Casper wandered up his driveway, a bit of a wobble in his step and a goofy smile on his face. It was late, way past his curfew. He paused as he approached the front door and looked down at himself. He’d snuck out of the house wearing a t-shirt and a set of jeans and then gotten changed at the party. He was currently sporting a cute goth look with eyeliner, a mesh top, ripped leggings and black boots. He’d intended to change back before he got home, he didn’t need his Mom’s prissy, condescending critique of his fashion choices. He was home now, though, and he realized that he must have forgotten his street clothes in his friend’s car. He paused for a moment, wondering if he should stop and go searching for them, or if he should just risk his Mom seeing him in this outfit.
Casper gently placed his hand on the doorknob and twisted it, opening the door as silently as he could. There was a light on, but his Mom had probably just left it on for him, she wasn’t necessarily waiting to ambush—
She was there, sitting in a living room chair like a gargoyle with her hands folded in her lap. “Do you have any idea what time it is?”
“Tsh.. later than… should be.” he slurred, still rather tipsy.
“And… what the fuck are you wearing? Why are you crossdressing?? ” Her voice went up an octave and her hands balled into fists.
“I’m not! This is just… It’s...! You wouldn’t understand.” he tried to explain to her, but she was too angry and he was too tipsy.
“I understand perfectly. You’re a goddamn pervert, just… Just like Her! ” Even as she said it, the two of them froze, the weight of her words squeezing them both.
“Like who, Mom?” Casper asked softly.
“You know. ” His Mom, Cassandra, replied with ice in her voice.
“Yeah, I do. You won't ever talk to me about her but I know,” Casper muttered bitterly. She’d meant Evelynn, his other Mother. The two had split up when he was young, and Cassandra refused to talk about her save for small outbursts like this.
Casper slammed the door to his room, exhausted, frustrated, and still pretty drunk. The two of them had fought for over an hour, and he was tired. Not just tired tonight, but tired of fighting with her in general. She’d always been difficult, but the second he’d started expressing an interest in being anything other than a musclebound macho guy, she’s started really escalating on him. He’d wanted to drop out of hockey to make more time for theatre and choir, and she’d lost her mind. One of his friends had come out to him as trans, and she’d mysteriously found a new job across the city that made it almost impossible to see him anymore. He’d come to terms with his bisexuality a little while ago, and he was absolutely dreading that conversation with her, if it ever came to it. She’d said… he was just like her, like Evelynn. His Mom’s definition of a pervert was definitely one that she played fast and loose. Maybe Evelynn was just… cool? Maybe she’d be accepting? Cassandra had seemingly sworn off any sort of homosexuality, even though she hadn’t said it, but maybe Evelynn hadn’t?
The thought stuck in his head so poignantly that he remembered it in the morning when he woke up. He went to his computer, and started to search. He combed through court records until he found Cassandra’s name change. She’d changed her surname from Davis-Wu back to just ‘Wu’ seventeen years ago when he’d been two. He then jumped onto social media, searching for Evelynn Davis and… just like that, he found her, his other Mother. She lived in Vancouver. There was a border between them, but geographically, she was closer to him than any other major city. It was only a few hours by bus. He opened up a Direct Message, typed ‘Hi, I think I’m your Son, Casper?’ into it, and stared at the screen, frozen. He squeezed his eyes shut, looked away, and hit enter on his keyboard, sending the message. He stared at the screen, at the sent message for a little while, feeling some anxiety bubbling up. This was stupid, he shouldn’t have—
Casper Wu (09:42 AM): Hi, I think I’m your Son, Casper?
Evelynn Davis (09:45 AM): Oh my Gods, Yes!!! Does Cassandra know you’re messaging me?
Casper Wu (9:48 AM): No. I’ve been having a lot of problems with her lately…
Evelynn Davis (9:55 AM): Oh Honey, you’re preaching to the choir on that one. Honestly, I’ve wanted to reach out and talk to you for years but there’s already enough bad blood between Cassandra and me, and I didn’t even know if you’d want to hear from me.
