Brenna at the Academy
Bdsm Story

Brenna at the Academy

by Spiceroute 17 min read 4.9 (22,400 views)
female submissive male dominant headmaster training spaning vaginal intercourse anal play role play
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This is Chapter 3 of "Brenna at The Academy". Reading all chapters in sequence is recommended for context and maximum enjoyment.

This series is a work of complete fiction and fantasy borne of the imagination. All characters and locations are fictional and any resemblance to real people, names, events or places is purely coincidental. All fictional characters are consenting adults having a good time, in safe circumstances.

* * * * *

Brenna sits in the student lounge and enjoys her delicious sushi treat. There are a few other women in the space, some alone, others grouped in twos or threes, talking quietly. A petite Asian woman waves and catches Brenna's eye.

"Hi, I'm Annie, also known as student 31..."

"Oh! Hi, we both, erm, won the oral challenge, right?" Brenna laughs finding this strange bit of common ground with her new acquaintance.

"I'm Brenna. I also think we arrived at the same time and were in the processing hall together?!"

Annie laughs and says:

"Yup, wasn't that a fun introduction to this place? Damn, I came so hard when that blond instructor hammered me! I actually think you were beside me with the hot Black one!?"

Brenna blushes and laughs.

"All true. This place is quite something, isn't it? Is it ok if I sit with you? I have to run soon, but just for a little bit,"

"Of course! So have you decided what you'll use your tokens for? I already violated the rules, so one is to make that go away, and I think it will be good to keep the other as insurance, since I think i'll be breaking more rules very soon, just give it a bit of time," she winked, "And besides, isn't that part of the fun, breaking these rules?"

Brenna points at her feast:

"This right here is where my tokens went. It's my birthday today and I thought I deserved a treat. Well, a food treat. This whole stay is a sort of birthday treat I dreamed up for myself, believe it or not. You know what I mean. I too have a transgression on file right now, but you know what, like you say, isn't it all part of the fun? I mean, even getting the

punishment

? If I'm honest, that precisely is part of the reason I came here..."

Annie whistles,

"Daaamn girl, too true! TouchΓ© about accepting punishment!...aaaand Happy Birthday!!! - I hope you get more treats today, everything you need and hope for...and deserve, as the Masters would say I'm sure," Annie suggestively wiggles her eyebrows.

Suddenly the overhead paging system goes off and Brenna startles as she didn't even know the place had one.

Trainee 73, return to your room before next scheduled event and do so with at least 15 minutes to spare.

What on earth?

"Crap, thats me! I guess I have to run earlier than I thought! See you later, Annie!"

The girl gives her a silly salute, and Brenna scarfs down the last of the very on point sushi, grabbing her cake to go. She has little time right now for giving in to her musings about how normal and how strange at the same time this exchange was. She decides to think of it like a conversation about house rules and events that two women might have at a fancy spa they are both staying at, except that, attire in this case is absent rather than limited to fluffy bathrobes. It helps a little to make it all more normal and palatable.

Arriving in her room, Brenna finds a note and clothes laid out on her bed.

For your Individual Instruction session, put on the provided items. Failure to follow these directions will result in punishment."

What around here wouldn't? Brenna thinks as she chuckles. Laid out before her are a very short, plaid kilt skirt, a white, fitted button down shirt, high heeled pump shoes, and some lingere. Wasn't one of the main rules here that trainees were to be nude at all times in the facility? Brenna finds herself inwardly shaking her head, as it is now apparent The Academy flexes its rules when it suits some instructor - the lawyer in her wants to correct the Orientation Guidelines document to at least add "...unless otherwise specified by an instructor." Mentally parking her lawyerly, pedantic need to correct, Brenna runs to the bathroom for a quick shower after this morning's exertions, realizing she has to hurry if she is to show up on time for her next scheduled event.

Having dried herself off, she puts on the lingere, and discovers it to be a black garter belt with thigh high black stockings embellished with lace, and a black lace shelf bra of sorts that pushes up her ample breasts but deviously leaves the nipples and most of the breast exposed. Brenna is flabbergasted that such garments even exist. Of course, there are no panties. She makes use of the full length mirror in her room for the first time and gasps at how provocative this ensemble is.

