Brenna at the Academy

This is Chapter 4 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. I hope you enjoy the stories!

*****

Master Craig is now half dressed and frantically checking and re-checking his wristwatch, as he walks around the Headmaster's office trying to locate his shirt. Brenna still sits in the Headmaster's lap and is now squirming wildly. Her breaths come fast and ragged, tears well up in her eyes and she mewls desperately:

"Headmasters... please... please... please let me... please... May I suck Headmaster's cock, pleaaaaaaaase!"

She wails and starts sobbing. Brenna isn't sure what has come over her, but she is suddenly tearful like a petulant toddler and hot tears roll down her face. There's an ache inside her and she is simply overwhelmed by a sudden need to serve and thank her Trainers, and particularly the Headmaster, who hasn't had a turn being pleasured by her most recently.

Master Craig circles back as he is buttoning up his shirt.

"Uh-oh, Mark... I think we broke her now..." He eyes Brenna with concern.

"She's riding an endorphin and oxytocin high. The last twenty four hours have been a lot for our new student..." The Headmaster assesses as he cuddles Brenna, rubbing her back and stroking down her arms.

"Pleaaaaaaaaaaase Sir, I beg you, let me taste your cock. Pleeeeeeeeeeeease let me thank you... I can't leave you hard like this and unattended... you've been ssssoooo good to meeeee..."

The Deputy Headmaster bends down to whisper in his colleague's ear:

"Mark, I know it's hard to give in when its

your

cock she's begging to suck, but I'm backing you up. I think we should let her. We need to reward her sweetly grateful, submissive impulse, not reject it right now..."

He pats the Headmaster on the shoulder.

"It's a formative moment, a teachable moment in her learning,"

"I hear you... but it's just about half an hour to Discernment... There's no time... and she... she's sex-addled right now, we should wrap it up and give her a rest, help her cool off..."

"I'll get things started at Discernment. You take your time and enjoy. Seventy Three is a talented oral giver, she won that challenge and sucked off Greg within six minutes or so!"

Master Craig winks at the Headmaster and bends toward his ear again to add in a whisper:

"...and yes, she's addled, but you know that's when they're the most

pliant.

Reward her submission and let her suck you, Headmaster, that's my vote."

After a moment of consideration, Headmaster Alcock gives in and announces:

"Oh very well. Miss Swansea, on your knees, between my legs. Time to show your gratitude!"

"Oh thank you, thank you Sir! You will not regret this!" Brenna wipes at her tears and slips off the Headmaster's lap to kneel between his legs.

"Stop. Craig, can you help us out with one last thing before heading out?"

"Already on it,"

Master Craig is already kneeling behind Brenna and holding something as he rubs a hand down her spine and lustily instructs:

"Sweet thing, Spread for me."

His voice is like deep, dark honey. Brenna obeys without a moment's hesitation, and the next thing she feels is the lubed up butt plug pressing against her anus, while Master Craig rubs her clit.

"Awww..ahhhh... mnngh... Ahhh!" Brenna whimpers and moans.

"Butt plug in for any and all sexual activities now, Miss Swansea. It's part of the training you've embarked on,"

"Yes, Headmaster... Mmmmhmm...ahh!"

Her whimpers are higher pitched now. Master Craig's thick finger probes and touches softly just at the wet, sticky entrance to her pussy. He toys with the opening while using his broad thumb to push against and circle her clit. Brenna's need is quickly building towards another release. Before she climbs the height of her arousal, however, her sphincter relaxes and the plug jolts into her bottom, filling her with other delicious sensations just as she laments the loss of stimulation, since Master Craig pulls out and walks away instantly after achieving his goal of helping her insert the plug.

"...Since I've got to jet, though I

sincerely hate

to leave you both, I have something to at least approximate a bit of ass plug fucking for you, Seventy Three," Master Craig quips, and Brenna jolts as he snaps something around the base of the plug.

He pushes a small remote into the Headmaster's hand before waving and leaving the room. The Headmaster pockets the device and sets it off.

"Ohhh! Aww... Mhmhmmm... ooohhh!" Brenna moans, unable to help herself.

