Cassandra's Adventures Pt. 04

Laying on her back, breathing softly, utterly exhausted. Neil looked at her. Cass was such a cute girl. But hot. Not only because how trimmed and in shape she was, how ample her features were, but also her sunny disposition and her endless hunger to getting fucked. Hell, Neil wasn't sure if it was a dream that too, but he could've sworn she had woken him up to fuck him once more during the night.

But looking at her now, Neil just had to give it to her once more. If not to steal her away, then to have her for himself.

Knowing that he shouldn't push his luck, he found another condom on the nightstand and rolled on. He then moved in between Cass' legs, gently spreading them and hooking them around his waist, scooting closer to her. Both of them had fallen asleep in the nude, so it was easy access. At first he considered just sticking it in like this, so he could look on those gorgeous tits and her abs, but Neil hatched another plan.

Instead, he crawled up her still sleeping body, taking the blanket with him. He found himself on top of her, snugly covering them both in his blanket. Laying intimately like this, Neil angled his hips so that he parted her legs and wrapped them around his hips, and then his cock found her entrance. Wrapping his hands around her shoulders, holding her tightly into him, Neil entered Cassandra.

She had been slowly waking up from Neil climbing on top of her, but realizing what he was doing, she quickly spoke up.

"Oh no don't-" She started, but Neil shoved his lips onto her mouth before she was able to protest.

He moaned warmly into her mouth as he slowly started to press his cock into her more. Feeling him on top of her like this created a connection between them Cass didn't really expect. Not only because he had such a big fucking tool and it felt good, but also from the closeness and gentleness of their fucking.

No.

This wasn't fucking.

Neil was making love to her.

Realizing this made her eyes roll into the back of her head. The taboo of something so intimate with a guy like Neil was overloading her senses in every way. Her body had been yearning for something intimate and him being this thick and yet gentle gave her the salvation she desperately craved. Neil released her lips and picked up the pace a little bit seeing her reaction, though still keeping it tender and gentle.

"Oh... gooood... you bastard..." Cass moaned, starting to tremble all over.

This vile, big dicked monster making sweet gentle love to her, holding her closely and tenderly frenching her was so far from anything she'd ever expected, from anything she had wanted. Cass had up to this point been afraid of something like this happening. And feeling how good it felt, her fears were not without argument. Neil being so good to her was exactly what she had been afraid of. If Neil could give her this too?

Neil angled himself up so that he could stare at her beautiful face smiling back up at him. At her beautiful breast softly bouncing with each firm thrust. At her abs crunching as Neil was stretching her out. Never stopping his tender thrusts into her, pressing hard into her, feeling her out properly, and also letting Cass feel just how good he could make her feel.

Cass looked down to see the wide thick shaft disappear into her over and over, and each time it did pleasure rolled through her, sending jolts of electricity through her. Each time that thick shaft disappeared, it filled her up like nothing else.

"You're so fffucking big," Cass moaned in delight. Neil's size and the slow deliberate thrusts truly highlighted their lovemaking.

Then Neil leaned down again, his hungry lips on hers, wrapping his arms around her again so he could press into her even firmer.

He was holding her closely while pressing deep into her, mauling her insides with a passion unlike anything else. The details of his cock stretching her out so good. She was so completely full, so completely satisfied, she could almost cry. The emotional reaction of her own body betraying her like this was almost too much to bear.

But damn it felt good.

Then after a series of extra firm thrusts, it was like Neil tore through some extra layer within her. Like he was, even now, discovering new grounds inside her. The lovemaking went from great to even better. Whatever it was made Cass start to meet his slow thrusts with her own hips, eager to take him into this new place. Cass felt him so deep and so good. She had no idea how or what had changed, but whatever Neil was doing was just right. Right up inside her, against her very deepest depths. She couldn't get enough of it.

Every time he pressed forward she felt this new sensation wash through her, like gentle waves rocking her back and forth. Right up against her cervix she could feel this gorgeous cock bring her to even new heights and make her feel things she didn't know were possible. It was so delicious, so incredible. And with each thrust it got better and better, and Neil had plenty of deep passionate thrusts to give.

