The Middleburg Riding Club

by Habu

8 Aug 2022 2121 readers Score 9.1 (52 votes) PDF Mobi ePub Txt


I was surprised after I had turned onto Route 50 from 29 in Fairfax how dramatically the suburban sprawl from the nation’s capital turned into lush, rolling, rich rural estates countryside. I was headed west from Washington, D.C., toward my destination in Middleburg, up the Potomac River, some twenty miles parallel to the river. I’d been in Washington, working for Rhode Island senator Steve Standish for over a year, but I had not yet traveled from the capital in this direction. I wasn’t from this area. I was from Rhode Island too. My family connections had gotten me the job with Standish’s office. There had been an incident with a teacher at the college prep school I went to after high school and my family wanted me out of town—as much for the family’s reputation as to change my outlook on life. Little did they know they were thrusting me into the mouth of the lion.

No doubt what saved this area from a suburban sprawl of its own was money—old Virginia money and new political money. This was the Northern Virginia hunt, made famous in the late fifties and early sixties by the horse set surrounding President John F. Kennedy’s wife, Jackie. She came here to ride her horses, so all who were socially prominent in Washington came out here too to join those of the First Families of Virginia who already were riding their horses here and being gentlemen farmers on big, lush estates. Both forms of the wealthy stayed and used their clout to protect their playground from suburban sprawl long after Jackie O left.

I wasn’t on vacation in driving out here to the plush—I certainly assumed it was plush—Grayson Inn and Winery outside of Middleburg, although my posted schedule back at the office in the Russell building said I was—that I was spending the weekend in Richmond, in an entirely different southern direction from Washington altogether. This trip was hush, hush, but it did have everything to do with my job. I was the public affairs liaison for the senator. I was auditioning this weekend to become his deputy chief of staff. I was ambitious to work my way up, and I realized that I wasn’t the only one in the office who coveted that move up. I probably wasn’t the only one in the office who was willing to do what it would take to win the job either.

Audition. That, in fact, was what it was. It wasn’t a job interview. Senator Standish didn’t need that from me or any of the other guys—all guys. Standish didn’t keep more than the requisite number of female staffers around him, and none of them were brought into his inner sanctum. Steve Standish, tall, patrician, handsome, moneyed, and suave in his early fifties, was definitely a man’s man. This was an audition.

The man had fucked me on two occasions before—once in surprise in his office, with me bent over his desktop on my belly and the senator hooked up behind me, gripping my hips between his hands, and fucking me doggy style. He was a big-cocked man—quite vigorous and athletic. He also was cocky; as soon as he was able to ascertain that I would take his cock—that I wanted to keep my newly won job on his staff—he fucked me. The second time was soon after that when he tested just how far my loyalty went to him. While his wife was taking his daughter back up to their house in Newport to check out colleges for her, Standish had me rent a beach bungalow on Fenwick Island, New Jersey, for a weekend and he put me through my paces and checked out what I would do for him—again, to keep my job in his office. He fucked me repeatedly that weekend, in multiple positions, testing me on what I would take from him. I took it all.

He was also testing me on my loyalty and discretion. I met both tests. I had told nobody that the boss was screwing me and I never turned him down when he wanted to screw me.

I had done all that he wanted. Now he needed to fill the deputy chief of staff position and he was giving me an opportunity to fill it. Ostensibly, he was having a weekend at a horse-riding club he belonged to that was connected with the Grayson Inn and Winery where I was headed and I was vacationing in Richmond. We both knew what really was going down this weekend, though. I was going down for the senator—when and where he wanted me to.

I didn’t know what else I had to let him do to me sexually that I hadn’t let him do already. I’d take bondage and whipping and a taste of fisting—a bit of everything. The senator was always looking for new fetishes to heighten his arousal and release. I was naïve, though. I hadn’t, in fact, done it all.

I knew I was being a slut, but I’d do whatever I had to to get this job. I knew that I had to do well just to keep the job I had. He was a good-looking man. I wasn’t promiscuous, but I knew I had a good body and looked good in it. I might as well use it, as needed, while I still could attract men—and women, if I really had to. I took what men did to me. I endured with a smile, made all of the right encouraging sounds, and didn’t complain.

