil, but she had no idea how such dirty talk would affect her dear Isaac. Fuck, Neil was fucking her so good she had all but forgotten about him up till now.But with the disguise of an empty office, and with the roaring vacuum, Neil could fuck Cass as hard

  • The Secret Pleasures Of Cassandra   I Need That Big Dick In My Life:>Ep12

    Neil looked down at her muscled ass, aiming his thick cock at her entrance. He had waited so long for this and being this close to conquering Cass sweet pussy was almost enough to make him dizzy where he stood. Neil rested his tip against her opening, letting her feel his thickness. She didn't seem to object this time around as she had before. Perhaps he had finally brought her around.Finally.Neil pressed forward.Cass quickly realized that it was not his finger. Neil was currently entering her with his huge dick, stretching her wider than she had ever felt before. Looking back it was surreal to see that big dick being lodged inside of her own body."FUUUCK!!!" Cass gasped out loud. "That is.. FUCKING... God. You're so big!"Her mind was completely filled with the sensation of finally getting Neil inside her. Both her mind and the shape of her insides felt like they were getting reshaped. It was like her past experiences with sex were getting erased and replaced with this new sensat

  • The Secret Pleasures Of Cassandra   I Need That Big Dick In My Life:>Ep11

    Cass felt his tongue slide slowly into her folds and after a couple of minutes of tender soft licking, Neil picked up the pace. Really digging into her with everything he got. The office was soon filled with the sounds of Neil lapping away at her pussy. The desk was even creaking with each lap he gave her.Cass couldn't help but clutch the desk. It was pure ecstasy getting her pussy licked while bent over her own husband's desk, in his own office. While he was sitting just down the hall in a cubicle. Or perhaps he had moved closer.All thoughts of her fiancé quickly disappeared as something that had been building for a while was now ripping through her with full force. Her second orgasm of the night, the first in the office. The anticipation and the delightful pleasure Neil gave her made her squeal out. Cass tried to shut it, but the release of the pent-up tension was too much for her.Finally a proper orgasm.Not an embellished one.Not one ruined by a condom.A true, wrecking orga-

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