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Chapter 42
by
caitlynmasked
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Chapter 40 – Sleeping with Mal
I stand still, watching Mal intently, waiting for the other shoe to drop. He can’t seriously expect me to dress up in this outfit for him. Can he? But as he just stares back at me expectantly, I wonder just how mentally deep into this fantasy Mal is. He was deep enough this morning to have me jack him off. And he made it clear that me wrapping my hand around his cock wouldn’t be a one-time event. Setting the butt plug down I turn around so that I’m facing Mal fully.
I could hem and haw and flutter around what I want to say. I could talk about how these under clothes aren’t meant to be slept in. I could mention that it’s almost three in the morning and that I’m tired. I could remind him that I’m not a real woman. But I decide that Mal appreciates directness, so I start with the one fact that has to be very clearly understood, “Mal, we’re not having sex. I am not interested in men. I don’t think you are either?”
Mal holds his serious look for a moment before breaking into loud honest gales of laughter. After a bit, once he’s stopped laughing and only occasionally chuckling, he wipes the laughing tears from his eyes and says, “Paris, you crack me up. Of course we’re not having sex. It’s three o’clock in the morning and we’re going to be in the office in a few hours! You’ve completely misconstrued what that outfit is for. As for what you or I are interested in, we’ll hold the jury out on that as I still don’t believe you’re just some normal straight guy that happens to dress up as one of the sexiest women I’ve seen. You’re right, I’m not interested in men. But when I look at you, the very last thing I see is a man.”
I feel like I should be happy as Mal started out by laughing at the idea of us having sex. But while I’m pleased to know that we’re not having sex tonight, I feel like the main reason is because it’s so late as he’s made it clear he’s still assuming I may want to have sex with him and he sees me only as a woman. I decide to take the small victory of no sex tonight though as I gesture toward the lingerie and ask, “Okay, so what is this about then?”
As Mal starts unbuttoning his shirt and approaching me, he nods at the box of frillies, “That is one side of our life from now on Paris. Perception. Like our date tonight, it’s all about perception. People seeing us out together and making up their own minds about what’s going on. And so long as they see what they expect to see, then they’ll think what I expect them to think. That we’re fucking. And so long as that remains true, that other people believe I haven’t changed and am having a comfortable normal sexual relationship with my sexy secretary, then we can work on the other side of our life. Reality. Whether we have sex or not is up to you. I’m interested in exploring that but I’m not going to **** you.”
Mal rolls his eyes as he shrugs out of his shirt, “Well, besides the hand jobs. That’s simply helping solve a problem that you are partially responsible for. It’s hardly sex, is it? Anyway, the lingerie is so that my housekeeper sees what she would expect to see when I have my dates over. Sexy lingerie and a sex toy or two. The plug can stay on the nightstand along side some lube. She’ll make her assumptions, and perception will be made into her reality.”
I nod, feeling a little embarrassed at thinking that Mal bought the lingerie expecting to have sex with me in it. He’s clearly smart enough to know what I’d look like under these clothes and while he may be interested in some form of sex, I highly doubt he’d remain interested once he saw me in the faja. I shrug and start toward the door, “Okay, I’m sorry for doubting you. Goodnight Mal.”
Just as my hand lands on the door handle I hear Mal clear his throat loudly behind me. As I turn around, I see him holding the box out toward me with his eyebrows raised expectantly, “Forgetting something? If you don’t want to get changed in the master bath, that’s fine but be sure to bring your clothes back to lay over a chair or fling over the floor. That way Marie can see it in the morning.”
Mal keeps walking toward me, making me either reach out to take the box or have him push it into my chest. Once it’s in my hands he turns and starts toward the bathroom as he slips out of his shoes and starts undoing his pants, “By the way, do you have a preferred side of the bed? I normally sleep on the right but it’s not that important to me.”
I feel like I’ve slipped from one universe into another. In one it’s been made clear that we’re not having sex, but now it seems he wants me to get dressed up in the lingerie and is talking about us sleeping together. In the bathroom I hear Mal brushing his teeth, so I walk over and see him wearing only his tight trunks, “Uh, Mal? I’m confused again. I was going to go to one of the other rooms and go to sleep. Why should I bring my clothes here? And why would it matter what side of the bed I sleep on?”
Mal spits out the toothpaste and rinses before starting to wash his face and beard, “Paris, it’s late and I really don’t want to have to explain everything again. My housekeeper gets here early in the morning. Sometimes, even before I get out of bed. If she comes in and finds you either in one of my spare rooms or still asleep someplace other than by my side, any perception we’ve tried to establish is gone. No, you’ll wear the lingerie and sleep beside me. I’m hoping that you’ll be awake before she gets here so that she can just find the worn lingerie on the floor next to your clothes. But if she walks in and sees you in your body shapers wearing the lingerie, she’ll at least still go with the assumption that I’m fucking you.”
Mal splashes some cold water over his face, rinsing the last of the soap off. As he towels his face dry, he looks at me, losing most of his good humor and showing his more intense side again, “Now whether you do it here in the bathroom, in the bedroom, or in some other room, get your clothes off, get into the lingerie, get ready for bed, and get under the covers. And if you need to sleep on the right side, let me know. Otherwise, that’s where you’ll find me.”
With that said, Mal tosses his towel on the floor, walks past me, and climbs into bed. I silently count to ten just to make sure I don’t scream in frustration before walking into the bathroom and closing the door. My nighttime routine is far longer than Mal’s so by the time I’m undressed, have cleaned my makeup off, have my hair brushed, have my face washed moisturized and lotioned, and finally work my way into the over the top lingerie, I step back into the bedroom to find Mal already sound asleep. Just as he said, he’s lying on his right side on the right side of the bed. His arm is under his pillow and stretched out over the edge of the bed, giving me hope that he’ll stay on that far side of the bed all night. Quietly I move around to the other side of the bed and slip under the covers. I hate to admit it, but Mal’s sheets, pillow, blanket, and duvet cover are all really nice and comfortable.