Casper Wu (10:01 AM): She never talks about you. We had a fight and she called me a pervert ‘just like you’ last night and I dunno I’m getting so sick of fighting with her. Seemed like a good excuse to see if I could find you.
Evelynn Davis (10:10 AM): Tell you what, I’m going to extend an open invitation to you to come stay with me. (Temporary or long-term) You’re 19 now, you can make your own decisions.
Casper Wu (10:12 AM): Live with you? IDK that seems like the nuclear option, doesn’t it?
Evelynn Davis (10:14 AM): LOL! I just meant for a week or so, silly. Maybe if Cassandra realizes that you have some agency of your own, it’ll make her cool down a bit.
Evelynn Davis (10:16 AM): Honey, I’ve got to go to work now. I’d love to keep in touch even if you don’t ever find your way out here to see me. Best of luck with Cassie <3
Casper Wu (10:16 AM): Thanks. I’ll think about it.
A week later, Casper stepped off the greyhound carrying his suitcase, looking around the bus terminal for a woman he’d never met. He spotted her fairly quickly, she was a tall woman, easily towering over Casper or Cassandra who were both only about five foot five even without the two-inch heels she was currently wearing. She had thick, dark hair that would have been down to her shoulders but it was currently done up in a ponytail and paired with long, side swept bangs. She wore a simple white dress with a V that revealed a decent amount of the flesh on her prominent breasts. She had dark green nail polish on and was carrying a cute handbag. She spotted him too, and waved energetically, walking over to him with a spring in her step.
“Casperrrr!” Evelynn squealed, happily. She grabbed him in a crushing hug and energetically lifted him clear off the ground. His face got buried in her cleavage and he blushed profusely as he tried to squirm free of her grasp. Evelynn proved to not only be quite a bit taller than him but quite strong too, and she squeezed him breathless with the hug.
“Gosh, I wasn’t sure that I’d ever see you again, you got so cute on me!” Evelynn planted him back down on his feet and leaned down to plant several kisses on his forehead, cheeks, and lips. It was bizarre to him to have her being so affectionate with him, his other Mother had always been so stoic. Getting even the most brief, chaste hugs out of Cassandra had been a chore.
“H-Hey,” he mumbled, smiling a little, her affection and enthusiasm proving to be infectious. Evelynn squealed happily and smiled at him with her hands on his shoulders. “It’s like a dream. You’re… wow! You must be so tired from the bus ride, come on I’ll take you to my place.” She quickly snatched Casper’s bag from him before he could protest and led him out into the parking lot, humming happily to herself as she went. She had a spring in her step and a bubbly energy about her that Casper couldn’t take his eyes off of. The contrast between Evelynn and Cassandra felt like something that belonged in a theatre performance, and it boggled his mind that the two women could ever have been a couple at all, let alone one that had had him.
Eve took him to what he thought looked like a very nice car (Not that he knew anything about cars, really.) He did know enough to recognize that it was much newer than anything Cassandra had ever owned. She threw his bag into the trunk and moved quickly, opening the door for him. He couldn’t help but giggle at her enthusiasm, and got in.
“So how was the trip?” she asked, settling in next to him in the driver’s seat and starting the car up.
“Bit long, but it was alright. They searched me for drugs at the border, the racist pricks.”
“Yeah, no kidding,” Evelynn sighed and shook her head. “Did you end up telling Cassandra you were coming?” she asked. Her voice had a bit of an exploratory probing to it, like the words were caustic and dangerous to handle.
“No. I tried to, but, she’s just… She’s so hard to talk to, and it only gets harder. I ended up packing a bag and my passport while she was at work, using the ticket you sent me and just… coming.” He laughed nervously, hoping Evelynn wouldn’t be mad that he’d snuck away from Cassandra like this.
Evelynn put a hand on his shoulder. She was still driving so the glance she shot him was passing, but somehow it had a lot of weight to it. “Something happen recently?”
