Let me know how you like this story, if you I like it, there will be several continuations.
It was 9:30pm on a Thursday Night. I had just left a meeting with some business associates in downtown NYC. I was debating taking the Path back home to NJ, or spending some time in the city. I wasn’t really hungry, but could use a drink, so I decided to go to a bar. But where?
I called my girlfriend, told her I was going to stay in the city for a few more hours, so I wished her a good night, and told her not to wait up for me.
Not only was I in need of a drink, but I was horny as hell. Not horny for pussy, but really wanted to suck a nice big rock hard cock. I’m what you may define as a size queen. As a closeted bi-sexual, it’s what I like. I thought of this bar I went to on Christopher St. a few years ago, it was a gay bar, and I was more than certain I could get off. So I flagged a Taxi and headed to the bar.
I walked in, the room was fairly large, with a bar shaped like an oval, in the center was the bartender and all the liquor. The place was relatively quiet, just a few people sitting at the bar, a couple older men singing at the piano to the farther end of the place. Except for the bartender the crowd was really not anything worth looking at, at least not my type. So I said to myself, “fuck it” I’ll get a beer and leave. I sat down, ordered a beer, and the bartender a young guy, I say around my age 25 or so, but had smooth dark skin, almost a caramel complexion, most likely from tanning, served me my drink. He was definitely good looking, but very feminine, probably a bottom, so I knew it wouldn’t work out. I was about to pay him, but he said the drink was taken care for. I asked who, and he pointed to a man sitting at the opposite end of the bar. The guy he pointed to had to be over 60 years of age. He had a helmet gray-white hair, slightly wrinkled face, yet distinguished looking, he was wearing a dark suit, with a white buttom down shirt and a red tie. He may have been good looking at one time, but right now he seemed to me to be nothing more than an old man, not my type at all. I looked at the old man, smiled, tilted my head in despair, and faintly asked myself, why? Now I was rushing to drink my beer, and leave as quickly as I could, hoping my old man admirer would not want a conversation with me. Maybe buying me a drink was enough to get him off. At least I hoped. And then sure enough, he stood up, made his way around the bar, and sat right next me. He was a tall man, I say about 6’2″. His body was average looking, not muscular, but not soft either. He looked firm.
“Is this seat available.”
“Yes, please sit.” I reluctantly said. What was I supposed to say?
“My name is Harry,” the old man said extending his hand.
“Well Jack, how are you.”
“Not bad, just tired, thought I’d stop here for a drink, then make my way home.”
“You live in New York Jack.”
“No, I actually live in New Jersey,” I whispered.
“I’m from LA, arrived here yesterday, for a business meeting.”
The pleasantries continued for about five minutes, Harry did most of the talking, and answered yes or no. At some point I thought the old man would get the hint, but he seemed oblivious, or maybe just persistant. All of a sudden, he began to talk about sex, and it was then I was ready to leave.
“You know Jack, I’ve come to this bar several times in the past, and I can remember there being guys sucking each other, right on top of this bar. How times have changed, and I can’t begin to tell you how I’d love a blow job right now.” Now the old man gave me this sick looking grin that I immediately, got up, and said abruptly, “I have to go.
Then Harry grabbed my arm forcefully. I was immediately startled, I never thought this old man could have such strength, and then he said to me, “I have a proposition for you, how would you like to make a thousand dollars.”
“How” I replied. I love money, so when you over me a proposition where I can make money I’m all ears.
“Jack, come with me to my hotel room, suck my dick, and I’ll pay you $1,000.”
I said no way, but at the same time I declined, I was debating whether to do it. Hell it’s money, money I don’t have, but then I’d have to suck this old man little wrinkled weiner. I couldn’t, no way. And then the old man said:
“$2,000, no string attached, just suck me off.”
“What the hell,” I said. And I accepted.
About an hour later, in a taxicab, without a word said between the two of us, we made it to his hotel. I was surprised to see that it was the Plaza Hotel. I figured the guy was wealthy, I mean after all how many men offer $2,000 to a kid at a gay bar for a blowjob. But then again, it was an old man, so anything was possible, at least I thought.
