A Step Too Far
This is the second story about Ashley's misadventures, after Careful What You Wish For! I recommend you read that first, as it's the main introduction to the characters and sets the scene for this one. Enjoy!
Part 1: A Wish Fulfilled
"Lick faster, dummy." Cathy snapped, rapping Ashley's head with her knuckles. The young warlock struggled to obey, his jaw aching as his tired tongue tried to coax a third orgasm from his girlfriend's pussy. None of his usual tricks were working, and if he kept up much longer his muscles would just give up on him. Who knows what she'd do to him then! In desperation, he went for her clit, licking and sucking at the swollen nub of flesh. Cathy moaned hoarsely, shivering against the coach. Almost there, Ashley told himself, just a little longer. "Yeah, just like that, you pathetic little bitch! Yeah!" His girlfriend screamed, her legs trembling on either side of his head. He kept his mouth firmly nestled between her legs as she moaned her way through yet another climax, but at least his tongue could rest a bit.
Like always, it took her a little while to stir, her icy blue eyes glowing with satisfaction as they fluttered back open. She sat lazily back, her arms spread out on the back of the couch. Ashley rose onto his knees, still trapped between her muscled legs. The musky juices of her pussy tingled on his tongue. It felt like all he'd tasted since she'd started making him eat her out.
A whole week of this. It felt way longer. Everyday after school Cathy texted him, he'd dress up like a girl, makeup and panties and everything. Then she'd come over. He'd eat her out until she came a couple times, and when she was satisfied she'd go. There'd been one day where she hadn't spoken a word to him. She just sat down on his couch, spread her legs and pointed. Like he was a toy or a pet. Worse still, she hadn't even touched him back once! At least that first time she'd made out with him a little, now even that was too much bother for her.
The young warlock shifted anxiously. The head of his stiff dick rubbed against his favourite pink panties, and he couldn't help but bite his lip. He was really hard, just like always happened when he wore his girly clothes, his tiny cock pressing against the silky softness of his underwear. Maybe she wouldn't notice this time, or maybe she'd be happy enough not to say anything. Then he saw her cold gaze flicker down between his legs, and he winced.
"You're hard again." She sneered, disgust in her eyes.
"I'm really sorry, Cathy...I can't help it." Ashley stammered. His cheeks were flushed red-hot, but his stomach felt cold and sick. Why couldn't she be a little nicer? He'd given her three orgasms, hadn't he?
"Fucking pervert, getting off on wearing panties." His girlfriend spat. "You know I hate seeing that. I should print a few of those pretty photos we've taken and stick them on every billboard in school. Let everyone know what a pathetic little worm you really are."
"No, please don't!" The young warlock gasped in horror. "You can't!" Those photos were so embarrassing! If anyone saw him posing in girl's underwear, he'd be the laughing stock of the entire school! More than he already was...
"Give me a reason not to." Cathy drawled. She wrapped one leg around him as she spoke, her naked thigh pressing into his shoulder. He shivered as her hot, muscled skin brushed against his. Her legs were so hard and toned, she felt like she was made of stone next to soft little him.
"I'll lick you...please, I'll do it whenever you want!" Ashley begged. She tightened her leg, squashing his neck under her knee. His cock twitched, getting even harder.
"You do that anyway, dummy." She sighed in disgust. Keeping him pinned with one leg, she raised the other, until her bare foot hovered right in front of his face. Ashley stared at it in confusion, watching her pretty toes wriggle about. She was wearing red nail polish today. "Kiss my foot, idiot, while I decide if it's even worth keeping you around." Cathy snapped at him. The young warlock bent in hurriedly, and started kissing the skin on the top of her foot. It wouldn't be so dirty there and hopefully she'd be satisfied with that. "Toes too, dummy." So much for that. Ashley craned his neck, struggling to even move with her leg wrapped around him. He started kissing the tops of her toes, his cheeks so hot it felt like they were about to burst into flame. Blushing was fine, but at the same time his dick was aching even more inside his panties. He didn't enjoy this, he didn't! "You're so pathetic." Cathy sneered. Her foot darted down to push him on his chest and he fell onto his butt with a high-pitched squeak of shock. "I kind of feel sorry for you, that's the only reason I'm not going to ruin your life. You clearly deserve it."
"Cathy..." Ashley began miserably.
"Shut up!" She snarled at him, and his lips snapped shut, trembling in fear. "Your mouth's only good for one thing and it isn't talking. Fuck, you just don't get it, do you? You're a pervert, a pathetic little waste of space who deserves to have everyone know he's a panty-wearing sicko. Otherwise you'd probably be off stealing from the girls locker room and sniffing away. Isn't that right, little perv?" Ashley paused, staring up at his girlfriend with tear-filled eyes. She wouldn't make him say that, would she? Cathy just glared back down at him. Her lips were wet and parted, and there was a slight flush to her pale cheeks. Was she...enjoying this? Then her eyes flashed, and he knew he had to say something before she got even angrier.
"Yes." The young warlock nodded miserably.
