I slap the other side, and she tenses up, but doesn’t say anything. She just sucks in a deep breath. I squeeze her ass cheek, which feels firm but malleable in my hand.
I rub my finger up and down her clit, and she shivers. I know she wants me to do more. I almost feel myself giving in to her desire and my urge to feel myself deep inside her.
But I remember my rules. I may have forgotten or bent most of them for her before and I’m even breaking too many now. I shouldn’t be going this far yet. I shouldn’t be giving her so much control.
I want her so bad. I want her in a way I’ve never wanted anyone. I can’t even think.
I need to take charge quickly. But I still need a release that I would usually be disciplined enough to wait longer for.
I squeeze her clit and say, “Get on your knees and show me how much you want to be my pet.”
I unzip my pants and she kneels down in front of me, eagerly grabbing my cock and beginning to pump its shaft while she licks its head. Her sparkling blue eyes look up at me with a mixture of innocence and naughtiness.
I grab a hold of her nipples and twist them in my fingers. As she sucks on the top of my cock and then takes me all the way deep inside her mouth, I lean my head back so that she can’t see the look on my face.
I know it’s a look of vulnerability, of letting go and giving in to whatever it is that she is doing to me— and however she is doing it so well. I had no idea a virgin could give such a good blowjob.
I give in to my basest of desires while realizing she’s fulfilling something deep inside me that I didn’t know I needed. I feel my cock start to swell in her mouth, as she pushes it all the way inside her throat.
“Madilyn, Madilyn, Madilyn,” I moan, as my cock pulses and throbs.
Too late, I remember my rule about not saying their names. I can’t give them too much power.
But she’s not like the ones who came before her. Something about her has overtaken me the way I thought I would overtake her.
“My pet, my pet…” I groan, as my cum shoots into her mouth.
I’m breaking all my rules for her and she doesn’t even know it. She laps up my cum and swallows it, but some of it still drips down her chin and neck.
“That’s a good little pet,” I tell her, taking my cock out of her mouth and rubbing it all over her face, the way I’d meant to do before I’d cum inside her mouth.
But it had felt so good. It was the release I’d needed.
And it’s opened up something in me that I didn’t even know was there.
Chapter 30 – Madilyn
THE NEXT DAY
Every boss knows he’s not supposed to fuck his employee. But Asher Isaacs is known for doing things he’s not supposed to do. And it looks like I’m one of those forbidden things he wants to do. The thing that surprises me is how bad I want to do it too.
Today I had worn my red panties that he likes along with a black and white lace bra. When I was getting dressed this morning I just knew that today is the day I will lose my virginity. My older, experienced, powerful boss will take it and I’ll let him and I’ll probably regret it afterwards but I sure will enjoy it in the moment.
But first, there’s something I need to do. And that is talk to him.
He had messaged me to come to his office at six p.m. to talk about the Schwartz Capital case. But I go up at 5:45. The hallway is empty. The senior partners rarely have to work late. And their assistants are the most experienced and useful so they get the benefit of getting to go home earlier than a lot of the other assistants on other floors.
I sit on Asher’s desk, much like Mandy was on that dreadful day I’d overheard her. But this time I’m in charge.
He walks in at five to six, obviously having been at the firm gym. He’s wearing a wife-beater and running shorts and he’s a sweaty mess. There’s a shower at the firm gym but he obviously hadn’t been planning to fuck me tonight because he didn’t use it.
The look of shock that crosses his face confirms my suspicion.
“Madilyn,” he says, quickly shutting the door behind him and locking it. “You’re early. And you’re on my desk.”
“Yes, Boss,” I tell him, trying not to smile at his shocked face.
I know he’s surprised but I need to accept that I’m no pushover. I enjoy being submissive and I even like the power imbalance in our relationship, if it’s even a relationship. But if I’m going to lose my virginity to him, I need him to hear me out.
“I wasn’t planning to…” he says, looking around as if other people might be in the room. He clearly doesn’t like when he’s not the one in charge.
“I was planning to go over some things in the Swartz case,” he finally says.
