Cassandra's Adventures Pt. 01

Authors note:

This is the start of a small cuckold / hotwife I want to try out. I wrote this just to dip my toe in this category. If you don't like this type of story, please don't read any further. I have plenty of other stuff both published and coming along, and this is likely a rare occasion where I write within this particular fetish.

Also, huge thanks to Grandeman and Violett for all the help provided. Both gave tremendous feedback and held my hand through it all.

*

I met my fiancée back in my first year of college. I was originally dating someone else, but when that went to shit, Cassandra was there to comfort me. And boy did she comfort me. We sat next to each other at the library, and when she saw how distraught I was one morning she reached out to me. She was kind and gentle, letting me air out to her.

I didn't really know Cass, but I can't lie. I had noticed her before. Even when I was dating the other girl I sometimes caught myself staring at Cassandra. And when she reached out to me after my breakup, something about her made me trust her. Something I had not regretted ever since.

Me? I'm Isaac. I was raised in a pretty conservative white family. Not a deep-fried south kind of conservatism, but I certainly was a bit on the nervous side when I brought a black girl home. But Cassandra won them all over, and soon she was part of the family like she always was meant to be.

Cassandra Rose was truly an amazing woman. I have no idea how I scored such a gorgeous thing, but yet I was a lucky bastard. She had light brown skin, being African-American, and beautiful hazel eyes which always creased so cutely whenever she smiled. And that smile of hers... When she smiled it always reached her eyes, and her whole face lit up like a beacon in a dark tunnel. Though, I was in no dark tunnel. I was dating this woman, so I was on cloud nine!

And in addition to having a cute, delightful face, her body was killer too. Cassandra, often Cass for short, was a former gymnast and rightfully so she had the body that came with it. Muscled, toned, and athletic. Amazing in an orange thong. Or any thong, for that matter. She still did gymnastics multiple times a week, but not on an Olympic scale like she did when she was younger.

Her sunny disposition in life made everyone who met her like her. How could you not? And yet, I was the one who had scored this hot-bodied, genuinely nice person.

When we both finalized our BAs, I popped the question. I knew Cass was the one. So after a few years of dating, and another two years as fiancées, we finally got around to start planning the wedding, and perhaps even starting a family down the line. For the time being, Cass did her masters in bioengineering while I just got myself a cushy management job with a secluded office, and settled in. My job allowed us to rent a small house in the suburbs, a nice beginner house until we were able to buy something proper.

In addition, we were no strangers to pulling up our sleeves. We both liked the outdoors and living an active lifestyle that kept us both in decent shape, though Cass was way fitter than me being a former athlete. Cass had a job at a hotel where she worked one weekend a month, and also volunteered at a local food pantry and a soup kitchen.

Our relationship was great. Truly great. Cassandra evolved into becoming my best friend, as well as my romantic partner. In the beginning, we made love as often as possible. We still did but had slowed down with the wedding coming up, and with me having a job, Cass in the spring semester of her degree, and such.

Plus, Cass wasn't the most sexual person. It's not that she doesn't enjoy sex, and I definitely enjoy sex with her. But to her it was like an extension of cuddling, always wanting to be able to have eye contact, to be face to face. Which was great, don't get me wrong. That's just how it is, and I love it.

All that would change.

*

Cassandra and I were sitting one day eating our lunch at my office, talking about the wedding, her next lecture, and other stuff. She had surprised me by visiting me. A pleasant surprise of course. We shared lunch from time to time, but it had been a minute since the last time.

"Ehm, Isaac. Who the fuck is that?" Cassandra asked. I turned and looked.

In the small window in my office door, I saw the coarse face of our newest janitor, Neil. He had just begun as a janitor on our floor. He was a large, thoroughly annoying dude. Neil had this annoying tendency where he always insisted on doing the offices when it was at its busiest. Though today, it seemed like he wanted to interrupt my lunch break.

I often shared my lunch break at my office with my soon-to-be wife, Cassandra, who studied a small drive away. She would stop by somewhere and get our lunch and head down to my office so we could share some extra time together. She also usually picked me up, working this close to each other allowed some carpooling.

"Oh, that? That's Neil, the new janitor. Don't mind him. He can be kind of a creep, just ignore him," I chuckled. Cassandra rolled her eyes.

