Rising to The Bluff

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Ambitious Scott accepts a Labor Day Weekend invite.
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KeithD
KeithD
1,305 Followers

Scott Monroe reeled out of the summerhouse at the back of the mansion property on Edgehill Road in the exclusive Westover Hills section of Wilmington, Delaware. Behind him, still reclining on a bench nailed to the wall around the inner rail of the summerhouse, lay Lani Lamotte, tennis skirt bunched up around her waist, panties on the wooden boards of the structure's floor, Scott's cum dribbling out of her exposed cunt. Her husky laughter followed him out onto the lawn.

Tennis shirt in hand, he was fighting to zip up his tennis shorts, confused on what direction to go in to get to his old Mustang convertible. The grounds of the Lamotte mansion, Daddy Lamotte being one of the hundreds of bank vice presidents in one of the downtown corporate financial headquarters havens, were extensive, with spreads of manicured tree lines here and there. No one could have seen Scott fucking Lani unless they'd come out to the summerhouse—although it was more like Lani fucking Scott—from the house.

Later, in trepidation, he called her from his mother's much more modest Edgemoor Hills working-class row house across the city, near the banks of the Delaware River. He'd been mooning over Lani, yes, and he thought she'd egged him on, but he hadn't meant it to go that far—at least not this fast. When push came to shove, Lani started it and Lani carried through with it.

He hadn't even thought to have a condom on him. She didn't seem to care or to offer him an out for not being prepared. All he knew now was that he'd better try to smooth it over or his ass was fried. He'd worked to get in good with what they called the Gang of Six, but what could happen now was that she could claim he'd raped her and there was no winning in this town against the banker class. All of those in the Gang of Six were in the banker class. Getting in good with them would have been a move of several rungs up the class ladder for him.

"My, you're a big boy, aren't you?" Lani cooed when she answered the phone. "Anyone tell you how big cocked you were?"

Yes, as a matter of fact they had. The last one would have been quite a shock to Lani, if he told her who it was, though. It had been her own boyfriend, Chad Harlan, another guy from a Wilmington banking family. Scott didn't have all that much sexual experience, but he was still on the fence in that regard—he'd fucked or been fucked by as many guys as he had fucked gals.

"I'm so sorry, Lani," he said. "This is serious, I know. I just got carried away."

"You sure did, honey. You did me royally."

"Then you aren't—?"

"Labor Day weekend's coming up," he said, cutting him off. "We're gathering at our cottage on the Elk River for one last fling after our summer jobs are over. We'd like you to come."

"The others. They don't—?"

"We'd all like you to come, Scott. We already discussed it. It will be quite casual. Cooking out, swimming in the river, making out, maybe smoking a little of something. You're OK with that, Scott, aren't you? You're not going to go prude on us, are you?"

"Uh, no, of course not. I mean, sure I'll come."

"Good. I'll text you the directions." And, with that, she clicked off.

It was almost a letdown—not what she said. She obviously was fine with the fuck and getting an invitation to party with the Gang of Six was beyond anything he'd hoped for. But it was all so matter-of-fact with Lani—like it had been no big deal for them to fuck. Everything seemed to be so much different at the Gang of Six's social level.

It had been Chad Harlan who had brought Scott to the edge of the Gang of Six circle, after they'd gone out drinking one night and wound up fucking in the back of Chad's BMW convertible, which hadn't been easy as they both were tall, muscular guys. It had been a flip-flop in which Chad had first ridden Scott's cock, with Scott, nearly drunk on his tail, but not having any trouble getting it up for the hunky Chad, reclining in the backseat and Chad on top of him, riding him in a cowboy. Then it had been Chad, knees pushing up Scott's buttocks and Scott's ankles on Chad's shoulder, while the big blond fucked the other, nearly as big, blond.

Scott already knew the other six by this time. Scott, his father gone and his mother working in a Penny Hill grocery store and living off his father's veteran's pension benefits, had worked hard to learn a bankable skill. He was a talented artist, and that was his major at college, but as far as bringing the bacon home and paying for college, which his mother's finances meant he had to cover himself, he was an excellent tennis player. He'd gone from the tennis team at the Mount Pleasant public high school and state champion on to an athletic scholarship at the University of Delaware. His continued tennis success there had landed him a summer job between his freshman and sophomore year at UD at the tennis complex at the Dupont Country Club, which included a tennis academy. All of that would end for the summer on the Labor Day weekend, and everyone would disperse again. The Gang of Six had been together since high school, though, and most of them went to colleges near each other. He didn't think they'd be dispersing.

