Catching the Eye of a Mob Boss Ch. 03

"Just leaving my mark love." He breathed then trailed his lips back to the center of my body and down towards my groin. I tensed under him, dreading what I knew was coming. But instead of having my boxers ripped off my body, a hand came up and began rubbing along my still soft dick. It felt good, that soothing rub, not sexual exactly, more sensual I began to relax back into the bed enjoying the feel of that gentle rub and trailing lips.

"That's it just enjoy the feeling." He said as the rubs became more pointed toward defining my girth and size. I could feel myself growing a little hard at the stimulation. Then harder still as he rubbed the head of my penis through the thin material or my dark green boxers. It was like he knew the exact way to touch me to get me turned on, which he probably did. He had a lot more experience than I did.

It wasn't long before I was fully hard from his expert massaging. That's when he slide both hands into the waist band of my boxers and began to lower them. He pulled until my 6 inch cock popped free and stood at attention against my stomach. I clenched my eyes shut hard and tucked my head against my arm. I did not want to see him staring at my hard dick. I wish my dick wasn't hard at all but it was impossible not to be with my lack of experience and his incredible skill.

"Beautiful" he breathed and the next thing I felt was him wrapping his hand around the base of my cock and pumping up it slowly once. I sucked in my breath sharply with my nose. It felt amazing having another person's hand wrapped around my penis other than my own. And the way he pumped it so slowly. My eyes flew open and my head jerked up when I felt something hot and wet engulf the head. It was his mouth I could see it wrapped around my cock.

I groaned and flung my head back down and thrust my hips up, sending my dick farther into his mouth to get more of that amazing feeling. He chuckled and then obliged by pumping his hand on the lower half of my cock while he bobbed his head up and down on the top half. It felt so good. I couldn't help but thrust my hips in time with the movement of his mouth and hand. At this rate I was going to cum fast and hard into his mouth. I was getting really close when there was a popping sound and he pulled his mouth off of my dick. I whimpered in disappointment

"ah ah ah ah you don't get to cum just yet. Patience Jace." He said almost teasingly. "Now let's get you into a better position for the next part of this evening." With that he got off the bed and reached for my left ankle. He detached the cuff from the chain and lifted my leg up towards the head of the bed. Bending my left side in half. He connected the cuff to a chain that held ne in that position, he then did the same with my other leg. He followed this up be putting a pillow under my butt making me feel even more exposed then I already was. I knew what was coming and was not excited about this at all. Frankly I was terrified. I started to shake all over from both the strain of the position as well as from how scared I was.

"I promise you will enjoy being fucked in the ass tonight" he said as he began to massage my ass with his hands. I had to admit even if it was just to myself his hands felt good on my butt, and the bit of hardness I had lost from the change in the position, I gained back from just him massaging me. But I tensed up again as his hands moved closer towards my anus. I really didn't want anyone invading my hole. He circled it with his thumb and his other hand returned to wanking my cock, which was slick with spit from him sucking it. The combination felt incredible. I couldn't help it and groaned with pleasure.

That same chuckle came again as he watched my face while he stroked me and rubbed my hole. He then lifted his hand to his mouth and sucked the thumb that had been playing around my hole. He returned it back to my hole and began to push, it popped past my ring of muscles into my hole and I yelped from the shock of pain. He left it sitting there as he continued to jerk me off with his other hand. He bent his head and began to suck me off again, distracting me from the thumb in my butt. As he sucked me I began to feel the thumb start to pump in and out. I was expecting pain but instead it felt...good. Better than good it felt great.

I moaned unable to help myself. I felt the thumb being pulled out followed by a different finger being inserted, this one went deeper than the other; it felt just as good if not better. That finger wiggled around more than pumped like it was looking for something. It found what it was looking for when I felt pulsing pleasure zoom through me from ass all the way to the top of my head. It caused me to make a sound between a squeak and a groan. A decidedly not manly sound. He popped off of my dick when I squeak groaned and looked up at me with a smile.

"That's your prostate. A favorite spot on a man's body for me, they are fun to play with don't you think?" he said as he wiggled his finger against causing me to throw back my head, thrust more into his touch with my hips and groan.

