“Yes, Boss,” I say.
I turn my head to see him taking off his shirt and revealing all of his muscles for me. He takes off his pants and slips on a condom and then I feel his cock up against the opening of my pussy.
“Are you ready?” he asks me, as he holds onto my hips.
My ass is sticking up in the air on his desk and my pussy is completely exposed to him.
“Yes, Boss.”
I’ve never been more ready for anything in my life. I never imagined that this is how I would lose my virginity but I love everything about it.
He pushes himself into me and at first I feel a pain so sharp I cry out. But soon my cry turns into one of pleasure as he completely fills me with his large cock.
“Yes,” I moan, holding onto the desk as he pumps his cock in and out of me a bit harder now. “Yes, yes, yes.”
“Oh Madilyn, you feel so good,” he moans, spreading my ass cheeks open and shoving his cock in and out of my pussy.
It feels like his cock has belonged in my pussy forever. Like I was empty without him and now that he fills me up I’m whole. He reaches down and plays with my clit while fucking me.
“Take my whole cock in your pussy, my little pet,” he says, thrusting in and out of me.
“I’m going to come,” I tell him, panting. “I’m coming on your cock.”
“Come all over my cock,” he says, pulling and twisting my clit while juices from my pussy run all over his dick.
“You’re gushing for me, baby,” he says, and I feel so good that I recoil from the touch of his hand on my pussy.
“Sorry,” he says, backing up just a little bit.
I reach behind me and take his hand in mine and squeeze it.
“Don’t stop,” I tell him. “It just felt extra…”
“Sensitive?” he asks, with a slight chuckle. “Yeah, that happens sometimes. We just need a little break. Then we can keep going.”
I sigh with relief— I had never come so much or had that much of a sensitive reaction after coming and was beginning to think there was something wrong with me— and say, “Well, I’m ready to go again when you are, Boss.”
And I have a feeling I always will be. I can’t believe my boss just took my virginity. And I can’t believe how much I liked it.
Maybe this will actually work out.
As long as he can let down his tough exterior now and then and let me have things go my way sometimes too. And as long as it doesn’t interfere with my career. Which seems like a really insane wish to hope for.
Chapter 29 – Asher
I take a breath and feel glad that Madilyn is so winded she can’t tell how into this I really am. I love touching her, kissing her, eating her sweet pussy and fucking her. I have no idea what I did before I knew her. This experience is incredibly different than any I’ve ever had before. And I’ve had a lot of fucking experience with women.
I love how she says she’s ready for me. I can tell by the tone of my voice that she’ll let me take her any time I want her. And that’s exactly what I want to do.
I slap her supple ass and push my cock back into her pussy. She squeezes my cock with her insides as if she wants me to stay there forever.
I push my cock in and out of her, feeling it get harder and pulse more with every pump. I thrust and out and she dangles her legs out. I wrap them around me while pushing myself into her more. She moves her body back and forth, riding my cock like a horse.
I feel so powerful as I fuck her but so weak with desire and lust. I finally feel myself pulsating with cum and I tell her, “I’m going to come,” but she’s saying the same thing.
“Again,” she says. “I’m going to come again.”
“Do you like when your boss fucks you?” I ask her, feeling the heat of her pussy at the same time that I feel the amazing release of everything inside me flowing out. I wish there weren’t a barrier between us to block the sensation.
“Yes, Boss,” she says, as she comes on my cock while I finish coming as well.
I pick her up and carry her, naked and nearly as sweaty as I am, to my office chair. I sit her in my lap and she puts her head on my chest.
“I love your muscles,” she says, tracing my pecs. “And your tattoo.”
She winds her finger down my chest, moving it over the ink I had gotten done some time ago after a trip to Katmandu.
“It’s an Indian symbol for rebirth,” I tell her.
It has multiple meanings but I don’t tell her those. Not yet. I have a feeling she will be able to draw everything out of me though.
“Cool,” she says, and then she looks into my eyes and smiles. “That was amazing.”
“So how does someone make it through law school and this far in life and still never have sex?” I ask her.
“Oh my God,” she rolls her eyes. “Everyone always asks me that. Not you too!”
“Well, they can’t ask you that anymore.”
I wink at her and she laughs again.
“Very true.”
She sighs.
“I was just with the wrong guy for a very long time.”
Now she shrugs.
“I guess it’s just as simple as that.”
“But you’re not with him anymore?” I ask her.
I always feel protective and possessive over my pets but this is something different. I just literally possessed her in a way no one ever had before. And I want to make sure I’m the only one who does.
She shakes her head.
“It was a long time coming but it finally happened,” she says. “I’m done with him. For good.”
“Hmmm, it can’t possibly have anything to do with me, can it?” I ask her.
“Yes, Boss,” she mimics and we both laugh this time.
She stands up and says, “Well, I have to work on that big brief that’s due tomorrow.”
My eyes linger on her beautiful, naked body.
“I don’t want you to go,” I tell her. “But I do want you to kick ass on that brief.”
She laughs. “What a dilemma you’re facing.”
