Breaking Her In (Pt. 2)

Written for @cool_grey9, with thanks.

Content warnings for this story (click here for guide):


Evanstow did not look up as Thea entered, but continued filing.


“Um…” Thea twisted a ring on her finger.

“If you’re going to stand there and hum, Ms Turner, kindly do it elsewhere. I’m trying to sort out approximately thirty years of Pevensey stock records and the previous system, it emerges, was a series of suitcases in one of the outbuildings.”

“Oh. Um, sorry.” Thea was taken aback, though she’d not been certain what to expect. “I’ll go. I just – wondered if you’d seen… a phone…but I’ll find it. Anyway, goodnight!”

She shut the door quickly and scuttled off into the corridor. Her heart was hammering. What the hell was she doing? God, maybe the last bus hadn’t gone and she could get home before the ground swallowed her up.

“It’s in your hand.”

The Master was standing behind her.

“Your phone,” explained Evanstow. “It’s in this hand.”

He took a slim black crop from his boot and tapped her clenched fist. Thea froze at the light, brisk touch.

“Oh…yes,” said Thea, opening her fingers to confirm. “There it is. Thank you Mr E. Lose my head if it wasn’t screwed on.”

“I’m sorry. What did you just call me?” Evanstow stroked the cane up underneath her chin.

Thea turned red. “Sorry! Oh god, sorry. I meant to say Mr Evanstow or Master or whatever, but I just used the short version. I didn’t mean any disrespect.”

“I’ll save you a few syllables,” said Evanstow quietly. “It’s Sir. If you’d like to succeed here, you’ll remember that.”

“Yep! Yes – got it!”

“Got it…what?”

Thea hung her head. “Sir.”

“Better.” Evanstow turned on his heel and headed back to the office. He paused.

“Well, Turner?”

Thea gulped.


“Well I presume you’ve come back because you’d like to learn to ride.”

That was part of it. Thea nodded.

“And of course, to apologise for your inexcusable behaviour earlier.”

He replaced the cane in his boot.

“Meet me in the arena. I need to fetch some things from my office.”

He strode off into the half-light.

Thea paused, then walked out of the building. The wind had sprung up and buffeted her down the Pevenseys’ long drive. Stone animals lined the walk and they loomed above her in judgement. But halfway to the gate, she stopped and looked back.

When she entered the arena, he was already there.

“I’m not sure where you went just now but I don’t appreciate waiting. Either you enter my tutelage in good faith or we forget this whole arrangement. I’m a very busy man. You can continue on here as a stable hand, providing your work improves, and I shall return to tutoring thankful students. Your choice.”

“I would like…I’d like to learn to ride,” said Thea. “Please.”

“Take off your top,” said Evanstow.

“What? How is that…?”

The Master strode across to her and took hold of her t-shirt. Thea held the fabric in place and stared at him pleadingly.

He took away his hands and turned around to a large leather bag. Picking something up, he went round behind her. As Thea tried to twist round, he snapped “Stay still.”

Thea felt the cool back of the scissor blade slide up under her t-shirt. She heard the sound of fabric being sliced and felt a cool breeze on her back. She yelped as the Master’s strong hand slipped off the back half of her top.

Clutching the remaining scrap of cotton in front of her, Thea trembled.

“Let go,” ordered Evanstow. “Now.”

Thea shook her head.

Evanstow whipped off the remains of the t-shirt to reveal the white crop top once again.

“Ah yes, I’d forgotten this charming little garment,” he chuckled. “How old are you, Miss Turner?”


“Oh yes, very sweet. I suppose you don’t really need a grown-up bra with these perky little breasts, do you? But I like them very much.”

Thea blushed at his mockery. Once again, her nipples began to stiffen.

I think we need a better look at these,” said the Master. “Up, please.”

Thea shook her head again, crossing her arms across her chest.

“As I said earlier, Ms Turner, I am busy,” yawned Evanstow. He took her wrist firmly, sat down on an upturned box and pulled her across his lap. Thea kicked and found her leg trapped by his strong calf.

“The first six will be over your jodhpurs,” said Evanstow. “After that, we’ll see how you feel about lifting up your little training bra like a good girl.”

He gripped the waistband of Thea’s jodhs, pulling them up between her legs to show the outline of her pussy. The centre seam pressed snugly against her clit, causing Thea to pant where she lay.

The first swat landed and she let out a yelp. Even through the material, the Master’s hand was a hard, flat, merciless tool.

“Count them.”


“Uh – one, two?” Thea panted.

“No, that’s one because you didn’t count the first,” said Evanstow.


“Ah! Thr-two!”