“I know,” I tell him. “And we can do that if you want. We can do anything you want, Boss.”
A look of pleasure crosses his face and I know that he likes the way I call him boss and tell him he can do what he wants.
“I just wanted to tell you that I’m not like the girls you’ve had in the past. If you want to be with me, you’re going to have to accept that.”
“I know,” he says, quickly, as if he’s already thought about it.
He purses his lip and a crease appears across his forehead. I can tell that he doesn’t exactly like the way things are going so I decide to make it a little easier on him.
I open my legs a bit so that he can see my red panties.
“I appreciate the way you stood up to me to Mandy,” I tell him. “I’m glad you didn’t see me as some secret, dirty fling.”
“Mandy is a horrible human being,” he tells me, stepping closer and running his hands along my knees and then my inner thighs.
It starts to drive me crazy but I try to stay focused.
“I’m sorry I tried to replace you with her temporarily,” he says. “But it didn’t work out. She wasn’t you.”
He kisses me and I feel a wave of heat wash through my entire body. Then he pulls away and looks me up and down, his hands traveling all over me just as much as his eyes are. I love the smell of his natural sweat and the way it looks when it glistens on his hardened muscles.
I can see a tattoo peeking through his shirt opening and I love the fact that he has ink on his chest. I never thought I would like a guy with a tattoo but it suits him perfectly.
“You’re beautiful,” he says. “I love every inch of you. Everything that Mandy said was just out of jealousy.”
He pushes me back on his desk and then he spreads my legs open wide. He gets down on his hands and knees and pulls my panties to the side.
“You have made me come completely fucking undone,” he says. “Do you have any idea what you do to me? I think I may have met my match.”
I raise my head a bit to smile at him as he begins to lick my pussy. His tender kisses on my clit turn into heavy pressure from his tongue and he licks my clit up and down and then begins to suck on it.
“Oh my God,” I whimper, the best fantasies from my wildest imagination coming true. I lie back and let him alternate between teasing my clit with his lips and then pushing his tongue into my wet opening.
“I feel so good.”
I grab onto his thick hair as he takes my clit in his mouth and chews and sucks on it to the point where I can barely stand it.
“I’m coming,” I tell him, lifting up my hips so that my pussy meets his mouth even more as his tongue strokes my hole and his lips suck on my clit. “It feels amazing. I can’t breathe…”
My words turn into moans and groans as I surrender to the sweet feeling of his mouth all over my pussy. I come so much that my juices are gushing out of me.
“Oh wow,” I say, lying back on his desk and panting.
He stands up.
“Are you satisfied?” he asks, pulling me up rather roughly. “You’ve had your fun with me. Now I get to have mine with you.”
I can tell that he’s not exactly thrilled about the fact that I came to his office and basically made him gi
ve me oral sex. But the pink in his cheeks lets me know he’ll forgive me and he’s ready for round two.
He picks me up and I wrap my legs around him. He kisses me as he takes my shirt off. He looks at my bra approvingly. Then he puts me down and turns me around. He tugs off my skirt and rips off my panties.
“I know you’re a virgin,” he says, as he bends me over his desk. “So I’ll go easy on you.”
“This is easy?” I ask, as I feel his hands tighten around my waist at the same time I feel his large package swell up against the back of my skirt.
“Oh I’ll show you hard,” he says. “In fact, you’re feeling it right now. But everything is about to get a whole lot harder.”
I lean into him, feeling his six pack abs against my back and his throbbing cock against my ass.
“How did you know I was a virgin?” I ask him.
“I know everything,” he says.
He puts his finger into my pussy and says, “It’s so tight in there. I knew you were a virgin but I didn’t know you would feel this good.”
He pauses to take a breath and I love how he’s overcome with desire for me. But soon he has regained his normal gruff composure.
“Now do you want me to fuck you or not?”
“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 31 – 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 her 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 it 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 bit 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 like 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 32 – 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 Isaacs 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.
SEAL's Virgin: A Bad Boy Military Romance Page 25
