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Miss Shy bit her lip; it was worth a shot…
“Um, sorry to bother you sir, but… well, I haven’t been feeling super-good this morning and, um… do you think you could help, um… m-milk me again today like you did last night? It r-really helped then but now I think they’ve gotten even… bigger? and the pressure just really hurts…”
Her long, lush new tail swished behind her with a mind of its own, betraying her excitement. Her top-heavy frame – now several inches shorter than it had been mere hours ago – wobbled slightly, struggling to hold its precarious center of gravity in her high-heeled state.

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suggestive4827 ai generated40633 prompter:horselover fat231 fluttershy3596 anthro14495 g434414 adorasexy751 big breasts6763 breasts16594 busty fluttershy1039 clothes14976 curvy1013 cute4484 female38250 heart914 high heels572 hourglass figure448 huge breasts2192 impossibly thin waist65 sexy4801 shirt1286 shoes1052 shorts564 shyabetes420 side view340 sideboob553 solo30779 standing1886 stupid sexy fluttershy658 tail7920 wasp waist49 white background734 wingless1737 wingless anthro1359

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Background Pony #8FCA
(Kinks: lactation, brainwashing)
“Hmmmm,” he said, glancing at his watch. “Well, we don’t have anything scheduled for this morning, do we Miss Shy?”
“No sir,” she said.
“Tell you what, hold my calls and we’ll set aside about fifteen minutes to deal with your little problem.”
“Th-thank you, sir,” she said, disappearing around the office door to set up the phone system at her desk to take voicemails before hurrying back in as fast as her dainty steps could carry her. The nanites had restricted her freedom of movement with certain stereotyped behaviors, such as only allowing her to walk with a shortened gait. Meanwhile, he retrieved an ornate glass from a hidden mini=bar in the office and brought it over to his desk.
“Alright Miss Shy, please step over here and take off your blouse. Wouldn’t want it to get stained.”
“Yes sir,” she said, heels click-clocking over the rich wooden floor of the office and undoing her buttons. Without hesitation, she let the blouse fall off her shoulders and slipped her arms free of it, revealing her naked breasts casually.
Her boss placed a hand on her back and leaned her forward, and she braced herself on the edge of the desk as he took up a close position behind her, careful not to tread on her new tail. He reached blindly around the sides of her enormous bust and felt gently for his targets. She shuddered when his fingers stumbled upon her expanded nipples, already growing stiffer in the open air. Gently he manipulated them, moving his fingers into position. Looking over her shoulder past the masses of billowing pink hair and limply laid-back ears, he checked his aim and firmly tugged her right nipple.
A thin stream of milk shot into the glass on the desk, ringing against the faceted walls of the vessel and dribbling down into the bottom before the stream gave out. He tugged her left nipple and the bloated mammary responded with a repeat performance, filling the glass with another few milliliters of warm, chalk-colored fluid. She shivered pleasantly in his arms while he cycled back and forth, pulling one then then other.
“Getting some relief?” he asked the buttery yellow secretary as he drained her at a leisurely pace.
“Oh yes, sir,” she said with a fluttery sigh. “I’m very sorry, I don’t know why this is happening all of a sudden.”
“Well that’s alright,” he said, falling into a rhythm of ringing the glassware with his living instrument.
“I mean… I… I’ve never… needed to… get milked before? I don’t… remember… even having… um…” she trailed off, and he felt her body stiffening up a bit. “I didn’t have… breasts before, did I?”
“Miss Shy, you’ve always been a very busty lady.”
“I… I’ve always been a very busty lady,” she repeated after hearing her spoken password.
“Miss Shy, it’s perfectly normal for a woman as developed as yourself to spontaneously lactate every now and then.”
“Perfectly… normal…” she recited.
“I dare say, Miss Shy, you seem to quite enjoy getting milked like a placid cow.”
“I… like… getting milked, like a… placid … cow…”
“It’s quite erotic, isn’t it Miss Shy?”
“Erotic…”
“Miss shy, you feel so comfortable, relaxed, and safe.”
“Comfortable. Relaxed. Safe.” Her voice was a dull, lifeless drone superimposed on easy, deep breaths.
“Miss Shy, I would definitely say you enjoy the romance and intimacy of being milked. It puts you in quite an aroused state, doesn’t it Miss Shy?”
“Yes. Aroused. Romantic.” Her head was lolling to one side and her body was loose in his grip while he continually tugged and pulled to gently ease her nipples open momentarily and allow the creamy fluid to escape. By now the glass was roughly a third full.
“So, what did you think of the other girls you met last night?” he said, curious to see how his conditioning had taken hold.
“Oh they were so nice,” Miss Shy said, slowly easing out of her password-induced trancelike state. “Mitzy was a little, uh, off? I guess that’s how I’d put it. Nice, though. Bunny was super cute.”
“Hmmm, yes, Mitzy is definitely a bit of an airhead. Oh, don’t worry about it, she’s been called that to her face before. She thinks it’s a compliment. Bunny, Mr. Lamont’s secretary, her actual name is Jessica Rabbit if you can believe that.”
“No way!” Miss Shy said. “She looked just like that character, too! What were her parents thinking?”
“Heh, you’ll probably find a lot of coincidences like that around here. It’s best not to think too hard about such things, Miss Shy.”
