BOSSY

(4,990 words / 22 mins)

♀♀ / ♂

A novice Domme with a demanding job is celebrated for an accomplishment at work, under the direction and guidance of her powerful, experienced boss.

!!!!!!!!!

My heart tumbled as the alert came in. I knew before I even opened the message, and as I did another one quickly followed.

We closed it!!! I can’t believe it. I am SO fucking excited!!

A wave of feelings tumbled through me, with such a variety at once; relief, excitement, pride, dread, anticipation. I responded with a slew of celebratory emojis and exclamation points, and it was genuine. I really was glad that she had accomplished something, I really was proud of her. I was amazed, even, to see the growth that it represented and to know she was becoming stronger, and more powerful. But I knew what it meant. What it would mean by the time it was all done with. And I wondered what they had in store for me now.

Alyssa had been smitten with and even enamored of Marlena since the beginning, since she signed on at the firm as Marlena’s assistant, on the way to becoming a real estate broker. It was such a big step into a demanding but promising career (with what she proudly referred to as “high earning potential”), a step away from her disappointment and dissatisfaction in retail and restaurant work, and over the two months she had been working there I was so proud of her and her efforts. She had such ambition, such drive, such a desire to learn and to fulfill her potential as a career-driven woman.

Every day when she came home she gave me the play by play, and we sorted through the ongoing drama together. I listened to the minutiae of the day, but when that had been run through it always, always came back to her mentor, her boss. She had been excited by and admiring of Marlena from the first interview, and from the first day on the job she had confessed a huge crush on her. I thought it was sweet how much she admired her, as a boss, as an empowered woman, as so many things she herself aspired to be. She was humbled and inspired by her, and she frequently confessed a sincere attraction to her as well.

“Soooo fucking hot,” she had intoned one night as she had described how she had watched Marlena standing up to the corporate boy’s club to which she answered within the organization, and the way she spoke on the phone with such authority and determination.

She had been newly exploring her bisexuality when we met and got together, and Marlena was a frequent topic of conversation even then. She fantasized with me openly about her desires to be disciplined and sexually exploited by her, her desire to support her and enable her, to be bent to and shaped by Marlena’s will. It fed into her own budding dominance, and the desire she had for growth and education.

Some nights she was thrilled, having pleased her or proven herself, some nights she was distraught and sobbing over some misstep or mistake. It was a high pressure but high payoff environment, and by all accounts Marlena was relentless. She apparently had developed an intimidating reputation within the company and had lost a couple of past assistants with her tendency to push them too hard and dress them down on occasion. But when she approved of and praised her, Alyssa was in heaven.

“She’s just amazing,” she often said. “She’s so inspiring and she’s what I want to be.”

I had a picture come in on my phone. “Today’s a big day,” the message said, beneath a shot of her velvet ankle boots.

I trembled as I reread that phrase, and I knew this was something Marlena was encouraging, even in that very moment, the way she had all along. It must have been her taking the pictures too, because another one came in from a lower angle, looking up at Alyssa’s overjoyed expression. One of her ankles was flexed back and the worn sole of her boot was showing, and my eyes darted to the next image as it appeared, seeing her point down at it and grin.

I tried to sound relaxed and casual, asking where we were going to celebrate, and she took an agonizing moment to respond:

Just come pick me up here. 6:00.

“Sounds good,” I started typing, glancing at the clock and doing the math in my head as I hit send, and then I went in to the bathroom and turned on the shower.

As the hot water ran over me and the room filled with steam I remembered the last time Alyssa had grinned that same empowered and ambitious grin, the way she had talked so proudly and excitedly after closing her first sale. She had met me at one of her favorite restaurants downtown, a dark, intimate place with thick white tablecloths, and as the first plates had hit the table she started telling me about what Marlena had said.

“And she said she was seeing more and more potential in me,” I remembered her saying as I closed my eyes and stuck my head under the spraying water.

An hour later I was winding through the roads of the industrial office park, pulling into the parking lot at their building. It was nearly empty, and as I went inside I was struck by how different the place felt when almost everyone had gone home, how strange it was when there was no one in the hallways or waiting for the elevator. The only real sign of life I heard was when the doors opened on the third floor, and I could hear them talking excitedly, and laughing.

The place got warmer as I found my way through the front of their office and down the hall to Marlena’s, where they were waiting, sitting in the big, cushy rolling chairs, a bottle of red and a couple of glasses set out on the table between them, and Alyssa grinned happily again as I walked through the door.

I expected her to get up and come to me, the way she usually did whenever I visited her at work, but Marlena reached over and gently rested her hand on Alyssa’s wrist on the armrest, smiling at both of us as I approached them. They finished the last few words of their conversation, and then they turned to me as I stood in front of them.

