The Northport Charity Masquerade - Cover

The Northport Charity Masquerade

by bpascal444

Copyright© 2025 by bpascal444

Fantasy Sex Story: Bobby gets a ticket to the most exclusive, expensive event in town, The Northport Charity Masquerade, an invitation-only revel that has fueled salacious rumors for years. Are they true or not? It has an unexpected twist that leaves him stunned.

Caution: This Fantasy Sex Story contains strong sexual content, including Ma/Fa   Consensual   Drunk/Drugged   Heterosexual   Fiction   High Fantasy   Brother   Sister   Gang Bang   Group Sex   Orgy   Anal Sex   Analingus   Double Penetration   Exhibitionism   Facial   Masturbation   Oral Sex   Voyeurism   .

Preface

WARNING: The material herein is completely fictional, a fantasy, and is intended as ADULT entertainment. It contains material of an adult, explicit, SEXUAL nature. If you are offended by (or it is illegal for you to read) sexually explicit content or language, please DO NOT read any further.

As in most fantasy, we gloss over all the possible exposures to STD’s from unprotected sex.

All characters in the story are fictitious; any similarity to any persons, places, individuals, businesses, or situations is purely coincidental.

I’d appreciate your comments.

“You did not get one! Nobody gets one except the rich and famous!”

“But I did get one. I did a favor for a guy. He always gets two, for him and his wife, but he’s got some last-minute work thing which is going to take him out to the coast, so he can’t make it.

“I could see it nearly killed him to give up the invitation but it would go to waste otherwise, so he asked me if I wanted it. I forgot to ask him if his wife’s still going to go. That’d be awkward, if I wound up hooking up with his wife.”

“Jesus, Bobby, nobody I know has ever gotten an invitation to the Northport Charity Masquerade. I don’t even know anyone who knows someone else who’s gotten an invitation! All I’ve ever heard is the rumors. Dude, you have to promise to tell me everything! Every detail. Do you think you could sneak in a camera?”

“Where would I hide a camera, Bucky? Seriously.”

“I am so jealous, man. What I would give to be in your shoes!”

I just smiled.


Truth is, I was feeling just a little smug. A couple of days ago, I was in Bucky’s place. The closest I’d gotten to this legendary event was rumors. And those mostly third-hand, ‘cause I’d never met anyone who’d personally gone to the Masquerade. I mean, other than this guy I’d done the favor for, and we weren’t really close friends, so I’d never gotten the dirty details first-hand.

The background was pretty well known. It was an annual charity affair, meant to raise money for various local organizations, and naturally they concentrated on inviting the well-heeled and well-connected, who could be depended on to open their checkbooks.

It began as a typical dinner-dance affair, pricey, predictable, a little boring. To “liven it up” they auctioned off a variety of items donated by local businesses. Everyone went home as early as they could gracefully manage, having fulfilled their charitable obligations.

A few years in, and they were having trouble even getting the dependable participants to commit to attending another year. There was, I am told, some pretty vicious infighting among the organizers, looking for someone to blame. In the end, they agreed that it wasn’t going to work in the present format much longer, and a new chairperson took over.

She decided that it needed a bit more glamor, more pizzazz, more excitement and unpredictability. That way, they could charge more money for tickets. So it got a new theme. A masquerade ball, open bar, very exclusive. Everyone to be anonymous so nobody could be judged harshly for behavioral excess the next day, much like Mardi Gras.

And it was marginally more successful. The costumes were a hit, as was the open bar. And it turned out that alcohol had the unexpected side effect of making the auction bids more aggressive and reckless, so the finances actually worked out pretty well.

But the real turning point happened entirely by accident and changed the event forever. Once again, the alcohol turned out to be an important factor in the story. Nobody knows who the first one was because, well, costumes and masks. They were disguised. But some inebriated middle-aged woman who, legend tells us, was dressed as Marie Antoinette, was seated at a table with her companions when she was inspired to fall to her knees and give her dinner escort, dressed as a Scottish lord in a kilt, tam o’shanter and sporran, a blowjob.

