Brenna at The Academy Ch. 03

Literotic asexstories – Brenna at The Academy Ch. 03 by SpiceRoute,SpiceRoute
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! Touché 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?”

“Yes, Sir.”

“So help me understand, Miss Swansea, you fantasized about double penetration, which we sometimes call DP for short, but you didn’t actually try any anal penetration last night…?” He cocks his eyebrow quizzically at her.

“That is correct, Sir…This fantasy is powerful but very new to me, I only learned about this possibility at processing hall here, and I am not sure yet…Nothing and no one has touched my ass hole in a sexual way ever before, and at this time anal sex is one of my limits I don’t want to cross.”

“I see. That is quite the predicament, Miss Swansea. I suggest you give this internal conflict more reflection…It is a shame your limit is preventing you from exploring something you found so irresistibly arousing…

In any case, you have asked for your punishment and you will receive it now. Stand and move right up to the middle of the desk. Leave your new watch on the desk here for now. You’ll retrieve it before you leave today.”

Brenna sighs audibly and rises, moving close to the desk. She puts her new watch and the paperwork on the side of the desk. Headmaster Alcock cranes his head up slightly and a look of judgment crosses his face.

“No, first I actually need you to turn around, look at the chair and tell me what you see.”

Brenna does as instructed and begins:

“Mmm…this girl has left a horny wet spot of pussy juice on your leather chair, Sir…”

“Correct. You are required to clean up after yourself, Miss, using your mouth. Don’t move from where you’re standing. You would benefit from putting your legs apart a bit, for balance as you bend down…”

Brenna spreads her legs and bends forward to lick the chair clean. She can’t resist arching her back and wiggling her ass seductively as she slurps loudly on purpose, licking her juices off the seat. She has always enjoyed her own taste and this is no exception. She is acutely aware of the close quarters show she is putting on for the Headmaster as her bare ass cheeks are revealed to his scrutiny by the wisp of a skirt riding right up. He and she are separated only by the width of the desk. He can also clearly see the wetness dripping down her inner thighs. She wonders if he is leaning forward, and she is on tetherhooks as to whether he will touch her. He only watches for now, adding to Brenna’s growing erotic frustration.

“Beautiful. Good girl. Turn back around, undo the buttons of your shirt halfway, to just below your chest, hands on the desk, lean forward, legs apart.” he commands and Brenna follows. As she leans on the massive desk, her breasts spill free and are squished under her and against the wood, nipples peeking out, and her ass sticks out invitingly, with skirt riding up.

The Headmaster rises from his chair and walks around the desk to examine Brenna’s displayed behind. She is dressed just like he wanted her, and Professor Alcock feels the familiar and delectable twinging begin in his trousers. Watching her wet, bare treasures lewdly exposed while she obediently cleaned her pussy juices off the chair just now, started the inflating of his erection. He notes that Brenna followed the dressing instructions well and actually added her own touches, confirming that she is quite into this role play.

He is silent for a long while, which serves to stoke Brenna’s anticipation, her heart rate rising. His dextrous hands finally slip under the kilt and roam over her naked bottom. She startles at the initial contact but soon relaxes. The skirt has ridden up most of the way with her positioning, but he flips it up further, revealing the fullness of her pale peach globes, framed by the garter belt and lace thigh high black stockings. He cups her cheeks as if assessing their weight, then traces strange patterns with his nails and fingertips just grazing her exposed skin. He introduces some soft strokes, gently smoothing her ass, and for contrast adds in some more forceful kneading. His warm hands feel good on her otherwise chilly exposed skin in the air conditioned room. Brenna moans as he continues his ministrations.

“Eric has gone soft it seems. I see no marks on your snow white cheeks from this morning’s warm up. We’ll soon have to remedy that. I know your limit is light punishment, but this is decidedly too little. There should still be some colouring at least. Perhaps he was so taken with your natural ability, climbing heights of arousal when disciplined, that he focused entirely on pleasuring you, losing the much needed balance of attending to your correction thoroughly and well. He does get excited with specimens such as yourself. Its a good thing you are here now, where you can reap the benefits of more…authoritative discipline.”

“Mmmm…yes Headmaster,” she moans plaintively, “…I have much looked forward to this moment, to be properly disciplined by someone at your level. It is no doubt what I need,”

He continues massaging her bottom as one hand moves to barely graze the sensitive and very sticky flesh around her outer labiae and slit. He draws a finger down the pink bits, his touch as light as a butterfly.