“I came home, and I was wearing… I wasn’t even really crossdressing. I went to a party, I had on a fishnet top and…” he trailed off. They were at a stoplight, and Evelynn was staring at him, wide eyed like a puppy.
“I bet you’re ADORABLE.” she gushed. “The girls must be all over you!”
Casper cleared his throat, squirming uncomfortably. He felt like he was reasonably popular with girls, but not… just with girls.
Evelyn glanced at him out of the corner of her eyes. “Not the girls?” she asked carefully, as if feeling out the sentence.
“I mean” he said, feeling a knot of unease deep in the pit of his stomach, “maybe not
the girls?” Even as he said it, he could hardly believe it. He’d been struggling to hide this from Cassandra for almost a year and now he’d blurted it out in five minutes with Evelynn.
He flinched at Evelynn’s squeal of delight. “Oh I bet you break so many hearts. You clearly take after me!” There was a note of pride in her voice at the claim.
“You aren’t upset?” he asked, taken aback by the strength of her approval.
Evelynn laughed. “Oh please! Honey, it’s 20XX. Only boomers are straight anymore. I married your mother, do you really think I’d be upset that my son is bi?
Casper thought he heard a faint note of bitterness at the mention of his mother. He had sometimes thought it was strange that Cassandra had been married to a woman and then pivoted so strongly in such a prudish direction. If anything, it made sense that Evelynn wouldn’t have done exactly the same. She might be able to relate to him more than Cassandra else possibly could. “I haven’t really told Mom, I don’t think she’d take it well.”
“Really?? I knew Cassandra had turned into a stick in the mud but to think that our son would be afraid to come out to her? Well, it’s settled! I’m going to show you I’m the cool Mom. We are going shopping for you this week. Anything you want.”
“Evelynn, you don’t—”
“For one thing, young man, I am your Mother, call me Mom. For another, I want to take you shopping and there’s nothing you can do to stop me.”
“I… I can’t. Cassandra is Mom. You’re…” He paused.
“That’s fine. I can be Momma. Mother? Mam? Ma? Mommy?” She shot him another look, smirked, and nodded. “Yep, that’s the one. Mommy.”
Casper laughed. “No, that’s…”
“Settled? Darn right it’s settled,” she laughed back at him, and completely shut down his attempts to argue the point. He didn’t actually call her Mommy, rather he just avoided calling her anything at all as best he could. Her house was out in the suburbs, and it took them about an hour of driving to get there. They mostly chatted about him, his interests, his life. He’d seen from her profile on social media that she was an author, but not gotten much else out of it. Her actual house was… surprising to him. He’d thought Vancouver was a big, urban area, but somehow she managed to drive him to a relatively rural road without leaving the city. It was dense with trees, like a conservation area, and she drove him up a winding road to reach her house. It wasn’t the only house in the area, but it was pretty quiet and secluded just the same.
“No place like home, eh?” Evelynn asked. “I’ve got a room you can stay in. You wanna order a pizza for tonight?”
“Sure,” he agreed, looking around the house. It wasn’t a mansion, but it was probably four times the size of the little house that he lived in with Cassandra in Portland. Evelynn gave him directions to the room, and he carried his bag there. He clicked on the light, and paused in the doorway for a moment. The room before him was the pinkest, frilliest, most stuffed-animal filled room he’d ever seen. It looked like something out of a movie.
He chuckled a little, it was actually kind of refreshing. Cassandra had freaked out over him expressing himself in even the least non-traditional way, and here Evelynn was giving him a pink bed to sleep in. The room had several dressers, a big closet, and a nice desk with a computer on it. He dumped his bag on the bed and wandered back off to find Evelynn.
“What’s with the room Mo—” He paused as he entered the living room/Kitchen and saw Evelynn with her phone in hand. She looked at him, and grinned.
“Say it, or the pizza doesn’t get ordered,” she said with a low, teasing, almost flirty voice and a playful smirk. The two of them stared at one another for a few seconds, Evelynn’s eyebrow slowly arching higher and higher.