At first it was politely ignored by the persons at her table who recalled their manners and continued to chat companionably amongst themselves. Apparently she was quite talented and before long her escort was moaning, not quite in control. Her butt was wiggling provocatively under the layers of petticoats, and that drew the attention of the curiously un-muscular Goliath, at the same table. He kept glancing at the swaying butt until he finally stood up and reached down to flip her skirts up over her back.

And found she was wearing no underwear. Best guess was that she needed some air circulation under those heavy skirts and decided that no one would notice. In seconds he was on his knees pushing his dick into her pussy. That was enough for Abraham Lincoln, also at the same table, to walk around and pull out his dick which she proceeded to stroke expertly.

It was hard to ignore now, as the tables weren’t that far apart, and the tableau drew spectators from nearby, some of whom were inspired to find a corner and a willing conspirator to start their own party.

It seems the anonymity was the key factor, aided and abetted by the alcohol. Mostly anonymous in their costumes and masks, such salacious excess could easily fall under the blanket of plausible deniability. No one knew who was humping whom. Participants could just pretend it had never happened and others would graciously go along.

Not everyone was on board. Many were titillated and secretly envious, but not yet ready to join in. Some of the older, stodgier money was horrified and shocked, and made a point of walking out in a huff.

But the day after, when the receipts were totaled, it was found that the evening had been an unqualified success. The auction had broken records, and a number of attendees had called to reserve tickets for the following year’s gala.

There were the usual complaints of “over the top”, “excessive”, “lewd and inappropriate”, but the money told the real story. The steering committee held an awkward post-fete review. Many of the old regulars had said they were appalled and never coming back, which was concerning.

However, the chairperson said that she had been fielding calls most of the morning from people who’d said that they’d been sorry to have missed previous masquerades, having been so busy with work, but wanted to make sure that they reserved the date for the following year. When was that again?

The number of new inquiries exceeded the number who had angrily withdrawn, so it was marked as a win. There were some moral misgivings about the ethics of hosting a sex party for charity, but the chairperson again read off the totals for this year’s benefit and the murmuring tapered off.

The takeaway from the review was that they would increase ticket prices yet again to insure that all who were there really wanted to be there. And it was decided to put a limit on ticket sales, because the increased interest in the event suggested that attendance might quickly exceed capacity. And perhaps look into some paid security, to make sure there were no uninvited participants and definitely no cameras.

The upshot was that us common folk were quickly priced out of the event, even if we could wangle an invitation. The invitations were directed to the well-to-do and the stinking rich, who were the only ones who could afford it anyway. Those were the folks who would cheerfully participate in the charity auction, which is where a good chunk of the take came from. So the rest of us, well, we could only trade rumors about it.

After a couple of years it became one of those events that only the glitterati seemed to attend, and the rumors about what happened there became more outrageous. I’m sure at least half of it was complete fabrication.

One of the things I know is true is that it was “protected”, meaning the police took a hands-off approach to that particular location on that particular evening. I know this for a fact because I had a high school buddy who became a deputy with the local sheriff’s department, and they got their instructions direct from the sheriff at roll call on the day-of. The office of sheriff is an elected position here, and a sizable donation to the re-election campaign appeared just after the event.

That also was sufficient to brush away demands for the authorities to crack down on the carnal depravity that was corrupting the community. “Sorry,” he said, “private property, private behavior, no jurisdiction.”

Same with the elected district attorney, who also received a hefty donation to his re-election campaign.

I also know that the committee was seeing what the market would bear, raising the prices each year, because I overheard a couple of well-dressed lawyer types talking about it quietly ahead of me in line at Starbucks. One said, “Geez, it’s a big jump from last year. It’s a budget stretch, but it’s not something I’d miss out on.”

I heard one quietly mention the price of the tickets and I gulped. That was what I might spend on a two-week vacation including a hotel and cross-country flights.

So maybe ten years on from that first one it had gotten to the point of people plotting for most of the year how to get on the invitation list, if they weren’t already on. It was difficult, because the Masquerade had reached maximum capacity and couldn’t add new people. They were now asking for RSVP’s from those invited, to make sure that they’d show up if they’d bought a ticket, because some people were willing to pay a premium to get an invitation.

Unless I made a fortune in the stock market, this was going to be my one and only chance to attend the Masquerade.