When I turn the light out and lay back it doesn’t take me long to start drifting off to sleep. Unfortunately, Mal’s quiet, still half-asleep, words snap me right back awake, “g’night hun”
I don’t bother responding, doubting that he’s awake enough to remember if I said anything or not. Plus, I don’t want to acknowledge that I’m ‘hun’ to him. But his spoken word just reminds me mentally that I’m wearing lingerie while lying in bed next to a man. A man that I’ve jacked off just hours before.
Not that two hours of sleep was going to feel all that refreshing anyway, but I didn’t sleep well in Mal’s bed. Every little thing woke me up and between recognizing that I was still had the faja on, feeling the lingerie on, or feeling the silk sheets under me, I’d come fully awake and realize just where I was before I could accept it and drift back asleep.
Marie may get here before Mal wakes up, but as I’m used to getting up so much earlier than him, I’m out of bed, showered, and fully dressed before she even arrives. Marie seems very nice and doesn’t make a fuss about a strange woman being over. We chat a bit before I finish putting on my makeup and doing my hair while she puts on the coffee. Only once I’m fully ready, with my date night clothes and lingerie laid out on the floor for Marie’s later discovery, do I realize that Mal never discussed heading into the office. I could always go to the nearest L station or grab an Uber and to the office, but I don’t want to just assume Mal didn’t want to go in together. So instead of leaving, I wait with Marie as she gets me a light breakfast of fruit and a muffin and we chat.
I actually start feeling anxious waiting for Mal as it feels like I’m going to be to work ‘late’ even if it is walking in with my boss. Thankfully when Mal comes out, he’s already showered and dressed and looks like he’s ready to start the day. Without missing a beat Marie pours him a cup of black coffee and makes him a cup of oatmeal while he approaches me. I only marginally stiffen up when I realize what’s coming but think I make it look natural when Mal cups my cheek and bends down to give me a soft kiss, murmuring, “Good morning sweety. Sleep well?”
It makes me feel like I’m in a play without knowing what my lines are. But as Mal takes his coffee from Marie and pulls out his phone, checking his messages, I smile and respond, “Of course. Your bed is wonderful!”
The play continues with Mal going through his normal morning routine. When he’s ready he leans in and gives Marie a kiss on the cheek, “I’ll be heading home tonight from the office and staying there. I’ll be there all weekend and likely even go back Monday night. Once you’re done today, go ahead and take the rest of the weekend off. I’ll see you Tuesday night or Wednesday morning.”
Without waiting for a response from his housekeeper, Mal takes my hand and guides me out of his home away from home and we head into the office without any more said.
I can already see that Mal likes the attention we get as we walk in together. It’s not much and it’s not overt, but plenty of people nod and smile at us as it’s clear we were ‘together’ for the night. The ‘perception’ of those at the office will be clearer and clearer… we’re fucking at his apartment at least once a week. Beyond that revelation, the day proceeds normally. I see the irony of course when we leave for the night and I meet Trixie in the lobby. Date night with Mal is all a farce to make people believe we’re an item while me meeting Trixie is supposed to look like two gal pals getting an after-work drink while we actually go out and have some fun.
Trixie and I grab a bite to eat where I get to hear all about her trip with her boyfriend to Cleveland. They toured the Rock and Roll Hall of Fame and went to the museum of art but mostly spent the long weekend fucking. I’ll freely admit that listening to Trixie talk about having sex in various positions and places completely turns me on, especially with as descriptive as Trixie is in talking about getting railed from behind in doggy style. I can picture being behind her, gripping her thin waist and plowing into her lovely bouncy round ass.
Evidently her boyfriend loves getting head, which is growing tiresome for Trixie. We spend most of desert talking about it, which is frustrating. I’d love to listen to Trixie talk abut giving head but since she doesn’t like doing it, wants to please her boyfriend, and ‘knows’ I like giving head, or rather has ‘the perception’ that I like giving head, our discussion is mostly me talking out of my ass about performing oral sex on men. For the most part, I just picture the women that have gone down on me and try to imagine what they were specifically doing and what they must have been thinking and then put that out in the first person. Under normal circumstances I’d hate hearing myself say things like “If you swallow when it hits the back of your throat, it’ll help you get past your gag reflex” and “You have to mix it up, just suck on the head for a while letting your tongue get all the good spots then let it pop out and lick up and down his entire length. He’ll love it!” but under these circumstances I know that talks like this will lead to Trixie and me in her bedroom and eventually her hands and lips and tongue on my own penis.
It's sad that I can barely call my own equipment a ‘cock’ any longer, but when I’m still wearing my stockings and having someone play with ‘my’ breasts while they tickle and kiss my junk, its not really a cock at that point. I’m just happy that a sexy woman is doing it and I don’t’ have to take care of that myself. Especially since Grace seems to enjoy playing the denial game at home. I get the ‘pleasure’ of getting her off many times, but she not only doesn’t return the favor, she teases me about not getting off and even enforces Trixie’s rule of not self-pleasuring myself.
In other words, the only times I get to cum now is with Trixie, and it’s leaving me horny all the time.
My time with Grace does have its reward besides making her happy though as Trixie recognizes my newfound skills and enjoys them thoroughly. And after a long weekend of getting Grace off, after having to not only jack off my boss but spend the night in bed with him while wearing sexy lingerie, and finally getting my ‘gal pal’ to scream out my name several times, I get to lie back and have her lick, caress, and kiss me to my own screaming orgasm.
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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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