Work Text:
Chase found himself in these sorts of situations embarrassingly fast when it came to Carmen Sandiego. The thief had managed to cuff him to the metal bar on the train seat she'd been sitting on just a moment before. With his own cuffs, no less. It was maddening.
He could not understand how he found himself in these situations over and over. He was always so sure that he would catch her this time.
As it turned out, today was different. But for another reason.
Agent Argent was not the one to find him in this rather compromising position. Chase had tried fruitlessly to free himself, ending up facing the chair with his buttocks awkwardly jutting out.
Instead, it was someone else.
Suddenly, there was a touch to his shoulder. A sure, steady hand slid down his spine and Chase puffed up, enraged.
"I don't know who you think you are, but you will uncuff me immediately!" he started, working himself into a fervour until it was very suddenly snuffed out.
Two large hands cupped his ass through his pants, thumbs stroking over his waistband.
"Now, now, Mr. Devineaux, I will do no such thing."
The voice made Chase stop in his tracks. It was so calm, commanding, that it burned his rage out into a tiny flame.
"But- but-!" he sputtered, gasping when the hands on his ass squeezed.
"Mr. Devineaux, as I understand it, you are here because you tried to catch a certain little Red Riding Hood. Now, I cannot let that happen. So I am here to win your allegiances another way."
Chase was stunned. This guy was working with Carmen Sandiego? And he wanted to-what? Make Chase join that Scarlet Superthief?
He would never manage—
A gasp was punched out of him. His pants and underwear had very suddenly been pulled down to bare his ass to the cool air of the train compartment.
The thumbs pressed into the dimples on his back, before the hands slowly slid down further, thumbs spreading his ass crack to the world. And the eyes of this stranger.
Chase sputtered, trying to come up with a dignified way of getting the respect he deserved. The thought stuttered when he suddenly felt the man's breath ghosting over his ear.
"I will teach you patience, dear Mr. Devineaux. And once I am done with you, you will see that it is infinitely more valuable to gather all the information, before plunging into action."
His words were punctuated with a firmer stroke of his thumb down Chase's crack and he squeaked.
This was not- happening, was it?
"I do not know what you think you're doing, but it will not work! I am Chase Devineaux, esteemed-"
The rest of his indignant speech was muffled by a piece of cloth that had been pushed into his mouth. He tried protesting but that too was muffled.
He was gagged.
"There you go, Mr. Devineaux. You must focus if you ever hope to achieve excellence. All this chatter will not help anyone."
Chase shook his head, still trying to argue through the cloth in his mouth.
The man ignored him, obviously letting his attention draw downwards again to Chase's bared buttocks. The hands squeezed, before spreading him wide.
"I will be gentle, Mr. Devineaux. You'll find my method of teaching pleasurable, I assure you."
That was all the warning he got before one of the hands disappeared for a moment, only to reappear wet. He squeaked when the man's wet thumb slid down his crack with firm pressure, stopping at the tight ring of muscle that was his hole.
Chase squirmed at the strange sensation, protest muffled.
The stranger stroked his other hand down Chase's back, holding him by his tailbone and muttering "Breathe, Mr. Devineaux. Just relax," as he slowly pushed his thumb against the ring of muscle over and over before sliding inside.
Chase gasped. Now that- that was- new.
The man chuckled into his ear, rubbing his thumb along Chase's inner walls, sliding it deeper into him. Suddenly, it brushed over a spot inside of him that had his back arch.
"That, Mr. Devineaux, is your prostate. You will be well acquainted with it, once we are finished."
As if to emphasise, the thumb inside of him rubbed over the little bump in slow, methodical circles that had his knees buckling. His cock was very much interested all of a sudden.
His pants were getting tight, since the stranger hadn't bothered to take them off.
After a few more moments of this confusing, arousing torture, the thumb was slowly pulled out. Chase breathed a sigh of relief, that was quickly transformed into a ragged gasp when instead, two of the man's fingers pushed into him, swift and steady.
Chase couldn't help whining. It felt so strange.
The fingers pushed deeper into him, spreading him like he'd never been spread before. They crooked, rubbing over that spot inside of him and Chase couldn't help crying out into the gag.
"It feels good, does it not? Good, it will help you focus."
The voice was calm in his ear, soothing almost.
"You are free to orgasm if you wish. It will not hinder the process."
Chase was confused. Orgasm? Process?
The fingers rubbed more insistently and he choked on a moan, hips twitching. Oh. Orgasm. Yes.
Another tight circle of those fingers and another, and he came with a shout, whimpering into the gag as his head sunk forward onto his bound hands, ass angled eagerly towards the stranger.
"There, there. That's good, Mr. Devineaux. Very good. Let it all out."
Chase's cheeks flushed crimson at the praise, squirming as the stranger continued to press into his prostate with the same awful precision. Overstimulation had him whimpering.
His squirming didn't change anything though. Eventually, the man pulled his fingers almost all the way out, but only to squeeze another into him, continuing to rub his prostate as he did. And eventually another.
Chase had tears in his eyes by the time the stranger was up to four fingers, consistently, unwaveringly massaging his prostate. It ached, arousal shivering through him constantly.