I drove through Middleburg, which was sort of Disneyland for the rich country folk, as far as I could see. Not too far from after leaving there, I turned between two stone horses on brick pillars that broke a mile-long run of freshly painted white fencing, with green lawn and sleek grazing horses behind it, and drove an oak-lined crushed-stone drive up to a southern colonial building that sprawled out too much in two-story splendor to be just a house. I had arrived at the Grayson Inn. It had been constructed to blend in with the stately plantation houses dotted around on the manicured estates here in the foothills of the near-distant northern end of the Blue Ridge Mountains, but it obviously was newer construction than the genuine antebellum mansions it emulated. I pulled my Mustang convertible up to an imposing entrance in the forecourt of the building. The longer-term parking area apparently was located someplace else hidden from view. The drive I had turned off to enter the forecourt continued around the east end of the inn beyond a sign saying that the winery was somewhere farther down that road.

A valet and bellboy met me at the car; took my bag and suit bag out of the trunk for me, with the valet saying he’d move my car when check-in was completed; and I followed the bellboy into the inn. The lobby was understated elegance. I saw a dining room through double, glass-paned doors straight ahead and a bar, from whence soft piano music was floating, off to the right. A handsome young man in what must be the inn’s official uniform—because the valet and bellboy, both also young, handsome men, were wearing a version of it as well—stood behind the reception desk and smiled a broad, welcoming smile at me.

“Checking in?” he asked.

“Yes, the reservation should be in my name, Trent Chandler, I said.” I was damn sure it wouldn’t be in the senator’s name, although he was footing the bill for this tryst. I hadn’t made the reservation myself, though. I was equally sure he hadn’t made it for me in his name. He was much too careful to leave any records connecting him with his young men in this way.

The door to an office behind the reception desk opened and a real hunk of a man, maybe in his late thirties, in scruffy clothes, but filling them out to perfection, appeared in the doorway, leaned up against the doorframe casually, and gave me what I took to be a knowing look—a friendly smile but one that, at the same time, was an “eat you up” smile. I was prone to assessing all men I saw or met for their potential topping value, and this man made the top 10 percent. I blushed, as he seemed instantly to know who I was and what I was there for. His workman’s clothes and open and honest “who the shit cares?” look were what seemed out of place and off color here, not me, who was here to be fucked to win a job. I was a congressional white-collar guy, but that only meant I was even more attracted to the blue-collar stud type.

“Ah, Mr. Chandler,” the receptionist said. “You are booked at the riding club’s building. That’s Grayson Hall. You’ll find it down the road, past the winery. Sean,” he said, turning his head to the bellhop, “Please put Mr. Chandler’s luggage back in his car.” Turning back to me, he said, “You can check in at Grayson Hall. We’ll keep no records here. They will take good care of you there. Enjoy your stay with us.”

I didn’t have any trouble linking up the “we’ll keep no records here” with them taking good care of me—and the senator, I was sure. Had the receptionist’s expression changed a bit? Was he giving me a more scrutinizing look now, with just a hint of smugness and condescension, which belied the added obsequiousness that had come into his voice inflection? Surely not, but when I glanced at the man lounging in the office doorway, I saw a bit of smirk in his face too. He nodded at me, turned, and went back in the office.

Had that been a “I can have you if I want” look in the man’s eyes? If so, I couldn’t naysay him from the effect he had on me from this brief encounter. I don’t know how he could tell, though—it wouldn’t just because a senator was screwing me that he should have been able to think he could as well.

My car hadn’t been moved. Five minutes and it was like I’d never stepped foot in the Grayson Inn at all. Somehow, I got the impression that that was the way it had been meant to be. I drove further into the property and into more hilly terrain. I passed the winery, which looked like quite an operation. It was supported by extensive grape vine fields in this section of the estate. Past that, I drove between two hills and there, in what surely was Grayson Hall, stood what quite obviously had been the original plantation house, in red brick, with ivory pillars supporting two stories of front porch. It wasn’t as big as the inn, but it certainly was big enough in its own right to deserve a “Wow,” and it dominated the landscape. To the west of the house was a terrace with a swimming pool and to the east was a tennis court. Beyond the house were stables, a riding ring, and, in the near distance, a helipad—everything a big daddy like Rhode Island Senator Steve Standish could want.

I passed a parking area, bordered and shielded by mature boxwood hedges, and rolled into a circular drive running past the front of the house. I recognized Standish’s Jaguar, but, unfortunately, I recognized a yellow Porsche Boxster in the lot as well. Again, a car valet and bellhop came out of the entrance as I rolled up to it. The valet, who was every bit as young and handsome as his counterpart at the inn, said, “Welcome, Mr. Chandler. You’ve found the place.” He took my car keys and this time didn’t wait to see if I was going to pass the check-in test. He drove the car off as I entered the building. It wasn’t lost on me that he knew my name—that he knew I was arriving here.