The invitation was last-minute enough that I had trouble finding a costume. Northport isn’t that big a place, and we really only had one costume rental place (which also rented tuxedos for proms and weddings), and the costume racks were mostly picked clean.

In the end, the guy said, “How ‘bout this? It didn’t fit anybody else, but it looks like it might fit you.”

I looked at it dubiously. It was a Roman centurion costume, a doublet with some fake chest armor, and a “skirt” which came halfway down the thigh. There was a belt which held a short plastic sword. There was a tin helmet painted gold with a face mask that in real life would keep a sword from slashing at the face. It completely covered my head. It didn’t look that comfortable, but when I tried the helmet on it wasn’t too heavy and had surprisingly decent air circulation.

“I suppose if that’s all you have...”

He nodded, and I pulled out my credit card. The guy must be making his year’s nut on rentals for this one night alone.

At home I put on the costume and looked at myself in the mirror. I suppose it could be worse. The costume itself didn’t look that bad, perhaps a bit on the tacky side, but I expected most everyone else’s would be almost as tacky. Costumes from Martell’s Formal and Party Wear probably didn’t meet the standards of the costume department at Paramount Pictures.

Still, there was a lot of money at play here, and I’m sure some of the attendees made a point of having the most dazzling and expensive costume. Itinerant centurion was going to have to make do for me. Let them snicker; I still got to say that I had attended the Masquerade!

I put on the helmet. It had a hinged faceplate that I could open if I needed to take a drink or eat something, and unless someone was looking at me face-on, I would still be anonymous. It was padded where it met my shoulders and didn’t seem to move around too much. My vision was restricted, of course, because I was looking through holes for the eyes and had little to no peripheral vision. How did centurions stop enemies from sneaking up behind them and cutting them open?

Well, hopefully I wouldn’t be faced with that particular problem at the Masquerade. I took the costume off and laid it aside until the weekend.


On Friday after work I got a call at home from my sister. “Hey, sis. To what do I owe this honor? You hardly ever call me except at the holidays.”

“I do so,” she protested. “Why, I just talked to you..., well, I can’t remember specifically, but it wasn’t that long ago. Anyway, I need a favor. Jack’s in Chicago at a client site -- again! -- and I just got called to sub for Darlene who was going to take a seminar on the upcoming changes to the software we use at work. She got sick and now she can’t go and we need the info from the seminar to plan for the changes.

“The thing is, it’s out of town and I’d have to stay there overnight. And it’s tomorrow and I’ve got nobody to look after the twins! Can you do it? I know it’s last minute, but I’m kind of in a bind.

“I’m really annoyed with Jack. He’s been doing a lot of these out-of-town trips lately and he leaves me to take care of everything else with the kids and the house, in addition to my job. I’m getting a bit fed-up. Anyway, didn’t mean to get off on that tangent. Can you do it?”

Damn. I was so close, and now I can see the Masquerade slipping away. I thought about it. I hated to leave her hanging, but I’d never get a chance to do this again.

“I’m sorry, sis, I’ve got something I really can’t get out of tomorrow. You know I wouldn’t normally mind at all, but I’m stuck, too.”

“Damn. Okay, it was a long shot anyway. I’ll see if I can call in a favor with Mrs. Sweeney next door. She owes me one. I better make the call. Talk to you soon.” She hung up, and I sat there thinking, “What else can go wrong?”

I’d been getting some vibes about Carol and her husband over the past few months, nothing specific, just some chips in the public veneer, some coolness between them. Most couples have that after a few years together. I suppose they’ll work it out, for the kids if nothing else.

I brought my thoughts back to the Masquerade, and the more I thought about tomorrow, the more nervous I got. I had only the rumors to guide me, and the rumors were outrageous and probably mostly false. I had no idea what to expect. In the worst case I would find that the rumors had no basis in fact at all, and I would spend the evening standing in small groups trading idle chatter with anonymous, masked people, drinks in hand. A masked cocktail party. Whoopee.

Still ... the rumors had been around for a long time, and people were still fighting tooth and nail to get an invitation. If the rumors actually were all false, then I would have expected them -- and interest in the event -- to die off over time. They stayed alive because somebody, somewhere, kept feeding the fire each year after the Masquerade with just enough hints of truth to start the rumors spreading again.

