The Deviants' Room

Upstate New York, 2007 - Day 1

They all kept talking—bitching—about "sloppy seconds" but if you're drunk enough, and these guys were drunk most all the time, you don't really care about dipping your wick into a hole filled to overflowing with other guys' junk. You just stick it in, numbly hump for a few minutes, then make your own delirious contribution to the community pleasure center—a sloppy third or fourth that the next guy in line is going to complain about, before muttering what the hell and plunging in to his short and curly.

There were four of them, they were all in their mid-twenties and they all seemed to be relative new-hires at some Wall Street investment bank. Although one mentioned—complained—about the location of their building in midtown, so maybe it wasn't a "Wall Street" bank at all. I got the feeling they'd agreed not to talk business specifics in front of the "gurl"—me—so anything I learned about them, collectively or individually, I picked up in bits and pieces.

Their idea was simple enough: to spend Labor Day weekend in a cramped cabin upstate getting drunk, smoking weed, watching college football (I gathered it was the first weekend of the season), betting on the games, playing cards (more betting—and bitching) and, controversially I gathered, porking a shemale. Except...

...while omnipresent on the internet, like unicorns, in real life true shemales are, shall we say, somewhat more elusive. So their Deanslist personals ad specified the unspecific: Wanted: shemale/trans or crossdresser to...

And so, out of an alleged avalanche of "applicants" they chose me for the weekend: a mere crossdresser old enough to be their father. Or mother. I gathered that my age had been an issue for at least one of them, for on the drive up the one in the SUV's backseat whose lap my lanky, stockinged legs were not draped over said rather disdainfully, "Not bad for a grandma."

"What are you talking about, man?" the guy with the erection under my tent of girly legs said. "She's HOT! She's a MILF!"

"Each to his own."

"Oh, yeah, right, Jared. Like you're not gonna fuck her all weekend."

"I don't fuck other guys."

"She's not a guy she's a girl."

"She's a wannabe girl. Does she have a pussy? I didn't see any pussy in the pics Brad sent me. No pussy, no girl."

"She's got a man-pussy," the guy up front in the passenger seat grinned.

"Exactly my point," the one named Jared said.

"What?" the driver wondered, looking into his rearview. "You never had anal with a girl before, Jared?"

"With a girl, yes. Plenty of times."

"Well what's the difference between a girl's asshole and a gurl's?" putting some English on the latter.

"Plenty, Brad. Plenty," Jared sitting cross-armed now, just beyond my stockinged toes, looking sullenly out the window at passing quasi-rural scenery. And now I knew two of their names: Jared, the dyspeptic one, and Brad, the driver. Both literally and figuratively. I got the feeling Brad was the group's leader, probably because he had landed the best job at the firm and was making the most money, the biggest annual bonus. And I got the feeling it was Brad's idea to go left-field and hire a shemale for the improbable Labor Day weekend of debauchery. An almost shemale, just like in the porn flicks they all beat off to.

"Speaking of assholes...," passenger seat said, looking around—pointedly—at Jared. Everyone except the target laughed. Even I cracked a painted smile.

"Fuck you, Hamad!" Jared fired back. "Why don't you go fly a plane into a building or something."

"Hey!" Brad said, eschewing the rearview and this time wrenching his head and shoulders around. "That's sacred territory, Jared."

"Don't even go there," the one stroking my thighs added.

"Not to mention racist...," Hamad muttered, practically sotto voce.

Jared replied: "Yeah, whatever. Fuck you guys..."

While up front Brad cracked a malicious grin. His eyes were back on the road—well, sort of. "Jared, if you don't get onboard here I'm gonna dump your ass out at Tuxedo fucking Park. And you can catch a Shortline back to midtown."

Hamad: "Or walk."

"Or fucking walk," Brad agreed. He deftly switched gears: "Hey! Is it cocktail time yet?" glancing at what appeared to be a shiny new Tag Heuer. It was half-past ten o'clock. In the morning. And these guys were definitely not Goldman Sachs. If they were Brad's watch would have been a Rolex. A gold one. A Tag suggested something riskier, more...out there. Ballsier.

Hamad, feelings apparently mended, looked around. "Jared. Open the cooler. Pass around some cold ones. For the lady as well."

"Fucking how?" Jared whined. "The cooler's in the back!"

Brad: "So get off your fucking ass, turn around and open the cooler. The big one with the red lid."

"Let Simon do it."

"Simon is otherwise engaged," Simon said, his caressing hand running deep into the vee between my legs this time, leaving behind thigh-high lace and brief flesh to bump against my pantied cock and balls.

