Kept Men

Even before I got off of the train from Raleigh, North Carolina, in Asheville, where, as a New Yorker, I was completely out of my element, I saw that the man, himself, had come to meet the train. I didn't realize that I would be relieved to see a familiar face, albeit one I was a bit apprehensive about, as I started this new venture, but I was. I was to take up my new duties as an associate lawyer, not long out of Yale University and new to the South, in a branch of our law office in Asheville principally to serve the Vanderbilt family, which was building a country estate there. Calvin G. Holloway, the senior partner in charge of the Asheville office, was standing on the platform. An older black man in livery was there as well, and a younger, nervous and despondent-looking young man, standing next to luggage was there too.

Holloway wasn't here just to meet me, I quickly learned. He was here to put the other young man on the train to return to Raleigh. And when I came off the train and onto the platform, the other young man, Harry, gave me such a venomous look that it almost sent me reeling back up into the passenger car. It was almost as if it was my fault I was arriving and he was leaving. As it transpired there was a cause and effect there, but it was hardly my fault--or I didn't believe it was blame that should be exclusively--or even primarily--assigned to me. It all, of course, revolved around the commanding Calvin G. Holloway.

"Benton," Mr. Holloway said as I turned my gaze from Harry. "Benton Barkley, is it not? Welcome to Asheville and our branch of Collins, Bagwell, and Holloway here. We were seeing Harry off, so it was no trouble meeting your train."

That set me back a bit. Whether pretend or not, he was acting like he barely remembered me. How insulting was it that someone who had recently stripped and fucked you wasn't sure they remembered you? But that was Calvin G. Holloway--he floated above we mere peasants. I had been easy for him. He was a powerful and commanding man. He had laid me and I had given no thought to deny him.

He gave me the distinct impression that he normally wouldn't be meeting the train of a lowly associate lawyer in the firm himself and that this was a great honor. I was to be an assistant of a sort, more-or-less a gofer, for him, but no more than an associate lawyer still on probation.

And, as he was one of the senior partners, and having been sent to hold down this prestigious branch of the firm to serve the Vanderbilts as lawyers for their Biltmore estate, for which construction started the previous year, 1888, I couldn't deny that he was in an exalted position relative to me. The firm was ginning up with the hope that landing the Vanderbilts as clients, if only for their southern holdings, would lead to other connections with the New York elite. I, having come from there myself, would not, I am sure, have been hired otherwise.

"After you put Harry's luggage on the train, please carry Benton's luggage out to the carriage, Jacob. We will be in the bar until that is accomplished."

"Yas, sah," the very brown older man in livery said, and, with that, Harry of the despondent and sour look was consigned to Jacob, and Holloway, taller and thinner than I--and so much more distinguished looking--put an arm around my shoulders and led me toward the station bar. The way Holloway held me to himself, I knew that he remembered me. He'd certainly spent enough time inside me. What he remembered now was that he owned me.

"We have an apartment for you near our North Lexington Avenue downtown offices, and it will be cleaned for use tomorrow, but for tonight you can come to my house on West Chestnut Street in the Montford District. I think you'll find that more comfortable than a hotel."

This was coming as very much of a surprise. I was to take on assistance duties to the man, but I had assumed, by the way he had greeted me at the train station, that he would hardly recognize who I was in the office for some time to come. I certainly hadn't expected to be entertained in his house on my first night in the city. "I could certainly go to a hotel," I said. "I wouldn't want to impose on you and Mrs. Holloway."

"Nonsense," he answered boisterously. "Mrs. Holloway is on a buying spree in New York City. This exposure to the Vanderbilts and their acquisitiveness, as favorable as it is to the law firm, has become a very bad influence on my wife, I'm afraid. No, I'll be all alone this evening and night. I'll be happy to have the company."

I also was to find that he wasn't going to provide the entertainment; I was. That really shouldn't have surprised me either. He wasn't going to pretend like he barely knew me tonight; he was going to become reacquainted with every inch of me. Everything was moving so fast, however. I could hardly catch my breath. I certainly wasn't to have any control over getting my bearings in this new job.

