Brittany

Still full of hesitation, I find myself lagging behind the crowd. By the time I gather the bin and toolkit, I turn to realize I'm the last one. Clutching the cushion they provided to my chest, I look around the room in rising panic. Where are my friends...? I can't do this alone...! No matter how many times I look back and forth, I can't find anyone who will lock eyes with me - someone to help me. This can't be happening... what will Delilah do to me if I can't do the lesson..?! My heart begins to pound in my chest as my legs lock up with fear. I feel a wetness start to well in my eyes. I'm standing in this room. Naked and caged. Alone. I'm not sure how much more humiliation I can take.

"Hey there, sweetie. What's the matter?" I realize at the sudden voice that I've been holding my breath. My perspective expands from the tunnel vision I had started to lock into. When I look to find it's source, I feel the dread start to creep back in. Brittany stands a few feet off to my side, having snuck up on me by staying close to the wall. She has her hands back on her hips as she looks at me with a grin, one eyebrow cocked with what I can only hope is concern. Unfortunately for me, her tits are closer to my eye level than her face, and so those are what my eyes drop to next. With a surge of embarrassment, I completely look away from her and back to the crowd of pairing off boys that now spread out across the padded room.

"Oh! N-nothing. I just uh... I don't think I have a partner..." I say, not realizing such a response is not at all enough for her to leave me alone. I look back towards her from the corner of my eye, searching for her reaction; hoping that all her friendliness wasn't just a façade to get us all to go along with her instructions. She turns her head to scan the room before looking back to me with the same nurturing expression.

"So it seems. You could still do it alone y'know... Though now that I look at you, I'm guessing that might be a little too big of an ask, huh?" At the question, all I am able to give is a nod.

"Hmmm... Alright, fine. Let miss Brittany take over for you." Her tone of voice drops an octave, shifting from peppy instructor to something a lot more intimate. Surprised by the offer, I look back to her face to find she has stepped much closer to me, practically nesting my head between her bouncing boobs. I lock up again as a chill runs through my spine, frightened that somehow I might offend her by being so close to her naked breasts, despite this whole situation being her doing.

"U-uhm... o-okay..." Is all I manage to push out through my pursed lips. My heart beating fast all over again, though now it's due to equal parts uncertainty and excitement.

"Good boy..." She says, her eyes half lidded with a subtly predatory expression, one I am not fully able to clock due to my racing mind. This beautiful woman is gonna... touch me... her tits are so big... I just want to touch her... I want us to... I realize my imagination is getting the better of me as Brit suddenly takes my hand and leads me to an open spot on the floor. Practically spinning me around, she takes a wide, confident stance as she points a finger dramatically down to the ground.

"Down, boy." She commands. I glance around with confusion at her choice of words - treating me like some sort of dog. Even still, I slowly follow suit, dropping my bin and cushion and sitting down on my knees.

"Good boy." She says after patiently waiting for me to get in position.

"Now... Show me your pussy." She says with an evil grin that seems foreign to her face. it takes me a moment to process what she means. She wants me to show her my ass... and she's calling it pussy...? Like I'm a girl or something...!? I feel a rush of shame and indignance at her choice of words, causing me to freeze in place as I look up at her.

"I said... Show me. Your. Pussy." She takes a step forward, now practically hovering over me. Unnerved by the personality change she seems to have undergone, I'm frightened of the possibility of punishment, so I slowly obey. I turn away, placing my cushion on the ground in front of me as I plant my face and arms atop it, presenting my ass for her.

"There, was that so hard?" She says, her voice shifting back to a more seductive - if still threatening - tone. I feel the shifting of the padded floor as Brit lowers herself to my level behind me.

"It's okay. You see, boys like you are basically like us girls. You just can't make babies. But that's okay, that makes you perfect for loving." She continues in her softer, more intimate voice as I feel a hand lightly circling one of my cheeks.

"That's why you're here. To learn. You learn your place. You learn to behave. You learn what you are. It just takes some time. And sometimes, a firm hand." I hear the wet sound of lube being rubbed in her other hand as she continues to circle and knead my ass. When she finishes talking, I feel a sharp sting on my ass cheek as the hand that was caressing me gives a sudden slap, causing me to yelp in surprise and pain.

"Shh, it's okay. It's just a love tap, baby. Sissies like you will get used to it. In time, it might even feel good." She says as the hot skin she slapped is then grabbed and pulled, causing my cheeks to spread and reveal my secret entrance. Before I can process this sudden change, I feel the cool slickness of her fingers as they begin to rub up and down along my crack. I feel a tickle in my brain every time her lubed fingers brush across my hole, certain she is applying extra pressure whenever she does. The speed of her hands causes me to mewl slightly at the sensation, every pressing pass sending the faintest of pleasure signals running from bottom to brain. Before I can get accustomed to her aggressive massage, she changes tactics. She takes her lubed fingers and presses them into the wrinkled flesh of my entrance without actually pushing inside. Instead, she pushes out towards my cheeks, pressing the triggers of sensation from my ass to my insides at the base of my trapped dick. I find myself starting to get frustrated by the endless teasing, as she continues to go back and forth between styles, never letting me adjust to the sensation. I also notice she never pulls her hands away from me, yet every time she digs her fingertips into my agitated ring they come away wetter than before. Is that my doing...? Am I leaking something...? I consider it might be the fluids doctor Andrea's medicine has caused me to produce, though I am intrigued at their presence now, of all times. All of a sudden, Brit stops, pulling her hands off me. The lack of the slick contact causes me to be disappointed, though I curse myself for admitting it.

