“I think I would like to watch you masturbate sometime, if that’s alright.”
Castiel watched apprehensively as Dean paused, a beer bottle half raised to his lips. They were settled in Dean’s bed for movie night, Dean’s laptop resting at the foot with an old Western playing.
“I mean, we could do it now if you want,” Dean smirked, the blush on the back of his neck slowly creeping up to his ears.
“No, I mean… I want to watch you without you knowing I’m there,” Cas said slowly, shifting uncomfortably. “I believe it’s called voyeurism.”
“You mean you haven’t done that already?” Dean asked, his eyebrows raised in genuine surprise.
“Of course not,” Cas protested. “The thought has crossed my mind, but without your permission it seemed too invasive.”
“This from the guy who watches me sleep,” Dean remarked, taking another sip of beer.
Castiel frowned. “You’re at your most vulnerable when you’re asleep. I’m jus-”
“I’m teasing you, relax,” Dean rolled his eyes. Castiel regarded him with baited breath as the hunter pursed his lips and thought about it for a few moments before nodding.
“Yeah, sure. We can try it.”
Working out the technicalities took some discussing. Dean didn’t want Castiel constantly hovering over him on the off chance that he might start masturbating and Cas didn’t want Dean to know he was there, watching. They eventually settled that when Dean did feel like being watched, he’d just send Cas a dirty prayer. Whether the angel showed up or not was up to him.
Castiel ignored the first three of Dean’s “booty prayers,” as he called them. Responding to the first call seemed too obvious, as did the second. Not heeding Dean’s third call was to help him truly acclimate. He wanted Dean to get used to the thought that he might be being watched during his most intimate moments. He didn’t want to run the risk of the hunter holding back just because he thought he might be being watched. He needed Dean to be as comfortable with the thought of being looked at without truly knowing about it as much as possible.
The fourth “booty prayer” came one dull and rainy afternoon. Castiel sat in the library reading a book Dean had lent him while Sam tried to teach Jack how to play poker at the war room’s table. He heard Dean’s voice husky with want echo through his mind, pulling him away from Vonnegut’s words. He pursed his lips and glanced into the war room, making sure that Jack and Sam were focused on their cards before quietly slipping out of the room and down the hallway. Once he rounded a corner, he willed himself directly into Dean’s room, being sure to make himself invisible. The sight before him was better than he ever imagined.
Dean was on his back, his legs splayed as far as his bed would allow. He was stripped down to just a white lacey thong, the head of his cock peeking up over the hem, his hardening member straining the delicate fabric. One hand ran over his blush dusted chest, occasionally pausing to tweak a nipple or drag a finger over an old but sensitive scar. The other was raised to his mouth, Dean hungrily suckling two fingers while making obscene coos and slurping noises.
Castiel licked his lips and felt his dick stir in his pants, knowing what Dean was fantasizing about. The hunter always loved to tease himself just like this while sucking off Castiel. He said it made him hot, wanted the angel even more. Sometimes Castiel’s moans and praise would be too much and Dean would reach down and begin pleasuring himself and those were the times Castiel had to bind his wrists behind him. Not that Dean ever minded.
The angel watched rapt as Dean’s wandering hand moved lower, skirting around his now flushed head and gently scratching up and down the inside of his thighs. Dean removed his fingers from his mouth with a small wet popping noise and nudged the thong aside with a slick finger, circling and prodding at his hole.
Castiel had to bite his lip to keep from groaning, wishing it was his tongue teasing Dean’s ass like he’s sure Dean was imagining. It took quite a bit of convincing before Dean let Cas’s mouth anywhere near his ass. Castiel hadn’t entirely understood why since seeing a twink being thoroughly licked always made Dean achingly hard when they would watch porn together looking for ideas.
“It just seems weird,” Dean had said, avoiding eye contact while his ears turned red. “Yeah, it looks hot, but… I don’t know. You could try it on me sometime if you want, but I don’t think I want to eat ass. If it tastes gross don’t rub it in or anything, okay?”
After thorough experimentation, they discovered Dean loved to have his hole teased, but having a tongue inside him “felt weird. Good, but more weird.” Sometimes Castiel would hold the other man down and lick around him until the hunter was a babbling mess, trying to rut against the sheets for any kind of friction against his dripping cock.
It didn’t take long before Dean’s free hand descended to rub himself through the delicate lace and Castiel found his hand mimicking Dean’s, groping his heavy erection through his pants. Dean looked so good with on hand fondling his balls and the base of his shaft while his other fingers made broad laps through his crack, Castiel found it difficult not to blow his cover and go join him. But Dean not knowing whether or not Cas was watching was exactly what the angel wanted and he was not about to spoil such a magnificent show put on just for him.
Dean groaned and moved suddenly, rolling over and reaching into his bedside table. Castiel smirked hungrily as Dean produced a bottle of lube and Dean’s favorite plug from his nightstand’s drawer. Very carefully, the angel undid his belt and fly as Dean generously lubed his fingers, the angel’s mouth hanging open in a silent “oh” when his fingers wrapped around his own aching need. Dean’s mouth mimicked his own as he eased two fingers into himself, a cry escaping his throat.
Castiel watched with his lip tucked between his teeth as Dean slowly opened himself, whining and squirming over his sheets, his hand rubbing against the coarse fabric in earnest. Dean’s hips bucked up suddenly and Cas knew Dean had brushed against his sensitive prostate. Watching Dean undo himself was something he’d always wanted to see, something Castiel had fantasized about for years, and the reality was so much better than anything he had ever imagined. What he hadn’t realized was how frustrating it would be to stay silent and invisible, to not touch Dean and tell him how unspeakably beautiful he was in the throes of passion. Castiel felt as though he always had a great deal of self-control, but he could feel that control reaching its limit now watching Dean as he fucked his slicked fingers in and out of his pliant and willing ass, his moans turning into gasped words of pleasure.