The members of the Gang of Six, Lani and Chad, Trevor Price and Rachel Bowers, and Rice Oliver and Gretchen Harrison—all in Wilmington banking families and all graduates together the year before at the exclusive private Tower Hill school—all had jobs at the Dupont Country Club tennis complex that year too. They were a close-knit group, all going to more exclusive colleges than Scott did, all in a totally different world from his. Lani was at Bryn Mawr in nearby Philadelphia; Chad at Penn State; Trevor at Yale; Rachel at Arcadia University, northwest of Philly; and the inseparable Rick and Gretchen were at Haverford College, also in Philadelphia, together.

Scott, the best tennis player of the lot, but with the most junior job at the club, had ached to be accepted into their group. He'd been on the edge of it for a few weeks now, with Chad having teasingly brought him to the edge after they'd fucked—for the second time, to mark that the first wasn't a one-off drunken accident. The invitation to a long weekend with the Gang of Six at the river cottage of Lani's family marked his acceptance, he was sure. Looking at the directions, he saw that the cottage was named The Bluff. So, he was rising to The Bluff just as the summer was ending.

* * * *

Scott's goal in his old—not classic, just old and in chugalong condition—Mustang was Old Field Point, where the Elk River entered the top of the Chesapeake Bay. To reach it from Wilmington, he drove south on I-95 to the town of Elkton, Maryland, and down the peninsula between the Northeast and Elk Rivers.

He didn't know what to expect from a "cottage" on the river and why it was named The Bluff. He wasn't any more sure when he traversed Old Field Point Circle and came up beside a long one-and-a-half-story building on his left. The water was off to his right somewhere, but he couldn't see it for the foliage. The building on the left was interesting, some sort of long building with gray-brown wooden shingle siding and with its upper story only half a story in height before the forest-green wooden shingles of the roof started. He couldn't see a door into the building on the road side but after sitting and idling for a few minutes, he saw that a driveway went around the far end. This didn't really look like a "cottage" to him. It was too large for that.

He drove around the side of the building and landed in an asphalted parking area large enough to park a small army of cars, which it now was accommodating. Beyond that was a fenced tennis court. Pulling around to the other side of the building he now saw that it was a five-car garage. The half story above that was fantastic. On this side of the building a wide dormer jutted out from the slope of the roof and in the wall of this was a large, stained glass window.

From there, Scott's gaze was brought back down to earth by a metallic sound. An old, black Mercedes stretch sedan was half in and half out the farthest bay, its nose pointed out and its hood open. A light-brown, muscular man's torso was bending over the raised hood, the arms and head swallowed up in the cavern of the car's engine compartment. The legs were encased with old, worn jeans, the waist pulled down to the top of the man's crack. As Scott rounded the side of the building, the man unfolded himself from under the hood and raised a wrench in greeting.

The man was gorgeous. He was in his late twenties or early thirties. His body was slender but hard, well-muscled. His color was a golden brown—a deeper tone than tanning would provide, but not a deep chocolate. The dark hair and dreadlocks, though, identified him as likely at least half black. His facial features, though, were more European and achingly handsome. He showed Scott a friendly smile when the young man parked the Mustang in line with the other, expensive sports cars parked on the lot and walked toward the Mercedes.

"You must be the last of the lot," the man said, wiping his hand on a rag and offering his hand. His jeans were hanging so low on a narrow waist and hips that Scott wondered what was keeping them from falling to his ankles. His thought was that he wished they would, as the man was gorgeous. Scott immediately was smitten with him. "I'm Jack," the man said. "Jack Green. The caretaker. Do you need help with your bag?"

"Hi. I'm Scott Monroe. From Wilmington," Scott answered.

"Yes, I figured all of you young people were coming down from Wilmington to party Labor Day away. Your bag?"

"Oh, no. I can manage. The others upstairs?" Scott asked, look up at what was above the garage floor.

Green laughed. "No, this isn't the house. The house is across the road, above the river. This is just the garage. My apartment is what's upstairs. Go back around to the other side and you should see an arbor over a path. That goes to the cottage."

