Cassie Ch. 01

Evelynn's house was nice, well-decorated, tasteful. He felt a little out of place, almost like he wasn't supposed to be touching anything. As he passed through the living room, he spotted something he hadn't seen the night before. There was a door in the middle of the hallway, one that looked like it might lead to a basement or something. It was locked, but not just locked, it had a ridiculous padlock on it. He approached the door curiously and inspected it for a moment. It wasn't a normal-looking padlock, even. It actually looked custom-made, with a big, fancy keyhole and huge, heavy locking mechanism. It was like something that you'd expect to see on a movie set attached to a chest full of cursed pirate gold. He gave it a bit of an experimental tug and pulled on the door to see if it was just for show, but the door didn't even begin to budge and clearly was very locked.

"Guess I'll have to ask her about it," he mused, and went looking for some food. He found some cereal easily enough and went through cupboards until he found bowls, and then drawers until he found a spoon. His phone buzzed as he ate, and he peeked at it to see that Evelynn had texted him.

Evelynn Davis (8:16 AM): Morning, sleepyhead! Let me know if you can't find anything around the house. I won't be back until late, but I promise I'll make time for you tomorrow. See you tonight <3

Casper puttered around the house for a little. He went back to the computer full of sissy and trans girl porn and avoided it, watching some silly internet videos instead. Afterwards, he explored the house a little more and ended up opening one of the upstairs doors. It was Evelynn's room, clearly. He immediately felt like he was intruding. He stopped, and intended to turn around and leave, but then, something caught his eye, and he did a double take. There was a flesh-coloured cylindrical object, discarded at the foot of the bed. His morbid curiosity overwhelmed him, and he stepped forward to confirm.

It was a fleshlight, a used one. A tiny stream of what could be cum or lube had oozed out of it, and when he stepped forward, he smelled it. Definitely cum. He shook his head and backed away, leaving Evelynn's room and closing the door behind him. He shouldn't have done that, shouldn't have snooped. He couldn't help but wonder what that was, though. Had Evelynn had a guy over, that night? If so, why would he have used a fleshlight? Why would it have been left at the foot of her bed, discarded as if in haste and afterglow.

He ended up going for a hike, making his way through the trees and hills surrounding Evelynn's house. He found that there were only a few houses in the immediate area, but when he climbed a tree, he was able to get a good enough view to see that the rest of the city wasn't far off, he was still surrounded by civilization. It was maybe a twenty minute walk to the nearest major street. Satisfied, he climbed down and headed back to Evelynn's house, and started taking a few notes of places he wanted to go in the city while he was there. An idea occurred to him and he grabbed his phone to text Evelynn.

Casper Wu (4:45 PM): Mommy, do you mind if I make dinner? Can I use what's in the fridge and pantry?

Evelynn Davis (4:51 PM): Oh my Gosh! I get a home cooked meal?? Use whatever you want Sweetie. Wow, I'm excited, you're so sweet!! <3 <3 <3

She sent him a barrage of emoji with that last message, more than she normally used. Casper wasn't entirely certain what she was trying to communicate with them, but it was definitely positive, so, with that settled, he went to the kitchen. He found enough ingredients to make curry, and so he started cooking. He was getting close to being finished when the door opened, and Evelynn entered, singing energetically to herself.

"Darling~" Evelynn crooned, sweeping into the kitchen and wrapping Casper up in another smothering hug as he worked. "This looks delicious, my adorable little housewife. How was your day? Keep yourself occupied?" she asked.

"It was fine, I went for a walk. What's that giant lock on the basement door?"

"Hah! It was a gift from my publisher, actually. Bit of an inside joke from one of my books. The basement's not safe right now so I figured I may as well use the silly decorative padlock. It's cute, isn't it? I think it looks very mysterious and foreboding." Evelynn giggled at him and poked him in the ribs with a mischievous grin.

"So, no bodies stashed down there?" Casper snickered.

"Nah, just whips, chains, and restraints." Her grin grew, challenging him, daring him to call her on the bluff, but he didn't. She put some of her things away, still humming to herself. He served the curry, which had turned out quite nicely, and Evelynn seemed to barely be able to contain her eagerness as he did. As he sat at the table, Evelynn mischievously placed a pair of wine glasses onto the table next to the plates, and grinned at him, brandishing a bottle with an eyebrow raised in question.

"Oh, sure? It's alright? I'm not twenty one." he said with a soft laugh.