“Good girl.”









Evanstow sat back.


Thea obeyed, unable to meet those grey-green eyes.

“Now, lift up your crop top for me.”

Thea hesitated. She couldn’t!

“Very well!” Evanstow lifted her top, showing her pert breasts and hard rosy nipples.

“NO!” Thea yanked the cotton back down.

“As you wish,” said Evanstow, taking her wrist once again. He took her across to a saddle stand, bent her over the top and wrapped a halter rope round her wrists. Thea squealed indignantly as he passed the end of the rope under the top of the stand then tied them around her legs. Roped in place, Thea tried unsuccessfully to buck. Despite her struggles, she found her jodhpurs pulled easily down to rumple round her ankles. There was a pause and then she felt her knickers pulled down as well, her bottom and pussy exposed to the air.

“You can’t –!!!“

“Six,” said the Master calmly. “This time on the bare, with a crop. Oh, and look up a little. Who’s that bedraggled creature?”

Thea raised her head, still panting with exertion. The saddle rack faced another huge mirror. She saw her face red, her hair knotted and her white bottom held up, ready for the crop.

“Count,” came the command.

Thea yelped as the crop swished and cracked down onto her buttocks. The girl in the mirror had tears in her eyes.

“Ahh! ONE! ONE!”

“Good girl.”





The last three were delivered in a swift volley.


“Unghhh! F-FOURFIVESIX!!!”

Thea’s head swam. Her naked bottom burned from the crop and her dignity was shattered. She felt Evanstow untie her, slipping a hand between her legs as he did.

“Dear me, someone did enjoy that.”

He held up a glistening finger in front of her as he helped her up and Thea cringed.

“Now, shall we try again?” asked the Master.

Thea didn’t wait to be asked, but stood with her jodhpurs round her ankles and meekly lifted her little cotton croptop.

“Lovely,” said Mr Evanstow, running a finger over both nipples. “And since you appear to be quite aroused, I have just the tool to improve your riding posture.”

He brought out a saddle-shaped black leather device and placed it lengthways on a narrow bench. Then he crooked a finger at Thea. Her bottom still smarting, she bent to pull her jodhs back up and Evanstow shook his head.

“As you are, please.”

Mortified, Thea was made to shuffle awkwardly across to him, her ankles hobbled by the tough material. Evanstow chuckled.

“Oh, that is enjoyable. You’re not quite the banshee you were earlier, are you? Now come and sit on this saddle for me. I suppose you can take off the jodhpurs to do so.”

Thea winced at the thought of the cropping she’d just received. She tugged off the trousers using her feet, and found her hands covering her pussy as she straddled the bench. Her legs only just touched the ground either side, tipping her forward onto the raised front. As her clit touched the cold leather she felt a shiver of electricity inside.

“Now,” said Evanstow. “Posture is everything in riding, and we’re about to test out your poise and composure.”

He smiled at Thea’s embarrassment, as she sat upright, squirming a little.

“That’s not terrible. Work to do, but not too bad. Nevertheless, sitting upright while static is quite different from staying centred and balanced on a moving animal. So let’s simulate that a little.”

He picked up a red remote control and pointed it at the saddle. Thea gasped as she felt a buzzing and rocking between her legs. It was impossible to scramble off the high seat, so she clung on.

“Focus, Ms Turner!” said Evanstow. “Focus!”

Thea panted and gritted her teeth as the vibrations tickled her clitoris. She couldn’t suppress a low moan. Oh God, it was powerful. She felt a wave-like motion between her legs, washing her ever closer to the shore.

“P-please…” she whispered, shutting her eyes tightly.

“Such a good little slut,” she heard in her ear, and as the words were spoken, a huge surge ran through her and she cried out as she came. The toy buzzed a fresh jolt through her, then stopped.

Thea kept her eyes closed for a few seconds, her head full of colours and her swollen clit pounding. She sensed the Master watching her, but was too breathless to imagine what he was planning.

“Up,” said Evanstow at last. Thea obeyed. Naked from the waist down, with a bruised bottom and her little tits exposed, she stepped off the device, utterly humiliated.

“One second,” said Evanstow. “I’d like you to look at what you’ve done.”

He took hold of her hair and steered her face down to the saddle. It shone with moisture.

“Somebody made a terrible mess of the training device, didn’t she?” said her instructor. “Somebody should clean it up.”

Thea looked up at him, wide-eyed. He couldn’t mean…

“Go on,” said Evanstow, bringing her face still lower. “Clean it up nicely. It is your mess, after all, dirty girl.”

Thea, hardly knowing what she was doing, closed her eyes and put out her little pink tongue.

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