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Riddle never had a door in his room growing up.
‘Closed doors only invite secrecy and lies,’ his mother would say. He knew that was true because when he would stand in the dark outside her door, shaking from a nightmare, he couldn't ever bring himself to knock. In their house, a closed door might as well have been a solid brick wall; whatever was behind it—comfort, care, warmth—absolutely wasn't for him, only secrets he wasn't privy to.
‘Privacy is a privilege.’ she'd chastise, but a privilege was something that could be earned. He’d caught on that other children—much more unruly children—had doors in their rooms. He had been good, so why couldn't he?
‘What are you doing that you don't want me seeing?’ she’d press. Well…
Riddle could control his behavior, his personality, even the way he carried himself, but he couldn't control his body.
He'd learned about sex ed in school. Thanks to the extra lessons his mother gave him about medicine and health, he was certain he knew more about the subject than most of his peers. Silly was he to think if he took a clinical approach to it, he would be able to outsmart his own biology.
For a while, he lived with a false sense of security. His classmates started to struggle with their changing bodies—cracking voices, growth spurts, hormonal swings. For two years, he truly believed he was safe, that he was simply managing things better than his classmates. It turned out he was simply behind the curve.
His voice deepened, but never nearly as deep as his classmates’. He grew some, though unfortunately remained considerably shorter than his peers. Surely he would also be behind on hormonal changes… right?
Arousal was the very death of him.
He couldn't explain why he would grow erect while doing something as mundane as working on a math sheet or sitting at the dinner table. It petrified him. He wasn't sure what exactly he would say to his mother if she noticed. She was a doctor; surely she would understand.
As time went on, he shifted from being nervous about what exactly was arousing him and started worrying about what wasn't.
Why hadn't he become erect when he saw pretty women in revealing swimsuits, but when a guy in his class grabbed his shoulders in a strong yet playful hold, he had to hide his crotch behind his school bag? He couldn't understand. If his body was changing, why wasn't he developing the same interests as the men around him?
In middle school, he was completely aware that his classmates were engaging in masturbation—not something he wanted to know, but they didn't seem to care to try and be subtle about it. They acted completely shamelessly if you ask him.
Riddle couldn't masturbate. Not only did he lack a door, but his mother kept him on a tight schedule. If he took too long in the bathroom, it would be suspicious, and he couldn't imagine anything worse than being caught in such a filthy act by his own mother.
The closest he got to self-pleasuring in middle school occurred when he would wake up from a wet dream and attempt to subtly rock his hips into his palm under the covers—hardly pleasurable, not even enough to make him cum.
After moving into the housewarden’s bedroom during his second week at NRC, Riddle realized, for the very first time in his life, that he had true privacy. Not only did the room have a door, but also a lock! Unlike the first week at the school there were no roommates, only himself and a decently large bed.
Of course, it crossed his mind that he could finally give self pleasure a real try, but he only gave it a passing thought, simply too excited about the idea of being able to study in a room all to himself.
As with everything it seemed, that changed with his overblot.
Overblots are strange. The body gets put through so much stress that certain functions in one's body can get completely rearranged. There are so many adverse effects of an overblot even the studies on them admit they aren't aware of them all.
Riddle struggled with many. His back always hurt now, and sometimes when he blinked, his vision would go fuzzy for a bit. The most unforeseen effect, however, was an uptick in his libido. It made sense once he learned a little more about it. Certain studies have shown that overblots can cause abnormalities in hormones. If you take that logic one step further, an increase in sex drive isn't unthinkable.
For the first time, he had done it. He'd groaned, letting his thick cum spurt into his own hand. He could easily see why everyone was so obsessed with this kind of thing. He had never imagined it would feel so good.
Gradually, he'd gotten better at it too. Five times, he'd counted—five times that he had made himself cum since his overblot. That was a little more than once a week.
Sitting on his knees, the plush sheets of his bed pressed against his legs, he stared at the sight before him: a mid-sized box and a small squeeze bottle, both displayed neatly on his comforter.