“Soon we should go somewhere besides my office,” I tell her. “Maybe somewhere nice.”
She looks at me a big surprised and I feel rather stupid. I never take my pets out. I never do anything with them that doesn’t revolve around the office. And now she knows she’s different.
She smiles and I’m glad I suggested it. I can tell it makes her happy.
“Well good luck,” I tell her. “Let me know if you have questions.”
“Yes, Boss,” she says. “I sure will.”
She leaves and I lean back in my chair, wishing I had a cigar. I only smoke them on special occasions but I would say that this qualifies as one.
I try to work on some notes for the case but I can’t concentrate. After about an hour I decide I should go home and shower and call it a night.
But I can’t help but want to see her one more time. I feel lick a fucking middle schooler with his first crush.
I open Facebook on my browser and type in her name. I’m no longer stalking her to be my pet, I just want to see her smiling face.
Instead I see a new post on her wall from Jimmy, whom she had just told me was her definite ex-boyfriend. It’s a picture of her holding flowers and smiling. And it says “Had a lovely time watching TV with you in our living room like in the good old days. Here’s to a fresh start.”
What the fuck?
I stand up and slam my fist down onto my desk.
I knew it was too good to be true. I knew I shouldn’t have trusted her.
I should have stuck to my rules and now I let her play with my heart. But I’m not going to do that again. That’s for damn sure.
Chapter 30 – Madilyn
ONE WEEK LATER
Sleeping with my older, experienced, filthy rich boss wasn’t part of my job description. But there are a lot of fringe benefits I wasn’t told about in advance.
Asher Marks is so full of surprises.
I don’t know what I was expecting to happen between us, but I wasn’t expecting it to happen so soon. And I wasn’t expecting to enjoy it so much.
And I certainly wasn’t expecting him to just disappear afterwards, even though he clearly enjoyed it too.
It’s been a week since what I thought had been our reconciliation, but I haven’t heard anything from Asher. He’d given me the entire file on a big case that’s being litigated— Schwartz Capital— and told me to study it from top to bottom.
So I’ve been sitting here in my cubicle, learning everything about the case, including studying up for a hearing on a big dispositive motion that’s coming up soon. If our client loses this hearing, its case is over for good.
I certainly hope that Asher prepared for the hearing before he took off to God- knows- where and left the file with me. But just in case, I prepare arguments and an outline with plenty of notes. I anticipate every argument that the opposing side will make, from their briefs, from case law and from racking my brain to think of any possible point I would make if I were in their shoes.
Meanwhile, the Barbies and other associates have walked by snickering and whispering.
“Guess she’s been dumped,” they’ve said, loud enough for me to hear.
“That’s what happens when Asher Marks doesn’t end up liking the mentee he’d chosen,” they’ve said. “He books a seat on his private jet and gets the hell out of Dodge for a while.”
“He’s probably in some Caribbean island blowing off some steam about his bad decision, with some local ladies.”
“He’ll come back tanned and refreshed, with his senses returned to him and a new mentee chosen, which he’ll be ready to announce right away.”
I type up my notes, trying to stay focused on the hearing preparation I’m not even sure I’m supposed to be doing, and ignore them. What do they know, anyway?
Apparently, though, they know a lot more than I knew when I starting work here. I’d never heard of Asher Marks’s… proclivities. And I’d never have dreamed that he’d want me. Or that I would give in to him.
But now, all I want is for him to come back and explain himself. How dare he use me like that, and then leave me?
Unless it’s just part of his game. The mysterious rules to which he always alludes but never explains. He probably likes making me wait, letting me know who’s boss, as if I could possibly forget.
Asher might be jerking me around, but I’m choosing to stay the course until he returns and lets me know what’s going on. If he lets me know what’s going on. I wouldn’t put anything past that man, at this point.
I want to be mad at him, but all I can think about are his hands on my breasts, my ass, my pussy. His big cock in my mouth. The way he fucks me.
He wanted to fuck me so badly and he did. But it was on my timetable. So maybe that’s why he freaked out and left.
And I know I could be wrong but I feel certain he wants something more from me, too.
So I will wait him out.
I’m mid-way through reading a deposition transcript in the Schwartz case to prepare for the hearing when I realize I don’t have part of it. So I go up to the fifteenth floor so I can look for it in his office.
His assistant Dora nods to me as I duck into his office. She’s used to seeing me in here by now. I’m sure she has some idea that it’s not all work and no play—everyone at the firm seems too— but she never lets on. She only ever asks me if I need anything. I’ll ask her to find the rest of the deposition transcript if I can’t find it.
I root around on his desk and then look up on his bookshelves. The phone on his desk rings, and I jump. Then I look at it with curiosity.
“Dora?” I call out.
There’s no answer.
I peek my head out to where her desk is but she isn’t there. She must be in the file room or copy room.
What if he’s calling trying to get through to her? What if he needs her?
I know it’s just an excuse to try to talk to him. But I pick up the phone, telling myself that if it’s not him I’ll just pretend to be Dora. And if it is his him, I’ll see how he reacts before determining how to proceed.