Master Craig snapped a vibrating cock ring around the base of the plug and the Headmaster has turned it on, jiggling the plug and spreading delicious vibration to Brenna's tight back passage, so tightly and desperately wrapped around the stainless steel intruder. With shaking hands, Brenna reaches for and grips the Headmaster's hard, straight erection pointing at her face. She stares up at him, her gaze drunk, glazed over and very sexual. Brenna licks the tip of the Headmaster's cock before engulfing the head with her lips, like a lollipop. She works his silky, warm length with her small hand and uses the other to weigh and massage his testicles. The Headmaster purses his lips in a tight, thin line, throws his head back and releases a masculine moan.

Making a seal around the head of his cock, Brenna sucks eagerly and at the same time flutters her tongue over the tip, tasting the salty drops of his pre-cum. She laps it up like the best delicacy and feels the strong, salty taste fueling her arousal. She teases the underside of his shaft just at the junction of the head by digging her soft little tongue in that spot repeatedly. Finally, Brenna moves her lips further down his warm shaft, and begins bobbing her head up and down, still applying eager suction.

"Good girl." The Headmaster grunts and tangles his fingers in her hair, helping along with her movements.

"Such a fucking good girl for me, taking my cock nice and deep and sucking like a pro,"

Encouraged by the filthy praise, Brenna works the Headmaster's lengthy shaft in and out of her mouth with great enthusiasm while she squeals softly. He adjust the intensity on the remote control and Brenna grunts out a deep moan. The guttural vibration transfers to the Headmaster's cock and he responds with a lusty, animalistic groan. It's a devilish domino effect. He increases the intensity of the vibration over the base of the plug, she feels it acutely and her moans in turn stimulate his cock in her mouth with the vibrating kinetic energy. It's a wonder of mechanical science that travels from him, to her and back to him.

"Mmmm... Oh Sir..." Brenna moans in the breaks she takes from sliding her lips down the Headmaster's soft, warm shaft.

"What is it, Miss Swansea?"

"Ahhh... I need to come... I'm getting very close, Sir..."

"Look at me, Miss Swansea," He commands sternly, and Brenna opens her eyes and looks up dreamily at his face from below her lashes, while puckering her cheeks around his cock.

"Good girl. Looking so sexy like this...You don't

need

to come, you

want

to come. There is a difference."

Brenna nods slightly, continuing the blowjob and taking the Headmaster's cock almost to the hilt now on the in-thrusts. A small moan of disappointment escapes her lips. Her cheeks hurt a bit and her eyes are watering but she's undeterred and as lustful as ever.

"You want to come just from sucking my cock and feeling the plug vibrate in your tight little ass? You are a very, very horny girl. If you can come just like this, Miss Swansea, you may. No touching yourself though, and try to hold off, as it pleases me to see you focused on my pleasure at the moment."

"Yy...yes... Headmaster. I want so much to please you, and sucking you makes me so hot I can't help it, "

"Good girl. So fucking warm and wet. Taking such good care of my cock with your hot little mouth. Licking like the eager, excellent student that you are."

His words go straight to her pussy, coaxing more moisture and heat forward. Brenna notes how he commands her to hold off her release, but at the same time teases her mercilessly with both the buttons on the remote and the filthy praise leaving his disarmingly handsome lips. The delicious torture of mixed messages is a high art at this institution, and Brenna is held bound, aroused and captive by it all.

Brenna exerts all her oral sex skills to her best effort and does not lack enthusiasm in her performance. It is not long before the Headmaster closes his eyes as his face begins to tighten and contort with each thrust into Brenna's hot mouth, his desire cresting and his release building. Grabbing Brenna's head and holding her hair, the Headmaster fucks her mouth hard in the last few thrusts before his cock twitches and begins jerking and spurting hot cum far at the back of Brenna's eager little throat. Brenna still sucks and swallows eagerly. The Headmaster's one hand finds its way to her throat and while not restricting air flow, gently presses against the skin in front of her larynx, feeling the rhythmic swallowing movements of the muscles of her esophagus and throat. What he feels pleases him immensely as he stares at Brenna intently with fire in his eyes.

"Such a fucking good girl, sucked and swallowed every bit of my cum...Do you like the taste, Miss Swansea? You seem

very

hungry for it..."