“Mommy, what’s the story with that room?” he relented, laughing a little at his Mommy’s absurdity.
“Oh, I had an exchange student in there last year. I kind of spoiled her, she was such a darling. It’s not a problem, is it? I never got around to donating away her things.” She dialled, and raised a finger to stymie his response as she spoke to the pizza place.
“No, it’s fine, it’s just for the week. I’ll just move the stuffed animals around. Can I use that computer, though?” he asked once she was done ordering.
“Oh, of course you can. It should be able to connect to my Wi-fi but the password is on the router if not.” She settled down on the couch and patted the cushion next to her. He came over and settled in next to her. She crept a little closer to her and put her arm around his shoulders. “Gosh. You look so much like her, you know? People ever tell you that?”
“Dunno… Mom doesn’t really… get out much, anymore. Can I ask… What happened between the two of you?” Evelynn’s arm engulfed him and he found himself being drawn into her. His head pressed into the side of her left breast and he tried not to pay too much attention to it.
“Do you know what I do, baby?” she asked.
“Umm, you’re an author?” he replied.
“Yup. A lot of what I write is very naughty, though. A little while after you were born, Cassie just sort of… assumed that I’d stop? She came across my latest manuscript and sort of… went off on me. Started screaming about setting a wholesome example for you. Honestly, I was totally blindsided by it all, I had no intention of changing what I was writing, and I never thought we’d raise you as some sheltered kid who didn’t know what sex was. The fighting got really bad and she just… took you and left. Went back to America.”
“She… she was allowed to do that?” Casper asked, a little stunned. He’d expected some bad blood between his two parents, but something like this was kind of shocking.
Evelynn sighed, sounding genuinely sorrowful for the first time. “I didn’t have any excess capital to commit to a lawyer at the time, and, honestly, I expected Cassandra to play fair. She didn’t. Cassandra’s brother took the case and totally blindsided me. They found a sympathetic judge that totally ate up their argument about my writing being inappropriate. She got full custody almost before I realized what was happening.” She looked away from Casper, a pained expression on her face.
They were quiet for a few moments, and then Casper leaned in and gave her a hug. The conversation diverted from there and he went on about the things he was doing, the choir he’d stealthily joined, the school he was applying to, things like that. The pizza took a while to arrive, and when it did, the two of them settled down on the couch to watch a movie on Evelynn’s rather large television. Before he even knew what was happening, he melted into Evelynn’s softness and warmth and drifted into a doze.
He dreamed that he was kissing someone. He wasn’t sure who, it was more of a vague sense of another person. They felt so nice, so warm, and it was so amazing to be kissing them. He moaned softly, gyrating his hips, a mysterious friction against his cock making sparks run through his body. His tummy contracted, twitching, and he whimpered as his hips bucked. He felt sooooo good, and a warmth spread throughout his body starting at his crotch. He gasped, and as he noticed something oppressive and wrong on his face. He felt a tiny surge of panic as his breath didn’t quite come as it should.
He gasped, twitching in panic, surging awake. His face was pressed firmly into Evelynn’s armpit and he’d gotten a mouthful of her dress as he’d tried to breathe in. There was a bit of a lingering taste of sweat and Evelynn laughed at him as he sputtered a bit.
“Oops?” she asked. “Twisted wrong in your sleep, huh?” She raised her hand to her mouth and licked the webbing between her thumb and forefinger.
“Y-Yeah,” he murmured, wiping a bit of the drool off his face. He noticed a moment later, that his cock felt wet, and in horror, he looked down to see the big wet stain in his pants. The dirty dream had made him cum in his pants right next to Evelynn. He had a moment of terrified embarrassment as he squeezed his thighs together, positive that Evelynn had noticed and was going to be furious with him for being such a pervert.
“I think it’s time for you to get some proper sleep, young man. I won’t be around much tomorrow but you can have the run of the house. I’ll have more time for you after that, okay?” Casper blinked in confusion as Evelynn spoke. Had she… not noticed? She musn’t have. There was no way Evelynn was nice enough to just pretend she hadn’t noticed, she’d teased him about everything else.