As he was saying this, a woman, maybe in her thirties, dark haired, buxom but otherwise slender, and quite strikingly good looking came out of the door at one edge of the garage building that must have been where the stairs went up to Green's apartment.

"Oh, you're awake, Shonda," Green said. She walked over to him gave him a peck on the lips and wove an arm in with his as he was leaning, looking all James Dean sexy, into the fender of the Mercedes. "This is Shonda Spruce, Scott. It's Scott isn't it?" And when Scott nodded, the caretaker continued. "She does for the Lamottes when they're in residence. Cooks for them. Other times she keeps the place from being buried in dust. You going over to the house, Shonda?"

"Yes," she answered, giving Scott a shy but interested look. "There's work to be started over there."

"Maybe you can show Scott the way then—unless you need help with your bag. Then I'll take you over." He was looking at Scott and smiling.

Feeling slightly vulnerable and perhaps being gauged as from the Lamotte's class and wanting services that he could easily manage himself, Scott quickly said, "No, thanks, I can handle my bag myself." He was in a quandary. He wanted to be in the Gang of Six's class, but he didn't want to belittle his own, natural class. "And I'm sure I can find the house on my own."

Shonda Spruce spoke then, her voice a rich alto and refined. "I have to start dinner for you guests anyway. I'll be happy to show you the way."

Green was still leaning into the fender, arms crossed, wrench in hand, and giving Scott a smile and, Scott fancied, an assessing look as Shonda led him away. Something inside Scott was clicking away. He didn't really want to leave; he wanted to crawl under the hood of that Mercedes with Jack Green and pull the hood down to give them privacy and intimacy. But he probably wouldn't ever see the man again. Scott knew the separate worlds he was dealing with here. The Lamottes of the world—the families of the Gang of Six that Scott ached to rise to—lived on the river side of the road going through the property. The caretakers and cooks lived on the other side of the road, where the river couldn't be seen.

When Shonda led him through the arbor and several steps along the path, he stopped and almost gasped. "This is the cottage?" he asked. "The Bluff?"

Shonda laughed. "Yes. It was built in the 1920s. The original owner wanted it to be like a hunting lodge."

And that's exactly what it looked like. Like the garage, it was walled in grayish-brown wooden shingles, a story and a half tall, and topped with a forest-green shingled roof. When he got inside, though, he discovered that most of it wasn't a story and a half, it just had very tall ceilings, with fans hanging down from the ceiling as its only air conditioning, the fans catching the breeze coming off the water on three sides of where the house perched, on a bluff, above the water.

The building was long, like the garage, but longer. Off to the right was the bedroom wing, with three large bedrooms, all with baths and all facing the water. This side of the wing was a wide hallway, wide enough, with cabinets all along the land side, to function as a sitting and study area. Studio couches that could be used for beds in a pinch were pushed up against the front wall between bookcases. In the center was a large living area, with a towering stone fireplace, and a screened porch with a large sleeping porch over it jutted out toward the water. The dining room also projected out toward the surrounding water at an angle off the back of the building off to the left, and the kitchen area, with a large pantry and the laundry room next to it was on the land side of that. Above the kitchen area, reached by a staircase up from the pantry hall, was a bedroom, bath, and small sitting room, presumably originally meant for a live-in servant. When Shonda showed it to Scott, he assumed that's where she slept.

"No," she said. "I live back a few roads toward Elkton. Still on the river, though. I just come in to work here when I'm needed." Then maybe to convey a message to Scott and maybe not, she added. "I'm a widow. My husband didn't come back from Afghanistan. No, this, I'm told, is where you are to sleep." She gave Scott another somewhat strange look then, a look that he only later understood had meaning.

When he took him out the back to the terrace area, a V of land jutting out on a bluff over the river, the bluff obviously being where the name of the house came from, he found the Gang of Six all there—all lounging around on patio furniture, in skimpy bathing suits, and drinking beer and smoking pot. Most of them looked like they'd been in the water. Looking toward the water, reached, Scott could see, by a wooden staircase down to a pier, he could see the bobbing mast of a fairly large sailboat.

"There you are, love," Lani said. "Come sit by mother. But don't get comfortable. We were about to go stumble around on the tennis court."

"But our weekend slave needs a beer, Lani," Chad said, rising up from beside her. "And the rest of us could use another drink as well—and some ice. And while you're in the kitchen, Scott, perhaps Shonda could show you where you can find some chips and nuts to replenish our supplies."