The first smack on her ass is hard and loud, a sudden contrast to the butterfly touches, and Brenna gasps and squirms. Not paying her reaction much heed, Professor Alcock continues to spank both ass cheeks now with his palm, covering a lot of surface, in quick succession.

“Hold still. Is this what you need, Miss Swansea?”

Brenna’s bottom feels so warm and alive with the sting and muscle memory of impact. With each subsequent strike, these pleasant sensations transfer the igniting energy to her genitals. Her labiae are dripping with lubrication and she feels the tiny crackling, popping spasms beginning in her pussy.

“Aaah, oh! Yes, Sir, it seems this is exactly what I need…thank you…”

“Mmm yes, I’m glad we agree. That is very important.”

The Headmaster’s heated hands, now warmed up by the spanking, soothe and stroke gently over Brenna’s reddened flesh and these sensations directly feed her creamy secretions frothing down below. He delivers another fast series of firm spanks before continuing to speak:

“Mizz Swansea… cumming against instructions last night was not a transgression of omission or a weak slip-up, but rather, it seems, you disobeyed with full awareness and premeditation, is that correct?”

“Aahhh…Yes, Headmaster. I made the decision to do it despite remembering the instruction, and I also mistakingly believed it could go unproven and thus undiscovered.” Her voice is now tremulous and strident from all the cries and gasps she uttered during the spanking.

“You had intent to deceive…bad girl.”

“Yes, Sir. Although I did do it all in the heat of great lust and arousal as well, which made it very hard to resist for this horny girl.” Brenna says in her defence.

“Very well. Spoken like a true lawyer, great advocacy for both sides. In light of the facts presented, I do believe a bit more intensive punishment is due for the deliberate nature of your transgression, and also because… I am simply convinced you crave and need it, Mizz Swansea,”

Brenna feels his hands leave her bottom and next hears the sound of a belt being unbuckled.

Her body glows and is so on edge, her mind crackling with shock and excited anticipation. Does she really want this? A strap taken to her bottom?

“Do you know what is about to happen?”

“Yes Sir…I think so…”

“…Good. And how stands your disposition towards it?”

“…Mmmmm…Headmaster, teach me that lesson as you see fit.”

“Will you take the strap?”

“…Please Sir, yes, correct me with your belt…”

“You will take it. Good girl. Three, maybe four lashes on each cheek. It is just your first day here, so just for this part, I will give you another safe word to use. Red, as always, stops everything and sends you home, for six months. Yellow, on the other hand, you can use just for the rest of this punishment, and it means the lashing stops and we continue as usual.”

“Oh Sir, thank you, you are a most thoughtful and generous instructor. This girl truly appreciates it…and…I think you should definitely make it four on each cheek, to help the lesson really sink in…I think I’d like that…”

Brenna purrs, surprising herself again, and indeed, this extra safety net he has offered relaxes her and gives her more confidence to accept eagerly what is about to unfold. She feels safe and excited to experiment here to her fullest potential, and this is precisely what she was seeking when she started researching and considering visiting this place.

“Excellent. Eight lashes then, but, methinks we will spice things up and change the scenery a bit. I’m bored being stuck indoors. Cover your bottom with your kilt, and follow me outside, Miss Swansea.”

Dizzy with sensation, Brenna peels her squished chest off the massive desk and follows the Headmaster to a tall window, that happens to be a door onto a terrace. The thick, wool kilt feels scratchy against her spanked bottom and walking produces this uncomfortable yet delicious friction. Its warm and sunny outside and the blue sky is filled with white, whipped cream clouds. He directs her to hold the bars of the railing on the side, and lean forward as if looking out over the edge while spreading her legs and pushing her bottom up and towards him. They are on the third storey. She sees figures in the courtyard, near enough to see their faces if she concentrates, and she also notices that the building wraps around so that their immediate view is onto windows and terraces on the other side of the block. Again, just near enough to make out people’s faces. His hands are suddenly on her breasts, tweaking the nipples and exposing them to the sunlight and outside air through her unbuttoned shirt.

“I have a taste for doing this Al Fresco today, Miss Swansea. I so enjoy taking advantage of the fair weather, when we are lucky enough to get it.”

