Ch. 1: Cougars into MILFs

A/N: To be honest, this entire thing sparked from Ch. 3 of 'A knight and his maidens' by Azure megacyber. There wasn't any Preg!Glynda that I could readily find or anywhere near enough Sword and Sorcery to be found. So, here we are with me trying my hand at it. It might seem a bit accordion shaped in turns of time but that's just because I'm trying to set things up for the main act of the story. Let's hope for the best eh? Little bit of musical inspiration from Miracle of Sound's 'Jet Black Dress'.

E/D: I really don't like 'A knight and his maidens' since I see it as both a mediocre story and a fairly lackluster attempt at smut. If you want a better Jaune x Glynda story with smut I recommend 'Taboo Sparring' by Whynoteh, it's FAR better in my opinion.

Dust, I don't know how I got here... actually, I suppose I do.

Always had a fetish for older women, their maturity, their grace, their fully developed bodies, their lack of need or want to beat around the bush about what they want. Sounds like a perfect woman to me, but Dad kept telling me that I needed to chase after girls around my own age, something about getting experience.

Mom was supportive though...

But I tried, I tried really hard, using all the lines that dad taught me, staying confident, everything, but it both didn't work and just showed me how boring women my own age can be comparatively.

After that, I went to Beacon, new group of girls to give it one last go before I just swore off it til I was older.

Then... then I saw her. I saw the woman of my dreams, the tall, elegant, busty, and drop dead gorgeous Glynda Goodwitch. She hit all my buttons at once.

Tall? Check.

Glasses? Check.

Busty? Check.

Short blonde hair? Check.

Curves in all the right places? Check.

Piercing green eyes like clear cut emeralds? Oh yes check.

Waaaaay out of my league? An unfortunate and definite check.

I was smitten at first sight, barely even hearing what she said in that first assembly. I could do little but gaze upon her beauty, the sway of her hips, the sternness in her eyes, she was perfect and I desperately wanted her, but at the same time, I knew she was far beyond my level.

That didn't stop me from trying though...

It started small, classics, just like dad taught, an apple on her desk during the first class. She didn't eat it, but it wasn't wasted. Hurt like crap when it hit me in the chest though.

Next attempt, maybe she didn't like apples, a doughnut though, who doesn't like doughnuts? Again she threw it, though that time it hit Cardin, so I was able to maintain my secret admirer status.

Flowers, candy, romantic notes and cards, all the old gold ones my dad taught me and even a few new ones I came up with on my own, like a ticket to a symphony, just so I could see her smiling a little the next day... that was actually the only success, the others were thrown away or used as missile weapons against disrespectful students.

Finally, months into our first semester, I was running out of ideas and had a sit down with the only male friend I had, Lie Ren, and I told him the situation without naming names. He listened to the whole thing with his usual impassive gaze, nodding to indicate that he was still listening, and occasionally asking a question every so often.

When I finally ended the long spiel of my failed love life, he sat there for a moment, staring off into space before his eyes snapped to meet mine. "Alright, Jaune. Tomorrow, when you see her, you need to ask her out."

"What?"

"No beating around the bush, simply ask her out on a date. You seem to know her favored activities, try asking her out to another one of those."

"B-but that... that can't be all there is to it!"

"I don't see why it couldn't be."

"B-but."

He cut me off before I could sputter anything else forth, clamping a hand over my mouth. "Listen, tomorrow's your birthday, correct?" I gave him a nod before he continued, "Ask her out, and if she says no, I'll buy you a cake, okay?"

I started to give my well thought out and persuasive counter argument, he only arched a brow, silencing me once more. My body sagged in defeat and I nodded, mumbling an affirmative before he removed his hand, wiping it gently on my shoulder.

"Now, study up, we have a test in Goodwitch's class tomorrow."

A test in more ways than one...

The next day came all too soon, simultaneously racing through and dragging on to its conclusion. An eternity and an instant later, the final end of class bell rang through the academy, signaling our release from the responsibilities for our coming weekend.

And signaling that showtime had finally come for me. The door to her classroom had never seemed so imposing, normally it's just another door to run through in a hurry right before the late bell would ring. Now though, now it felt like a massive barrier to be overcome, a huge, daunting obstacle.

