Halloween Jacks

A straight-arrow business professional steps way outside his comfort zone.

Author's Note:

There was some debate about which category this story lives in. Some will disagree, but wiser heads than mine advised that it could—but really doesn't—belong in Erotic Encounters, or Group Sex, or even GM. There's a fetish element to this story, and it probably fits the "kinky" aspect of the Fetish category. Never mind the category. I hope you enjoy it.

Please be advised: This story contains scenes with graphic details that some will consider to be "nasty" or "over the top". You have been advised.

* * * * * * * * * * * * * * *

Nine o'fucking clock on Monday morning in New York City, and I felt like shit warmed over.

I'd woken up two hundred and fifty miles away at four am., shat, shaved, showered and shampooed. A quick kiss on the forehead to my sleeping wife, out into the late October chill, then into the traffic to Dulles airport. When you live in the Washington, DC area, you have traffic jams at 5:00am. In God's name, why?

There was the interminable crawl through the security line, followed by the cattle-car boarding, and the usual delay on the tarmac before we finally took off for JFK airport. And then I had to endure a talkative but incomprehensible New York cabbie for forty five minutes blabbing on, I think, about American liberal politics.

I made it to my client's offices in Manhattan in time for the nine o'fucking clock Monday morning steering committee meeting. Corporate America frowns on religion in the work place, but when your client is a boutique health insurance plan owned by the Catholic Church, they actually pray before meetings.

It was going to be a long day.

This is the glamor of business travel—the ritzy life of a management consultant.

At seven o'fucking clock that evening I finally escaped the client's offices and Ubered my way to the hotel. It was a four-star affair, but my only concern was that it had a decent bar and a reliable high speed Internet connection.

After an hour in the hotel gym, a light dinner and three cabernets, I went upstairs and undressed. My wife and I are nudists and tossing my clothes onto the bed was a blessed relief. I felt normal for the first time that day. Normal, and naked.

I called Debbie using the cell phone's video chat service. We'd been married for twenty two years, yet I still make a point of speaking to her at least once a day when I'm away. And at that time, courtesy of my ritzy new job, I was away about two weeks in every three.

"Let me look at you," I said.

She held the phone at arm's length and I could see she was nude, in our living room, like any normal weekday evening. "How're you settling in with the new client?"

"It's going to be a tough project," I groaned. "I told you how religious they are, right? They send a weekly inspirational message to everyone, employees, contractors, and consultants, and it's mandatory reading. 'Course, I just skim them, but this week's message was a dusey."

"By inspirational message, you mean something religious?"

"Yep, though I wouldn't call it inspirational. It's where they push the Catholic principles down their employees' throats. Of course almost all of the full time employees are Catholic. It's practically a job qualification."

"So what was special about today's notice?"

"This one was written by the new director of the PMO, the guy who I'm working with here. This character's name is Jonathan P. Mountford the third. And don't you dare call him Jon, or God forbid, Johnny.

She laughed. "Sounds like he's a bit stuck up?"

"Yah, a real stuck up twerp, which is a pity because the managers above him seem to be pretty decent people. But this Johnny is a real holier-than-thou prig. He tries to project this impression that he's five steps closer to God than anyone else. And when he leads the prayer at the beginning of the meetings, he rambles on and on for fucking ever!"

"Nice guy," she rolled her eyes. "So what was this message he wrote?"

"It was mainly about sex and adultery. Hands off your buddy's wife, condoms are evil, gays are evil, and thy shalt not indulge in self-pleasure," I chuckled.

"Well then you're going to hell!"

"I'm not gay," I protested.

"No, but you've had your hands on your buddy's wife, and you've used condoms. And there's that masturbation thing!" I laughed.

Two years ago Deb and I went to a swingers club. Four times, if memory served, and there'd been plenty of hands on other peoples' wives. And of course there was the jerking off thing. My wife and I have an open masturbation policy. We encourage each other to jack off, or "jill off" in Debbie case, any time we like and as often as we like. I do it a lot more than she does, and she jokes that I'm a chronic masturbator.