Brenna jumps when the strap makes first contact with her bottom. It isn’t intense pain but a good sting and a sudden sensation of impact. The swishing sound the belt makes in the air before it strikes adds to the experience. She moans loudly and wonders if anyone on the ground or across in the windows and terraces facing them can hear and see her. Someone is bound to be watching…

He is still going a bit easy on her, instead of folding and doubling, or tripling up the belt, he wrapped most of it in a coil around his hand and is lashing her with the single, free end. Brenna is shocked to admit she is enjoying this much more than she even anticipated. She moans loudly as he takes a break, and she pushes her needy bottom very lewdly towards him, yet again, surprising even herself:

“Ooooh…ahhhhh…More, Sir. Please, again!”

Headmaster Alcock obliges and works himself up so that the sizeable bulge in his tailored pants is now very uncomfortable. Brenna calls out after each stroke, even after the eighth, moaning, thanking and asking for more.

He’s caught up in the moment and her irresistible requests, and she gets ten lashes before he remembers himself and pauses. She is gasping and whimpering, but also moaning, her voice practically dripping with lust. She still appears to be in the throes of pleasure and asks for more. The word “yellow” doesn’t even occur to Brenna and the only urges she has are to continue this strange bliss.

She hears the belt drop to the tiled floor then, the buckle making a clinking thud. A small part of her regrets it’s already over. The Headmaster touches the dark pink rectangular tongue marks now peppering Brenna’s pink bottom, causing her to wince and gasp. Without warning, he pulls a finger upwards from the bottom of her soaking slit and pushes inside on his way up. The finger sinks effortlessly into her warm, slick wetness, almost pulled in by the velvety, slippery surface. His touch inside her fiery passage is exactly what she is craving after being deliciously warmed up by the vigorous lashing. Brenna arches her back like a cat in heat and pushes into the exploring finger.

“Ohhhh…mmmnghh…touch me Headmaster, please fill me more, deeper, I’m sssooo very wet right now…so ready for youuuu…”

Indeed, he has never seen something like this – not only are her folds suffused with copius amounts of moisture, there are now sticky trails dripping down the insides of her thighs, and as the moisture has collected in her inner folds, it actually drips, pulled down by gravity, from the point of her pink engorged inner labiae onto the ground, creating a growing, glistening puddle on the tiled terrace floor.

“I see what Eric found so irresistible…you are an exceptional student, Mizz Swansea, so much raw talent,”

“…and you are a great teacher, Headmaster Alcock, who makes it easy for a student to truly blossom under your…authoritative tutelage…”

He groans and like a man possessed, thrusts two, no, now three of his dextrous fingers into her center. Brenna is on cloud nine. Her consciousness has contracted to the nerve endings in her hot sheath and her burning bottom, and she feels his thrusts with her whole being and pushes wildly into each one.

“You took the strap very well, Miss Swansea. Good girl. Clearly a very high achiever. You should be proud of yourself. I believe a reward may be in order. Tell me Miss, what is your next…learning need?”

“Thank you, Sir! Mmmhmmm… ohhhh….ahhhh… my next learning need is to be…filled and fucked, pleaaaase!”

She hears the rustle of clothing being discarded and him putting on a condom, and then his hands are on her nipples, his half clothed body is pressing against her back, and the tip of his throbbing cock is at her needy entrance. Brenna smiles a most relaxed and luxurious smile. This game they’re playing is so hot. She unbuttons the rest of her shirt wanting to feel his body against her bare back. Without words, he understands and obliges, pulling the shirt down her arms and letting it fall crumpled on the floor. She grips the railing as if her life depended on it and is glad of it as his first thrust is sudden and deep and almost makes her lose her balance.

“Ohhhhhhhh yes, yes, yesss! Headmaster, more!” Brenna’s sounds of pleasure are somewhere between moans and squeals now. His loins slap against her hot, stinging bottom every time he gives her the pleasure of massaging and streching her inner walls with his sizeable rod on his way into her tight, silky passage.

“It is often said in the field of education, that the most important thing is the fit between a student’s learning style, and the method of instruction. Tell me, Miss Swansea, what do you think…about that fit,” he pauses to thrust again into Brenna’s creamy pussy with a grunt, and she moans as he continues:

“…About that fit for you,” he thrusts again, and adds through gritted teeth: “…right now,” Another thrust.

