Catching the Eye of a Mob Boss Ch. 05

I felt his fingers as he drew down the zipper of my pants and put his thumbs in the waist band of my boxers. He pulled both my boxers and my pants down my legs. He stopped dead when my penis was revealed to him. I was hard as a rock and stood at attention in front of him. He looked at my ace as he reached out to stroke my cock. I gasped at the feeling of his warm hands on my throbbing member

"Well it looks like I'm not the only one who is impatient." He smirked at me.

He knelt in front of me and helped me to remove both my shoes and socks, before finally helping me chuck the pants and boxers. It was definitely awkward to step out of clothing when I didn't have the use of my arms or hands for balance. I managed it with the help of Diego.

One we were both fully naked except for the rope still binding me, Diego pulled me towards the bed. He got on the bed first tugging me after him using the rope leash connected to the rope around my chest. It pulled me off balance but I was able to get a knee on the bed before I fell face first into the bed. He kept tugging me towards him causing me to shuffle on my knees across the bed towards him.

"Come straddle me Jace." He murmured as he tugged me. He helped me guide one leg over his body so that I was sitting on his lower stomach. I could feel something poking me from behind which startled me. I jerked forward which set me off balance almost causing me to fall forward. Diego caught me so I was able to look behind me and see that it was Diego's penis that had poked me. I flipped me head forward again to see Diego watching me with humor filled eyes. I felt his hands guide me so that I was laying on his chest, my legs still folded on either side of his hips.

He ran his hands down my back caressing all the skin that was not covered by rope until he reached my ass. He nipped my ears as he took one hand and spread my ass cheeks while using the other to gently rub a finger along my rose bud. I whimpered into his neck at the sensations both his mouth and hands were producing. His nibbles traveled down my ear to my neck, then my shoulder; while his hands became more insistent on my ass.

One hand left my butt and reached for something behind him. I heard a cap snap then felt cold liquid hitting the top of my ass crack and trickling down. I jumped at the feeling but was soothed by a reassuring murmur from Diego. He began rubbing circles with a finger around my anus again. Then slowly pushed with one finger until my anal muscles gave way and allowed for the invasion. I whimpered again at the feeling rubbing my face into his neck restlessly.

He started pumping his finger in and out of my ass. I shifted, not sure if I wanted to get away or push further onto his finger. He chuckled at my movements and added a second finger to my ass, stretching me open with that scissoring motion again. I moaned.

His fingers felt good; too good. My mouth moved across his neck needing to do something. I settled on sucking his skin. He groaned at the feeling of my lips on his neck. He sped up his fingers. I couldn't help it. I started moving my hips in time with the thrusts of his fingers. He added three fingers stretching me even more. It definitely stung. I was feeling very full and he hadn't even slid his dick inside me.

"I can't wait anymore I need to be inside you." He groaned out. He reached for something (probably the lube), I heard the cap pop, and the sound of him rubbing it onto his dick. More lube was poured onto my ass. One of his hands came up and helped me to sit up. He guided his dick towards my hole until I was positioned just so. He helped me lower myself until his dick was pressing against my anus. He pulled my hips down just as he thrust up. I felt my muscles pop as the head and half his dick was thrust into me all at once. I cried out in pain at the invasion. He groaned in agreement. Gravity helped his dick slide further into me before I was fully ready. My hole kept slowly opening up until I was fully seated on his dick and panting. Tears trickled down my cheeks Diego reached up and gently wiped them away.

"We will wait until you're ready love." He murmured as he reached down and began to gently stroke my cock with his clever fingers. It felt so good, and helped rejuvenate my partially flaccid cock to full hardness. My body started to relax and adjust into the feeling. I could feel him bumping against my prostate.

The combination of feeling full, the stimulation against my prostate, and Diego's hands, was driving me insane. I needed to move. My hips shifted, causing Diego's hands to tighten on my dick before going back to stroking. I moaned and moved again; rotating my hips in a circular motion. Diego gasped and grabbed my hips. He didn't stop me just held on tight.

The movements felt good but they weren't enough. Maybe if I moved my hips up and down that would get the friction I was craving. I slowly lifted my hips up, then let gravity lower me back down. Yessssssss that's what I wanted. I groaned in satisfaction. Diego echoed my groan with one of his own. His fingers dug into my hip bones to the point of bruising but I didn't mind. It showed that I wasn't the only one who was affected. I lifted up again and sat down a little harder.

"Yea, just like that baby." Growled Diego. On my next up down motion he helped guide me, encouraging me to go faster and harder. I was happy to oblige, it felt too good to stop now.

I started the fastest rhythm I could manage without the leverage of my hands, but it turned out to not be fast enough for Diego. He eventually got tired of letting me set the pace. He grabbed my hips in a firmer grip and began to pound into me. I yelped at the new pace he was setting. My dick bounced against my stomach as he pumped into me. I was just as active a participant fucking him hard.

The pace we set was brutal and within five minutes we were both soaked in sweat. I felt my orgasm boiling fast to the surface, but I needed some stimulation on my dick to send my flying. Diego must have read my mind because he was able to remove one hand from my hip to grab my penis and pump it in time with our thrusts.

His movements were jerky, but it was enough to send me over the edge. I came screaming his name. He came seconds after me, shooting his cum into me. I collapsed on his chest, all the strength having left my body.

His left hand still held my softening dick, while his right rested against my hip. I was breathing hard into his shoulder while I felt his breathing start to slow.

"Don't go to sleep on me now. This evening isn't over just yet." He murmured into my ear.