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Chapter 49
by
caitlynmasked
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Chapter 47 – Mal and Paris get off
One of Mal’s hands remains on my hip while the other explores my nether regions freely, leaving me to simply try to stay quiet and endure it. I get more of what he’s doing when he finally slaps at my pussy, something that still barely registers but that I can at least physically feel. “So by numb you mean… numb. You can’t feel that at all?”
I try to get my mind around the fact that I’m standing bent over in front of my boss with my panties off, ass and pussy fully on display, while he calmly asks me about my level of sensation. Swallowing again, I answer quietly, “I can feel some pressure, but no, I didn’t feel you slap me there. OH! I feel THAT!!”
Mal’s fingers slide across the prosthetic until he’s gliding them into the crux of my groin where I can clearly feel the intimate touch. Slowly Mal traces out the edges of my sensation. He doesn’t need my verbal cues as my body tensing up is clear enough indication of where I can and can’t feel his fingers touching.
I have to grip the table in front of me a little tighter as all the blood seems to be rushing to my face and head, making my balance a little more precarious. Mal’s chuckle and light slap to my upturned ass makes me realize the motion, that was simply adjusting my balance to me, was me shaking my ass to him. And frustratingly, this all seems to feed into his preconceived notions of me, “God, you ARE sexy Paris. This pussy is almost perfect. If I didn’t know, I’d have a hard time visually identifying it as fake. And your skin, your curves, your moves… you’re the perfect feminine example. I bet you’d even look good without all this…”
Mal’s hand again slaps my ass, this time indicating the faja as he repeats the slap on my hip and waist. I initially close my eyes trying to get through this until Mal’s finger starts circling my ass hole. His voice drops a bit in register as he grips and kneads one ass cheek and taps my pucker, “You know making my girls feel good is always a matter of pride. If I’m asking you to make me feel good, it’s only fair that I repay that kindness.”
My eyes flash wide open as I realize what he’s thinking, “Mal, uh… like, you don’t have to, umm… you don’t, Mmmmfffphhhmmmm”
Mal’s index and middle finger sliding into my open mouth effectively stops my words cold. Worse, I instinctively wrap my lips around his meaty invaders as he starts to slide them in and out. “Shh, just get me a little lube to start. I imagine this isn’t new for you, but I don’t want to hurt you.”
I let out a groan around Mal’s fingers, frantically wondering how to get out of this predicament. I absolutely do not want Mal to stick any part of him into any part of me. Not his fingers in my mouth, and certainly not his fingers in my ass. But worse, I’m afraid that if he does, I’ll repeat the experience I had with Trixie… I’ll cum for him. My body is already reacting to this whole situation, responding with arousal to the sexiness of a curvy buxom woman bent over in front of a suit wearing power broker. My body pays no mind to the fact that I’m playing the part of the buxom bimbo secretary.
When Mal pulls his fingers from between my lips I try to verbally tell him no, but I only stammer and stutter until his fingers start pressing on my sphincter, at which point my voice drops to become one long drawn-out groan. Much like with Trixie, I’m frozen by the new sensation coming from behind me. I’d thought the dildo was big, but Mal’s finger is at least equal in size and he has much more precise control, pressing, circling, pumping, never letting me get any edge of normalcy. When he finally pops in past my resistance, I simply react by pushing forward and away from the invader. Mal’s reaction is equally quick, gripping me by the hip and pulling me back closer to him. He pulls me back enough that I’m barely touching the table, my balance now completely and literally in his hand.
Having Mal’s free hand occupied with holding me upright was good in that he was no longer caressing, gripping, kneading, and mauling my ass cheek. It was also bad as he realizes he’s in control of my position now and uses the advantage to push and pull me in time to his fingers advance and retreat in and out of me. Like a ragdoll, I’m simply out of control and part of Mal’s entertainment.
Even when I try to **** myself up to stand, Mal uses his leverage to shift my balance. All the while his saliva lubed finger slips in and out. In and out. Just as I’m getting used to his finger’s girth and can relax my sphincter around it, Mal pushes more and starts sliding a second finger in. Its own saliva coating and my already opened ass makes this addition go easier, even if its nowhere near comfortable. I’d say it wasn’t pleasurable but once he gets both fingers buried all the way into me, they find that spot.
Unlike Trixie and her little dildo, Mal recognizes what he’s found. It’s not some random point that he pushes in and out toward, hoping to come across again. No, he’s locked onto his target and uses it far more effectively than Trixie did with her toy. Mal’s fingering of me gets almost diabolical as he adds more techniques, tapping, circling, sliding, all spiking my pleasure in different ways that keep me completely unsteady and moaning.
Like a damsel in distress tied up on the train tracks, I can see what’s coming and am powerless to do anything to prevent it. The light and horn of my impending orgasm is impossible to deny but I can’t stand upright let alone get away from the maniac fingering me from behind. Mal even seems to recognize my signs of impending ecstasy as he grips me tighter and speeds up his motions, finally sending me over the edge into bliss.