Our day-to-day sex lives were frankly quite boring except for one saving grace. For as long as we've been together we've had a tendency to do something crazy and out of character every few months. It would usually be a spontaneous escapade, often after a few drinks. We're pretty straight-laced, we're both business professionals, socially conservative, and our friends see us as the ultimate straight-arrow couple. They'd cringe if they learned how many exciting and very sexy experiences we'd collected over the years.

Deb's open acceptance of sexual adventures came with her absolute trust that neither of us would do anything to harm our marriage. And that was just one of the reasons that after more than two decades I still loved her beyond anything else.

"Well on that basis, I guess we'll be going to hell together," I told her.

"You rubbed one out yet tonight?"

"Soon as I hang up," I smiled. "it's lonely here."

"Well, think about how many other lonely guys are on business trips right now," she said. "How many rooms are in your hotel? A few hundred? More than half of them are probably occupied by lonely business travelers. I bet that more than half of them will be masturbating in their lonely beds tonight."

"Jesus, that's a thought." I did the math. "I guess there'll be about forty people jerking off all around me tonight!"

She laughed again. "You guys should form a club."

The conversation turned to more mundane things, and I ended off with "I love you, Deb."

"I love you too, Neil. Now go and rub one out, and tell me all about it when you get home."

"Yep, I'll be taking matters into my own hands as soon as we hang up."

"Me too."

My travel bag always includes one of those small hotel shampoo bottles that I'd emptied out a long time ago. I fill it with lube before every business trip. I threw the bed covers back, fluffed up the pillows, and spread liberal amounts of the clear, water soluble lube on my hand and settled back for a long, satisfying session.

My right hand took long strokes, sometimes squeezing hard, then barely tickling the sensitive knob, then closing my fist tight again. My left hand pressed hard on my perineum. I thought about Debbie sitting naked in our living room, masturbating right now. I cupped my balls and massaged them in my left hand. And I thought about what she'd said. There were probably at least half a dozen guys jerking off in this very building, right now. It would be their dirty little secret because I couldn't imagine that many of them would have a wife as understanding as Deb.

My movements sped up. I pressed hard beneath my balls. It wouldn't be long now.

Deb said that business travelers should form a club. I imagined fifteen or twenty guys in a big circle jerk, imagined them all coming.

It was time. The middle finger of my left hand slipped into my ass. My grip was intense and my right hand moved so fast it was a blur. Then there was that pressure buildup from the core of my being, through the base of my cock, and out. It was a creamy lava flow. Down my hand, into the trimmed pubic hairs, down, past my balls and into my ass crack.

I never bother to clean up in hotels. The cleaners probably see sex stains on the sheets every day. I flipped off the light and went to sleep thinking about a business travelers' jack off club.

As I dozed off I mused that I'd been to strip clubs while on my travels. I'd had lap dances. I'd refused propositions from hookers more times than I could remember. And I couldn't begin to count the number of times I'd masturbated alone in hotel rooms. There had to be more.

I'm an occasional insomniac. About once a week I'll fall asleep, then wake up after half an hour and that's it. I'll toss and turn and nothing can get me back to sleep again for at least three or four hours. Despite my exhaustion from the early morning and the travel and the time on the treadmill, this was one of those nights.

I flipped on the light and cracked the laptop open, and fired up a VPN service I subscribe to which would allow me to surf any part of the web in a way that no one could to track my movements or my browsing history. I researched jack and jill clubs. There weren't any. It seemed that a few places had tried, but failed, to maintain an authentic co-ed masturbation club, but they'd never lasted very long. So I changed the search to jack off clubs and hit paydirt.

From what I read online, the biggest and most established jack off club was right here in New York City, maybe a dozen blocks from my hotel. I kept reading. You have to be nude, though you should keep your socks and shoes on. It was all about guys openly jerking off, or even jacking each other off. Was it a gay club, or straight?

I scratched around the web for a while and it seemed to be a mix. I am straight and have never had any attraction to other men, and the idea of anal sex with a man was repulsive to me. But a circle jerk seemed harmless, and I was encouraged by the club's policy of "no insertion of anyone's anything into anywhere." Strictly no oral and no anal—mouths and asses were off limits. Should be safe enough.

