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Chapter 66
by
caitlynmasked
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Chapter 63 – Revelations
It’s not particularly late when the concert lets out. Mal takes us for a quiet drive along the lake before returning us to his apartment. We must have just missed Marie as the table is set for a candlelit dinner. The food is still perfectly hot, and the candles have barely started to melt. When I go to pour the readied wine, Mal points me to my seat and takes care to pour each of us a glass before sitting across from me.
Our dinner conversation is strangely normal. We don’t discuss anything work related or even mention the office. There is no talk of the abnormal beginning to our relationship and it’s more like we’ve been a couple dating for years. We talk of the weather and some previous great times we’ve had in summer. It feels odd that my stories don’t have to change all that much to fit Paris rather than Jamie, but there is no gender component regarding going to music festivals or hanging out at the beach. The only change I had to make was changing sunning myself in my trunks to sunning myself in my bikini.
We talked about the concert, and I learned that Mal wasn’t raised with a love of classical music. I’d always assumed he came from money and was given that type of hoity toity upbringing. It turns out, however, that my rich powerful boss grew up poor on the south side of Chicago. He had to scrimp and save just to get into Chicago State University before he saved up enough money, applied for enough grants, and earned enough scholarships to finish his education at Wharton.
I keep listening attentively as Mal seems to look off into his past and keeps talking. Reminiscing. He met his wife soon after starting at K Edison Global and unlike the young employee that he was at the time, she truly came from money. Her wealthy father didn’t even approve of her dating a ‘commoner’ like Mal. He didn’t care though, as he loved Veronica and she had enough money from her trust fund to live the life she wanted. His finances weren’t important to her.
As he became more successful, earning more sales, earning more bonuses, moving up in the organization and getting stock and cash options, Veronica simply started spending more. Early in his managerial career it was Veronica that insisted he dress up. Wear designer suits and go to a stylist instead of a barber. Mal only started to go along with it when he recognized his attention to style earned him his clients trust as much as his attention to detail.
Just after they were married, Mal became Director of Mergers and Acquisitions and technically a minor partner in K Edison Global. His responsibilities skyrocketed, but so too did his compensation. As he spent more time at the office, Veronica spent more time out. Spending more of their money. At some point Mal’s in-laws lost their fortune. The only way they could retain any kind of life that they had was to come to him. Veronica argued against bailing them out as she was upset that they lost her trust fund and didn’t want them taking ‘her’ money. But Mal paid off their debts, made sure they kept their most important assets, and even bought them into several small businesses that would sustain them.
It was at that point that Veronica more or less wrote Mal off. Even I could see the cruel irony of her falling out of love with him because he saved her family. And because she had more money than he did when they got married, there was no prenuptial agreement. If he was to divorce her, he would lose half of everything. For Veronica’s part, she practically begged him for a divorce. The only reason she didn’t apply for one herself was the fact that she preferred having half control of his full estate rather than full control of half of his estate.
I was absolutely shocked to learn that the first time Mal stepped out on his wife was only five years ago. He’d had a reputation of being a ladies man at the office before that, but it was all rumor and gossip. Only when he found that Nica had been having an affair with her yoga instructor and refused to stop it, did he find solace in the arms of another woman. Ever since then he’s had a string of women on the side almost exclusively for sex, “When I took my vows, I meant them. Even the ’ till **** do us part’ part. I won’t divorce Nica. She’s my wife. So, the women I see on the side are always… well, they’re not the smart, effectual, intelligent, women I prefer. I pick vain, vapid, silly girls who won’t attract that part of me.”
When Mal seems to come out of his reverie and actually focus on me across the table he smiles wryly and raises his glass. His full life story and side women and relationship with me hit me like a ton of bricks as he offers a toast, “To the first girl since my wife that attracts me physically, spiritually, and mentally. To you Paris.”
I’ve been through so many emotional roller coasters with Mal that I’ve lost count. Horror, anger, disgust, sorrow, despair, rage. But never have I felt pity before now. I still can’t completely forgive the man that’s blackmailing me to be the woman he wants, but the fact that I am turning into the EXACT girl he wants, and he’s unable to push me away, does give me pause. It also explains why his interest and attention to me has changed and shifted over the months. From a complete asshole, domineering over my wretched stuck life, to one that as I now see it, is focusing on giving me pleasure. Pleasure I neither asked for nor sought, but pleasure none the less.