I forced myself to stop worrying about it. I would get there Saturday and find out soon enough for myself if it was true, or if it was just wishful thinking by those of us who had been previously excluded.

To make matters worse, I had seemed to have caught a minor bug, mostly sniffles and a sore throat which left me a little hoarse. It didn’t seem to affect my energy, however, and I suppose it would turn out to be nothing more than a minor annoyance.

The rest of Friday night seemed to flow exceptionally slowly. But Saturday arrived in due course, and as afternoon turned into evening I took a shower and dressed.

I felt a little silly taking the elevator from my apartment down to the parking garage dressed as a Centurion, car keys in hand, so I pulled on a pair of sweatpants and tucked them under the armored “skirt”, then put on a raincoat that came down to my ankles. The forecast had said ‘chance of rain’ anyway, so it couldn’t hurt. I tucked the helmet under my arm.

I kept the helmet off as I left the garage because it would make driving a challenge with its limited peripheral vision.

The event was at the most selective of the various country clubs that dotted the area around Northport. The rumor mill had told me that the members had initially been a little miffed at being told that the club facilities were off-limits on this one particular day, but a few well-placed invitations to the more highly ranked members had quelled the dissent.

I had made sure that I arrived after the stated start time to make sure that things had gotten underway. Turning into the parking lot I saw signs saying ‘Show your invitations before parking. No entry without an invitation.

I hadn’t put on my helmet yet, so I was exposed, so to speak, but the parking attendants didn’t seem to care about who we were, just whether we had an invitation. I flashed the card and got a nod, and he pointed to where I was to park. The lot was already half full, but another attendant directed me into a space, then moved on to the car behind me.

My mouth was already a bit dry, but I tugged off the sweatpants, checked myself in the rear-view mirror and stepped out of the car. I could see that the weather report had been correct, and the sky was threatening, full of clouds.

I took off my raincoat and tossed it on the front seat, put on the helmet, and headed toward the entrance of the main building, invitation in hand. I was wearing a small leather pouch on my belt, where I’d put my wallet and driver’s license and which also contained the car’s key fob. It wouldn’t do for this centurion to have to walk home.

The building was large, and I knew it was the site of many society weddings and other functions. There were separate buildings with locker rooms, a pro shop for the golf course, and an enclosed pool.

There were others moving toward the entrance, from this and other parking areas, all dressed in a variety of costumes, and all masked. I saw a couple of ballerinas, one way past her prime, a Rambo, one who I thought was Luke Skywalker on his fiftieth birthday, and the ever-popular fairy princess, accompanied by a doctor. Who knows, it might even have been a real doctor! Maybe he came here straight from the operating room, still wearing his mask and scrubs, anonymous!

I looked around as I approached the entrance, as I’d never been here before. I saw some heavy-set guys in blazers carrying hand-sized radios roaming the perimeter in pairs, occasionally answering some call on their communications equipment. Now that I’d noticed those two, I started seeing them everywhere around the building. They were always moving, always looking.

There was a backed-up line at the entrance as each couple was asked to show their invitation. Women were asked to open their purses, as were men if they were carrying something that could hold a camera, and everyone was asked to leave their phones at the door, for which they were given a numbered receipt. Everyone seemed fine with this, joking with the staff about missing the chance to make a fortune selling the photos to The Enquirer. None of the staff found the jokes the least bit amusing.

Having received my nod, I walked in and stood for a moment, looking at the surroundings. There were two large rooms to either side of the entrance hallway, and both seemed packed, echoing with loud voices and laughter. In the right-hand room, I could see a makeshift bar on the far wall, two bartenders (both masked) being kept busy with drink orders.

The costumes were pretty much what I’d expected, the kind of thing you’d typically find in a costume shop. I realized as I looked that I’d never before been to a costume party of any kind. Maybe they were only popular in a certain economic group. There were a lot of television and movie stereotypes in evidence, including several masked cops in ill-fitting uniforms, and someone who looked like he was trying to pass as TV’s Columbo in a soiled raincoat and fedora, also masked.

