Jack's Offshore

Story Info
New Orleans crossdresser/transvestite meets offshore worker.
7.2k words
4.15
5.7k
7
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

The blue and white Bell Jet Ranger helicopter was closing on the oil rig, 80 miles into the green choppy sea off Port Fourcon, Louisiana. Jack told himself he wasn't going back offshore again! Ever! Yet, here he finds himself, accepting another hitch -- not on the platform he's flying to, but on the one-hundred-forty foot supply boat tied up to it. 28 days on - 14 off.

Although his experience on resupply vessels would likely secure him a better-than-good shot at a lucrative position on a platform, Jack knew it was too much of a career for him. Too much responsibility. These rig companies will constantly ask him "go to this school" to acquire new skills and "go to that school" for a new certification. Thoughts of it found his motivation on the floor. Plus, they'd ask him to do things, many things, which if done incorrectly, could result in loss of life or limb. The boat was plenty dangerous, but he was an independent contractor there. Deckhands were the lowest paid workers in the industry, and that was just alright with Jack. He was by no means stupid -- he just wanted to do stupid work.

Along with Jack and the pilot, were two rig-operators and a roustabout. None spoke during the entire thirty-five minute flight.

As the chopper banked for the approach, the roustabout vomited into a bag handed out by the pilot before take-off.

Can't even handle the helicopter ride. Sorry bastard - Jack thought to himself.

Jack knew from past experience, this young guy was going to have a hard time on the rig. Rig guys and boat guys are not the same when it comes to motion sickness. Most boat guys can go through almost any sea and still keep their lunch. Not so with rig guys. They suffer. Even though oil platforms look stationary from a distance, they sway terribly in heavy seas.

As the skids beneath the helo where touching down, Jack was already longing to be back in the gay bars of the French Quarter. Everything from the big dance clubs to the hole-in-the-wall spots. He thrived in that environment. Jack wasn't attracted to the men in this flying box -- not even a little bit -- but he loved being wanted by the men in those bars. He'd been heavily desired by beautiful women in his past. Slept with plenty of them - but none could equal the ravenous intensity of unfamiliar gay men in heat. Jack found that most of the single gay men in the Quarter weren't looking for love behind the eyes. Many, not even like.

Jack would come in from offshore with a fat 28-day paycheck waiting, catch a Greyhound bus to New Orleans, and pay for two weeks in a cheap hotel. Sometimes, he was so excited, he'd put his off-shore bag in a coin-pay locker in the bus station, and head to the bars in the same dirty work clothes and knee-high rubber steel-toed boots he stepped off the boat in. He wanted to be seen, and fast.

As he approached any gay bar, his routine was to take off his shirt, tie it around his waist, and step inside. Jack has a swimmer's build with arms much larger than had ever been seen on any swimmer. Just past six foot tall, his overall appearance is striking. Thirty-six years old and solidly developed. Strong chin and wispy blonde hair, like that of a young Iowa corn farmer. His amazing hairline will never move.

His routine: he'll enter, step to the bar, and order a Budweiser or some other bottled beer. This will be the last drink he'll purchase all night. Queer as Folk is on the big screen behind the bar and "Better off alone" is bumping from the speakers. It won't be long before some older gentleman comes up to talk. Sometimes, they'd reach around and grab his cock first -- and then talk. The attractiveness of these men was of no consequence. It wasn't about looks. Men were just men -- they just had to lust after him.

He favored the older men because they carried with them a certain desperation. All the better, as it added to their desire. A sultry rush of expediency emanated from them that just wasn't there in the younger guys. For each, he was the Big Fish. A last chance at excellence in a lover. Plus, most where at a point in their lives where they were financially well-off. Many live Uptown in in large Victorians, or owned a place in the French Quarter. Some lived Uptown and held a second place in the Quarter -- just for guys like Jack. Either way, they had play-money. On some occasions, a random opulent tourist would whisk Jack away to a suite in one of the pricier hotels. No matter if it was a local bottom or a tourist, jack just wanted to get their legs up and drive. He never cared too much about the money -- but it did make things easier. No worries about splitting the check in a bar or restaurant. No concern about paying for anything. Ever.

