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Chapter 88
by
caitlynmasked
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Chapter 84 – Toy and friend control
I did my best to keep my mind occupied, to block the memory of having Mal paint my face up close and personal while being pushed over the edge in my first set of multiple orgasms. But the day seemed destined to be about that feature, that event. First was of course dealing with Mal’s mixture of humor, desire, and pride. There wasn’t any maliciousness in his attitude which somehow was like pouring salt into a humiliating wound. It was as though he enjoyed the whole endeavor and just assumed that I’d enjoyed myself too. And I couldn’t even deny it as I had clearly cum. Clearly orgasmed while jerking my boss off and then continued to cum while he shot his load directly into my moaning mouth.
After I finally convinced Mal, I needed to clean myself up and redo my makeup, he let me do just that. Unfortunately, it was in his own small private bath where he was able to watch me do my work. That, of course, didn’t leave me any opportunity to remove the offending toys.
When I finished up and returned to my desk, I made sure to swipe the remote to my nipple stimulators off of Mal’s desk, much to his chuckling amusement. When it became clear that no one was pointing or staring at me, that Mal’s and my intimate moment was in fact a private one, I tried to lose myself in typing up Mal’s letters. Halfway through, however, I felt the toys all go off again. Just a quick on at full blast and off again that was more of a shock than a return to the undeniable arousal, but it still got my heart beating quickly. Was that Grace? Did she somehow figure out how to control all the toys together? Was it Frank? Was he lurking about trying to find out the target of his internet surprise? I had no way to find out which just left me with continuing to work and trying not to react when they’d repeat those shocking buzzes every few minutes. Just random enough that I was always unprepared for them.
When I finished up the letters, I printed them all up and walked them into Mal’s office where he was just finishing up with a phone call. As I laid them out on his desk for his final approval before getting them out into the delivery system, Mal hung up the phone and asked me to wait for a moment. I stood at my ‘resting’ position, which looked anything but restful. Legs fully stretched to show off my calves and ass. Hips rolled forward to further push out my caboose. Chest pushed out to emphasize my breasts. Eyes looking forward with a slight smile on my face, my mouth hanging just slightly open. And finally, my arms pushed back a touch to add even more visual attention to my breasts. The pose used to be completely foreign and uncomfortable, but the more I’ve held this position, the more comfortable and ‘every day’ it’s become. I could now probably stand like this for hours without fatigue showing up. When I stand like this in front of Mal’s desk, I tend to just look over his head so that I can see the beautiful cityscape behind him. It really is a beautiful view.
Not watching Mal closely is why the toys turning on was another complete shock. I know I jerked a bit but believed I held my pose well enough that unless Mal was staring right at me, he wouldn’t have known. When I glanced casually at Mal though, he was grinning as he looked up at me with his phone in one hand. Once he knew I was watching he emphasized his thumb pressing something on his phone’s screen, which immediately corresponded with all three of the toys turning on at full blast again… but not turning off.
It’s not until I start to obviously squirm under the intense buzzing at all my erogenous zones that Mal taps his phone again, turning the toys off. He must have read the confusion on my face as he turned the phone round so I could see the screen looking exactly like the one Grace showed me earlier. His voice was a mixture of smugness and jesting, “When Frank sent me a message, telling me that there was someone wearing an internet-controlled toy, I didn’t think much of it. There are plenty of people in the office that might bring such toys to work. It wasn’t until he replied later that he found the person had multiple toys that could be linked that I began to put the pieces together. His discovery of the multiple toys lined up perfectly with Art’s visit. With your little bit of extra fun under my desk.”
Mal leans forward on his desk as my shoulders slump, already realizing what’s coming, “It occurred to me that it might take more than jacking me off right into your smiling little mouth to make you cream your panties. So, I joined in with Frank’s fun by logging into the same toy. While you’ve been typing away, I’ve been tapping it every few minutes. I’ll admit, you must really love it as I couldn’t tell for sure if you were being buzzed or not. At least until right here and right now.”