The box was sealed, still encased in tight plastic film and the tube still had the protective seal over its opening. The items had been locked away in the housewarden's office for months, left unused and forgotten after being confiscated from a student last semester.
Even in his more strict days, Riddle still tried to show some understanding for other students' needs. If someone wanted to discreetly keep more risqué items hidden in their room and use them in private he wouldn't stop them; the Queen of Hearts wrote no rule against that kind of thing after all. Where he would draw the line was students flaunting their debauchery in public. This may be an all boys school, but that wasn't any excuse to behave like animals.
He had acquired this particular set of items from a troublesome third-year with an odd sense of humor. From what he gathered, it had been a joke rather than a genuine purchase. This student had laid the item out on the table in the main lounge while he teased another student, telling him he was ‘gonna need it’; of course that led to an immediate confiscation.
Riddle carefully picked up the box, frowning at the bold text ‘prostate massager’.
Normally, he would never do something like this. Just because an item had been confiscated didn't automatically make it his to take. but the items were brand new, and they'd just been taking up space in his office; if he did nothing with them, they would simply go to waste.
He tore away the outer seal layer and opened the top of the box, sliding out the thin plastic in which the item was encased. The plastic creaked and crinkled as he worked both sides apart and freed the object.
It was an odd shape, curved slightly with strange bumps. He lightly pushed into the outer silicone layer, but there was hardly any give. The very sight of it reminded him of how out of his depth he was. He hadn't ever even inserted a finger into himself before. Maybe this was too far of a jump.
Sighing, he let himself fall back onto his pillow, mostly upright but leaning back slightly. He had told himself he was going to try, and Riddle was never one to back down.
Setting the object and the tube beside him, he closed his eyes and let himself breathe for a moment.
Fantasy—that had been the first step in an article he had read about anal play. The only way to insert something into oneself without any pain was to relax, and the best way to force yourself into relaxation was to fantasize. The problem was, he didn't know what to fantasize about. To his great annoyance, the article hadn't elaborated on that.
Hands. Hands were a good start, yes? Everyone had hands.
He immediately ran into a wall when he tried to picture some and realized, even for something that simple, he'd have to make some decisions regarding the details.
He thought about gentle hands, well-manicured nails with slim fingers. It did nothing. Not only was he not becoming erect but he didn't feel any sort of heat in his lower regions.
He adjusted. Maybe the hands could be a little stubby, with chipped nail polish. He adjusted even more. Okay—no nail polish, stubby fingers with some calluses, the hands of someone hard working. Being a hard worker is an admirable quality, isn't it?
He adjusted even more. Large, strong hands with calluses! Hands that were well used from years of work. Hands that could be gentle if willed to but could easily manhandle him if required.
His legs shuffled uncomfortably. Apparently that was enough to get him started. He could feel the beginnings of heat building between his thighs.
Although it felt awfully embarrassing, he continued, not wanting to give up at the start. He pictured those strong hands grabbing at his waist and pulling him into place. As the thought formed in his head he allowed his body to slide further to lie with only his shoulders propped up. In his mind the hands traveled down to his hips, feeling over the side of his pants but purposely avoiding his ass and crotch.
The hands made their way back up, resting right where the hem of his shirt had begun to ride up. Letting out a small hum, Riddle lifted his own hands to sit right where he had been imagining the phantom ones. It didn't feel right. His were small, fingers skinny and feeble. It was quite the opposite of the picture in his mind, but it was the best thing he could do given the circumstance.
Slowly he pushed his hands up into his shirt, imagining they weren't his. If he really tried hard he could convince himself he was feeling those large, strong hands groping him. He was much rougher than he typically played with himself, pinching his nipples and grabbing his chest so hard he could feel his nails leaving marks on his skin. Between those moments though he stayed gentle, lightly ghosting over skin like an apology.
Eventually he grew impatient, allowing one of his hands to drift down to his pants while the other stayed playing with his chest. He slowly felt over one of his thighs, then slid back down, weakly palming at his hard-on.
