Pirating

"P..please...Mistress...not my tailhole...please..."

The mare shook her head, her hands on his hips, and lunged forward, penetrating him roughly in one long thrust, burying the dildo to the hilt in her slave. He dared beg...he dared expect mercy...

"Just be thankful I'm not doing this in front of the whole crew...I would enjoy letting them watch you squirm, my recalcitrant slave..."

His long agonised cry of anguish was her ultimate reward. He would learn, of that she had no doubt. His tailhole felt tight, resisting her thrusts and taking the thick stallion dildo unwillingly. She rammed away, breaking him, stretching and punishing his tailhole until it yielded to her rutting and she fucked him like a stallion taking a mare, feral and wild, pure sex and lust. She loved watching the way his rump compressed each time she hilted, and the way his back shook with the feeling of having his tailhole violated by a mare. His nickers began to turn though, from pain to something else. She stroked his back, sliding fingers across every painful welt as she whispered for him.

"Remember slave, no cumming. Your body is mine, your balls are mine, and your seed is mine. If I want you pent up and desperate you will be. If I want you drained and aching and still stroking your cock until it hurts and the mere thought of orgasm brings pain you will do that too."

Gabriel could only grunt and clench his muzzle tight. The demon mare had him, and he couldn't resist though. Every third agonising thrust slapped the tip against something deep inside him that made his cock twitch and a burn flood through his body. It grew, building on each new thrust, and the mare's words made the burn into a raging fire.

"Your tailhole is mine slave. If I want it whipped, I will. If I want it filled, you will get on your knees and beg me to fuck you. If I want the entire crew to use you as a toy, you will plead for more and thank me for it. You are mine slave. All mine."

"Noooo!"

"You dare resist? Would you like more of my whip on your balls stallion? I could feel you when I did it; your cock spurted pre all over the deck. I know you stallion; I know your secret needs. Do you want me to punish you slave?"

"Ahhhhh! No...no...no...."

"Admit it!"

Amethyst changed her stance, bringing the tip of her strap-on against the sensitive nub of stallion flesh inside her poor slave. He was close to breaking, she knew. She could smell it, the nearness of cum, and the scent of his sweat. Holding his hips tight, she began thrusting fast and shallow, hitting his nut on each entry. The stallion began to moan a long undulating cry of torment and need in one as she rode his ass, bringing her own orgasm close to bursting.

"Yes....you want it stud...you need it, need a mare to take you and show you your place...admit it stallion...admit it...let it out...let it out!"

"NOOOOOOOOOO!"

With a final anguished cry, Gabriel unloaded, his cock spraying the deck and the cannon in thick stallion seed, a white gusher of humiliating release as his battered ass clenched down on the thrusting dildo. The sensation of tightness, the scent of seed and the obvious distress in the proud stallion pushed the mare over the edge, her own orgasm mirroring his, waves of pleasure that went on and on, but triumphant as his were tormented.

Amethyst pulled slowly from his tailhole, her needs satisfied for the moment. She could see the stallion lying broken, his body heaving though he was not crying. His tailhole winked, spread wide and trying to close but failing, the lips angry and red. She liked this view of him. She wanted to get used to it, but she had plenty of time.

As she removed the harness, sliding the end of the strap-on from her sex, her body gave a long shudder of pleasure. She was almost satisfied, but not quite; she had a good idea how to finish herself off though. Meanwhile, her hands caressed the traumatised stallion, bringing him back from the edge. He shivered to her touch, and she caressed him, soothing his body and mind momentarily.

"I told you not to cum, Gabriel."

"Please mistress...I'm sorry...please...please!"

"No excuses slave. I will get the smith to make you something special to help you though. A harness with a cock cage. A nice tight leather strap around the top of your scrotum to make it easier to resist, and a nice metal cage over the top of your sheath. Just enough for your cock to poke out, not enough for you to pleasure yourself or to put it anywhere I don't want it to go.

Gabriel shuddered, the thought of his precious balls and cock constricted and bound both terrifying and exciting. Surely she could not be too merciless though...

"I think I will leave you in for a month, at first."

"Noo! Oh God...please!"

"Yes slave, no cumming for a month. If you are good, I might let you out. If you are very good, I might let you fuck Marissa while I watch. One day, when you are well trained and I can trust you not to cum, you will be allowed to fill my pussy and pleasure me totally. First you need to learn the benefits of restraint though. And obedience."

His whimper just made her more aroused, her poor stallion unaware how much she enjoyed his torment. And how much it drove her to want more.

"Now for you to learn the price for disobedience. I said no cumming, didn't I slave?"

"Y...yes..."

"Tanno!"

The door opened quickly, a very large bull walking steadily into the small cabin. His bulk wasn't easy to accommodate, but Amethyst didn't need him there long. Tanno grinned a conspiratorial grin at his captain.

"Aye aye captain!"

"Hmmm....were you waiting there?"

The bull grinned sheepishly. In fact, the whole ship wanted to be close to hear the stallion's punishment, but Tanno had used his bulk and his influence to take pride of place just outside the door. He had heard everything, from the whipping to the screams to the terrible sound of virgin tailhole being violated, then the shamed orgasm that finished it. He hadn't seen, but he had a fair idea of what the stupid pony had been through.

Lucky bastard...

"Tanno, my new slave needs another lesson and I think you are perfect to teach it."

"Yes Captain!"

Amethyst lay back on her favourite chair, beckoning her attendant to her. Marissa padded over happily, though she was disappointed she wouldn't get to see the next part. Still, there were compensations. She nuzzled against the soft folds of her mistress, already swollen and pink from multiple orgasms. She would be gentle, and loving. She extended her tongue tip gently to just flick one pussy lip, ignoring the rose coloured clit for now. Plenty of time for that while the arrogant stallion got his.

The mare had a perfect view though, as her bound slave followed the bull's motions with increasing dread. The Boatswain casually lowered his pants, revealing a long thick bullcock, swaying out in front already. Tanno had enjoyed the show, even just the sounds. Now he would get to be part of the action, and his cock stiffened to full erection.

"Open wide little pony."

One massive bull hand wound Gabriel's tail tight in its grip, while the other lined his tapered cock tip against a clenching tailhole. The stallion knew better than to beg. Instead, another part of him took over, one he never knew existed.

"Thank you Mistress..."

A broad bull ass flexed, and Amethyst watched her slave's puckered hole envelop the full length of Tanno's formidable cock, the stallion whimpering but not begging, and not crying out. His cock, still hard, spurted another line of clear precum to join the puddle of seed under him. She laid her head back and moaned, just listening to the sounds of her slave's punishment while Marissa ate out her sex.

This was going to be a very, very good year.

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A gift for the ever formidable Amethyst Mare, writer, friend and Mare Extraordinary, with the soul of a pirate captain and the temperament to best even the most unruly stallion.

On this day, the Thirtieth of January, in the year of our Lord Two Thousand and Fourteen, from the respectful hand of Gabriel, your faithful servant.