Brenna would not be out of place in a porn movie wearing this outfit. The garter belt and stockings perfectly frame her bare and exposed pussy and the "bra" does a great job of pushing her breasts up lewdly and making them look even bigger than they are, with areolae and nipples exposed and standing at full attention. After being stark naked for the last 18 hours or so, it is a wonder that any state of attire can provoke an even more sexual response, but this certainly does. Brenna thinks that she looks more provocative and exposed like this than when completely nude. The lingere is a lewd mockery of clothing, leaving all most private parts, open, exposed and even highlighted.

Next, she pulls on the actual clothes. The very short skirt, or rather, more like a lap belt that barely covers the garter belt, is a mockery of the Catholic high school kilt she grew up with. Its blue, black and white plaid, very much like the design of her old high school uniform and flares out from her hips. Brenna chuckles remembering some of the pervy male teachers becoming kilt police and checking the length of the hem with a ruler while getting a girl to bend over to see if it matched the school's standard for modesty - they would have a field day with this poor excuse for a skirt, and truly relish the measuring process, as she was sure that with bending down, this kilt would mercilessly ride up to reveal pretty much everything. She tests it out, just to be sure, and predictably she sees the ample cheeks of her ass in full glory staring back at her from the mirror. When she bends down all the way, her pink inner labiae and her glistening slit also make an appearance...Brenna feels flushed and her pussy tingles just from these visuals.

The shirt is super fitted and tight. Brenna decides to leave the top few buttons open. A short, black tie and black pumps with rather high heels complete the outfit. Brenna touches up her makeup, sure to use a lot of blush and choosing a girly pink lipstick shade. She makes her eye makeup dramatic, and in a burst of inspration, puts up her short, chin length hair into two mini pigtails. Britney Spears in the "Oops I Did It Again" video, eat your heart out!

With minutes to spare, Brenna rushes down the corridor and up the stairs and to the room indicated on her timetable for the location of her Individual Instruction. The door at the end of the hallway is closed and a name placard is affixed at eye level:

Mark Alcock, PhD.,

Headmaster

The Academy

She chuckles out loud thinking that can't be his real name, but at the same time she feels the slippery, hot cream in her freshly showered pussy drench her swollen folds anew. A bad girl coming to the Headmaster's office is pretty much Brenna's wet dream. The sexy, stern professor fantasy is one of her longest standing ones, surprisingly with some roots in real experience. James Brock, the visiting British sessional instructor at her college was the man who took her virginity in first year, and introduced her to the joys of spanking. Come to think of it, he was probably the most capable lover she has ever had and the all too brief May-December romancce they shared before he finished his term was pretty damn hot. Brenna's sex life started off promising, with a bang, only to quickly settle into mediocrity punctuated with lengthy dry spells of singledom. Life could be such a tease.

Brenna loiters for a minute, unsure of what to do, then knocks.

"Enter." Comes a deep, dry, gruff masculine voice from within.

Brenna takes a few deep breaths, trying to calm her heart rate and the throbbing in her pussy. She opens the door and walks into the room.

The room is a vast study or library, with nine foot ceilings and tall windows on the side and far back wall, that resemble stained glass church windows in shape, just like the ones in the grand lobby. Many bookcases line the walls of the study. The hardwood floor creaks a little as she walks on it, navigating the cavernous space, as if walking down a long aisle in the center to the back of the room, approaching the altar, which in this case is a large cherry wood desk with someone sitting behind it.

She pushes on deeper into the space towards the tall windows near the back end of the room. An oversized, vintage desk faces the long, open space of the room, a massive, sculpted wooden chair behind it poised like a throne to survey the whole chamber. On her side of the giant desk sits another smaller chair, upholstered in black leather.

"Miss Swansea. Just barely on time. Sit." his voice deep and edgy, he stands behind his imposing desk and motions to the small chair across.