"Come, I'll show you," Shonda said, taking Scott's arm and giving him that look she'd just given him again.

Weekend slave? Scott wondered as he followed Shonda back into the house.

* * * *

"Shonda might appreciate some help bringing the food into the table," Lani said.

The seven of them were sitting at a long table in the dining room that was able to accommodate ten. Without asking why, Scott got up from the table and went into the kitchen to help carry the food trays. It hadn't taken him long to figure out what his role was this weekend—or what the looks Shonda had given him meant. He wasn't here as one of the Gang of Six. He was here to serve them, just as Shonda was. Except that Shonda was being paid and he wasn't. Lani and the others knew his place and they meant to keep him there. That's why they were doubled up, in their couples, in the bedrooms at the other side of the house and he was sleeping above the kitchen in what had been built as servants' quarters.

That evening, the group sat around and drink and smoked a few joint while they talked about the summer, what they were looking forward to at their schools in the new year, the various tennis tournaments they might try to enter, and, most of all, how some of their mutual acquaintances were doing. Scott could keep up with the rest on the tennis issues. But there wasn't nearly the interest in the University of Delaware where he was going as the colleges of most of the rest of them, which were, with one exception, Philadelphia schools with cross-interest pollination. Yale, of course, where Trevor Price was attending, was interesting to them all—in ways that the local school, UD wasn't. And all but Scott had graduated from Tower Hill private high school in the same class, so when they discussed absent class mates, they were all on the same beam and Scott was out to sea.

There were three couples, pretty definitely paired up—Rick Oliver and Gretchen Harrison were nearly glued together, already formally engaged—which left Scott unencumbered when anyone needed something fetched. So, Scott, as had happened at dinner, became Mr. Fetchit. He wasn't dumb enough to take this as being an accident, so, after the others had gotten anything out of him they wanted to consult about tennis, where he was the ace, and all had all of the refreshments they wanted for the night, they all turned from him. When he was the first to leave to go to bed, he thought no one had seen him go—or had cared.

It wasn't until late in the night that he found what else he'd been invited for for the weekend. The Gang of Six enjoyed fresh sex prey. Lani was the first one to arrive in his cozy double-bed room above the kitchen, crawling into bed with him in the dark and inserting a hand into the fly of his sleeping shorts. This was what he'd come for, so this was fine with him. He was on top of her, between her spread legs, inside her, taking her in the missionary position, when they were joined—by Rachel Bowers. Well, OK. Scott had been hit on at the tennis club by Rachel's boyfriend, Trevor Price, although that hadn't gone anywhere, so, if Trevor's squeeze wanted attention from Scott too, he was game. He didn't quite know how to handle two women at once, but they helped him by not being greedy and sharing him on the bed.

He was deeply absorbed with satisfying two beautiful young women, one a blonde and one a strawberry-blonde, both trim and in athletic form, when Scott heard the sounds of sex from somewhere else in the room. At some point when he was otherwise engaged, Chad Harlan and Trevor Price had quietly come up the staircase from the kitchen and were in an easy chair across the room. Trevor was buried in the chair, his legs draped over the arms and Chad was crouched over him, knees bent, and fucking him from in front. Chad's face was buried in Trevor's throat and Trevor's arms were flung around Chad's neck. Trevor was making the sounds Scott remembered himself making when Chad was deep fucking him really well.

When Chad finished with Trevor, he rose from the chair, came over to the bed, and pulled Rachel out of Scott's embrace. He bent her over the bed down near Lani and Scott's feet, where Scott and Lani were still connected in a missionary, and Chad fucked Rachel in a doggie position.

He was superhuman, but must not have really finished with either Trevor or his girlfriend, Rachel, because, without warning, he had pushed Rachel aside and Scott saw her and Trevor, arm in arm, disappearing down the staircase into the kitchen. Chad was still in the room. He was coming up on the bed, behind Scott. He embraced Scott with one arm while he was on top of Lani, doing her missionary style, and he positioned his cock at Scott hole with his other hand. Scott lurched and jerked as Chad mounted him in a doggie position, penetrated, and began to stroke, his thrusts controlling Scott's thrusts up into Lani. Scott was fucking Lani and Chad was fucking Scott. They fucked that way for long enough that They climaxed nearly simultaneously all around.

KeithD
KeithD
1,305 Followers
12