“Yes… sir,” she acknowledged, absorbing her directive with the password. “Um, anyway, they were all pretty hot weren’t they?”
“Smoking hot,” he agreed.
“I mean, I know it’s not professional to talk about my coworkers that way,” Miss Shy confessed, pausing to take a few luxurious breaths as her boss kept tugging on her breasts and filling the glass beneath her. “But man, the whole time I was thinking about how great they must be in bed.”
“No problem at all,” her boss said. “In fact, Miss Shy, I want you to feel perfectly comfortable talking about your sex life when we’re in private like this.”
“Yes sir,” she gasped, her arousal still gradually building. “I mean, to tell you the truth I really wanted to plunge my dick into both of them non-stop.” A concerned look slowly distorted her slack face. “My… uh…”
“Clearly, Miss Shy, you’re obsessed with cocks.”
“Obsessed…” she repeated, her tension melting as she internalized this new description of herself.
“Yes, Miss Shy, you love everything about cocks. You take great satisfaction in pleasuring cocks, Miss Shy.”
“Cocks…”
“Seems you’ve had a case of ‘penis envy’ your whole life, Miss Shy, and it’s perfectly normal for you to fantasize about having one yourself. But that’s all they are, Miss Shy, just fantasies.”
“Yeah… must be it. Just fantasies.” She moaned slightly and let her legs relax a little, bringing her plump rear to rest against her boss’s crotch.
“Well, this glass is half-full. Any more and we’d probably get milk all over my desk. Be a doll and empty this out, would you?” he said, releasing his grip on her breasts and picking up the glass to offer her.
“Yes sir,” she said, a little disappointment at the interruption. She took the glass from him and glanced around the office. “Um, is there a sink in here, or…?”
“Never waste good milk, Miss Shy. Bottoms up!” he prompted, miming the action of drinking.
“I… it’s just that I’ve never…” she stammered, regarding the glass of milk hesitantly. “I thought, well, if anything, wouldn’t you like to, uh, take care of it like you did last night?” she asked.
“Miss Shy, think about this: you need to recycle all those nutrients if your body is going to pump them out like this. Milk is good for you, anyway.”
“Huh, I guess I didn’t think about it like that,” she said. After a moment’s pause, unable to think around the logic of her boss’s statement, she brought the glass up to her lips and took a sip.
“It’s quite delicious, Miss Shy,” he said.
“Mmm, you’re right, sir!” she agreed immediately after receiving her password. She wasted no time knocking back the rest of the glass, finishing it off with a satisfied sigh. “Mmmm, a lot sweeter than I thought it’d be.”
“All taken care of?” he asked.
“Well, not exactly, sir,” she said bashfully. “I think there’s still some more to express.”
“Not a problem. Assume the position, Miss Shy,” he said, pointing to the desk. He watched with satisfaction as the topless, top-heavy secretary put the glass back on the desk and leaned over her, spreading her legs slightly to brace herself against their weight. He returned to his stance behind her, grinding against her a little bit and being rewarded with a soft giggle as he did so. He delighted in running his hands over her soft, heavy breasts again. “We’ll change tactics this time,” he said. Instead of tugging to release her milk, he stared squishing each breast in turn, forcing a more pressurized jet to stream out into the glass.
“Mmmmmm,” she moaned softly. “Thank you, sir. Sorry to be such a bother.”
“Oh it’s not trouble at all. Never worry about asking me for help with your milk, Miss Shy.”
“I won’t, sir.”
“In fact, if you ever need relief and I’m not available for some reason, don’t hesitate to ask Mitzy. You remember which secretarial dorm she’s in, right?”
“Yessir, the one three doors up and across the hall from mine,” she replied. “She wouldn’t mind, then?”
“Absolutely not. She’s quite attentive to the needs of all her coworkers, and you just know she doesn’t have enough brainpower to think anything of it.”
“Heh,” Miss Shy chuckled, “I guess not.” She leaned further back and pressed her butt against his stiffening dick, enjoying the reaction.
“In fact, she may just want to have a little extra ‘fun’ with you if things get hot. My advice, Miss Shy, is to let it happen. It sounds like you’re quite attracted to her anyway.”
“Yessir,” she said between breaths that were starting to turn into steady panting, timed to match the alternating pressure as her boss continued to knead her tits forcefully.
“How’re we doing now?” he asked after a few moments where the only sounds in the office were the soft ringing of milk against glass and his secretary’s increasingly heavy breathing.
“Good, sir,” she said, her voice quavering. “Um, it’s just that…”
“Yes? Out with with, Miss Shy,” he told her.
“It’s just that when I asked to be milked like you did last night, um, I meant the same way. Sir.” she blurted out.
“Ah, I see. Well Miss Shy, it seems you’ve got so much more milk this time. Let’s get a couple more glasses emptied out and then we’ll switch to nursing, okay?”
“Yes sir,” she said, relief evident in her voice.
He smirked and made a mental note to himself to adjust the rate at which his secretary’s body produced milk. He’d been a little too eager this time and may have bitten off more than he could chew, without interfering with his schedule anyway. While he was at it, he wondered if she would look even better as a tall and leggy babe, or even if he should knock a few more inches off her current height again. There was time to play around with the nanites before they became inert in a couple of weeks. He was sure he’d hit upon the perfect look for her by then.
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