"Oh fuck you, Simon!" Jared said, letting fly his seatbelt. He swatted at my feet. It had started out as a harder blow but—last second—he checked right hand's velocity. It was that or Tuxedo Park. I pulled my feet back into Simon's lap and massaged, through his Chinos, Simon's hard-on with the curvy sole of the right one.

"That feels so good, baby..."

"Dat feel so goot...," Jared mocked, up on his knees now, facing backwards, reaching for the cooler.

"Oh baby..."

Hamad observed, as dripping-cold Heinekens made the rounds, including to me: "Simon's already getting some action back there."

Brad: "Don't shoot the pooch yet, Si!"

Jared, facing forward again, seated: "Why don't you two fucks get a room? Like in the back?"

"Too many coolers...," Simon said dreamily.

Conclusion: If any of the four was a someday latent-gay...it was fucking Jared.

Because of his head start, Simon went first. In fact, he was in such a hurry upon arrival at the cabin, he didn't even help the other three unload. He had his own urgent unloading to do. He led me straight to what became known as the Deviants' Chamber, a room in the cabin only slightly larger than the average walk-in closet. It contained less of a bed than a metal cot with a single layer of bare, stained mattress. No boxspring. No pillows. That and a lamptable of very old, rickety wood. An antique only in years. I didn't even bother to ask about sucking Simon's cock. For one thing it was already hard; hard and pointing at the rain-stained ceiling, as if a mirror image of the mattress. For another he hurried past me and opened the table's lone drawer. Simon removed a flattish-looking tube of K-Y. Shook it. Obviously this was not his—their—first rodeo here. He said, as he began extracting the last of the clearish contents and smearing it over his cock:

"Fuck. I hope somebody remembered to pack lube..."

"There's that general store we passed back..."

But a smiling Simon wasn't interested in general stores. Or specific ones for that matter. He brought his greasy hand over and, palm up, took hold of my cock. Which, though engorged, was not erect. That was not my role here. Simon gave it a stroke.

"Nice clit, baby."

"Thanks," I said, smiling in turn as I stepped out of my pink Olga's. Pink panties, black thigh-highs, matching B-cup bra. Though the only thing inside the cups was a gold tube of hot-pink lipstick. My eyeshadow was green, matching my eyes. The gloss complemented my panties, though the latter were of a much paler, conservative shade. I tucked a stray curl of platinum-blonde behind an ear, my right one. I could see the desire in Simon's eyes. The wonderment, almost, as he held my "clit." Fuck. I really was cute. In his dark eyes at least. I returned the favor, taking hold of Simon's slippery erection. "But not as nice as yours."

"That ain't a clit, baby," Simon declared, a tad of Jared's resentment entering his voice. "Let's do this."

"How do you want me, baby?" tucking another stray strand. It was a pageboy wig, bangs at the front, inward curls at the sides, hanging down just an inch or so below my earlobes. I'd debated whether to wear the brunette or the blonde one. I chose the blonde one, and was glad of it. Meanwhile, Simon reacted as if such a question had never come up before.

"I don't know," he said diffidently. "On your hands and knees?"

As he walked forward behind me on his own knobby knees he said two things: "This bed SUCKS!" and, more diffidence entering his voice, "Guess I shoulda brought condoms?"

I said nothing. Meanwhile we—I anyway—could hear through the door: "Fuck! Simon's already at in there!"

"We should watch!"

But Brad said: "No! You go in there, close the door. That's your personal time. No voyeurism shit on my watch."

"I was just joking..."

"Them's the rules," Brad added, probably after a face-clenching swig of Heineken.

Simon seemed surprised at how easily it went in. He should not have been. His cock size was nothing to write home about. Not that anybody would ever "write home" about such a thing. Besides, before leaving my apartment in Jersey I'd thoroughly prepared my body. Douching myself—twice—and then, in the shower, opening myself up nice and wide with my largest dildo. I was prepared for any contingency short of a fist. A whole three-day weekend of them, in fact. Contingencies, that is. Simon, bush-deep in me, remained still for a long moment.

"You feel so good, baby..." He was running both his hands over my spread cheeks and lower back and I wasn't sure if he was referring to my smooth flesh—I'd shaved and Naired my entire body the night before—or how my even smoother rectum felt loosely clenched around his cock. "You have such a sweet ass."

I was really starting to like Simon. He was probably—definitely—the least attractive of the four, but then again he wasn't fucking me with his narrow, bearded face. He took hold of me by the scant flesh of my hips but once again delayed, deeply, reaching under to feel my clit. Engorged just moments ago, now it was almost completely limp.

