A Little Dash Will Do
Chapter 15: Headmistress Lessons
-by Drace Domino

“Twilight, you really didn’t have to wear the old uniform.” Principal Cadance chuckled a little, leaning back in her chair and looking at the young woman sitting across the desk from her. “You’re a Canterlot High student now, there’s no dress code.”

“I know, I know, but…” Twilight Sparkle fidgeted a little, her hands wrapping around the bottom edge of her schoolgirl skirt and giving it a little tug. It always did feel short, and especially after having not worn it in so long the thing felt particularly revealing of her smooth purple legs. “It felt a little weird coming back without it, even if it’s only for a visit. And I was hoping it’d help me blend in so none of the other girls realized it was me. I didn’t want to start any trouble for you.”

“Well, trouble isn’t something we have a lot of now that Principal Cinch has moved on to her next job.” Cadance smiled, though pointedly kept Cinch’s current role to herself. The school board wasn’t very happy after the events of the Friendship Games, and Cinch’s dismissal was a messy affair. Nowadays Principal Cinch was busy managing a convenience store, and Crystal Prep’s faculty would be content to never hear from her again. “What can I do for you today, Twilight? Is this something about Shining Armor?”

“Well...Well, no. I mean, yes. But mostly no.” Twilight Sparkle fidgeted again, and bit down on her bottom lip as she tried to find the words. “I’m really happy you and my brother are engaged. You’ve always been so good to me, and I know Shining Armor will treat you like a queen. And he’s just so in love with you.” She smiled, and similarly watched Principal Cadance beam with pride at those words. “But...well...you’re my future sister-in-law, and I...well, I need some advice.”

“Some advice?” Principal Cadance’s pretty, mature features turned to a thoughtful expression. As the youngest principal Crystal Prep had ever had, she was enormously popular with the students thanks partly to her beauty and partly to the fact that she never turned them away. Unlike the past principal, Cadance’s door was always open and she always wanted to help...even when the student wasn’t even one of hers anymore. Principal Cadance smiled fondly and stretched a hand across the desk, offering it to Twilight Sparkle in comforting fashion. “Anything, Twilight. I am always, always here for you.”

Even the mere act of stretching her hand out and folding it into Cadance’s made Twilight feel better, and she gave a long, wistful sigh. Who could possibly be sweeter than her future sister-in-law? Could Shining Armor be any luckier than to have her as a wife? Could Twilight be any luckier than to have Cadance joining the family? She smiled fondly at the older woman while her free hand adjusted her glasses, and she spoke up with a careful voice.

“Well, you see...recently, my friends and I stumbled across...well…” She took a deep breath, trying to figure out just where to begin. “I...sheesh, this is awkward. We found-”

“Let me guess.” Principal Cadance chuckled, and closed her other hand across Twilight’s. “Magical amulets that give you penises? And they squirt a taste that you just can’t get enough of?” She merely laughed softly at the sudden, shocked expression that crossed Twilight’s face, and gestured towards one of her desk drawers. “Twilight, I’ve had to confiscate two of them this week alone. I appreciate you and your friends doing something nice for our girls, but...well...as much as I love my students, they’re not exactly masters of impulse control. I had to take them away when I found Indigo Zap and Lemon Zest for lack of a better word ‘spitroasting’ Sunny Flare. In my office. During school hours.”

“...oh geez, Cadance, I’m so sorry.” Twilight’s hand moved from her glasses to flatten against her face, and her shoulders slumped. “We made them promise to only use them after school!”

“It’s all right, Twilight, you couldn’t know.” Principal Cadance laughed, and finally released Twilight’s hand as she leaned back. Her fingers folded just underneath her chest; a modest affair contained within the confines of a professional blazer. Cadance almost had a Principal Celestia style about her - perhaps younger and even more beautiful, but the same warmth and kindness Canterlot High’s top educator exuded came from Crystal Prep’s. A stark contrast to the old days. “So did you need advice regarding the amulets? Because my advice would be to only give them to my students on the weekends.”

