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Dean Winchester was straight. 1000% no homo, only into chicks, he swears. That doesn’t mean he was going to let his best friend fumble his way around a girl when he could help out and make it memorable. That’s all it was, helping Cas.
Dean offered to do most of the flirting, guiding Cas on this pick-up, and it worked well enough. Within an hour, a pretty brunette was softly kissing Cas in the back of the Impala while Dean drove to his motel. He was extremely glad that Sam was god-knows-where and not about to see him corrupting the sweet little angel with Ms. Green Eyes.
Dean parked the car, opened the back door so the two could stumble out, and reached for the room key in the pocket. The girl, Eliza, Dean believed, pulled Dean into a kiss, so he tossed Cas the key and guided her to the room, never letting up. Dean had to get a handle on himself, this was for Cas, not him.
“Cas, strip,” Dean ordered as they got inside. Cas fumbled with his coats and tie while Dean gracefully took off Eliza’s shirt. When Cas was finally shirtless, Dean beckoned him over.
“What’s off limits?” Dean asked Eliza.
“I don’t do anal without actual lube, and because I just met you guys, none of the hard stuff.”
“Oh don’t worry, we’ll be gentle. Right, Cas?” The angel’s eyes shot up.
“Yes. Yes, of course.”
Dean held back a chuckle before turning to Eliza. “Marking?”
“Nothing that can’t be covered.”
“Marking?”
“Hickeys, Cas.” Cas nodded in understanding and Dean turned back to Eliza and looked for any sign of reluctance. Seeing what he was doing, Eliza gave him a small smile and kissed him for a second before turning to Cas and kissing him.
Dean took this opportunity to start taking off his clothes. He tossed his jacket and flannels carelessly onto the floor before taking his shirt off.
He moved so his chest was to Eliza’s back and he kissed down her neck. His hands carefully snaked between her and Cas and carefully undid her belt. Taking the hint, Eliza’s hands moved from the back of Cas’s neck to his belt.
Dean carefully put his hands on Cas’s and guided them to where her bra was clipped. Luckily Cas seemed to know how to undo it and soon her bra was on the floor. Dean let her step to the side so she could shrug off the bra and remove her belt. Cas just stared at her in awe.
“Like what you see, big boy?” She asked with a smirk. Cas tried responding but found that he was speechless.
“In our defense,” Dean picked up, “you are absolutely gorgeous.”
“Such a sweet talker, I might have to take care of you first.”
“As tempting as that sounds, we both know that’s not how it’s gonna go down.” Eliza smiled and stepped towards Cas.
“Right, tonight is all about this cute angel.” Cas gave her a confused look, ready to ask about the angel bit when Dean shot him a look that told him to shut up.
Eliza pulled Cas towards her and unbuttoned his pants while kissing him. She started guiding him towards the bed. When they got to the edge, she pulled his pants down and gently pushed him so he’d sit. She sank to her knees and teased his dick with her hand while her lips marked his waist and thighs. When she decided she had teased him enough, she gently took him into her mouth and started bobbing her head.
Dean watched the display, trying to pay attention to Eliza and not the way Cas’s head tilted back with his eyes closed. He tried focusing on what he could do for Eliza and not the way Cas’s lips slightly parted as soft pants escaped him. He tried convincing himself that this was for Cas, and not the way he’d been curious about what his best friend was like under the suit and in this setting. He wasn’t gay.
Dean pulled himself out of his thoughts, unbuttoned his pants, and removed them so he was just in his boxers. He moved so he was on his knees behind Eliza. He trailed his hands down her side while he kissed her neck and down to her shoulder. He brought one hand up to gently toy with her nipples while the other went lower and rested on her thigh. She let out a moan that was muffled by Cas’ dick leading him to make his noise of pleasure.
After playing with her nipple for a bit, Dean allowed the hand on her thigh to move higher, faintly moving over her clit which stuck out from her mound, until he rested on her hip. At the same time, the hand that was on her breast moved to her hips as well. He moved up so he was flush with her.
“Why don’t we make this more fun?” Dean whispered in her ear. At her moan, he pulled the two of them up so they were standing. When Cas looked up, confused, Dean told him to stand up as well. He had Eliza lie down, and she followed.
“Alright, Cas. Now that she has given you head, we gotta repeat the gesture. Watch.” Dean knelt and used his hands to spread her legs. He kissed a trail from her inner thigh to her bikini line and allowed a breath to exhale as he ghosted her already-soaked pussy. On the opposite thigh, he repeated the action, but when he got to her core, he gently took her clit into his mouth and gently sucked on it.
His tongue moved first, trailing lower until he got to her hole and teased her. His ministrations continued for a moment before delving hungrily into her, savoring her taste. This is what he knew, a woman’s moans echoing in his ear, begging for more as they twisted and moved in pleasure, begging for more, not being in love with a blue-eyed angel of the lord. He sucked and licked until he felt her cum from just his tongue. He backed off for a moment to let her recover before bringing his right hand to gently tease her clit while he watched her face. When he saw that she was ready for more, he let his finger fall until it got to her hole and teased her entrance just a bit.
“Are you willing to beg?” Dean asked her.
