Training at the Skyland Club

“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.

He was holding what looked like an egg and rolling it in his hand, as he guided me around the facility, showing that there was a main, all-glass gym overlooking Chicago at all angles, a gym in which older and younger men were working out in almost the altogether and doing as much ogling and touching of each other as working out.

“This is a completely open gentlemen’s club,” he said when I seemed taken aback at how free the men were being with each other in the gym. “Anything the men want and their partners of the moment permit is fine.” And, indeed, there was an X-frame there with a naked young man bound to it and an older, naked man, in full erection, languishly switching the younger man’s buttocks, back and thighs with a riding crop. Another tall, older man, with a wiry, hard body suspended bar lifts he was doing on a bench and watched me as Tony guided me around the room. He was a handsome, commanding man, bald on top, and with a left pec and full arm tattoo in a black and blue, intricate swirling pattern. He looked both like a teamster boss and a sophisticated banker at the same time.

Showing me the egg-shaped object again, Tony said, “This is a Tenga egg, used by a man to pleasure himself. I will be introducing you to this device and others to help you prepare for the client in the future. Having been told the problem, I think, basically, that it isn’t just size. He’s an unusually thick man, I gather, and he has little staying power, so he must be in and finished quickly. Is this true?”

“Yes, basically. But I think I may have trouble with a man of age, because I don’t seem to have trouble taking men younger.”

“Men as big as the client is?”

“Well, no, certainly not as thick.”

“Thicker than this?” he asked as he deftly parted the fold over his crotch and brought out a beer-can sized, long cock and showed it to me.

I gulped. “No, certainly not thicker than that.”

“Good,” Tony said, “because we are going to work on you being open enough to take this immediately when I want to put it in you.”

I gulped again. Part of this therapy or training, or whatever it was, was going to be Tony fucking me. He buried the massive shaft back inside the folds of the black satin harem pants.

“I don’t think it is much an issue of age,” Tony said, smiling. “I noticed that you hardened up when you met me just now and are still hard. I am much the same age as the client.”

“But much better looking and fit,” I said.

“Well, that is a given with the client, and we must work in other areas,” he said. “I think the issue is how well prepared you are when he needs to perform his quick in and fast ejaculation. What we need here is to build in separate preparation time for you so that you are well open before he goes over the edge.”

He led me over to the interior wall of the gym, where I saw that there were alcoves, with beds in them. The alcove could be curtained off from the gym floor. A couple of these were occupied by copulating pairs of men--one having three men working on each other. Tony led me into one with a reserved sign on it. On a table by the bed an assortment of sex toys and lotions had been set out. There were a few masturbator toys, including a Tenga egg like the one Tony had already shown me, but there also were dildos in assorted sizes, building up to one in the shape and size of a stud horse’s cock. Tony lifted this one off the table.

“Please undress and lie on the bed. Before I give you the cock now and the client gives it to you in the future, you should have built yourself up in preparation that this dildo slides in easily. I am told you understand that this process isn’t for your pleasure--that is so that you can give the client what he needs.”

“Yes, that’s right, I suppose,” I said.

“That doesn’t mean that you haven’t taken your pleasure before that. Part of your preparation for the client, if he’s fine with that, can be for you to take your satisfaction from another lover or do it yourself before you go to the client. All the client needs is your compliance and a channel open enough for him to easily do what he wants to do to gain release.”

“I understand.”

He flicked on a TV over the entrance to the alcove and showed me how I could go from channel to channel to view films that showed me how to use the various sex-toy devices in masturbation and porn films showing action. “It doesn’t matter how often you come while preparing,” he said. “What matters is how accommodating your channel is for the few brief moments the client can use it for his satisfaction.”

Tony didn’t leave me immediately. He hovered over my body, fondling and manipulating and making love to me with his hands and mouth, while I sighed and moaned for him. He guided my hand into the folds at his crotch, and I stroked his massive tool while he moved to sucking mine.

“Relax,” he said, pulling briefly away. “Remember that the goal here isn’t for you to climax with him. You can do that beforehand, as many times as you want. The goal is to be open enough for him to take his pleasure after you’ve prepared for him. It’s his climax that’s important. Go ahead and climax with me and by yourself while you are opening your channel.”

With a jerk and a sigh, I did so. He worked some more with the toys as I slowly was opened up. Then he left me to it. “I will be back,” he said, “but I will close the curtain for now. This preparation is something you need to learn to do for yourself before you go to the client.”

