“I’m going to fuck your ass,” I tell her. “You’ve been a bad pet and I have to punish you.”
I reach down on the floor to where my belt is. I spank her ass once, twice, three times with it, and she jumps a little higher each time.
“Do you like when I punish you?” I ask her.
“Yes, Boss,” she says, her eyes squeezing back tears.
“If I get too rough, just tell me to stop,” I tell her. “I don’t want to punish my pet too harshly.”
“Yes, Boss,” she says. “But I like it.”
“You do?” I ask, and hit her again with the belt.
Whap.
“Yes,” she says, as the marks I’m making on her skin redden.
I squeeze the areas that appear, claiming her as my own.
“I don’t know why I’m being punished, Boss, but you’re free to do with me what you want.”
“Good,” I tell her, as I thrust my cock into her ass hole.
“Ow,” she moans, but then she breathes deeply and relaxes, allowing me further in.
“Because I wanted this. Your ass. Your anal virginity.”
I play with her clit with one hand and her nipple with my other and feel her come again while I fuck her ass. I thrust my cock in and out her small ass hole, tearing it up.
“Oh my god, Oh my god, Oh my god,” she moans, and I love the sound of her pleasure mixed with pain.
I love it so much I’m going to come.
“Holy fuck,” I shout, as I let my load loose inside her.
She moans, and I walk over and fall back into the chair, not even bothering to pull up my pants. I’m exhausted. I’m spent. And I know I’m way too into Madilyn St. Clair to back out now.
Chapter 36 – Madilyn
I walk into work excited for what the day will bring. Last night after we had sex Asher told me that he needs to talk to me about some things but that we should both go home and catch up on sleep first. He said he wants to take me to dinner tonight.
I hope what he wants to talk about involves his “wife.” But I’m also so happy to be going on a real date with him that I don’t really care what we talk about.
As soon as I get into work, Monique tells me that my real office will be ready to move into by the end of the week.
I have a feeling that Asher’s behind this move— as he is everything at the firm, or at least everything that affects me— and so I log onto the firm’s instant message program.
In the back of my mind, there’s a big fear that being with Asher can have negative repercussions on my career. It’s funny, because at first I was afraid that everything had been building up to the last hurrah— sex in his office— and, as much as I’d wanted it, I’d feared that as soon as he took my virginity, that would mark the end of our “relationship.”
Instead, I feel that it marked the beginning of something. The beginning of us.
And if nothing else it’s marked a phase in my life where I’ve learned the power of letting go, of giving in to something I want so badly but that I would have been afraid to take in the past.
It feels good to not only be the over achieving associate anymore. It feels good to be the boss’s pet, to let him tell me what to do, and to do it with eagerness and submission.
I know that Asher’s too prideful to admit it, but he’s smitten with me. And the feeling is quite mutual.
I don’t fool myself that I can be different from his other string of mentees— all right, sometimes I do. I don’t fool myself that I can change him, soften him— all right, sometimes I do.
But I do know that he has a certain weakness for me, and that he and I are already different than he and any other former pet. It’s been quite a rollercoaster ride but I’ve been a happy passenger.
I decide to just assume that he’s behind the office move, and to thank him over instant message.
Madilyn St. Clair: Thanks, Boss.
Asher Marks: No sweat. I figured you’d need your own, quiet space to get ready to argue the upcoming hearing in the Schwartz Capital case.
Madilyn St. Clair: Really?
I let out a squeal, and then turn around wondering who heard it. Some other paralegals shoot me annoyed glances, but many of them have headphones on, translating dictation, or they’re too busy typing away to be bothered by my outburst.
I don’t know of any other new associate who would be given such an opportunity. I can’t believe I’ve gone from summarizer of Janice’s deposition transcripts to head arguer at a big dispositive motion hearing for an important client of Asher. And from new, ostracized associate to his mentee.
Cankles and all.
Asher is definitely good for both my professional and personal life. And I know he feels the same about me.
Madilyn St. Clair: Thank you, thank you, thank you, Boss!
Asher Marks: You’re welcome, Madilyn. Anything for you. Also, true to my word I’d like to take you to dinner. At the Alcove tonight at 6:30 pm. I've made reservations.
My entire body tingles with anticipation of an actual date with Asher. I can’t help but think that this means we’re taking things to an entirely new level. I’ve been his pet for a while now, but does he want me to be something more as well?
I’m not sure, but I know that it’s what I want. And I’ve learned from him to go after what I want. No matter how scary or risky it might feel.
Chapter 37 – Madilyn
At 6:30 on the dot I walk into the Alcove and let the host know that I'm there with Asher Marks. It's a fancy restaurant in a resort hotel high up in the mountains, and it took me about half an hour to drive here.
I decide to surprise Asher a little bit. I’m wearing my fishnet stockings— which are thigh-highs and have lace on top of them— and sexy little black dress. Before I left home I topped off my ensemble with a blazer so that I still look professional, yet underneath I'm wearing a new tiny G-string thong with lace and bows and my sexiest push-up bra.
