"Relax. Take it. It will be great once I'm in."
Easy for Gerson to say, but it wasn't working with me. It was just that he wasn't all that attractive or that he had what they called a beer-can cock in the extreme--extraordinarily thick if not all that long. Gerson was my boss at Gerson Enterprises. I was just out of an MBA program at NYU and I wanted to get ahead, so I'd let myself be suborned by the CEO, Gerald--Gerry--Gerson. We were at a Catskills cottage of his, in his playroom, and he was trying in the damnest way to get inside me while I was trussed up in a leather sling. It wasn't just because he was pretty old, and paunchy, and couldn't hold an erection long enough to prepare me well or that he was so thick when hard or that he had to have the fetish of bondage and force to keep it hard enough to obtain liftoff. It was a combination of all three.
I was OK with younger guys. I wasn't promiscuous, but I had no problem attracting interest, and I'd partied with another accountant at Gerson's, Ted, who told me that Gerson fancied me and he could put us together if I was interested in expanding my profile in the company. At twenty-three and with an MBA under my belt, I was interested in moving up as quickly as possible. Although heavy set, Gerson didn't look too bad in an expensive suit.
He wasn't nearly as arousing in the altogether and burdened with the sexual issues he had. The cock, for starters, was impossibly thick when hard and I wasn't much of a player, at least as yet. The main problem, though, was the combination of his fetish, his size, and his staying power.
"Open up. Open up, damn it!" he cried out, hovering over me as I lay on my back in the black leather sling, my wrists bound up the chains by my head and my ankles bound up the chains at the base where he was standing, grasping my throat with one hand, and working hard to stuff himself in me with the other. I panted and writhed and cried out at the attempted stretch of him and he huffed and puffed and pushed. He was in, past the sphincter, and I thought it was going to work this time, but he jerked and lost position, and came inside his condom between my thighs.
"Sorry," I whimpered. "I thought maybe--"
"I thought so too," he said, pulling away from me, looking disappointed.
"I guess I just can't--"
"No, it's not just you. It's the combination of things. But you need to relax with the bondage and be able to open to my size quickly."
"I guess you need to just try it with someone else."
"No, I don't want to give up on you being able to take me. You're the sexiest, best young guy who I have found to try it with me. We'll have to do something. We have time."
I groaned.
For the rest of the afternoon, as Gerson was off at the edge of the woods, making phone calls, I stewed about the situation. I had agreed to the arrangement. There had been no reluctance there. I had a great, good-looking body. I'd used it to my advantage in college. I had no qualms about using it to my advantage in business. It just wasn't fitting with this important boss man.
Later in the afternoon, I was sitting on the cabin's porch, going over some accounting work, when a pickup drove up to the cabin and a big, strapping black guy got out. Gerson came up from where he had been making phone calls at the edge of the woods.
"Come into the house, Jack," he said. "An escort agency has sent this man up to help us."
And help us the black bull did, although I never did hear what his name was. In Gerson's special room in the house, the black guy embraced and kissed me. We slowly undressed as we fondled each other and he frotted our cocks. His was huge--as thick as Gerson's but so much longer--a black mamba snake of a shaft with a big purple head on it. If I could take his cock, I'd be able to Gerson's.
He lay me back into the sling and bound my wrists and ankles on the four chains. He ran his hands all over me and knelt between my legs and ate me out. I was writhing and moaning. And Then I was huffing and panting and giving little cries as the big, thick fingers of his hand penetrated. He took his time, working me with the fingers and more with the one hand while hovering over me and kissing and licking my body and exploring with the other hand.
Then he fucked me. He had opened and prepared me to the point of my being able to take and stretch to him. His hand was removed, to be replaced by his cock, which just slid in, and he fucked me. Toward the end of this, Gerson came into the room, naked, his cock worked up to an erection and crowned already with a condom. The black rent-boy pulled out of me and stood aside. Gerson could penetrate with his beer-can cock now. Not more than twenty seconds later, he jerked and came. He'd managed to do what he wanted finally. Everything had come together. He got his fetish, I was open to his requirement, and he managed a penetration and quick ejaculation.
Later, at dinner, being hopeful that something long term would work out after all, I was brave enough to say, "So maybe that--"
"That worked, yes," he said, giving me hope, "But I can't bring in a rent-boy like that every time I want to fuck you." That dashed my hopes.
He didn't comment more on that for the moment but changed to conversation to work matters. I could tell he was mulling something over in his mind, though. I was afraid that he was deciding that this was just too convoluted an option to provide enough satisfaction. The last thing he brought up in the evening didn't seem to be related. But I guess, looking back on it, it did.
"I want you to go out to Chicago and become familiar with our office there," he said. "I'm going to arrange to send you out there for a week and put you in good hands."
There it was, I thought. He was pushing me aside, getting me moved out of New York. He'd try to get what he really wanted from someone else.
But that turned out not to be what Gerry Gerson had in mind for me--and for us.
* * * *
The indoctrination in the Chicago offices of the Gerson Enterprises turned out to be just what Gerry Gerson had told me it would be. It wasn't evidence that he was tired of trying to get it on with me and was sending me away from New York. I spent two days in the office in downtown Chicago comparing and contrasting how the accounting was done here with what we did in the main New York City office. I was treated with kid gloves--precisely as if they knew I was being groomed for greater responsibility. There was no evidence that they realized that I was still being groomed to provide sexual satisfaction to Gerald Gerson himself.
That part was also evident during my Chicago trip. During the workday I was given a white-glove, in-depth look into the Chicago office operations. In the evening, though, I was turned over to a beautiful mature man named Tony in the Skyland Club penthouse men's spa and male brothel in the Elgin skyscraper on North Columbus Drive building, two blocks off the lake at the Navy Pier. From dinner on, I was hosted at the club, including sleeping there--and not alone.
Tony met me at reception at the Skyland Club after I had been checked into my room there the first evening. He was a gorgeous man, evidently Italian, of middle age, about the same age as Gerry Gerson. There was another similarity in the two men, but none that were evident. He was on the heavy side, but in solid, well-proportioned muscularity. He was handsome of face and hirsute. He had a flowing mane of salt-and-pepper hair, a mustache and a trimmed beard. He was elegantly dressed in a black satin top and trousers combination that hung loosely on his body. The top was open half way down to the navel to show a sexily hirsute chest and a heavy gold chain around his neck. He obviously was very comfortable in his clothes and his body.
He greeted me with a big smile and an immediate admission. "I have been employed over these two days to make you more comfortable with having sex with my client." By that, it was obvious he meant Gerry Gerson, although he never mentioned his name. I had been told I would be undergoing sexual relaxing treatment while in Chicago, so that didn't come as a surprise. His age--going with older men had been part of the possible reason I was having trouble taking Gerson's cock--surprised me, because I found Tony to be highly arousing, despite the age.
