Cassie Ch. 01

Casper shook his head a little. Evelynn stroking his cock, Evelynn's fingers in his mouth, he couldn't tell if it was real or not. "Ah... nevermind. Mom always gets to me, I guess."

"Yeah, she does that. Believe me, baby, I know," Evelynn sat down across from him and slapped a sheet of paper down onto the table between the two of them.

"What's this?" he asked, taking a bite of his omelette as he glanced at the paper. The eggs were... alright. Evelynn was clearly not much of a cook, she'd overcooked the eggs a bit and hadn't used enough pepper. Still, it was more than Cassandra ever really did for him. The paper looked like a list of names? Maybe a list of stores?"

"I told you, silly, I'm taking you shopping. Those are just some ideas of places we could go. There's no way a healthy young man like you doesn't need something. Even if you don't want some cute clothes from Hot Topic or some skirts and panties, we can get you some more practical things, you look like you need some new shoes, for instance."

"M-Mommy! I do not need... why... I told Mom, I'm not crossdressing, it's just..." Casper blushed and sputtered.

"Methinks the lady doth protest too much," Evelynn snickered at him with a grin. "But really I was just letting you know that nothing is off the table. I owe you seventeen birthdays of presents and I can certainly afford to spoil you a little, honey."

"Is... is this a sex shop?" Casper asked, pointing at one of the stores on the list.

"Yeah, but they have some cute latex clothes, too. You haven't really worn tight pants until you've squeezed your way into a pair of rubber pants coated in silicone lube."

"I..." Casper trailed off. That actually sounded awesome. "Alright, we can look."

In spite of his earlier reluctance, Casper soon found himself swept up in Evelynn's eagerness, and was eagerly participating in the shopping trip. He picked out several cute tops and pairs of pants, a bunch of really nice eyeliner that was far superior to the stuff he'd been stealing from the bottom of Cassandra's makeup cabinet or buying on sale at drugstores. She took him to a ramen restaurant for lunch, which he was quite skeptical about since his mental image of ramen was instant noodles. It ended up being the best noodles he'd ever had and he made a mental note to scour portland for similar restaurants when he got home. It was late afternoon by the time they drove up to the sex shop and parked off to the side.

"So, ummm..." Casper murmured, wondering if he actually had the courage to go into the shop with his mother.

"Yeah?" she asked, shutting the car off and unbuckling her seatbelt.

"We're going in... together?" he asked.

"Yeah, is that a problem? I can keep the fact that I'm your Mommy on the down-low, if you'd like. If I grab your ass in the shop they'll probably just think I'm a cougar and you're my boy-toy." she winked at him.

"I don't think that's necessary," he laughed, shaking his head and getting out of the car.

"Alright, open offer though."

"Do you want to grab my ass, or something, Mommy?" he asked. For good nature, he bent at the waist a little bit and wagged it slowly in her direction. He figured if it was fair that she flustered and embarrassed him, he could do the same to her.

"Does a woman dying of thirst want a drink of water? You have the sweetest, fattest, most slappable ass I've seen all year, baby. I could just bend you over the hood of my car right now and make you squeal like a—"

"Alright, alright," Casper burst out laughing, realizing that embarrassing Evelynn was probably the most futile endeavor in the universe. When he looked at Evelynn, she has an extremely serious expression on her face. And he chuckled again.

"Let's just go," he relented. They went into the store together and by the looks of it, it was divided into two halves. One had shelves and displays full of dildos and various sex toys, the other was mostly clothes and various fetishwear. Casper went ahead of Evelynn towards the section of the store full of clothes. He took one step, and then Wham. Evelynn slapped his ass so hard that her fingers dug into the flesh of his asscheek. Casper yelped in distress, blushing furiously, but just as soon as she'd started, she let him go and walked past him into the clothing section.

Casper looked around the store for a second, and saw one of the cashiers, a pretty girl in her twenties smile and wink at him, but otherwise nobody seemed to notice. "Just for that you're buying me two pairs of pants," Casper murmured to her when he caught up with her.

"Fair enough, fair enough," she snickered.

Casper focused on the pants for now, quickly finding several that he liked. One of the store attendants came over and helped him try them on with the assistance of copious amounts of baby powder. He squeezed his way into one of the pants, and moved around in them a little to get a feel for it. As he ran his hands along the shiny, clingy material that was hugging his body, he had a bit of an epiphany. He knew people were 'into' rubber and latex, but he hadn't really understood it until just now. The way it clung to him like a second skin, the feel of it, the sound it made when he moved. He knew that Evelynn had successfully opened a bit of a pandora's box for him.

