Chapter 84
by
caitlynmasked
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Chapter 80 – Serving for Art, Toying for Grace
Sitting on the edge of the bed in a room set up specifically so the guests can fuck after an exciting and stimulating party, dressed up in some of the sexiest, or at least raunchiest, lingerie I’ve ever worn, and still having the nipple stimulators work at full blast is leaving me quite aroused. It doesn’t matter that I didn’t choose any of this. It doesn’t matter that I’m with a man that I didn’t want to go out with. Not that I want to go out with any man, but still. It doesn’t matter that my arms are still filled with pins and needles and that I don’t feel that I can speak as numb and weak as my tongue and jaw are. It doesn’t matter that I had an orgasm earlier.
No, I’d be lying if I said I wasn’t turned on.
I’d like to think that if Art tried anything, I’d have been strong enough to push him away or at least step away myself. But with as on edge as I feel and as aroused as I am, I’m not sure I could have put up any fight to something that might lead to sexual stimulation. Thankfully I didn’t have to put that thought to the test as Art seemed to innately understand that he was unwittingly used in a farce against me. As good intentioned as it might have been, he wasn’t a part of it and was therefore a patsy in my torturous night. He also seems to understand that I’m weak and **** as he steps out of my view for a moment and returns with one of those big overly fluffy white bath robes that you find in high end hotel rooms. After gently wrapping it around my shoulders and folding the front around my breasts, giving me at least some of my modesty back, Art puts his arm around my shoulder and gives me a weak hug.
Even in this moment of vulnerability, I can’t help but compare Art to Mal and Darnell. Mal and Darnell would both hold me tight and make me feel protected. I think Art is trying to do that, but he doesn’t have the confidence in himself to do it right. Instead, he’s hugging me like a shy guy would. After a few minutes of us sitting silently while I work at my jaw and flex my arms, Art stands up and starts pacing.
I can see that he’s been fuming this entire time and doesn’t know what to do, even as he tries to work it out verbally, “This can’t stand. I won’t let it stand. They have to… I don’t know… pay? You must know, Paris, that I didn’t understand what was going on. They told me you were into some kink and would like to be a part of their charity guessing game. I can clearly see that you wouldn’t want this. Or, er, that you didn’t want this. It’s wrong. It’s imprisonment. It’s **** and battery. I’ll have my lawyers sue the heck out of them. No, I’ll march downstairs and find the couple that own this place and demand… uh… I’ll demand that they come up and personally apologize to you. I’ll threaten them with the lawsuit. Or, I’ll have them apologize AND sue them. No, that won’t work. Or, maybe they didn’t know and this was all just their servant’s fault. But if it was, I’d…”
I try hard not to giggle, even though Art’s response is funny. He has more money and clout than he knows what to do with and yet he has no idea how to present himself. From their interactions I know that Mal and Darnell would act the same whether they were rich or not. Money didn’t give them power; it came from deep within themselves. Art has been given every advantage and still doesn’t have that power. In my head, I can hear Mal’s instructions for tonight and now they make more sense. He wanted me to have fun with Art and even called him a puppy. He didn’t want me to ‘overdo’ it or make Art feel small. Mal wanted me to defer to Art, laugh at his jokes, and play the part I do in the office which is complex but boils down to something simple… make Mal look good. Out here on this date, Mal wants me to make Art look good. Mal even said that Art might want a hand job but joked and indicated that that would be the extent of Art’s sexual prowess. And now I’ve seen evidence of that.
So, while I’m in no particular mood to offer comfort to anybody, seven months playing this part has made it easy to slip back into my role. Standing up I flex my arms again. While I won’t be able to work out in the gym for the rest of the night, I can at least move them without looking like a marionette. Working to balance on the ballet heels, I walk up to Art and slowly put my arms on his biceps, turning him to face me. Looking up at him I **** my lips into a smile. Not exactly an easy task, but one that I know I can accomplish. When I see that I have Art’s full attention, I don’t think about what I’m going to say and instead just go with what my gut offers. I want to make him feel better about himself, make him feel big and strong, and most of all make him feel appreciated, “Art, I can’t say how touched I am that you want to get even for me. That means the world to me that a powerful man like you would protect a little secretary like me.”
I can already see the blush forming on Art’s cheeks and go in for the killer move that will wrap him around my pinky finger. I lean forward and place a kiss on his lips. Compared to how I’ve been kissed by Mal and Darnell, by Grace and Trixie, this is really nothing more than a quick peck. Art’s and my mouths barely open and our tongues barely touch. But it’s clear from his reaction that this is much more to Art. When we part, I stay close and continue talking to him in an almost conspiratorial whisper, “Look, tonight wasn’t comfortable and you’re right, I didn’t want it to go that way, but there wasn’t any harm or foul done. Why don’t we build upon what happened instead of blowing it up. All those powerful men saw you as a strong confident young rich man that could handle a woman like me. A man that’s sophisticated enough to enjoy some kink. Leave them with that impression. Don’t have it pointed out that it wasn’t your idea. That way, next time you sit across from the congressman that I saw in the audience or the head of that big chemical company that was at your table, they’ll start off with the assumption that you’re THAT man. That you’re strong. That you’re confident. That you’re sophisticated. That you know how to handle a woman like me.”
I don’t let Art try and fumble a reply and instead go in for another kiss. This time I let him slide his tongue in my mouth and don’t blanche as his hands come to rest chastely on my hips. When he breaks the kiss, I put on the brightest smile I can with as weak as my jaw is and add, “Because even if you don’t realize it, I know that you’re exactly that man Art.”
My plan works as I can clearly see that Art is not only back on cloud nine, he’s looking at himself like he’s the cock of the walk. The only thing he’s lacking is the confidence to actually do anything with me.