In the gay community, Jack is what's considered a power-top -- just might be considered a prostitute also. He prefers to top. He's bottomed before, but it didn't do much for him, other than make him aware of the constant throbbing sensation in his colon in the hours that followed. He's given some blowjobs too, every one of them to orgasm, he often recalls proudly, but his head doesn't naturally desire to go down there. Legs-on-shoulders is Jack's favorite position, but some aren't able to do that. Some were obese, perhaps from the excesses of beignets and gumbo. Others, just too damned old. These men had to sit on his throbbing fuckstick or take it from behind. Many just prefer it from behind. No matter the position, Jack would be the Alpha.

The chopper came to a rest on the helo-pad on the far right quadrant of the oil plarform. The pad is designed for just this kind of personnel exchange.

"You fellas enjoy!" the pilot yelled from a mouth framed with aviator glasses and an ear-muffed headset.

Jack and the others grabbed their large offshore bags, donned their hardhats, and stepped down onto the rig. Near a large, rusty yellow crane, three men were waiting for the chopper-cabin to clear so they could embark.

Jack stooped low and scooted clear of the whirling blades, traversing down a single set of metal steps. He set the over-sized duffel bag down on the abrasive non-skid surface and waited for further instruction.

Sunshine beamed with what felt like added strength. The Gulf breeze was amazing. Peering up past the cold steel, to the soft blue sky, Jack imagined most people would consider what he was experiencing -- dreamy. A delight.

Just then, a door behind him opened. Jack turned. A large, burly, middle-aged man wearing green coveralls and a white hardhat stepped into Jack's dream.

"Hello Jack!" Mike Rogers said with a grin.

"Mike"

They shook hands. Jack wasn't much on small-talk.

"How's Mary and the kid's?" he asked.

"Mary's alright, but that son of mine is going to drive us mad. Three stints in rehab, and here we go again. This whole thing is breaking Mary's heart. Dog died last week and work's slowing out here. I see the plot of a country song building!" he laughed, his voice rising up and out of the gloom.

"How long you out here for this time?" Mike asked

"Twenty-eight." Jack responded. That's what they tell me anyway. I got fucked last time out. My relief never showed up to the office in Houma, and I had to do his twenty-eight too. Fifty-six days is just too much." Too much time away from the scene -- Jack thought to himself.

Hugging the steep curve, Jack steals a quick glance to the sideview mirror, nobody there. Holding, are three bald tires, and an almost new one on his beat up black 1993 Nissan Sentra. Hood and roof strafed with bird shit. Beer breath and a hint of mufalata fills the cabin. Jack doesn't give a thought to cracking the window for fresh air, as it's already stuck in a two inch gap. Won't go down any further. Won't go back up either.

Jettisoning New Orleans. But for what?...to where? -- he doesn't know. West. Anything is better than The Big Easy, and at the same time -- nothing is better.

"Fucking Decatur Street."

As he nears the end of the on-ramp, merging onto I-10 West, Jack scans the rearview and sees no cars behind him on this six lane interstate. Nothing ahead either. A strange gap in a normally busy stretch of highway.

"If it could only be this, stay this way -- just for a little while or just forever. The whole world to myself. A chance to recover and catch up."

Another look back reveals an old gray Cadillac breaking the horizon.

"Damn. Had it for a moment."

Nick Drake's "Parasite" starts on the radio. How aprapos.

"Didn't he off himself? OD'ed on depression meds I think. Fuck, this shit has got to stop. It just has to. I'm closing in on forty with no plans. No prospects. I'm losing."

Scanning the dash, Jack sees the constant glow of the yellow check-engine light that's been showing since two Augusts ago. Gas almost on empty, but he's not stopping yet. He knows he has to create some distance between himself and the puddle of vomit comprised of Zapp's chips and Abita Beer -- the splatter he left next to the newspaper stand outside the A&P on Royal.

"Good times!"

Sarcasm has never been more earnest. In this moment, comfort in his own skin is tied directly to the rolling numbers on the odometer. No comfort yet, still being this close to his latest debauchery.

"I have to get out. Fuck!"

Jack reaches over to the passenger-side looking for a loose smoke and the map of the United States he picked up at a gas station just outside Fort Meyers, Florida. No cigarette, just some loose tobacco and eighteen cents, but there's the map -- falling into the gap between the seat and the door. Jack reaches for it, swerving toward the concrete divider in the middle of I-10. A quick jerk of the wheel pulls him back to his lane. A sharp hot-flash of panic follows, the kind he used to get in elevators and sleeping bags. These attacks made him feel as if his brain was heating up. Almost to a rolling boil. Intense sweating and spots before the eyes weren't far behind.

