Training at the Skyland Club

"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.