"Legal drinking age is nineteen up here, darling~" she giggled at him, pouring the wine with a wink. The two of them chatted and ate for a little while, Casper feeling a bit of a warm buzz from the wine and inexplicably, a weird half-chub that he did his best to ignore. Evelynn was very beautiful and nice, and the boner... no it wasn't about her. It had to be just hormones or something.

"So, Sweetie. I was thinking today." Evelynn changed the subject abruptly away from science fiction. "I assume nobody ever had the backdoor chat about safe sex with you, huh?"

"Well, Mom avoided it like the plague but I got the basics from school and the internet. Condoms, pregnancy, all that stuff." He answered. It was honestly kind of cute that she was worried about him like that.

"Oh, darling, no. I meant..." she made a circle with her thumb and pointer finger on one hand and then moved her other pointer finger through them back and forth a few times.

"Umm...?" he frowned, confused. "I don't follow."

Evelynn snickered and leaned in. "Backdoor. Butt stuff. Anal Sex." she spoke the last one slowly and loudly, pausing after every syllable. She then put four fingers together to continue her gesture. The digits no longer cleanly fit into the circle formed by her fingers and her teasing grin grew wider. Her lewd gesture slowly became significantly more lewd as she continued trying to roughly force them further inside.

"Okay, Okay!" Casper both snickered and blushed. "What about Butt sex?"

"I can't have my son getting hurt when things get put into his cute little tushie!" Evelynn gave him a serious look, folding her hands on the table.

"Hey... maybe I'm the one who puts... uhh, things. Into other people's—"

Evelynn burst out laughing. Casper scowled at her and crossed his arms. "What's so funny?"

"Oh come on, sweetie, I can smell a bottom a mile away. Don't be shy, the world needs bottoms! Gosh, there'd be an awful lot of cold dicks otherwise." Casper's embarrassment finally got the better of him and he looked away. As he broke eye contact, Evelynn cackled victoriously. "Knew it!"

"Mommy, c'mon, this is embarrassing." Casper muttered.

"Alright, alright. I'll just talk to myself and remind myself how important lube is, how spit isn't lube, and about how you always need some warm-up because one of your sphincters is involuntary." Casper burned with awkward embarassment as Evelynn cited off a bunch of rather detailed but very sterile information about anal sex. His ears did perk up a few times at bits of information he hadn't known, or that he'd thought were myths. He avoided giving her the satisfaction of confirming that he needed to hear it, though. He thought about it a little and it was pretty funny actually that Evelynn was a huge over-sharer and Cassandra was so stoic. As their meal wound down, Casper's phone rang, and he glanced over to see something he'd both expected, and that made his stomach twist into a knot. Cassandra was calling him.

"I... should take this," he murmured, looking away from Evelynn and accepting the call.

"Uhh, Hey," he answered.

"Really? You vanish, don't even leave me a note, and all I get is a 'Hey'?" Cassandra wasn't shouting but her voice was full of malice.

"Yeah, well whose fault is it that we're not on speaking terms right now?" Casper replied, scowling. Evelynn set her fork down and looked at him thoughtfully. She mouthed the name 'Cassandra' to him, eyebrows raised questioningly, and he nodded.

"Don't you Dare! I cannot believe this. Where are you?" She snapped, her facade of control starting to slip away.

"I'll be home early next week. I'm fine, you don't have to worry."

"That's not what I asked you."

"It's just... I'm staying with Evelynn for a few days. It's no big deal." Casper felt a tremor run through his body. He didn't want to have this conversation. Why'd he even answer the phone?

"Very funny. Where are you?"

"Vancouver. I'm just getting to know my other parent. Is that so bad? Don't I have that right?" he shot back, getting riled up by the third degree coming from Cassandra. It was in that moment that he realized he was a little tipsy again. Evelynn had been generous in refilling his glass and he wasn't used to drinking wine.

"Wait... Casper, you're joking, right? Please tell me you're not with her right now." Cassandra's voice changed ever so slightly. She sounded... afraid?

"Yeah, she's right here, we just had dinner."

"Oh my Gods, Casper, no. no, no, no, no, no, you can't. You need to get out of there you need to get away from—"

"Oh come on, Mom, this is just sad. I'm an adult now, you can't keep me locked away in my room." Casper growled in annoyance. He knew that Cassandra didn't like Evelynn, but to put on this act to convince him that she was dangerous was pathetic.

"CASPER, PLEASE, LISTEN TO ME." Her voice was panicked, desperate.