* * * *

Off we went from the train station in a carriage, with Jacob at the reins, quickly getting into the plush tree-lined Montford district to the northeast of the downtown area, where the Holloway house was located. It was a large, wooden Victorian mansion set well back from the street. I was given a well-appointed bedroom that was larger than my entire set of rooms in Raleigh had been, but only my luggage was to occupy the room.

When I came down from my room at the dinner hour, having, after a sponge bath, exchanged my travel clothes for the best clothes I had that could be considered more casual than business suits for the office, I found Holloway in his study, drinking bourbon and smoking a cigar. He was wearing a red silk dressing gown over black trousers. He was bare-chested under the dressing gown, with red silk suspenders, and he showed as quite a fit man for his age. His curly chest hair was darker than that on his head but, like the head hair, was shot through with gray. The room had been darker when he covered me before, and he took me from behind then, so I only now was getting a full impression of the man under several layers of clothing.

Taking a look at me as I entered the study, he tugged his robe even more open to show that his pecs were still hard and his nipple was puffy within a swirl of curly hair. He wanted me to know why we were here alone.

"Is that what they wear in New York to go to an intimate dinner?" he asked. I was wearing breeches and a white cotton shirt, with leather suspenders. He reached over and unbuttoned three buttons of my shirt. "There, that looks more comfortable." He slid his hand in under the material and caught one of my nipples between thumb and forefinger. He wasn't wasting any time. But then, he'd held me naked before, so this was just teasing foreplay to where he knew he could go.

"I'm sorry, sir," I answered. "It is what I have. I wasn't in Raleigh long enough to learn to dress for the region." I can't say I was taken aback that he was working me and getting into doing so so quickly. I had some inkling of why I had been given this job and what was expected from me. My own proclivities prevented me from being shocked by any possibilities. I had already noted that Holloway was a handsome and fit man--for his age. I was known to be fine with men his age, most of whom were not as well-conditioned as he was.

"No matter," he said. "We will go shopping before we introduce you to Ashville society--or the aspect of the society that I float in--and within our branch of the firm. We do have our own ways and expectations here."

I could tell that was so from the way he was dressed, which, while obviously expensive and elegant, was not what one would wear to a private dinner in New York--an intimate one, possibly, although I hadn't gotten into that in New York, although I had, in fact, been to intimate dinners with men Holloway's age. I had been intimate with Holloway myself. Networking with the powerful--although undoubtedly not this intimate--was one reason my family had been in favor of me coming south when my father, who had dealings with George W. Vanderbilt, the builder of Biltmore, heard that Holloway's firm in Raleigh was looking to hire an associate from New York of Vanderbilt's general age. The already fabulously successful entrepreneur in railroads and steamships was just a year older than I was.

"You're quite a fit and enticing young man," Holloway said, not offering me a seat as I stood before him, and he reached up, his fingers still rolling one of my nipples between his fingers. "Does this arouse you, young man?"

"Yes," I answered.

"I'm sure it would arouse me too," he said, looking pointedly at my hand, dangling at my side. I got the hint and raised my hand, sliding it under the lapel of his robe, finding and teasing his nipple out of his swirl of chest hair. He gave a pleasured grunt as I grasped the nipple between thumb and forefinger as he was doing and squeezed and rolled it.

"You do know why you have been selected to support me in the job here, don't you?" he asked, giving me a pointed look.

"Yes, sir," was as much as I needed to answer. He smiled and reached over with his free hand and released another of the buttons on my shirt. What was what was being clearly established.

"You are going to give me whatever service I demand of you, are you not?" he said.

"Yes, sir." And that settled that.

He released my nipple and I did his and he said, "Shall we go into dinner and fortify ourselves for later pleasure?" He stood and moved toward the study door. I followed.

It was just the two of us at dinner at a table that would seat eighteen. He sat me immediately to his right, with him at one end of the table. The meal, of course, was sumptuous and was served by three male servants, all of whom disappeared when they'd done their share of the duty, giving me the impression Holloway and I were the only ones in this big house when we'd withdrawn back to his study for port. During dinner he outlined that I was there principally, from the perspective of the law office, because I was a New Yorker and of George Vanderbilt's age, which was twenty-six at the time. I was to assist in discussions with him over legal matters in the construction of Biltmore and apprise Holloway of any reactions or strange word uses from the young millionaire that might be elucidated by his New York origins. I was not to become too intrusive, however.

