Casey

I begin scanning the room of semi-familiar faces looking for help. Despite the obvious lead up to my current situation, I still find myself unable to act on my own; having to choose another... boy... to finger me. Even as I walk through the room with my bin and cushion I feel my legs begin to freeze, unable to find someone to help me. I'm all alone here! I don't talk to anyone... Why would anyone be brave enough to do this lewd thing with me...? Yet even as I stand in fear with my thoughts, I catch the jet black hair of Casey through the crowd. If anyone could be more embarrassed than me in this room, it would be him. He stands with his cushion held in his lap to hide his flat cage, his pale skin beet red as he stares straight at the floor. I feel my sense of empathy begin to overpower my own frozen legs as I make my way over to him.

"H-hey... Casey..." I stammer out. My sad excuse of a greeting is still enough to cause Casey to jump as his eyes shoot up to meet mine. His face shifts from an expression of pure shame to one of tentative relief, seeing it was me in front of him instead of one of the instructors or some other, more aggressive boy.

"Oh! Sam. Can you uh... can you work with me...? Please?" He raises his cushion from his waist to his chest, his shoulders hunched as he twists the fabric of the pillow between his hands. I can't help but think he's cute in his **** shyness. Who am I to judge, I was just like him a second ago. I guess I'm not so alone after all...

"Sure, I think that's a good idea. C'mon, let's find a spot that's less... crowded." I extend a hand as I nod towards one of the corners of the room. He gently takes my palm and gives a bashful smile, looking up to me with gratitude and embarrassment. I lead him over to the spot I chose, hoping no one is looking at us. Once we clear most of the crowd, I suddenly feel Casey tug at my arm as he seems to stop in place. Before I can manage to turn to see what's wrong, I feel the bare, smooth skin of Casey's body press against my back as he hugs me from behind. I begin to fluster as I feel his stiff nipples and cool metal cage press against me, yet I also notice his silky hair brush against the base of my neck as he nuzzles into me.

"Thank you..." I hear Casey whisper to me as he gives one final squeeze before letting go. The embarrassment from being so closely pressed against another naked boy is pushed aside by the compassion I feel for him. I turn to face him, dropping my belongings and taking both his hands in mine. When I look him in the eyes, I see him tearing up a little, clearly overwhelmed by the entire situation.

"It's okay, I'm here." I say softly as I give him a reassuring smile, trying to show a confidence I don't exactly feel in truth.

"I know I should just do it... I just... it's so embarrassing and..." He begins to stammer as he lets go of one hand, using it to wipe away the moisture from his eyes.

"Shhh, it's okay. We can go through this together, alright?" I use the hand he released to pat him on the head as I continue to console him, though the soft moment lets me gather my courage as well.

"Yeah, okay..." Casey gives me a quick nod as he gives a small smile. Jeez, he's cute...

"Here, I'll go first." I return the nod and organize my belongings on the mat below me, placing the cushion we've been given on the ground and kneeling next to it.

"Are you sure?" Casey asks, finding more of his voice now that he's vented some emotion.

"Yeah, it's okay. Just, you know... be gentle..." I say, growing bashful once again as I place my arms and head against the pillow, pointing my ass towards my shy femboy partner.

"Okay, I will." I hear him speak, though it's barely audible. It seems he is speaking more to himself now, steeling his resolve to continue with this insanity. I feel the padded floor warp beneath my knees as Casey kneels down behind me, causing my heart to flutter knowing what is soon to unfold. I hear the wet sound of lube being pushed out of the small bottles we were given before I feel one of Casey's delicate hands press their digits into one of my cheeks. For a moment it seems like he is trying to knead my butt as his fingers press into my admittedly ample ass. Just as quickly though, he moves his hand to grip and pull, exposing my entrance. I hold my breath and shut my eyes, waiting for what is to come. After a long couple of seconds, I feel a cool sensation brush against my hole. I reflexively tighten before I am **** to exhale, causing my ring to loosen in tandem. When I am finally able to focus on what I can feel at my rear, I notice the cool slickness of the lube starting to coat the puckered flesh of my ass. As Casey runs his fingertip over the entirety of my entrance, I begin to feel a slight tingling sensation. It's... it feels kind of nice... A faint warmth spreads through my groin and chest, more from the situation than the actual sensation, but that too is not unwelcome. The constant slick friction of Casey's finger running over my hole causes the coolness of the air against me to be replaced with a comforting heat.

