The Underbosses Psychiatrist (M/M)

29 - Chapter Twenty-Nine - Zev Martin's Point Of View.

Jackson paused and moved away from my member as he kissed his way up my body. He stopped at my neck and planted a few kisses each one lasting longer than the last. He kissed the same spot a few times before I felt his teeth bite my shoulder. It was both painful and pleasurable. I was defiantly going to have a fucking set of bruised teeth marks. That was going to be pretty interesting to explain. Fucking Jackson.

"Jackson. That's not nice."

"Looks pretty nice to me."

"I'm sure it does."

Jackson pulled away and kissed my lips deeply. Jackson went back to taking his time kissing spots on my body that I was sure no one else had. It felt like he was leaving his very soul lingering on each kiss. This moment was pure bliss. I could have just stayed this way forever. 

"Are you ok to continue? you seem out of it."

"I was just thinking, I'm good to continue."

Jackson got off the bed and went to the dresser. He opened the top drawer and pulled out the lube. This was amusing to me because all the times I had gone into the drawer to grab socks and boxers for him I had never found that lube. He closed the drawer and walked back to the bed. I took that moment to really look ever his figure again. I was slightly envious that he could maintain the lifestyle he had. I hated his lifestyle, It was dry to me. The sound of the lube being popped open and squeezed out made me suddenly nervous. I really didn't know why though.

Looking at Jackson I watched him slick up his member. He had a five o'clock shadow going on and it was a good look for him. I rolled over and stuck my ass up in the air. The feeling of cold lube being wiped over my hole made me shiver. Even though it had been in his hands for a solid bit it was still frosty. He slipped his first finger inside me. I groaned into the mattress. The second finger was welcomed and shortly after that, a third finger was added. His fingers felt really good inside me, but I wanted something more filling. Jackson pulled out his fingers and whined. I knew what was coming but I still didn't like feeling this empty suddenly.

"Are you ready?"

"Absolutely."

I felt Jackson get closer to me and I bit my lip as I felt him slip his member between my crack and thrust back and forth a few times before he positioned himself at my hole.  I have a light push and I felt him start to slip in.

"Fuck. You're super tight."

"Trust me. I know" I said groaning and grinding my teeth. He was thrusting slowly in and out, and getting deeper and deeper. He paused as soon as he was all the way inside me. This gave me a really good moment to adjust to the size of his member. Grinding my teeth again the pain was slowly subsiding. Jackson was waiting for me to give him the go-ahead to start moving. I had the give the guy props he was extremely patient.

"Alright. You can move now."

Jackson moved slowly. His hand on my lower back. His hand was warm and comforting on my back. Stretching out my arms my back popped, it felt amazing. At that same time, Jackson started to thrust faster and deeper. My head was laid on the mattress well Jackson picked up his pace and slightly changed our position. I became pretty aware of the weight and size of Jackson as he dropped some of his weight on me.  His member was really filling as he shoved himself in and out of me at a very aggressive pace. I really didn't hate the pace he was going at. The sound of our flesh slapping together was the only thing you could hear besides the deep breaths coming out of both of us. He stopped thrusting and ground his hips against my ass and a moan came out of me and despite my best efforts to make it a quiet sound it was not.

Before I could recover my ego, Jackson wrapped his arm under me and around my chest. He pulled me upright and back. His thrusts became aggressive and deep again as he bent me and used me to his advantage. I bit my lip as his free hand came around and palmed my member. Soft whimpers fell from my lips, his hand sloppily jacked me off and he thundered inside of me. I felt my orgasm coming hard but I couldn't make the words I wanted.

I felt my orgasm hit and I closed my eyes tightly panting. Jackson didn't stop his movements on my member or my hole.  My entire body shook and shuttered. Whimpers were coming out of me and there wasn't anything I could do to stop it. Jackson brought his dirty hand to his mouth and licked the mess I created.  It was shocking to me.

"You taste great."