"I see you like it too." He commented as he added a second finger inside my ass and continued to play with my prostate. My hips spasmed under the stimulation of his fingers. He removed his fingers and I heard him reach for something then the pop of a cap. I looked up to see him put some glistening liquid onto his fingers.

"Just lube" he responded to my look of confusion. "It will make this entire process easier on both of us." He then inserted the now slick fingers into my ass, and it felt ten times better than it had before, they glided and stretched me open in an oddly pleasant way. I liked the feeling of it, which again was fucking with my head.

He started doing a scissoring motion with the two fingers inside of me, it helped stretch me open for the invasion of his finger. He popped his fingers out and applied more lube to three fingers this time and inserted tem. I felt so full and a little uncomfortable with three fingers inside of me, but he kept rubbing them against my prostate keeping me hard and enjoying his touch.

"Good boy, my fingers are gliding so easily, I think it's time we move this process along, I can't wait to be inside of you." He murmured to me as he pulled his fingers out of my quivering hole. My panic button was hit again as he said that. It hit me again that I was losing/ had lost my virginity to this man. I began thrashing once more, shaking my head desperately, though I irritatingly remained hard. The tears that had stopped flowing started up again.

"Shhhh baby, remember I promised you were going to enjoy being fucked in the ass. I am going to make this so good for you." He cooed to me, as he reached up to rub my cheek in a soothing gesture. It's not that I didn't believe him, I just wanted it to be my choice whether I got fucked in the ass at all.

"I thought about giving you the choice of whether we did this face to face or not, but decided that I want to watch your face while I fuck you. I want to watch you as you feel all of what I can give you. The pain and the pleasure of having your ass penetrated and then fucked by me." He said as he shrugged out of his own dress shirt, tossing it the side, exposing his bare chest to my gaze.

He was gorgeous, rippling muscles moved under lightly tanned skin. It was obvious he worked out, but not for show; probably for a sport of some sort like boxing. He had some scars but nothing that really stood out. His arms flexed with ropes of muscles, the exact one he had used to immobilize me and get me into this position. There was a light dusting of dark hairs that matched his head across his pectoral muscles, followed by a snail trail that led down teasingly to the top of his pants. Right where his belt buckle sat.

He watched me as he slowly undid his belt, and pulled it from his dress pants. His mouth quirked as he watched me watching him oh so slowly undue the button at the top of his pants and pull the zipped down on his pants, one teasing teeth at a time. I was excited, and aroused to see what kind of cock this man had. Again what the fuck is wrong with me. I'm being turned on by a strip tease by this man. A man that has me chained to a bed against my will.

I was expecting him to get off the bed and strip completely instead he just pushed both his pants and boxers down his hips enough for his cock to spring fee. And what a cock he had, it was think and long, I'm not a good judge of length because this is only the second dick I have seen in person (the first being my own), but he looked big, way too big to fit inside of me. He was circumcised with a defined head and pronounced veins all along it.

He reached for the lube and popped the cap squirting some onto his rock hard dick. I gulped, my fear of being split in half by his cock looking like a real possibility. He stroked his cock slicking up his hard length, preparing it. He put more lube on his fingers and pushed them inside my now very tense body.

"Relax. It will be easier on both of us if you do." He said as he started up that scissors motion with three fingers. I hated that his fingers inside of me were feeling better and better, and the discomfort was becoming less and less. He kept up this motion until I was gasping with pleasure and trying to flex up into his touch.

"You're as ready as I can make you, and I can't wait any longer. I need to be inside of you now. Remember to relax Jace." With those parting words, he pulled his fingers out, lined up his cock with one hand, held my hips with the other and started to push

I tried to relax, I really did. But I was too scared and it hurt too much. A foreign object was invading my sphincter and I was not happy about this process at all. The pressure didn't let up though, it just kept coming. My sphincter finally gave up the fight and allowed him entrance into my most taboo place. It hurt.