The layout of the public area was somewhat the same as at the inn, if more elegant and more directly masculine—dining room straight ahead, reception desk to the left, and bar to the right. No one was at the reception desk. The bellhop took my luggage past a sweeping staircase to an elevator behind, obviously already knowing where to take them. Every evidence was showing here that discreetness was of the essence. There would be no record that I’d ever been here. I wouldn’t be receiving a bill—and no one else would in the name of this establishment either. No one was stationed at the small reception desk.

A familiar voice floated out from the bar. “We’re in here, Trent. Come join us.” Senator Standish, he who was to be obeyed, had called me to duty. I entered the bar, the word “we” not having been lost on me. As I feared, sitting with the senator was Boyd Bradley, Standish’s legislative liaison—yet another young man who coveted the job of deputy chief of staff in Standish’s congressional office and the owner of the Porsche Boxster in the parking lot.

I, quite apparently, wasn’t the only one who was going to be auditioning this weekend.

Standish and Bradley weren’t the only men in the bar, or even at their table. Three middle-aged, prosperous-looking men, two of them in riding togs, were in the bar. One of them was talking rather intimately with a young blond guy who couldn’t be more than twenty and was in horse-riding gear as well, but not as expensive or elegant as the older man was wearing. He looked more as if he actually worked with the horses. The man he was drinking with was touching him with his hands and leaning into him. All three of the older men looked to the entrance as I walked into the bar, though, and I got the impression I was being assessed for use.

This obviously was a club for rich men who rode more than horses. And the senator was a member. I was beginning to get an inkling that more than Standish would be involved in this auditioning process—that men in the club procured young men for each other. Was part of this auditioning process who I’d let fuck me who Standish wanted a favor from—or would Standish be adding a new fetish to his preferences of voyeur? Did he want to watch while another man screwed me?

Seeing the added figure at Standish’s table brought both of those possibilities to mind. The man sitting at the table with the senator and Boyd was much like the other three men in the bar—middle-aged, rich looking, just not the most handsome man in the world, a bit pudgy, wearing riding togs, holding a riding crop, and looking as much a part of this place as the other three men were. He was ogling me from the moment I entered the bar—openly, without embarrassment.

He wanted me. Well, if that’s what Standish wanted, I guess the man could have me.

Senator Standish introduced us. “Trent, this is Chaz, a good friend and a member of the riding club here. He’s going to join in our entertainment for the weekend.”

I wasn’t born tomorrow. I knew what that meant. If Standish was going to ride me this weekend, this Chaz dude was going have leave to do so as well—and maybe any of the other club members who showed up this weekend and wanted to hump me, as well. So, that was more in the way of sexual favors I could surrender to Standish than I already had.

Shit. I sat down at the table and looked at Chaz, giving him the requisite smile pf “yes” to the question not yet asked. He smiled back, rather lustfully, I thought, and touched my forearm with his fingers, leaving them there, playing with the swirls of short hairs on my arm. Could I really let this man fuck me—for strong consideration for the deputy chief of staff position?

I really did want that job. There was no question pending here.

* * * *

“You have ridden horses before, haven’t you, Trent?”

“Yes, senator, I have,” I responded. Chaz was still ogling me, and were those his fingers brushing my thigh? Yes, they were. Shall I let them? Yes, I will. In fact, when he does it again, I’ll take the hand and move it higher on my thigh. I know what’s at stake here and have already decided how far I will go with it. Am I a slut for ambition? Yes, I am.

“Chaz here is riding this afternoon. I suggested that you might want to ride with him.”

And then ride his cock, I’m sure. It’s what I thought but not what I said.

“And Boyd?” I asked. If Boyd went with us, he couldn’t be here working on Senator Standish in my absence.

“Boyd has never been on a horse. He’ll be here with me. We have a few issues to work on concerning the pharmaceuticals legislation Chaz is helping with. Chaz works in pharmaceuticals. He’s been a great help to us.”

As the pharmaceutical industry has been with your bank account, I knew.

One or two up on Boyd was that? Chaz needs rewarded. Boyd doesn’t ride and Chaz wants to ride, so, since I ride, I can be more valuable to Standish by riding Chaz’s dick. “Pharmaceuticals? How interesting,” I said.

I fluttered my eyelashes at Chaz and the touch on my thigh was rewarded to my taking his hand and moving it higher. The touch turned into a grip. I just smiled at him. But I wasn’t going to be that easy.