With the aid of the TV films, I went through the progression of opening myself to be able to take the horse cock dildo, but it didn’t work in quite the privacy Tony had suggested I would have. As I was getting close to being fully dilated, the curtain parted and the older, bald man who had been ogling me earlier parted the curtain and stood there, handing and stroking a well-hung cock, and watched me at work.

In time, he withdrew and Tony returned. He checked that the horse cock slid in easily, which it did, and then he stripped, showing a magnificently muscled senior body, coaxed my legs to part and bend, feet flat on bed, put a bolster under the small of my back, and mounted, penetrated, and fucked me deep and long in the missionary position. As big as he was, he slid in easily. The contrast between Tony and what I could expect from Gerry Gerson other than that Tony had a beautiful body and Gerry didn’t, was that Gerry would be in and out in less than two minutes but that Tony could--and did--fuck me forever, bringing out another load of cum from me in addition to his own ejaculation.

* * * *

Tony let me rest for a while, saying we’d do another session later, and I dressed and went down to the club’s bar on the level below the penthouse gym, spa, and playrooms. The Skyland Club occupied the top three floors of a thirty-eight story skyscraper. The middle floor contained the dining room, kitchen facilities, bar, and meeting room. The first floor was reception, offices, and the bedrooms of members who were booked for the night. I had been assigned one of the bedrooms.

There were a few others in the bar, but not many. Those who were there, though, were paired up and engaged with each other. I ordered a drink from the bar and found an unoccupied table. Within seconds, the older, distinguished-looking man who had ogled me earlier in the gym and watched me prepare myself to be open for Tony in the alcove off the gym came into the bar, talked to the barman, and came to my table bearing the drink I’d ordered and one for himself.

“Personal delivery,” he said. “I hope you don’t mind.” He set my drink down in front of me.

“Thanks. It saves me a trip to the bar,” I said.

“This one is on me. I hope you don’t mind if I sit here and chat with you while you drink this--and I could go get the next one as well.”

“No, not at all,” I answered. “I’m free for the moment.”

“My name is Dave. Dave Elgin. I know I’m being very forward in watching you in the gym and trying to figure out what Tony is training you to. But you are such a beautiful, enticing young man. Is he training you to be one of the club’s sex workers? If so, would it be too forward of me to ask when you might be established to serve club members?”

I blushed, and in that moment I didn’t connect his name with the building. “No, I think this is a private arrangement,” I think.

“You seem to be free about sexuality and I saw that you received Tony without reluctance, so may I assume you are comfortable about talking about sex--as much as you seem to be about engaging in it with men? If I’m being too forward--”

“No, that’s fine,” I responded. “Rather flattering, actually.”

“That I would show interest in you in a sexual way?”

“Yes.”

“Let me be clear that I am very interested in you in a sexual way. You arouse me as no other young man has done. I would like to cover you, and I would pay you generously to take my cock. It’s not clear why you are here, though, and what Tony is working with you on. Do you have a lover--presumably a wealthy one to be paying for all of this--who you are having trouble accommodating but are willing to try doing so?”

“Yes, he is an older man--in New York. My boss, actually. I am a new accountant in his firm.”

“An older man? You are having trouble responding sexually to an older man?” The worried expression on his face indicated what his real unspoken question was.

“Yes, but he’s not a good-looking man and he’s not in shape.”

“Ah. And I--”

“Oh, you are quite good-looking and in terrific shape for your age,” I quickly said. “No, there is more. He can’t sustain an erection, meaning he can’t engage in much foreplay. He also is extremely thick. Without the preparation of me, I can’t take him before he no longer is in need.”

“He ejaculates before he can get inside you?”

“Yes, basically.”

“And Tony, who also has a beer-can shaft is teaching you to prepare yourself and to be open enough to take your daddy immediately and accommodate him for the short time he can remain hard before ejaculating.”

“Yes.”

“Well, that seems simple enough.” He looked relieved and put a hand on my thigh. I didn’t move away from it. There was the clear indication there that the problems between Gerry Gerson and me on satisfactory sex were not a concern for whatever he wanted to do with me. I was flattered he was so interested in doing something with me.

“Are you in a relationship with just this one man? You seemed willing enough to let Tony cover you.”

“Are you asking if I’m a rent-boy--if my boss brought me in just for his bed?”

“I’m sorry if I’m being too blunt. But, yes, are you available for money?”

“I suppose in some ways I am the man’s paid whore,” I admitted. “But I came into the firm for the job and advancement in the firm seems to be the payment rather than money.”

“But you would go with a man for money? An older man? One who would prepare you well before covering you?”