"Yes Headmaster. You taste delicious... Thank you for letting me taste and milk your cock. I hope you felt my gratitude for all that you have given to me tonight. This student is very lucky."

He presses the remote in his pocket again and Brenna is brought over the edge, letting herself let go finally as she held off long enough to prioritize the Headmaster's pleasure as instructed. She squeezes her thighs together and bucks as she kneels, the buzzing on the metal entering her tight ring spreading into her pelvis and down to her sex, igniting a set of spasms and shudders. Her eyes roll back in her head and she moans.

"Ahhhhhhhhh...! Mnnnghh! Thank you for letting this girl come again, Sir. Thank you..."

"Good girl. You are breathtaking when you come, Miss Swansea. And now, I hate to rush us, but time is of the essence and we must both hasten to the Discernment hall. Catch your breath, drink some water, and up you go. It will be Goodnight for now, Miss Swansea, but before we part, Spread so that I may retrieve your rear passage's decorative filling,"

Brenna is still dizzy and buzzing from her climax but she obediently turns around and assumes the position and the Headmaster pulls the plug away from her ass in one gentle movement.

"Sir... must you take it away? Would it not be better if I train longer with it inside?" She asks sweetly.

"Miss Swansea, your eagerness is noted and appreciated, but Discernment is a time where students are to be free from any sensory triggers or distractions that may sway their decision unduly. I'm afraid it must be removed for now. Goodnight, Miss Swansea."

"Goodnight, Headmaster." Brenna replies with disappointment and craving in her voice.

*****

Discernment.

Having haphazardly dressed herself in the clothes that magically appeared in her room and having quickly brought some sort of semblance of propriety to her face and hair, Brenna rushes to the assembly hall downstairs for her first experience of Discernment. Her body barely having had time to thaw and settle back down from her climax, she is still blushing and warm and her legs feel slightly wobbly. Discernment is the function where students are meant to reflect on their Academy stay so far, and calmly,

without

any influence of lust and arousal and the associated stimuli they have just been bombarded with, come to a rational decision about whether they will heed their initially planned departure date, or make a change and re-commit to a longer stay at the Academy. For Brenna, it is a choice between driving home tonight, after the ceremony, or staying until tomorrow night and heading back to the Headmaster's office after Discernment for the promised second installment of her ménage a trois session. That choice also comes with a day full of surely delicious and debauched activities for Sunday, her final day tomorrow, unless of course she were to choose at tomorrow night's Discernment, to remain here even longer into the week.

The feeling of clothes against her skin and the glimpses she catches of the garments on her as she looks down her own body feel awkward and kind of uncomfortable. It seems like she is looking at another body, not her own. The discomfort of clothing against skin feels stark after just over 24 hours of almost uninterrupted nudity. Of course, her pussy and ass still feel the air and chill in the room as panties were not part of the required uniform even for arrival at the Academy.

Brenna enters the hall and sees a colonnade that separates the hall proper from the hallway. In it are rectangular metallic pods that function as gateways through the colonnade and into the Discernment hall. She quickly moves to one with an open door, and finds herself in a small medical office. The door shuts behind her and a small, dark haired woman sitting at the desk in dark blue scrubs, introduces herself:

"Hello, I'm nurse Mila." She smiles professionally.

"We attend each Discernment event to provide a quick medical check-in for all trainees. If anyone is deemed to need medical attention or not be fit for extending their stay, they must heed our recommendation and return home if asked to do so."

"Hi Mila. I'm Brenna."

"Hello. Is there anything, Brenna, that you think you need medical attention for? Are you feeling alright? Any significant pain?"

"Everything is good, nurse."

"Very well. We'll do the routine checks and if everything checks out, you'll be on your way into the Discernment hall."

Mila proceeds to attach a cuff to Brenna's arm and take her blood pressure. She nods, then moves close to her.

"I'm going to prick your finger just to get a quick blood sample for basic analysis," Mila proceeds with an efficient and well-practiced manner. She feeds the strip into an electronic reader.

"Looks good. Maybe a bit of dehydration only."

"Mouth..." Mila takes a close look at Brenna's mouth, motioning her to open up.

"All looks well. Please get up on the bed with feet up in the stirrups. Pull up or remove your skirt."

Brenna complies and the nurse gently prods with her gloved hands, assessing the genital area and the bottom.