He wasn't moaning, but he did allow himself to hum at the sensation. It took less than thirty seconds before he grew sick of that as well.
Huffing, he sat up. Maybe it was fine to be a little impatient. He was certain the imagined presence in his mind wouldn't be bothered. As he set his hands on his belt, ready to undo it his fantasy changed without him willing it to. His imagination now expanded past the hands; attached to them he could picture strong arms, well-built but not with so much muscle that they looked unnatural. Those arms worked to carefully undo his belt, he pictured the way this person's fingers would work, practiced but not perfect. If someone was touching him, he would hope they would be excitedly nervous as well.
After his belt had been discarded and his fly pulled down he shuffled awkwardly pulling his pants off his legs. For a moment he really did wish someone else was here with him, maybe it would make that action more sexy and less humiliating.
Leaning back and closing his eyes again, he continued. As the hand slid into his boxers and started slowly stroking him, he ruminated further. If someone was here helping him, they would be positioned over him, right? Surely that would be the most convenient position.
To adjust the image, he added to it. Of course, this person would have strong, sturdy legs—legs that could fit nicely on either side of his waist. Their chest… was harder to picture. He wanted to convince himself that this was just a muscular woman, one that had a more manly side but an equal womanly quality, yet all he could picture were strong pecs and a broad chest.
This person…. No, this man would wear a thin white shirt. Those words echoed in his head and yet in his brain, sat before him, was a bare chest. It was only fair. Riddle had on a shirt but no pants while this man had on pants but no shirt. All was equal that way. Besides, he wasn't exactly ready to imagine what would be hiding beneath them.
A chaste groan left his lips as he sped his hand up a little. Without him willing it to his mind tried to imagine the man’s voice, a deep yet genuine and familiar sounding voice that egged him on, telling him he liked Riddle's ‘cute little sounds’
That was too much. He pulled his hand away from his boxers so as not to shoot off too early. After taking a long, deep breath, he picked up the tube beside him, opened the top, ripped off the seal, and squeezed a decent dollop of the contents onto his fingers. It was unpleasant. The lube felt cold and slimy on his skin. Biting his cheek, he forced himself to move, slipping his hand into the back of his boxers. He would certainly end up making a mess of his underwear, but he hadn't been doing this kind of thing long enough to grow comfortable with full nudity.
‘You’re okay. I know you can take it,’ the voice in his head said. It was enough to get him to insert the first inch of his index finger into his behind. It was odd, but not completely miserable. Carefully, he worked it in further, rocking it a little before adding in more. By the time his entire index finger was inserted, he felt good about himself.
While adding the second finger, he retreated back into his mind. His fingers were much too slim to fit the fantasy, so he switched strategies. Instead of imagining the man’s fingers inside him, he imagined a strong hand wrapped comfortably around his wrist, guiding him as he pushed his own hand in and out of himself. ‘It’s best to use yours. They're smaller,’ he would say. ‘I wouldn't want to risk accidentally hurting you.’ Yes, that was it. A considerate partner is good.
By the time his third finger was inside and he felt thoroughly stretched, the man guided his hand away and reached for the toy beside Riddle. As Riddle lubed it up, he imagined the man slowly pulling the zipper of his trousers down. The way the man stripped himself of his clothes felt far more arousing than it had when Riddle was the one doing it.
The toy wasn't very thick and was only long enough to hit where it needed to. Despite that, when the man pulled off his briefs, he imagined him big and thick, almost unreasonably so. Just the idea of it caused his own, much smaller member to twitch.
Pushing his boxers to the side just enough so they wouldn't be completely in the way, he set the tip of the toy against his entrance, imagining the man lining up instead. Once more, the fantasy was broken. The toy was cold and hard, feeling nothing like he assumed a real dick might.
The curve of the toy pressing against his insides was weird, the entire thing felt different from what he had pictured. He shifted the massager around until he felt a strange sensation. It wasn't exactly pleasurable, almost like the tingle of bumping your funny bone, just lower in your body. Nervously, he held down the small button at the handle of the toy until it started to gently vibrate.