"Not good enough, dummy." Cathy breathed, her voice hot. "I want to hear you say it, properly. What are you, Ash?"
"I'm a pervert." He sniffled, tears dribbling down his cheeks. Her eyebrow darted up, and he knew she wasn't satisfied. "I'm...a disgusting, panty-wearing sissy who deserves to be bullied." His voice died in a strangled, painful sob. Her forcing him to say these things was awful enough, but there was a part of him starting to think every word was true. Maybe he really was disgusting. It was wrong for a boy to wear pretty panties and enjoy it so much. Maybe he did deserve to get treated this badly. After all, everyone in his life was just awful to him. Everyone but Abaraxes.
Cathy paused a moment, glaring down at him with hooded blue eyes. As he watched miserably, his girlfriend licked her curled lips. Then she relaxed back into the chair, smirking down at him like a queen on her throne. She stretched out her legs again, wrapping her feet round his sides and squeezing in. For someone who was so disgusted by him, she seemed to like touching him a lot.
"You're in luck, Ash." She purred, sounding like a hungry cat. "I think I might just have a use for you, something that should make putting up with you worth all the fuss. I'm going to take you on a date."
"What?" Ashley glanced up, stiffening in shock. A real date? He called her his girlfriend in his head, but the past week the only thing they'd done together was him eating her out and then being forced to take all those embarrassing photos.
"Don't get too excited, dummy." Cathy sneered. "It's a one-time thing. See, there's this party I've got to go to on Friday. Everyone I need to impress is gonna be there. Problem is, I know my fucking bitch of an ex is coming too. So I can't show up alone. It'd be pathetic. She'll think I'm not over her." Ashley figured by the venom in his girlfriend's voice, she definitely wasn't over this ex, but kept his thoughts to himself. "If there was anyone else I could ask, I'd be there, but fuck, there's hardly any lesbians in this town as it is. Then I remembered you, Ash. You are free on Friday, aren't you?" Her legs tightened, giving him a firm squeeze between them.
"I...um should be." Ashley admitted, squirming at the uncomfortable pressure on his sides. A party, that was new at least. He'd never been cool enough to go to a high-school party before. And his super-hot girlfriend had invited him. That had to mean something! Maybe she was going to be nicer.
"Good." Cathy smirked. "It's a girl's only party, so I'm going to need you to wear something cute. I want you looking pretty, Ash. The girlier the better, that way no-one will guess your actually a boy." Ashley's heart sunk more and more with each word.
"Cathy...please I can't do this in public." He stammered. There had been that one time in the mall but Abaraxes had been with him then.
"Shut up, idiot." His girlfriend snapped, her legs tightening around his sides. He let out a strangled whine as her muscles squeezed him. "These girls all know I'm gay. How's it going to look if I show up with some prick hanging on my arm! They've got to think you're a girl, okay? Otherwise you're not getting in at all, and then I can't make my bitch ex jealous. If that happens, I'm going to be so fucking furious I'll have to take it out on you." The young warlock whimpered in pain. She was definitely serious, and millimeters away from crushing him between her legs. Better not to argue. "In fact, I don't even trust you not to fuck this up. I'll be coming by at nine tomorrow, and you'd better be there to greet me at the door wearing a cute pair of panties and nothing else."
"What?" Ashley gasped.
"You heard me, dummy." Cathy sneered. "I don't want to see you wearing ugly boy's clothes. It'll throw me off before the party, and we can't have that. You'll meet me wearing only panties, just like I want. Then I want you to get dressed in a nice girly outfit so I can see if it's suitable. Once I've picked one, I'll put on your makeup for you too. You've been getting lazy with that and it stops now, okay Ash?"
"Yes Cathy." The young warlock whispered, too miserable to even argue with her. It didn't make sense to him. Why couldn't he just get dressed first and then meet her at the door? It was like she was purposefully trying to humiliate him.
"Good." Cathy sighed. She rose to her feet, standing tall above him. "Then I guess we're done here. How about a goodbye kiss before I leave, Ash?" Ashley tried to scramble up, only to freeze as her hand landed on his head. "Not like that, dummy." She smirked. "Where do you kiss me?" Her bare legs spread apart and the young warlock felt his stomach sink. He lent forward and gently placed his lips on top of her wet pussy.
With a cold laugh, she stepped back and pulled on her underwear and jeans. Ashley watched, kneeling on the floor in pretty pink panties, as the girl he'd thought he was in love with for years turned and strode away without another word to him.
She'd changed so much. The Cathy he remembered from when they were kids was sweet and kind, always hanging out with him when no-one else would. Sure, she used to make him fetch stuff for her, and there were a few times he'd been forced to run around on all fours as her pony while she rode his back and kicked him, but she hadn't done anything much to hurt him.
Now he realized how dumb he'd been to think she'd be just the same as back then. They'd barely exchanged a word since they started high school, but he'd somehow ended up believing that if got her to notice him she'd be his sweet, kind girlfriend and do everything his way. Fuck...he hadn't even realized she was gay. Made sense he wouldn't know she'd turned into a mean, selfish bitch either.