"Show us! Show us!" Evelynn's chanting voice came from outside the room. Casper opened the door and came out of the changing room. Evelynn gasped as she saw him, putting her hands over her mouth. Casper did a little twirl for the two of them, and Evelynn squeaked.

"Looks like a good fit," the store attendant commented, nodding in approval.

"I can die a happy woman," Evelynn whispered, staring at his ass.

"Uhh, they fit good. Can we get both of these?" he asked, gesturing to the other pair in the change room. They were two of the more expensive pairs in the store, but Evelynn had said...

"Yes! Of course!" Evelynn all but shouted in her enthusiasm. '"I'll meet you at the till."

Casper closed the door again, changed back into his regular pants, and came back out. He brought the clothes to the till where the cashier who'd smiled at him was waiting. She scanned the items, and then looked up past Casper, and smiled.

"Hey, Eve. New boy's a bit younger than your normal ones, huh?"

"No comment, Misuzu," Evelynn snickered, appearing next to Casper and placing a small bundle of things on the counter next to his new latex pants. Casper looked at it, and blushed crimson. It was a set of small buttplugs in ascending sizes and a good-sized bottle of lube. He looked over at Evelynn with a frown as she handed her credit card to Misuzu. As she handed it over, she slowly turned her head to look Casper in the eyes with a tiny, almost unreadable smile. He wanted to complain about how inappropriate this was, but he didn't want to throw a fuss or let it be known that he was here with his mother in front of the cashier, either, especially since the two of them apparently knew each other. He remained silent, blushing furiously, and Evelynn just winked at him and then completed the transaction as their purchases were bagged up/

"Mommyyyy," Casper whined as they got clear of the store. "I really didn't... I don't need you to buy me..."

"I don't know what you're talking about, baby, I bought these for myself. I date people sometimes, and they all have butts." Evelynn responded, sounding completely insincere. "Sure, I'm going to leave them unattended on my coffee table where any of my guests could take them without my noticing, but I definitely didn't buy them for you."

"...Really?" Casper asked dryly as they got into the car.

"Yep!" Evelynn grinned to herself a little bit, smiling at her own cleverness. Casper sighed and shook his head, completely at a loss as to how to react to Evelynn's parenting. He definitely wasn't going to take or use the buttplugs. Well... he kind of wanted to, but doing so would be admitting defeat.

As they returned home from their shopping trip laden with bags of clothes and makeup. As he deposited his spoils in his room, he spotted something in the backyard that he'd meant to ask Evelynn about earlier, but never had. He went back out into the living room and found her tapping away at something on her phone.

"So, uhh, Mommy, is that a hot tub in your backyard?" Casper asked, glancing out the window at the large, box-like fixture visible through the kitchen window.

"Sure is. Gosh, a soak does sound nice tonight after all that driving. I'll go fire it up, It'll take about half an hour to be ready, sound good?" Evelynn smiled dreamily.

"Sure, I'll go get changed,"

Casper went back into his room, and immediately realized he didn't really have swim trunks or anything like it. He had a few pairs of underwear, but several had already been worn and others probably weren't suited to hot tubbing. He ended up picking the pair that was least likely to allow his dick to flop out, and made a mental note to ask Evelynn if he could do some laundry tomorrow. He ended up answering texts for several minutes, a few of his friends from Portland were wondering where he was so he took his time answering their queries.

After finishing up with his messages and social media, he went out to the backyard, sliding the glass door open and stepped out onto the grass. He saw Evelynn was already inside the humming hot tub, facing away from him with her head reclined and her eyes closed. Even over the mechanical whirr of the jets, Casper could hear her humming happily to herself. He climbed up the other side and slowly eased himself into the water.

"Oh, wow," he murmured, enjoying the embrace of the heated turbulent water. This was the kind of luxury that he'd only really had at public pools and that was a different experience entirely.

"It's ridiculous how much it costs to maintain this, but it's one of the few indulgences I splurge on." Evelynn commented. Casper looked over at her, and jumped a little in surprise. Evelynn was not wearing a bra, the top half of her heavy, round tits were on display above the surface, with her large, dark nipples barely concealed by the translucent water. He was only surprised for about half a second, Evelynn wearing a swimsuit would have been extremely out-of-character, now that he thought about it.