“Ohhhhh, Headmaster,” Brenna moans plaintively, “Mmmnghh…I think…the fit….is just perfect. Perhaps we can test it out some more, just to be completely full of conviction…?”

His loud laughter fills the air.

“Incorrigible girl.”

He fucks her hard and passionately from behind and begins kissing her neck on the in-thrusts. She moans and turning her head finds his mouth the next time he’s right up against her, and so he stays burried in her for a while and they kiss, ravenously and breathlessly. It all just got a notch more erotic for Brenna, if that’s even possible. His glasses are smeared with sweat now and partly fogged up, but they remain on his face, playing into his academic look and making him look incredibly sexy but also presenting an awkward impediment during the kissing. The subtle roughness of his jaw line with stubble just emerging, rubs against her soft, flushed face.

“Ohhhh…Sir…per…permission to spea…”

“Granted.” he grunts hoarsely, and doesn’t stop, oh no he doesn’t, but slows his pace a little to help her catch her breath and speak.

“Mmmmhhmm….mnnghh…ahhhhh! Oh Sir…I’ve been reflecting…like you said… you are right it would be such a shame for my limits to interfere with opportunity to experiment while I’m still here, so I’m thinking I’d like to explore just a little…. Ahhh, ahhhh, mmmnghh…. Have just a little action for my arse, please…? Not the full thing…we can just begin exploring to see, and then its a start isn’t it Sir, for a new learning experience…Ohhh…Ahhhh!”

A part of Brenna deep in her mind cannot recognize herself. Its as if the belt lashing minutes ago broke through some wall or shell within her, breaching any uptightness still left there. It seems that in addition to feeling amazing and dialing up her already peaking arousal, the strapping completely freed her, unleashing her courage and minimizing any remaining embarrassment, self-consciousness, fear or modesty holding her back. What was it Master Gregory said when she arrived? ….Maybe even discipline the longstanding mask, or pretence of being a good, modest girl out of you…. God, that man might just be a prophet in addition to instructor, as it seems he foretold what was now unfolding.

“Stellar student, Miss Swansea! Marvellous. So very proud of you for making the most of your learning opportunities! I propose we use the same scheme as for the lashing. Because this is very new, and you have some reluctance, you may use the word “yellow” to stop just the anal play part of this experience, without any other consequences.”

“Yes Sir, I like that very much, thank you.”

He reaches to where they are joined and his fingers sample a handful of the ample wetness Brenna is producing. The next time he pulls out, he pauses with about a quarter of his length still inside, to allow for some space to manouver. She protests the sudden stoppage of stimulation with a pleading moan. His wet hand feels her tight rosebud and spreads the lubrication all over it. The tip of his very wet finger gently massages and prods, finally just slipping inside. Brenna’s arousal skyrocketing, she is surprised with how much she likes this strange, new feeling. It feels illicit, and pleasurable, there’s absolutely nothing negative about it yet…

Headmaster Alcock gently massages and stretches the tight little opening for a minute or so, while his cock resumes shallowly thrusting just halfway into her pussy, resulting in Brenna squirming and moaning loudly. He then removes his hand and resumes full thrusts into her wet, silky slit.

“You liked that, little Miss, didn’t you? See, what was there to be afraid of?”

“Mmmmhmmm Headmaster it felt amazing. Thank you, I would like more pleease!”

Brenna writhes against the railing and moans and squeals unabashedly now, not caring who can hear or see them, or maybe even secretly wanting to be seen. Looking down she sees a few instructors gathered in a small group, looking up, one pointing in their direction. She sees some of the men have…their hands down their trousers, and one shirtless instructor has pulled out his erect cock and is stroking rapidly while observing them. Oh God, several men are watching, and more… She briefly imagines looking through their eyes and seeing the two figures locked in their vigorous thrusting rhythm on the balcony, him fucking her hard from behind, her breasts lewdly exposed by the wicked little corset shelf bra, bouncing up and down above the railing, their heady vocalizations not quite out of ear shot, like a porn soundtrack booming outside.

“Headmaster….!” She wails.

“Yes, Miss Swansea?” He grunts.

“Ahhhhhhh…I…I am SO close. I need to cum, please Sir, You feel

so so good fucking me like this…Sir pleeeeease!” She begs urgently.