Ashley let out a hoarse sigh and rose to his feet. He picked up the pink t-shirt he'd been wearing when Cathy arrived, blushing faintly at the glittery lettering on the front. Daddy's little princess it read. Why the fuck did he even have this? Abaraxes of course, the beautiful succubus had chosen all his girly outfits for him and he could only imagine what she'd been thinking when she'd picked this one.
The young warlock bit his lip, just the thought of the demon he'd summoned making his chest all tight and sore. He wished she was still here. She was really smart...she'd be able to think of a way to get Cathy off his back. After all, she'd helped him so much in just that lovely day or so they'd been together.
If only he could summon her again, but he'd returned the Librum Maleficarum to that weird old pawnshop like she'd told him to. A couple days ago he'd gone snooping back around the place, just to check, but the book had been gone. He'd even found the courage to ask the creepy storekeeper about it but the old guy had acted like he'd never seen such a thing before. Sighing to himself, Ashley went for the stairs, deciding it was time he get ready for another long night alone.
Later, when he'd washed the pussy juices off his face and got his girly clothes all neatly folded in his wardrobe, Ashley was still thinking about the succubus. Wearing only his pretty, pink panties, the way he spent most nights these days, the young warlock lay back on his bed. His tiny cock was aching hard, and every time the head brushed against the soft silk of his underwears he shivered and blushed even hotter.
His hand wandered down between his legs and he tugged the panties down a little. Just enough to free his stiff little dick, while keeping his butt and thighs wrapped in soft silk. A girly moan of pleasure escaped his lips as he grabbed it between two fingers, rubbing and squeezing along the length. His fantasies were the same as they had been this past week. Even though he'd spent an hour today eating out his really hot girlfriend, all he could think about as he tugged his dick was Abaraxes.
Ashley imagined the gorgeous succubus towering above, with him kneeling meekly at her feet. At a word from her, he'd bury his face between her toned thighs and lick her gorgeous pussy until she trembled and moaned. It wouldn't be like Cathy. She'd run her fingers through his hair and tell him what a good boy he was. Her hands would cup his cheeks or rub his forehead, reassuring him, letting him know that she liked him. Maybe she'd even teach him just the right way to please her, in that kind, gentle way she'd told him how to eat out a woman in the first place.
After he licked her to a few nice orgasms she'd smile at him and pull him to his feet, and then they'd kiss properly, making out with his body pressed against hers. She'd reach down with one hand and rub his cock for him, because she cared about his pleasure too. Her fingers would feel so good...just to have someone else touch him there for the first time in his life. As she smiled and held him, he'd cum across her gorgeous muscled belly.
"Good boy, Ashley." He heard her coo, right in his ear, her sultry voice filled with delight. His nose wrinkled with the faint scent of sulfur, but before he could even wonder what was happening he felt his legs start to shake and white heat flooding through his belly.
"Oh, Abaraxes!" He squealed, thrusting his hips. Warm cum dribbled over his fingers. There wasn't much, and it was all thin and watery like always. He frowned slightly, staring at the pearly drops clinging to his skin. That was strange. For a moment there he'd really been convinced she was in the room with him. And that smell too. Sulphur, just like when he'd summoned her. Well he couldn't smell anything now. It must just have been his imagination. Blushing and panting, he went and wiped off with a tissue, then fixed his panties, pulling them nice and snug over his pale hips.
A quick glance in the mirror made him shiver. It wasn't that he looked silly wearing such pretty underwear, like most boys would. Quite the opposite in fact and that was the problem. The soft fabric clung to his butt, each plump cheek pressing tight against the silk. At his thighs, the pretty pink seemed to match perfectly against his pale skin. He really did look like a girl. A pretty girl wearing her panties to bed. Why did he like that? What the fuck was wrong with him?
Maybe Cathy was right and he was just some sick, filthy pervert. Only he couldn't quite believe that, no matter how many times his girlfriend told him so. It was Abaraxes who'd shown him how to look pretty like this. The succubus had done nothing to hurt him. She liked him...she'd tried to protect him from his own stupidity. If this really was wrong, then she wouldn't have taught him about it in the first place.
He smiled to himself, twisting and turning in the mirror. His cock was already twitching to new life and he shivered as it pressed against the soft silk. Sure, things were bad right now, but he had to stay positive. Cathy would get bored of him eventually, she had to. Then she'd give up and go back to her friends and he could just fade into the background the way he did best. Maybe if he kept looking he'd even find the Librum Maleficarum some day, so he could see Abaraxes again. She'd told him not to but surely she wouldn't get mad if he just wanted to talk to her?
A quick glance at his alarm clock made him jump back into bed. Eleven-thirty, just when Abaraxes had told him that first night he needed to be asleep. Even though she was long gone, back to whatever place she called home, it still felt like she was watching over him so long as he was good and did like she'd said. So long as he was a good boy in his pretty girly clothes...just like she wanted.