"You don't get hard, baby?" Simon asked.

"I leave that up to you guys," I replied, smiling down at a mattress stain. The wigged top of my head was only a foot from the headboard. Who the fuck, I wondered, cums this high up on a bed?

Simon had laughed, softly. But now he pushed my submissive body forward saying, "Oh, baby," before slamming it back against his hairy flat abdomen, his upper thighs. Simon sighed, almost wistfully. He was a quick-cummer, I could tell. This inaugural fuck of the weekend wasn't going to last long.

It didn't.

Simon departed the room in a New York minute, yanking his pants back up in the process. Through the open door I could hear the voices of ESPN's Gameday. Someone had turned the TV on and was complaining about the reception. Probably Jared.

Brad entered, kicking the door closed behind him. His thick arms bore sheets and pillows. Thanks!

Brad wanted me to make the bed. I was the closest thing to a maid in the cabin, after all. Then he wanted me to suck his cock. I was glad to comply, sinking to my stockinged knees. His cock tasted of fresh beer-pee but that was OK. It was fresh. Brad, looming above me with his hands on his hips, said:

"I was thinking. It might be fun..."

I pulled my mouth back. Wiped it. Looked up. "What?"

"If, you know, we paid you by tucking the cash in your garter."

"I didn't wear a garter."

"I mean your...," Brad gestured, "whatever. Stocking. Fifty times four, each day. Y'know? Make you feel like a real whore."

I smiled up at Brad. "I AM your whore, darling."

"Then suck my cock, whore. And don't call me darling. I don't like familiarity from whores."

Before Brad penetrated me, atop my stack of pillows, he tucked a crisp, folded-over Grant inside the tall lace top of my thigh-high. Then he gave my bare ass a whack. Before penetrating me—just before—Brad asked:

"Did asshole cum in you?"

"Who's asshole?" I was thinking of Jared, in the car.

"Who do you think?"

"Oh. Yes."

Brad guided his cock to my dilated hole. He pushed in. "Fuck. I hate sloppy seconds..."

As I brought Simon, sunk deep in a redwood Adirondack chair, facing the TV, a cold Heineken, he summoned the energy up to lean forward and, reluctantly it seemed, tuck a fifty inside my left lace-top. Which now sported four. Four fifties. One day's salary. Complete.

"Thanks!" I said.

Simon sank back. This was Brad's idea and I could tell the others didn't like it. Or at least Simon and Jared, on the same page for once, didn't. Besides, Simon was still recovering from the post-orgasm guilts. Less than an hour earlier he'd fucked another man. A man dressed as a woman, admittedly, but a woman sporting a cock and two balls. His thrill over the size of my "clit" having long since evaporated. Simon didn't reply. Maybe an endless supply of Heinekens would help.

"Anybody else?" I said, referring to cooler-cold beer. My pink panties were back up, panty-liner in place. And my slender, stockinged feet were sheathed in flats. A pair of silver-and-black slings. I was too tall, at least in my opinion, for heels. I wore them at the club, on Thursdays, but that was part of the "uniform." Heels were required. They hurt my feet, however, especially after about the third set. I would have much preferred to dance in my stockinged feet.

"I'll take a lap-dance," Hamad said, speak of the devil.

I looked over at him. Blinked. Forced a smile. "Really? Um, OK."

I headed over but Hamad waved me off. He was joking. I guess. "Maybe later," he said, taking a swig of his beer. I tried to sound interested:

"When's the game come on?"

"Now," Brad replied. "Who's got the remote? Jared? Put the fucking Michigan game on."

"The Northwestern game comes on at noon."

"OK, put the fucking Northwestern game on."

"Chill, dude. I got this, OK?"

"Get it faster." I could just hear Brad on a trading floor, barking orders at subordinates. He too, like Simon, seemed a little...testy. Pissed off. About something. Me? The fact that they'd hired a crossdresser—another biological male—to spend their long weekend with? Was Brad suffering from the same same-sex guilts as his broker colleague?

Hamad seemed the coolest about the whole thing. Positively breezy. And fun in bed too. He had the biggest cock of the four, the thickest anyway, and he'd fucked me both on my hands and knees and on my back, smiling down at me the whole time. "I love your lips, baby," he'd said.

"But mainly I love your sweet ass."

I laughed, sort of. Between moans. Hamad was not too big for me. It was more a case of being...just a millimeter thicker than just right. We must've fucked for twenty minutes. This way, that way. Hamad also had the best stamina of the four. Unlike Brad, and in particular Jared, he'd only spanked my ass after coming in me, and pulling out.

