Jillin' the Villain

by ROBCakeran53

1: In which the odds were against her, yet one of the Princesses still won 200 bits.

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Author's Note

So this might seem odd, to be posting a story on my main account that's clearly about sex, however like YCH this story isn't really about the sex. Or maybe it will be, I dunno, however at this time after this there isn't any planned explicitness for some time.

I've been recently going through a bunch of Sombra shipping stories, mostly involving Fluttershy or Starlight Glimmer, and well, they're good. Most have been, but they all felt too... harsh. Too dark, edgy, depressed. I thought, you know, something different was needed. Then I got talking with my pal Pone 9, and well... this happened.

We will be posting in our author's notes who wrote which chapter, so this first one is mine. Sorry that I'm not sorry.


1: In which the odds were against her, yet one of the Princesses still won 200 bits.

Starlight Glimmer was quite the smart mare.

Sure, at her worst she was a evil, controlling, and the manipulative leader of a small town in the middle of Nowhere, and at her best she was socially awkward and had an itchy trigger horn, but she was never dumb about anything.

Frightened, startled, out of her element, sure, but she simply lacked the experience to properly handle the situations constantly thrust upon her.

After the second, or possibly third, defeat of King (former) Sombra by the Tree of Harmony slash Elements of Harmony slash explodey rainbow magic, he was totally and entirely vaporized.

Except, as was usual, his horn.

It had so much pent up dark magic and teen angst slash anger issues that the stubborn piece of ivory, tainted red with blood lust, hormonal imbalance, and rage, simply would not go away. Twilight Sparkle had tried everything she could think of, and some things better not thought of. The rest of the princesses simply wanted to banish it, cast it away to parts unknown in the hopes it wouldn’t ever appear again (or at least for another thousand years).

And then Starlight said that was dumb.

Both Princess Luna and Cadance looked to the mare with amusement, while Twilight nearly flew (literally) into a panic, and Celestia rubbed her forehead from a migraine, however motioned with her hoof towards the unicorn mare to continue her thought.

Honestly, having never dealt with a deceased evil pony’s horn before, this was where Starlight’s lack of experience then came into play. She was not stupid, simply lacked the forthought of the impending and then what? It had worked for her before in the past, with only a few minor setbacks here and there that the Power of Friendship (™) could later fix for her.

Or, you know, with her.

Realizing she suddenly held the attention of four princesses, the reformed villain could only blurt out a hasty response.

“I’ll watch over it!”

Two sets of eyebrows nearly reached orbit, one jaw nearly cracked the marble under their hooves, and one princess of the night nearly rolled on the floor from laughter. It was the ironic, “this is such a bad idea but let's see where it takes us anyway” kind of laughter only a princess alive for a few hundred years could achieve.

So for the next hour, several pots of tea and coffee were consumed, princess yelled at princess, then they hugged, then they cried, and then yelled once more, until all four came up with the same conclusion:

This was probably, absolutely, most definitely, all more than likely, the worst idea ever, but let’s see what happens anyway.

And thus Starlight Glimmer, freshly crowned headmare of the School of Friendship, was trusted with the horn of King Sombra. Once the mare left, on shaky hooves, the four princesses looked at one another before Cadance broke the silence with a wager on how long it took for her to botch things up. A side bet was then established on which of Starlight’s “friends” would be a helping factor, with good odds on Trixie and HLS.

As it would turn out, they weren’t too far off.


Months had passed, and Starlight Glimmer found herself at her desk, in her office, in the School of Friendship’s Dean’s Office, which was hers now. The school, that is, which also included the Dean’s office, her office.

She was still coming to terms with her present reality. It didn’t help matters when she still found occasional purple feathers or dragon scales scattered about.

It was also still a weird feeling, being in charge of a huge school, hundreds of students from all kinds of backgrounds and totally different species. Lots of stress, sleepless nights, finding good help, finding good reliable help, giving up and just having Trixie, Sunburst, or even Discord step in when needed.

The usual kinds of stress, really.

Today was a usual busy day, where she only had ten to fifteen minutes to herself between periods. Class periods, that is. It was a hot summer day, Celestia’s sun, which was kinda controlled by Twilight now, blazing down upon the inhabitants of Ponyville. It seemed as though the focus was on the school, or more so her office. On herself.

Starlight ground her bottom into her seat. She hated it when her heat got away from her. Sure, it wasn’t anything a little medicine or some pegging from Trixie couldn’t fix, but days like today where she didn’t have her meds, the time to get meds, ability to stimulate herself proper, or an emergency dildo stashed somewhere only Pinkie Pie knew that it made being a mare miserable.

Slamming her face on her desktop, Starlight let out a groan of pent up frustration, the casual drip drip drip from fluids dripping from her seat to the hardwood floor. The janitor was going to have a fit if she didn’t clean up her own mess.

She lifted her head just enough to rest her chin onto the wood surface, huffing a bit of her frazzled mane from her face and looked around. Nopony was scheduled to visit. Nocreature had been by all day with any problems. Even Trixie was behaving herself downstairs with only minimal disturbances from Discord.

Maybe… she did have a moment to herself. Rub one out with enough time to dive into the moat to cool off afterwards.

“Yes,” she said to herself.