With a deep breath and a shaky step forward, the simple wooden blockage opened, barely making a sound as it swung into the empty classroom. Empty but for the blonde haired beauty seated behind her wide wooden desk, grading several papers spread before her. I gulped as I walked down the steps slowly, trying to keep quiet, almost afraid that any undue noise would shatter the moment entirely.

I reached the bottom ring of desks before she spoke, her smooth voice caressing my ears yet bringing on a dark pit in my stomach. "Yes Mr. Arc? Can I help you?" Her eyes didn't rise from the papers, jotting a few more notes onto one of them in her delicate, beautiful script.

My mouth went drier than I'd ever felt, my veins going cold, "U-uh... I-I... ju..." was all I could mumble out.

"Speak up Mr. Arc, I can't hear you."

Dragging air into my lungs once again, I forced out the words that rattled around my head. " willyougoonadatewithmetotheValeSymphonicOrchestraconcertthisSunday!?

Her pen stopped moving as she finally looked up from the papers at me, her piercing emerald eyes meeting my cobalt ones. "What was that?" Each word rolled off her tongue with a sharpness I'd not experienced before.

The shaking in my knees was impossible to stop, "M-ms. Goodwitch, will you go on a date with me to the Vale Symphonic Orchestra this S-Sunday? I-I have two tickets and I know you like them."

A small blush actually crept upon her pure cheeks as she sat there blinking at me, before she attempted to regain her composure. "Mr. Arc, attempting to bribe me will not raise your grades."

"I'm not trying to bribe you. I genuinely want to take you on a date Ms. Goodwi-Glynda."

The blush brightened a little and she seemed a little more thrown off. "It was you, you were the 'secret admirer'?"

My own blush crept to match as I looked down at my shoes, "Y-yes ma'am. I realize that a beautiful woman like yourself probably gets asked out quite often, so this probably doesn't mean much and I'm sorr-"

"I don't."

I looked back up at her, her face softened as the blush was now apparent. "W-what?"

"I don't get asked out a lot, or at all."

My jaw dropped, "No! That can't be true, a stunning, perfect woman like yourself should have a line of men around the corner!" No sooner had the words left my mouth that I realized I might have gone too far and squeezed my eyes shut, just waiting for the punishment to end all punishments.

When no such blow was forthcoming, I opened my eyes a little. Glynda was still there, her eyes wide and a hand was covering her mouth as the blush was deepening across her face.

"T-then please, let me be the first to court you then!" I blurted out, almost regretting it as her eyes grew wider than saucers.

"W-we couldn't..." She coughed, trying to put her stern mask on once again. "It wouldn't be proper, you're underage after all."

"Not as of..." I glanced down at my scroll, "14 minutes ago. I'm officially 18."

It looked like her defenses were beginning to crumble. "W-well, you're also my student, there might be calls of favoritism."

"Then train me extra hard. Throw me into all the combat tests! Wear my body out!" Too late...

Her face turns beet red, "F-fine... if it will make this cease, I will go with you to the Orchestra."

I felt as if I were light as a feather and my heart would explode from my chest. "Thank you Glynda! I'll see you Sunday at the airship docks then!" I quite literally skipped away, leaving the stunned older woman behind me to contemplate what just happened.

I immediately went and told Ren that she'd said yes, he'd looked relieved until I said, "Guess you don't have to buy a cake!" in front of Nora. He ended up buying a cake anyway because of her.

The date itself went wonderfully. I had a nice suit that my parents got for me 'just in case', but Glynda... she showed up in a long, flowing, jet black dress with a brilliant pearl necklace that contrasted perfectly against it. I had a reason to stifle my air sickness and only dry heaved a little when she wasn't looking.

The Orchestra performed spectacularly, as to be expected, and Glynda seemed absolutely delighted while we were there. I did my best to be a perfect gentleman, and everything seemed good. Then we got back and it was clear that the pleasant night had lowered her normally stern nature a little.

"That was quite pleasant, Jaune. Far nicer than I honestly expected."

"I'm glad you enjoyed it."

Her face reddened a little as she coughed awkwardly. "I will not say that this could be a regular thing," I felt the smile falter from my face a little.

"However, I will not say that it cannot be. Should it, you would be trained much harder in class, even though absolutely no one would be allowed to know and if anyone asked I would deny it."