"This way, Madam," the host says, and leads me to Asher.
My face flashes bright red when I see him, and I swear I get weak in the knees.
"Hello there, Mr. Marks," I say, smiling coyly as I take my seat.
“Ms. St. Clair.” He smiles at me in an adorable mix of awkwardness and sweetness. Then he tells the host, "She'll have some of this Chianti."
“How do you know that’s my favorite?” I beam at him.
The host pours the wine into my glass and proceeds to tell us about the specials. This restaurant is so expensive that I've never been here. I can barely understand the names of the foods he's reciting. I figure that's fine, since Asher will probably order my meal for me anyway.
“To us,” Asher says, raising his glass to me.
“To us.”
As we clink our glasses together, a chill runs through me, but it’s the good kind. I like the way he said “us.”
Asher does order for me, as I predicted, but I'm happy with the choice since it's something I would have ordered myself— the filet mignon. It surprises me how well he knows me.
In the middle of dinner, he reaches for my hand across the table, which surprises me, and says, "I need to tell you something. I was very upset with you and that’s why I left.”
“What?”
I swallow the bite of meat in my mouth and look at him in surprise.
“I saw what Jimmy posted on your Facebook page,” he tells me.
“What?”
Now I’m even more surprised.
“You go on my Facebook page? You know about Jimmy? I mean, other than what I’ve told you?”
He glares at me, as if he has the right to be mad at me for being mad at him for doing this stuff. It borders on stalker-like behavior. But I have to admit, it gets me kind of hot. He was obviously more into me than he was even letting on.
“If you haven’t been able to tell, I’m not a man who likes to share.”
He shrugs, and takes a drink of his wine.
He’s got that right. I kno
w he’s a possessive, demanding man. A take charge guy who knows what he wants and goes for it and doesn’t accept anything less. And it’s exactly why I like him. So what am I so upset about?
“It’s not what you think,” I tell him. “And I wish you would have just asked me before running off to the edge of the universe.”
He raises an eyebrow at me.
“Tell me the whole truth.”
“The whole truth is that he came over before you and I ever had sex. It was definitely over when I told you it was.”
I take a breath.
“Well actually…”
“Uh huh,” he says, with a smug look on his face.
God. I hate that he’s right. It was kind of same old same old with Jimmy before Asher left. Perhaps it took him leaving to get me to realize what I needed to do to save any kind of relationship I hoped to have with him. And to save myself.
“Well, I was never very good at breaking it off with him no matter how many times I tried,” I admit. “But I had really tried. He just wasn’t taking the hint very well. But it was before you and I had had sex. And it wasn’t, like, some romantic night at home watching TV like he tried to portray to me on Facebook. I got really mad at him about that. I ended it with him for good this time. I promise.”
I look at him eagerly, begging him to believe me.
“I know,” he says, with a shrug.
“You know?”
I try to think about whether I or anyone else posted anything on Facebook to confirm that it was over.
“I can just tell,” he explains. “I know you.”
He looks me straight in the eyes and I look back at him, knowing that he does know me and loving that about him.
“Well since we’re here talking about other relationships,” I say.
“Oh no,” he says, shaking his head. “You’re the one with the psycho ex posting on your Facebook page.”
“And you’re the one with the wife calling your office,” I shoot back at him.
“What?”
Now it’s his turn to look shocked. I explain to him what happened with the call at his office.
“She would say she’s my wife,” he says. “Just to get at you. But we got divorced over five years ago.”
I look at him and see a mix of pain and defiance on his face. I can tell he’s over her but that the journey to getting there hadn’t been easy.
“You know my tattoo?” he asks. I nod.
“After my ex and I got divorced and everything was finalized, I went to Katmandu for an extended mountain climbing trip and decided to start over. Rebirth. For myself, for my dreams, for what never was.”
I look at him, knowing that he’ll continue if I don’t press too hard.
“My ex and I went to a lot of different fertility doctors, trying to get pregnant. We never could. They didn’t really know why. She blamed me. Everything was my fault. She became so cruel. I couldn’t take it anymore.”
I nod.
“It’s for the best that we didn’t have a baby,” he says. “I don’t even know if I wanted one.”
He starts to say more but stops. And I start to feel more. I didn’t think I wanted kids before but maybe it was just because I was with Jimmy. With Asher, I feel like the possibilities are endless.
I squeeze his hand.
“I understand. Thank you for telling me.”
“I’m glad we got that cleared out of the way,” he says, and we both breathe a sigh of relief.
“Oh my god.”
I see someone walking in and quickly remove my hand from Asher’s.
“What?” He turns around and sees who I’m looking at. It’s Janice. And she’s looking straight at us.
“Hello, Janice,” he says loudly, nodding in her direction.
She gives a strained smile and says, “Hello Asher. Hello Madilyn.”
“Oh my God.”
I just wish I could die of embarrassment. I know that everyone knows we don’t have a strictly business “relationship” but now it’s going to be quite public.