While my legs tremble and my whole-body quivers, I bite at my lip hard to keep from screaming out loud. Instead, even in this moment of **** euphoria, I have to admit that my muffled whimpering and moaning is erotic to the ****.
When I’m finally coming down from my orgasm, feeling my own cum leaking down my thigh, and feeling like my legs simply won’t hold me up any longer, Mal expertly slides his fingers out of me and pulls me back so that my butt hits the couch cushion right next to him. He doesn’t stop there though, instead pulling my legs to lay over his lap as he wraps his arm around my shoulders and pulls me close to him. While I continue to feel the after quakes of my orgasm flow through my body and try to catch my breath, I can’t believe my eyes as Mal keeps moving, undoing his belt and opening his pants.
Between the mental beat down of being fingered to orgasm by my male boss for the second time and the physical beat down of cumming, I put up no resistance as Mal grips my wrist and pulls my hand to his lap. He knows what he wants, I know what he wants, and I quickly conclude that it’s not worth the effort of putting up any resistance. I can balk and complain, and he’ll physically and mentally push me to do it anyway, so why not do it and just get it over with?
I take care with my long nails to not nick Mal while I pull his underwear down and pull his already hard cock out to stand proudly from his lap. He must have been looking at me when I glanced at the drawer holding the bottle of lube and recognized that I simply didn’t have the ability to even lean forward for that. Instead, Mal ‘graciously’ brings my hand up to my mouth for its alternative lubrication. After an annoyed huff, realizing I was going to lick my hand after it had gripped and pulled his cock from his pants, I close my eyes and drench it with my tongue.
Leaning my face against Mal’s supportive shoulder I vocalize my frustration in the only way left to me, by humming and making quiet annoyed noises. They don’t go unnoticed by Mal, though he obviously mis-interprets them, “Mmm, you sound so sexy when you get into this Paris! Take your time and enjoy it!”
I do NOT take my time. While I hate myself for doing so, I learn exactly what Mal likes in his hand job. Anything to quicken and hasten the process of jacking off my boss’ huge thick cock while he snuggles me close like a lover.
The act of fingering me, or at least hearing me cum on his fingers, must have really turned on Mal as it doesn’t take long at all to get him off. Either that, or I’m just a fast learner and am getting good at giving hand jobs. Either way, I’m quickly hugged tight against Mal as he jerks and cums all over my hand. While he leans back and enjoys his moment of Zen, I’ve recovered enough that I can shrug off the arm around my shoulders, lean forward, and get the towel to clean him up.
After I have Mal safely back in his pants and his pants done back up Mal somehow finds a way to make this worse by gripping my shoulders again and pulling me in for a kiss. I swear Mal must be trying to get turned on all over again as he continues to make out with me for a good five or ten minutes. The last straw, however, is when he finally stops and stands saying, “Paris, I know you don’t want to admit it, but I can clearly see that you’re enjoying this whole process. From the dressing up and makeup to the hair and acting all flirty. You make me push you into it, but you are sexy and great at everything I push you into. I think we’re going to make a great couple!”
As Mal steps around me and starts heading toward his desk I stand up quickly and march behind him, pulling my skirt down as I go. “Wait just a damned minute Mal! You have me over a barrel, I have to do what you say. I’ve let you push me into things I’d never consider including this disGUSTing act of giving you a hand job, but I will not stand here and let you think for any amount of time that I’m enjoying ANY of this!”
When Mal gets to his desk he turns around and leans back against it, smirking at me as if I’m being funny. “Really? You’re not enjoying any of this. This…” Mal gestures up and down indicating my dress, makeup, hair, and body, “…all is because of, what? Because you wanted to con some man you never met? You changed how you look in every way, made yourself into a sexy, flirty, hot woman, in voice, movement, and tenor, to help a friend. You think that pushing down any little bit of masculinity you had before your friend Grace gave you the opportunity to come out of your shell and be the woman you were meant to be, you think that THAT was something anybody could do, or would do? You think that any REAL man would do something like this?”
I stop dead in my tracks when I see that Mal is complexly serious. He believes that I’m taking this as an opportunity to live some girly fantasy life that I’ve always wanted! When he continues, he makes the case as to why he’s acting as he does, “Look, I imagine it’s confusing after living your whole life in a body that didn’t match your insides, but it’s okay to embrace it. It’s okay to say goodbye to being Jamie and embrace being Paris. You can act like you don’t want this, I get it, but I’m not going to let your lies stop you from living a better life. A more feminine life. The life of my secretary and my girl. Now… go get me a fresh cup of coffee and get that letter out in today’s mail.”
As if there was nothing more to be said, Mal pushes off from his desk, circles around, and picks up the phone. In a near rage, I turn around on my heel and head out of Mal’s office. I’m not positive, but I’d bet dollars to donuts that Mal waited until I’d opened the door to call out, “Paris! Don’t forget your panties! And you probably want to clean up your leg.”
FUCK!
There aren’t a lot of people around Mal’s office, but those that are definitely heard my boss call out about me ‘forgetting’ my panties and having to clean my cum from my leg. How can he continue to win so effortlessly!?
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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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