We entered the lobby, and made our way to the elevator, and he hit the penthouse button. Ok the guy definitely had money. Even if his business paid for the trip, the underlings most certainly do not get a penthouse suite at the Plaza Hotel. We exited the elevator and entered his room, and it was magnificent. Marble floors, windows 2 stories high, wet bar, etc. etc. just beautiful. He asked me to wait in the living room area, as he changed, and told me to make myself at home. I walked to the bar, made myself a drink, sat on the couch and waited for him.
Honestly I could not wait for this to end. I just wanted the money. Whatever horny urges I had were gone. You see, I like men my age with big cocks. That’s it. This man, I figured could barely get a hard on, so I was dreading the thought of even have to look at his cock, forget sucking it. But $2,000, how could I refuse.
About 10 minutes later, he walked into the living room, wearing only a white bath rob. His posture was excellent, he stood straight up, actually I thought he kind of looked sexy in that rob, kind of like those distinguished rich men in movies. But again, nothing I would want to be naked with.
He walked up to me, and without a word handed me a wad a of hundred dollar bills, I knew it to be the money promised to me, I thanked him and put it in my pocket.
I was seated at the edge of the couch cushion, and it was then he started to untie his rob, I made what seemed to be a loud gulp of fear, I closed my eyes, he opened the rob, he pushed the sides under his arms, at that point I opened my eyes, and what I say was completely unhuman. His cock hung like that of a horse. It had to be at least 9 inches long, and it was still flaccid. It was uncut, and his foreskin, hung ever so slightly over the head of his cock. His manhood was so thick, it reminded me of a fire hose. The shaft was smooth looking, no marks visible, not even a beauty mark. And his balls looked like two golf balls hanging in a sack. They were low and huge. Only a little gray hair above his cock, but the cock and balls were free of any hair. It was georgeous.
The old man looked down at me and smiled, “You didn’t expect that Jack, did you.”
I laughed, and said no way.
I cupped my right hand under his cock, and lifted it towards my mouth. You may have needed a crane to lift his manhood up, it was incredible. With my hand I pushed the foreskin back and revealed the monstrous head, opened my mouth and slowly let his cock enter. I sucked on it like it was a lollipop. It tasted so muscular and so manly. I felt his cock pulsate in mouth, as it grew, yes it grew, bigger and bigger. I couldn’t believe it. After a few minutes his cock was almost a foot long, maybe bigger. It was incredible. I kept sucking on it, jerking it off with my right had. His cock was so big my hand could not, would not grip totally around it. I pulled on his balls, occasionally licking them, but my main goal was to make love to that cock. As I sucked him, I started playing with my own hard-on through my pants, and then he asked me if I’d like to strip, I immediately took all my clothes off, and jerked my cock as I sucked him. He kept moaning, telling me I was a great cocksucker. He placed his two hands behind my head and thrusted his cock in my mouth. At one point I tried to deep throat him, getting almost half his cock in my throat. This was a size queens dream, and I was in complete extasy. After a few minutes more, he said he was ready to cum.
“Jack you want this cum in your mouth.”
“Yes, please yes.”
He took his cock out of my mouth, jerked it off, and came in my mouth, all over my face, on my chest. Everywhere. It felt like gallons of hot jizm all over me. Then I came, what also seemed like gallons, all over my chest. I was lying on the couch like a man whore, covered in cum like a little slut. I loved it.
“How was that Jack”
“Harry, it was unbelievable.”
The old man laughed and got me some towels. And then asked if I wanted to shower. I said yes. I couldn’t exactly go home to my girlfriend with cum in my hair.
We walked into a shower stall, made for two, and the two of us went under the running water, washing ourselves off.
“So Jack, you seemed very surprised.” Harry said.
“I never expected your cock to be so big,” I admitted.
“Most people don’t, it’s 14 inches long you know.”
“Really,” I said, thought I do think he may have been exaggerating, then again, I had it measured at 12″, so really when your that big whats an extra 2″.
I then said, “truth is, I love big cocks, so I was pleasantly surprised.
He then laughed, “well young man you are the best cocksucker I’ve ever had, never has anyone made love to my cock with their mouth like you.
I didn’t say it, but his cock made love to me.
“Jack, you have a nice man,” Harry said as he looked down on my bubble butt.
I hesitantly thanked him, I mean he could look, but don’t put anything in there.
A few minutes later we dried off, and he asked me if I wanted a drink, maybe we could spend few minutes in the Jacuzzi.