As he steps into the bathroom, I move into secretary mode and finish up the night. As soon as I get the nipple stimulators off, I find the desk phone and see whoever has set up the house has left a series of phone numbers. I dial the costume design number first and have Art’s and my clothes delivered up to the room. Next, I dial the kitchen and have a bottle of champagne, some truffle popcorn, and a tray of oysters brought up. Art may have eaten, but I’m starving. Finally, I call the garage and have them tell Art’s driver to be ready soon for our pickup.
The rest of the night goes smoothly. I still have to have Art help me out of my ballet boots, but he seems to find it sexy to do so and I play it up a bit. He still doesn’t make any move toward me sexually and even takes his clothes into the bathroom again, leaving me the main room to change out of my outfit and back into my office wear.
After we’re dressed, I’ve gotten my hair and face together, and we’ve had our snacks, I have Art lead me out of the house. We don’t pass many people, but I make sure they all see me holding onto Arts arm, all smiles and giggles and adoration toward ‘my man’.
When we pile into the back seat, I let the exhaustion from the day take over, knowing that I’m safe with Art. It turns out that resting my head on his shoulder and having him wrap his arm around me is actually quite a comfortable way to sleep.
When Art nudges me awake I see that we’re parked outside of my apartment. I give Art a final kiss and make him promise to take me out on a real date sometime. I don’t necessarily want to go out with Art, but that’s still part of playing my part. Part of making him feel big and confident is making him believe I want him. So, I make sure he has my current phone number and then head inside.
When I get to our door I take a moment to collect myself and prepare to sneak in and go straight to my bedroom, hoping not to wake Grace up. I don’t even get four steps into the apartment though before Grace turns on the living room light, illuminating her sitting on the couch and looking at me expectantly, “So, adding another man to your stable of boyfriends?”
Grace can’t hold the angry act for long and soon breaks down into a fit of giggles as she has me sit down and tell her about the night. Feeling that it’s good to get it off my chest, I let everything flow. From getting the toys at the office, to Mal finding them, to Art showing up, to Darnell taking me to the copy room, to the blowjob, to the date with Art including the bondage, to the final act of making Art feel like a big strong man.
I really had no intention of letting Grace know about the toys, but at least this way with them still at the office, I can tell her that they’re staying there. But when I’m done with my story and on my second glass of wine, Grace grins and pulls the damned box of toys out of her bedroom. It seems that Mal had the box courier delivered while I was out with Art. I don’t know if I could have mustered up enough mental fortitude to deny Grace her fun with the toys when I was at my best, but I most certainly wasn’t at my best at that moment. I was tired, frayed, and had been sexually teased all damned day and night. So, when Grace said we should go into her bedroom and try the toys out, I reluctantly but willingly took her hand and followed her.
The first thing that Grace did was find some of my lotion and rub it into my skin where the arm binder, ballet boots, and posture collar had bitten into my skin. To her it was nothing more than rubbing some lotion on me, but to me it was way more than that. It was being intimately touched and caressed by someone I used to have regular intimate contact with, whom I still wanted to have intimate contact with, and who I couldn’t play with any longer.
I only tried once to remind Grace that we weren’t supposed to play with each other, hoping that she’d call this whole ‘try the toys’ thing off, but Grace was quick to remind me that there was nothing against me playing with my toys in front of Grace. Or of watching Grace play with her toys in front of me. And that’s what we did for the rest of the night.
Once we were both down to our birthday suits, Grace was quick to notice the nipple stimulators missing. After retrieving them from my purse Grace had me kneel up on her bed and put them on. She even grabbed the remote and put them in ‘motion’ mode where I’d have to keep my breasts moving to keep them from buzzing me.
The next thing Grace focuses on is the butt plugs.
When she pulls the collection from the box, I can see that these are nothing like the bejeweled plug that I’d been wearing at the party. These are covered with slick silicone instead of metal. And where tonight’s ornamentation came with a red jewel, these end with a little silicone covered control panel. Grace marvels over the fact that they’re shaped more cylindrical than the tear drop shape she’s used to seeing and notes that the neck of each, that area between the actual vibrating plug and the end with the controls, is quite long and thin, “Wow, these really are made to stretch you out inside and not necessarily stretch your sphincter.”
I blush but don’t mention that Suzy specifically picked this set because it was said to make its user stretch to accommodate large lovers while keeping that ‘virginal tightness’ that men desire. I can’t help but marvel that my counselor is working at making me both virginal and slutty at the same time.
As the instructions on the plugs say, it goes in easier when you use a lot of lube. Even properly lubed, I still grunt and grimace as I slowly push the toy inside of me. Once it’s seated the end with the controls sits snuggly between my cheeks and isn’t noticeable. At least not visibly noticeable… I notice it a LOT. The controls can be used to induce the vibration portion of the toy, but the remote does it as well.
Grace plays with the vibration settings and compared to the nipple stimulators they’re rather simplistic. The butt plugs can vibrate at a steady rate, from a low rumble to a near hyper pitch, or can vibrate in one of four different patterns. And evidently to save on battery, the vibrations will only stay on for five minutes once they’re activated.
I have to admit, it’s a unique and not unpleasant feeling to have the plug inside of me. I can tell the difference in the shape between this toy and the one at the party, with this one feeling longer and fuller, though not thicker. It seems the only truly unpleasant part will be inserting it and I assume withdrawing it. As for the vibrations, they’d certainly make me notice the toy and they’d probably enhance any sexual activity, but it’s not nearly as stimulating as the nipple stimulators.
Next Grace holds up the three dildos, “So, do you want to show me what it’s like to go down on Darnell? Want to imagine giving your boss a blowjob? Or do you want to really get into it with the strawberry flavored one?”
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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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