Headmaster Alcock is a very handsome, mature gentleman in his mid 50s. He is tall and well proportioned, with a clean shaven, classically handsome face bounded by a strong jawline. He wears glasses and has an impressive full head of black hair, heavily greying into delicious salt and pepper colouring at the front and the sides. His piercing hazel eyes crackle with intensity, like scorching lava with an undercurrent of warm honey. He wears an impeccably tailored, softly checkered brown three piece suit, a crisp white dress shirt and dark brown tie. The collar is partly undone, the tie loosened, and curls of salt and pepper chest hair peek out from below. Brenna very much likes what she sees. Its as if the Academy creates these men by combining the sexiest features plucked from her mind. Maybe they aren't real but AI projections or holograms? Although they'd have to be pretty advanced ones given the very tangible tactile components of their interactions...

"I am Headmaster Alcock. You will address me as Headmaster, Professor, Doctor, or Sir." He informs coldly, while slowly pacing around Brenna's chair.

"Yes, Professor Alcock." She sits down gingerly only to hear him snap:

"No, not like that. Stand and sit again, this time with your skirt out of the way, your bare bottom directly on the chair. Girls like you, little Miss, need to finally drop the pretence of modesty you still hang onto."

"Yes, of course Headmaster, I'm sorry, Sir," Brenna swallows dryly and complies. The cool, smooth leather feels decadent against her bare flesh and she immediately feels some stickiness at the front of the seat, as her moistened folds make contact with the leather.

"I think we can conclude with confidence that your instincts have finally led you to the right place and you fit right in here at The Academy, Miss Swansea. Your instructors are quite complimentary:

Mostly obedient, spirited, eager, and a 'naturally submissive, enthusiastic trainee whose pussy positively leaks at first sign of impact play'

are some glowing terms they've used to describe you." He reads from the screen in front of him, smiling.

Brenna blushes beet red, but the compliments also make her feel very good...or like a very bad girl, which in any case is good, she supposes. Its hard to wrap her head around the seeming contradictions, but easy to feel her body responding with pleasure.

"Tell me, Miss Swansea, are there any questions you have about your progress here so far? Anything you want to ask or perhaps specifically work on? We take this opportunity in Individual Instruction for a little Academic Advising."

"Um...Actually, yes, Sir... my nipples are sometimes numb and only rarely when I play with them, of course more so here, do I get that wonderful shot of electricity into my clit. When I play with my nipples, they also often get too sensitive and bother me, not in a good way, for days afterwards. Is there some way to stregthen that nipple to clit connection, and to get my nipples to be sensitive more consistently but not too much so?"

"Mmmm...Ms. Swansea, you are a very reflective learner, I am so glad you asked. It's truly exemplary that you are already able to identify very concrete personal learning goals. Most students at your stage struggle with that. I will send you home with a training regimen to help work on these specific goals of yours. In short, you will do a daily fifteen minute exercise - five minutes of playing with your nipples, five minutes of playing with your clit, and concluding with another five minutes of playing with both at the same time to build and strengthen the neural connection. You might," he laughs, "...need some help with the last part as it may be a tall order with only your two hands available. A clit vibe, or nipple toys will do the trick. The daily teasing will toughen up your nipples, so to speak, so that uncomfortable sensitivity will lessen. The exercise will condition your nipples and clit to connect more fully as you desire."

"Oh, wonderful Sir...Also, I know I haven't been here for very long, and the novelty and sheer amount of stimuli are all doing their work, but I can't believe how aroused I constantly am since I got here compared to my baseline at home, and how frequent and big the orgasms I am getting here are compared to my norm. Is there some way to retain some of this state in my daily life, short of spending 24/7 thinking about or engaging in sexual acts? Most unfortuntely, that approach would be highly impractical."

"Certainly. Your enthusiasm for ongoing learning is exemplary, Miss Swansea! We can prescribe a regimen of...certain basic exercises to do at home between your visits that will help, as you wish, with maintaining the gains you have made here. If we go ahead with this, we do like to keep track of your practice." He passes her some paperwork and a small Apple electronics box.

"You can wear it as much as you like, the more the better in fact, as we get more data, but the absolute minimum is to wear it, along with a stick-on removable sensor which is also in the box that you will attach to your clit, during your daily exercises. Besides the modified tracking capabilities, it works just like the latest model of Apple Watch, with all the features - enjoy the device!