To emphasize Mal’s point, he turns the toys on again, but this time syncs them to a three-way dance of buzzing and vibrating between my nipples, ass, and pussy. As much as I want to cry out in frustration, the only sound betrays me by coming out as a drawn-out wanton moan while I try to not crush my thighs together. Mal thankfully turns the toys off as he continues, “I won’t ask why you’d come in here with your toys on an open network Paris. Only because it’s so obvious. You want to have fun with your toys. Like much of your act, you say one thing, but your actions say something completely different. And as actions don’t lie, I’ll believe those. You talk like a little prude but act like a spicy girl. But for your personal benefit and my own satisfaction, I’ve logged in as the administrator of your toys and locked out all others. And yes, I saw that even your roomie had been playing with you. If you’d wanted her to keep access, you probably should have had her password protected.”
My heart only sinks further as Mal finishes up, “I want to make sure you have those toys in place whenever possible. I realize some of the bras you like won’t allow the nipple stimulators and some of your skirts won’t allow those panties, but I can’t think of any reason you should ever show up without your little butt buddy in place. And don’t worry…” Mal’s genuine smile and wink show me that he honestly believes he’s thinking of this as fun and harmless “…I’ll be sure to keep you as entertained as you deserve to be! Now off to work, I think you need to do some travel booking if I’m not mistaken.”
While Mal doesn’t activate the toys again, I’m left nervous for the rest of the day that he’s going to turn them on at the worst, or most entertaining, times. Like when I have guests at my desk. He was right though in that I needed to focus on the travel arrangements.
In addition to Frank and Thomas’ trip to San Francisco and finding them a secretary, Grace’s trip to Miami and her need for someone from my department, and Darnell’s cheap yet luxury trip to the Maldives, I’ve somehow picked up a trip for five of our senior security staff to attend a corporate internet security conference in Dallas, a trip for Mr. Stirling and Trixie to Omaha of all places for a human resources symposium and even setting up a vacation for Mr. Zeller and his family.
The first trip to confirm is Mr. Zeller’s vacation. While it’s not business related, keeping Mr. Zeller happy is keeping Mal happy and keeping Mal happy is keeping me happy. As the highest-ranking corporate officer traveling at that time, I make sure to book the company’s private jet for his family’s use. Once I have their fortnight in Switzerland setup, I move to confirm everything I setup for Frank and Thomas’ trip to San Francisco. I add Claire Lindblom to accompany them as their administrative assistant. It’s a little below her station but as it’s my decision and she’s kind of responsible for me and Darnell getting together the other day, it fits my current mood. Once that’s set and I’m done giggling at Clair’s return email, I set up Stirling and Trixie’s Omaha trip. It might be the easiest booking as there just aren’t many good flights to Nebraska, nor are there many nice hotels there to pick from. Next, the security conference is actually quite easy as there are direct flights between Chicago and Dallas and the conference is in the Grand Hyatt connected right to DFW. Their room are already set aside by the conference so it’s just a matter of reserving them.
Next, I start working on Grace’s trip to Miami. I spend quite a while making sure there isn’t any good reason I can’t accompany her. The only thing that might stand in the way is Mal himself. He still occasionally complains about my replacement while I was recovering from my surgical procedures. The only time he operates well without me is when he’s off on his own trip and even then, its only because I prepare him so thoroughly that I’m practically there anyway. He’d have to be on a trip of his own for me to run away with Grace.
When the idea hits me, I simply freeze and go over it in my head. This might work for everybody. Mal has talked about taking an exotic trip without Nika there to ruin his fun. He only travels for business though. And even then, he tends to only go when he’s absolutely needed. If I set up a trip, make it as exotic and first class and fun, all without breaking the bank, and make it where his presence is the difference between success and failure…
I quickly start booking Darnell’s trip to the Maldives. My initial run at his trip had me cutting every cost I could. I’m not sure what flying from Chicago to Dubai, to Malé would be like all in economy, but I’m pretty sure Darnell would have ended up feeling like a pretzel after the nearly thirty-hour trip. But pooling the company’s flight points together means that I can bump the two tickets up to first class. Before, I had him simply staying in the hotel near the resort where the CFO of Atlas Capital was staying. A couple trades through the travel agency we use, and I book Darnell and ‘guest’ in the resort itself for the full two-week trip. Through various trades, discounts, and other sneaky ways to save money, I’m able to add on all the treats that would make a trip like this spectacular. Making it an easy sell for Mal to be the Mergers and Acquisitions member to join Darnell.