The man's other hand, which had been steadily holding him still at the waist, now slid down, tracing his rim, where it was stretched around his fingers. A little pressure on the sensitive skin and Chase gasped, another orgasm overwhelming him, hips twitching weakly.
"Huh," the stranger commented. "Sensitive. Very interesting. This should go faster than expected, Mr. Devineaux."
Chase could hardly comprehend what he was saying.
Then the fingers slid out of his ass and he couldn't help whining. His ass was spread wide again, large hands holding him open. The man's thumbs dipped into his hole and pulled, opening him up. He squirmed with shame.
No one had ever-
The man let go. Fabric rustled behind him. Then the hands were back, holding him tightly, calmly.
Something brushed up against his skin and he squeaked once more. The man was-!
The man's erection slid along his crack, once, twice, before, with measured pressure, it started sinking into him. At first Chase was convinced it wouldn't fit, thrashing in his bonds but the man ignored him, slowly pushing deeper and deeper into him until he could feel the man's hips pressing against his ass.
"Ah, yes. There we go, Mr. Devineaux. Patience."
He groaned when the man settled deep inside of him. Then he pulled out and pushed back in. He set a slow, deep rhythm, pushing all the way into Chase over and over.
Chase was trembling. He came again not long after, legs giving out so he was held up by the man's hands wrapped around his waist, spreading him around the man's cock.
He was crying from the constant assault on his prostate.
The man spoke again.
"Precision, Mr. Devineaux," the man angled his hips, driving directly into Chase's prostate, "is very important in our line of work. You must," another thrust right into the abused bundle of nerves, "always," another, "gather all the facts," another, "before you engage."
The man was consistently hitting his prostate now on every thrust and Chase was crying openly, gasping for breath at the painful overstimulation, scrabbling for purchase against the seats and finding none.
His muffled pleas went ignored.
"You will orgasm until you run dry. Then you will orgasm again. And only then, Mr. Devineaux, will you be open to listening. If you had been willing to listen prior to this, we could have avoided such drastic measures."
The man's voice was calm and collected, despite the way he was driving into Chase with powerful, slow thrusts. Chase all but screeched when the man hilted himself and ground against Chase's ass, rubbing against his prostate relentlessly.
One of the man's hands moved to pull his pants and underwear down fully, revealing his sore, still hard cock. The hand closed around his balls, massaging them and Chase cried out once more.
"It stimulates blood flow," the man explained calmly, "to help you orgasm."
Chase sobbed. Then the man pulled out, and thrust back in, squeezing Chase's balls.
He came again, a pathetic dribble of come running down his length.
"Hmm," the man hummed. "I wonder how many more until you run dry. Perhaps one will be enough already."
The man reached up and closed his fist around Chase's poor cock, stroking him in time to the powerful thrusts. It had him wailing into the gag, overstimulation too much to bear. His voice was thick with tears, sobbing and shuddering on the man's cock.
Again, his pleas were ignored.
He came again with the stranger's hand squeezing at the head of his cock, coaxing more come out of him. It was barely a few drops.
"Looks like you're dry, Mr. Devineaux. One more then you'll have made it. Very good."
Chase shuddered, whining and shaking his head wildly. No more! He couldn't do it-
"Ah, Mr. Devineaux. Your doubts are unfounded. You will come again. Then you will be open to truly learning. Don't fret, it will be over soon."
A hand stroked down his spine before resettling at his hip. The other was still working his abused cock.
"Now I understand you will need a bit more encouragement for this orgasm," the man explained, the hand on his cock disappeared. Then reappeared. A quiet buzzing filled the space between them.
The vibrator was held to Chase's cock and he shrieked at the intense wave of pleasure-pain that rolled over him. It was set way too high. The vibrator was slowly drawn down his shaft, pressed to his balls, and back up, pressed right to the underside of his cock head.
Chase sobbed. The thrusts into his body were deep and slow, maddening. The vibrator was unrelenting.
His arousal crested. The orgasm tore through him, but he was too exhausted to do much more than sob into his cuffed hands.
The man slowed his thrusts, deep inside of Chase, letting go of his cock.
"Very good," he said. It sounded very far away. Chase was drifting off, losing consciousness.
When he woke again, it was to Agent Argent's voice calling him. He took stock of his body. His buttocks hurt. His cock was sore and felt spent. He was still locked up to the chairs but he was once again fully dressed.
For a moment he believed it may have just been a dream.
Later, he found out that that was not the case. He'd found three things that were new once he'd had the privacy to look through his belongings:
One, the plastic cage wrapped snugly around his now blessedly soft, spent cock.
Two, the vibrating plug that was buried deep inside of his ass. The fact that it vibrated was something he would find out later.
And three? An origami bird, which contained the following message:
Dear Mr. Devineaux. Your training has only just begun. The study of patience and focus demands time. You will find the gifts I have left you to be excellent tools to practice both patience and focus. I will leave you more instructions whenever you may need them.
For now, wear the plug whenever you are out working. It will teach you to sharpen your focus beyond any outside distractions.
Do not try to remove the cage, it is impossible. It shall teach you patience. You are not able to become aroused in it, Mr. Devineaux. Without patience, this is sure to drive one mad.
I will watch your progress with interest.
Until next time,
Shadowsan.