“Well, yes. But...also no.” Twilight swallowed nervously, and fidgeted once more. “I mean, that’s good advice, but...the real reason is that I’m...I’m sort of...uh…” Truth time. Could she make these sorts of confessions to a woman she admired so much? “Well...I’ve been playing with them, too. You probably guessed as much. And I guess I’m worried that I’m not doing it as well as everyone else. When Pinkie Pie or Sunset Shimmer...when they put it in their mouth they seem so confident. They don’t hesitate, they don’t second guess themselves. The entire time I’m doing it I wonder if I’m doing it right, if I’m paying enough attention to everything, it’s just…” She gave a sigh, and looked over the rim of her glasses at Principal Cadance. “...I’m just worried I’m messing it up. And I was wondering if you had any...you know. Any tips?”

“Tips that I might have used on your brother?” Principal Cadance smiled wide; her grin stretching from ear to ear at her amusement. It was practically impossible for Shining Armor to have a cuter little sister, that much was sure. Cadance gave a little chuckle as she watched a deep purple blush erupt on Twilight’s face, and she let one of her hands lower to the nearby desk drawer beside her seat. “Well, Twilight, it’s a little hard to explain. But...I think I have a solution, if you’re willing to try.”

“Oh, anything!” Twilight Sparkle nodded, bracing her hands at the edge of the desk and eagerly perking up. “Please, Principal Cadance?! I just...I want to know I’m doing all I can for my friends!”

“In that case, I’m a firm believer of ‘show, don’t tell,’ when it comes to teaching.” And with that, Cadance drew her fingers out of her desk drawer, and dangling across them was one of the confiscated amulets. Twilight Sparkle could remember making that very same amulet with Sunset Shimmer; a gift for the Shadowbolts. Now she stared at it with wide eyes, realizing that it would be used in a very intimate lesson. She nearly fumbled it when Principal Cadance threw it across the table to her, and swallowed nervously as the older woman started to stand up. Principal Cadance’s voice pierced the air between them, giving her a gentle and friendly order if her education was to proceed. “Put it on, Twilight. I’ll show you how I suck your brother off, and once you learn my technique you’ll be the most popular girl in school.”

Twilight Sparkle did exactly as she was instructed even before she processed it all. Her trembling fingers looped the amulet over her head, and instantly she could feel the magic surge within her. By the time Principal Cadance went over and lifted up Twilight’s skirt there was a large bulge pressing against her panties; the perfect thing for Principal Cadance to witness the power of the strange magical relic.

“Oh, wow, it’s...it really works!” She chuckled, and lowered her free hand to slide a finger across the bulge in Twilight’s panties. “I mean, I knew it worked after catching what they were doing to Sunny Flare, but...well, to see it take place so fast? It’s impressive.” She beamed, and gazed fondly at her dear former student. “You know, as your future sister-in-law I should do the responsible thing and give you a speech about playing around with magic. But...I can only really give you one lesson at a time, and you asked for advice on sucking cock first.”

“Are...are you really going to?” Twilight asked with wide eyes, but a clear hope in her voice. As if to help facilitate it she pulled her panties down; just enough so that her throbbing purple length flopped out and her sack hung over the edge. She sat there with her member exposed and her skirt riding at the base of it; looking nearly fully clothed save for the impressive length clearly wanting attention. She shivered as Cadance moved a hand to take it within her grip, and watched in fascination as the older woman started to kneel before her. “What about Shining Armor? What about...you being a teacher?!”

“You’re not a student at Crystal Prep anymore.” Principal Cadance offered the second answer first, and gave a little shrug. Soon her professionally-dressed physique was kneeling before Twilight, and she pushed one of her palms to the inside of one of the teenage girl’s thighs to help slowly spread her legs. “And I’m sure Shining Armor would understand if I’m helping out his little sister. Let’s...just not tell your parents.”