The wonderful night had torn down a few of my walls as well. "Deal. For such a drop-dead gorgeous woman such as yourself, there is nothing that is 'too much'." And to add the cherry on top, I took her hand and placed a gentle kiss upon the back.

Her mouth dropped once again just as the transport Bullhead landed with a dull thunk, opening its doors to allow its only two passengers to leave.

Glynda coughed once again and took her hand back, her face a brilliant crimson. "W-well then, Jaune... I believe I will see you tomorrow morning in class."

"Of course, Glynda. Have a nice night."

"Y-you as well." She tugged her dress up a little in her hands before walking briskly out of the transport, leaving me to jump and click my heels in delight.

More dates followed, though she said that things would go 'Agonizingly slowly' but never gave a reason. Our dates were always in secret or carefully managed so that we wouldn't be spotted. Meanwhile, my training in her class got stepped up, though what that translated to was less 'Lots of fights' and more 'I get tossed around the room like a freaking rag-doll'. Though, as the weeks and months went by, with both class and Pyrrha's training, I was definitely making a lot of progress and even starting to hold my own in most fights.

On our 6th date, I got my first real kiss rather than one on the cheek or forehead. A quick, chaste affair, but lip to lip contact nonetheless, and it left both of us rather blushy. That day was the day she said that I was allowed to say we were officially dating, in private at least.

By the 6 month mark, summer was approaching and I knew the two of us would finally have time to ourselves, one way or another.

The summer was over all too quick, bringing us back to the academy, this time with me as a 2nd year leaving the two of us without even combat class together anymore, though we still found time to be together and cuddle if nothing else.

My 19th birthday approached quickly, a week before it Glynda told me that she knew what present she would give me...

She came into the room after having sent everyone out on a long errand, her eyes showing her sultry intentions as her top came off. When I had asked about protection when she had forced me onto the bed, she said that she knew I was a virgin and that her protection would last for several more months before she needed to replace it. Then my thoughts got fuzzy when her bra fell off.

I want to say our first time was magical, that our bodies entwined perfectly and that her screams of passion could be heard throughout the halls... I want to say that, but honestly, I elbowed her in the face and popped after thirty seconds. It was not my proudest moment...

She understood though and quickly brought me back to attention before the two of us went at it a few more times. I think Ren was the only one who noticed the scent when my teammates returned and he just shot me a knowing glance, to which I could only shrug.

From there, things only got more hot and heavy. Turns out, she's a dom in both daily life and in bed. The two of us continued our secret rendezvouses until summer was upon us once again... at which point I swear I passed out from dehydration and exhaustion more than once, even with Aura helping out.

Then year 3 began, we'd been dating for a year and a half now...

We were exiting Advanced Grimm Studies, our final class for the day, when my Scroll went off. Opening it, a voice message began to play, Glynda's voice coming over the small speaker. "Mr. Arc, please report to my office as soon as possible." It clicked off right as the message ended.

Ren arched a brow, "Sounds urgent."

Nora piped up after him, "Wow, still getting training from Ms. Goodwitch? Geeze Jaune, I'd swear you spend more time with her than with us!"

Pyrrha was the last one to interject, "Though it has been helping, Nora, especially alongside my training."

"Yeah... I'll catch up with you guys later." I slung my bag over my shoulder before turning on a heel and jogging off to my girlfriend's classroom and office, leaving my team behind me, rolling their eyes.

The familiar door gave way, letting me into the room I knew well from more than a few naughty rendezvous with the tall, busty blonde.

The normal silence of her office was broken, however, by the sound of soft, constrained sobs. The thought that she might be hurt sent adrenaline coursing through me. I dropped my bag and took a short running leap down to the center of the room, rolling with the impact and trotted over to her desk, where the sobs were coming from her turned chair.

"J-Jaune..."

"What is it my sweet?" She spun the chair to face me, her hair a mess and her eyes bloodshot. "Who did it?!" I growl out, "I swear to Dust I will end them!"

A small plastic tap draws my eyes down to her desk, where she'd thrown a thin white stick, with two long pink lines near the end of it.

"Jaune... I'm pregnant."

A/N: Might make a side/separate/prequel thing that has more of the details of their relationship before sudden Preg!Glynda, but for now onward with the pregnancy and hijinks thereof! Little cliché delivery there at the end, sorry for that. May the night see you safe and the dawn greet you kindly my dear readers.