"You can, um... keep going." I manage to speak through my embarrassment and confused enjoyment, telling Casey to move forward with our 'lesson'.

"R-right...!" Casey says with partial conviction. At this, I feel him stop running his finger over my rim and place it right at my center. For a moment he seems to hold there before slowly pushing in. I feel myself tighten at the pressure, but I concentrate on relaxing myself to allow Casey inside. I feel the wires in my brain cross at the feeling of the intrusion while I intentionally loosen myself before he suddenly slips inside. I stifle a small yelp. The faint tingling pleasure of his finger against my entrance is altered by the new sensation of his digit now slowly caressing my inner walls. He moves quickly from just his fingertip, pressing all the way to his knuckle as I feel the rest of his hand press wetly against the lubed skin of my rear. Despite knowing how small his dainty hands are, I still feel as if I've been filled - causing me to let out a small, high pitched whimper. Casey pauses then, presumably waiting for me to loosen again, my ass having clenched down on him like a vice. He lets go of my butt cheek then, and I feel him shuffle forward so he can rest that hand on my back.

"I-it's okay. Like you said, I'm here. We can do this together." He says in a wavering voice, though I know it's the most encouragement he can muster. The gesture and calming touch still reaches me and I feel myself begin to relax again. Moreso, the warmth of Casey's body heat as he hovers so close to me fills me with a faint sense of intimacy. I bet Sarah would do the same... Thinking of Sarah in this moment makes my heart thump in excitement as I am reminded of the finger up my ass. Casey begins to twirl and curl his finger inside me, making me feel strange. A minute passes of this and my excitement begins to wane, the lack of new pleasures disappointing me. Just as I was about to try and stand, I feel a rush of heat wash through my butt and into my cock as Casey's finger pushes against a new spot inside me.

"Wait! Go back to that spot..." I nearly shout to Casey, wanting to feel that strange new sensation again.

"Oh! Alright... Um, here...?" Casey moves his finger slowly around inside me, seeming to outline the spot that made me feel the new heat. The sensation is tantalizingly faint, the brushing of Casey's finger causing a glacial pressure to grow beneath my caged dick. I begin to bite my lip as I silently beg for more in my mind. There's something there, he's just not hitting it... Not wanting to seem like a pervert, I simply lie there, being tortured for a few more minutes. Finally I hear a voice address the class from across the room.

"Okay boys, time to give your partner a try!" Brit claps her hands and I hear the shuffling and sliding of skin against the padded floor. Casey quickly removes himself from my hole, making me both relieved and disappointed. As I rise to a kneel, I feel a rush hit my head.

"Alright, your turn Casey!" I say with more enthusiasm than I meant to. He simply nods however, the same shy smile on his blushing face, causing me to feel another pang of emotion in my chest for the adorable boy. He turns and bows down, already having arranged his cushion and belongings so we can start right away. I can't tell if he's eager or just found some more courage to press onward. Regardless, I shuffle over and perform the same actions he had with me. I start by kneading his ample ass, genuinely impressed with his butt. This would belong on any girl or futa, holy smokes... I probably play with him a little too long, and then move on to spreading him apart to get a look. What I see is a tight pink star, twitching with anxiety. I grab for the lube and apply a generous amount directly to his ass, causing Casey to let out a small yelp from the chill liquid. I smile to myself knowing I essentially did the same and knowing he is doing his best to relax, just as I had. I run two fingers up and down his crevice, staying close to his pucker. I massage him with the tip of my finger, making circles over his entrance. Surprisingly, the motion seems to relax him as I see him begin to loosen somewhat. Taking the opportunity, I quickly press my fingertip into his ass and slip inside. I only go as far as a single fingerbone, hearing as he gives the tiniest of yelps. His ass seemingly trying to crush my finger, I place my off hand on the small of his back and slowly run my palm across his skin.