"Keep it together." he scolded himself. "I can't let myself faint behind the wheel of this shitbag."

He'd been able to pull himself out of impending panic attacks before by simply telling himself, "I'm not focused. That's all it is. I'm just not focused." Using this mantra, he'd been able to narrow his vision and bring his head back to where his feet were at. Great coping skill under normal conditions. It worked well in the past, but not now. Yes, it's true, Jack was indeed completely unfocused -- but this anxiety was based more in the alcohol withdrawal and self-loathing - accompanied by an intense feeling of wanting to be anywhere but inside his own body -- and, of course, a close call with a concrete median.

Half-a-dozen cars were around him now, and Jack made his way through and around them to finally find the shoulder of the road. As he slowed to a stop, a delayed dust cloud enveloped the vehicle, first dimming his only working brake light at the trunk, and then making its way over the roof and into the broken window.

Jack coughed and wiped his nose, watching the remaining dust roll off of the hood, only to be grabbed up by a passing eighteen wheeler and turned into a Dr. Suess swirl. He gathered himself.

"A beer and a cigarette. That's all I need."

Jack knew from experience that one doesn't do well to linger on the shoulder. State Troopers are like southern biting flies: once they see the target, they have to bite. And bite they do. Although in withdrawal, Jack couldn't be certain his blood-alcohol level was low enough to be considered legal to drive.

"Gotta get moving."

Jack accelerated, throwing stones and dust in his wake. He merged back into traffic, narrowly avoiding the broadside of a gold minivan traveling far too fast for the slow lane. As he reached fifty-five miles per hour, Jack could feel the rattle of the chassis and see the shaking of the steering wheel. If his last name were Palance, he would have pulled right back over to the shoulder of the road - and shot this gimpy steed.

As he continued on, Jack began to daydream about Roxanne. With no alcohol currently in his possession or in his system, thoughts of her would be the only escape from his present reality. Of all the lovers he had bedded in New Orleans, Roxanne would be the only one he would miss. Certain he was unable to love, Jack was sure he felt something close to love for Roxanne.

They met last March, at the Oz nightclub on daiquiri-night. Post-Mardi Gras, these sort of events attract a large, local gay crowd. Roxanne was a tall and absolutely amazing cross-dresser. Even without heels, she towered over Jack.

He recalled the first time they locked eyes. She was coming out of the bathroom stall, pulling down on both sides of her green sequin gown. Jack was turning from the urinal, still trying to push his thick tool back inside his zipper.

She looked down in time to catch sight of its beautiful veiny flank - just as the snake made its escape into a denim and cotton jungle. Roxanne froze and leaned back with her hands on her hips.

"Daddy!" She remarked in a deep, but feminine voice - along with a tilted smile.

Jack, froze as well. Not so much that they both knew the reason for her comment, but because, she was in fact -- stunning. Apparently, fun too. Before he could fully process her command of the encounter, his newly-tucked-away cock started to jump with excitement, bouncing inside his right pant leg. This action caused his urethra to squeeze out a last pulse of warm piss which had managed to escaped the club's plumbing.

"Buy me a drink?" she followed.

Jack hesitated for a moment, still locked in heat - then replied, "Sure."

Holding Jack's hand, Roxanne led the way out of the purple-lit restroom and out into a sea of dancing gay men -- some of whom wanted to look like, or be women. This was Roxanne. Jack noticed her hand was soft and much larger than his. Long, perfectly-painted fingernails were adorned with small hoop rings through the tip of each fingernail. These details seemed to cancel out the difference in hand size.

Jack was caught in Roxanne's draft as they made their way to the bar. Her scent was divine. The end of a long pink wig bounced off the small of her back, forcing one air current of delight after another into his nostrils. In her hand, Jack was floating like a Mylar balloon at the county fair. With surprise, he looked down, finding his feet were still on the ground.

They found two open stools at the long round glass-top bar. Bartenders inside the circle were busy like bees defending a threatened hive. Jack could see Michele,' his favorite bartender, was busy pulling a draft beer. Looking around as the glass filled, Michele noticed Jack at the bar with Roxanne and acknowledged him with a nod.

