I was in Boston for business and went to a local adult bookstore to score some action. Unfortunately, there were only a few people there. I decided to look around at the movies that were available to see if something would be good to take back to the hotel room. I started in the straight videos but soon moved to the bi-vids. After looking at a few movies and deciding against them, I heard a voice say “you know the real thing is better than the movies”. I looked up a little embarrassed to see this huge guy standing next to me. He was in his mid-40s and had to be about 6-4 tall and well over 300lbs – most of it muscle.
He and I exchanged a few words and then he asked if I wanted to join him for a beer at the bar across the street. My heart raced with anticipation, as this guy was quite good looking and from the bulge in his jeans was well hung. At the bar, it was a little awkward at first talking he introduced him self as Cory and I in turn introduced myself. We soon found a common interest in football. I learned he was a NFL lineman for a few years for the Tamba Bay Bucs but had to retire early because of injury issues. After a while the topic turned to our wives and sex. Then he asked if I had been with a guy before. I hesitated but he said it was ok he had been with a few. I fessed up that I had sucked a 3 guys off. Soon, he invited me back to his hotel room and I accepted.
We walked up to the Hyatt and through the lobby. I was a bit self-conscious as thinking everyone was watching me knowing I was going to suck a guy’s cock. We went up to his suite and he started to undress. I followed and undressed, uncovering my fit 6-2, 180lb body. He moaned as he commented he liked what he saw and he appreciated my hairy body and average size cock. I looked at his amazing physique, and it was clear he still lifted weights. My eyes dropped to his semi-hard dick. It was dark and hairy and already pretty thick. Cory tuned in some porn on the TV and we laid in bed. All of a sudden he leaded over and f***efully started to kiss me. Although not my thing, because of his dominate attitude I kissed him back.
He leaned back and pulled me over to his chest. I sucked both of his nipples and then he pushed my head down to his cock. I rubbed his cock and licked it. It was only 6.5 inches long but it grew very thick. So think I could just get my had around it. I licked up and down his shaft and sucked his balls. We shifted positions. I got on the my knees on the floor and he stood in front of me. I returned to licking his shaft and he said “open wide and stick it in your mouth”. Man was we thick! I had to stretch my jaws just to get it into my mouth. My jaw was uncomfortably stretched and I could only get about 3 inches in my mouth. I only was blowing him for about 30 seconds, and he said “oh fuck I am going to cum”. He pushed my head down as he arrived at his climax. It was all I could do not gag as he started to cum.
As he came, he held my head on his dick shooting wad after wad of cum, flooding my mouth. I tried to swallow but the girth of his cock made it difficult and most of the cum ran down my chin and neck on to my chin. As his orgasm subsided he pulled out of my mouth. Almost apologetically, he told me he did not get blown that often and thus he came quite quickly. Frankly, I was fine with him cumming quickly, because my jaw hurt.
Cory proceeded to pull my cum covered body up on the bed and bent over taking my rock hard cock in his mouth. MMMM.. He was masterful at sucking cock and soon I was approaching the point of no-return. He pulled my dick out of his warm mouth and stroked it with his strong right hand. Within in seconds I was reaching my climax. Cory loosened his grip on my rock hard cock delaying my release by a few seconds. I screamed as I shot a huge load over my belly. Cory squeezed the remaining drops of cum from hard dick and then proceeded to rub his and my cum into my hairy chest. He collapsed beside me on the bed as we both caught our breath.
I guess he saw the disappointment in my face that everything happened so fast. We had only been in his room about 15 minutes. He told me to stay, and that he would be ready for round two in a little while. . We watched an NBA game for a hour the Cory turned the porn channel back on, signaling his readiness for round two. I reached down and started to massage his cock and he reached over and stroked me back to full mast. He then asked if I ever had anal sex with a man. I told him no, I had not. He said he wanted to take my anal virginity. I was nervous and truthfully scared, especially because of the thickness of his cock. So, I declined his offer
He then asked if I had ever had my ass eaten by a guy, and said no, but I would probably enjoy that. He piled up a few pillows on the bed and had me lay over top of them. My ass was in the air, and my head in a curled up blanket. Corry, then spread my cheeks and I felt his tongue start at the top of my crack and trace down to my asshole. He circled my asshole and the feeling was exquisite. He reached under me and massaged my dick. Soon he was sticking his tongue in my asshole. Hmmmm. I was loving the feeling. Cory moved his hand from my dick, leaving it aching for pleasure and started playing rubbing my asshole with a finger. He gently worked his finger into me over the next minute and I started to push up to take his finger deeper. His finger did hurt a little but I soon started to push back on it help make it feel better. Cory, keeping the finger in my asshole, reached over and got something out of the top drawer of the nightstand. I felt a cool wet sensation and figured he was lubing my asshole. As he pushed his finger it worked the lube, I started to groan my approbal. His finger was getting me horny and I was waiting for him to ask. Soon Cory asked if I had changed my mind about getting fucked in the ass? I did not answer. And he said I will take that as a YES. I still did not say anything as I was still scared of this thickness stretching my ass.