“...I can safely say that will never come up.” Twilight Sparkle responded in nearly a deadpan tone, just before she shivered once more from Cadance’s proximity. The older woman beamed as she began to work, her fingers moving up and down that throbbing purple member. She didn’t forget the point of the moment, and as she traced along that lovely shaft she spoke up in a sweet, yet thoughtful voice.

“Now, you can tell it’s sensitive all over, but there are certain spots that are more noticeable.” She smiled, sweetly. “If I purse my lips and give a tiny blow right across the tip-” Twilight visibly twitched as she did just that. “-it sends a bigger stimulation than if I did it anywhere else. But physical stimulation is only part of it - mental stimulation plays just as big a roll. So while your body won’t respond as deeply when I do this-” And with that she tilted her head and pursed her lips once more, just enough to give a faint, tender kiss on the side of Twilight’s cock. It didn’t have nearly the shockwave of pleasure associated with it, but the sight of her beautiful features smooching the side of that thick shaft was enough to make Twilight whimper even deeper. “-your mind makes you more susceptible to future stimulation. This applies to both auditory and visual stimuli. Could you give me an example of something I could say that would make you more sensitive to further contact?”

There were few ways to get Twilight as engaged in a sexy event as making it into a test, and Cadance knew her student well. Twilight would be utterly honest if she thought it would give her a passing grade, even if it was embarrassing to admit. She swallowed nervously, and with her imagination spinning she spoke with a clear voice as if she was giving a presentation in class.

“Praising the length and girth of my magically enhanced member is a reliable way at offering a base level of auditory stimulation.” She admitted, a faint blush lining her cheeks. “But for deeper stimulation along the lines of a high risk and high reward scenario, comparisons to my brother’s...uh...unit would carry significant weight.”

“Ohh, so you want to hear me compare your big, thick cock with Shining Armor’s?” Cadance cooed, and teased her fingers down Twilight’s sack, playing tenderly with that little purple pouch. Once more she kissed the girl’s shaft, though this time allowed her tongue to work slowly and smoothly from one side to the other. Everything was slow and patient for now, the better for Twilight to take in the lesson fully. “He fills my mouth up pretty well, but...I think you might give him a run for his money. Yours has a softer texture...makes me feel like it’d be smoother inside of me.” Another kiss, but this time it devolved into a slow, long lick that left Twilight shivering once more. In the aftermath of that pleasure Principal Cadance gave a tiny whisper, her breath ushering a chill across the wet mark she just left. “Yours tastes better. Sweeter. Shining Armor’s cock is a fulfilling, healthy meal. Yours is a tasty, decadent dessert. I know I shouldn’t take another taste, but I just can’t help myself...and this ice cream cone isn’t going anywhere.”

Another lick. Another desperate moan from Twilight’s throat, and the girl’s knees spread a little further apart. She was already putty in Principal Cadance’s hands, and the woman was already working slowly and carefully so as to not overload the girl’s senses. Never did she think she could boast of her cocksucking skills to her future little sister, but...she was sure glad the topic found a way to come up. Principal Cadance smoothed her tongue up and down every part of Twilight, licking and kissing and even nibbling against the girl’s shaft, and every now and again she continued with her tips. All of them careful and precise, all of them whispered with a building lust.

“...remember to take a break from the cock sometimes, and give a soft bite at the inside of the thighs.”

“To give your partner a little surprise, try licking underneath the testicles, riiiiight here~”

“Always keep eye contact when you can. Let them see in your eyes how much you love going down on them.”

All of those tips came alongside an example, and poor Twilight Sparkle was blushing wildly with pleasure overwhelming her. She gasped and groaned and shook in place, and her tip constantly dripped little samples of pre as Principal Cadance slowly worshipped her cock. She was trying desperate to retain it all, but was already realizing that she should’ve brought a notebook to jot everything down. Perhaps her teacher wouldn’t mind giving her a follow up lesson? Or at the very least, an exam, to see what she learned!