“I didn’t bring any riding clothes, I’m afraid,” I said.

“The club keeps several sets for their members’ guests. I’m sure we’ll be able to suit you up properly.” The senator obviously wanted this to happen.

“And a horse?”

Was Chaz a horse, I wondered. He didn’t look promising, but sometimes unfit-looking men were hung.

“You can go with Chaz to the stables right after lunch. The club has a string of horses available for its members’ use.”

As we approached the stables, Chaz being so sure of himself that he was guiding me along with a hand on my butt, the same god-like man I’d seen lounging in the office door at the inn building was leaving the area in a golf cart. For the briefest moment our eyes met, he smiled—or was that a smirk?—tipped his cowboy hat to us, and was gone. He certainly seemed to be everywhere in this complex.

I actually enjoyed the ride—the rides; both the horse ride and the ride on Chaz’s cock. The Virginia countryside in this area was gorgeous and, after the city, the air was fresh. In addition to the horse ride, I enjoyed the fuck that inevitably happened in a stand of trees by a brook where he came down off the horses to rest them for a few minutes—or that was the excuse for us stopping in that isolated spot.

A few minutes was all it took and it didn’t take long. Chaz, although experienced in this, was a quick shooter. He’d barely run his arm around my waist and turned me onto all fours after he’d come in for a kiss while we were sitting on the moss under a tree, until he had my borrowed riding pants and my own briefs down around my knees and he was climbing on top of me, thrusting inside, and giving me a bit of stretch before firing off. He was satisfied with the one, quick go, and I was fine with leaving it at that. I really like a thicker and longer cock and more pumping time, though. He hadn’t had to say anything to get his quick release from me. We had both understood was this was all about from the time we were with the senator in the bar.

The fuck obviously was all he wanted from me, because, saying he really needed to get back to Washington, he left me there, still in the set four-point stance, his seed oozing out of my ass, mounted up, and was gone. I rode for another twenty minutes before going back to the stables. My approach to the stables took me by the winery. The “he’s here/there/and everywhere” man was there, examining the grape vines next to the road when I was riding by. This time he hailed me down. He’d stripped off his shirt since the last time I saw him—he had the musculature of a god, with swirls of short, curly black hair around his pecs and descending in a line down to his beltline, with his jeans dipping so far that I thought it might touch the base of his cock and pubic hair curled up over the line of the waistband. He also was tatted and pierced, which surprised me. His nipples puffed up and were pierced with gold bars. There wasn’t an ounce of fat on his cut torso. A swirl of tattooing followed the curve of his left pec and moved over and down a bulging bicep. A sunburst tattoo centered on his naval. He obviously was a player. I ached to have him inside me.

“Enjoying your ride?” he asked.

“Very much so,” I answered.

“You were with Charles Langden. Did you lose him somewhere back there?”

“No, he came back before me.”

“Yes, I understand he comes quickly. As long as you’re here, would you like a tour of the winery?”

If he thought he’d slipped that little dig in without me noticing it, he was quite wrong. I know I blushed at his knowing comment. I would have retorted if what he said hadn’t been true—and if I minded being escorted around the estate for a while by this hunk. He must be the most valuable employee at Grayson’s to have his hand in all of the complex’s business. I’d already gathered that the riding club was nothing more than a glorified brothel for well-heeled men. I wondered if this man was involved in that operation as well.

“I’m Greg Grayson,” he said as he gave me a hand assisted in coming off the horse. “And you, I already know, are Trent Chandler, working for Senator Standish.”

I nearly swallowed my teeth. Not just an employee here—the owner of the Grayson Inn, or at least in the family.

The tour went very well and was more extensive that just following the grapes from the vine to inside the wine bottle. I showed that my expertise was in managing the process, and he seemed happy to adjust to emphasizing the financial and management aspects of the business, including distribution. As we walked, he guided me around with his strong, callused hands, sometimes on the butt, being familiar with me in ways that kept me hard during the tour. Was he going to fuck me? Yes, he was, if he wanted to.

“That’s our shortfall here, I’m afraid,” he said. “We have several complex operations going and not enough managerial expertise to handle it all. I’m more of a hands-on worker.”

He certainly could do the hands-on work with me, I was thinking. He was a hunk and a half. The working man’s clothes added to the arousal of the man. The woodsy smell of him and honest sweat were clanging my bell of desire. I loved the tats and the nipple bars were sending me into flights of fantasy, all of which resulted in him being on top of me and inside me.

