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Chapter 82
by
caitlynmasked
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Chapter 78 – Charity guessing
Being paraded out in front of a well to do audience with my arms bound, mouth gagged, and ass plugged, has to be one of the most humiliating acts I’ve ever lived with. Blowing Darnell, at Trixie’s, in the theater, and at the office, are all up there, but only two people witnessed me doing that and both of them assumed I wanted to do it. This is different as I’m being shown off to dozens of people and they’re not shy about the fact that they’re ogling me and my seven handmaid sisters. I try every trick I know to slow my heart down, to calm down even a little bit, to get control of my raging emotions, but there is no action or motion that I can perform that isn’t reminding me of what’s happening. I see something that I want to look at but as soon as it’s past my blinder bonnet, I can’t turn to look at it again. I’d like to stop and walk back, but I’m being led by a leash that is easily removable and impossible to remove myself. I’d like to not walk like some fashion week porn star with my ass pushed out and my tits about as proud as they’ve ever been, but between the ballet heels, the arm binder, and this damned plug, I can’t present myself any other way.
My limited view is almost entirely filled with the handmaid in front of me, but what I do see of the guests is people dressed dramatically, perfectly, and extravagantly. There’re cops and robbers, cowboys and Indians, chefs and waitresses, Peter Pans and Tinker Bells, kings and queens, Batmen and Catgirls, and of course school girls and football players. It took me a bit to find Art and the other dates for the handmaids, but I finally spotted the costume. A commander’s outfit from the show. Subtle but obvious if you know what you were looking for.
I have to assume that many of the guests are used to this gathering of handmaids for whatever auction our ‘aunt’ was talking about as the crowd slowly quiets down and watches us slowly but methodically get matched around the room. Some of the bolder guests even approach the handmaids and feel them up, joking with them the entire time. I notice that none of the handmaids offer any resistance or even react too strongly to their public molestations, but then I remember how we’re all bound. There’s not much we can do, physically or verbally, to react. I personally get felt up several times with the men making appreciative noises as they cup and hold my breasts. During one of these times while a man with very strong whiskey breath is laughing and rubbing his thumbs over my nipples, I notice one of the commanders try to approach the handmaids. He’s quickly stopped by the staff, which are easy to identify as they’re all wearing grass skirts and masks and nothing else, and led away.
Eventually when we’ve shown off enough, we’re circled around the center of the dance floor. A group of grass skirted men walk behind us, placing a plush red velvety pillow in front of each of us. When we all have our spots laid out, the men return and help us all kneel atop the pillows. I’m still not sure if the audience knows just how bound we all are as the staff guys seem to help us down with a grip that looks like it’s taking a hold of one of our arms. When we’re all finally down, I see across from me that the guys are again circling around us, this time gently pushing our heads forward. I’m sure they’d want to do a ‘nodding’ pose that would similarly keep our vision even further limited, but with the posture collar this is as close as they can get. The man behind me is gentle but firm. I can’t’ help but at least try to resist but it seems like he barely notices as I’m pushed into the position he wants.
I don’t know how long we’re kept waiting like this but after just a few minutes it seems like too long. I hear the occasional grunt from one of the other handmaids and wonder if they’re able to at least lean back and kneel in a more comfortable position. When I try it for myself, I make a little grunt of my own but then realize what exactly I was hearing from my sisters. Not the grunt of effort from getting out of this uncomfortable position, but the grunt of being **** back into it. I kneel comfortably, if it’s possible for any kneeling to be truly comfortable, for only twenty or so seconds before I feel one of the staff behind me, again gripping the back of my head and pushing me back into the uncomfortable forward position.
One thing I learned from that experience is that any further attempt to get out of this position would be futile. I might be able to push back far enough to get my ass to touch the floor, but with these ridiculously tall heels, I’d never be able to move into a standing position. We’re here until they don’t want us to be here. And with all the festivities and dancing going on around us, I highly doubt that will happen any time soon.