“Well,” she said looking proudly back at Alyssa, “are you ready?”

Alyssa grinned so hard at her, her tongue slipping forward against her teeth, leaning back and subtly pushing her breasts in Marlena’s direction, and she nodded slowly.

They both turned back to me and Marlena spoke again. “And you,” she said, “what do you think of this?”

I fumbled slightly, being so unexpectedly put on the spot, but I managed that I was happy and proud of Alyssa.

“You should be proud,” she said, rubbing Alyssa’s wrist slowly, “your girlfriend has made quite an accomplishment.” She raised her chin and looked at me sideways. “And you remember what this means, yes? As we discussed?”

“Yes ma’am,” I responded, the way she and Alyssa had agreed.

Alyssa had also been exploring D/s when we got together, and we had talked about it a number of times over the preceding months and even incorporated it in an adventurous way into some of our alone time together (a little light bondage and teasing), but things had gotten more and more serious as her time with Marlena went on. It hadn’t come to a head yet, but she had always told me what a fascination working with Marlena brought her, how enthralled she was by her power, and how desperately she wanted to be taught and trained by her.

She had come home one night in a frenzy, thrilled and anxious to tell me what she had learned about her boss, how she had gone into her office one morning looking for an extra stapler and found a dildo and vibrator in her desk drawer. She gave me the whole story about how conflicted she was about asking her about it, how she hemmed and hawed about starting the conversation, but they had gotten close over the month or so they had worked together, and she got up the nerve.

“That’s not even it,” she said breathlessly as she told me what Marlena had told her. “She pulled up her dress and showed me she was wearing this harness for it, and she said sometimes she puts it on and wears it all day.” I was shocked and surprised, but Alyssa continued. “She said whenever she writes an email to her supervisors or makes a phone call, any time she has to negotiate or argue or complain, she puts her dildo on and drops the vibrator into her panties.”

I imagined the words in Marlena’s voice. It’s just to remind me that my dick is bigger than theirs, and that this is about what I want.

That had gotten both of our hearts pounding, the horny, ferocious audacity of it, and we had both relished and marveled at her nerve. We had laid there panting after an intense pair of orgasms, and she sat up on her side and breathlessly told me, “I want that.”

On the night of her first sale, she told me as we ate at that restaurant how Marlena had been inspiring her to be more assertive and forceful, and how she had taught her the importance of her sexuality in developing a prowess of her own. “She said I had to keep myself satisfied and hungry at the same time. She said I needed a fire that demanded satisfaction.”

We had spoken on the phone the next morning, a conference call where I could tell they were together in the same office, and they called me at home while I was still in bed. I remember her voice and the way she talked to me so assertively, and I wondered whether she was wearing her cock. And then I wondered when she would buy one for Alyssa.

We ‘talked numbers’ for a while, Marlena explaining their goals for the next three months and talking about how serious she was about meeting them, and how she had a plan that would make it happen. The way it was sounding, she and Alyssa would be working incredibly hard over the next few weeks and Alyssa would need all the support I could give her.

“Are you capable of that?” I remember her asking.

She talked to me a little bit about my role in facilitating that, about taking on more of the household chores on an ongoing basis and making Alyssa’s meals so she wouldn’t have to worry about it, and then she gave me some instructions. She said that she wanted Alyssa’s pussy eaten every night, and then once again every morning before she came in. She said she also wanted my cock to be available for her on demand, and that when we had penetrative sex I was always to begin by laying on my back and letting her ride me until she told me how she wanted it next.

“Can you do that?” she asked me forcefully.

“Yes,” I remember responding, shocked and overwhelmed but feeling dutiful and disciplined, as in awe of her power as Alyssa was, and she said goodbye for both of them and told me Alyssa would have more instructions when she got home. I was so hard when she hung up the phone, and I came intensely as I wondered where this would go, where Marlena’s leadership would take us.

That night Alyssa came home with a purpose, and she gave me an idea of what she stood to make for the quarter if things went according to plan. It was an amount that could change our lives dramatically, and I could tell her ambition and appetite for it were inflamed. She intoned that she and Marlena had discussed a number of things, strategies and plans and estimates, and then she laid the final piece on the table.

“And she said that if we make it, if I can prove myself in these next three months, then she will train me as a partner and teach me how to harness and push my sexual energy as means of driving achievement.”

I was dumbstruck, and I even trembled slightly as she continued.

“But she says that to do that I need a strong and willing domestic partner to subordinate, one who can serve me and support me and be subject to my will and my intentions.”