It looked like Neil had been standing there for more than a minute, his broad face startled as we looked over at him. Being caught, Neil didn't pretend anymore and entered the room.

Neil was a large man. Not tall, but wide. Blonde. He sort of had that look of a guy who was handsome in high school, maybe even in college, but then had a nuclear meltdown ever since. Blonde mop on his head, stubbled. Broad shoulders, but extremely out of shape.

"'Scuse me, guys, I'm just gonna—" Neil started and started up the loudest vacuum cleaner ever, drowning down any attempts of conversation.

Might as well, we were discussing plans for our upcoming wedding, and this annoying idiot didn't really need to hear any of that. Instead, we sat awkwardly looking at each other, eyebrows raised, eating each our lunch.

Neil was moving his unfit body around the office, vacuuming the carpet, yanking the bin, and making a lot of unnecessary noise. I looked over at him annoyed, hoping he took the hint.

Neil didn't meet my eyes. Instead, while he had made his way back to the door he was openly staring at Cassandra's ass. Right in front of me! The balls on this fucking guy.

But at the same time... I couldn't help but feel a small tingling sensation. A small adrenaline rush. Slowly I realized that seeing this greasy large dude ogling my beautiful, kind girlfriend excited me. Cassandra was way out of this guy's league. Perhaps that was why he wasn't hiding his stare all that well, he knew he had no chance with a girl like her. He might've already eaten the inevitable rejection and did not care as much of the social consequences of being a staring creep.

Neil hadn't seen me catching him yet. I saw his beady eyes trace Cassandra's sexy body, dressed in tight khaki pants and a light green button-up shirt hiding her perky, full breasts. Her ass truly hugged those pants firmly. Hell, no wonder he was staring. Cassandra was hot just sitting there.

Neil started to move up close to Cassandra, feigning getting the bin, but it was clear as day he tried to get a whiff of her scent. Neil lingered for a few moments, tying the bag, then leaned up, his eyes fixed on her strong thighs. His white forehead shone with sweat.

Then Cassandra turned her head, looking up at him standing beside her. That startled Neil enough to rush the rest of the cleaning, pack his shit and fuck off.

Cassandra turned back to me, mouthing, "What the fuck?"

She had obviously caught him staring. We continued talking about the wedding only 3 months away, ignoring all of that awkward shit.

Later that day, when she picked me up outside the office, I decided, who knows why, to push the subject.

"You had an admirer today," I said, grinning at Cassandra. Cassandra shrugged.

"What can I say? I'm hot as shit," Cassandra said nonchalantly. I chuckled.

"You're not wrong. Those khakis really hug that nice ass of yours good," I told her. Compliments weren't hard to come by when it came to Cass. She was just the best.

"Maybe I'll strike a pose next time," Cass joked, looking over at me. I gulped. I had no idea she would push it like this. Not that she really did, to her it was all fun and games, but deep inside me I actually found the thought... arousing.

"Is this because of that porn you're watching?" Cassandra asked casually. My heart stopped. Oh no. Not this.

"Erh what... what do you mean?" I wasn't even sure what she had found. I watch a lot of porn. A lot. Cassandra knew this, but she had never asked about it. She sort of let it be a me-thing.

"You have that folder. With the captions with the wives and the thing and the thing?" Cass said, waving her hand impatiently. "I'm not mad, just wondered if it had something to do with all that."

"I don't know... Maybe."

We sat in a small silence for a few moments. Cass truly didn't seem mad at all, she just hummed along with the song on the radio, signaling when she made her left turn, nothing out of the ordinary. Man, she was just so accepting.

We pulled into our driveway, and I immediately got out to get her car. Best be on my best behavior, you know. Cass giggled at my eagerness.

So I didn't really push it any further, and neither did she. Her curiosity seemed to be satisfied, not really being one to talk all that much about these types of things. No matter. We started dinner, went for a jog, and enjoyed the rest of the day.

It wasn't until later in the evening when we were getting ready for bed that Cassandra decided to broach the subject again. We stood brushing out teeth and Cass was deep in thought, glancing over at me. Reluctantly, she started.

"So. I know how I'm not so adventurous when it comes to... sex. No, don't correct me. I know what's up, and frankly, it would be more disingenuous to not recognize it. I'll let you say your peace, but hear me out."

I tried chiming in, but Cassandra wasn't having it. She barged ahead.