“Don’t worry about her,” Asher says between his teeth and he flashes her another fake smile. “She’s just jealous. She wanted to be with me way back before I even got with my wife. She’s never gotten over it.”
I can barely suppress my laughter.
“We’re just on a business dinner, discussing preparation for the Swartz case,” he says. “That’s all she needs to know.”
“Yeah, I always wear fishnet stockings to business dinners with my boss,” I tell him.
I wink at him.
His foot touches mine under the table and I lift mine up in return. It’s like we’re in middle school, playing footsies.
He rubs his leg up against mine and says, "I really do like those pantyhose. It's nice to see you in something different from the normal office wear. And I have a special surprise for you.”
He takes something out of his wallet and flashes it at me. It’s a room key card.
“Really?” I ask, my excitement rising.
"I thought we needed to spend some more time together. We have a big case we have to work long and hard on, after all."
Now it’s his turn to wink, as I know we’re both thinking of what else is long and hard. My heart races at the thought of having a hotel room to ourselves. We've only ever made love at work in his office. Tonight we're taking things to a whole new level. I guess I had expected and hoped for as much— hence the sexy underwear— but I really didn’t know what to expect. To have a room to ourselves is something altogether new and different.
The waiter returns and Asher orders us dessert. He reaches his hand under the table and places it in between my legs. At various points while talking to the waiter about which dessert we should get, he places his fingers under my panties and inserts them into my pussy, which continually becomes wetter and wetter for him. He also rubs my clit. I swear it causes me to squirm a little bit, but if the waiter notices, he doesn't mind. I keep sneaking peeks at the table where Janice has been seated across the room, but she seems to be purposefully trying to not look over in our direction.
“We’ll have the tiramisu,” Asher finally decides.
As the waiter walks away, with a quick flick of his wrist Asher drops the room key card under the table.
"Oh look at that. Oops. I've dropped something. See?"
He holds up an end of the tablecloth and at the same time, with his leg nudges my left leg further apart from my right leg.
Then he raises a mischievous eyebrow and bends down to look under the table. As he does so, he moves my panties away from my pussy, so that it's exposed to him.
“Oh where oh where could I have put it?” he asks.
I can’t believe how brazen he’s being. But I love it. I had never in my life imagined showing my pussy to my boss at a nice restaurant but because it was his idea, I don't even mind. In fact, I'm filled with a strange excitement.
Asher inserts a finger into and out of my pussy several times while he continues to look around under the table for the card.
Then he says, “I see it and it’s on your side of the table. Do you think you could help me out with that?"
I quickly look around but don't see the waiter anywhere in sight, and Janice still isn’t looking in our direction. I duck under the table and crawl towards the key card, my ass sticking up in the air for Asher to see under the table. I pull my skirt up high, so that he can get a good look. My underwear are still over to the side where he had pulled them before fingering me, so that my ass and pussy are naked. As I crawl, however, my panties slide back a bit, almost back into their original place.
"I have your card, Boss," I say sweetly. "It's right under here."
"You'd better return it to me then," Asher says.
I turn so that my ass is facing him again and to my surprise he reaches under the table and pulls my underwear back over to the side and uses the strap to pull me back close to him. Surprised, I sit down with my ass on his shoes,
and then, feeling as if this is my cue to do something sexy, rub my ass up and down on his leg.
"You really are a good associate," says Asher, nudging me back up onto all fours with his shoe, and inserting a finger into my pussy as he does. I can't believe how bold he's being— even bolder than he is at the office.
I lean back into his finger and he says, "I can tell you like helping me find my key card and whatever else I need you to do," while he plays with my asshole with his thumb. He is really enjoying himself, having his way with my exposed pussy and ass, and I let him play until he's good and ready to be done. Then he reaches a hand under the table and squeezes my right nipple and then my left. I begin to wish that we were the only people in the restaurant, because I could do this all night.
"You assist in any way possible," Asher says. "And you happily go the extra mile to make your boss happy."
Finally he pinches my ass and lightly slaps my ass as my cue to stand back up. I pull my panties back to their rightful place and pull my skirt back down and then sit back up at the table. I glance around, incredulous that no one noticed this obvious sexual display, but everyone seems to be eating their dinner as normal. The waiter is walking over to us with our dessert, so Asher had told me to get up just in time.
“We need to eat this dessert fast and then have fun with this key card that you so graciously rescued,” Asher says. “I'm so glad it wasn't lost for good."
Chapter 38 – Madilyn
At long last, Asher and I are finally alone. In the elevator from the restaurant floor of the resort to our room, he fingers me repeatedly while kissing my neck and the top of my breasts.
“I’m so happy we get to do this,” I tell him.
When the elevator door opens, Asher picks me up and carries me with my legs around him to our room. He opens the door to a spacious master suite and it's immediately clear that he'd been in here earlier, before meeting me for dinner. There are handcuffs tied to the bedposts, a blindfold, and a scarf.
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