Cupid's Mess

*** Cirrus ***

It is, like every year, complete pandemonium. That's what happens when you try and cram every single cupid in the entire world into a single amphitheater, even one as big as the one on Olympos.

First of all, there are a lot of us, and second of all, we have wings. Giant, white, feathered wings that are incredibly fun when you're soaring through the air but are very cumbersome when you're supposed to squeeze shoulder-to-shoulder into rows that can't even accommodate a centaur. And bows. And a quiver.

It is February 13th and tomorrow is the biggest event of our lives. Months of rigorous practice and years of training all lead up to the competition. The excitement in the air is palpable. Valentine's Day. The big one.

A bright light flashes on the dais in front of us and Venus steps out of thin air. My heart skips a beat at seeing perfect beauty, naked and plump. My pulse quickens and all around me, I hear gasps. Bodies shift around. Wings unfold. Everyone is teetering on the edge of their seats.

"Welcome, my lovelies," Venus speaks and her voice is like a kiss in my ear. "Tomorrow is an important day."

All the discomforts of the amphitheater evaporate and it is just me and her, the Goddess of love and beauty. I drink in the sight of her, those shimmering, radiant eyes and delicate nose. The voluptuous breasts, ripe with nectar. The valley of mortal and immortal pleasures whose entrance is hidden by a forest.

"Valentine's Day," Venus says and I shiver at the raw eroticism with which she pronounces the word. "The day we commemorate my first cupid lover."

Everyone knows the story, of course. I've heard it a million times, at first just in hushed whispers late at night from giggly mouths, but then once training started, our instructors told us practically every day. It is what we are training for, of course.

To become Venus' new lover for an entire year. Valentine was the first one, a particularly daring and charming cupid that fell in love with Venus and pledged to show her that cupids were the best sexual partners in the entire pantheon.

To make a long story short, because quite frankly I'm sick of retelling the same story over and over, they boinked. Venus must have liked what she experienced because after Mr. Valentine turned to the stars, she began to take more cupid lovers.

One special cupid to become her lover for an entire year. It is supposed to be an unforgettable, incredible experience. Unfortunately for the rest of us, also an indescribable experience. One of my teachers had the honor and every time Octavia started to even think about her time with the Goddess, her eyes glazed over and she began drooling.

Fifty years of back-breaking training until we are adults and are allowed to take part in the annual festivities. It is my second time and I'm determined to win this time. Then again, so is every other cupid. And, as I said, there are a lot of us.

"...but only one of you will succeed," Venus finishes.

I blink. While daydreaming about her divine body, I must have missed most of the speech. Again.

"Go. Fly. Fill the world with new love," she calls out. "Pure love. Good love."

All around me, cupids jump to their feet, and wings feather out. There's not enough room to take off and I'm being pushed around from all sides by sweaty bodies and fluff. We have to wait for those at the edge to fly first but everyone is impatient.

Hundreds of cupids take to the air at first. Then it is thousands. By the time I unfold my own wings and finally feel the clean air rushing through my hair again, it is tens of thousands. I turn around in the air one more time to get another look at Venus but the dais is empty already.

The only way I'll see her again before another year has passed is if I win. I sigh and flap my wings to speed up. It is a long way back to America.

*** Cirrus ***

The sun hangs just above the horizon but the people are already out and about. A mile below me is the Centerville Mall. I can feel the hundreds of people. Families, friends, couples. More than a few lovers — I can sense those the strongest — eager to spend Valentine's Day in each other's arms.

"Wait up, Cirrus!" Maximus shouts from behind me.

Groaning, I slow down. Maximus is not someone I'd call a friend but nevertheless, we spend a significant amount of time around each other. He is one of the other cupids working in the same region. An older, better, and stronger cupid. Someone I wouldn't want on my bad side, no matter how annoying he is.

"Do you have anyone yet?" he asks once he is caught up.

"I'm not telling you anything," I say because I definitely do not have anyone yet.

I spent weeks trying to find the perfect pair to bring together. Something grand that would get Venus' attention. Bringing two enemies together, like Romeo and Juliet, or launching one of the great wars, like Helen and Paris. We all know the famous ones that earned a cupid a year with Venus.