And while Darnell will be busy most days with what he needs to do, Mal will only have that second week to wine and dine the CFO and get the information he needs about McGregor corp. That means a relaxing fun week including plenty of beach time!
I even find out that I can sweeten the deal since it only adds airfare… I add Trixie along with Darnell and Mal’s trip. My bff gets a trip with her boyfriend to the exotic Maldives, my boss gets out of my hair and still has a very competent executive assistant, and I get to spend a week on the beach with my good friend and no other stressors.
Win, win, win!
Speaking of the devil in the short dress, I spot Trixie mincing her way up to my desk. I can’t hide my smile as I know that marks the end of the day and I can finally move on to important private matters. Like convincing my bff that I don’t want to continue giving her boyfriend blowjobs.
After making sure there aren’t any last-minute tasks Mal needs done, Trixie and I head to the elevator and on out to the windy city. When Trixie suggests we go shopping I almost hate to admit it, but it sounds like fun. Being one of the guys feels like a long-ago memory but at least I can enjoy being one of the girls. With our arms hooked together we stride down in the late afternoon August heat to our favorite little boutique that’s near the office.
As always seems to be the case, while Trixie is still trying to find her own dress, I pick out something quickly. I only have to try on four or five dresses to find this extra sexy number that I’d normally call an LBD, or Little Black Dress, if it wasn’t covered top to bottom with little shiny sequence that all catch the light at different times. It absolutely hugs my hips and upper thighs, while its spaghetti straps seem to barely hold up its diving front that shows off a big share of cleavage. Just by pulling my hair down and adding some of the boutique’s fancy costume jewelry including a necklace, a bracelet, and an adorable ankle bracelet, I have an almost perfect club look.
About an hour later Trixie and I walk out with completely new looks. I’d added a pair of knock off Prada slink back pumps in red that add just the right pop of color while Trixie ended up in an exotic lace and latex dress with a large peekaboo front showing off her own sizable chest as well as most of her belly.
Before Trixie starts calling up an Uber to take us to some fun club, I pull her into a nearby trendy bar where we’ll be able to talk. Just knowing that Trixie is eager to show both of us off means that I should be able to get through the conversation fairly quickly.
When I sit and pull my feet up under my seat demurely, I’m reminded of my toy still plugged into my rear as this position puts most of my weight on it. I try not to let that steal my focus away though as I think I’ve finally got the words ready that will let Trixie know how I feel, what I want, and not let her down or disparage Darnell in any way. It’s certainly full of lies, but its just adding to the lies I’ve already established about myself.
After our first drink is finished and our second is on the way, I lean in toward Trixie and start talking, “Trixie, I want to first thank you. You’ve really helped me come out of my shell and find the real me. You know how much I love going out with you and now with both you and Darnell. If it weren’t for you, I think I’d still be that little mousy secretary that jumped anytime anybody said boo!”
I can see that my compliment is already paying off as Trixie smiles like she does only when she’s really happy. I keep going, “Between Mal and me, you and me, and now Darnell and me, I’ve had a lot of fun finding and exploring this side of me. I mean, yeah, you know I’ve had enough oral sex that I know I like it, but having it with, with…” I gesture down at my curvy body “…with this is something else entirely. Between Mal’s forcefulness, Art’s shyness, and Darnell’s pure animal attraction, I think I’ve discovered what I’d really want in a man. A man… you know… like a man of my own.”
Trixie moves around the booth until she can pull me into a hug, nearly squealing with excitement, “Oh Paris that’s so exciting! I know Darnell will miss his chance to get some more office blow jobs, but he’ll still be so happy for you! Now we have to go find this mystery man for you. Someone strong like Mal, sexy like Darnell, and kind like Art. I know just the place… come on!”
And before I can even suggest that we can take this slow and just have a fun girl’s night out, Trixie starts dragging me out of the bar and back into the street.
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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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