While it feels like we’ve been stuck in this uncomfortable pose all night I’d wager that it was closer to an hour and a half. An hour and a half of straining the muscles in our backs, abdomens, and necks, all while hearing people eat, drink, dance, and be merry around us. Eventually the party reaches a steady murmur. Not calm, not excited. Just a calm that would be nice to experience.
That’s when they come over and start lifting us to a standing position. I have only a moment to see the handmaids across from me with a new feature. The red hood attached to the back of their dresses has been pulled up over bonnets. Unlike the television show, however, this hood is long enough that their faces are now completely obscured. Once I’m standing and steady on my heels, my own hood is pulled up and over, leaving me with only a small sliver of floor that I can see.
Once I hear the remaining maids lifted to standing and having their own hoods pulled, everyone’s attention is drawn to an amplified voice. I’m almost sure it’s the ‘Aunt’ from earlier, “Ladies and gentlemen, may I please draw your attention to our center stage. It’s time for our charity auction. This year we have eight generous participants and their lovely dates vying to donate to our well deserving charity; The Chicago Center for Furthering Arts. Commanders, can I please have you all join me up on the stage and take a seat in one of our thrones.”
After a moment, where I assume Art and the other men dressed up as commanders make their way to the stage and comfortable sounding chairs, Aunty resumes, “I’ll be quick as there are only a few of you that haven’t had the opportunity to witness this event before. Each commander will get the chance to choose one of our lovely handmaids. Here on stage, they’ll get to inspect the maid in any way they’d like to. The only limitation is that they cannot pull the maid’s hoods back or in any other way look at their face. The first guess on a maid will cost ten thousand dollars. The next guess on that particular maid will cost an additional ten thousand dollars. We’ll continue until all eight commanders have correctly guessed their maid and are successfully paired up. Gentleman, we’ll go by the order that you’re sitting in and that means Mr. Johanssen goes first.”
Hearing alone doesn’t tell me much about what’s going on. I hear three different commanders called, each picking a different maid. There’s obvious enjoyment from the audience and their ‘oohs and ahhs’ but I have no idea what the commander is doing to earn such praise. And of course I can’t hear anything from the handmaid herself. Soon enough a Mr. Smythe picks me, and I learn I’m lucky number seven. Someone takes a hold of my leash and leads me slowly to the center of the stage where I hear the steps of someone with hard soled shoes approaching me.
My hope is that Art will make me his first pick, even though I’ll now go for twenty thousand dollars. I’d wager that even in these dresses that are now obviously designed to hide our body shapes and obscure any identifying information about us, my breasts are still visibly larger than any of the other handmaids. If so, I should be an easy pick.
Thoughts of Art leave my mind as I feel Mr. Smythe, or at least what I assume is Mr. Smythe, placing his hand on my belly. I stiffen only for a moment as I’ve been touched enough in jokingly intimate ways at the office that any embarrassed reaction has been burned out of me. Even as he draws his hand around my hip and around the curve of my ass, to the appreciate sounds of the audience, I don’t blanche or jerk. My only move is when he removes his hand and returns it suddenly in a slap. The slap to my ass is nothing compared to what I receive from ‘my guys’ or anybody at work, but it’s still enough to almost push me off balance on these stilts I’m wearing. That at least earned a little laughter from the audience.
I get a hint of how this charity part of this works when Mr. Smythe jokingly declares, “Well my wife of twenty-five years may kill me for saying this but she doesn’t have as slappable ass as that. I’ll still guess that this little Philly is my Phillis.”
Even knowing I wasn’t his wife, he still guessed. He still upped my price by $10,000. And he more or less invited the other commanders to give me a try. As I’m led back to the other girls and another commander starts his guessing, I finally get it. While ten-thousand-dollar guesses sounds like a lot to me, this party is filled will millionaires and billionaires. This would be like them paying a buck for a feel. They get to submit a comparatively little amount of money to a charity and in return get to publicly and acceptably physically **** women. Women that I assume agreed to it and weren’t just presumed to be a whore who was being paid to participate.