It was then that I learned that I was directly replacing the Harry who we'd seen off at the railroad station when I arrived. He'd been Holloway's assistant and more, I surmised, for the last year. But he would not be a help in understanding the ways of New Yorkers as he was a southerner, so he was being shipped back to Raleigh, replaced by me. I had been hired because I was a New Yorker with southern roots. I was careful not to tell Holloway that my father had business connections with the Vanderbilts, though. I wanted it to be quite clear that I would be working in the law firm's interests.

We were sitting in two overstuffed, facing lounge chairs in his study after dinner, drinking port, smoking cigars, and listening to the scratchy, but fascinating, sounds coming out of what Holloway said was a gramophone, which only recently was patented by a friend of George Vanderbilt's, Emile Berliner. There were only a few in existence at that point and Vanderbilt had loaned his gramophone to Holloway until a place was safely built for it at the Biltmore Estate. Although it was somewhat hard to tell, it seemed to be some sort of classical piano music. Chopin, Holloway said.

In any case, it was setting a mood--at least for Calvin Holloway.

As I watched, he unknotted the sash on his dressing gown and brushed the sides away. Then he slowly unbuttoned his fly, flared the front panel of his trousers, and pulled his shaft out. He was thick and long and in erection. Slowly stroking his cock, he said, "I wish to see you again--as in nature. Disrobe for me, please."

And so it seriously began. We had both known it was building to this. It had helped that he'd covered me before--in Raleigh. It was time for me to earn my promotion into this job and my keep.

"Pose, please. Entirely open and vulnerable. Don't try to hide anything from me."

I stood and slowly stripped my clothes off, standing there afterward, arms at my side, casting my eyes down demurely. It had been thus in Raleigh before he had devoured me.

"Beautiful. You are a gorgeous young man," he said, his voice low and guttural. "Put this on, please," he said. He brought forth a red satin slip from beside his chair and held it out to me. When I had slipped it over my head and smoothed it down my body, he murmured "There, even more beautiful. Come here."

I went to him. He spread his knees, and I came in close between them. He slid the straps of the slip down so that the bodice fell off my pecs. Nuzzling his face into my chest, he took my nipples in his teeth, one after the other, and suckled them, making little mewing sounds. Instinctively knowing what he wanted, I arched my back a bit, threw my arms around his neck, and moaned in low tones while he worked my nips with his teeth. After a few minutes, he drew back, and in a husking voice, said, "Kneel to me."

I knew I was somewhat androgenous in looks and that my body was willowy, and I knew how to cross into taking on feminine demeanor when that was what men wanted and was how I was dressed. This obviously had been what brought me to Holloway's attention to begin with. And in that time period, that was a popular fetish among powerful men in business in the United States.

I knew he wanted more than that--more than just androgenous looks and demeanor and to suckle my nipples. I knew he was going to have whatever he wanted and I might as well anticipate what that was and provide it. I went down on my knees between his spread thighs. I took his cock in my throat and gave him head. As I sucked, he reached under with both hands and resumed working my nipples between his fingers. I didn't take him to an ejaculation, though. At length, after disengaging from my puffed-up nipples and running his hands over my body underneath the slip as I sucked his cock, his hands moving to concentrate on palming, squeezing, and separating my buttocks cheeks and seeking and find my hole. When he'd had enough of this, he murmured, "Turn for me. Put your ankles on my shoulders."

This was it. He wasn't just a tit man. He was a cock-in-hole man as well.

I did as he bade, pressing my cheek and my chest to the carpet in front of his chair, my arms bent and my palms flat on the carpet to hold myself steady. He grasped and raised my ankles onto his shoulders, and I moaned and groaned for him as he slid the hem of the slip up to my waist, squeezed and slapped my exposed buttocks repeatedly, and then moved to working my hole and my cock and balls with his fingers. I scrabbled at the carpet as he gripped my waist between his hands and pulled my buttocks up to his face, which was buried in my crack, his lips and tongue going to my hole. Still gripping my waist with one hand, he grasped my cock between my legs with his other hand, and while I whimpered and moaned, he ate my ass out and stroked my cock, taking me to an ejaculation.

