Where No Man Has Cum Before
A five year mission (to space jail)
Captain Kirk unhooked the seatbelts and looked at the dead shuttlecraft's controls. Nothing. Nada. Zip. He was stuck. This shuttle was out of action.
"Captain's log, Stardate 41153.7. My shuttle lost all power and I made a dead-stick landing onto the local class-M planet. I seem to have accidentally landed in the center of a small village. The buildings are somewhat small, well-built in a nineteenth-century European style and painted in garish, almost cartoonish, colors. This is clearly the home of intelligent life. I will exit the shuttlecraft and investigate. I can only hope that my crash landing didn't injure or kill any locals. My emergency beacon appears operational, so once the Enterprise arrives, we will try to repair the damages and make amends."
Kirk kicked the jammed hatch open and found he was only slightly more than his own height above ground. He jumped, landed, and rolled, landing in a crouch, hand near but not quite on his phaser.
Something that felt like a stun bolt, but wasn't exactly a stun bolt, hit him in the middle of the spine and then wrapped around his torso. A light blue corona, like Saint Elmo's fire, surrounded him, lifted him off his feet, and clamped his arms to his sides. Struggling, Kirk kicked ineffectually and shouted.
Finding himself turning around a half-circle, he faced a horse.
Smaller than him, white-coated, purple-maned and tailed, and... with a unicorn horn that was glowing the same color as the Saint Elmo's Not a Stun Bolt that surrounded him.
"So," she said, in a voice like a mixture of adolescent fantasies, sex lube, and prickling anger, "you came crawling back. And wrecked my boutique!"
"My name is James T. Kirk, capt -- "
The corona clamped around his mouth. "Be quiet, Anon. I told you you would come crawling back. I wasn't good enough for you? I was a crazy bitch? Who's crazy now?" A wadded up ball of silk fabric levitated up and popped into Kirk's mouth, gagging him. "And that skin color -- what is that, peach? So biologically implausible. Like I wouldn't know your green hide under any color!"
She carried him into the half-wrecked building and dropped him on a couch. Bolts of fabric and tape measures levitated from the far corners of the room and tied his arms to his sides and his ankles together and secured the gag into his mouth.
Leaning in, nose-to-nose with him, Kirk felt the anger boiling off her. "I told you what would happen if you ever came crawling back to me."
A pair of scissors levitated up from a sewing table.
They approached Kirk.
They approached his crotch.
He began to squirm and fight the bonds, but her corona returned and held him still. "Oh, don't move. I don't want to hurt you... yet."
The scissors snipped into his space pants, just on the left hip, and began cutting along his belt line, then down and across, opening the crotch, a large patch of black fabric falling away and leaving his modesty completely unveiled to the angry horse. He felt as naked as if his deflectors were down in front of a Romulan Warbird.
Kirk's heart beat, sweat dripping down his back. Was she going to emasculate him? The scissors were huge and wickedly sharp.
She dropped the scissors on the floor, opened wide, and sucked his dick -- flaccid with terror -- into her mouth.
Not prepared for that eventuality, Kirk's eyes went wide. Glaring angrily, she made eye contact while sucking. Her warm mouth and strong tongue licked up and down his shaft, playing with his tip, her teeth brushing his skin. Although Kirk was usually the first to jump at hot alien sex, this was not one of those cases. He generally restricted himself to humanoids.
This was, Kirk decided, the Kobayashi Maru all over again: he was going to get unwillingly fucked by those with power over him. Except, this time, he couldn't reprogram the simulation. And the fucking was literal not figurative.
As his kobayashito got hard, the creature tilted her head, lining up her mouth with her throat, deep-throating him. Kirk gasped around the gag as her throat, tighter than any hole he'd been in before, massaged his tip. Don't enjoy this, don't enjoy this, don't enjoy this, Kirk told himself.
She opened her mouth and licked up from the bottom of his dick to the tip, leaving him erect and pointing at the ceiling, a string of spit stretching from his tip to her tongue.