We've already talked about the nipple work, and strengthening the nipple-clit pathway, and there will be at least 15 more minutes daily of stimulating the body, mostly your hot little pussy. There is good evidence that daily masturbation and toy use leads to more powerful orgasms and can properly maintain that wonderful, overactive slutty sex drive of yours. Before you think of all the hot orgasms you will now constantly have, let me orient you to the fact that the point is daily regular stimulation, but NOT daily climaxing while you play. Climaxing too often on your own can dilute the tension we are trying to build and keep constant, make the orgasms you do have feel weaker, and is generally not recommended for wanton bad girls such as yourself, who need a more...disciplined approach."

"Oh! I see, Sir..."

"On the home practice regimen, you can cum from playing every three days at most, so that means if you make yourself climax on a Sunday, you're next allowed to orgasm when playing on Wednesday, at soonest. Disregarding the prescribed frequency will be recorded and of course will lead to...consequences when you next return to The Academy. Adhering fully, long term, to the regimen, on the other hand, leads to attractive rewards when you next return...Climaxing during penetrative partnered sex is exempt, to encourage your sexual liberation in daily life. So if it's cock in pussy or in arse when you climax, allowed frequency is unlimited. Bear in mind that a man's fingers, mouth or tongue, or a toy, in pussy or arse qualify as playing, not penetrative sex, so the three day rule applies. You can circumvent that by holding out your climax during those other activities until partnered penetration of course. At discernment, you will make the final decision as to whether you accept the challenge of home practice, and consequently being liable for omissions, and eligible for rewards."

"Yes, Sir, I understand, Sir. I think the home practice is a fantastic idea,"

Brenna absorbs all he says and feels her pussy clench and her pelvis heat at the prospect of home practice and having limits set on cumming from masturbating. She loves the idea of working towards bigger orgasms and taking some of the fun she has discovered here home with her in a more structured way. She thinks the sex exception is very generous and that she needs to get her hands on a man, or rather, a man's hands on her, or both, to take advantage of it. With how busy she was at work, and how depressing her life recently has been, Brenna was currently single and hadn't had sex for months prior to coming here.

"Remember that technology doesn't lie and cannot be fooled, my sweet, the system is precise in approximating the time and method of your last orgasm and uploads that information daily when you put on the watch for your exercise. Believe it or not, it can tell if a hot blooded man was involved ehm, deeply enough, so to speak, in your climaxing. Each week, the device will ask for you to confirm your consent for continued participation in the home practice program. You can withdraw consent any week, and there are no consequences, you simply forfeit all rewards and punishments alike accumulated through the program. We understand having ongoing intensive home practice requirements isn't what all students need or can accept."

He rises again and prowls around her chair.

"On to more pressing concerns. I have report that last night you disregarded and willfully contravened clear direction given to you. Will you tell me more about that, Mizzz Swansea, and tell me what you think we ought to do with that matter?"

"Yes, Sir, I...This girl was bad, and naughty and made herself cum in bed last night despite clear instruction from a Mistress to play but not orgasm. This girl sincerely hopes the Headmaster can discipline her for this blatant disobedience, to teach her a much needed lesson..." Brenna purrs, looking coyly at the ground and squirming in her seat.

"In that we certainly agree. What were you thinking of as you came last night, Miss Swansea? What was your fantasy?"

"Oh just a silly fantasy Sir..."

"You will answer and be specific girl!"

"Yes, Headmaster. Sorry, Sir. Um, I imagined being with three of the instructors I met last night, all at once. I imagined the Masters, um, I think its called,

doubly penetrating

me,"

she says tentatively, her coy voice betraying the newness of the activity and the term to her, and her face beet red again.

"...and at the same time, being ordered to pleasure the Mistress orally."

"And how did you bring about your release?"

"Oh...um...I was masturbating, Sir, fast and hard..."

"Girl, don't be daft, anyone would gather as much, I am asking for specifics. How?" he spits out impatiently while regarding her with an intense stare.

"...Oh...I teased my nipples with nipple ties, self-spanked my butt a lot and my pussy a little with a paddle of sorts and then used a large purple vibrator, and my fingers, both in my pussy, and on my clit of course, to climax..."

"And

that

is precisely the minumum level of detail you need to be using to explain such matters going forward, understand?"

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