When I had come, he pushed my legs off his shoulders and brought me down into his lap, facing away from him. He positioned my hole at the mushroom cap of his cock, and slowly brought my passage down onto his erection.

I murmured my surrender to him in a tremulous, high-register voice. "Be good to me, Daddy," I whispered, my voice belabored by the effort to take his shaft inside me.

"Fuck yourself on it," he murmured, and, getting my feet onto the chair cushion on either side of his hips, with him holding my waist between his hands, I used the leverage of my legs to rise and fall on his shaft. He was hard as steel inside me, filling and stretching.

Before he came, he took control, turning me on the cock without losing purchase so that I was facing him, my ankles again on his shoulders and my torso streaming down to the carpet in front of him, my arms extending out in an "I am completely yours" cruciform position, with my back arched and cheek to the carpet. He pulled me on and off his cock with a grip on my waist under the hem of the slip, and, with a grunt and a tensing and one, then a second, and finally a third jerk, he breeded me.

He was a strong, muscular man. He had no trouble manipulating my smaller body at will, and I made no effort to deny him anything. He was now my fully in-control master.

None of this came as a surprise to me. When I had met him in Raleigh when he'd been there to approve my appointment, he had taken me to his hotel room and vigorously fucked me through the night, holding me in front of him, penetrating from in back. I had already experienced his cross-dressing and tit play fetishes. He had provided a black-lace corset, with a padded bra then for me to wear to enhance his arousal while he fucked me. I was fully prepared for the use of sexy women's clothing to happen this night as well, and, in that, I was correct.

"Come," he said as he released me and I slithered to the floor. "Let us go up to bed."

The sound of our steps on the stairs to the upper level and to a guest room--he said we would not sleep in the bed he shared with his wife--echoed throughout the house, giving the distinct impression that we were the only ones in the cavernous building. Awaiting us on the bed was a black-lace corset--probably the same one he had provided in the Raleigh hotel--which he had me put on, and he fucked me again on the bed.

It may not have been the case, though, that we were alone in the house at night or that Holloway's men servants weren't fully aware of his sexual fetish. The next morning, we were awakened by the arrival of a groom who brought in coffee and pastries, with both Holloway and me naked in bed together, under the sheets, and his trousers and dressing gown and both the red silk slip and black corset on the floor below the bed, topped by the riding crop Holloway had used when he bent me over the foot of the bed, beat me, and mounted and rode me like I was his mare. Holloway was on his back, and I was on my side, turned toward him, one of my arms across his chest. I was suckling one of Holloway's nipples, and he was mewing his pleasure. The groom just moved about the room opening the draperies and not showing any indication of surprise that Holloway had a new young man in bed.

It wasn't long before I realized that I had replaced Harry in that role as well. The groom was still in the room when Holloway rolled over on top of me, between my legs, grasped my wrists to hold my arms over my head, positioned his cock and penetrated and started fucking me in the missionary position. He was a virile and vigorous man. He had fucked me through the night, breeding me again and again. Although they were doing so in Raleigh at the time, Holloway showed no interest in using what recently had become called rubbers even as the connection between syphilis and unprotected sex was becoming more realized.

He breeded me each time we coupled. Most men pulled out of me to release their seed. Not so with Cal Holloway. He always had me laid out under him, under his full control and looking into my eyes in triumph--and pumping me full of his cum, and usually do so as he was sucking on one of my nipples.

The groom stood at the foot of the bed and watched Holloway take me. Later the groom fucked me as well--and he, too, liked doing it with me wearing a slip or a corset. Holloway knew how to select his grooms. He clearly knew the groom was fucking me too, and I enjoyed the groom's cocking--he was young, handsome, muscular, and virile--so I just fell into my duties in this regard.

* * * *

I was a man of some means outside of my job. I didn't fully rely on the firm of Collins, Bagwell, and Holloway or even on Calvin Holloway individually for my keep, but Calvin Holloway clearly wanted me to be a kept man--his kept man. And I could not hide that Holloway's fetish aroused me and I wanted what he provided for me.