Only now the question was how? While hoofing it was tried and true, after a while it just got bland. Trixie was busy, Sunburst was back in the Crystal Empire probably being dom’d by Cadance and Shining Armor, the anal slut he was.

A bit of sunlight suddenly glared from a glass bowl on her desk. Inside that glass dish was none other than King Sombra’s horn. Pointed with a menacing curve, mostly a blood like red that grew darker towards the fractured base.

Instantly heat radiated from her cheeks. No, she couldn’t… really now, it would be just… wrong.

And yet, for everything that Starlight was, she’d done a lot of wrong things only to come out stronger for it. But using a dead, evil unicorn’s horn to get herself off? Could she really stoop so low?

Her eyes looked to the wall clock. She still had a good eight minutes with change, easily enough time if she had a toy assisting her.

She groaned, looking about her office, the only other occupant was Phyllis, who seemed to turn its leaves away from her, like it knew what she was thinking, didn’t approve, but couldn’t really offer any other suggestions.

“Urg, fine!”

With a wave of her magic, the glass dish was removed, and the horn brought over closer for inspection. While she’d had looked at it many times since placing it upon her desk, she never really brought it up close to examine the finer details. It wasn’t smooth, or even spiral like a typical unicorn’s horn. It was rough, small abrasions scattered about, as if with each combat he had in his past his horn took a beating.

She idly wondered if it had ever taken the kind between her legs.

Leaning back into her chair, she eased her legs open, and ever so slowly moved the horn down towards her waiting, moist sex. Her nipples were fairly hard, and as an afterthought, shifted the horn to rub between them. Through the thin hair and mostly bare skin, the horn wasn’t rough, but simply abrasive, much like she imagined the stallion himself being.

Eyeing the clock once more, she’d already wasted a full minute. If she was going to do this, it had to be soon.

“Faust, forgive me…”

She brought the tip of the horn to her folds, and began stroking, allowing her juices to begin coating the object in her magic. Leaning further back, she hit the chair’s stopping point, and began to gently insert the tip inside of herself. Inch by inch, and as she realized, the horn was also much longer than a typical pony’s. Maybe slightly longer than Princess Cadance’s, but nowhere near that of Princess Celestia.

Now there was a pony she’d love to ride.

“Oh I’m soooo going to Tartarus if I’m caught…”

And yet, the thrill seemed to excite her further. Half way in, she began to rock the horn from side to side, up and down, allowing the slightly rough ivory rub all around inside of her, finding those few spots only Trixie could get just right after a fight.

Cautiously, she pulled the horn back out of her, and brought it up to her lips to lick her own juices. It was tangy, as expected, but another flavor was there, something she couldn’t quite place. Possibly because she didn’t clean the horn, or that maybe some evil was radiating from it because of her actions.

Another suckle, another lathering with her tongue, and then slowly she dragged the sharp tip down her throat, her chest, lower barrel, between her teats, and back to her winking vulva. It was a dangerous thrill, that sharp implement, as if Celestia herself was teasing her.

With a thrust, she shoved the horn back inside her waiting pussy, and began a slow, rhythmic back and forth piston action with it, allowing it to go slightly deeper when she felt like it.

“Oh yeah, Celestia, just like that.”

For the record, it was Trixie who liked the roleplay. Starlight would be Twilight, and Trixie would be Celestia. That way they both would win.

Starlight’s magic was starting to grow feverish, the light was getting more intense as she began to feel that pressure from her heat reaching a peak. Deeper, faster, more aggressive thrusts with the horn, not caring for the sharp point, only driving her gspot closer and closer to her release.

Then suddenly, the horn began to vibrate. So lost in her menstrations, Starlight didn’t even think about this, only enjoying the reverberations from her insides, versus the fact that she herself was not causing this.

She didn’t honestly care, she was so close.

Her chair was now rocking with the thrusts, pushing it farther away from her desk with small squeaks of the wheels. Her window was open behind her, but unless some curious pegasus was up there spying on her, nocreature really bothered her that way.

The vibration began to grow in intensity, and her horn’s glow was being outshined by a brilliant light coming from the horn, but she didn’t care. Her eyes were closed, imagining the Royal and Regal Celestia horn fucking her like no other pony could, even Trixie with the horn extension.

“Yes, yes, YES!”

Starlight was peaking, her orgasm on the brink of bursting. Her magic flared, pouring more into the horn so she could get everything out of it she desired.

“Oh, yes! FUCK!”

And the dam burst, her quivering pussy splashing out, and all at once her magic, the bright light, and the vibrations, all stopped.

She stayed laid back in her seat, eyes closed, panting away as she rested her hooves upon her chest and barrel. It had been a long time since she felt one so intense, so alive like that by herself. A faint smile graced her lips as a warm breath blew upon her wagging tail. She was-

Wait. Hold on.

Starlight’s eyes shot open, and slowly she leaned her head forward to look down between her legs.

Kneeling before her, his horn still shoved well into her pussy, was none other than King Sombra himself, eyes wide in shock as they focused on her breasts, and his face covered in her mare juices.

Seconds dragged on, the ticking of the wall clock reverberating on the walls like it was a doomsday counter. One blink, then two, and King Sombra’s eyes finally looked from the perky purple mounds and up to meet Starlight’s own wide eyes.

“Uh… hi?” Starlight said with a gulp.

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