“You seem to be well versed in the type of expertise we short of here. What is it you do for Senator Standish—I mean beside the obvious?”

“The obvious?” I asked. “I’m his public affairs chief, but my college education is in hospitality management.”

“That sounds like a fancy title for something we could use around here—managing a brothel.” He laughed.

My, were certainly were being open and honest here, weren’t we?

“Is that what the Middleburg Riding Club is—a brothel for rich men?” I asked.

“The senator brings young men out here for only one purpose. And he sends them out riding with men like Charles Langden for the same purpose. Let’s be straight about one thing. You are one of the senator’s boy toys, aren’t you? Your obvious service to him is taking his cock and any other cock he designates, isn’t it?”

“Yes, so what?” I said, sticking my chin out.

“No problem with me. And, yes, the riding club is a high-class brothel. Mostly it’s a bring your own partner at this point, but I’ve been thinking of putting a stable of young men in. Some of the young guys working already are available. Are they both good cocksmen—Standish and Langden?”

“Aren’t you making assumptions about what the man and I did on our ride?” I asked, suddenly not that wild about being taken for granted.

He laughed. “I was down by the stream before coming up to the winery. I saw the old man fucking you like a dog.”

Oh.

“He put you on the ground on all fours. You went down without objection. He mounted you and fucked you like a dog and you held for it. So, no I’m not making assumptions about what you did and would do. I know exactly what you’re doing here. You’re doing whore duty for the senator. Not much escapes me at Grayson’s. I manage it all. I probably know more about who Standish has signed up to fuck you here and when then you do.”

Oh, again. So that answered that about whether he knew what happened with the riding club men. He knew everything that happened here. “Good enough,” I said.

“What’s good enough?” he asked.

“The senator and that man down by the stream—they fucked me good enough.” I gave him a level, “so what?” look. I wasn’t going to be shamed by the man. I didn’t really care if he knew I laid down for men, if there were a chance that he was a man who fucked other men.

It appeared he was.

“Yes, I can be a whore,” I said. “There’s a better job at stake.”

“So, are you going to be a whore for me too? I quite fancy your type.”

There it was. And now that it was out in the open, it became not an “if” for me but a “when.” And I didn’t have to be in a hurry on that.

“I best get the horse back to the stable,” I said. “The senator will be expecting me at the hall.” I didn’t really fancy being taken as a whore—even by someone I was aching to take me. Being considered a sex partner was fine. But I’d have to think hard about being just a whore. It was a dismissive term.

“Not much a chance of the senator expecting you. By my schedule he’s fucking that other young guy in your office, Boyd Bradley. I gather the two of you are vying for the same job promotion. That’s quite convenient for good old Senator Standish.”

I didn’t answer, but I also didn’t move away from him. He was just too gorgeous to look at.

“It’s a beautiful day,” he continued. “It’s a day to revel in the vineyards. I have a blanket in the office, let’s say you take the horse back to the stables and return to the vineyard. By then I’d open us a couple of bottles of wine, found some glasses, and we could go out into the vineyard, between the rows, and get better acquainted.”

“The sounds like a plan. But I want you to know that I’m not a whore. I don’t do any of this for money.”

“Money, position . . . they are the same thing. I do it for pleasure. If you come with me, I’ll treat you like a whore. That’s how I like to take my men.”

“That’s good to know,” I said, as, at last, I signaled to the horse that it was time to go back to the stables.

Grayson was a master cocksman. He put me completely under his control. He was strong and knew exactly what to do to a man who had had a bottle of excellent wine. We both got naked, he devoted a fourth of a bottle of wine in pouring it over my chest and licking it up down to my cock, which he devoured while his fingers found, invaded, and stretched my channel. The stretch preparation was needed because he was hung like a bull.

He encircled my waist with a strong arm, and lifted my hips off the blanket, with my torso streaming back toward the ground. This put my pelvis in a perfect position for his entry as he hovered over me. He locked his eyes on mine to savor my expression of pain-passion-pleasure as he entered and spread me open and then fucked the shit out of me.

I cried out, “Oh, shit. Oh, fuck. Goddamn you’re huge. And the bead . . . the bead. It’s killing. Slow down. Take it slow.” He didn’t take it slow. He treated me like I was a seasoned whore. He took and took—whatever he wanted. It was glorious.