“Yeah. Thanks, E— Err, Mommy.” Evelynn beamed happily as he called her Mommy and kissed him on the top of the head. He squirmed a little, hoping to get his back turned to her as soon as possible to conceal the wet spot. As quickly as he could, he bid her goodnight and got swept up in another energetic goodnight kiss before he returned to his new room. As he crawled under the fluffy bedsheets, relief flooded him that he hadn’t made a complete fool of himself, and he drifted off to sleep feeling strangely accepted for the first time in a long while.
The next morning, after getting dressed, Casper booted the computer up, and sat back waiting for it to load. It snapped to life fairly quickly, dumping him onto the desktop. He was a little surprised, he’d been expecting some old dinosaur of a computer for the spare room, but it actually seemed like it ran better than what he had at home. He opened up the web browser to watch some videos for a little, and instinctively hit the shortcut to bring up browser history so that he could pick up where he’d left off. Of course, it wasn’t there, and he chuckled to himself as he realized his error, going to close the tab. And then… he saw the browsing history.
<Crossdressing slut gaped open by BBC>
<Sissy bitch used and abused>
<HYPNO: Be a good cock whore for Mommy>
<T-Girl spitroasted by huge strapon DICKS>
<Training the Sissy Maid>
<femboy cums hands-free in chastity - what a good girl!>
<FISTING! Force-Femmed twink takes it wrist-deep>
<Locked in Chastity forever - Eternal Servitude Pt.3>
He knew it was porn at the first glance, that much was obvious. It just took him a few seconds to realize the common theme. He stared at the… extensive list for a few seconds, somewhat overcome with morbid curiosity and somewhat overcome with just regular curiosity. He wondered if it was the exchange student’s porn history, or if it was Evelynn’s. He ended up closing the web browser, getting away from the computer and wandering through the house to think a little.
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.
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.
“Mommy, I’m… I wish I’d gotten a chance to know you before this,” he finally said, enjoying the moment.
“Me too, baby,” Evelynn agreed, giving him an affectionate squeeze.
“I think, uhh… I was thinking about applying at some of the schools up here. Maybe go to one of the Uni’s up here next semester.”
“Shouldn’t be too hard. You have a Canadian citizenship, after all.” Evelynn remarked.
“...I do?” he asked.
“Yeah, of course, you have one Canadian and one American Mother, that’s a pretty common case for dual-citizenship.”
“Oh. I hadn’t thought about that.”
Evelynn chuckled and booped his nose with a finger. “And to answer your question, silly, yes of course you can stay with me if you end up doing that.”
“..Thanks, Mommy,” Casper giggled, snuggling up against her.
After resting for a bit, the two of them went back down the hill to Evelynn’s house. Casper went in first, huffing and puffing and sweating. Evelynn was definitely glistening a little, but she was nowhere near as beat as Casper was.
“I’m… gonna… shower…” Casper wheezed.
“Go ahead, you know where it is.”
Evelynn’s shower was huge, it was at least sixteen square meters with one long, narrow showerhead that covered the center of the room with warm water. Casper wasn’t sure why one would opt to put this style of shower into a house, but the fact that he could stretch and wander around was a strangely nice little convenience. As he stood under the stream of warm water, his cock throbbed needily and he sighed in frustration. He still didn’t understand why his libido was so on fire these past few days. True, he was a nineteen year old boy and thinking about sex wasn’t uncommon for him, but his body had never been so wantonly and uncontrollably horny even when he didn’t want it to be. He gathered up some soap and started washing his chest, and as he ran his hands across his nipples, an electric tingle made him gasp. He gently squeezed one of his nipples, which seemed more swollen than usual, and moaned softly. His cock twitched at the strange tingling pleasure, his body responding like it had made an amazing discovery. Casper contemplated the phenomena for only a few moments before he brought his other hand up to cup and squeeze his other nipple. He moaned and whimpered gently as he fondled and teased himself, exploring this new sensation.