She nodded furiously. “Please, fuck, I need it. I need your fingers in me. I feel so empty right now.” Dean smirked at her pleas and lowered his head again so he could take her clit in his mouth as his middle finger pushed into her. He gently thrust in and out while curling his finger to hit her G-spot. After a moment, he added another finger and allowed her to adjust. When he felt her loosen up around his fingers, he beckoned Cas over.
Dean grabbed Cas’ hand and lined his palm with the back of the angel’s hand. He curled his fingers so both he and Cas were only holding up their middle fingers. He guided their fingers to Eliza’s entrance and repeated the motions he was doing earlier. Eliza also guided Cas’ head to her clit so he could lick and suck, praising him when he found the right motions that inevitably brought her to another orgasm.
When Eliza settled, Dean carefully withdrew their fingers and helped Eliza up, and instructed Cas to lay back on the bed. Ever so dutifully, Castiel did so and Dean grabbed a condom off the nightstand. Before he could do anything with it, Eliza grabbed it from his hand, took it out of the package, and put it on Cas. She then moved on top of the angel, using her hands to map Castiel’s chest and leaning down to steal a deep kiss. She then moved her hips to grind against Castiel’s cock causing both of them to moan.
It wasn’t long before Eliza grew impatient and moved her hand down to guide Cas’ dick into her entrance. He grunted as she sunk deeper and deeper while Eliza moaned. Dean watched their moves with fascination, the way Cas stretched Eliza open, how her head was thrown back…
A part of a Dean wished he were the one on top of Cas, slowly moving as he took his angel’s virginity, but he wasn’t gay.
Dean’s utter obsession with the way the two came to a forceful halt when Eliza beckoned him over. He knew what she wanted, that extra bit of stimulation to get her over the edge, so he gave it to her. He trailed his hands down her sides before gripping her hips and making sure she kept a steady pace on top of Cas. His mouth found its way next to her ear so he could whisper filth in her ear.
“Such a perfect slut, letting us use you.” Eliza let out a loud moan, potentially waking up anyone who was sleeping in this shithole they call a motel. “Do you like being our plaything?”
“Yes,” She gasped as Dean’s hands kept her pace steady.
“And after this, darling?”
“Never wanna leave,” She managed to choke out. Dean watched Cas’ face and saw that he was nearing his end, so he moved one hand lower and began skillfully rubbing her clit. In less than 30 seconds, both came, so Dean used their moment of recovery to grab another condom and quickly wrap his dick. When Eliza recovered, she rolled over so she was next to Castiel and spread her legs.
“Gonna fuck me now, Dean?”
“God yes,” Dean rasped before kneeling on the bed and grabbing a pillow to put under her hips. He guided his cock to her entrance and sunk in, both of them making their noises of pleasure. At first, he did shallow but powerful thrusts while biting and licking at her collarbone.
He’d always loved the feel of sex, a woman’s softness, the movement of them two, everything. He could feel Cas’ eyes on him, watching his movements, but he just made sure he was angled towards her g-spot and that he wasn’t going too hard. He allowed himself to speed up a little, though he’d long since stopped his biting and sucking. Her moans and mewls encouraged him to keep up exactly as he was doing.
“Gonna- '' He heard her begin to stutter out, “gonna cum. Right-” Her breath hitched as he kissed her neck, “right there.”
He kept his pace, but his lips moved down and took her nipple into her mouth. This was all it took for her back to arch just the right way and clench her walls just right. He managed to give a few more thrusts before his hips stuttered and he came with a grunt. He pulled out of her and took off the condom and tied it, making sure Cas could see him so he could do the same with his before anything continued. He tossed his in the trash and saw that Eliza had sat up.
Briefly, he raised a brow. “Are you gonna want a shower, cuddles and a movie, or a ride to wherever you choose?”
“Movie, sans cuddles, and then the ride.” Dean shrugged and found a shitty motel movie before the three of them crowded the bed, bare as ever. He tried to pay attention to the movie, but his eyes would wander to Cas’ face, committing the intensely focused look to memory. When the end credits rolled, Eliza got up and began putting her clothes on.
“Well, boys, this has been fun, but it’s time for me to go, so let’s get into the car, yeah?” Dean got up and put his clothes on too.
“If you don’t mind,” Castiel hesitated, “I’d like to stay here.”
“Yeah, man,” Dean furrowed his brow, “of course.” Eliza gave him a quick kiss and walked out the door with Dean who quickly waved to him. A part of him knew that his Cas would be gone by the time he returned.
Aside from giving him the address to her place, Eliza waited until they were on the street to start talking again. “You need to tell him.”
Dean focused on the road, not the way his heart pounded. “What?”
“You like that guy. I saw the way you were with him. I felt the way you were with me.”
“Did I do something wrong?”
“On the contrary, you did too much right. ” Eliza looked at him, but his eyes stayed on the road.
“How is that a bad thing?”
“Didn’t say it was. But you can’t say that you weren’t deflecting your attention. Not without lying.” When Dean didn’t respond she continued. “You focused on me so you wouldn’t focus on him in all the ways you think are wrong, but it’s not the ‘60s, you can be gay.”
“I’m not gay.” Dean murmured, hoping she heard it over the harsh beating of his chest.
“I don’t care what you are, you like him.” Dean pulled into her driveway and she got out. “It was a good time.”
Dean watched her go into the house before driving back to the motel room.