A/N: I don't own Supernatural or any of the characters used in this story. Dedicated to my good buddy Amoriandis 3.
"You can't just TRY dick, Robert," Crowley playfully chastised in his gravelly voice. The demon and the hunter had been enjoying clandestine meetings whenever their busy schedules permitted. Things were fiery between them. Filled with lust and passion. Lately, however, Bobby had wanted to try something new. "Come on. What you afraid you gonna hurt me? I can take it."
Bobby sauntered over to Crowley carrying two glasses and a bottle of whiskey. "I'm sure you can, Robert, but IF you can't I'm not sure I'll be able to stop myself. Your willingness does... Things to my dangly bits" Crowley snapped and a bottle of Craig appeared from which he filled his glass.
They sipped their respective liquors in companionable silence for a moment. This conversation wasn't new to either of them, but every time Crowley prevailed. Bobby was more determined than ever, though. They had done everything else. Crowley usually got him too worked up to care who was the top, but his curiosity was getting the best of him.
"Aren't you the least bit curious?" Bobby asked with a sigh, growing exasperated.
"Not in the least, love." Crowley watched his hunter carefully, prepared for almost anything. What he unfortunately wasn't prepared for was the hurt look that flashed across Bobby's face before he could hide it. He'd been denying Bobby this request for months now, never giving any consideration to how that would effect his hirsute lover. He downed the remainder of his drink, then unceremoniously walked over and plopped himself in the hunter's lap. Bobby wrapped his arms around the demon and kissed his neck gingerly.
"Are you sure?" Crowley asked gingerly. He grinded his hips into bobby's lap. "I mean, you could have me instead,"
Bobby groaned under Crowley's ministrations, but held firm. "I want you to… do me." He forced out, blood creeping into his cheeks. Crowley had considered this idea many times, but was scared for Bobby. The first time is never easy, and he wasn't exactly lacking in the groin area. He got up and straddled Bobby. He put his hands on Bobby's face and looked deep into his eyes.
"Ok Robert. You win. But if it's too much, tell me. And if you don't want to go through with it, let me know." Bobby nodded, looking surprised. As much as he wanted it, he wasn't really sure how this was supposed to go. Crowley got up, and allowed his hunter to lead him to the bedroom. "So, how do we go about this?" Bobby asked gruffly, not making eye contact.
"Easy tiger, this isn't the sort of thing you just jump into." Crowley said as he closed the distance between them. It started with a kiss. Deep, sweet, needy and longing. Bobby slipped off Crowley's coat and tie and Crowley undid his lover's flannel. They tumbled onto the bed, undressing each other in earnest now, the need for skin on skin contact growing with each moment The men rubbed up against each other straining for friction and contact, while groping heatedly at each other. They only halted when they were down to their boxers. Bobby was on his back and Crowley was in between his legs.
Crowley paused, taking a moment to look at his lover. Bobby's face was flushed, with a flustered expression on his face. His eyes were filled with desire and something else the demon hadn't seen in someone's eyes for him since he'd been a demon, maybe even longer: Love. Bobby loved him. the thought made him smirk. "What are you grinnin at ya idjit," Bobby groused after a few seconds. "Nothing love," Crowley responded as he slid off Bobby's boxers, removing his own shortly after, leaving the two men, naked in bed together. Crowley took another moment to admire his hunter, and noticed much to his amusement that Bobby was surreptitiously checking him out as well. "Like what you see?" Crowley mocked playfully.
"If I didn't we wouldn't be here." Bobby retorted. with that, Crowley slowly closed the distance between them for a deep kiss. When they came up for air, Bobby reached into his nightstand, and pulled out a small bottle of lubricant, after a moment or two of fumbling around. "Someone's prepared," Crowley mocked, taking the bottle and applying liberal amounts to his fingertip. "Shut up," Bobby responded, watching Crowley and contemplating what he had gotten himself into. Bobby hissed as the first finger pressed slowly into him. "Are you sure you want to continue Robert?" for once there was no mocking or snideness in Crowley's voice, just genuine concern. "Yeah, just keep going" Bobby grunted out, holding his breath. He was trying to welcome the intrusion, but it didn't feel natural, his body was trying to reject and expel the foreign object. Crowley took Bobby's throbbing member in his hand and began to slowly stroke it, starting to move his finger in a matching rhythm. Before long, Bobby had loosened up enough for him to add a second finger. As he did Bobby groaned and squirmed, but didn't protest. Taking that as a sign Bobby was almost ready, he quickened the pace of his ministrations, scissoring his fingers to loosen Bobby up. He knew Bobby was close when he started thrusting into his hand and wantonly gripping the sheets, barely withholding moans of pleasure. He crooked his fingers, and Bobby exploded onto his hand, pleasure plain on his face. Crowley scooped up all Bobby's essence and mixed it with a little lube to slick his member. "Are you ready?" Crowley asked, still apprehensive about the prospect. "As I'll ever be," Bobby responded huskily, still riding the afterglow of his climax. Crowley pushed his slick manhood into Bobby's virgin entrance, relishing every hitch in breathing and moan that issued from his hunter's lips. He stopped once he was in, waiting for Bobby to get used to the feeling, and to brace himself, he had to stay in control, though Bobby was pushing dangerously close to the edge. After Bobby's breathing evened out, he started to rock back and forth slowly, moving just enough to get his lover used to the sensation. Slowly, Crowley began to lengthen his thrusts, using a little more moving out further and going a little deeper. Bobby's cock was slowly coming back to life and Bobby couldn't contain the moans escaping his lips. Inspired by the pleasure he was giving Bobby, he picked up his pace, and in turn Bobby grabbed himself and started to match the demon's rhythm, his excitement causing his already tight entrance to contract around the king of hell at increasingly short intervals. feeling that Bobby was approaching his second orgasm, Crowley Angled his hips to hit the spot he hit before, causing gasps and moans from his hunter, who was now enthralled with all the new sensations. He carefully, but precisely rubbed the spot with each thrust, feeling his own orgasm building. Suddenly, Bobby's hole squeezed tight around Crowley as Bobby hit his second orgasm, causing Crowley to lose control. The demon savagely drove into Bobby's prostate, causing the man to cry out even more and grip the sheets till his knuckles turned white. Crowley came into Bobby, then proceeded to collapse on top of his hirsute hunter. After a few moments, he pulled out and moved to sit on a corner of the bed. "What's wrong?" Bobby asked, utterly confused and dazed from two of the best climaxes he'd ever had. "Just then, at the end, I lost it. I could have hurt you." I almost hurt the only person who loves me the demon thought. "Well I didn't notice. Seems like you did a pretty bang up job to me," Bobby said as he pulled the demon into bed with him. As they lay there in each other's arms Crowley stroked his human partner's beard absentmindedly. "I love you Robert." "I love you too, Crowley"