“F-Fuck… so weird…” he murmured to himself as he continued playing with his chest.
“Someone’s having fun~” Evelynn’s sultry voice came from right next to him, and he jumped in surprise. The sudden motion made him slip a little on the slick tiles, but Evelynn grabbed him to keep him steady. “Oh, sorry! You alright, baby?” she asked, squeezing him close.
“Y-Yeah, I’m…” he trailed off as he felt it. Evelynn’s cock was pressing hard into his ass, and one of her hands was wrapped around his chest, fingers idly resting on one of the nipples he’d just been fondling so passionately. “Mommy, what are you doing in here…” he murmured, disentangling himself from her.
“You didn’t close the door, sweetie. I thought that meant you wouldn’t mind sharing, and I needed a post-run shower, too. Are you alright? I know being open with your body can be a big first step for some people.” Evelynn stepped directly under the stream of water, wetting her hair down. She started running her fingers through it with a happy sigh, and Casper looked away, terribly embarrassed. He thought that he’d closed and locked the door, but clearly not, if Evelynn had just walked in without him hearing the door open.
“S-Sorry… I don’t normally…” he murmured.
“Oh don’t apologize, sweetie. You have a gorgeous body and your sensitive boytitties deserve to be played with.” She flicked her hair backwards out of her face, the water keeping her bangs held back.
“They’re not sensitive… or, boytitties,” he huffed indignantly, looking away.
“Oh?” Evelynn asked. While Casper was looking away, she reached forward, firmly grabbing one of his nipples with thumb and forefinger.
“A-Aah!” Casper yelped, overcome with a shock of pleasure and pain as Evelynn squeezed.
“Yeah, not sensitive at all,” Evelynn cackled, seizing his other nipple in her other hand. She grabbed a handful of the soft flesh of his chest and kneaded them. Casper moaned and whined, his knees buckling a little. He looked desperately into Evelynn’s eyes for mercy, but she looked back at him with a sort of manic glee. “You’re definitely not moaning and panting like a desperate little sissy slut because Mommy’s playing with your poor nipples,” Evelynn husked, taking slow, deliberate steps forward.
“M-Mommy! Evelynn! This is… wrong,” Casper gasped, weakly putting his hands on Evelynn’s arms. He was so horny, so overwhelmed by Evelynn’s expert kneading of his chest, that he didn’t even know how to resist.
“Wrong?” she asked. With a quick motion, she pulled him close, spinning him around so that his back was pressed up against her front. She reached one hand down, and grabbed a handful of his ass, squeezing so hard the fat of his cheeks bulged around her fingers. “There’s nothing wrong about fondling a tight, sweet little body like yours.” He felt the heat of her cock, now swollen with blood. It was wedged in between his ass cheeks, and she gyrated her hips gently, rubbing the meat against him. Casper felt his own cock throb and twitch, he was overwhelmed by the closeness and intimacy of the moment, overwhelmed by Evelynn’s presence and dominance.
“Gods, you have such a glorious, perfectly fuckable little ass, you know that, baby?” Evelynn asked, pulling him closer up against her. “I’m so tempted right now to just bend you over right now and Stuff. You. Full.” She accentuated each word of the end of her sentence by roughly slamming her hips forward into his ass. The simulated fucking made him shiver, hyper-aware of how precariously close her dick was to his hole.
“I can’t…” Casper murmured. His hand went halfway to his cock, but he stopped himself. It had almost happened instinctively, his body felt like it was on fire with lust at that moment.
“...Can’t?” Evelynn asked.” There was something strange about her tone. “The first time I fucked your Mom’s slutty asshole, she complained it would never fit.” She moved quickly, roughly bending Casper over at the waist so that he was forced to steady himself with his hands on the wall of the shower. She pressed two wet fingers against his ass and applied some pressure.