I lose count of how much the charity makes or how often the other handmaids are called. Somehow it seems that word gets around to the commanders what I feel like under my dress as I’m picked easily twice as often as the other handmaids. I get almost every part of my body felt up, rubbed, caressed, and otherwise touched intimately. When Art picks me on my fifth trip up to the stage I let out a long sigh of relief as I’m about to be freed from all of this. Art does his part and feels me up, though not nearly as aggressively as any of the previous four commanders and ends up behind me with his hands cupping my breasts.
When he whispers in my ear, however, my stomach drops, “Hey, I’m having a blast and wanted to check in with you. If you want to stop, just say so and I’ll guess it’s you. But if you’re having fun as well, stay quiet and I’ll guess someone else.”
I don’t even try to speak knowing I couldn’t make enough noise to be heard, let alone understood. Instead, I try to wiggle in Arts grip and rub up against him forcefully, anything to indicate I don’t want to stay here. As I feared though, my message doesn’t come through. Art’s voice is full of mirth as he calls out, “Nah, this can’t be my Paris. She isn’t nearly this feisty!”
The commanders continue to pick me at a prodigious rate and get more creative ways to ‘inspect’ me. One brings out a chair so he can sit down. It takes two staff members to help me lay across the man’s lap so that he can give me five actual spanks. He later said his wife would wail like a baby, so I couldn’t be her. But of course, he still guessed that I was. Another commander, reeking of gin, stands behind me and bends me forward, one hand on my shoulder, the other on my hip, as he makes a show of dry fucking me for several long moments. I actually feel the hard on in his pants bouncing off my generous and by then stinging ass. I’m not sure if he’s too drunk to notice or if he actually believes his girlfriend has an ass like mine when he guesses I’m her.
When Art finally guesses that I’m his girlfriend, I’d been on stage nine times. Art paid one hundred thousand dollars to finish the game, as I was the last girl up there.
One of the grass skirted staff help me back to Art’s table where I’m gently sat down in his lap. She then makes a bit of a show in pulling my hood back and removing the bonnet. Unfortunately, she leaves the facial covering which hides the posture collar and the gags. I hear her whisper in Art’s ear that my arms are bound behind me and that I’m wearing ballet boots, so he has to be careful and hold me securely. Art then puts his arm around the small of my back and takes hold of my hip. I sadly doubt that he knows he’s pulling my hands closer to my own back, pulling my shoulders further back, pushing my breasts further out.
I have work diligently to remain balanced in Art’s lap. It’s not that he doesn’t try to keep me safe, it’s simply that he doesn’t know how. Mal? Darnell? Hell, any of the guys at the office? They’d know how to hold me so that I could relax a bit on their thighs. Plus, Mal, Darnell, Frank, and Thomas, the guys most often having me in their laps, are all at least twice the size of Art. I’m not sure Art has the upper body strength to stop me from tumbling off his lap if I weren’t actively trying to stay there.
With me spending so much time and energy at staying put, I have no idea how much time has passed. It could be late evening, or it could be nearing dawn. I just don’t know. I’m barely even aware of the conversation Art is having with the other people at his table, except that they spent a long time talking about the nightmares of yacht ownership.
When the Aunty comes back, she stands right in front of me and bends forward, hands on her knees, so that she can look in my eyes as she addresses Art, “Sir, our costume designer is leaving for the night and wanted to make sure you were satisfied with your and Paris’ costumes. At this point though, you’ve only seen half of it. Would you like to see the Paris’ less than puritan look?”
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You're Not The Boss Of Me
Going undercover as a secretary backfires for poor Paris
Paris agrees to help his apartment mate Grace help
Updated on May 10, 2026
by caitlynmasked
Created on Aug 26, 2025
by caitlynmasked
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