Mal gets up and takes his wine glass into the sitting room where he puts on a recording of the same music we’d listened to earlier. Even though I know I could leave all of this for Marie in the morning, my instincts kick in, and I clean up the remnants of our dinner. The more I fall into my routine, the more I clean and serve, the more I feel I owe Mal an apology. I’ve treated him like absolute shit, balking and pushing away any attempts he’s made at making my life better. I’ve opened myself up to Trixie and Grace both, explored various aspects of this feminine life that I’m stuck in, and even found ways to enjoy parts of it. But they take up less than half of my waking hours. The other half is almost exclusively Mal. He isn’t forcing me to stay feminine; he’s just making me fit his definition of a secretary. He IS using me for his pleasure, but he insists on returning that pleasure. It’s not how I want to be pleasured, but have I ever stopped to tell him how I’d like to be pleasured? Have I ever considered that he might take instruction? That he wants to please me for MY pleasure and not his power trip or his own egotistical side?
I’m not sure I can ever love Mal. We’re too different and see the world in too different of ways. But I don’t have to hate him. And if I’m going to be stuck here with him for months yet, I can at least make our lives together… tolerable. Acceptable.
Once the dishes are in the dishwasher, ready for Marie to finish in the morning, I walk into the dimly lit sitting room and see Mal with his now empty wine glass. Taking a deep breath, I steady myself and tell myself that I will at least commit to this tonight. If I find no joy in this, if I end the night in disgust and hate, I can always return to the **** **** partner. But I can at least do this tonight and see if there is an alternative.
Stepping in front of Mal I smile down at him. Once he looks up at me and I know I have his undivided attention, I turn around and reach for the laces on my corset dress. In a soft voice that I’ve rarely used with Mal, but have heard often enough escape my lips when directed at Trixie and Grace, I say, “Could you untie me? We should get to bed.”
Mal may have been deep in the well of his own self-pity, but he quickly stands up and starts untying me from my exotic dress. Once it’s loose enough to come off, I start walking toward the bedroom, moving my hips in an exaggerated enticing motion. At the bedroom door I spin and look into Mal’s eyes. Seeing only wonder, arousal, and surprise there, I smile seductively as I stretch and let the dress fall from my shoulders and pool around my heels. Knowing that all I have on now are my red thong panties, platform heels, and expensive jewelry, I perform a spin and slip into the bedroom.
By the time Mal joins me he’s only gotten his tie and jacket off. I step close to him and work at unbuttoning his shirt while his hands come up to glide up and down my back. I feel my fear return immediately, that he’s going to raise his hands to my shoulders and push me to my knees, but I **** myself to stay relaxed and let him move his hands as he wishes. His movements match the thoughts I’ve realized tonight, those of pleasure giving and seeking and not forcing and humiliating. He seems to be honestly enjoying the touch of my skin and it’s no wonder as he’s never had me here in his apartment like this before. The faja was always in the way. Yes, he’s touched me before, but it was hesitantly. Now, his touch is appreciative, and arousing.
Once I have his shirt unbuttoned, I pull it free of his pants and press my palms to Mal’s belly. Sliding my hands up over his chest and to his shoulders, I glide his shirt off and over his arms where it falls to the floor. I swallow hard as this is the real test. Kissing Trixie is glorious and lovely and pleasurable. Kissing Grace is subservient and honoring and giving. But kissing both is kissing that sweet feminine flesh. Their soft curves, their lovely breasts, their sensitive nipples, their smooth skin. Kissing Mal isn’t that. His skin is warm but it’s hairy. Masculine. It’s not calloused or rough, but it’s nowhere near smooth or soft either. But this is the path I’ve decided on and I’m going to commit to it. Leaning forward as my hands drop to his belt, I start kissing my around Mal’s chest.
As Mal’s chest hair tickles my nose, his hands find their way to my sides and tickle me there too. It doesn’t take me long to get his belt undone and his pants loose enough to drop them along with his underwear to the floor. As I expected I’m immediately slapped with his cock springing free, tattling on the effectiveness of my body and my seductiveness. Instead of acknowledging his hardness though, I want to go that extra step. I want this to be special, to acknowledge that I’m doing more than going through the motions we’ve established so long ago. Taking Mal’s hand, I lead him over to the bed. Turning him so that his back is to the bed I step close enough to press his cock against my belly as I move up to my toes, wrap my arms around his neck, and kiss him as passionately and as willingly as I’ve ever kissed the two women in my life.