"Very bold choice, wearing tighty whities," Evelynn winked at him and playfully splashed a bit of water at him, the sudden motion making her tits jiggle.

"You'd rather I be naked, then?" Casper giggled, shielding his face.

"I'm not going to force you, sweetie, but I will neg you and imply that you're a prude and a stick in the mud."

"Alright, fine. I can be an inappropriate nudist, too," Casper stuck his tongue out at her, and then dramatically stood up and stripped out of his underwear, tossing them over the edge. Evelynn immediately stifled a laugh, covering her mouth to keep her snickering under control. Casper looked back at her and scowled, seeing that she was looking at his crotch.

"W-What??" he asked, covering himself with his hands for a moment, and then right after, sitting down. His confidence vanished in a puff of smoke.

"Oh, honey, I'm so sorry, there's nothing wrong with you, it's just... well, you clearly didn't get your size from me." Though she was apologizing, Evelynn hadn't stopped smiling and didn't exactly look remorseful.

"Your... size?" he asked, his defensiveness slightly ebbing away only to be replaced by confusion.

"Oh... you didn't know?" Evelynn asked. When Casper didn't respond, she shrugged, and stood up. When her naked breasts came free of the water, Casper glanced away a little bit. He still felt like he could remember them pressing into his back the previous night, but maybe they had just cuddled. When she stood up to her full height, Casper immediately saw what she was referring to. Evelynn didn't just have a dick, she had a dick that made his look tiny. Heck, her dick made the guys he'd seen in porn look average. It was soft now, hanging low with a gentle curve down between her thighs. Her nutsack looked like more than a handful, the current sizet no doubt assisted by the heat. She was uncut with a decent amount of foreskin bunched up around the tip, but even as he looked, it twitched slightly, a rush of blood hardening it just enough for the foreskin to peel back a bit and reveal the tip of her urethra.

"Uhh... no I... no I didn't... Mom never mentioned." Casper blushed bright red at the sight of his Mommy's cock. It took him a few seconds to tear his gaze away from it, and the realization that he'd been staring a little just made him blush more.

"Well, I'm your biological Mother, you know. Did you assume we'd adopted you or used a sperm donor?" Evelynn remained standing for a few seconds and then eventually, slowly, sat back down, obscuring her cock beneath the translucent water.

"Yeah, I... I guess." he replied. "Mom never talked about you, and I never thought about it too much."

"Well, you're half me and half Cassandra. I was always so proud of you, doctors always said that I'd end up being infertile. I always joked around with Cassie that I'd knock her up just to spite them.

"So, did that have anything to do with why the two of you... split up?" Casper asked, gesturing towards Evelynn's crotch.

Evelynn reacted immediately, her good mood vanishing as though he'd flicked off a light switch. She scowled, not at him, really, but she was looking in his direction. She was quiet for several moments, and Casper shrunk back as the oppressive silence made his skin crawl.

"Cassie said a lot of things to me as we were breaking up." she said, her voice flat and intense. "A lot of the things she said were about my body, yes. She said them to hurt me, and it did hurt me. I don't know if it's part of why we broke up, I couldn't tell you."

"I... Mommy, I'm sorry," Casper murmured.

"Casper, I know I've been teasing you a lot this week but I want you to know that your body is beautiful. I just want you to be able to achieve your perfection."

"Y-Yeah. I know, Mommy. Thanks." Casper smiled at her. He wasn't entirely sure what to make of Evelynn's serious comments, the first serious comments he'd literally ever seen her make. The two of them spent a solid half an hour just sort of relaxing in the hot tub without saying much more to each other.

He floated closer, gave Evelynn a sideways hug, and got out first. She smiled at him and patted him on the cheek. "Sorry to ruin the mood, sweetie. See you tomorrow?" she asked.

"Yeah, see you tomorrow."

***

Casper woke up, and for a moment, wondered why, since when he opened his eyes, it was pitch black. A moment later, he felt the pressure in his bladder, and he realized that's what had woken him up. He glanced over at the digital clock next to the bed, and saw that it was 12:30 AM, not even that late. With a grumble, kicked his sheets away and sleepily rose to his feet. He walked into the kitchen, immediately realized that he was going the wrong way, and then pivoted and went towards the upstairs bathroom since the downstairs one didn't have the heated toilet seat he liked. As he reached the top of the stairs, he heard something. A muffled mumbling and moaning was coming from down the hall. Without thinking the situation through, Casper moved forward curiously, intent on finding out what the sound was. Evelynn's bedroom door was open, there was the dim light of the bedside lamp on, and she was unmistakably masturbating.