“Fuck, so good!” Dean sighed, his hips bucking up again, precum beading out of his head and leaking onto his stomach. Castiel wanted so badly to stroke himself, to feel some of the same heat that Dean got to feel. But he didn’t dare move his hand. He wanted to come the same time Dean did, or as close to it as possible. There was no way he could do that if he started now. So he stood there, his cock twitching in his hand, silently begging for any friction.
Dean gritted his teeth and reached a hand into the already stretched fabric of his panties, desperately squeezing at the base of his shaft, his eyes shut tight as a whining groan escaped his throat. His cock twitched as the hunter stilled his actions and a blissed but frustrated expression came over Dean’s features as he denied himself release.
‘Such a good boy,’ Castiel thought, wishing he could actually praise Dean for handling himself so beautifully. He wanted to give Dean a reward. He pined to go over to him and plant kisses into his partner’s immaculately cut hips before sliding him into his mouth and sucking until Dean’s seed graced the back of his throat, his fingers curled almost painfully into the angel’s hair. But he controlled himself, reminding himself that watching Dean like this was what he truly wanted.
After collecting himself in his stillness, Dean removed his fingers slowly, whining when he was empty again. Taking his hand out of his panties, he moved into a kneeling position, coating the plug in lube as quickly as he could. Using one hand to hold the toy upright and the other to keep the thong held to the side, he slowly lowered himself onto the plug as he had onto his angel’s cock so many times before. Once he was fully seated, he wrapped a hand around his flushed and dripping erection and leaned forward until he was face down in the mattress, his ass up in the air as though begging to be taken.
As Dean’s hand moved over his cock, Castiel matched his strokes, his own head beginning to bead with precum. If he closed his eyes he could imagine it was Dean’s hand wrapped around him, giving him what he needed. He wasn’t going to though, not with how good Dean looked right now. The sight before him was so sinfully perfect he was tempted to reach into his pocket and take a picture with his phone so he could come back to it over and over. But that wasn’t part of what they had discussed so Cas just licked his lips and stroked himself at Dean’s pace, wishing the hunter would move his hand faster.
After what seemed like an eternity of Dean pumping himself in slow loose strokes, he reached back and turned the plug on. The hum of its vibration filled the room, its pulses making Dean jump and groan as he bit into the blanket beneath him. Castiel watched hungrily as Dean’s hand slowly stopped moving, his hips instead doing the work as he rocked back and forth trying to press against both the plug and into his own hand. From the look on Dean’s face he was getting close again and Castiel was certain the hunter wouldn’t deny himself a second time. Castiel’s strokes grew faster, his thumb swirling over his leaking tip when it reached the top. He was close, definitely as close as Dean was and it wouldn’t be much longer before they were both coming hard. He wasn’t sure if he would be able to keep quiet during his climax, not when Dean was putting on such a gorgeously wanton display in front of him and swearing into the sheets.
“Fuck! Fuck! Fuck me! Cas, Cas! Fuck me Castiel!!” Dean cried, his hips losing their rhythm and moving erratically before finally coming hard into his hand. Castiel followed soon after, his teeth clenched together tightly as he tried desperately to not make any noise, hearing Dean nearly scream his name completely undoing him as it always did.
The room stilled as they both basked in their afterglows, the continued vibrations of the plug and Dean’s heavy breathing the only things breaking the quiet. Dean moved first, reaching behind him and turning the plug off. Castiel let his eyes linger on Dean’s spent and blissed out form panting on the bed for a few more moments before moving himself to his room to change.
A knock sounded at his door not 5 minutes later as Castiel rebuckled his belt in a fresh pair of boxers and pants, the ones soaked in his semen lying discarded in the corner due to the absence of a laundry hamper in his room.
“Come in,” Castiel responded in a neutral tone. He arched a brow as Dean entered, totally clothed and shutting the door behind him looking very annoyed.
“Alright, if you’re not gonna do this whole voyeurism thing, fucking tell me,” Dean growled. “I don’t want to keep going at this solo when you’re right fucking here and ready to go.”
Castiel regarded Dean for a moment, his chest filling with a strange pride both at how well he was able to maintain his cover and how he was able to frustrate Dean without so much as saying anything to him. He merely stepped to the side and gestured to his discarded clothes on the floor, the white stain of his seed obvious against the inside of his black pants.
Dean frowned at first, obviously not sure what he was supposed to be looking at. When he saw the stained pants, however, Castiel could see the wheels turn and then something click, Dean’s expression turning from realization, to sheepish, to smugness within the course of a second.
“Guess that means you liked it,” the hunter smirked, sauntering past Cas to sit on his bed.
“Very much so. I would like to do it again sometime. But I understand if you’d like to return to having regular intercourse,” Castiel replied sincerely, turning to follow Dean with his eyes. “The entire time, all I wanted to do was to praise you and touch you. I don’t think you truly appreciate just how tempting you are.”
Dean licked his lips, his eyes slowly dragging up and down Cas as his ears turned red.
“Well, uh… if you wanna show me what you wanted to do while watching me,” Dean said invitingly as he reached forward, hooking his fingers in the angel’s belt loops and pulling him into his personal space. “I still got the plug in.”
Castiel smiled, bringing a hand up to cup Dean’s cheek, his thumb gently rubbing the stubbly skin.
“It will be my pleasure to show you.”