"No! Shut the fuck up, for once! It's just a week, Mom, I'll see you on tuesday."

"CASPE—" he hung up, getting the speaker away from his ear with a wince.

"Sounds like that went well," Evelynn murmured softly. Casper barely heard what she said. He was trembling. He was so tired of this. So tired. He couldn't even have dinner with Evelynn without Cassandra... doing this.

"I'm gonna go to bed," he whispered, picking his phone up.

"Hey, sweetie, why don't we talk about this?"

"Tomorrow... tomorrow." he stood up from the table abruptly and rushed away to his room. Evelynn called after him again but he ignored her,moving through the halls to his room as quickly as a walk could take him. He flopped down on the bed, feeling the tears well up. He couldn't keep doing this with Cassandra. It was getting harder and harder. He choked back a sob, and shook his head. He was also still super horny and it seemed to be getting more and more intense, like his body was out of control. His boner hadn't gone down and in fact it was starting to throb needily, demanding his attention.

"What the fuck is wrong with me?" he growled softly, twisting and turning. He buried his face in his pillow, trying to think unsexy thoughts, trying to... ugh. He jumped out of bed, kicking his clothes off and digging out his pajamas. His cock pulsed and twitched demandingly as he freed it from the jeans, but he ignored it. He wasn't in the mood, he just wanted to forget about Cassandra for once. He crawled under the covers, his anger at Cassandra slowly but surely being replaced for his anger at his stupid libido that wouldn't leave him alone.

"Fine!" he muttered, reaching down and grabbing it to start stroking. He masturbated out of spite and out of a desire to be able to get some sleep, but he gasped and squealed as the shock of pleasure caught him off-guard. It felt so nice, so intense, it was an outlet for an intense amount of lust and horniness that he hadn't realized he was harboring. He tried not to think about why he was so horny, choosing to blame his hormones, and instead just stroking rapidly, moaning and whimpering softly.

Suddenly, the door squeaked open, Casper yelped in surprise as he realized Evelynn had walked in. He immediately stopped what he was doing and squeezed his thighs together, as if to suppress his lust. He looked over his shoulder wide-eyed, burning with embarrassment that he'd been caught.

"I know it's hard, sweetie, but Mommy's here, you don't have to cry by yourself," she whispered, crawling on top of the bed next to him and putting her arm around his chest, hugging him close to her. It didn't seem like she'd realized that he'd been masturbating. Casper realized that she probably heard him whimpering and moaning and mistakenly thought he'd been crying. Part of him wanted to correct her, but, well...

"M-Mommy, it's... uhh..." Casper murmured incoherently, trembling with embarrassment and residual lust. His cock still throbbed needily, desperate for the release he'd promised it.

"Shhh, it's okay baby," Evelynn cooed into his ear, hugging him tight, her fingers running through his hair. "You don't have to explain anything to me. I've dealt with her before, I know how hard it is."

Casper squirmed uncomfortably. He had a boner trapped between his thighs that wasn't going away, and Evelynn was so soft, her big tits were pressing heavily into his back. Her warm breath tickled his ear and he whined softly in frustration.

"What's the matter, baby? You're so tense. Mommy's here, you can relax." she whispered. Her other hand rubbed his chest gently. It drifted down until it was on his stomach, and she squeezed him closely, pressing his body against hers.

"I-It's nothing, I was..." Casper murmured lamely. He didn't know what to say. Just going to sleep? Crying over Cassandra? Jerking off?

Evelynn's hand dipped a little lower, touching first his thigh, and then, ever so gently, her fingers brushed up against the hard, throbbing tip of his cock. Casper jerked as if he'd been shocked, pulling away from her a little bit. He was being firmly squeezed and cuddled by Evelynn though, and she was stronger than she looked. His attempt to squirm away barely got him any space at all.

"Oooh," Evelynn laughed softly in his ear. And then, slowly, her hand dipped under the waistband of his pajamas, her fingers delicately yet firmly wrapping around his cock. Casper gasped. In shock? In denial? Pleasure? He wasn't sure. "I see what you were doing," Evelynn teased gently, her hand giving a painfully slow, teasing squeeze and stroke.

"M-Mommy, don't..." Casper whined, but even as he did, his hips twitched, thrusting gently into her hand. He was so horny he couldn't think straight.