He relentless pressed in with the cock, moving into the very core of me, mastering me, killing me at the core. I had found he had a large gold bead pierced in his mushroom cap as I gave him head while we were moving into the fuck. It clicked against my teeth as I sucked him off and it amazingly, could be felt as it slid deep inside and then, when it was in the very quick of me, kissed and caressed my channel walls in its in-and-out motion. The muscles of my passage walls shimmered and rippled as the bead dragged across them.

Well into the stroking—the man could fuck forever—he changed our positions. He was sitting on the blanket, his knees drawn up and he held me, cantilevered out from the front of his body, my legs streaming back around his hips, his strong hands gripping my wrists, and my torso arced out from his chest.

“Dig your toes into the ground,” he barked. “Fuck yourself on it. Be my whore.”

I did as he commanded and, from the leverage of my feet, moved back and forth on the cock.

“The bead, the bead,” I gasped while panting. It was driving me crazy. “Come inside. Unload inside me,” I begged. The one crucial thing we had forgotten to bring into the rows of grape vines was a condom. Neither of us let that stop us.

“Be my little whore,” he growled.

And I was his little whore.

He did come deep inside me, blasting me once, twice, three times, before, with a sigh, he released my wrists and lowered his legs and I collapsed on him, lying there, gasping and panting and moaning.

“That was a good one,” he murmured. “We’ll rest and then give it another go.”

No that wasn’t a good one screamed through my brain. That was a great one—maybe the best I’d ever had.

He lifted my body, pulling me off his cock, turned me, and nuzzled my face into his crotch. I opened my mouth to the now-flaccid, but still formidable shaft, and we cooled down to the sound of the gold bead clicking against my teeth.

Afterward we polished off another bottle of wine while discussing the operations of the inn, winery, and brothel, and then he put me on all fours, mounted me, and rode me hard and long.

“I liked watching the old man take you this way,” he said as he moved me into position and mounted me. I liked him doing it that way more than I liked the old man’s doggy fuck. He certainly rode me longer.

If he’d asked me again whether Chaz was a good cocksman, I would have had to say that, compared to him, Chaz was shit at fucking a man doggy style.

* * * *

Our rooms at the hall were strung out with Boyd’s room on one side of Standish’s and mine on the other, all conveniently with shared interior doors as well as individual doors to the hallway. When I returned to my room, the door into the senator’s was fully open. He was standing at a window just inside the door, wearing only an open silk robe and with a cigarette in one hand and a glass of amber liquid—he did like his double malts—in the other. He was leaning into the window, watching something out on the lawn, but I was sure he knew I returned and was watching him.

The senator had a great body for a man his age, and I knew, from experience that he was virile—that he could get it up quickly on reload and keep it up. He was half hard now.

Beyond him, I had a full view of his queen-sized bed. The sheets were tussled, and Boyd Bradley was stretched out on the mattress, face toward me, an arm hanging off the side of the bed, a study in sheer exhaustion. His eyes were open but glazed over. I wasn’t surprised. I well knew that Standish could do that to a young man. A couple of pillows were under his belly, raising and tilting his hips. His hole was gaping, dripping Standish’s lust. And there was something else on the bed—a horse-cock-sized-and shaped dildo. Brad had been worked over with the daddy of all dildos.

Standish turned his face toward me and smiled. I snorted, turned away from him, and went into the bathroom to shower the glorious sex with Greg Grayson off my body. When I came out of the bathroom, with just a towel around my waist, I went to where I could see into Standish’s room. He was on the bed now, naked, his silk robe in a puddle by the bed. Boyd was in the same position I had last seen him. Standish was mounted on his hips, the palms of his hands pressed into the younger man’s shoulder blades. The senator’s pelvis was rising and falling as he gave the younger man deep fuck. Boyd’s eyes were flashing pleasure now—and perhaps a slight hint of “see what I’m giving him and you aren’t” look at me. The senator’s face was turned toward me too, and he was showing a smile of deep satisfaction as he pumped the younger man with long, deep strokes.

As I was turning from the door, I saw Standish pull out of Boyd and pick up the dildo. I walked away from the door between our rooms. I wasn’t about to be cowed by this or to let Boyd command the field. I pulled my towel away and let it drop on the floor. Then I sat on the side of my bed, directly facing the open door into Standish’s room, grasped my cock and stroked myself off in the same cadence of Standish’s stroking of the dildo in Boyd’s ass.

I timed my release to coincide with Boyd’s climax. It wasn’t Standish and Bradley I was thinking about, though, it was Greg Grayson, fucking me like I was a whore—and with a cock that was every bit as nice as the dildo Standish was using on Boyd.

