The Middleburg Riding Club

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.