Riley

Hesitantly, I look around the room for an anchor - anyone to help me through this moment. I know Audrey and Brit probably won't punish me for doing nothing, yet I feel myself freeze up from fear - not of the instructors but of the reality that I'm standing here naked, expected to have another... boy... stick his finger in my ass. The situation is overwhelming me as the seconds crawl by, even though I haven't argued with - or thought about - any of the events that have led up to this moment.

"You okay, Sam?" I jump as the pitched voice of my friend Riley comes from behind me. When I turn, I see him standing only a few feet away, hands on hips and blonde hair draped over one shoulder with very clear flushing on his smiling face. Clearly he's both excited and embarrassed from what's unfolding here, the confidence of his bold-stanced nudity undercut by the red of his face. Clutching my cushion in front of my chastity cage to hide myself, I feel my shoulders loosen slightly at the sight. That's right, at least I'm not alone here with a bunch of strangers.

"Oh! Yeah, yeah I'm fine. Do you want to, uh... do this...?" I stammer out, unsure of how to ask him to be my 'lesson' partner.

"Like, be partners? Sure! I've already done it a little myself. Though I know you and everyone else in the dorm already knows that." He gives out a little giggle of embarrassment at the admission. I would practically pass out if I said something like that knowing it was true. Instead I focus on his agreeing to help me out.

"Why don't I start?" Riley says as he makes his way over to a clear spot on the padded floor, assuming I'm following. I have to speed-walk over as he throws his cushion and clothes bin on the ground beside him, doing the same as I catch up.

"Oh, sure. I-I mean, I guess I can..." I begin to fluster all over again. He wants me to go down first..!? I don't know if I'm ready to- I don't manage finish my anxious assumption that he was going to finger me so soon. Instead, Riley himself kneels down, ass thrust into the air and pointed right at me.

"I'll tell you if I feel anything and guide you if I can." He says, his face now smushed into the floor. Oh! He meant that he would be the first to be touched... I consider with a mixture of relief, admiration, and slight shame. At least I have time to prepare myself now, yet Riley's readiness to perform this lewd act with someone he's known for such a short time causes me to be jealous of his courage. Following his lead, I sit on my knees next to him. I reach for the small tube of lubrication that came with our clothes bin and squeeze a large drop onto my hand, rubbing my fingers into the slightly sticky moisture.

"Alright, are you uh... ready?" I ask. Unsure of what to do with my other hand, I rest it on the small of Riley's back to try and signal to him I'm all set.

"Mmmmm... yeah, just let me relax." Riley seems to grow goosebumps at the skin-to-skin contact, though his voice carries an undertone of nervous excitement. He takes a slow, deep breathe before sinking further back on his knees, exposing the privacy between his cheeks. As I watch waiting for his confirmation, I notice Riley's lithe body has gained some shape since I first met him. Not a significant amount, but his butt has gained some jiggle and his thighs actually touch when his knees press together, causing his pink cock cage and balls to be hidden by his legs from my angle of vision. I could probably pretend he's a girl with how he looks and sounds, now... I consider, **** to reduce the level of gayness I am being **** into. After all, I like women.... Something about this thought doesn't feel fully convincing, but I don't have time to dwell on it as Riley speaks up.

"Okay, I'm ready. What are you waiting for, Sam?" He gives his ass a little wiggle to signal his enthusiasm, causing me to blush. Taking a silent breath to steel myself as well, I slide my hand from the base of Riley's arched back to lightly grab one of his cheeks and spread him open a little further. Expecting to see something similar to Audrey's display from before, I instead see Riley's slightly darker anus - a fleshy slit nearly the size of my thumb. It lacks the cuteness of Riley's image or the pink donut on Audrey, yet the sight is still rather lewd, causing a heat to rush to both my cheeks and crotch. As I bring my lubed finger closer to his ass, his slit flexes at me, seeming to almost open in anticipation. I lightly touch the wrinkled skin and run my slick finger around his rim. Riley simply lies there silently as I get acquainted with his butt, slowly getting a feel for the soft and sensitive skin. After a minute or two I pull my hand away, looking to re-lubricate my fingers for the next step. Before I grab for the bottle, my eyes linger on Riley's moistened ring. The darker skin seems to have risen slightly to give his already lewd appearance an even lewder, puffy look. When Riley gives me another anal wink, I am surprised to see a thick drop of clear fluid emerge from inside his ass and trail down his smooth skin. Is he getting... wet...? I wonder as I continue to lube my fingers. That's our treatment kicking in, isn't it.... The comparison to a girl keeps getting easier...