Her legs fell limply to the sides, dangling with each slow thrust, jolting softly each time Neil bottomed her out. He would hold still inside, before giving her shorter thrusts in her very depths. He had done this before, but this time it was just so much better. Cass was so wet and gushing from how good it felt, holding around his broad shoulders tightly. She could have screamed from sheer delight, but Neil's lips sealed her shut.

And even better, Neil started to pick up the pace ever so slightly again. Cass could feel his huge cock start to expand even further within her and she knew then he was going to cum soon. His tender lovemaking and feeling him grow even more inside her made her kiss him with even more passion, clutching his back with her fingers. She desperately wanted cum with him.

"You ready?" Neil moaned, interrupting their kissing.

"Yesss. Please. Let's cum together," Cass moaned and rewrapped her legs around her new lover.

"You got it," Neil said, sinking his lips to hers again.

Soon after, Neil felt his balls tingling, and when Cass pressed her soft legs around to coax him to stay as deep as possible, he knew it was too much. He couldn't hold back anymore. He didn't want to. Not now. He sunk his hips down into her once again, this time holding firm up against her deepest most delicate parts.

As he pressed all the way inside her, Cass felt Neil's giant cock twitch within her. It felt so different from the other times. Not bad different, just like... usually the warmth would glow inside her and press back and forth inside of her. Now it felt like the warmth shot out and expanded throughout, shooting deep inside her, coating her insides along with Neil's long strokes. The sensation was enough, however.

She was panting frantically into his mouth as her orgasm reached its crescendo. Her small soft whimpers were muffled by Neil's insistent tongue exploring her mouth, something which she reciprocated with just as much passion, but all her nerves were on fire from their mutual orgasmic bliss.

Cass was too far gone in wild pleasure to think much of it. The expanding warmth seemed to never stop, and even more of it shot into the deepest parts of her with each twitch from Neil. It felt so good. After a few jolts, Neil started to slowly drag his big cock back and forth again, thrusting tenderly into her. She could feel him press all the way inside her, pressing his giant cock head up against her cervix, sending more glowing warmth into her. That glowing warmth felt like nothing else, and she couldn't get enough of it.

Neil held deep with each thrust, twitching so many more times. This intimate sex was new to him as well, and experiencing it with Cass had made him shoot more than ever before. He had to have her again, but for now he was focused on emptying as much as he could. He was so sensitive by now, each motion became jagged. He trembled all over from how sensitive he was.

Finally, Neil sat back and dragged his long, thick cock from Cass' hot sleeve. When half of his cock was out, Neil saw what he had suspected.

The condom had torn.

And she hadn't even noticed.

Neil groaned out loud in deep satisfaction. Some evil part of him didn't want to tell Cass about it. Nothing would hit the spot of his ego better than to thoroughly breed his boss' future wife. This sweet, tender little thing getting bred by the dirty old janitor. The thought was almost too good.

But there were two reasons to let her know. Three actually. First, Cass would notice soon enough. And if she didn't, if Cass got pregnant there were only two culprits, and she was a smart little thing so she'd figure it out. Secondly, in conjunction with the first reason, if this were to continue he'd had to earn her trust. Telling her this would do that. Even if he'd let out the part where he felt the condom tear. He could feel it in her reaction that her body knew the difference, but her mind had been naive to the notion. Thirdly, Neil fucking hated pregnant women. So if they fucking were to continue, that was a no-go.

"Oh shit," Neil said, feigning surprise, hoping she'd buy it.

"What?" Cass asked, barely paying attention. She was contemplating if she could get Neil hard again. Whatever he did at the end there was just amazing, and it was something she knew she needed to have again.

"The condom broke! The old damn thing. I guess I fucked you too hard— Hey where you going?"

*

Cass had immediately gone to a pharmacy close by Neil's house and got a plan B. It wasn't as risky as Neil lived the opposite direction of Isaac and her place, thus few of the people who recognised her would have any suspicion. Pesky neighbors.

Fuck.

Isaac!

Cass was on the verge of tears, more or less sprinting home. Not only had she completely forgotten about her dear fiancé during the night, lost in a new world of pleasure, but she'd also somehow wound up no doubt getting knocked up. How could she ever live with herself?