"Some tenderness and a bit of chafing... which is expected. No broken skin. Everything's a bit swollen and engorged, but again, that is expected...sensors still in place... Any concerns about changes in discharge? Any bleeding? Is it close to the time when you expect your menses?"

"No, and no. All good, thank you."

"Very well, Brenna. I'll give you some moisturizing and gentle antibiotic cream to apply to your genital area before bed, after...your activities. It will help with the recovery and maintaining everything in best possible order. Are you eating well and hydrating?"

"I think so...?"

"Good. Based on the blood sample, I'd like you to drink more water... and remember to frequently go to pee. Preferably after each intensive...penetrative activity, whenever you have a break. The Instructors encourage this as well. It's meant to help prevent a UTI and keep everything in best working order."

"Yes, I understand. I will do that."

"You can stand up. Before you go, please bend over and show me your bottom, then, turn around and lift up your top or unbutton it so I can take a quick look at your front and the breasts."

Brenna follows the nurse's instructions. While examining her bottom, Mila informs:

"Some minimal redness and a few small welts, nicely receding. Nothing that looks like it would not be gone by a few hours' time".

"That tracks. Thank you, nurse. I'm glad we can get this check-up and your reassurance."

"Thank you Brenna, it's nice to meet you. There are no medical indications that would suggest that you must not continue with your stay at this time. Please enter the Discernment hall and good luck with your decision, which is entirely up to you."

Brenna thanks Mila and heads out the other end of the metallic pod. Opening the door, she enters an area similar to the check-in lobby she was in just on Friday night. Brenna can't believe that this is only her second day here. She feels like a different person and the world, the world feels like a different universe. In the medieval looking hall, sconces and chandeliers hang from the vaulted, high ceilings. The room is arranged like a gymnasium at exam time at a university. A podium stands in the front centre of the room and throughout the space, neat, lengthwise rows of chairs and desks fill the hall. Brenna sees that they all have large numbers displayed and quickly finds her student number and settles in at the desk. Soft, Zen, spa-like music infuses from speakers around the hall. On her desk are a number of papers and an iPad.

Brenna recalls the Headmaster's words, that discernment is a time of purity and calm when students are supposed to be unaffected by the events or sensory features of this place. Students are meant to be washed clean and dressed in the clothes they arrived in, which have been freshly laundered for them. Brenna feels out of place and uncomfortable, as if the nudity and freedom of being unencumbered by clothing for the last day was more natural to her now. As she did not have time to shower, given her extended session with the Headmaster, Brenna is constantly aware of smelling the two Headmasters' scents on herself. It is heady and dizzying. Master Craig's boozy, tropical aroma and the Headmaster's sharper, clean, sandalwood smell fill her nostrils with every whiff. She smells like a combination of her own scent, their scents and the smells of sweat and sex. She feels naughty and dirty noticing this, thinking she is supposed to be showered and clean, but alas, things took a different turn and a different priority was agreed upon that left her with very little time to put herself together for this event. Brenna smirks, thinking that even if the students are scrubbed clean and innocently perfumed, the fresh sensory memories carried by their bodies and minds must still affect them, so the whole pretense that Discernment is a return to purity and an objective choice uninfluenced by any of the ever present debauchery hanging in the sheer air of this place, is a bit comical and ironic.

Brenna picks up the iPad but is quickly distracted by hearing Master Craig's voice from the lectern at the front of the room. He looks impeccable, dressed again in his three piece suit that looks freshly pressed. Embodying the suave Deputy Headmaster role, he announces:

"Trainees, congratulations on completing your planned stays. I am Master Craig, the Deputy Headmaster of our Academy. It has been, a true

pleasure

to have you here and we commend you on choosing our educational facility for your explorations. We at the Academy hope that you have found our institution to be all that you have hoped for, and perhaps even more. Please take some time now to answer the surveys and questions provided and reflect on your stay and learning. Next, please review a possible preview of your extended stay, were you to choose to remain with us for tomorrow. Please note this is a tentative sample schedule only but gives you an idea of the electives and choices you may participate in. Please answer the set of questions that is meant to collect your preferences and wishes as to the unfolding of your education tomorrow. These will be taken into account in designing your learning plan.