"I thought... Maybe we could open up a bit. You know, as a prelude to our marriage. And I was thinking... those captions you like so much... why don't I do some?"

Cass gauged my reaction, but I didn't say anything. Now I definitely wanted to see where this was going. I wasn't sure if the nature of those captions were something I wanted to explore.

Not getting any response, Cass went on.

"What if I send you photos? Some posing and some captions to go along with? Wouldn't that be hot? Something new? I don't know how lewd I will be, but hey, some cute pics of your girl can't be that bad, right?"

A non-rhetorical question. This was my cue.

"Absolutely. I would love photos from you, babe. Fuck yeah... that's a great idea."

Cassandra smiled at my reaction and we wrapped up our bed prep.

"Why don't you go ahead?" Cassandra said seductively. I damn near ran out the door.

While laying in bed waiting for Cass in the bathroom, I got the anticipated text message from none other than Cassandra. I opened it.

It was a picture. A picture of Cassandra in her flannel pajama pants and one of my flannel shirts. She stood perking her lips, holding up a peace sign. It was captioned "Hi from the bathroom!"

It wasn't particularly 'hot', but it certainly displayed her cute innocence. My heart fluttered at how proud I was of my girl's whole disposition. She was just so good-natured. I looked at her smile shining up at me from the screen, her smile reaching all the way to her beautiful hazel eyes. Even if it wasn't revealing, her looks were still something to be admired.

"Hey, at least she's trying," I thought. I genuinely was happy for her, that she tried to explore her own limits. But I wanted to push her a bit.

"You can do better than that," I laughed through the door. No reply.

Another picture.

Cassandra had buttoned up the shirt, showing her firm stomach with a hint of abs. She was clutching the shirt so that only parts of her boobs were showing, but it was just enough to make it seriously hot and teasing. Wow! She held her nice perky c-cup tits through the shirt, while biting her lower lip, smiling coyly. Wow! And the caption topped it off.

"Get ready for me big boy."

By the time I read it, Cassandra had come out from the bathroom, still shirtless, lustily looking at my erection. She immediately jumped into bed and climbed on top of me. She never was a huge fan of being on top, but now Cass couldn't be stopped. She was too riled up and had to get fucked right the fuck now.

Cass threw her pants off, revealing her sexy, firm hips and her incredible, athletic ass, and inserted my cock into her. I groaned out loud, Cass moaning satisfyingly. Cass was so tight, so warm, I couldn't help it.

"Man, these pictures get you going," I panted.

"Hell yeah, that last one... oh god," Cass moaned, grinding firmly against me, whimpering into my chest. "It was so hot!"

"You liked the attention today, huh? Then taking naughty pictures for your fiancée?" I pushed. Cass moved her hand to my mouth, shutting me up.

"Don't talk like that. Fuckk... ff— fuuuuck." Cass was moaning loudly as she came hard on my cock, sending me right over the edge with her. I grunted and groaned as my cock shot deep into her. Fuck she's so warm and so good.

She rolled off of me.

"I'm gonna send you some pictures, that's for sure," she groaned. We shared a laugh before dozing off to sleep.

*

The next day, I was still in awe of Cass' reaction to the pictures. I wasn't too sure if she had been so receptive to the 'showing off' in front of Neil, but with how pleased she was, all that sort of became second nature. But I couldn't help but wonder what a guy like Neil would've thought if he had seen that last picture.

Cass had some meetings at some other part of town, so she wasn't able to meet me for lunch. Someone who did show up, however, was Neil.

He stood in the door, looking around the office. The bastard was looking for Cass!

"Where's the wife?" Neil asked in his rough voice, trying to act casual.

"She has a name. Cassandra. And she's in a meeting. Why?"

"Cassandra... What a beautiful name. Damn, you're one lucky guy," Neil chuckled.

"Thanks."

Neil shrugged his shoulders and went about his business. Instead of letting the conversation drag on, the notorious vacuum cleaner roared. I sighed and ate my lunch in... peace?

I couldn't help but wonder if Neil had been thinking about my fiancée, though. He had been checking her out, and now Neil was asking about her. I chalked it up to me being a bit amped up from Cass' pictures. Though, the thought of janitor Neil lusting for my fiancée... I had sure as hell had to push those thoughts well away if I were to get anything done today.