“Mmmhmm…looks like we’ll do this together, my girl. Cum for me, prized pupil, now!”

His voice presses the only button in Brenna’s world right now and the dam breaks, immense pleasure surging through her. She trembles and pushes back into him for stability, her dripping slit pulsing around his now twitching cock. Time stops and moments are measured only by the rhythmic clenching and spurting. Brenna screams, her lustful, loud moans pierce the air. Their genitals joined and spasming together, it is a most exquisite feeling of joint surrender to euphoria.

“Fuuuuuuuck yes! Delicious, Miss Swansea…milk my shaft, that’s it girl! Mmmnghh…Ahh…ahhhh!!!!!!!”

They jerk together for a while, the remnants of their ecstasy slowly subsiding. The Headmaster pulls out, wraps his arm around Brenna’s waist and pulls her away from the railing. He spins her around and kisses her, her still erect nipples crushing into the rough fabric of his tweed vest and cotton dress shirt, he has lost the jacket somewhere along the way. He takes her hand and leads her, still on very unsteady legs, inside. He brings her to a black leather chaise lounge and passes her a water bottle.

“Rest a moment, sweet girl. Catch your breath before we continue. I’m going to clean up a bit.” He gives her marked butt a light playful smack as she lies on her side, stretching out and letting the cool air in the room soothe her bottom. He walks away to clean himself up. Brenna hears the door shut behind him.

She rests alone for some time, feeling relaxed and glowing from her massive orgasm. God, how is she able to have these mindblowing climaxes, each seemingly topping the last? Soon, she absentmindedly finds that her hands have made their way to her nipples and her clit again and she is rubbing herself. Half asleep and half turned on, she startles hearing the door open. The Headmaster must be returning. Before she can get her eyes fully open and herself upright, she sees an imposing figure behind the chaise lounge, and feels large warm hands on her breasts as he leans down. She notices that this can’t be the Headmaster, as the hands on her breasts are decidedly dark.

Master Craig smiles devilishly and leans down to kiss her so provocatively with his succulent lips, that she moans in response. His tongue fucks her mouth unabashedly in this very forward initial greeting. He looks like a GQ model, wearing a dark grey three piece suit, a different look than her prior experience with him when he was bare chested and his lower half was briefly and just barely contained in those tight leather pants…

“Just fucked and already touching yourself, 73. It’s fortunate I’ve arrived to continue the instruction you desperately require…”

“Mmmm!!! Mm…Master Craig!” she purrs into the kiss.

“Come, Miss Swansea.” He grabs her hand as she stands and leads her to the Headmaster’s desk again. He tarries behind her for a while, taking in her marked bottom and states his approval:

“The Headmaster disciplined you well and fittingly,”

“Yes, Sir, it was just what I needed,” she says hoarsely.

Standing next to the desk, he roughly kisses her again. He smells like…decadent coconut with background notes of citrus and rum. The visual is definitely dark and stormy, but the aroma is a luscious, boozy pina colada. Brenna loves what the bar is serving up tonight. She reaches for his face and he allows it and soon they are locked in a steamy makeout session and more, as he works her breasts and nipples and she reaches for the zipper of his trousers. He allows it all and Brenna is thrilled to feverishly unveil his cock, as it springs erect from the confines of his pants. His trousers fall around his ankles and he steps out of them.

“For the love of God, Sir, you are massive…”

Brenna can’t help herself and he responds with laughter.

“So I keep getting told. But you, Miss Swansea, saw it as no impediment. If I recall correctly, you took it all just last evening when we first met, without problems and with utmost delight. Will you refresh my memory?”

She hears the door open again, and this time it is the Headmaster returning. He feigns surprise at the two of them standing by his desk:

“I see that instead of resting, Mizz Swansea, you have magically regained your energy and are busy again becoming reacquainted with my good friend and esteemed colleague, Master Craig Roddick, Deputy Headmaster of The Academy.”

“Deputy Headmaster! Oh Sir, It’s my honour to be in your presence…”

“Craig, what learning path do you think suits this eager pupil next?” He cocks an eyebrow from behind his glasses at the handsome Black man.

“I was thinking, Mark, that we ought to test out her prowess for…equestrian skill next. In short, I’ll have her ride me. What say you, Miss Swansea?”