"Don't worry, baby, it's just us here. Mommy will make you feel better, okay?" As Evelynn spoke, she moved her other hand from petting his hair to his neck. She slowly, sensually wrapped her hand around his throat, not choking him or constricting his airways at all, but she simply held him there possessively as her other hand started to stroke him. She swung a leg up and over his hip, pinning him to the bed and to her and she started to pump his cock. Casper moaned out loud, unable to protest or struggle, so overwhelmed in his feelings of ecstasy as Evelynn slowly, deliberately jerked him off.

"Doesn't that feel nice? Nothing complicated. No worries, just Mommy's nice soft hand for you to cum in. Don't be afraid, sweetie, moan all you want, let Mommy know if she's doing a good job." Evelynn's husky voice was right in his ear, her breathing intense. Casper did as he was told, moaning, writhing ineffectively in Evelynn's embrace. Erratically twitching and humping his hips into the soft, squeezing warmth of her hand. Her motions were slow, deliberate, and steady. Casper felt like he was going insane, he started spasming and thrusting against Evelynn's, desperate to increase the stimulation, desperate to cum.

"M-Mommmmyyyy~" Casper whined, any other words too complicated for him to form.

"Hmm? Does Mommy's sweet little girl want to squirt her sissy cum?" Evelynn teased, the hand around his neck squeezing gently, silently communicating the control and the power she had over him in that moment.

"Y-Yesssss," Casper screamed, the strangeness of Evelynn's comment not even registering in his brain before the storm of passion that was overwhelming him. Evelynn stopped stroking for a moment, squeezing his cock with all her strength, the vice grip making him gasp in something between pleasure and pain. Then, she started to stroke him more quickly, and Casper squealed, arching his back as his pent up lust was quickly built up past the breaking point.

"Mommy! F-Fuck!" Casper babbled. He twisted his head to the side a little, squeezing his eyes shut as the orgasm quickly built up. Evelynn's lips met his, and her tongue slipped into his mouth as he came. Casper moaned into the kiss, passively letting Evelynn kiss him and her tongue gently explore his lips. He came with explosive intensity into Evelynn's steadily stroking hand, and she immediately twisted her grip a little, still squeezing and stroking but keeping her hand cupped over the tip of his cock. His body slowly went limp, drained of strength as he rode out his orgasm, Evelynn still holding him close, trapping him, kissing him as slowly and deliberately as she wanted to. She moaned softly, thrusting her tongue into his mouth, dominating him with her soft lips. After a while, she finally broke the kiss, purring happily in his ear.

"Gooood girl," she whispered, squeezing out the last drops of his cum from his exhausted body. Casper breathed a sigh of relief as she removed her hand from his overly-sensitive cock. A moment later, she slipped one of his fingers into his partially-open mouth, and he immediately tasted the slightly sweet, bitter taste of cum. His cum.

"Clean up after yourself, baby. Don't make a mess on Mommy's sheets," she cooed softly, slipping a second finger into Casper's mouth. Part of him thought he should resist, but he did this with his own cum sometimes anyway, and soon a third finger joined the first two. He sucked on them gently, and Evelynn immediately purred in approval, whispering encouragement into his ear as she slowly pistoned her fingers in and out of his mouth. With her fingers clean, Evelynn slowly withdrew them and kissed him on the cheek, relaxing her pinning grasp on him just a little bit.

"What a good girl~" Evelynn murmured, one of her hands wandering down to cup his butt and give it a tiny squeeze. "You get some sleep now, okay? You'll feel better in the morning." She kissed him again on the top of his head and delicately slipped out of the bed, letting him drift off to sleep almost immediately.

***

Casper awoke the next day with the first rays of morning sunshine coming through the window. The smell of bacon was filtering into the room and he rubbed his eyes, confusing and conflicting thoughts running through his head. What happened last night? He'd fought with Cassandra over the phone again, but then...? Had he and Evelynn...?

No, that couldn't be right. He did vaguely recall Evelynn jerking him off, but he'd been a little drunk and inexplicably horny. It had to have been some bizarre oedipus complex dream. He wandered into the kitchen to see that Evelynn was wearing nothing other than a bra, panties, and an apron. She was frying bacon in one pan and working on an omelette in another.

"Good morning~" she trilled, taking a moment to plate the eggs and bacon and set them on the table for him. "You sleep okay?"

"Uhh, yeah," Casper murmured, taking a seat and avoiding staring at Evelynn's scantily-clad body. "Mommy, did... did something happen last night?"

"Well you got a call from Cassie, we snuggled a bit, and then you fell asleep. I think I may have refilled your wine a bit too generously," she laughed, turning the heat down and plating her own breakfast.