"Shhh... It's okay..." I half whisper to him as I caress his pale skin. After a moment, I feel his body vibrate as he lets out a long sigh, and his ass slowly loosens around my finger. At that, I begin to work. I gradually slide the rest of my finger inside, still rubbing his arched back as I whisper little affirmations to him. When I curl my finger downward towards his front, I feel myself make contact with a harder portion of his inner wall. When I press down and slide my finger back in, Casey's whole body flexes, his ring tightens around my digit as his back arches, his head shooting up to look straight forward.

"AaaAah..." A strange noise erupts from his mouth, a mix of surprise and what I only assume is pleasure. I feel the eyes of some closer boys shift towards the sudden noise, but I pay them no mind.

"Was that good?" I ask with a combination of pride and coquettishness. I can't help but toy with him considering how easy it is, but I also feel good about helping him understand how close he was to pleasing me.

"Uhm, y-yeah..." He sputters out, still speaking at a higher volume than I'd expect. I smile an evil smile then, intending to find his g-spot again. As I wriggle my finger around inside, I manage to again find the soft nut that must be his prostate. This time, I simply brush around it's edges, occasionally pausing to instead push slightly on it. Every time I do, I hear Casey stifle a groan. By the time I hear Brit call out to the class again, I can smell a scent of sex wafting over to me from Casey, his flat cage leaking a stream of clear fluid.

"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." Brit walks between the rest of the boys, having them clean up as I finally retract my finger from Casey's thoroughly teased hole. When he rises to a sit, his face is completely flushed, though this time his expression is not wholly one of embarrassment. He looks me in the eyes for a moment as we silently smile to each other before he quickly looks away, putting his hands to his face as if to hide from me - not that there's much he can hide now.

"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." Brit finishes as Audrey returns to our side, handing both Casey and myself the small metal plug. As I examine the toy, I can't help but wonder if it could really feel that good if it's inside you all the time. It's not particularly large, only a couple inches long. Even still, it's far wider than Casey's finger was. Maybe it can hit that spot... I shoo away the thought, embarrassed at my own perversity. Determined not to seem a coward in front of Casey, I coat the device in a layer of lube and quickly line it up behind me as I perch on all-fours. It takes a moment of pushing, and the pressure of the plug's width almost makes me lose my breath, yet I feel it slide inside once it passes it's widest segment. I feel myself grunt as I feel the edge of the plug brush against my spot, yet it doesn't last long; the shifting of my position being enough to move the plug - or my prostate - away from one another. I turn to see Casey watching me with admiration before doing the same. A cute expression of concentration washes over his face as he does, his eyes slamming shut as the plug seems to slide into place.

As we dress in silence I keep my eyes to the floor, too distracted by this new sensation that continually prods my backdoor. When Brit and Audrey dismiss us and the guard futas return to escort us back to our dorm, I am surprised by a small peck on my cheek. Casey leans away from me, having just planted a tiny kiss on my face.

"Thanks again for helping me." He says with the most embarrassed smile I've ever seen, yet it's still an endearing moment. Wait, he just kissed me... he doesn't like-like me, does he...? I wonder with sudden confusion. I'm **** to brush the thought aside as he skips away toward the rest of the boys as they are herded by the darkly dressed futas that have arrived to escort us back to the dorm. Not wanting to get in trouble, I follow along. I spend the rest of the evening in small talk with Casey, ignoring the possibility that he might have some sort of crush on me.

It's not like there's a problem if he does... I think as I drift off into uncertain sleep that night.