In my search for information about the jack-off club I found a forum for guys, straight and otherwise, who seemed to have an obsession with masturbation. There were hundreds of active members who discussed techniques, turn-ons, turn-offs, favorite jack off locations, and the best porn. They posted videos of them getting themselves off, exchanged Skype addresses, and there were jack-off-buddy personals.

Masturbation was a fixation with them, and so was playing with their ejaculate. They competed for the number of times they'd come in a day, how many times they'd rubbed one out in the john at work, and how long they could go on the brink of an orgasm without actually coming. Edging, they called it. Many were married and their wives either supported or hated their infatuation, and some hid it from their partners altogether.

It was an addiction for them, and playing with their cum seemed to be a popular fetish. It made for fascinating reading.

Many of the forum members had been to the New York jack-off club and gave it high praise.

Back to the club's web site, and I learned that they met on Sundays and Tuesdays, and the next Tuesday meeting would be a special Halloween event. Every person was to wear a Halloween mask that would cover their faces completely, but was not allowed to cover their bodies below the shoulders. Nudity was apparently a requirement, notwithstanding Halloween.

I checked the calendar on my phone. The Halloween meeting was tomorrow.

I took a double-dose of melatonin and fell asleep to visions of guys walking around nude but for their face masks and shoes, masturbating in front of each other.

Weird.

The majority of the next day at work was spent walking Jonathan P. Mountford III through the higher concepts of program and project management. Mountford had been a mediocre project manager for a few years. Someone in the executive row had read in the Harvard Business Review that the best corporations in America were managing their key programs through project management offices, or PMOs. The company did a tiny bit of research and created a PMO, then promoted this pedant from project manager to PMO director.

In fairness, they recognized that he would need help and engaged me to advise him on the establishment of the new department. My task was to select and implement the most appropriate methodologies, recommend policies and procedures, handle a bit of business process realignment to accommodate the new systems, get him started on their first project, and generally, make Mountford look good. The problem was that the twerp had delusions of competence and was convinced that he didn't need me.

The work was as boring as hell, but it put bread on the table.

The biggest challenge was Mountford himself. He had a know-it-all attitude, and worse, he conducted every aspect of his work life according to his personal interpretation of the church's religious doctrines. We were grinding our way through a deck of slides I'd compiled examining the pros and cons of Agile versus waterfall methodologies, and he wasn't getting it. And in the middle of my explanation he interrupted: "Let's pray for guidance".

My jaw dropped for an instant before I caught myself, and agreed. He was the client, and I'd been a consultant long enough to know that you always have to accommodate your client's foibles.

Later, we were talking about specific membership scenarios in his health insurance systems, and I raised the complications of handling divorced couples.

"We're a Catholic institution," he interrupted, "and we don't condone divorce."

"I understand, Jon, but-"

"Jonathan," he corrected.

"I apologize. Jonathan. But the reality is that these situations will exist in your membership, and-"

"Did you read my inspirational? The one I sent yesterday?" Didn't this guy get it? If he would shut up and listen to me, I could turn his new little department into the shining jewel of the corporation.

"I did. Very interesting."

"Are you married?"

None of his fucking business, I thought. Was he going to ask about my sex life next? But I answered anyway. "Twenty two years. And you?"

"Of course." His answer was curt, as if I had no business asking.

"So on the setup of these membership scenarios-"

"Did you read the whole inspirational? Everything?" Johnny was good at interrupting, not so good at listening, and I was getting pissed off. This was going to be another long day. "You know the church does not accept extra marital activity, self-pleasure, or any other unconventional behavior." Jesus, I thought, this guy had some real issues.

I put on the most professional tone I could muster. I hoped it came off as calm but firm. "Jonathan, I've been married faithfully for more than two decades. I read your notice. Thank you for the inspiration, I appreciated it. My personal life is just that. Personal. I'm here to help you get this PMO on the road. Did you have any questions about the membership project?"

There's a saying in my business that a consultant's standard lunch is coffee and a banana at the desk. But at lunch time today I had to get out of the office, as far away from Jonathan P. Mountford III as possible.

