The Cupid's Arrow Challenge

(Contains male masturbation, magical female chastity, pegging, mind control, dubcon [for both participants], and general silliness. For the reading pleasure of interested adults only, not to be taken seriously.)

***

Evan knew what he was doing was wrong.

He knew it while he was rolling up the rose petals in the cigarette wrapper and twisting one end into a point.

He knew it while he was trimming the dove feathers and attaching them to the sides for aerodynamic stability, just as the viral video had instructed.

He felt it most keenly while he whispered the incantation to the little paper arrow in his hands.

"Make Michaela want me, so badly she can't help herself. Make her see everything she's ever wanted in me, and only me. Wake her with lust at the stroke of midnight on Saint Valentine's Day. Allow her no rest or satisfaction until she comes to me to get it. Let nothing, not distance, nor physical obstacles, nor morals, nor law, stand in the way of her newfound desire for me. Mighty Cupid, lend me your power."

Everyone was doing the "Cupid's Arrow Challenge" this year, Evan assured himself.

Besides, an ounce of paper, petals, and feathers, all held together with sticky tape, designed by some unidentified TikTok user enjoying their fifteen minutes of fame, wasn't really going to override anyone's free will.

No, this was just a bit of fantasy play for himself, maybe even a much-needed exercise in turning thoughts into action.

After practicing with a silly little action like this, maybe he could build up the courage for something more responsible and useful, like actually asking Michaela out for coffee.

In the meantime, his foolishness wouldn't affect her in the slightest.

This was what he told himself when he slipped the arrow into the pocket of Michaela's jacket, as they shared an elevator down to the parking garage after work on February 13th.

"Mighty Cupid, lend me your power," he whispered once more under his breath, completing the challenge.

#

That night, Evan lay awake, counting down to Valentine's Day like a kid counting down to Christmas, almost convincing himself to believe in magic.

At midnight, he imagined Michaela waking up, breathing hard, with her shiny brown hair cascading all over her shoulders. It would lose its artificial straightness and turn wavy as it absorbed the sweat dripping down the back of her neck.

She'd be confused, at first, to suddenly experience such an intense, sexual dream about Evan, a quiet coworker she barely knew. Most likely, she'd try to go back to sleep and forget the whole thing.

When that didn't work, she would touch herself. She'd use the dream, and all her passing memories of Evan, in a way she'd never imagined she would. Hands working furiously under the covers, she would try to turn those thoughts into secret pleasure and relief.

When that didn't work either, that was when the fun would start.

She would probably try for a long time, Evan guessed. He would, if it were him.

Each passing moment would add to her confusion, turning it to panic. She wouldn't understand what was wrong, how she could possibly be so aroused and yet unable to cross that last threshold.

But part of her would know instinctively, magically, what she had to do about it.

She would trade the warmth of her bed for the cold night outside, and come straight here, without even taking the time to change.

Evan could see her in his doorway, in a pink satin nightie and dramatic matching dressing gown, falling to her knees and begging him to take her in and fuck her without delay.

He would be shocked to see her, of course. Nobody could have expected that ridiculous Cupid's Arrow Challenge to work.

In fact, who was to say that it had? Maybe it was a coincidence that Michaela's lust for him had surfaced that night. Or maybe it was just Valentine's Day in the air, and the idea of the challenge circulating online, that had prompted her to tap into her latent desires.

No reasonable person could hold Evan responsible for that.

And in any case, now that she was here, pleading for his help to ease her discomfort, he couldn't just turn her away to suffer, could he?

Evan was rock hard thinking about it. He played with himself periodically, just one or two quick touches at a time, holding back. He told himself it was to prolong the experience, to simulate the deprivation the Michaela of his dreams was going through, so he could imagine it all the better.

Truthfully, he was saving his pleasure, on the ridiculous, impossible chance that Michaela really was on her way here to share it with him.

At around two in the morning, the fantasy began to fracture around the probability that she was fast asleep and not thinking of him at all.

Deciding it was time to wrap things up, Evan began stroking himself in earnest, trying to hold onto the image of Michaela begging for his touch for just a few more minutes.