I return my hands to Riley's body, one pulling a cheek away from my area of interest while the other lightly presses against his hole. I hardly give any pressure before the tip of my finger slides into his spacious entrance. I pause from the slight surprise and sensation. Despite the ease of entry, Riley's insides are relatively tight as his body reflexively grabs it's intruder. I pause for a moment, letting Riley relax a little again before I begin to slide my finger in and out, running between the tip and second knuckle of my digit. His entrance is slick, giving tiny wet noises as I work, feeling around in his soft and squishy insides. I feel my dick press against my cage as I find a rhythm, the occasional squeeze as Riley's body grabs my finger, causing me to wonder what it would be like to put my dick inside this hole instead of just my finger. If I imagine it's Sarah I'm fingering, it's even hotter... I close my eyes for a moment as I have this thought, continuing my motions until I find the dense round spot inside Riley's inner walls and give a slight push.

"Ah..!" Riley gives out small, girlish cry of surprise at my discovery, causing me to stop.

"Was that the right spot?" I ask tentatively, hoping I didn't hurt him by accident.

"Oh, you were doing pretty good. You definitely found my prostate..." Riley responds, his croaking voice laced with arousal.

"Okay, I'll keep going." I say with the most comforting tone I can muster. I feel a small rush of fluid brush against the finger that sits inside my lesson partner, causing his interior to re-lubricate without needing any assistance from me. My finger still resting on the little nut that is Riley's prostate, I begin to circle it with my fingertip, pressing lightly to try and find where it's edges lie. Riley lets out little breaths and soft moans as I work, fully focused on learning how a boy's body is shaped and feels. We continue like this for several minutes, my finger slowly running over Riley's pleasure spot and applying varying levels of pressure. I feel as if I had managed to push away some of the flesh that hides his button to give me easier access, but as I begin to curl my finger down onto it like Brit and Audrey had said, things suddenly change. As I flex my finger , Riley gives a long, low moan as his asshole tightens around me. However, despite my apparent success I find I lost much of the area I had revealed of his prostate. Just as I had begun to retrace the area I had found it in before, I hear a voice call over the room.

"Alright, good job boys and sissies! Time to swap positions with your partner. You all need to get a chance." Brit says as she walks around the room, getting a good look at every pair of boys at different stages of engagement. I withdraw my hands from Riley, somewhat disappointed I didn't get to finish my exploration of his inner workings.

"Aww, oh well. You did great Sam! That was super satisfying, even if I didn't cum." Riley says as he rises from his bent position.

"Now it's my turn to make you feel good, okay?" He says, giving me a massive, red cheeked smile. His words are reassuring and his genuine smile gives me the courage to take the same position he was just in. I turn and take a massive breath before bending over on my knees, placing my head over my arms which I rest on my pillow.

"Don't you worry Sam, I'll be gentle. Now let me return the favor of that massage you just gave me." From behind me, Riley speaks in a soft and slow tone to keep me calm. I find I have to close my eyes to block out the sight of all the other boys bent over throughout the room. At first, Riley simply rests his hands on my hips, slowly rubbing my smooth skin in small circles. The repetitive motion and smoothness of his delicate hands actually does manage to make me more comfortable in this absurd situation. His hands slowly expand their range, reaching the point where Riley is now giving a deep massage to my ass cheeks. That, or he's just groping me... I feel him start to grab and pull at my ass, spreading my cheeks open so he could see right into my most private of spots.

"Hmmm... Your butt is so cute, Sam." I hear Riley say behind me as he holds my cheeks apart. I feel my cheeks burn hot with blood, grateful no one is directly watching us. Probably...