"Mmm, Fuck! Take Mommy's cum you little tease! Gonna fill your boypussy to bursting. You're gonna F-Fuck! Fucking leak Mommy's jizz down your thighs all day you sissy fuckhole!" The words and a whole continuous stream just like them came out of Evelynn's mouth. She was stroking her cock rapidly, although it looked... no that wasn't just her cock. She was using the fleshlight he'd seen earlier, and it was making obscene squelching noises as she beat her meat with it. Casper sobered up out of his sleepy state, and silently backed away to use the downstairs bathroom and its stupid cold toilet seat.

"Jeez," he murmured, shaking his head as he sat down and tried to pee through his half-boner. He tried to erase the image from his mind as he pissed, and he was still very tired so it wasn't that difficult, but... what had she been saying? It was probably all just nonsense sex-talk. Heat of the moment stuff. He finished peeing and wandered back to his room and back to sleep. Best... not to think about it...

***

"Morning, sleepyhead!" Evelynn chimed. Casper was already half-awake, sleepily thumbing through his phone's notifications under the covers. He yawned and pushed the sheets aside.

"ghwur," he murmured.

"What's that? You wanna be a good boy and come along with Mommy for her run?" Evelynn asked, grinning at him with her hands on her hips.

"Umm? Run?" he asked, the fog clearing a bit.

"Yes! It's a thing we do where we use our legs to propel us through the hills! It provides us with exercise!" Evelynn plopped down onto the bed and leaned in, kissing him on the forehead and then ruffling his hair until it floofed all over his eyes and he couldn't see.

"Oh. Oh! Uhh, yeah, sure, why not," he said, pulling away a little and fixing his hair.

"Yay!" Evelynn kissed him again several times, most of them landing on his cheeks and forehead but one lingered on his mouth and he could have sworn that he felt her slip a little tongue in there, but before he could think too hard about it, she'd bolted back up off the bed and swept out of the room like a hurricane. Casper sat there for a few moments, blinking the sleep out of his eyes, and then went to get changed.

He emerged from his room and found Evelynn in the kitchen eating a bowl of cereal. There was another bowl on the table, and Casper helped himself to it. Evelynn was dressed in a pair of yoga pants and a t-shirt, which was more dressed down than he usually saw her by quite a lot. The pants did absolutely nothing to hide her bulge, and he clearly saw the outline of each of her impressive testicles, and even... no he couldn't see the veins, that had to be a fold of fabric. When she caught him looking (maybe he was staring a little, if he was being honest,) she silently reached down and grabbed it, giving it a tiny squeeze as she smirked at him.

"S-Sorry. I just... uhhh," he mumbled around a mouthful of cereal.

"I usually tuck but we're going for a run so nuts to that. Pun intended." Casper laughed a little at the awful joke, shaking his head. They finished breakfast, and Evelynn immediately grabbed a little backpack, slipping her arms through the straps. "Onward!" she raised her arm triumphantly, as though the two of them were off to do something glorious. He followed her outside and felt the warm sun contrasted against the cool autumn breeze.

Evelynn proved to be much more energetic than Casper expected. She set a quick pace, which Casper kept up with at first, but eventually he started to lag behind and Evelynn made a point of circling back around and heckling him teasingly.

"Your Mother is twenty five years older than you and she's doing circles around you, Casper! Let's see some hustle!" she shouted in her approximation of a drill sergeant voice.

"I am... not... in... Ahh!" Evelynn slapped his ass, hard, and he stopped and scowled at her.

"Not cool!" he pouted, rubbing the sore handprint.

"Hah! Sorry, couldn't resist. Take a break?" she did a very poor job of restraining her laughter, but removed her little backpack and withdrew some bottles of water and a little hand towel from it.

"Yeah," he agreed, taking the bottle of water she held out to him and wandering over to a nearby tree to sit down next to it.

Evelynn sat down next to him and wrapped an arm around his shoulders. She slyly handed him a granola bar like it was contraband, and when he looked over at her, she winked and shushed him. The two of them sat quietly for a while, drinking their water and eating their granola, watching some birds flit from tree to tree.