Except this is Centerville, a tiny city of twenty-thousand in Suburbia, America. Not Tokyo or New York or Johannesburg.

"I can tell you have nothing," Maximus shouts and laughs.

"Sounds like you don't have any idea either and just want to steal mine. Again."

Last year, I bragged to everyone about how I was going to win my first year. I found the perfect people, two women that had been best friends in high school. Both had boyfriends that they weren't happy with and came from very conservative families but they always felt that undeniable attraction between each other that they never spoke of. Then high school ended and one of them moved out of Centerville.

It had taken weeks of planning. Carefully maneuvering Amy to feel the pangs of nostalgia. Prodding Cynthia to finally break up with the guy who's been cheating on her. Getting them both into the same cafe at noon on February 14th.

And then Maximus shot his arrow while I was still waiting for the right moment. He claimed he was just passing by on chance and had sensed the amazing opportunity. Acted without thinking. He apologized over and over but I know he did it on purpose.

At least he didn't win.

"I said I'm sorry," Maximus says halfheartedly. "You don't have to worry about an accident this year. Not unless you're going after one of the Impossibles, too."

"The Impossibles?" I ask.

"Yeah, you know. The people that cupids have tried to bring together for years and always fail."

"Arrows don't fail."

"Tell that to the Impossibles," Maximus chuckles. "There's actually one of them right here in Centerville, that's why I'm here. I'm going to finally bring them together and Venus has to pick me. It's been at least two-hundred years since someone managed to bind an Impossible."

"Bullshit."

"Don't believe me? See for yourself."

Maximus rolls forward and dives toward the mall, wings flat against his body. I pull in my wings and begin a breakneck descent after him. Just before hitting the roof, Maximus unfurls and slowly descends through the concrete.

"There," he says in a whisper, though no human can see or hear us.

It takes me a few moments to spot the two people he is pointing at in the crowd. A man and a woman, walking side by side. I reach out with my senses and immediately I can tell there's something different about them. They know each other well, more than friends but not lovers. He is single and she is single. There is some sort of bond between them already, enough for an arrow to work.

"It doesn't feel like it's impossible," I say.

"That's because you are barely an adult, fresh out of school," Maximus says and grins haughtily. "Trust me, I watched half a dozen cupids try to arrow them last year and every single one of them missed."

"Cupids can't miss."

"So young and naive," Maximus chuckles. "Try it if you want."

Something about his confidence makes me have doubts.

"You said you were going to. I don't want to steal your mark, I'm not that kind of cupid."

Maximus rolls his eyes. "Believe me, I'm not worried. I have been practicing all month and I'm gonna follow them all day for an opportunity to bind them. You can't just waltz in here unprepared, fire off an arrow, and bind them. There's a reason they're an Impossible, I haven't even been able to sense a mark in their bond."

Impossible my ass. Ever since I reached out with my sense, I've felt the bond between the two of them as plain as the sun. Even now, the mark is there, though I have to admit it is very faint. But it's there.

And if I can sense it and he can't then maybe I can also bind them. I can bring together an Impossible, the first cupid in two-hundred years. A year with Venus. Those wonderful legs!

Without thinking about it, I raise my bow and retrieve an arrow. I pull the string taut and nock the arrow. My muscles ache but I have to concentrate to find the mark again. Such a small, faint target on such a strong bond. It is quite odd.

I loose and the arrow sings as it flies through the air.

Bullseye.

"That was easy," I say smugly.

Maximus begins to laugh. I turn toward him, confused. He is laughing so hard he has tears in his eyes. Something is wrong but I don't know what.

"The... reason..." he says between wheezing laughter, "they're... impossible... is... because... because... because..." Maximus stops to cough. His face is all red and he claps me on the shoulder. "Because they're mother and son!"

Oh, shit!

Panicking, I extend my senses again. The bond between them is rapidly growing, mutating into something much bigger and stronger. I can see now what I missed earlier. Yes, they're both single but the guy is a lot younger. He's in his early twenties and hormones are still raging in him. The woman, however, is much older. About nineteen years older, though she looks much younger.

"I can't believe you did that," Maximus laughs again before unfurling his wings. "See ya later, loser. I have a date with two sets of triplets that are just perfect for each other."

Shit, shit, shit!

