The Shittiest Princess and the Friendzone

The Shittiest Princess is a series of funny fairy tales for those of us who ain’t exactly cartoon princesses. Stay tuned for a new adventure every week!  You can find the whole series here.

In the dankest depths of the darkest month of the year, Blorgvember, happened the most horrid holiday this side of a dirty cat butt: Valentine’s Day. Everything awful in Kingdomville occurred in Blorgvember, unless you were Princess Poot, the shittiest princess, who experienced Eeyore-levels of downpour all year. Her peers once mock-elected her Mayor of Loserville, but the surprisingly-haughty citizens of Loserville didn’t want her any more than the Kingdomvillains did.

As the vile love occasion crept closer, Poot sank into a deeper depression than usual. She’d never had a date on Valentine’s Day—not a prince, not a pauper, not even a proper pauper prince who really needed the dowry.

This year would be different, she vowed: She’d buy herself a man. She placed an ad in the Loserville Whatever, that town’s local paper.

You: Not picky, need cash, still reads newspapers

Me: Superlative royal lady with interesting features

Where: Annual Kingdomville Valentine’s Ball and Eventual Drunken Groping Regret-Fest

Pay: Five kegs of beer, or the equivalent in anti-fungal cream

Reply to:

Several august gentlemen replied. One said “send tits lol.” Since her boobs weren’t detachable anymore, Poot eliminated him. Besides, people who thought “lol” was a punctuation mark annoyed the shit out of her.

Another messaged her “I emerge at the crack of dawn to salute the almighty universe-energy with three hours of Yoga, followed by a lentil-bark cleanse. Next, I dialogue with flowers—not just roses, but less pretentious plants, if you will, such as the strangling venom vine. Sure, it’s dangerous! YOLO.” Poot quietly deleted that message. Crack of dawn? He was obviously weird.

The last note was much better than the others:

Dear Royal Female,

You sound hot. I’d adore being your Regret-Fest date. We’ll drink a lot and see where the night takes us. I’m a nice guy who puts women on a pedestal.

PS: I’ll take the cream.

Later Bra,


Chad sounded like the bee’s knees, even though the last time Poot ventured onto a pedestal, she ended up having an incident that cannot be discussed without the Royal Lawyers present.

The night of the big date, Poot put on her best ugly pink princess dress and shellacked her face with makeup to make it seem more alive. She even dared to add a dash of lipgloss (pink, natch) should Chad want to swap spit, or teeth.

Posing at the top of the ballroom stairs, Poot deigned to be held up by a guard to avoid her third tumble of the night. She’d already lost a glove, and half the skin on her right knee. These spasming pains were soon forgotten when she saw Chad enter the room proudly, his fedora really highlighting the thin beard growing in a crooked line from sideburn to sideburn. He dashed up the stairs and handed her a bouquet of daisies.

“Hey, babe,” he said.

Poot had never been called a babe in her entire life. She thought she had once, but it turned out that the man was greeting the famous pig next to her in the beauty contest. The damn thing had beaten her.

Gooey nervousness raced through Poot’s body. “Hi, Chad,” she said like a cool person. “I’m not contagious this week or anything.”

“You’re just as beautiful as you told me in email,” said Chad. Poot hadn’t remembered telling him what she looked like, so this was an accurate statement. “Do you have misunderstood feelings you want to share?”

“Do I!” Poot grabbed Chad and used him for ballast as they descended the stairs.

“Princess Poot and Hired Underling,” announced the Talks Sonorously in Public Minion. Poot thrilled on the inside. She was usually announced as “Princess Poot and Nobody. She’s alone and likely to stay that way. Pathetic.”

Chad and Poot danced and talked all evening. She said she enjoyed his outfit adorned with many glittery skulls. He listened to her story about the pedestal lawsuit and that one litigious little asshole four-year-old. He fetched her chocolates, and bandages for her seeping knee. What bliss!

“How did you get this gorgeous scar?” Chad pointed to a jagged line near her collarbone.

“It’s from my vestigial fin.”


“I said skateboarding accident.”

And so the evening came to a close. The Royal Orgysmith organized the remaining party-goers into lines of “flexible” and “brought own riding crop.” Poot pulled Chad toward the exit. “Your fungal cream is waiting outside, if the raccoons haven’t gotten to it.”

Chad yanked his arm away. “But I brought my own riding crop.”

“Oh, I’m a princess, so I can’t make sex gruntings until I marry a handsome prince. There’s a by-law ever since Princess Backseat III got pregnant again. If only someone would invent slut pills we could force Republicans to pay for.”

Chad threw his fedora into the dust. “You mean I was nice to you the whole night, and all I get is what was promised to me? You bitch! I listened to your stupid story about why you only have three fingers on one hand. And a fin? A fin?”

Poot’s lip began to tremble. “I thought you…but I haven’t molted or anything.”

“I only did this to put a bag on your head and get some poon tang. You bitches are such dick teases. I’m a nice fucking guy—why do I get friendzoned?”

An alarm sounded. In moments, they were surrounded by guards with pointy swords and intractable expressions. Guard Number Seventy-Two stepped forward and bowed at Poot’s feet. “Princess Poot, did this douchecanoe utter the forbidden word?”

Poot peered at Chad from the tip of his fauxhawk to his snakeskin sneakers. “Yes. I could scarce believe my ear.”

Guard Number Seventy-Two stabbed Chad through the heart, and then shook the sword around so that his guts fell out and blood splattered everywhere, which attracted the raccoons. After the guards pulled Poot to safety, she said, “To think, Chad was only being kind to me to play with my poon tang! It’s in the shop, anyhow.” She shook her head. “He should know that in Kingdomville, the place where everything is named literally, the F-Z word is such asinine bullshit that it invites the death penalty.”

Guard Number Seventy-Two nodded, for he knew that genuine respect was the only way to achieve true love. And finding the clit never hurt, either.

Thus ended Poot’s most disappointing Valentine’s Day, but not the gruesomest. She’d learned a valuable lesson: Never date a man with a stupidly-shaped beard. Oh, well—at least she could watch the orgy and take some notes for her Tumblr.

The end.

Next week Princess Poot is in for an apocalyptic adventure with some undead princesses:  The Shittiest Princess and the Three Ghosties.  OoooOOOOOoooOOOooooo!

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Lucy Woodhull

Lucy Woodhull is a novelist, humorist, parodist, and all-around geek. Her new venture is THE SHITTIEST PRINCESS, a series of un-fair-y tales right here on Persephone. You can check out her sexy, fun romantic comedies at

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