I cried out from the pain and more tears fell from my eyes. I shook my head back and forth, and would have tried to buck him off if his hands hadn't held my hips fast. I was expecting for my cock to deflate under all this pressure, but it stayed rock hard throughout the entire process making me feel slightly sick at my warped body reactions. Luckily he stopped moving and let my adjust to his girth.

"That's it, you're doing great baby. The hard part is over with. Keep trying to relax for me. That's a good boy" He murmured to me as he bent down towards me. He started leaving those butterfly kisses on my face, and licking up my tears with his tongue. He gave me another minute to adjust then started moving again, pushing more of his length inside of me. It definitely still hurt but not as bad as before.

Then he hit my prostate, now that felt good, which helped ease the pain even more. He pushed steadily until he was fully seated inside of me, and I could feel the coarse brush of his pubic hairs against my butt.

"You feel so good Jace, wrapped around me like that with your tight ass, can you feel my pulsing inside of you?" he whispered into my ear. "You feel so amazing I need to move now. I need to feel you drawing me in." And he did just that. He started pumping oh so slowly in and out, short strokes at first but they steadily got longer and more forceful.

I was surprised as the pain receded more and more until it was practically gone but the pleasure increased, and not just in small increments but in leaps and bounds. The more he thrusted the more I didn't want him to ever stop, it felt that good. I moaned in pleasure. I couldn't help it, form the glorious feeling in my ass to feeling my cock rub against his stomach or mine which each thrust, there was no way I could remain quiet.

He chuckled and levered himself up a little so he could see my face while he increased the speed of his thrusts.

"Oh god" I garbled behind the gag, this position felt even better than the last one. It caused his rock hard cock to rub up against my prostate on every pass. I moaned again and arched my back, pushing my butt farther towards him, causing him to go deeper into my ass.

"You like that baby? You like the way I'm fucking your ass." He said his voice sounding harsh from exertion and lust. I moaned in agreement and nodded my head too far gone in pleasure to care about my dignity or sanity.

He reached a hand up and began working my cock in time with his thrusts, causing me to make an almost keening sound, it felt so good.

"I want to hear you." he said breathlessly, he paused for a moment to reach up and pull the ball gag out of my mouth and throw it aside, before going back to wanking and thrusting, this time with more vigor.

I cried out, my jaw sore form the gag being in my mouth for so long, but I didn't care. All that mattered was that he didn't stop pounding me with his hard cock, and stroking me.

"Say you like it jace, Say you like how I'm fucking you in the ass." He demanded

"I...I...I..li" I gasped out trying to form words.

"SAY IT JACE" He commanded.

"I...I like it" I said through the inhales of breath I was trying to drag into my lungs.

"The whole thing Jace Say you like the way I'm fucking you in the ass. Say it or I'll stop" he said. That was the one thing I didn't want him to do. I was so close he couldn't stop now.

"I like the way your fucking me in the ass." I babbled.

"God you're so perfect!" he said as he fucked me harder, pounding into me causing the whole bed to rock. "I hope your close baby because you feel too good to hold on much longer."

I nodded my head frantically continuously moaning at this point from the pleasure. My dick felt like it was about to explode.

"Good then let's go over together" he punctuated each word with a hard thrust, then did something clever with his hand on my cock that caused my whole body to explode with pleasure. I screamed and felt my hot load shoot up my body and across my face, followed by his own shout as he came hard inside of me.

He fell forward as his hips jerked spasmodically from aftershocks. We both gulped for air, trying to fill our lungs and slow our hearts. I could feel his cock softening inside of me and sliding out. Followed by a trickle of cum leaving my now gaping ass hole.

I was in a daze as he reached up and undid the chains on first one ankle cuff then the other causing my legs to fall back down to the bed. This was followed by a jangling sound around my wrist cuffs. My arms were able to go slack and come down away from the head board. He moved me so I was on my side in a fetal position with my wrists still cuffed in front of me and chained but with about 3 feet of give. There were still cuffs around my ankles but they weren't connected to anything.

I felt his warmth as he spooned me from behind cradling my head on his bicep and wrapping his other arm around my waist pulling me in close. I was too tired to protest or even move. I just closed my eyes and let sleep take me. The last thing I felt was him feathering a kiss across my lips.