“H-Hey, you’re not…” Casper didn’t believe that she was actually doing it right up until his ass relented to the insistent pressure. There was a tiny pinch of pain as they went inside, and Evelynn wasted no time exploring, rubbing her fingers along the walls of his butt. She curled them downward into a spot that made his body tingle, and he moaned at the strange, alien bloom of pleasure that cut through the faint ache of his hole being stretched.
“Yeah, and then ten minutes after she said it, she made noises just like that,” Evelynn growled softly, her grip on Casper’s nipple tightening. Casper tried to struggle and get away, but Evelynn had leverage on him and the floor was slippery enough that he didn’t think he could kick and thrash without totally falling over. “All week I’ve had to put up with you teasing me.” Casper felt Evelyn’s hot tongue trail along his cheek. “Showing off your hot little fuckable body. You have no idea how much you’ve been working me up.” A sharp, suckling bite to Casper’s neck drew a cry of pain from the boy. He bucked under her, struggling. She moved too quickly, her hand on his nipple going up to entwine in his wet hair. She pinned his face against the warm shower tiles until his skull ached under the pressure. “I think it’s time,” her sultry purr tickled his ear. “I’ve been patient enough with you. Let’s see what needy sounds you make when it’s Mommy’s cock in your pussy instead of a pair of fingers.”
“W-What?” Casper gasped, cold panic forming a knot in his belly. This wasn’t teasing, she wasn’t just being inappropriate and messing with him. She meant it. “Evelynn, stop, I don’t want—”
Her hand pressing his head to the tiles squeezed, pulling his hair roughly. “Don’t you lie to me, Cassie. You were born for this. If that cunt hadn’t taken you from me...” There was an angry intensity in her voice that frightened him. He squirmed and pulled away, finally managing to loosen her grip on him but slipping as he did. Evelynn’s fingers came out of his ass and her other hand came away from his head but Casper fell on his ass, twisting so that his back was up against the shower wall. Evelynn towered over him, and he shrank away as she once again got close to him.
“That’s good, Cassie. That’s where you belong, on your knees in front of my cock. Why don’t you show Mommy your appreciation and give her a kiss?” Evelynn grabbed her cock and slapped it against Casper’s cheek.
“Stop it!” Casper raised his hands and slapped away Evelynn’s cock. “Fuck, Mom was right, you’re a monster.” He winced, expecting some kind of reprisal, but when none came, he seized the opportunity and scampered away from her a little. He got away from her and rose up to his feet, feeling his heart racing like crazy in his chest. He looked over at Evelynn and she was… frozen. She was staring at where Casper had been when he was pinned against the wall, one of her hands slowly clenching and unclenching.
“...Cassie…” Evelynn whispered, still staring into space.
Casper decided not to waste the moment, he darted out of the shower, grabbed a towel, and went to his room. He sat on the bed and covering his face with his hands. He didn’t imagine that. He hadn’t imagined that second night, either. Evelynn… she was serious.
A few minutes later, a knock came at the door. “Sweetie? Can I come in so we can talk about this?” Evelynn’s voice came from the other side of the door. Her voice was… not entirely normal, but it seemed to have regained some semblance of its old self. The door wasn’t locked, it didn’t even have a lock. She could just barge in if she wanted to.
“I… I think I’d be more comfortable if you stayed outside,” Casper replied.
“Alright, well… I’m so sorry, baby, I just… That… what you just saw doesn’t normally happen to me. I’m so sorry…” her voice sounded fragile, broken, defeated. Casper wasn’t sure what to believe, though. Was it a trick? Had Evelynn had an episode of some kind?
“I don’t know if I believe you, Evelynn. I think I should just go home.” Casper spoke quietly, still feeling shaken by the experience.
“I understand. I’ll buy you some bus tickets and we’ll call you a cab to take you to the bus terminal tomorrow morning, okay?” Casper felt a tiny spike of paranoia at her words. That meant he’d have to stay here tonight. Did he trust her that much? Maybe he should just leave now, walk or pay for a cab himself. Maybe just stay at a hotel or something. That frightened him too, though. He didn’t have much money, Cassandra didn’t provide much for him, and he didn’t know the city at all.