Mal returns my affection with as much, if not more intensity, his hands wandering over my back and finding their way to the new globes of my ass. I let out a little squeal as he grips and kneads me down there, teaching me what it is to be ‘manhandled’ as opposed to being caressed. And it’s a powerful feeling that I don’t know that I could receive from either Trixie or Grace. The domineering physicality is something they can both perform and have performed to my delight, but while I have to submit to them, Mal’s mere size, his physical presence, his natural power, demands and enforces his superiority over me. He can overpower me in ways that neither Grace nor Trixie could imagine and is showing a level of restraint by NOT pushing me further.
After several long lovely moments reveling in Mal’s power, choosing to enjoy it instead of fearing or hating it, I step back and press him hard in the chest, pushing him onto the bed. Crawling in a manner that will show my large breasts hanging from my chest I move around Mal and pat the top of the bed where I’d like him. Unlike Mal, who could move me into any position or place he wants, I have another reminder of our physical differences and natural power… I have to request him to move.
Thankfully Mal grins and understands what I’m doing as he lifts his leg over me and settles to sit back against the headrest, his strong well-muscled thighs resting outstretched on either side of me. I take another moment to ready myself, knowing exactly the kind of show I’ll be putting on for Mal. Knowing that whether I find a level of joy in this that I want to repeat or not, he’s likely to enjoy it and demand recurrent performances. Once I’ve committed myself internally, I stretch out as I’ve seen women in exotic films do. I’d never given any thought as to the gymnastics that this requires, but I have to arch my back to an **** I almost didn’t’ know possible in order to raise my ass up high and push my breasts down into the comforter. This puts me right at eye level with Mal’s fully hard cock, bobbing and throbbing right in front of my face. Reaching forward, feeling only a small twinge with the memory of Darnell’s cock being this close to me, I take hold of Mal’s hardness with both hands and start to work on him.
Before, I’ve always worked at getting Mal off as fast as possible. I wanted this humiliating act over with as little fuss as needed, figuring his orgasm was pleasure enough. This time, I follow through with the commitment my previous show has promised. I take my time. I use the techniques I’ve learned over these months on what Mal likes and what he doesn’t. Instead of barreling toward that end goal, however, I take him into pleasure only to let him plateau there while I play. I extend my area of touching and caressing and rubbing to his thighs, to his balls, to all areas of his shaft and cock head. When I sense he’s getting too close, I focus on other areas that he enjoys but lets him cool down. And minutes into this loving teasing, when he starts to reach his hand forward and take a directing role, I do the thing I’ve never done to him before… I slap his hand away.
If memory serves me right, the longest I ever took to get Mal off was ten minutes. And that was due to inexperience and nervousness and fear. Once I got past the shock, once I had the techniques down, I’d get Mal off within a few minutes if he didn’t interfere and purposefully slow me down. This time, without me letting him speed me up, I tease and please him for a full twenty minutes. Only when he’s squirming around and breathing hard and looks like he’s about to ignore my shooing hands and finish himself off, do I go in for the kill and let him shoot over the edge.
And this is the part that takes the most commitment from me. In this exotic erotic position, face down and ass up, eye level with Mal’s manhood, I have very few options on where to direct his cum. I could go straight up but it would rain down on both of us and get on the very comforter we’ll be sleeping under. I could direct it toward his belly but the position I placed him in means it might shoot at his face, and with as much as I’ve teased him it may well get there. That leaves directing it at me.
I’d considered the ultimate sacrifice. A show that would demonstrate my commitment to his pleasure over mine. My face. But as much as I want to make this special, I know I’m not ready for that. I couldn’t finish this act by being horror struck and still have him enjoy it. Not wanting him to shoot in my hair leaves me few options then. So, as I feel him star to throb and grow in my hand, I quickly bush my hair off to one side, and scoot closer. I smile up at Mal even though I now have his cock literally next to my face as he clenches up and starts shooting jets of cum over my shoulder and onto my back.
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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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