“Oh Master Craig, I’d love to…thank you…” She licks her lips seductively as the excitement at the prospect of riding his very large cock mixes with some anxiety about her ability to take it.

Headmaster Alcock claps and exclaims:

“A splendid idea! All ageeed then. But before we start, I’ve brought some…extra equipment for our student to take on her ride. Do you like the idea of having this along for your journey, Miss Swansea?”

He opens his palm, producing a slender, elongated, stainless steel butt plug. The outside of its thick base is crowned with a large sparkling sapphire crystal, in the shape of a heart. Brenna gasps:

“Oh Sir, how…beautiful…I can’t…I can’t wait to have you try it in me…though I’m not entirely sure that it will even fit…”

“Excellent. Don’t fret Miss, fit it shall, and you will do just fine. It’s one of the beginner sizes and a great way to delve into your newer area of study that you expressed such newfound interest in exploring. Spread, Miss Swansea, here on the rug just by our feet, please.” Headmaster Alcock orders.

Brenna lowers herself to the ground and panting, assumes the position.

She feels the Headmaster kneeling beside her now, and the squishy sound of lube being used. Her hands pull apart her ass cheeks, providing him with very easy access. Master Craig has also knelt beside them and is gently stroking his warm hands all over her body, her back, shoulders, bottom, any part he can reach as she lies in this coiled position. He even snakes his hands under her folded body to grope and tease her breasts. He removes her kilt, half undone by now and hanging messily half open across her hips, and throws it to the side.

Headmaster Alcock begins working the well lubed plug into her tight ass. He is teasing, gentle but firm with the rotation and pressure he is applying. He advises:

“Remember the word, Miss Swansea, if you need to stop.”

“I know Sir, thank you…don’t stop, pleeease…”

She feels someone’s fingers reach below, massage her clit and start thrusting two fingers in and out of her folds. She thinks she can tell this is Master Craig’s large, dark hand, by the sheer girth and his movement. The attention given to her sex stokes her arousal and she gasps as the plug now makes its way in, settling in her rectum. It feels…indescribable.

The cool, smooth metal fills and stretches her subtly in ways she has never imagined possible, and somehow, this feeling from her narrow, tight passage, creeps down and forward into her sex, making it quiver and swell. Her body grips the new invader tightly, as tender flesh envelops the hard, unyielding metal. The pressures of fingers in her sheath and the plug in her butt overlay and intensify one another. All the while, her bottom is still enflamed and the belt prints are only starting to pale a little. On a mental level, Brenna is absolutely intoxicated by her long time fantasy of having two men touching her intimately at the same time, materializing vividly in this very moment. She cannot believe this is finally happening, and how the reality of the ménage à trois surpasses even her wildest expectations for how hot it would feel.

“Oooooohhh, Masters….!” She groans, relishing using the plural.

“Good girl. Time to giddyup!” Master Craig intones and both men rise, helping Brenna to her feet. Moving with the butt plug in is a whole new experience.

The Deputy Headmaster spreads himself in the throne-like chair, legs apart and massive, black cock standing upright like a flag pole. He puts on what must be an XXL condom, and the sheath still doesn’t quite reach all the way down to his base…Both men gently assist her to manouver over the upright rod, aligning her entrance with the tip. Brenna faces Master Craig and as his large hands grip her hips, together, they help lower her so that the tip of his cock pushes into her wet slit.

Trepidation giving way to desire, Brenna settles in on his shaft and in one slow languid motion, admits all of him inside. God! She feels like a hand puppet filled and animated by her Master. She breathes raggedly, adjusting to this extremely full and amazing feeling she has never felt before. Between his giant cock and the butt plug, she is so full it feels like she might burst. She is also dangerously close to cumming again, but knows its too soon as she wants to savour and enjoy her ride.

The men read her expertly and recognizing she is overwhelmed with sensation, they encourage her to slow down and breathe and take the time to get used to the new, intense feelings. She is grateful and follows their lead. She leans forward and wraps her arms around Master Craig’s dark neck, clinging to him in a tender hug. His hard chest is pressing on her heavy breasts as she continues to embrace him. He reciprocates by stroking his warm hands down her sides and back and murmuring:

“Such a good girl. Mmmmm…breathe, girl. Slow down. Get used to the pleasure. It’s a lot, but you can take it.”