How the fuck could she be this stupid even? To let something like this happen. And in hindsight, what seemed so natural and beautiful at the time almost made her want to throw up now. Neil making love to her? What the actual fuck was that about? It felt like, yuck, love, but there was no way she would ever feel something like that to anyone but Isaac. Hell, the love she had for her future-husband was probably stronger than for her own family. She swore she would kill and die for her man, and to jeopardize any of that sent her mind into shambles.

She was desperately searching her mind on how she would make it good. How she would tell it. Part of her knew Isaac would love that she lost herself, perhaps she knew better than Isaac even. But she didn't want to listen to that part of her. Cass wanted Isaac to scream at her, yell at her. Let her know how awful she was treating their relationship.

But Cass knew better. Or. She was smarter than that. Isaac would forgive her. She trusted that, and he trusted her. It was hard to argue that some of that trust had been broken though by letting it go as far as it did. She hoped, no she knew that they would come out on the other end stronger. And besides, she knew she could tell the stories and turn Isaac on like no other. Maybe if she told the fucking part, without the accidental creampie... Creampie, a word she'd never use, but here in her train of thought it rolled into her mind.

Just as Neil's cock had rolled through her. Deep. Bare. Fuck, she knew now that the tearing she felt was Neil getting through the condom, entering her pussy raw. It felt so magnificent. And how good did it feel when Neil came? Fuuuck... It had to happen again... right?

Cass couldn't be thinking like this. She shouldn't. Her head had to sit straight. She partly wanted to quit the whole ordeal, to get the fantasy out of her life, but having already tasted it... It was too sweet for her. It had corrupted her, and altered something deep within her.

Cass wanted to scream. Her body and mind was at war, and her body was winning, and she knew it. There was nothing she could do to combat it.

She would have to find some sort of compromise. Cass checked her phone. Clock wasn't too late in the day, and Neil and her had been able to record most of their action.

*

The anxiety I felt that Wednesday morning was unbelievable. Waking up to no Cass. I was smart enough to draw the conclusions about what had happened, but still, I was a bit uneasy. Both worried for Cass' well-being, and also for how far Cass already had gone.

But it wasn't like when they fucked the first time. Like, I was more or less coming to terms with that, and the debauched naughtiness of Cass' actions was something I got incredibly turned on by. Even now. I knew that I could trust her in all those aspects.

Of course, I had been up most of the time jerking off to all the fantasies of what they were doing. Imagining the things Neil did to Cass. She was no doubt having the time of her life. I knew perfectly well that was something Neil could give her. I just hadn't expected her to go to his place and let alone stay over. Knowing Cass, I knew it was probably not something done deliberately.

I had even gotten a text from Neil, from Cass' phone, calling us Eskimo brothers, the insensitive bastard. And then a video later, in the middle of the night. It was Cass' cute face on a pillow, seemingly sleeping. Then, from above, shot a fountain of cum all over her face, making her giggle. Needless to say, that one video was plenty of... material.

Her naughty behavior, leaving so much to the imagination, was such a turn-on. Like pure denial. I knew it was wrong to cave in like this, that it wasn't part of the deal to keep me out of it. But the horned-up jealousy I felt was like no other, and even when I'd busted a nut I was ready to go again immediately after. Especially having at least some videos and photos from Cass' previous adventures.

So when Cass showed up at lunch Wednesday afternoon, I was mildly surprised. Pleasantly, but still surprised.

"Someone has had a rough night? Did you walk over?" I commented. Cass had been at home no doubt, fixing herself up, but the way she walked... If you knew what she'd been up to, it was obvious.

She looked guilt-stricken as she took her seat and pushed a Tupperware with some of her good chicken pasta in it toward me.

My light tone seemed to ease her a bit.

"Can you forgive me?" Cass asked, looking at me innocently. She truly felt bad about having stayed over. And I couldn't help but think it was warranted. But seeing her disheveled like this, feeling guilty. It was catching a teen who was hungover for the first time.

I couldn't help but chuckle a little. My reactions seemed to ease her further.

"Of course. How can I stay mad? But god damn it, try to get some of it on film at least!" I laughed. I got up, walked up behind her chair, and gave her a hug from behind. Cass reached for my hand and pulled me in tighter.

"You're spoiling me... You're spoiling me with a very dangerous game," Cass said.

