Authors note; Don't judge. … This is only my second one after all.

Claude had finally worked up the guts to go visit the Phantomhive Manor late one night. He crept like a spider into Sebastian's room, and waited silently for the other to walk in. Once Sebastian did walk in, he would be caught in Claude's devious spider webs. These webs were carefully placed, and lay out. Tap. Tap. Tap. Tap. Claude could hear Sebastian coming down to his room, so he situated himself in a corner where Sebastian could not see him. It was too dark anyways. Sebastian opened the door, completely un-aware of the spider demons presence. Without a warning, something sharp cut into his wrist, sending blood onto the floor.
Michaelis, getting caught in such a simple trap?" Claude's voice had a small hint of danger in it, while Sebastian's had fear. Claude was known to be a pervert.
"I don't have anything to say to you, besides a question. What are you doing?"
Claude spoke too soon. "I was ordered to humiliate you. I figured, penetrating that tight hole of yours would work." A devilish smirk appeared on the once emotionless butlers face.
Sebastian emitted a hiss, and sighed. "Pervert.."
Sebastian didn't dare move. He couldn't risk any more injures. Ciel and he were to go places tomorrow, and he did not need this.
With a flick of Claude's wrist, Sebastian's clothing were torn to shreds. "You have such a perfect body.."
Claude's voice this time was full of lust. Sebastian closed his eyes, dreading the following moments. Claude moved closer to the raven, paying attention to his own webs. A single gloved finger stroked across the naked chest, causing the other to shiver.
"Say, have you ever had someone go down there..?" Claude questioned, clearly seeing the tense and stress on the others body.
"Even if I hadn't, I would never admit that you were my first."
Claude smirked, and chuckled. He was going to Sebastian's first. That made him feel more powerful somehow.
"I will enjoy you greatly, Sebastian."
Sebastian shivered at the thought, but didn't fight back when Claude unzipped his pants and walked behind him. Once he felt something hard near his entrance, he froze and stopped breathing.
"Mhh.. Something wrong dear raven?" Claude noticed how his chest no longer moved, and gave a teasing buck of the hips, causing about half of his tip to go in. That was enough for him to emit a light groan.
"Not at all.. just get it over with, damned spider." Sebastian was very scared, to be honest. He was not sure how much pain this would inflict, nor how much he would regret it. Without further words, Claude plunged in all the way, allowing Sebastian no time to adjust. Groans and growls soon emitted from Claude's throat as he made shallow thrusts. It was so tight, it had to be his first time. On the other hand, Sebastian bit on his lips and held back screams. It felt horrible at first, seeing as he was not used to it. Slowly, the small amounts of pleasure took over the pain.
"S-slow down Claude… it hurts.." Claude really was showing no mercy. Instead of slowing down, he simply sped up. This caused Sebastian to writhe, and finally let out a scream of pain. Claude brought a single hand to wrap around Sebastian's phallus, squeezing the base of it as hard as he could to keep Sebastian from releasing. Claude was older, so he knew how to control such things more than Sebastian did.
"Claude!" Sebastian screamed, the pain becoming too much. He needed to release, though Claude was far from done. Claude found the bundle of nerves that drove Sebastian insane, and kept ramming into the same spot. Sebastian's eyes glossed over with almost tears, along with no more sounds being emitted. Claude had made him reach his limit, and he was tired. Slowly, he actually started to fall asleep to recover what Claude had done. Claude would not allow that. He squeezed the base of Sebastian harder, rammed inside of him one more time and stopped moving all together. With his hips staying still, Sebastian was able to feel how deep he really got. This caused him to tighten up all around Claude, and Claude moaned loudly.
"Sebastian, keep it tight like that. If you do, I will let you release sooner." Claude immediately started thrusting again, though his pace was slow. The tightness around him made it harder to move, and he made more contact with the walls of Sebastian's insides. All of this was driving him closer to the edge he wanted. With one last intense ram into Sebastian, Claude released with a prolonged groan. At the same time, he released his grip on Sebastian who in turn released as well. Sebastian made no noises, only small whimpers. It had been too much for his body.
"Sebastian?" Claude question softly as he pulled out, zipping his pants back up. He let loose the spider webs, and glanced at the male who collapsed to the floor. He was sleeping.. Claude suddenly felt bad, and sat on Sebastian's bed, waiting for him to wake.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
Sun shone through the window, awaking Sebastian. When he woke, he was completely naked and his bottom was extremely sore. He glanced at his bed, only to find Claude staring at him. This made Sebastian scoot to a corner, a terrified look in his eyes.
"Did it really hurt that bad…?" Claude's eyes on the other hand had nothing but worry in them.
"Why didn't you just leave after what you did to me?"
"Because I…. I felt guilty about it Sebastian." Sebastian's mouth formed a small 'o' shape at the statement, and sighed.
"You can go now. I'm fine. Nothing hurts." Sebastian was clearly lying, for his 'tight hole' hurt a lot.
"Doesn't your bottom hurt? I did sort of go rough on you.." Sebastian quickly shook his head. He just wanted Claude gone.
"Shut up, and go. You have done enough to hurt me already. I don't need anything else." Claude nodded, and leaped out the window without another word. Sorrow showed in his eyes briefly before he left. Though, he would never forget that day.
The day he gained real feelings for Sebastian.