I look at the two of them, mother and son, and sense the bond mutating and growing.

*** Gabe ***

How had he managed to live twenty-one years without ever truly realizing that, well, his mom was a woman? Not just a sexless mother, a dutiful parental unit without any distinct genitalia, who only once in her entire life had sex on a very abstract level to produce him.

But one single accidental glance changed all of that.

They had gone to the mall together, something they haven't done in ages because he needed to pick up a few items for his Valentine's Day date and wanted to borrow the car. She said she needed to go, too, and off they went.

Of course, he didn't tell her that he needed to buy condoms and lube, just something about "school accessories." His girlfriend of one week, Kayla, had hinted strongly that he was going to "get lucky" tonight. He was pretty sure that she was only dating him because she got dumped two weeks ago and didn't want to be alone for Valentine's Day, but if the night ended in sex, he didn't really care.

So when he met up with his mother again to head home, his mind was firmly on sex. The twenty-four pack of condoms felt a lot heavier than it should have and he made absolutely sure that his mother wouldn't see it, always carrying the bag on the side opposite her. It was just an accident really that when he thought he heard a noise and looked around to see what it was, he caught sight of a flash of gold-on-pink.

Inside his mother's creme tote bag was an item with the logo of the infamous Sam's Boutique, the place that only sold things women bought when they wanted to seduce guys. Sexy underwear, risque dresses, and other items that someone wouldn't wear in public.

Gabe's heart started beating faster and his brain went into overdrive. He couldn't help it, as much as he wanted to. He pictured his mother, who was theoretically very beautiful, wearing pantyhose, garter belt, and a bra so sheer he could see her nipples and transform into actually very beautiful. No, that wasn't the right word for it. Actually very hot.

And that's how he came to spend the entire twenty-minute drive back home fantasizing about his mother's sex life.

Does she have a date, too? Does she even date at all? Thinking back, he can't remember a single time she told him about a date in the ten years since his father passed. It just never occurred to him that she might want that. That she, too, has a sex drive.

Maybe she doesn't. Maybe she hasn't had sex the entire time, too busy taking care of him, even though he's been going to college for three years. He still lives at home because it was so much cheaper and they didn't have a lot of money to spare, so she never had the opportunity.

After ten years of celibacy, she is going to start dating again on Valentine's Day. He imagines her putting on Sam's Boutique underwear, dressing up, going to a nice restaurant, and meeting up with some guy.

Some guy! Putting his dirty hands on his mother's tits. Pressing his lips on her mouth. The two of them, naked in bed. Fucking his mother, his cock plunging into her wet pussy, over and over and over.

Gabe doesn't realize what he is doing until he cums, blowing his load on his t-shirt. A powerful, balls deep orgasm that makes his entire body tingle.

A few seconds later, his brain kicks back in. He looks around and fortunately, the door to his room is closed. The mess on his stomach is bigger than it should have been and no way to easily clean it up. He gets up, wipes his glans on a bit of t-shirt, and gets a fresh one from the dresser.

What the hell happened to him? In less than six hours, he has a date with a very pretty, very slutty chick and he just jerked off while thinking about his mother. It is pathetic and weird. But even now, thinking about his mother makes his penis twitch.

Is she going to spend the rest of the day preparing for her date? How would she go about that? Does she shave? The thought of his mother spending the afternoon in the ensuite, one leg up on the bathtub, legs spread wide, shaving her pussy makes him hard again. Not just sex to fulfill a bodily need, no, it's because she's turned on by the sight of a hard cock between her bare lips.

Creeping on tiptoes, Gabe leaves his room and traipses across the hallway to his mother's bedroom. The door is closed. He presses his ear against the wood and hears the faint sound of water splashing against tile.

She's taking a shower.

Heart thumping in his chest, he turns the handle and pushes open the door. The scent of his mother envelopes his nostrils and he takes a deep breath. The non-descript tote lies on the duvet. In two quick steps, he reaches the bed and grabs the bag. It's empty. Disappointment washes over him.

Of course, that would have been too fortuitous. She probably has it with her in the bathroom, ready to wear it when she's done showering.

Carefully, Gabe makes his way to the ensuite's door. Just on the other side of the one-inch thick wood is his mother, hot water running down her naked body. Rubbing shower gel over her tits. Lathering up her ass.