* * * *

The dining room of Grayson Hall was not large, but it easily accommodated the men who were there. Standish, Boyd, and I were seated at a table for four. Three other tables, set for two, were occupied. I recognized two of the older men at the other tables, but hid the recognition. I was surprised they were members of the club, especially as one of them was wearing a clerical collar, but I wasn’t surprised that they had the wherewithal and political clout to be members. The third one looking like a South American senior diplomat I vaguely remember seeing before, and probably was. Seeing who was seated with them brought back a comment Greg Grayson had made earlier to me about the staff. The two car valets from the inn and the hall who I’d seen earlier and the bellhop from the inn were seated with the other men in the dining room. The young men were expensively and tastefully dressed. I was sure that the older men they were dining with would enjoy unwrapping and fucking them upstairs after dinner. They seemed to be quite comfortable with the men. So, I thought, Grayson already has made a start on providing male whores in this brothel.

Grayson was there too, floating through from time to time, supervising everything. The transformation in his appearance was astonishing. He had moved from husky field hand to tattooed and pierced satanic stud having his way with whomever he wanted to spike, to this, tonight. He was elegantly dressed in a tuxedo. He was gorgeous, and he moved like the maître d’ of a five-star restaurant.

Boyd was watching Grayson move whenever he showed up and there was little question that he wanted the man. I felt a twinge of possessiveness. I didn’t go anywhere with it, though, because our fourth was entering the dining room.

“This is Horace,” Standish said, all of us standing for the new arrival. “He works in defense contracting, and his firm is very generous to my reelection funding.” Standish was speaking directly to me. I knew what he was saying. I was charming—and suggestive—to Horace during dinner. He was smitten and touchy-feely. Boyd disappeared after the dessert course was served, and Standish pulled away from the table soon afterward, leaving just Horace and me at the table. I knew what was expected of me.

After coffee and cognac, I rose from the table, as did Horace, and without further discussion, we left the dining room together and he followed me up the stairs to the bedrooms. He placed a hand possessively on my buttocks as we mounted the stairs. I knew it wouldn’t be long before he would mount me.

As we approached the stairs, I could see down the side hall, in the shadows, that Greg Grayson had Boyd plastered up against the wall. Boyd’s trousers and briefs were puddled on the ground and his legs were hooked on Grayson’s hips. Grayson’s jacket was off and his tux shirt was flapping open, exposing his magnificent chest. Boyd was sucking on one of his nipple bars and Grayson was fucking Boyd in long, deep strokes.

A jolt of jealousy flashed through my body, but I didn’t have time for that. I was auditioning for a job. At least if, and while, Boyd was with Grayson, he wasn’t contributing to his campaign for Standish’s position opening. I was on a relevant mission now—to be a whore for Standish, to keep that defense contractor funding flowing into his campaign chest. And there was no use getting possessive of Greg Grayson. He was a master stud; he’d do as he pleased and all of his men could just lump it if they wanted to feel that gold bead destroying them in the core. And once you’d been fucked by Greg Grayson, you were his. Boyd was as much his now as he was Standish’s toy.

The door to Standish’s room was open but his room was dark. From the moving glow of the lit point of a cigar, though, I could tell that Standish would be sitting on the side of his bed, watching Horace fuck me on my bed. Standish like to watch almost as much as he liked to fuck.

Horace was a big, fat man, a virtual walrus, and, as a sex partner, he was better to take in the dark than the light, but he had a cock and an erection and he knew what to do with it. He fucked me missionary style on the bed, thankfully supporting most of his weight on his knees as he knelt between my open thighs, held my legs spread and raised with hand grips on my ankles, and thrust hard and vigorously to a half-way decent gush of cum into the bulb of his condom.

He was good with just the one time and then was dressed and gone, lingering a bit to enjoy the view of me, naked on my back on the bed, looking both sexy, I’m sure, and exhausted. I, in fact, was tired, but not from Horace’s efforts, as skillful as they were, somehow managing to fuck me deep and at length despite the rolls of fat. But it had been a long day and evening in the giving sex department. I truly earned the title of whore on this day.

But my sex day wasn’t over.

When the door to the corridor clicked shut in the wake of Horace, the light came on in Standish’s room. He was reclining on his back, a one-quarter turn to me. He was naked, stroking his erection, and looking, expectantly at me.

