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What A Wicked Smile

Author: bestie
last update Huling Na-update: 2025-07-30 02:10:47

I took the opportunity to text Cass, to see how the hotel work was going. No answer. I guess she was busy. About five minutes later, when I walked back with a new hose, I finally got a message. I regret opening it in public. I had to hide in an alley to let my immediate erection subside. It was an upskirt photo of Cass in a black maid's uniform. No, it was not one of those ridiculous uniforms from p**n, it was a regular work one. But Cass had lifted the skirt up a bit, revealing the bottom of her ass. Though not really, because where her ass was, was also the text "Anyone in need of a maid?" and a sad emoji.

I texted back some very complimentary words for her.

Later when I got back home, both Cass and I were beaten, so we watched some shit Kevin Costner movie, more or less sleeping through the rest of the evening.

For Sunday I had gotten some tickets to a boxing event from Bran, as thanks for the repairs I did. I guess the repairs were much needed. Neither of us really cared for combat sports, but we figured why not. We were doing so much other stuff these days, so why not try something new, even if it wasn't due to any kinks?

Turns out, Bran was not only handing out tickets. He was fighting on the undercard of said event. And it was no small event. The sports center held at least five thousand seats, it looked like. Though, as I said. We knew nothing about the sport. Bran knocked some guy out fast, and the other matches were half-exciting as well.

"Yeah, let's never do that again," Cass laughed as we drove home.

"What, Bran was just being nice giving us tickets? Though, I kinda agree. Not for me."

"He wasn't so nice with the other guy," Cass joked.

When Monday came around, I wasn't ready for the week. We had barely relaxed all weekend, and yet here I was back in the office busting my balls over mundane paperwork. Cass had more assignments at the University, so she was also pretty busy. The spring semester was wrapping up, and so assignments and exams were coming down the pipeline in rapid succession.

Tuesday was Monday copy-paste more or less. The only upside was that we both were diligent enough so that we got home in time to get a good night's sleep, which we hadn't gotten much of lately. Hitting the hay early was a rare luxury.

So having the extra time, we lay in bed talking about our future. We always wanted kids, and me having a steady job, and her masters going so well, now probably was the time. Perhaps as soon as after the wedding, even.

And talking of the wedding.

"I want the night to be special. Our wedding night," Cassandra said. I perked up at that.

"So. I know we're not exactly the wait-until-married type. But perhaps we could make the wait a little more special, in some other way," Cass continued. "What if you were a condom up until our wedding night?"

"What? Why? It's two and a half months away" I asked, hating condoms as most people did. "You're on the pill?"

"To make it special, I told you. The reason is two-fold. One, we've talked about family. You have a job, and my masters is going great. So maybe I want to get off the pill one of these days, you know? But I want to conceive on our honeymoon. I think that would make it extra special," Cass said.

"And the second?" I asked. I was kind of on board already. It was sort of romantic how she put it. We had planned our honeymoon trip to Europe, so all of the romantic elements that entailed certainly added to the thought of making it all special. And I truly wanted it to be special.

"Well. I know denial is sort of a thing you're having," Cassandra said. "Imagine how pent-up you'd be! You would probably knock me up on your first try!"

"Oooh. Well. I can't lie, not loving the idea of condoms, but hey. I'll do it for you. And you're making a lot of sense. It's a nice suggestion," I said, trying to keep it light-hearted.

"It's not a suggestion. You're not getting any of this without a condom!" Cass said, looking me in the eyes with a crooked, wicked smile.

God. She knew. She was such a naughty girl.

*

Wednesday we woke up fully rested for a change. Throughout the workday, Cass kept sending me teasing photos. Sometimes captioned, sometimes not. Ever more daring, though mostly in the comfort of our home. Her hot body made her posing game seem easy. And Cass kept teasing me about the condoms even. I didn't know if that was something she was going to do, but she certainly didn't mind teasing me about not being able to hit her raw for the next two months.

So to say, when I saw Cassandra coming down the corridor through the small window in my office door, I was pretty excited to see her. As she entered my office, I immediately took in the outfit she had been teasing me with for the last few hours. Blue jeans that her thighs and ass filled out nicely, a white crop top, and a loosely fitted zipped-up hoodie.

"Hey there! How's your day been?"

"Better now that you're here. Damn, Cass, that last photo you sent was so fucking delicious, jesus christ. Looking at you now in those tight jeans, even... Fuck I wish I could go home and take you right now."

Cass giggled. Her last photo was her prone in bed with nothing but jeans on, the same she wore now, captioned with "Guess who's not hitting any of this raw! That's you." And I couldn't even do anything about it, as I was at work.

"Oh, you—"

Cass was interrupted by a bang and an unreasonably loud vacuum cleaner roaring behind me. Neil seemed to have come earlier than usual to clean my office. I wonder why.

Cass then looked at me with another wicked smile. What was she up to now?

Neil started stumbling around the office, vacuuming half-heartedly around. He glanced at Cass a few times. After a few minutes of ear torture, Neil shut the thing off. Cass then jumped up and went over to the bin.

"I'll get that for you, sweetie," Cass said with her kindest voice.

Cass slowly bent over at the waist. Her light blue jeans stretched firmly against her firm, muscled ass, hugging those wide-hipped thighs stretching up to her shapely ass. Neil's eyes went wide as he openly looked at how magnificent her ass filled out in those jeans. He even tried to hide adjusting his cock, probably struggling with keeping it down at the awesome display of Cassandra's hot booty.

Cass picked up the bin, slowly rose up, squishing and flexing her ass nicely in the process, and turned with a small jerk in her hips, like she was showing off. She smiled widely as she saw the reactions from both Neil and myself.

"Here you go, big boy," Cass said in an almost sensual way.

"Thanks, miss... ma'am. You're too kind," Neil stuttered. Then a sly smile crossed his fat lips. "And thanks for handing me the bin."

The nerves on that guy!

Neil took the bin and emptied it in the trash on his cart, and hurried out. I couldn't help but notice that he was sporting an obvious tent as he was hurrying out, lazily trying to hide it behind the cart.

"Yep, you definitely got a fan," I laughed as the door closed. Cass smiled widely. "Can you believe he just thanked you?"

"Fuck... Now I'm all turned up!" Cass complained.

 

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    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

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    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

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    "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

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    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

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    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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