I was hesitant at first, but then I stared at that monstrous cock again, and said yes. After all, I should earn my money right.
A half-hour or so, we were in the tub, talking about work, his wife, my girlfriend. It was then I learned this man was a billionaire, highly successful, and In the same business work as me. I was actually intrigued by this man, and it was then he asked me,
“Jack, I’m mesmerized by your ass, I would love to fuck it.”
“Sorry, Harry, but I don’t do that.” Truth is, I love to suck, be sucked, once or twice I even fucked a guy in the ass, but that is the extent of my gayness. I can’t even take that pain of a finger in my ass, forget that monstrosity. There was no way.
“Jack, I’ll pay you an extra $5,000 to fuck you.”
“Look Harry, I just can’t take the pain.”
“I’ll be gentle, I promise, how about $6,000.”
This is a guy who gets what he wants and pays to get it. Reluctantly I accepted, but implored he had to use so lube. He imediatley got out of the tub, brought over a bottle of lube, and the told me to lift my ass out of the water and bend over the tub. At first he started to lick my hole. He was an odd feeling, but then it felt kind of good. My cock was getting harder. My ass was his pussy, and he was licking it like crazy. I was beginning to really love it. Then a felt his lubed finger enter, and then the pain, increased. I wanted to scream, but closed my eyes, and coped with the agony. As his left finger was fucking my ass, I felt his right hand cup my semi-hard cock now, and he jerked me off as he finger fucked me. I then became hard as a rock, and was again enjoying the ass play.
“You got a pretty big cock there Jack.
Actually I’ve always had compliments about my cock, it’s 8 inches, cut, 6” thick. But compared to this man, it was nothing.
It was a minute or too later, the old man stood up. I heard him rub lube on his manhood, then felt some on my ass, and his cock, pushed against my hole, and then I felt complete agony, despair, pain beyond my wildest imagination. I let out a moan louder than I have ever screemed, and his huge fire hose entered my ass. He thrusted slowly, then a bit faster. He was gentle but the pain never subsited. I just wanted him to cum. He asked if I liked it, and I whispered an unconvincing yea. It was then he stopped and ordered me to relax. He said if I relaxed my ass muscles, it would feel better. Relax I have the fucking Sears Tower in my Rear, and you want me to relax. But I did, he thrusted again, and all of a sudden, my cock became rock hard, the of his cock in my body, went right through me. My ass was his pussy, and I was his little whore, I liked it. My moans changed from that of agony, to that of pleasure. I then couldn’t believe my ears, I told him to go faster. And he did, he went all the way in, his balls slapping against mine, faster and faster. I jerked my cock off like crazy, I was ready to cum, just holding back waiting for him, and then he pulled out and came all over my ass, I came, it was amazing. He rubbed the cum with his cock all over my newly fucked ass. I turned around to look at him, and he smiled.
“How did you like that Jack.”
“Harry I can’t believe it, it was great.”
“Better than sucking.”
“I enjoyed it Harry, but I’d rather suck your dick.”
“Well it could be an occasional thing we do.”
What the hell is he talking about, he’s going back to LA. Maybe just a wrong choice of words. But then he said:
“Jack, I have an office here in NYC, and in desperately needs a manager. Since you and I are in the same business, and from my conversation with you, I think you would be the perfect manager. How would you like the job?”
“How much does it pay?” I asked.
“$200,000.00 a year.”
“Oh my, but what’s the catch.”
“No catch, other than, every now and then I may need you to accompany me on some business trips. Once a while I may need you to fly to LA, to give me one of those great blowjobs.”
“What am I then your hired whore,” I said laughing.
He then grinned, and said, “if that’s what you’d like to call it. I’ll make you into one of the most richest business men in country, you’ll have a mind unlike any other, and in return, I want to see you at anytime, within reason, when I’m horny.”
I then said, “Well big guy I am yours, I accept.”
“Good Jack, you are going to have a great time, and not just with me, I’ll pay for other men to join us, with cocks bigger than mine, and if you want a woman, threesomes foursomes orgies, whatever you want, I’ll provide. But there is one more thing.”
“What’s that Harry.”
“I’m horny, come here and suck my dick.”
I took his enormous cock in my mouth, and sucked my new boss again. This is definitely going to be the best job I’ve ever had.