"Very well, Anon, you came crawling back to me? Is this what you wanted?" She crawled forward until her front hooves were planted on his shoulders and her crotch above his throbbing hardon. Raising her tail, she lowered her rump, giving him an angle to see hard nipples, a wet pussy, and pink lips. Her corona grabbed his dick and positioned it, lowering herself onto it.
Her channel was wet and hot and soft and wonderful. He needed a few second to remind himself he was being sexually assaulted, and that he wasn't supposed to like this.
The small horse started thrusting, up and down, on Kirk's warp nacelle. Her front hooves pressed his shoulders into the couch as her hips slapped wetly down across him. He got harder, but the bindings and the ball gag removed any excitement, any chance of cumming. It was purely mechanical, none of the emotion needed to actually get off and finish. She grunted and humped, sweating, her mane getting matted, Kirk's dick getting raw from the repeated thrusting.
A second unicorn, even smaller, barged in the door and paused. "Rarity, what's going on? There's an airship poking out of your boutique... and you're fucking Anon? I thought you two broke up?"
Rarity, Kirk noted. Her name was Rarity. That would go in his complaint to their government once they opened relations... and no, being tied down and horseraped didn't count as diplomatic relations.
"Ah, Sweetie Belle, darling, I'm getting tired, can you finish Anon off for me?"
My name's Kirk! Kirk raged silently.
"What happened to him? He's not green anymore."
Kirk wondered, Was this Anon an Orion? Had the Orions already made contact with this species?
Rarity lifted off his warp nacelle and shuffled sideways, a long string of pussy juice connecting his tip to her lips before she backed away and hopped off the couch. The little one -- Sweetie Belle? -- dropped her saddle bags and climbed up on the couch. Turning around, she pointed a fine filly fanny and flanks at him and raised her pastel-colored tail. That revealed a tiny pink slit and tight white butthole and Kirk's dick jumped unwillingly.
Her own horn lit, a softer and lighter-colored corona grabbing his dick, and she lowered herself.
The sensation was literally the best sex he'd had in his life. The tiny filly cunt was hot and tight and soft and he slid in instantly.
"Ouch!" Sweetie Belle said. "He's bigger than Sandbar."
"Oh, Sweetie, is there anypony in that school you haven't fucked?" Rarity said.
"Sunburst." She bottomed out, dripping filly juice over his balls, and then pressed up. Kirk's eyes closed in bliss as the tight twat dragged up his shaft, wetting him and massaging him as her well-muscled channel squeezed on his tip.
Struggling against the bindings around his arms and ankles again, Kirk fought to get free. Rarity's corona clamped around his throat and squeezed, gently, and he stilled. She squeezed a little harder and Kirk fought for breath. His vision began to twinkle black at the edges and Sweetie Belle panted, pounding wetly up and down on his shaft, her tail raised high and her tiny filly butthole winking as she started to cum, juices soaking his balls and she shouted as her channel clamped even tighter on his shaft. As he felt his consciousness slipping away due to lack of breath, Kirk came, too, a huge load up into the filly's tiny cunt.
Rarity released his throat and he sucked in air, going limp against the couch. Sweetie Belle stood, popping off his dick and dripping cum onto his space pants.
McCoy, Spock, and four red shirts barged in.
"Hi!" Sweetie Belle said to them. "Anon brought friends!"
They stared at Kirk's wet dick and Sweetie Belle's drippy pussy.
Sweetie Belle raised her tail again and peed on Kirk, soaking his shirt with warm, strong-smelling piss.
"Good God, man, she's just a filly!" McCoy shouted.
"Captain," Spock said, "under Starfleet Regulation four seven three three point nine, I must report your having sexual relations with an underage local to higher authority."
Derpy crashed into one of the red shirts, killing him instantly.
Author's Note
Pretty sure Anon is Orion, not human.
https://memory-alpha.fandom.com/wiki/Orion