For a moment, Brenna is afraid she broke, so strong is the onslaught of exquisite but overwhelmingly new sensation. With breathing, some time and gentle encourageent from both men, she finally feels like herself again, horny as hell and drunk on sensation, but herself again.

“I…I think I’m ready, Gentlemen. This girl is grateful for you both waiting for her. May…may I ride now, Masters?”

Master Craig smiles, gives her bottom a light smack, and encourages:

“Giddyup, Miss!”

She starts bouncing on his giant cock, first shallowly, then harder, as she picks up the pace he helps her by grabbing her hips and literally fucking his own cock with her body, moving her up and down. Intermittently, she feels Master Craig’s thick lips sucking on her nipples and shudders with excitement. Brenna is panting and moaning loudly, and then, she feels Headmaster Alcock spread her ass cheeks as she rides, take hold of the jewelled base and begin to very slowly fuck her ass with the butt plug, moving it in and out in a complimentary rhythm to her impaling herself on Master Craig’s monster rod. Brenna, having taken in the cock and the toy, also takes in the heady realization that two men are simultaneously expertly attending to coaxing pleasure out of two of her openings at the moment. Having two sets of minds, hands, mouths and cocks at the ready to pleasure and challenge her, and being put in a position to serve both their needs is decadently arousing. This is how sex is truly meant to feel, Brenna thinks, and wishes that going forward she could always be enveloped by this doubled pleasure.

“Ooohhh… mhhmmmm…Masters, is this…am I getting… DP?” she asks wide eyed and breathless amidst the two pronged, steady movements.

“Yes, Miss Swansea. The light version, I’d say, but an excellent start for now. Full DP would involve a cock where the toy is right now, but there’s some learning and practice involved in getting ready for that. You are making incredible learning gains as we speak…”

Titillated by his response, Brenna moans louder and her hips buck and move up, down, and behind, in a confused frenzy of movement as she strives to meet and deepen both types of penetration taking place. Although the beginner plug is slender, combined with the girth of Master Craig’s oversized rod, it fills her so completely and makes each thrust so tight and acutely felt. There is this delicious, forbidden friction across a membrane separating her two inner passages, and she can feel the shaft and the toy stroking past each other.

“How is our student doing?” The Headmaster inquires with care.

“Oh, excellent Sir…mmmhmmm…ahhhhh….”

Brenna feels like she has died and gone to Heaven. She squeals as she rides Master Craig’s cock and the crest of her own pleasure, so close to orgasming so big, she is almost aftraid to go for it.

“Ooooohhhh…ohhh…ohhh!!! Fuck me, fuck me more please, here and there! I’m soooo full and it feels sooo tight! Mmmnghh! I need to cum…Headmasters! Please give permission for this naughty girl to orgasm!”

“Not yet. Ride a little longer, Miss Swansea. Let the Master come first, like a good girl.” The Headmaster’s deep voice instructs.

“Ohhh Sir, pleeeasee…Ohhhh….!”

She does her utmost best to ride while holding off the crashing of the wave, and now feels Master Craig twitch inside her, while Headmaster Alcock continues to steadily thrust into her ass with the butt plug, adding in some gentle rotation as well, coaxing more and more pleasure out of her pelvis.

“Ohhhh, Seventy Threeeee! You hot, horny cowgirl, so tight to fuck! Ohhhh…I’m cumming in your tight pussy, and Mark is fucking your ass with a toy and even I can feel it! You’re loving every bit of it and so am I! Aaaanghhh!” His massive rod jerks inside her as he digs his fingers into her hips, holding her down tight.

“You may release now, Miss Swansea.” The Headmaster commands in her ear from behind, and Brenna thrashes wildly in the biggest orgasm of her life. Pussy and ass full and lasciviously overstimulated, she cums and cums in a series of repeated shudders and isn’t sure what is happening anymore. Her body crackles with electricity and her consciousness temporarily splinters as she deliciously falls apart with her orgasm taking over. Both men hold her and their support helps to contain the shattering pieces enough to put her back together. She feels wonderfully safe and so well taken care of, with two sets of strong arms supporting and holding her throughout the wild climax.