Cory applied a little more lube to my ass and then pulled out his finger. Cory told me to reach back and spread my cheeks and as I did I knew there was no turning back. He positioned his big headed dick at my tight opening, gently rubbing my outer anus. It felt really good and I relaxed a bit succumbing to the idea I was going to the idea that I was going get fucked for my first time. Cory started to push his dick in until it met the resistance of my inner ring of muscles. He paused and moved back out then slowly pushed into the head back in, but did not stop . The pressure on my anus ws intense and then I felt my ass give way and his thick dick head popped into my ass!. Immediately, I grabbed the sheets, and screamed “Damn”. Cory immediately pushed my hips down with this hands trapping me as I tried to pull away. I struggled but he continued to penetrate me deeper with each small stoke. “Fuck, Fuck, Fuck” I kept saying. He kept me trapped and proceeded to fuck me very slowly with long deep strokes. My asshole felt stretched to the limit as he kept fucking me. Cory told me that my ass was fucking tight and it was making his dick feel really good. I thought that is nice because my ass fucking in pain. Cory told me to stop resisting and relax. I kept grabbing the sheets, but did try to relax a little. He started to ease up on the pressure on my back and his idck started to slide more easily in and out of my rear. He kept saying “damn this feels great” as he fucked my tight hole. The pain subsided just a touch and my cursing turned to just grunts as he picked up the pace a bit. I could really fell him deep inside of me and as he was now going balls deep on every stroke. After about 5 minutes or so, he slowly pulled out. He had me turn over, and positioned me on my back with my butt raised in the air on top of the pillows. He squirted a bit more lube on his dick and got ready to mount me again. He put my legs up over his shoulders and positioned his hard cock at my sore rosebud. Cory told me to look at him and I opened my eyes and looked into his. He looked at me very intently as he pushed back into me. I again grunted and cursed, but this time the pain was a bit more tolerable but the fuck was every bit as intense. Within two strokes he was back at fucking me slowly but deeply. In this position his dick inside of me felt good although my anus still hurt from being stretched. He had me start to stroke myself. The feeling of my hand on my dick and his cock inside of me was incredibly intense. I guess this is what is meant by “hurt so good.” My painfully stretched ass and the pleasurable sensations from deep within where combining to really bring me close to cumming. Sensing my arousal, he told me to stop jerking for a while – that he did not want me to cum just yet. Cory then started to fuck me really hard. Yes, the pleasure turned back to a bit of discomfort from the hard fucking, but I was somehow enjoying it. I was saying fuck my ass, fuck my ass you stud. Cory’s breathing started to speed up and as I looked at him I could see his chest get red. He urgently told me “now, jerk now.” I reached down and rubbed my cock. Cory was approaching orgasm and so was I, Cory pushed deeply with all his weight and groaned. This started my orgasm. As he shot his come deep into my ass I could feel my ass contract around his cock as I shot my cum on my tummy. Both of our orgasms lasted an very long time.
As Cory, collapsed he pulled out of me. I reached around and felt my sore asshole and it was partially gaped from the intense fucking I just had. Cory told me to rub the cum into my chest which I willingly complied. As I turned to my side, and rolled off the pillows I could feel some of his cum run out of my asshole. We rested for a bit, then he told me to get dressed and leave. I was not allowed to wash up. As I walked from his room, through the lobby and out to my hotel 4 blocks away, I could feel cum leak from ass, and could smell cum on my chest. This was my first true walk of shame, and I wonder how many people realized what I just did.