There was a paunchy general, either Patton or Eisenhower, I couldn’t tell, and a very impressive Queen Elizabeth I. She’d have trouble getting out of that costume if she wanted to jump the general. Against the wall Cinderella was chatting with Darth Vader and The Lone Ranger.

In the middle of the room I saw Evel Knievel in his white jumpsuit and cape, covered with stars, wearing a motorcycle helmet with a shaded visor. He was facing me and talking to a woman who I thought was meant to be the storybook Heidi, dressed in a dirndl. She turned to wave at someone across the room and I saw she was masked, but her tits were hanging out of the top of her dress.

So perhaps the rumors weren’t totally bullshit.

I was impeding traffic flow through the entrance, so I stepped into the room to my left to give it the once-over. It was pretty much like the other room, though here the bar was along the nearer wall. There was a crowd there, too, waiting for their drinks.

With the helmet on I really had to move my whole body so I could see around me. I had to admit, there were some clever costumes here. Some people had obviously put a lot of thought and money into dressing up properly; these weren’t rentals. There was one woman who was dressed as a queen -- I couldn’t tell which one -- and that was no rental costume. I was pretty sure she’d had that made to order.

Not far away was a man dressed, I thought, as Henry VIII, and his costume appeared custom-made as well. I wondered if he and the Queen were a couple.

I looked to my left, back toward the door I’d entered. In the corner was a large potted ficus tree. Beside it, Snow White was on her knees giving Robin Hood a blowjob. He had his eyes closed and his hands on her head, and she kept pushing them away so he wouldn’t muss her special Snow White hairdo, which looked remarkably like the one in the Disney cartoon.

Okay, the rumors are starting to look more credible all the time. And it’s still early.

A young waitress wearing the typical black skirt/white blouse waitress uniform was passing among the crowd, carrying a tray of canapes. She was wearing a mask that covered the top half of her face, but I could see enough of her lower face to tell that she was blushing. I could imagine that this was not her typical caterer’s shift handing out appetizers for golf awards night at the country club.

I could also imagine that she was getting paid a serious bonus for hazard pay and sealed lips, so she’d put up with whatever embarrassment she might be feeling. She gave me a practiced smile and leaned the tray toward me, as if to ask if I’d like one. Without thinking, I took one, and as she moved off I realized that I had no easy way to get it into my mouth. There was only a tiny hole where the mouth should be, enough to allow my voice to be heard.

I thought about tossing it in the potted plant, but I was hungry, so I moved casually to a corner, faced the wall and loosened my hinged faceplate. I don’t think anyone could see me, and I popped the canape into my mouth and locked the faceplate back in place.

I turned around to face the room again and saw that Snow White was wiping her mouth and Robin Hood had collapsed against the wall, waiting for strength to come back to his legs. Snow White got up and wandered off.

I noticed that the crowd had thinned at the bar and, having had the appetizer, realized I was thirsty. Maybe something stronger to help calm my nerves. The bartender looked at me inquiringly through his mask and I ordered a whiskey sour. “Coming right up,” he said as he grabbed bottles and glass.

I looked around while he worked. To my left, in the far corner next to a door leading to some other room, was a side table with a lamp. The lamp was wobbling, because Annie Oakley was bent over at the waist, holding on to the table, her fringed skirt tossed up over her back, and behind her a plump Friar Tuck had parted his robes and was pounding an impressively thick dick into her while he grabbed her hips.

I thought it was a good costume choice for him, as the loose robes hid his extra pounds, and the bald spot on his head looked almost like Friar Tuck’s tonsure! The effect was incomplete because I could hear him, even at a distance, reciting a distinctly un-priestly homily: “Shake that ass, bitch. Grab that dick with your tight little pussy!”

“Here you are, sir. And may I suggest...” The bartender left the comment unfinished, but extended a straw to me along with the drink. I nodded my thanks and saw, approvingly, that it was a flexible straw, so I could bend it to fit through the mouth-hole in the mask. Obviously not their first time at this event.

I finished half the drink, wandering aimlessly around the room, trying to appraise the people gathered at the various tables. I could see almost nothing of their faces due to the masks, but the body language was unmistakable. These were people comfortable with being here, surrounded by others like them. There was a sense of the power and comfort that big money affords.