“Asher Marks’ office,” I say confidently, as if answering his phone was a normal part of my job.
“Who is this?” a woman’s voice says on the other line.
“Excuse me?” I ask. Then I clear my throat. I have to remember to stay professional. “This is his… assistant,” I lie.
“This is not Dora,” the woman says.
Shit.
“When I say assistant, I mean associate,” I quickly correct myself. He might kill me if he finds out I was answering his phone pretending to be someone else but I don’t know what else to do. “This is Madilyn.”
“Oh Madilyn, is it?” the woman says. “So that’s your new name. But it doesn’t make any difference.”
“Excuse me?” I ask her.
“You’re his newest pet, of course. But you’re all the same. It’s not worth learning your name when you’ll be gone before I know it and he’ll be onto the next one.”
“Who is this?” I demand again, very angry now.
“You can tell him his wife called,” she says, and hangs up.
His wife?
What the ever living fuck?
I knew Asher was mysterious but this is an all time low.
Just when I thought things were different between us, I realize they’re really not. She’s right. Not only am I one in a long list of foolish associates he’s “mentored” over the years but I’m probably the only one dumb enough not to have known he was married.
He may have fooled me once, but not again. I regret ever losing my virginity to him.
But as I look down at the same desk on which he fucked me silly, I have to admit to myself that that’s not true. It was a hell of a way to lose my virginity, even if it turned out to be a lot shallower of a “relationship” than I thought it was.
Chapter 31 – Asher
I haven’t seen Madilyn in days.
And even though I want to, I know I can’t.
I’m coming close to falling for her in a way that is much too dangerous.
I can’t believe she lied to me. That she’s still with Jimmy even though she claimed they were over for good. I can’t believe I let myself be taken for such a fool.
So I did what I had to do: I got far, far away.
All the way to the South Pole, in fact.
Nolan, a climbing friend of mine, had been bugging me for months to join him on a yacht based expedition of the Antarctic Peninsula that he’d been planning to take this week.
Initially I’d told him to just borrow my yacht and go without me, because I would be too busy with work. But that was only half true.
Sure, I have a big trial coming up in the Schwartz Capital case, for which I really should be preparing. I hope that Madilyn is as good of an associate as she is a pet, because I’m entrusting her with the case in my absence. She just doesn’t know the specifics or length of my absence, or the level at which I’m entrusting her.
The main reason I’d told Nolan I couldn’t go on this trip was that I was expecting to be grooming my next pet. Madilyn. But everything with her happened much more quickly than I’d anticipated; much more quickly than it usually does. And I didn’t know what to do to slow it down, except to tell Nolan to count me in on his trip.
Now, though, I’m wondering if it was really such a good idea. I’m off my game in every aspect of my life.
Sure, the trip has been great, and the scenery has been breathtaking so far. Nolan and some of his finance buddies and I had boarded in Ushuaia and departed for Drake Passage, sailing Port Williams, Chile. We’d enjoyed a short climb in Port Lockroy and then a longer climb on Mt. Lopez, on Doumer Island.
We’d headed down the Graham Coast, as far as Prospect Point, and we’d just spent two days skiing and climbing, but it didn’t clear my head like it normally does. And I had a scary
slip off of a secure hold, which isn’t like me at all.
“Dude, are you all right?” Nolan had asked, as he helped me up.
“Yeah, I’m just not feeling too great,” I’d told him.
He looked at me funny.
“The last time you slipped during a climb—”
“It’s nothing like that,” I’d quickly protested, knowing he was thinking of my divorce.
My ex wife and I had tried for a long time to make it work, but when we finally called it quits, the break up really fucked with my head.
It’s nothing like that at all, I’d repeated mentally, as if trying to convince myself it was true as much as I was trying to convince Nolan.
“Have you even talked to her lately?” he asked, raising a concerned eyebrow.
“No. No, I haven’t.”
Which was true, although I’d left some details out, that he didn’t need to know about. My ex wife did call me last week but that’s nothing out of the ordinary.
She likes to call every time the new associates start working because she knows I might be choosing a new pet. She has a ridiculous theory that I’m only using them as substitutes for her, and none of them are good enough so I have to keep “churning and burning through them,” as she puts it. She thinks I purposefully pick pets that aren’t right for me so that I don’t get attached to them.
Even years after our divorce, she still likes to be cruel to me. I know that she’s not correct in her theory.
I know that my pets are my diversion, and that the reason I rotate them rather quickly is so that I don’t get close enough to them to allow any of them to hurt me the way she did. It’s easier and more fun that way and she’s just jealous and angry that I’m no longer available to be her emotional punching bag.
I ignored her call, not wanting to get into it with her. Usually I show myself I’m the bigger person by picking up the phone and telling her to fuck off, but right now I don’t want to deal with her. I have enough on my plate.
I’m sure she’ll continue to call. But I’m too far away to be reached so she can just listen to the phone ring and ring and ring. For the first time since our divorce, I really think I’m fucking over her.
Yes Boss: A Bad Boy Office Romance Page 11