"Okay, I'm gonna try something. But don't worry, I bet it'll feel real nice." I hear Riley again after he paused for a short moment, a note of curiosity in his effeminate voice. I instinctively brace myself for whatever was coming, only to consciously focus on relaxing my anal muscles. What I feel next is wet and warm, but it certainly isn't a finger. Instead, a wide and rough texture slowly runs up my pucker as I inhale sharply from the shock. I feel Riley's warm breath waft over my skin as both his hands continue to hold my cheeks. Is he... Licking me!? My theory is confirmed when a second lick runs over my ring as Riley lets out a soft moan, the vibration of his voice running up my body from the contact. He continues as my toes curl from confusion and anxiety, yet the sensation is admittedly rather nice. His tongue slides and rolls over my ass as he picks up both speed and vigor.

"Oooh, brave little sissies, aren't we? Are you willing to really dive in then, my little ass eater?" I hear the girly voice of Audrey come from further behind us as Riley's tongue retracts for a moment. I find the sudden withdrawal to be disappointing, the warm and rough motions of his mouth on my ass was mildly pleasurable in a way I can't fully explain... like a crazy make-out session but better... The warm tingle in my stomach from the rimming I was getting is quickly replaced by anxiety, as I realize I am now being watch by someone else with my ass thrust into the air like some slut...

"Alright Sam, I'm going in again." I hear from Riley as the warmth of his face presses against my sizable cheeks. As his tongue begins to run over my hole once again, he suddenly pushes the tip inside, just enough for me to feel the change in sensation. I give out the tiniest of squeaks and hope no one heard, though I feel my ass tighten against the intrusion, practically pushing Riley's tongue back out of me. Even still, the warmth in my belly radiates out and connects with the heat of my caged cock, and I feel my ring loosen in anticipation for more. When Riley enters me again, his tongue pushes in further, pressing around the edge of my ass to get me used to the foreign - yet pleasant - experience. It takes several minutes of this for my butt to fully relax, the warmth that spreads through my lower half causing me to tip further towards horny rather than anxious. When I find the sensation hasn't improved in some time, I can't help but push back a little against Riley's tongue as I look for further pleasure. At this, Riley seems to shift tactics. Instead of simply running and rolling his tongue around my inner rim, he begins to search deeper inside me. For a long minute I find the sensation isn't particularly better, but it is different enough to be a satisfying change. When I start to feel a slight pressure every time Riley flicks his tongue towards my front, I can't help but let out tiny little grunts through my closed lips. Either Riley noticed my voice or discovered the source of my noises, but either way, he began to dig the tip of his tongue around my insides where the pressure was building. Suddenly, I feel as if I have to pee a little, yet the fuzzy warmth behind my caged dick starts to grow to a pleasurable heat. After what felt like hours of this tonguing, I can't help but start letting out my breath in little gasps every time Riley strikes my spot. Just when I realize the heat behind my dick had pushed out a long stream of precum from my cage, I hear Brit speak to the whole room once again.

"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." Riley retreats from me far too fast for my liking, leaving my ass to wink a couple times with longing. Both ashamed of my submission to Riley and of my temporary desire for it to continue, I simply sit back on my well-lubed butt as I clutch my pillow to my chest. Riley leans over to me as he sits on his legs, whispering to me with his blushing face and wet lips.

"That was for doing such a good job for your first time..." He breathes into my ear while Audrey and Brit congratulate or wrap up the other pairs of boys in the room.

"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 Riley and myself the small metal plug. It's only a couple inches long, but the width is even larger than Riley's tongue... I complain to myself, unsure how it will feel to have something so... filling... inside me. Even still, it seems I have **** once again. I grab the lube we are provided and get back in the bent over position I was in before. This time with my eyes wide open, I look between my legs and past my caged dick as I do my best to line up the plug with my rapidly tightening hole. Despite my new anxiety, I find I am still remarkably ready as the plug only needs a couple test pushes before it slides past my ring. I let out another breathy exhale as I feel it settle into it's new home, sensing my body tighten around the metal. For a brief few seconds, I feel the plug press against my prostate as my body flexes, but the moment is far too fleeting and subtle to give any lasting pleasure. The experience leaves me more annoyed than anything as I begin to dress myself along with the rest of the class.

When Brit and Audrey dismiss us and the guard futas return to escort us back to our dorm, Riley stays by my side and idly chats with me about nothing in particular. I welcome the quiet conversation for the walk and the rest of the evening as the new fixture in my ass is a constant distraction, causing me to drift between uncomfortable and horny until I finally manage to drift off to sleep hours later. Riley sure is nice... I wouldn't mind doing that again... if it was him.......