"That was fun, baby!" Furthermore, Hamad showed no signs of post-coital regret. He was great! And I gladly would have "danced" in his lap for him.

Brad said: "Hey, Nikki." As far as I could recollect it was the first time that day anyone had addressed me by my fem name. By any name at all. Brad was pointing toward the kitchen. Which was more of a wood-and-formica kitchenette crowded further by cavernous Igloos. "In the cooler, the blue one, there's a thing of wings. They're already cooked. All you gotta do is spread 'em out on a sheet and-"

"And stuff one up your ass." Jared being Jared again. Brad ignored him:

"And reheat 'em in the oven. Like...three hundred degrees?" Brad was still pointing: "Should be, like, a tray or something in the drawer under the oven I think."

"We got celery and blue cheese?"

"Oh right, I forgot. Simon's a vegan or some shit."

"Fuck you, Brad."

"In that same cooler is another plastic thing my wife made up for us. Celery. I think it's already cut up. Then there should be a couple of jars of Marie's in there. Get a bowl out of the cabinet," pointing higher, "and dump the blue cheese in that. Hey," to the others, "no double-dipping OK?"

"Is that like sloppy seconds?" a grinning Hamad inquired.

"Don't even mention that," Jared winced. "I got fucking Brad's cum and Simon's cum on my cock. Disgusting!"

"Wear a condom then."

"I hate those things! Besides, that doesn't keep it from getting in your hair."

"What? When you were sucking Nikki's clit?"

Jared made a face. An even more disagreeable one. "What?"

Two of the other three laughed. Simon, slumped, didn't. I was busy squatting in the kitchen, looking for a tray. I found a cookie sheet. That would do. Good thing I'd inserted a panty-liner. The squat had induced more collective semen to ooze from my hole. I could feel it, the sticky wetness, exiting my body and mating flesh to liner. Oh well...

I continued to follow orders, taking out the Tupperware full of celery, dumping blue-cheese dressing into a found bowl. Northwestern, in their purple unis, had just kicked off. Northwestern v. Akron. Whoopydo!

"This is one of those 747 games," someone declared.

"What's that?" Simon, rousing himself, asked.

"You know," Jared, the author of the remark explained. "If a 747 crashed into the stadium? Nobody would fucking care."

Brad snickered, so did Simon. I rolled my eyes. More Wall Street macho bullshit. Hamad said, "Jared, you really got a thing for crashing planes, don't you?" Except he said "clashing."

"Speak English."

"You heard. Fucker."

"You'd know, Hammie."

I guessed "Hammie" was another intentional slight. Hamad probably didn't eat pork. He did eat—devour—chicken wings however, I soon found out.

What else had I learned so far? That Brad, the group's leader, was married. I could hear them now:

"Just a weekend at the cabin with the boys, hon."

Stamping a foot, perhaps: "I thought we could drive out to the Island."

"It's business, honey. It's a bonding trip. These are my traders. We gotta be on the same team. Get to know each other better. We gotta be able to read each other's minds on the trading floor. Literally."

"Any women in the group?"

"Are you shitting me? No! You know Hamad and Simon. It's us three plus Jared. Guys only. No tits allowed."

"Oh. Nice language..."

Brad wasn't lying. It was a guys-only weekend. It was just that one of us, the unmentioned one, was dressed women's underwear. Underdressed. A titless woman with her ass in the air wearing an invisible Open for Business sign.

The deal had been two hundred dollars a day for three days. Unlimited sucking and fucking. I would be completely at their disposal, sexually speaking. And non-sexually as well. "When you're not in bed with one us I'll expect you to kind of be our maid. You got a maid's outfit?"

"No."

"You should get one. But that's OK. When we're not fucking you or out hiking or whatever we'll be hanging out getting high and watching the games. Or playing cards. Or fucking both. That's when you play maid for us. Got it?"

"Sure," I said, a little warily. This guy was very intimidating. His voice like a hammer against a row of nails. After a flurry of email exchanges we were at last speaking by phone. Nailing down the details with, from his side, hammer blows.

"Think you can handle four horny guys?"

"Sure," I repeated.

"Ever had a threesome?"

"Yeah," I replied truthfully. I'd sucked one guy while the other fucked me. Then they'd switched places. Both came in me. No money was exchanged. It was just fun and games among one-night "friends."

"How did that go?"

"Great!"

"Well this'll be two times that. We expect our money's worth."

"You'll get it."

"I like your confidence," the trader said. "Where should we meet? Will you be dressed fem?"

"Uh..."

"Don't fuck with me, man. Or lady I should say. Yes or no?"