Just before he could reach his own orgasmic threshold, his whole apartment shook with a forceful knock at his front door.

#

"Evan!" That was Michaela's voice, all right, shouting his name with breathless urgency. "Evan, let me in!"

"No... fucking... way," Evan breathed as he approached the door in his boxers, grabbing a cushion to hold in front of his pulsing erection.

The hair along his arms and back stood on end with cold, with excitement, and with a significant tinge of fear.

Wishing for a magically love-mad Michaela to be delivered to his doorstep was easy. Knowing what to do when it actually happened — that was suddenly feeling a bit above his paygrade.

He opened the door.

Michaela's eyes were as wild as he had pictured them, but not nearly as confused. In place of pink satin, she was wearing a tattered t-shirt, and instead of falling to her knees, she leapt on him, kissing his mouth and biting at his lips until he kissed her back.

I'm kissing Michaela, Evan thought to himself, trying to relax enough to take in the warm, earthy taste of her skin, the soft and firm parts of her body curving into each other, details he'd only been able to guess at before.

Thinking the words didn't help the kiss make sense.

"Happy Valentine's Day, my love," she murmured, moving her lips to his ear.

Outside, Evan could hear running, shouting, far more activity than was usual for his neighborhood at this time of night.

But then Michaela was pushing him deeper into his studio apartment, shutting the door behind herself, and he knew he had closer things to wonder about.

Like what she was carrying in that gift bag, with the hearts all over it.

"I'll be honest," said Michaela, stepping deliberately forward, herding Evan closer to the bed. "I never thought much of you before. I mean, sure, I thought you were cute, but you never struck me as the type who could handle me, give me what I wanted."

She pulled the modesty cushion from his hands and tossed it aside.

"And, uh, now?" Evan stalled to think, lunging to put the island of his tiny kitchen between them.

"Now I know the truth," said Michaela, leaping onto the island with inhuman agility, sending Evan's dishrack crashing to the floor.

She stepped gracefully back onto the floor right beside him. Her closeness made his skin tingle, just like in the elevator.

"It was a bolt from the blue," she said fervently. "One moment, I was blind, and the next, I just knew who you were. You're everything I've ever wanted. A man who truly wants me to fuck him the way I want to!"

She reached through the tissue paper of the gift bag and pulled out a pastel-pink dildo and harness. Apparently in honor of the day, the dildo's head was shaped like an upside-down stylized heart, and a larger, matching heart hung from its base in place of testicles.

Evan's actual heart burst into a sprint.

"Michaela," he raised his hands to signal for space and found her pressing her breasts into his palms instead, nipples hard and obvious under her t-shirt. "There's something I should tell you."

"Shh, it's okay if you didn't get me anything," she told him, buckling the harness over her plain white panties. "My gift's really for both of us."

She pulled the straps tight, so that the dildo rose up to tap heads with Evan's flesh and blood erection, which had not softened.

"It's not that," said Evan, backing away another step. "You're not thinking clearly, and that's my fault. I—"

"Are we talking about this?" Michaela retrieved the paper arrow from the bag and held it up for him. "I know, I should be upset with you for this."

She dropped it back in, smiling in spite of herself.

"When I found it in my clothes, I took it the way most people would. As a threat. But that was before I realized it was from you. My true love. My perfect bottom, making himself known. With how much good your little spell is going to do both of us, I barely even want to spank you for it."

"See, that's the thing," said Evan, taking the head of her strap-on gingerly between his fingers and angling it away from himself. "I'm not really the guy you think I am."

At this, Michaela did look confused, for the first time since she'd arrived. Doubt infiltrated her smile. Then her eyes glazed over, the spell disallowing such thoughts.

She shook her head, resetting her eyes and smile to their starry eagerness.

"Of course you are, silly. You're the one I can do this with. The only one."

She reached into the bag again, this time for a strawberry-colored tube of lubricant.

Evan decided it was time to take a firmer stance. He grabbed Michaela's hands, meaning to stop her from opening the tube.