“O-okay,” he acquiesced. Evelynn did seem to be remorseful. He wasn’t about to forgive her for trying to rape him, but… it was just one night.
“I’ll bring you some lunch so you can eat it in there. I’ll give you some space, but I’ll be out here if you want to talk to me.” There was a brief pause, as though she was waiting for an answer. When one didn’t come, her footsteps echoed down the hall as she left. He sat there on the bed, his thoughts still chaotic and fearful, until Evelynn knocked on the door again.
“Food out here for you,” she called through the door, and nothing more. He opened the door after a bit, and she wasn’t there. There was a plate of leftover curry on the floor, and he took it into the room and ate it quietly. He had no idea what any of this meant, what Evelynn was going through or how he was supposed to feel. Maybe she had some kind of disorder or… something. She’d been calling him Cassie, as though he were actually his Mom. Maybe in that moment, she’d been unable to tell them apart? Maybe that was why his parents had truly split up. Maybe Evelynn just needed to be on medication, or to see a counselor, or... As he ran the scenarios through in his head, his vision began to swim, it started to feel like he was floating underwater.
“W-Whuh?” he murmured, feeling everything swirl around him. Before he could really get a grasp of what was happening, he collapsed forward onto the desk, consciousness slipping away from him.
Casper woke up, but it wasn’t normal. He felt weak and sluggish, not tired. He was lying on something soft. He struggled to open his eyes, and then he tried to sit up. His arms… his arms they wouldn’t move. He squirmed and rose up, getting into a sitting position. The room he was in was dim, lit by a single, sputtering lightbulb hanging from the ceiling. The walls were cinderblock and there was a hot water heater sitting in the corner, pipes running up into the ceiling. He was lying on a simple mattress covered by a white sheet. It was barely big enough for him to even lie on. He realized a moment later that his arms were tied or bound together behind his back by something. He pulled against them a little, struggling against it. It didn’t feel like ropes or handcuffs it was like… some kind of sleeve? There was something on his neck, too. It was a collar, a big thick one made out of nylon and there was some kind of box on it, held onto the side of his neck.
“E-Evelynn?” he called out, afraid. What had happened? Had she done this? Was he in the basement?
His voice echoed off the walls a little, fading into nothing.
“This is… fucking insane…” he murmured, trying to get onto his feet. He got halfway up when the sleeves binding his arms went tight and he was pulled backwards. He twisted around and saw that there were ropes attaching him to a hook drilled into the stone. Footsteps echoed outside, and his eyes snapped to a heavy metal door on the far wall. With a heavy clank and screech, it opened, and Evelynn stood in the light.
“Morning, sleepyhead~” she said, echoing what she’d said that morning… or yesterday morning? Had it been a full day, already?
“Evelynn this is fucked up, what did you do? What’s going on?” Casper asked, trembling in fear. Evelynn had a cold, angry look in her eyes, and she had a sort of icy stillness to her body language even as she took several slow steps forward.
“I tried to be nice with you, Cassie,” Evelynn said, not answering his question.
“I am NOT Cassan—” Casper gasped as a sharp, stinging pain bloomed from his neck as the collar buzzed. His body tensed up, his breathing halted for just a moment, and his limbs twitched in agony. It stopped just as rapidly as it had started, and Casper moaned in pain.
“Good girls listen when Mommy is talking. Bad girls get shocked.” Her voice had a deathly finality to it. She clearly wasn’t in the mood to argue.
“Ug…” Casper groaned, shuddering. He looked up at Evelynn defiantly, but she had a remote control in her hands, pointed at him, and the threat was very clear. He didn’t say anything again.
“I didn't want to be hard on you, Cassie. You were being a huge fucking tease, but we were having fun. Right up until you…" She scowled, sneering at him, and Casper flinched, anticipating another shock. When he looked back at her, she'd moved closer, and was pulling up the hem of her dress so that her cock could flop free. It was rock hard.
"Now… do what Mommy told you and give her a fucking kiss."