Monsterous Trust (Ticci Toby x Eyeless Jack)

Free Time

The time was perfect, it was the night before a weekend and just about everyone was going to be gone tonight, including all our neighbors in the nearby rooms, we were basically home alone, I was sitting on the bed quietly waiting for Toby, he was in the bathroom finishing up with his shower, I was already clean and was drying off my hair, I heard the door open and I looked over at Toby.
"Are you sure you want t-to do this?" He asked, "Morning's a long ways away."
"We don't have to go until morning." I said, "What I meant is go until we can't."
"I don't want you t-to pass out." He said.
"We can call it at any point." I said, "I have plenty of stamina, I won't pass out easily."
He sighed as he continued drying his hair, he began coming over to me, I moved slightly so he could sit on the bed with me, he was being really quiet, I looked at him slightly.
"Are you-"
"We don't have to go more than once if you really don't want to." I cut him off, "I'm willing to do anything at this point."
He was quiet.
"Once is fine with me." I said, "And if we go longer then we go longer."
He sighed as he looked at me slightly, I gently kissed his cheek and he smiled slightly.
"Okay, you win." He said.
We both wrapped our arms around each other and began making out, he gently began pushing me back onto the bed, I wrapped my legs around him and he grabbed my thighs, he eventually moved away from the kiss and started kissing my neck, I let out a small whine, he finally moved away from me and moved over to the nightstand, I sat up slightly and watched as he opened a drawer and began going through it, I just quietly watched as he dug through it, soon he pulled out the tube of lube, he set it on top of the nightstand and reached back in, I had no idea what he was trying to find now, probably the gloves and gag, he pulled out the gloves and set them down before he reached back in, he then pulled out a condom, that was kind of comforting knowing he was trying not to get me pregnant, he set the condom down and grabbed the lube, I leaned back and watched silently as he opened it and coated his fingers.
"What about the gloves?" I asked.
"Roll over." He replied quickly.
I didn't bother arguing with him and just started rolling over, lifting my hips up for him, I felt him gently pushed against me and I gripped the pillow tightly, I held my breath as he pushed his fingers all the way in, he started with two as well, I bit the pillow as he slowly thrusted them, he scissored them and a moaned escaped from my throat, he continued thrusting as my legs shook, soon he pulled his fingers out slightly only to push them back in with another, I arched my back slightly, it wasn't as bad as before, I bit harder as he wiggled them around, I gasped when he pushed into my prostate, he pushed into it harder and I groaned, he pulled his fingers out and I started gently breathing, I could tell he was reposistioning himself, I felt him push against me and I instinctively pushed back, getting him to easily slide in, he gently gripped my hips as I started shaking, he let me adjust and I took deep breaths, he started gently kissing the back of my neck in a way to calm me down, after a while he began slowly moving, I couldn't help but groan, he slowly picked up the pace and I bit harder, he continued kissing my back and neck as he moved, I somewhat repositioned myself and gasped as he pushed back in, I moaned as he grinded against my prostate, I dug my nails in deeper in the pillow as I hid my face, I was beginning to shake more, he began moving away from me slightly but kept his hands on my hips, slowly pulling me back with him until I was basically sitting on his lap, he continued moving and it gave me a completely different feeling, I groaned as I hid my face in the pillow, biting down on it as he picked up the pace again, I tried my hardest to hold back noises and my orgasm, it was too early for that, he pushed my face into the bed more as he started changing our position again, he slowly flipped me over so I was laying on my back.
"G-gloves..." I stuttered out as best as I could.
He sighed before he reached over and grabbed the gloves, he helped me put them on before he leaned down and gently kissed me, I sighed as I leaned my head back, he started moving again and I held on tightly to his back, he made one sharp movement and I immediately groaned out an orgasm, I sat there panting as he let me recover, my mouth was hanging open as I tried to take in oxygen, he was kissing my face and neck as I relaxed, once I calmed down enough he began moving again, I wrapped my legs around him as he picked up the pace, I slowly became more and more audible, my grip around his waist getting tighter the more he moved, I leaned my head back as I shifted so he'd start pushing against my prostate again, I groaned as he moved, he shut me up by pressing his lips against mine, I somewhat grabbed his head as I deepened the kiss, I accidentally pulled his hair but he didn't seem to care, I remembered that he couldn't feel pain so I just said fuck it.
I decided to get more rough with him, moving my hips as I gripped his head and squeezed his arm, he seemed to pick up on the fact that I wanted it rougher seeing as how his movements changed to my demands, they became sharper and harder, his hand slowly moved from my hip to my member, I grinded my hips into his hand as I moaned into the kiss, he finally pulled away from the kiss and I began breathing, he started kissing my shoulder and I bit his in return, he barely reacted to it, he started biting my shoulder back and I moaned loudly, I threw my head back as I came, Toby obviously rode out his orgasm but he was wearing the condom, I sat there breathing as he was sitting over me, looking down at me.
"Maybe... we will go longer." He said.