He was feeling something, but wasn't exactly enjoying it. He didn't panic. The research he had done on this kind of massager told him that it sometimes took a short while to start feeling pleasure from it.
After a minute, he started to feel what he was aiming for. It helped to imagine the man instead, his cock stationary, nestled deep inside of him, his face next to his ear whispering that he was doing ‘so good’.
Slowly, he began moving the toy in a steady curved pattern. He whimpered. His cock felt neglected, but he couldn't bring himself to touch it. The image of the man carefully rocking his hips only heightened the pleasure he was feeling. It was starting to become too much.
Attention was finally given to his dick, taking his free hand and starting to pump it. ‘Do you feel good?’ “yes!” Riddle replied aloud unintentionally. The man pulled closer, kissing his neck. Riddle almost thought he could feel the cold plastic of the man's glasses against his neck and his short hair tickling his cheek.
“T-Trey,” he moaned.
Lost in pleasure, Riddle couldn't help his thoughts. The ‘man’ he had thought up fully formed in his mind: green hair, glasses, and a smudged clover symbol on his right cheekbone.
No. The hand on his dick faltered as he grew close. Trey would be the type to tease. After hearing the vice housewarden’s playful chuckle in his mind, he continued his hand’s movements, starting irritatingly slowly but gradually increasing in speed. He would tease, but he wouldn't be completely cruel.
He felt like he was losing his mind. The thought of Trey’s cock pumping deep inside of him, of having Trey’s strong baker's hands all over his dick—he needed to see his friend sweaty and panting, what his face would look like warped with pleasure. As his brain fogged with euphoria, it flashed fantasies he previously had blocked himself from thinking: Trey calling him a good boy, Trey telling him he needed him, Trey on his knees wearing one of his collars, Trey spitting into Riddle's mouth. Everything nasty and horribly self-indulgent that had once seemed so wrong was now replaced with an urgent need.
The last thought he had before he came was of himself looking spent, dripping an absurd amount of Trey’s cum from his hole. He let out a moan that sounded closer to a yell as he came. For a short while longer, he kept the massager pressed against his prostate until he couldn't take it anymore and pulled it out.
Panting, he tried to let his mind catch up with his body. He was sure his skin was bright red and that he looked a complete mess.
He now understood the need for toys. That was the best orgasm he'd had in his life, though that wasn't a very tall order. When his high came down, it was replaced with an odd feeling—a deep, painful feeling of guilt in his stomach. He couldn't place why until his brain had caught up and realized what exactly it was he had just done.
He had just sexually pleasured himself to the thought of his closest friend, a friend who had placed a great deal of trust in him. Thinking so disgustingly of someone who thought so innocently of him, that's….
Riddle groaned to himself, his legs curling in on his body as he shoved his face into his pillow. The crash of going from previously unimaginable levels of pleasure to a deep, painful self-hatred left his body feeling hollow.
How absolutely filthy does one have to be to think of a friend that way? Surely, if Trey knew even just one tiny bit of the thoughts he just had about him, he would completely drop Riddle as a friend. Who would want to associate themselves with a nasty pervert?
Groaning again, his hands gripped tightly at his pillow. What had he been allowing to happen to himself? His mother was right, he should never have started doing this kind of thing. Freedom is a slippery slope; it can only lead to horrible things.
Sitting up, he stared down at himself. His skin was still patchy, and his boxers were soiled and barely covering anything. His cheeks burned with humiliation. If anyone could see him, if Trey could see him right now… what would he think? This was completely unbefitting of a housewarden. He was supposed to be setting an example, not stealing things from the confiscation bin and using them to facilitate such horrible feelings about his second-in-command.
Snatching his magic pen from his bedside table, he conjured over a fresh, clean set of clothes. Once he had changed, he forced himself to his feet and made his way to the bathroom.
‘This can absolutely never happen again,’ he thought, the sink water rinsing off the phallic item that had just been inside him.