Three blocks away I passed a party shop, and stepped in just for the hell of it. The place was packed with Halloween costumes for kids and adults. My eye was caught by four costumes at the back, for the four members of the rock band Kiss. As a high school kid I'd played guitar in a garage band. I picked the costume that was supposed to represent the original Kiss guitarist, Peter Criss. They wouldn't let me take just the face mask, so I had to buy the whole thing. They packed it in a plain shopping bag and I went off to look for something better than coffee and a banana.

In a deli across the road from my client's office I sipped at an iced tea and gazed at the package I'd bought. Would I really go through with this? Was I actually going to a jerk-off party tonight? What the hell was I thinking? And what would I tell my wife?

I recalled Mountford's "inspirational" notice, which he'd repeated this morning, and smiled to myself. "The church frowns on self-pleasure", yet I was thinking about taking self-pleasure to the nth degree. Was I considering this precisely because of Mountford's so-called inspiration? Or was it because Deb had joked about it and, horny dog that I am, I was turned on by another sexual outlet? Or was this a gay thing?

I almost choked on my iced tea at that last thought, and chills went up my neck. I am as red-blooded all-male as the next straight guy. But tonight's party was intriguing.

No, this was just self-pleasure, as that popinjay across the road calls it. It's something I do several times a week and this was just taking it to the next level.

I had an opportunity to break away from my client for a while that afternoon, and opened the jack-off forum on my phone. As I scrolled through the discussion threads I realized that I wasn't nearly as infatuated with masturbation or the cum-play fetish as the members of that forum. But, probably like any normal American male, it was something I did a few times a week. And that made jacking off a big part of my life.

I managed to get out of the office at a decent hour. I grabbed a bite at the hotel, went upstairs to call Debbie, showered and dressed, and slipped two little blue pills into my pocket. I always keep a few in my shaving bag for when Deb and I travel together. I tried on the mask. It was a full hood, with big holes for the eyes and ears and for breathing, and seemed quite comfortable. A cab dropped me off at 26th and 8th.

I got out of the taxi across the street from the club, and stood there. A bus pulled up, and I realized I had retreated into a bus shelter. I shook my head at the driver and waved him on.

I am pretty decisive by nature, so why was I hesitating?

A man came from the parking facility behind me, crossed the road and entered the building. Just a normal looking guy in dress pants, open necked button down shirt, and a sports jacket. A clone of myself, I mused. What brought him to a jack off club? Was he gay or straight? Married or single? Was he one of the guys from the forum who seemed to be infatuated with masturbation? Or was he just another male, like me, with a curious mind and a healthy sex drive?

The entrance was unremarkable in a street lined with a veterinary clinic, cleaners, a nail salon, and low-rent office space. After ten minutes I saw what looked like a typical cross section of New York's male population enter the building. About a dozen people with ages that seemed to range from the late twenties into the sixties. They were tall and short, athletic and out of shape, well dressed and casual—and by appearances, most were from the upper middle class. Perhaps the only thing they had in common was a healthy male desire to take their masturbation to the next level.

What would I tell Deb if I went in there? We kept no secrets from each other and she was very open about sex, but would this be too much for her to handle?

I should walk away. Take a cab to a strip club and get a lap dance. Go and jerk off in my room, perhaps edging for a long time, the way it was described in the forum. Go to a cigar bar and light up a stogie and get hammered on single malt scotch.

I crossed the road.

Check in was smooth. I paid and was ushered to an area where I was directed to undress except for socks and shoes, and put my phone and my money clip into my socks. I dry-swallowed the two little blue pills, pulled on my Kiss guitarist head mask, and went to join the Halloween fun.

Debbie and I are nudists and we've been to nude beaches and clubs all around the country. I'd been in countless locker rooms and gyms where men walk around naked. The nudity didn't worry me. Yet I was shaking like a leaf.

Thank God for the mask. I probably wouldn't have done this otherwise. Not only was the anonymity assuring, but the fact was that in my professional capacity as a management consultant to some of my industry's most senior executives, I had to keep my nose clean. No scandals, real or imagined, could be allowed to ruin my reputation.