I sighed, rose from my bed, and moved, with a strut, into his room. I saw that the door to Boyd’s room was shut—and, I hope, locked. My auditioning wasn’t over, but, what Standish didn’t know was that the auditioning didn’t mean fuck to me anymore.

I climbed up on the bed, turning the senator onto his back and pressing his legs between my knees. I lowered my face, brushed his hand away from his erection, took his shaft in my mouth, and gave him deep-throated attention. He moaned, lying back on the bed, and taking my head in his hands, holding my head close into his crotch, enjoying the blow job, and running his fingers through the golden curls on my head. He struggled a bit with me when he realized I was going to take him to climax with my mouth, but he eventually gave up and emitted a long, deep groan as he released his seed.

I licked and nibbled up his body, moving up to where I was saddled on his chest, taking my time because he needed to recover and engorge again. My own erection pressed at his lips and he took me in and sucked me to a release. He was hard again after this, and I moved into a cowboy position, facing him, lowered my channel on his shaft, and, while palming his pecs as I’d seen him do with Boyd earlier in the day, I rose and fell on his cock, giving him another release.

As I rode Standish’s cock, I heard the dreaded sounds coming from the room next door—Boyd’s room.

“God, no, not so fast. Give me time. Shit! Fuck! The cock bead. You’re killin’ me. Oh, you big, beautiful fucker. FUCK. Yes! Fuck me! Fuck me hard. Treat me like a slut! Shit, that bed in the bulb! Shit. Fuck, fuck, FUCK!” The mouthing off subsided into groans and grunts and the sound of the headboard on the bed next door rhythmically bouncing off the back wall.

I had no doubt that Boyd and Greg Grayson had moved from the downstairs hall to Boyd’s room and that Greg was getting whatever he wanted again. I could be jealous, but I wasn’t going to change Grayson.

Standish did voice a “What the hell is that?” but I soon had him concentrating and maintaining his own thrust cadence.

We then stretched out against each other, sighing and panting low, continuing to fondle each other with our hands. I had every reason to believe that I could bring him to another erection. I was working at it with my hands and he was letting me.

“I want you to take on the deputy chief of staff duties when we get back to Washington,” he whispered into my ear as a stroked him with my hand.

“You’re offering me the job?” I asked. I was surprised that it had been this easy.

“Yes, there really was no question of it. I just needed you to help me pin down some obligations this weekend.”

Just pinning down some obligations? Was this what I was supposed to do for him in the new job—for as long as I was desirable to men and then he’d dump me for someone younger to pimp for favors? I didn’t need to dwell on this, though. I’d already made up my mind.

“Thanks, but no thanks,” I said. “I already have another job.”

He started to say something, but I thumped his erection with the side of my hand, which gave him some pain to think about first, rolled off the bed, went back into my room, shut the connecting door, and threw the lock from my side.

I didn’t tell him I had accepted the position of financial manager at the Grayson Inn and Winery from Greg Grayson earlier in the day. As a member of the Middleburg Riding Club based at the Grayson estate, he would find out for himself soon enough.

I had no illusions about the job with Grayson. I would also be in his stable of rent-boys, but as long as he fucked me regularly, I didn’t care.

* * * *

Late in the night, I heard the lock turn in a door. I turned my head, having enough light entering the room to discern that it wasn’t the connecting door to Standish’s room. The lock from my side had held. It was the door out to the corridor. I’d locked that too, but now the door was open, the form of a man was standing in the doorway. Of course. Greg Grayson had the keys to all of the doors. We were all at his beck and call.

Three strides and he was on the bed, on top of me, covering me with his hands and his mouth, preparing me for his desire and his need. He fucked me hard, brutally, cruelly, like I was his whore. And I was his whore. I took it all, gave him all, glorified in having it ripped out of me, that gold bead in his cock head destroying me yet again in the core.

“Fuck! SHIT! That bead! Yessss!”

Later, as we lay there, me in his arms, cooling down, he asked, “Did you tell Standish you were leaving him?”

“Yes.”

“Did you tell him it was to do to work here?”

“No. He’ll figure that out on his own.”

“I’m hiring Boyd too—to maintain liaison with the members of the riding club.”

“I’m not surprised.” And I wasn’t surprised. I wasn’t thrilled, but I’d live with it. Greg Grayson was not the type of master stud who could be pinned down to one man. The trick was to continue being one of his men. I chuckled.

“What? What’s funny?”

“On nothing,” I answered. But it was funny—that Senator Standish’s little scheme of an auditioning weekend had lost him both of his candidates.

by Habu

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Copyright 2024