They could probably sense that I was not one of them. I might be new money, if they bothered to wonder about me at all, but if I was, then the money was too new for them to have to think about how to fit me into their world-view. They were comfortable with each other, even if they might not know just who was beneath each costume.

At the closest table, a pretty good likeness of Ben Franklin was talking to Betsy Ross. I had to look closely; Ben’s hair was actually a kind of wig incorporating Franklin’s long, shoulder-length hair as well as a synthetic bald spot. That couldn’t have been cheap, probably custom-ordered.

I knew it was Betsy Ross, as her costume had a partially finished 13-star flag sewn into the lap of her dress, as if she’d just stopped working on it. Her hand, now not stitching on another star, was instead moving under the table in Ben’s lap.

At the next table, various characters were chatting among themselves, while Peter Pan had his tongue halfway down Wendy Darling’s throat. He had worked one breast out of her Edwardian dress and was rolling the nipple under his fingers. It didn’t look like it would be long before the two of them were on the floor.

For the hell of it, I went to the first room I’d looked into when I came in the entrance. It was pretty much a mirror image of the last room, just with different people. This room had a small couch and two armchairs in a corner, where people might gather to talk, perhaps after a round of golf while they waited for dinner.

The Big Bad Wolf was sprawled on his back on the couch, butt at the edge of the cushion. He had unsnapped a closure below his waist so his erect dick could protrude. Little Red Riding Hood was sitting astride him, her dress pulled up to her waist, as he slammed his cock into her. She was moaning encouragement, “Do it hard, baby, just like that, make it hurt a little!”

In one of the armchairs next to them, George Armstrong Custer was watching them closely, perhaps hoping for his turn.

There was a kind of voyeuristic pleasure in watching other people get it on, like watching porn, but there was so much going on that I was afraid I’d miss something important, so I turned away. Against the next wall Dorothy Gale from The Wizard of Oz was talking to Superman and Aladdin as they sipped their drinks. Aladdin had his dick out and Dorothy was stroking it enthusiastically with one hand as she made a remark to Superman, which made him laugh.

I hadn’t worn a watch, as I couldn’t find one that would be period-correct for a Centurion -- perhaps a miniature hourglass on a wrist strap? -- but I had caught a glimpse of the bartender’s watch when he handed me the straw, and it was not yet ten o’clock. I wondered what this place would look like in two more hours.

I wandered back to the hallway and noticed an ascending stairway I hadn’t seen before, because the stairway was oriented away from the entrance so people went upstairs facing the front of the building. The only reason I was aware of it was because a costumed couple was just going up the stairs, their hands all over each other. Is there more upstairs? Curious, I followed them up.

Yes, there were several hallways on the second floor, with a series of doors just like a hotel corridor. Now that I saw it, it made sense, like the posh clubs that wealthy gentlemen used to belong to where they could take dinner or even stay the night if the workday ran late and it was too late to head back to the suburbs. Why wouldn’t an exclusive country club have the same kind of amenities, considering what members must have been paying in annual dues?

The couple I was following stopped at a door and knocked twice. I caught a glimpse as the door closed behind them. It was already occupied with at least two other couples. I couldn’t tell what costumes they had chosen because they were all stark naked and half drunk.

Okay, let’s see, so far I’ve seen a blowjob, handjobs, straight fucking doggy-style, cowgirl, some mild voyeurism, plus group sex. I’d pretty much put the rumors to bed. This was the real deal.

As long as I was here, I walked the rest of the corridor maze. This was probably the only time I’d get to set foot in this particular country club. I couldn’t afford the dues, even if they’d have me, and I didn’t know anyone who’d invite me as a guest. Different social circles and all that.

As I turned into the last corridor, I saw two women chatting in the hallway, drinks in hand. One was Jeanne d’Arc, I thought, and the other I was pretty sure was either Mary Poppins or Eliza Doolittle. She was wearing a neck-to-heel shirtwaist dress popular at the turn of the twentieth century, with the iconic black wide brim bowler hat that Julie Andrews made famous.

 
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