Effortlessly, she pulled one hand out of his grip, planted it on his chest, and shoved him away.

"I can do this part myself," she chided him.

The shove was only playful, yet it felt as if it had come from a pneumatic piston. No soft-bodied woman — no human being of any build — could have produced such controlled yet irresistible force without even shifting their weight.

As Evan watched her apply the lube to the strap-on, the weight of the magic sunk in.

He really might not have any choice left in this.

While Michaela checked for dry spots, Evan ran to his bathroom, closed the door, and locked it.

Not two seconds later, Michaela ripped the door off its hinges, as easily as she might have opened it if it were unlocked.

"What are you doing?" she asked, with that genuine confusion again.

Before Evan could turn a series of panicky gasps into an actual answer, Michaela's face brightened.

"Oh, this is part of it, isn't it?" she clapped her hands. "You're going to playact some reluctance for me. How did you know? Right, of course you would know all my fantasies. You're the one."

"No, I'm not!" Evan blurted out.

"Right, right." Michaela passed a hand in front of her face, getting into character. "Better move it, mister. You're taking it in the ass tonight, whether you like it or not."

She spoke with fake sternness, but yanked him toward the bed with very real force.

"Michaela, please," Evan begged as she pulled down his boxers, unhooking them from over his sore, persistent erection, and bent him forcibly over the side of the bed.

For a passing moment, Michaela seemed to comprehend faintly that there was some genuine anxiety shuddering its way through Evan's muscles.

"Pretend that guilt and shame don't exist for a moment," she whispered to him. "No context, no input from anyone else, or from whoever you thought you were supposed to be."

She pressed the heart-shaped head of the dildo against his hole, and reached under him to wrap her lube-coated hand around his cock.

"Does what's left of you want this?" she asked.

In her spell-addled state, Michaela clearly thought she knew the answer already.

Only Evan was surprised when he nodded.

This was nothing like how he'd pictured it, but here he was, in bed with Michaela, horny as hell and about to provide her with her favorite hard-to-get pleasure.

If he'd had the power to undo the Cupid's Arrow Challenge right now, he would have done it for her sake, but not his own.

As Michaela pushed her pink, plastic tool into Evan, both the pain and pleasure shocked him with their intensity.

His body fought involuntarily against the hard intrusion, but each failed struggle echoed back along his nerves, sizzling through his skin, prickling his scalp, setting off pre-orgasmic muscle contractions.

The pain mostly receded after a few moments, but the pleasure did not.

Michaela fucked him firmly, decisively, the magic making her confident in his enjoyment.

Maybe it wasn't all the magic. Each unstoppable thrust of her hips also rubbed his cock against her hand, letting her observe some of his enjoyment directly.

She paused only to slide her other hand behind the strap-on, to touch herself.

"I can't tell you how long I've waited for this night!" she moaned. "I just never imagined you would let me do this."

"I know... what you mean," Evan grunted beneath her. "Oh... god."

It didn't take long for him to cum in her hand. Once he had, she kept him pinned there in his mess, fucking him just for the thrill of it, and because she couldn't finish without involving him.

Cupid's arrow had seen to that.

When she finally reached the screaming climax he'd been keeping from her since midnight, she pulled out and threw herself contentedly on the bed beside him.

As the pleasure daze faded out of her eyes, so did the magic.

Looking back on the night with a clear head, Michaela's expression shifted from content, to horror, to anger, to embarrassment, to guilt, and back to anger.

"I'm sorry," said Evan blearily. "I didn't know it was real, and then I couldn't stop you."

Next came pity, then more horror, more embarrassment. Far too many things to unpack tonight.

Michaela unbuckled the strap-on, left it on the bed, and opened the door, letting in more distant sounds of shouts, moans, breaking glass, sirens —other Cupid's Arrow Challenges in progress.

"I..." Michaela started, then shook her head. "I'll see you at work."

For their office and plenty of others, it was a very quiet Valentine's Day.

***

Happy Valentine's Day! If you had a good time, show me some love with your favorites, comments, and/or follows!