“All right, Twilight, time to teach you my favorite trick. Are you ready?” Principal Cadance asked, and took Twilight’s gasping whimper as a sign of agreement. She chuckled fondly as she pulled her head forward, and prepared to wrap her mouth around the girl’s tip. “I’m going to make you cum for me, and I’m sure in the past your friends have either cum all over your face or just shoved themselves in as deep as they could. Is that right?”

“Yesmmmphhg.” It was the most the poor girl could offer in response.

“Well, don’t let that happen next time. When they start to cum, just...do...this.”

And with that, Principal Cadance unleashed her secret weapon on her former student. In order to get Twilight to the point of release she sucked her down with a few warm, wet strikes of her mouth, and her fingers moved to meet her lips so she could do it in perfect tandem. Up and down she bobbed her head on Twilight’s length, savoring the taste of her future sister-in-law’s cock with great enthusiasm. When Twilight’s orgasm nearly began Principal Cadance unleashed her special technique, and just when the girl started to squirt she pulled her head up to wrap her mouth fully, and only, around the tip. Her hand kept pumping up and down that wet member but her lips remained steadfast, making sure that only the tip of Twilight’s cock was given the pleasure of her warm, wet mouth.

And with a coy smile, Principal Cadance’s tongue slithered forward and pressed flat against the tip of Twilight’s cock. The result was an orgasm that brought her cum to ooze out rather than shoot; the older woman’s tongue serving as a stoppage that slowed its pace from her tip. Twilight Sparkle couldn’t cum a few quick squirts and be done with it - she could only sit there gasping as her cream pulsed within her only to seep out in between the seam of her cocktip and Cadance’s tongue pressing flat against her. It only extended the girl’s orgasm for a few sweet seconds, but seconds in such blissful joy were precious. As the cum slowly oozed out Principal Cadance’s mouth filled more and more with cum, and though she could very quickly realize why the Shadowbolts loved it so much she remained focused on her duties.

When Twilight Sparkle finally finished Principal Cadance pulled her lips free, and held her mouth open wide so the girl could see the mess she made. Her future sister-in-law knelt there as a cheerful helper, her tongue sweeping back and forth within a tiny sea of white completely contained within her lips. Twilight Sparkle gazed past her lenses to the beautiful sight before her, and with her cock still twitching and spasming in the aftermath of an intense orgasm, finally gave a staggered whimper as she crashed from her chair down to her knees.

Perhaps it was a bit bold to kiss her soon-to-be sister so passionately, but the flavor of that cum was too much to resist. The schoolgirl knelt there with her tongue probing the older woman’s open mouth, wrestling her tongue against Cadance’s own as they shared the flavor of the sticky white cum. Principal Cadance merely chuckled fondly and held Twilight close throughout; petting her fingers down the back of the girl’s hair and letting her enjoy all she wanted. When the cum had all been swallowed up by one or the other Principal Cadance finally pulled their lips apart, and fondly gazed at the younger woman.

“There.” She cooed, and licked her lips pointedly. “Did you learn a lot?”

“I did.” Twilight gasped, her cock still sticking straight out from her lap, desperate for more attention. “But I...think I might need more lessons, Principal Cadance. Just to make sure I remember it all.” Principal Cadance merely laughed in delight, and gave her dear student a doting, sweet kiss on the cheek.

“Next week, then.” She offered, sweetly. “Just remember your homework: suck off three of your friends using my technique by then.”

Twilight Sparkle beamed, and gave a joyful nod as she hugged Cadance against her. She was a good student and officially had a great teacher...and that meant her friends were going to be scrambling all over each other for a chance at her mouth. When they asked where Twilight learned to be such a good cocksucker, she would proudly say that the headmistress of Crystal Prep showed her how.

The good one. The bad one was off somewhere cleaning a Slurpee machine.

End of Chapter 15.

Author's Notes:

Who wouldn't let Cadance give them blowjob lessons? Only a crazy person, that's who.

Hope you all have a delightful New Year! If your resolution is to support more smut peddlers, maaaaaaaay I make a suggestion, darlings?