"Really now? So how was it? You better not skimp on the details, not after last night!" I said, sitting down in my office chair, folding my hands in my lap.

"Well, you're in luck," Cass began, snaking her sexy butt out of her chair. "Because I got most of it on tape."

Cass slowly turned her back to me, giving me an amazing view of her ass in bright, tight khakis. God damn it, to think that was all mine. Or... at least mostly mine. Cass looked over her shoulder at me, and gave me a mischievous smile, making her way over to the door. When she reached it, she turned to me and gave me a toothy, wide grin, and locked the door.

I gulped. I wondered what plans she had on her mind as I watched the extra sway she had in her hips as she walked over and around my desk. I looked up at her, raising an eyebrow, as if to challenge whatever her plans were.

"You better scoot your chair back a bit," Cass said, touching my shoulder gently. I did as I was told. "Good boy. Now, let me turn and hook my phone up to your laptop here, and then we'll see if we can't spend this lunch, and perhaps a bit more, exactly what I did last night?"

"Hell yeah," I said. Fuck. When she turned it on, she turned it on.

And talking of turning. Cass moved in front of me, turned and then bent excessively over my desk while fumbling with hooking her phone up. This gave me an amazing view of her tight pants stretching magnificently over her ass. Fucking hell, her ass was such a prize. But I wanted to see where this was going, so I let her press her ass back against me for a short minute before she turned back around, smiling wickedly down at me.

"Exhibit A, Cass getting railed from behind by big dicked Neil," Cass said. She then sunk to her knees in front of me, between the desk and my legs.

Was this it? And in my office? Two things I always wanted to experience. And to think, without Neil, who knows when it would ever happen, if ever. In some twisted way, I had him to thank for opening Cass' sexual horizon.

Cass smiled up at me, seeing me realizing what she was up to. She moved her head near my pants and started sniffing my belt.

"I love a man who wears leather. Especially leather belts," she said. "But these will have to go if we are to properly examine the crimes committed yesterday."

Cass had opened my fly, unbuckled my belt, and was working my pants down my legs as she spoke, and to help her out, I lifted up so she could slide them all the way to my ankles. My boxers were next, setting my rock-hard erection free.

"Someone's excited," Cass said, giving me a few slow jerks before turning around and hitting play.

On the video, from a nightstand by the looks of it, I could see Cass bent over towards the camera, with Neil slapping up against her over and over. Her face was lit up with lust, and her moans were loud and as intense as the fucking she was receiving. Her tits swayed firmly back and forth as she pressed back against Neil's giant cock.

I was so focused on the video that I gasped in slight surprise when I felt something wet and warm around my dick. I looked down and finally saw my beautiful fiancée with my own dick in her mouth. Finally. And it felt so good. I tilted my head back in sheer pleasure. Fuck. It was almost too much, but Cass seemed an expert. She saw my signs and slowed down.

"Calm down, big boy. We have lots to watch," Cass said. "Though, I guess we can save some of them for later."

"Ho- how many aaaare there?" I asked, barely able to keep my voice intelligible.

"Oh, there is plenty," Cass answered coyly. She took my dick into her mouth again and gave me a few rapid bobs before getting up again. "Though there was one specific incident when we didn't get to film."

"Yeah?"

"Yeah. And in many ways. Fuck, it's so wrong to even say this, but," Cass once again gave me a series of deep, fast bobs before continuing while stroking me, "In many ways, it was the best one. The best fucking, that is... He climbed on top of me, and Isaac, he made love to me. No fucking. He made love. And it was the best lovemaking I've ever received."

I groaned out loud, damn near cumming.

"Now, I'm gonna tell you the icing. Neil made love to me so good, and during it, the rubber broke. I didn't notice. He said he didn't but I don't believe that. So... that is not the icing. Neil fucked me so good after ripping the rubber, so good. His big cock is even better raw. And then he filled me up. Like, really filled me up! Neil came inside me, and to be honest, I loved it. It was soooo good- oh-"

In raging jealousy and horniness, I started cumming, and Cass even shot her face down my cock, easily taking me to the bottom, and let me shoot all down her throat. It felt incredible. Not only did I get my first blowjob, but Cass even deepthroated me and let me cum in her mouth. No, in her throat. And on top of that, I knew who taught her that...