Though the devil on my shoulder was ever-present. I started to wonder what Cass would've thought if she knew Neil thought about her. Surely he did, right? Maybe I should tell her he asked about her? It wasn't anything but words after all. Couldn't hurt. Maybe someday.

I instinctively grabbed my phone and saw a new message attached with a new photo sent by Cass. She was wearing one of my flannels, yet again buttoned down. And nothing else. The picture didn't show much, but it was all about all the things that were just out of view. Her toned, heart-shaped ass, her beautiful breasts. Though I got an eyeful of those strong, firm thighs of hers.

Cass captioned it "Lunch at home today!" Damn it, this woman was really pushing it.

Later that night. We were eating some bolognese, talking about the day when I brought up Neil again.

"Your admirer was back today," I said. Cassandra looked confused at me.

"Babe, what are you talking about?" Cass asked. Though she was biting her full bottom lip.

"Neil. Even came around lunchtime again, hoping to get a glimpse of that hot ass of yours," I said, looking for her reaction. She just rolled her eyes.

"Still on about this?" she asked. "What he say then?"

I hesitated.

"Don't be scared, now. You think I'm gonna run off with that monster if he said my ass is nice?" Cass smirked. "Let me hear it, I wanna know what he had to say."

"He just said you had a nice name. And that I'm a lucky guy," I said. It wasn't that bad when I said it out loud. It was perhaps all the weight I had put on it that made Neil's compliment seem so wrong.

"So anyway," Cassandra said, moving on. "I was thinking we wondered if we should go fishing Saturday. Friday's tomorrow, but I have some stuff I gotta do until late in the lab, so I'll be, you know, late. But Saturday, we should definitely go fishing."

I looked at her quizzically. Why would she want to go fish? Cass found it exceedingly boring. It was certainly a first of hers to suggest a trip. I had dragged her a few times, but it had been a while now. She always tried to make the best of it, but I knew she wasn't the biggest fan, and thus I didn't really force her with me anymore.

Cassandra smiled widely, grinning at my confusion.

"I'm full of surprises, aren't I?" Cass chuckled. I knew she was up to something, but couldn't quite gauge what.

*

The rest of that week was filled with pictures of a more and more daring Cassandra. Some were more on the cute side. Selfies, some of her lifting her shirt to reveal her firm stomach. Others, however, were getting more and more naughty, as Cass got more and more comfortable with taking pictures of herself for me.

Thursday she sent me three photos while I was at work. One she took was in front of a mirror, wearing red workout tights and a baggy t-shirt in the gym, showing off her muscled, juicy thighs, with the caption 'Workout done!'. Following up right after with something completely new from Cass. She had turned her back to the mirror, twisted her upper body, and snapped a photo of her tights-clad ass. Man, with the lighting hitting her ass just perfectly, really showing the spandex stretching across her firm, wide-hipped ass. The text said, "And here's some buns!"

I chuckled at her cuteness. It even sort of rhymed. Probably on purpose, knowing Cass. Man, seeing her push herself, even without my encouragement was enticing. It made me yearn for where it might go, to see her creativity.

Another from the gym the same day, a small video snippet of a side angle of Cass stretching on the floor by tucking her knee under her chin, with the text 'Staying flexible!' I had never really gotten a video from her, so that was definitely another first! I couldn't help but imagine her trying to set up the shot to create the perfect angle to show her entire side as she pulled on her knee.

After finishing work that day, I hurried home. Cass had to stay home a lot at the end of the week, due to some assignments that were due Monday, only leaving to work out. Thus I had to drive myself to and from work.

The next day, Friday, Cass sent me three new photos. One similar to her stretching video, then two new ones. For the second, she had propped her phone up on a bench behind her as she was doing deeeep body squats. I had of course seen Cass workout before, but seeing it on film like this, being able to play it over and over again was a whole nother luxury. Also, I knew she was trying to push herself.

The final photo was perhaps her most teasing yet! Even more than when she wore my flannel earlier. The photo showed Cass in nothing but a towel, covering her upper mid-thigh to just above her chest! It was so erotic to see her with wet black curly hair, her strong hips still shining, and the muscles in her thighs attenuating tremendously. Her sexy body, combined with her playful smile... It was torture.

On my way home I could hear two new texts. Fuck, I wasn't about to check while driving. So when I finally parked in our driveway, I grabbed my phone immediately and opened the messages. I quickly scrolled up and clicked the attachment.