Madness grips him and he grabs the door handle. Turns. Pushes. And it's locked.

Then he hears a faint sigh or moan coming from inside the room. It's too much, he can't hold back anymore. He unbuttons his jeans and pulls out his hard cock. He starts jerking with a ferocity that makes his still-sensitive penis scream — in a surprisingly good way.

A few seconds later he comes and his seed splashes against the door. At the same moment, the water turns off. Realizing just how terrible it would be to be caught with his pants literally down, Gabe hurriedly wipes his cum off the wood with his t-shirt and exfiltrates.

Another t-shirt ruined.

*** Marie ***

Everything in the universe seems to be conspiring against her on this Valentine's Day like it is trying to tell her to just give up already. It's not like she had much going for her in the first place.

Ten years since her husband passed so suddenly. Ten long, miserable years. No one expected her to start dating right away and she didn't. It was only after two years that her friends started pushing guys on her and whispering behind her back. She gave in eventually, she was only human.

It all tantamounted to nothing. A few dates here and there with boring guys, a handful of week-long relationships that fizzled out, about a dozen one night stands scattered through the years.

Who needs a guy when she can just get herself off whenever she wants? Except that's where the problem started. Her grand plans for Valentine's Day were to just snuggle up in bed with a bottle of wine and Mr. Battery, trying her best not to contemplate her solitude.

Except the night before, her vibrator broke. Not just a matter of replacing batteries, she tried a dozen of them, but an honest-to-God mechanical failure. She'd ridden the poor thing so often and so hard that it decided to off itself.

How pathetic she must have looked to the cashier of Sam's Boutique, buying a vibrator on the morning of February 14th. She is an adult woman who doesn't need to justify her behavior or her purchases to anyone but putting the box of the "Clit Obliterator" on the counter made her feel like she was doing something illegal.

The cherry on the misery cake is that her son needed to go to the mall to buy condoms for his date. He thought himself so clever, always making sure the bag was out of sight, but he failed to realize that the bag was slightly transparent. Seeing a partially opaque cartoon of a bright green cartoon dick was enough to figure out what was inside.

Gabe, of course, has a date for Valentine's Day. A little slut named Kayla. Marie had never actually met her in person but she caught sight of her once when she picked up Gabe in the evening. Pretty, the way twenty-year-olds were, but very handsy. She had stopped watching when the two of them started to make out in the car.

They are going to fuck and, for some reason, she can't stop thinking about it. It was like seeing the box of condoms in his possession made it click inside her head that her son isn't her little baby any longer. Gabe is just at the same age as his father when she first met him. If you put pictures of the two of them side by side, they'd look like brothers.

Where will the two of them do it? If he resembles his father in more than just looks, he is undoubtedly just going to drive the car somewhere out of sight and then just mount her there. Yes, she is sure the little slut would be up for that, too. He'll lean back the seat a little while she unzips his pants and slides a condom over his powerful cock. They won't even take their clothes off, she'll just straddle him.

The drive home from the mall leaves Marie with her panties drenched. She accidentally plows through a stop sign, imagining Gabe fucking Kayla so hard her ass keeps bumping into the horn.

Honk-moan-honk-moan-honk-moan.

As soon as she sets foot into the house, she runs upstairs, pulls the Clit Obliterator out of the tote, and locks herself in the bathroom. The new vibrator, as the name implies, has an attachment just to stimulate her clit. Compared to her old one, it was basically a high-tech gadget. She inserted a fresh pair of batteries and twisted the base. It came alive with a loud, powerful buzz.

Eagerly stripping out of her clothes, she runs the shower so that it will drown out the buzzing of the vibrator. She looks at herself in the mirror, wishing that still had the body of a twenty-year-old. She sits on the carpet, spreads her legs, and runs her fingers through her pubic hair, gently probing her entrance. Her finger comes back wet, a tendril of mucus clinging between it and her labia.

Placing the tip of the vibrator at her hole, she is immediately transported back into the car. Not her own car, but rather the imaginary car that her son and Kayla were fucking in. Only now it's she who is straddling Gabe. It's her pussy that her son's big, hard cock is plunging into. It's her ass that's slamming into the horn, over and over and over.