She comes to, feeling satisfied, sore and exhausted and finds herself sitting on the chaise lounge, supported on either side by the two men who just gave her Heaven. She notices the butt plug is gone and finds herself disapointed, missing the sensation. She sits in the Headmaster’s lap but leans against Master Craig’s strong arms. He is now naked, his chocolate body delicious to behold, while the Headmaster still wears only a very poorly buttoned up and crumpled dress shirt and of course, his glasses, now slightly askew on his face. Brenna has lost the shelf bra, but somehow retained the lower part of her lewd lingere throughout the encounter.

“Happy Birthday, Miss Swansea.” both men say together and smile mischievously, while the Headmaster cradles and cuddles her sensitive, warm body resting in his lap.

“Thank you, Headmasters…This has been the absolute best birthday ever,” she says breathlessly. She thinks to herself that she has just feasted on vanilla and chocolate cake to mark her special day, and it’s been even more rewarding than the most delectable of desserts. She kisses Headmaster Alcock tenderly and reaches a hand down his partially unbuttoned shirt to run her fingers across the hard muscle and the coarse chest hair. As he eventually breaks the kiss, she turns her head to find Master Craig’s full lips already seeking hers. Their tongues dueling, the kiss is warm and erotic, her hands now roaming over his neck and muscular shoulders. She can’t get over how hot it is to be kissing one man while pressing into another’s body for support and feeling this other man’s hands play again with her erogenous zones. The Headmaster’s one hand has found its way to her right nipple, to roll and pinch, while the other is gently massaging her clit. While Brenna’s and Master Craig’s lips remain locked in deep kisses, the Headmaster’s tongue and lips caress her neck and shoulders. This multitude of sensations and the double attention lavished on her is priceless.

She turns again to the man whose lap she sits in, and whose growing erection is becoming hard to ignore as it presses against her bottom and wet folds.

“Headmaster, this is sooooo, soooo good…but I worry it’s…been a while since you’ve been properly satisfied yourself…please let this grateful student thank her Headmaster and take him in her pussy again or her mouth…Mmmhmm…”

“Mmhhm…good girl, looking after her instructors…knowing her place, wanting to please…” he praises her, kissing and sucking in her skin harder down her neck.

Master Craig slowly gets up and starts searching for his clothes, but Brenna turns to him, grabs his hand and giving him a pleading look begs:

“Master Craig, stay as well, please. I love having you both with me. This girl will pleasure you too again, maybe we can figure out how to do it all at once…The Headmaster perhaps now in my pussy and you, Deputy Headmaster, in my mouth as I get on all fours…? I would very much like to try that…Mhhmmm…”

Master Craig laughs deeply and warmly.

“My amazing girl. Now that is a project proposal I could get behind, or rather in front of! You know what I mean. It sounds extremely agreeable, but we’ll have to take a rain check I’m afraid, its almost discernment time!”

“Awwww…noooo…but its my last evening here! And, what happened to the second afternoon class, I’ve missed it?” Brenna exclaims anxiously.

“You attended an…extended Individual Instruction that was signed off on by the Headmaster and his Deputy, Miss. Highest level of approval issued.” Headmaster Alcock reassures her with a wink and a smile.

“…and that’s a pity, Miss Swansea that you are leaving tonight…or maybe, you aren’t? Discernment time will tell I suppose…Besides, I am regrettably fully booked for tomorrow, although…the night is young and I wouldn’t mind burning some midnight oil to accommodate this excellent project proposal you just outlined, Seventy Three. Mark, would you be available?”

Continuing to kiss Brenna’s neck, and not yet showing any signs of letting up on massaging her clit and gently rolling her nipples, the Headmaster replies:

“Absolutely, Craig. Happy to support an eager student in her advanced project by flexing my time. And because we’re Headmasters, we can! What will it be, I wonder, Miss Swansea? Home as planned or an…extended educational stay? Think hard,”

Brenna momentarily loses track of what exactly he is saying as he emphasizes the word hard, and pairs it with giving her clit a particularly solid pinch while inserting and slowly pumping his middle finger into her swollen, wet slit. All this twinning in Brenna’s awareness with the now urgent feel of his hard erection against her tender bottom. She moans with pleasure, and newly stoked need.

The Headmaster continues:

“We will reconvene after discernment if you choose to stay. Otherwise, we will certainly call in the rain check on your next visit…Don’t forget your new watch, Miss Swansea, so that we can…stay in touch…”

* * * * *

Thank you for reading! Please leave a comment and / or vote if you enjoyed the writings.

What will be next for Brenna? Wait patiently and you might find out!