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Greg hadn't expected to be as into James in drag as he was. There was something about his face that just came alive when he dressed up for him. Greg hadn't even told him to. James had just done it, had turned up one night all glammed up in a black sequinned dress, some killer make-up, and a silly little tiara, and fucking hell, those heels were ridiculous, and Greg just didn't really know what to do with any of that except that he wanted him.
And perhaps that would have been fine on its own, but James had come prepared with a plan. That plan involved a whole box of little mini pastries and a request for Greg to feed him while he knelt at his feet and sucked his fingers afterwards. How the fuck James knew he'd be into that, he didn't dare guess, but fuck, that was just what he needed.
Greg led him over to the sofa, and James knelt before him in perfect submission as he offered the box of pastries to him. The way James was just looking up at him with eyes full of adoring love, fuck, that was hot. And then he opened his mouth, "Please, sir, feed me, sir," and just rested a hand on Greg's thigh, and Greg wasn't sure he wanted this to end. He was already hard. He wanted that obscene mouth around his cock by the end of all of this. Fuck.
Perhaps James had intended for Greg to just feed him the pastries, but that's not what Greg did. Like he was going to let James just eat an entire box of them without getting any himself. So he ate one, and God, the look of such abject longing in that boy's - girl's? - face, Jesus Christ.
"Do you really think I'm just going to feed you without you having done anything to earn it, James? These are seriously good. I expect some fucking work, you hear?" Greg said.
James let out a whine, as if he hadn't actually counted on Greg making him work for them. "What kind of work, sir?"
"Well, if you're going to dress up for me like that, you'd better show off for me, hadn't you, you slut," Greg said.
James might have bit his lip. Might have. He wasn't very good at this sort of thing, but he'd chosen that specific dress because it did make him feel sexy and special. He'd put a lot of work into this, and had practiced being sexy in a way that felt natural to him, and wasn't just overdone porn moves. This had required practicing with Ed for probably longer than necesary, but Ed hardly complained, and James had loved being able to just tease him and enjoy how his hands ran up his hips, begging to lift up that dress, before James swatted them away.
But that was practice. This was real. He offered a coy look, and sat back, running a hand down his chest. Her chest. He didn't always switch gender in his head when he wore dresses, but he could feel it happening then. He wasn't going to seduce Greg. She was.
It helped, if she was honest. She filled that dress completely now, and moved her hips gently as she sat up and placed her hands on his thighs, teasing him with what she knew he really wanted, but she wasn't going to give that to him until he was ready. It's not like she couldn't see the bulge in his trousers, after all.
She might have crawled up into his lap like a snake, and kissed him, her hands beginning to stroke his neck and shoulders. Greg held her tight and kissed her back, teasing her and making her shiver. She leaned in to whisper in his ear, clutching onto him. And if her hand slid down his chest and rubbed his groin, well. That was part of the fun, wasn't it?
"Feed me, sir, please, I'm starving."
"Then you'd better get on your fucking knees, hadn't you?" Greg growled back, and she gasped at his hand feeling her out, seeing how aroused she was.
"Yes, sir," she breathed.
She might have taken her time, kissing down his body and making a point of kissing his bulge, which really just resulted in him growing impatient and pushing her down himself. She knelt beautifully, sitting on her heels, begging up at him with her chest pushed out, her expression all puppy dog eyes and wet lips.
"Please, sir, feed me," James breathed.
Greg smiled at him, and might have eaten another one, just to see how wanton he looked now, and how his lipstick was smeared, making it look like he had just been sucking his cock. Fuck. He reached down to lift his chin with his fingers, and James' mouth opened, taking in his thumb when offered, keeping constant eye contact with him as he did so.
James might have taken his hand then and started sucking his fingers, gently, softly, always focusing his gaze on him, watching his face. James hadn't expected to enjoy sucking his fingers as much as he did. They were so big in his mouth, but he didn't care. The more he sucked them, the more little adorable noises Greg made.
James almost whined again when Greg pulled his hand away, but he didn't, because Greg took one of the pastries and offered it to him on his hand. This one had icing sugar and cream, and James ate it delicately, bite by bite, refusing to use his hands to help him. And then he licked Greg's hands clean in such a delicate way, Greg actually gasped.
When he was done, he gazed up at Greg, and asked for another one. "Please, sir, feed me."
James leaned into his hand as he cupped his face. He loved the way Greg touched him. And then there was another pastry, this one a little tiny chocolate eclair, and James enjoyed licking the chocolate off his hands a lot more than he'd anticipated.
James hadn't expected to be this turned on by it, and his cock was aching for release. But Greg was in no hurry, and made him eat the entire box, save for a handful he ate himself, before he even thought about letting him anywhere near his cock. James may have placed his head in his lap, begging quietly, feeling how aroused Greg was, needing to finish this off.
And Greg, dammit, was just stroking his fingers through his hair, and praising him for being such a slutty little girl. Perhaps there was more finger sucking, too as James cleaned his hands and adored those fingers and savoured how that contrast of sweet and sweat tasted together on his tongue.
Greg kept him waiting. He was enjoying this too much. The sight of James just lying there in his lap, his face turned away from him, and his body draped in that shimmering dress, God. For a moment, he didn't know if it was a man or a woman kneeling at his feet, and he didn't even care. James was such a pretty girl, and such a pretty boy, and Greg would be fine with either. He wanted them both.
Greg might have let out quite a shout as he finally let James go down on him, and that girl sucked his cock with all the same intensity with which she'd sucked his fingers. He grasped her hair, dislodged the tiara a bit, didn't really care, just cared about that hot wet mouth that was all of a sudden clamping down on him as he came.
James, the fucker, didn't even move. He just kept licking. That mop of hair was still firmly in his lap, and Greg didn't want her to go.
"I want you to fuck me wearing that dress," Greg said, breaking the silence.
James' eyes went wide as he turned to look up at him. "Oh, sir, oh, I don't-"
"Do you want to come or not? Because I could just send you home right now," Greg said.
James very much did want to come. He wanted to come very much indeed. "Yes, sir, I'll fuck you, sir."
Greg stroked her cheek. "Good girl."
James thought this would be more difficult than it turned out to be. Greg knew what position worked best, and helped James prep, and then, James was pushing inside him, leaning over him, able to watch his face as he began to fuck him, and his cock was just so, so fucking happy.
Greg grasped his head roughly and growled in his ear. "Go on, fuck me up, you slut. I can take it."
That command did very arousing things to James, and he started thrusting harder, pinning his shoulders down. Rough sex wasn't really his thing, but he kind of knew what to do. Which would have been fine if he hadn't been so close to coming, because almost as soon as he'd started, he'd come hard, and fuck, nothing had ever felt like that before.
James fell on top of him afterwards, clutching him tight, and he didn't care that his tiara was now clinging to his hair by a very tangled strand of thread. Greg kissed him, and set that tiara back where it should be.
"Fuck. I didn't think you'd be that into drag, Greg, seriously," James breathed, just letting everything overwhelm him.
"How could I not be when you're that fucking hot, you minx," Greg said, playfully swatting his butt. "I hope I get to see her again. Fuck you look so hot kneeling like that. Fuck. Fuck. The way you eat is obscene, Jesus Christ."
James smiled. "You might see her again, if you play your cards right."