Yeah," Draco smiled, "I'll help you."
Draco explained that they would need a lubricant of some kind and that he would need to be prepared for penetration. Harry looked so hopelessly adorable as Draco explained this, blushing every time Draco said "penis" or "arsehole" or even "finger."
Harry was suddenly holding a tube of lubricant and Draco looked at him questioningly. Harry shook his head and said, "I know a lot about magic. If I need something, I can get it somehow." Draco laughed at him, feeling more at ease than he had since he was a small child, which was ironic, since one of the most powerful and dangerous wizards in the world was about to prepare his virgin arsehole for anal intercourse.
Harry squeezed a liberal amount of lubricant onto his fingers and, blushing, inserted one digit into Draco. It seemed to go in easily, so Harry inserted a second, to which Draco let out a sharp hiss. "Sorry!" Harry said, concerned, but Draco shook his head and said it was fine; he just needed to get used to it.
Harry pumped two fingers in and out of Draco, scissoring the way Draco had told him to, until Draco said he thought he was ready for the third. The third finger was painful, too, but soon Draco felt ready.
"This is going to hurt more than the fingers did," Draco explained to Harry. "But I want to get past the pain. I want to do this."
Harry nodded and removed his fingers from Draco's arsehole, squeezing more lubricant onto his hand and coating his cock liberally with it. "Ready?" he asked, and Draco nodded.
Harry tried to position his cock at Draco's entrance, but the way they were positioned, with Draco's knees bent slightly and his feet flat against the mattress, made penetration seem unlikely. "I, erm…" Harry started, "I'm going to need your legs back." Draco nodded and pulled his legs up towards him, exposing himself further to Harry.
Harry pulled Draco's legs up and hooked them around his shoulders, then positioned himself, beginning to push in slowly. Draco screwed his eyes shut, willing himself to relax, to allow Harry to enter him.
"Are you all right?" Harry asked, concern evident in his voice.
"Yeah," Draco huffed. "Just get past that point and I don't think it will hurt as much any more."
Harry took that to mean "get through quickly" and forced himself about halfway in. Draco cried out in pain, but reached his hand out to keep Harry from pulling back.
"Just give me a minute," he said, trying to relax and to remember that this was what he needed to happen right now. It took a moment, but Draco finally opened his eyes and said, "Okay. Keep going."
Harry moved slowly, trying to help Draco accommodate his length little by little rather than doing too much at once, which Draco appreciated. When Harry was sheathed completely he stayed very still, his arms shaking from holding himself up.
"Come here," Draco said, pulling Harry down so that he was resting on top of him. "You can move now."
Harry pulled out a bit and took in a sharp breath. "Merlin," he said, "I've never felt anything like this before."
Draco let out a soft chuckle and lay back as Harry took control, pulling partway out and rocking back in slowly. After a little while, the pain had subsided a bit and was starting to be replaced by an altogether different sensation. Soon Draco was meeting Harry's gentle thrusts, coaxing Harry to move just a little bit faster. His erection, which had died away during the painful parts, had come back full force, brought to life by the not entirely unpleasant feeling of Harry moving within him and the delicious effect the friction from their moving bodies had had on his cock.
"Harry," Draco whispered, growing to love the way he felt inside him.
"So good," Harry said, kissing Draco.
Soon Harry was pulling out farther and thrusting in harder and Draco invited him back in wantonly every time. Harry's accuracy had gotten good, hitting Draco's prostate more times than not, sending little sparks of pleasure throughout his body. But the most overwhelming sensation for Draco was Harry's magic, erratic and crackling, coating his body with sharp tingles of lightning, pulling Draco closer and closer to the edge.
They were a sweaty mess, thrusting and writhing and calling out to every deity they knew. Draco felt Harry's magic cresting and lost it, crying out his lover's name and coating their bellies with his come. His orgasm seemed heightened and prolonged by Harry's magic, which burst around him a moment later as Harry came, grunting and thrusting feebly, emptying himself into Draco.
When Harry was spent, he pulled out of Draco gently and moved to his side. Draco winced as he lowered his legs, which had cramped. Harry laughed at him and Draco asked what was wrong.
"You're making a funny face."
"It's all… coming out," Draco said.
"That probably is a bit uncomfortable," Harry agreed.