Michele is a beautiful specimen -- short and wirey, with slick black hair pulled up into an Elvis pompadour. A single curl protruded from the steep rock-face of hair, coming down over his left eye. Dressed in tight silver shorts and a pink half-shirt with the sleeves cut off, Michele resembled a gay doll just out of its packaging. When he finished, he came over to Jack and spoke over the loud music with a thick Italian accent, "Hello Jack!"

"How are you Michele?" Jack replied. "I want you to meet a new friend of mine."

Jack suddenly realized he didn't have a name for this new friend. Before he could clean it up, Roxanne reached across the bar, offering a hand with a relaxed wrist.

"Roxanne."

Michele immediately smiled, grabbed her hand in both of his, and kissed it just above the knuckles.

"Bella" he said, his eyes meeting hers.

Michele straightened up and tossed out two napkins on the bar to serve as coasters, "What are you drinking tonight?"

With learned chivalry, Jack deferred to Roxanne. "I'll have a Cosmo" she said.

"Beer for me" Jack followed.

As Michele turned to fill the order, Roxanne, facing Jack asked, "So, what's your story stud?"

For a moment, Jack looked distant. He raised his hand to his forehead and pushed his hair back.

"I'm from Los Angeles originally. Grew up there." Jack sipped his beer.

"Left sixteen years ago and never looked back." He thought of his childhood, and how it had scarred him. Anyone who's spent some time around Jack would conclude he's a tortured soul. He'd done well in school, played sports and experienced a wealth of friendships in his youth. This was all before his mother married Tony when Jack was nine.

Anthony Blago was an out-of-work meth addict given to abusive behavior based in resentment. While Jack's mother was at work, Tony would often take Jack out to Hemet, the high-desert - in order to complete a drug transaction. On these day trips, Tony would travel between three houses in Hemet. Two were located inside the city limit, but the third was way out in the desert with no other houses in sight. This was the one they always visited first. The house was an aged powder blue, with a sunken roof on one side of the peak. A rusted out 73' Vega adorned the arid front yard. Inside, were two residents, and always five or six other people who were unknown to Jack. Every time they pulled up, three brown Pitbull terriors would fly out the front door. They'd surround the car, snarling and smearing saliva and muddy claw marks all over the windows. As a young boy, Jack was frighten by this, but in his adult year had often wished the trauma stopped with the dogs - but things would get much worse.

Roxanne continued her interrogation, "What brings you to New Orleans? Why the Big Easy?

Jack snapped out of his reflection and turned to the present moment with a bit of a start, "Just the latest stop. I like it here. I find that I can be myself."

"Do you like me?"

"I do" he said, looking away while taking another pull off of his beer bottle.

Roxanne blushed. Her full, painted lips parted as if say something -- but they hesitated. She was overcome. She realized she adored him already.

Roxanne is an amazingly gorgeous crossdresser. Beautiful blue eyes with the clarity and depth of Lake Tahoe. A strong jaw-line, but with the way she applied her makeup, a decidedly feminine countenance emanated from her. Long smooth legs which ended at a perfectly round bottom. Lashes so long, a wink might blow out a candle. Exposed, thin arms, holding a few gold and silver bracelets at each wrist. Hoop earrings. Her smile was near perfect.

Watching him scan the room, Roxanne imagined herself in his arms. She imagined him taking her, over and over - their bodies joined together in shared ecstasy. She thought of his warm semen filling her up as they both moved together towards dawn. At this thought, she felt her member, which she referred to as her "clitty" - quickly growing in her chastity cage. The expansion pushed the soft skin of her pink sweet-scented button firmly against the cage holding her unit. She felt pain - and passion.

Roxanne refocused, "Do you want to go for a walk?"

Jack returned, "Okay, but let me do something first."

He downed the remainder of his beer and headed towards a small stage in the middle of the club. Three near-naked men, hired by the club, were dancing in g-strings -- surrounded by excited gawkers. Jack made his way through them and put a folded twenty-dollar bill inside the narrow panty string of one of the glistening specimens. All at once, the chiseled brunette dancer winked at Jack and pulled his bikini aside to reveal a fantastic root. Thick and long with a bulbous head, his manhood was swinging side to side -- opposite to the motion and direction of his hips. Jack smiled and threw up his hand as he made his way back to Roxanne.

"Let's go" he said.

Roxanne unfolded her legs and brought them straight together as she stood up. The inside soles of her long heel shoes almost clicked together as she ascended. She leaned down and gave Jack a kiss on the cheek.