“Are we talking about hung men here?” I asked in amusement. His hand had moved to exploring my crotch. He found me hard. Again, I didn’t pull away.

“Yes,” he answered.

“I do prefer big cocks,” I said. “It’s the one thing I like about my boss, but unfortunately it’s the one thing I’ve been unable to adjust to in the time needed.”

He took my hand and moved it to his crotch, where I traced a long, hard, thick shaft. I have no idea how it measured up to either Gerry or Tony, but it was a very nice cock.

“I have my own room here,” he whispered. “Will you go with me there now and let me fuck you? I’ll pay you a thousand dollars. I would prefer bareback. I have pills for protection of that, if you are worried. And I am checked regularly. But if it has to be with a condom--”

“I have another training session with Tony in just a bit, so, I’m sorry, I couldn’t now.”

“But you aren’t saying no.”

“I’m here for another day. I’ll have to go to the office tomorrow, but maybe when I come back... if you’re still here then.”

“I will be here,” he said. “Do you mind if I watch you prepare for Tony and then take his cock?”

“No, that’s fine.”

“I’ll pay you five hundred for that, to sit nearby and take care of myself while Tony fucks you.”

“Sure that’s fine, and you don’t have to pay for it.”

In the event, it helped me for Elgin to be sitting nearby and jerking off while I prepared myself. Then when Tony came in, he expressed pleasure with how well I had opened myself. He put me on all fours on the bed, mounted me in a doggy position, slid right in, and fucked me. It had aroused me more to see that Elgin had a long, thick cock and was beating it off in cadence with Tony’s stroking inside me. I gave no thought to how accommodating Tony was to letting Elgin watch us or had I thought of the man having said he had his own room here at the club.

* * * *

I thought I’d locked my bedroom door at the Skyland Club in Chicago that night. In fact, I’m sure I did. That didn’t seem to matter much. He was already in the room and sitting on the bed beside me, fondling me, before I was aware enough to know that someone was in the room with me in the dark of the night.

I assumed it was Tony, and with what he’d done with--to--me earlier in the day, I feel no compulsion to counter what he was doing with his hands. He was sexing me up in preparation to helping me to open up quick enough and dilated enough for him to penetrate me with his monster cock while we were still in heat and to be inside me when we shot off. It was all part of the training, I told myself.

But the more the man worked me, pulled my sleeping shorts off, and became naked himself, the more I realized that this wasn’t Tony. This was David Elgin, who had propositioned me earlier in the evening and who I hadn’t rebuffed. I’d just put him off to the next day when I wasn’t so exhausted from Tony’s training sessions. Elgin couldn’t wait. He somehow had gotten access to my bedroom--which, upon reflection the next day wasn’t a surprise. He was David Elgin. This was the Elgin Building. He owned it. He owned the Skyland Club. He could go and do what he liked here.

Right at the moment he was doing me. And he was doing me well. He was expertly preparing me. The training must be doing me good, because I wasn’t clutching up in the embrace of an older man. I was relaxing and responding. I was opening up as he worked me in the dark on the bed with his hands and his mouth. We moved into the sixty-nine position, and I was sucking him off as he was eating me out. It wasn’t long at all before we were both in high heat, he was in magnificent erection and I was open enough for deep penetration--not an easy slide, but I highly arousing challenge, possession, and stretch as I moaned and he groaned. When he was saddled in close missionary position, my heels rubbing on the backs of his thighs, he established a rhythm of the fuck that I matched with the rocking of my hips.

We fucked at length in total unison and we came nearly together. He barebacked me, coming deep inside me in a series of jerks and releases, both of us sighing. For an older man, he had a flood of cum. For an older man, he also had remarkable recovery. After we’d both ejaculated, he lay there on top of me, taking much of his weight on his elbows and we kissed and nuzzled each other. We both concentrated on him going flaccid inside me.

“I’m sorry. I know you gave me reason I could do this with you tomorrow, but I couldn’t resist.”

“I’m flattered,” I answered.

“I brought pills for you--to head off any possible problem from not using condoms. On your nightstand here. It’s just so much more--”

“I understand. For me too.”

He no longer was going flaccid. He was on the rise again. He gave a little laugh.

“See what you do for me. I hope you don’t mind--”

“Fuck me, Daddy. Fuck me through the night!” In this moment I was totally his. I wanted him inside me, fucking me completely.

It wasn’t through the night. It was just one more time. He turned me on my belly and mounted me from on top and behind. The second fuck was even more vigorous than the first. He grasped my wrists and bowed my torso back tautly to him, as he mounted and rode me high like a jockey, pounding, pounding, pounding, holding me completely his captive. Such a lot of vigor for such an older man.