"Alright boys, it's time to swap positions with your partner! Every sissy get's his chance." She calls to the rest of the room. For a moment I had forgotten she was the boss right now - in charge of directing whatever ludicrous 'lesson' she is putting me through. As I listen to the shuffling of skin against the padded floor, I feel Brit get very close to me. Resting one of her ample breasts against my back, I feel the smoothness of her wide areola brush against my skin, reminding me that it's an extremely attractive woman currently dominating my ass. I blush as her other hand reaches up my torso, brushing against a nipple before reaching my chin and pressing a finger inside my mouth.

"That's right, sissy. You don't get to use your pathetic dick. You have to use your ass like a pussy. But I promise you'll come to love it." She nearly whispers in a low voice that causes me to shudder. She pulls herself back behind me before I feel the rapid movements of her spreading my cheeks and pressing the finger I had just had in my mouth onto my hole. I squeeze my eyes shut, my mind still racing from the insults she threw at me while she pressed her half-naked body against mine. It was all too much. When her fingertip plunged inside me, I let out a noise of shock from deep in my chest. She had managed to push nearly her entire finger inside me before I had instinctively flexed around her. The combination of surprise and pleasurable tingling from her penetration makes my mind fill with pins and needles.

"There there, sissy. It's okay. I can make you feel good. Better than any feeling your little clitty could give you..." Brit whispers to me from behind, her voice filled with comfort, yet her choice of words only add to my growing shame. Oh no, is she right? I never got to have sex with a girl. Now one is fingering my ass... She's making fun of my dick... And she's right, I can't do anything with it now that it's all locked up... I'm thankful my face is already smushed into the ground, as it allows me to bury my head like an emasculated ostrich. Despite her teasing words, it doesn't take long for my ass to loosen around it's intruder, allowing Brit to start moving once more. My head buried in the ground, all I can experience is her movements inside me. Surprised, I find she is rather slow and gentle. She works her hand in small circles, continuing to stimulate my anal lips while slowly loosening my tight grip. After several long minutes, I find I have gotten used to the sensation, almost finding it relaxing. Only then does she start to press. She pushes her fingertip down in a reverse curling motion - applying pressure from my entrance all the way to the furthest reaches of her invading digit. Already I feel a warm pressure being built by her movements; a heat that pulses behind my dick with every brush that feels as if I'm going to pee myself here and now. I start breathing hard from the constant pleasure. It's nice, but confusing. And hot. So, so hot. My brain... I feel like I'm going foggy... Every so often, Brit changes the direction of her movements, brushing from the inside out instead, renewing the building pressure inside me. It never grows to a peak, but instead feels as if she is working around something. Avoiding the thing that will truly feel... good... After several more minutes of this pleasant - yet torturous - experience, Brit spontaneously retracts herself from my insides and stands behind me.

"Alright, good job everyone! Our lesson for today is nearly over, but I have some homework I need to give out before you leave us for the week." I stay on the ground as she addresses the class, still letting out small pants. As I begin to recover, I sit up on my haunches and realize what had just occurred. She played me like a fiddle...! This is the most... humiliating... Gah! I practically shout inside my own head, furious with my own inability to fight back. Brit was just too seductive for me to handle.

"So before you all go, I have one final present. It probably won't get you to cum, but that wasn't really our goal today anyways, what with how you're all still pure little virgins, and all. You are all required to wear this-" Brit speaks to the class, her big tits still jiggling with every slight movement. She then pulls a small metal bulb from a nearby box she gathered from the side of the room.

"This is a plug. While you're on campus, you are required to wear this at all times, unless using the toilet or a superior takes it out for you. Or of course, you're here with us." She gives a cheeky smile as she shows the plug to the room of freshly aroused boys. Audrey grabs the box and begins to hand the plugs out to each boy in the room as Brit continues.

"The size here is to help you all adjust to having something in your pussies, not really to feel good. That doesn't mean you can't try, mind you! And I hope I don't need to remind you, but if any superior finds you not wearing your plug without permission, you will be punished. So lube up, and pop these in. After that, you can all get back in your uniforms." As Brit finishes her announcement to the room, she hands the plug she's been holding as the example to me.

"This one is for you sweetie. Be a good boy and slide it in." She gives me a wink as she hands me the toy.

"W-wait, Brittany... I mean, Brit... Why were you so... I mean, I felt like you almost found..." I'm unable to form the sentence, wanting an explanation for her expert teasing, yet lacking any satisfying 'relief' she was so adamant about teaching us at the start of this whole lesson.

"Even an expert hand can't get a horse to drink his fill once he's led to water." She says, recycling a proverb about leading horses to water and really causing me to be confused. She must have seen my scrunched expression and giggles.

"You have to want to feel good for it to feel good, sweetie. That, and probably another trip to the doctor's or two." She smiles at me before walking towards the doors, opening them as the black-clad futas that act as our guards and escorts walk in. Realizing I'm still one of the few boys that has yet to finish dressing, I quickly throw on my uniform before joining the crowd. The walk back to the dorm was short and quiet, especially for me all on my lonesome. I can't help but think about Brit's words. The fact that I was so **** for satisfaction by the end of our lesson, yet apparently wasn't 'ready enough' causes me to wonder how invested I need to be. After all, this stupid cage is only tighter than before... I don't think I've stopped leaking since we left that room... The occasional jolt of electricity I feel from my new plug only amplifies my frustrations as go about my routine for the rest of the night. I can only hope whatever lies in store for me can help me understand what I'm supposed to do to find this mythical 'relief' Brit had promised.