I slathered the sheets with my cum and he shot off again and again inside me, collapsing on top of me, holding me close, both of us again concentrating on the calming of the storm in the need of his shaft afterward.

I drifted off to sleep with him still on top of and inside me, but when I woke, with daylight streaming in the window, he was gone.

* * * *

He joined me at the breakfast table in the morning.

“Good morning,” he said, giving me a tentatively “I’m not sure how we stand” smile.

“Hi,” I answered. “Please sit with me.”

“Last night... I hope I didn’t--”

“It was fine. No, it was great.” I was certainly getting over any aversion I might have had to older men. Of course this one was a handsome devil compared to Gerry Gerson. But in the dark, and given the preparation techniques I was being given... With David Elgin I didn’t need to take as long in preparation. And, although hung, Elgin wasn’t as big as either Gerson or Tony were. He was much the better lover than Gerson and not any less arousing than Tony.

“Today, perhaps?” He asked.

“Whenever our schedules meet. Certainly tonight, if you wish. I’ll be going back to New York tomorrow.”

“And to the man who arranged this training for you.”

“Yes.”

“You are an accountant? That’s what you do in his business?”

“Yes. I took my MBA at NYU last year. I think I am doing well as an accountant.”

“Ah, a multitalented young man,” he said, and gave a low laugh.

“If you say so.”

“I say so. As you know, I couldn’t hold off. And you exceeded all of my expectations.” There was a paused before he added. “I have a business here myself.”

“Yes, I gathered that. You’re the Elgin in the Elgin Building name, I gather.”

“Yes, yes I am. I rather think I’m as able to keep a young man to pleasure myself as much as the man who sent you here--sent you here because there was a problem in a sexual relationship your boss wanted to cultivate.”

“Yes, I think we have the answer to that though.”

“But I don’t think there is any such problem between us--you and me.”

“No.”

“You could come work for me as an accountant--and to be with me more intimately. You don’t have to go back to New York--with problems you still have to work on.” He brought out a business card and laid it next to my breakfast plate. “I’ve written my private number on this. You can call me any time if you don’t want to answer my offer now.”

“Good until you find another young man you fancy better than me, of course,” I said. I tried to take the edge off of that by giving him a warm smile.

“This is life. One cannot predict such things,” he said. “Regardless, the accountant job is real, it pays well, and it will serve the ambitious. You strike me as an ambitious young man.”

Guilty as charged, I thought with a mental “ouch.” But I wasn’t wholly without principles. I was just a horny young man on the make and willing to use my looks and body to the maximum.

“My boss in New York has dedicated a lot to this,” I said. “I think I owe it to him to try it with him.”

“I understand and respect you for that. It makes me even more interested in you. New York isn’t all that far from Chicago and you have an office here.” He stood from the table. “I can free time for you whenever you are in town. I know how to get in touch with you in New York. And I will when I’m there, if you are good with that.”

“Yes, of course I am. I haven’t made a commitment of monogamy. My boss has said he doesn’t demand that of me--as long as I can give him what he wants as he wants it.”

“Does he want more than you’ve let me know he wants?”

“He wants to include bondage,” I answered.

“And you don’t--”

“No, that’s fine. That part arouses me,” I answered.

I could see that that pleased him. “Then perhaps--”

“If you wish,” I said.

“Good. Let’s leave it at that. For now, the job offer is open. In the short term, I hope you will be willing to service me tonight.”

There it was--the crux of the matter that I had to keep in mind. For men like Elgin and Gerson, this was a matter of servicing their sexual needs. As long as I kept that in mind, I think I would be fine. For now, I had options.

“I will enjoy that,” I answered as Elgin turned to walk away.

And I indeed did enjoy being fucked royally that night by David Elgin. He brought restraints, tied my wrists off at discreet hook worked into the headboard over my head, made me his slave and fucked the hell out of me.

I would keep his card and employ it when and as it benefited me.

At breakfast the next morning I couldn’t help but notice a lion of a man--more a silver fox, I thought--eying me from across the dining room. I was magnificent and seemed to know he was. He acted like he owned the room and the service staff was responding in that way as well.

I stopped a waiter and asked him who the man was.

“That’s Cornelius Vandergrift, the international banker. Fabulously wealthy; a billionaire,” the waiter whispered in passing.

I looked at the man again to see that he was still looking at me, assessing me, clearly interested. I wondered if he might have an opening for an accountant.