We agreed that the last few months of our relationship had been amazing, and that with or without Marlena’s guidance this was where things were heading. Alyssa had been getting stronger and stronger, and more in charge of everything, and it trickled into the bedroom too. I was growing too, growing more and more proud of her, and feeling so humbled to nurture and encourage her. I took her hand, and I looked into her eyes, and I agreed.

She sighed with relief, accepting and appreciative, and then she reached for her laptop bag and pulled out a piece of paper with Marlena’s letterhead.

“She says if you’re willing she’ll require a demonstration of intent.”

She took me to the bedroom and laid the piece of paper on the foot of the bed, and she asked me to stand in front of it, clearly following Marlena’s directions.

She asked me to pull down my pants and start masturbating, reaching in the nightstand and handing me the lube, and as I did she undressed and laid down on the bed. I looked at her naked body, and she started touching and caressing herself as she moved from one pose into another, showing it off and letting it strike me.

She laid on her back and opened her legs, showing me her vagina and beginning to slide her fingers against it. She sped up and rubbed her clit, swirling her fingers around it and stroking her hole underneath, and I watched her get wetter and more swollen as she played with herself. She locked eyes with me and her breath got tight, and she looked down at her crotch and then back up at me as she spoke.

“Are you devoted?” she asked. “Are you devoted to me and my pussy? Are you devoted to my sex and my success?”

“Yes,” I responded, grunting and surging as the word slipped past my lips, and she flexed her feet and raised them up in front of me.

“If you accept and agree, you’re to lean forward, put your face in my feet, and cum on the piece of paper.”

My neck tensed and my spine tingled, a rush pouring through me, and I looked at the soles of her feet. I made eye contact again, and she shuddered and gasped as she held them, and then it got more and more intense and I looked back and forth between her and her feet, and then all at once I stepped forward, and obeyed.

The next morning I got an email from Marlena, informing me matter-of-factly of some rules and policies she had put in place for Alyssa’s “sexual wellbeing”, which included that she was always to cum before I did whenever we had sex, and that she wasn’t to allow me to cum without having given her multiple orgasms.

I have also instructed Alyssa, her email read, not to allow you to cum without her feet in your face, which is something I want you to get used to. This is to show her that you are subject to her and that she is in charge in your sex life.

I shook a little at the finality and determination of her words, and I wrote back saying that I understood and I would do my best to promote the atmosphere and the conditions she was describing.

And I did get used to it. Alyssa worked hard and often brought her work home with her, but when we did find the time our sex was a devoted, almost ritual pursuit of her pleasure and empowerment. She expressed how much it was working, how well she was doing and how she was beginning to feel more in charge of herself and of more aspects of her life, and we talked a lot about that strength and that development. Marlena would check in with me from time to time, letting me know how pleased she was with Alyssa’s performance, and she would provide notes occasionally as she quizzed Alyssa at the office, sending us little tips and exercises to do.

“Facesit more,” I remember Alyssa reading from a memo, one she had been sent home with sealed in an envelope one night, which then went on to detail an elaborate process for doing just that and requiring that it be done in spare times both with and without oral sex.

And then finally, when the end of the quarter was approaching and their sales target was in sight, Marlena got even more serious.

She called us both into her office one night when they were working late, Alyssa summoning me to their building with a text message, and she actually had me get down on my knees while Alyssa stood next to me, and she sat behind her desk looking us over for a moment before lifting her legs and putting her feet on the desk in her black high heels, her stockings traveling all the way up to her exposed thighs. She reached for the hem of her stiff, professional dress and lifted it up to her hips, exposing her strapon and letting the hum of her vibrator be heard.

She spoke for a few moments about where they were in their strategy, and about the crunch that would get them there over the next week, leaning back in her chair and looking down her glasses at a folder she held in front of her, and then she set it aside and looked across at us again.

She pushed back from the desk and swiveled to face us, and then she slid her legs open and kept her heels on the edge, presenting her crotch and her firm, prominent strapon.

“Now,” she said. “This is the final push. This is the final test and it will require everything we’ve done up to this point and more. Alyssa, get down on your knees.”

My eyes pealed wide and I shuddered as Alyssa got down beside me, and we both looked up at Marlena. “Crawl towards me, at the edge of the desk.”

She looked down for a moment before she spoke.

“I’m instituting a zero penetration policy for the remainder of this agenda, effective immediately.”

Alyssa gasped subtly, but audibly enough that Marlena raised her voice as she continued.

“You will refrain from vaginal or anal penetration until our goal is met, and this will be enforced by me through the use of a locking device to which I will hold the key.” She reached into her desk drawer and produced it, a metal chastity cage with bars and a tiny lock. “You will still be entitled to your daily allowance of oral service and you may orgasm clitorally as often as you please, but there is to be no interior stimulation of any kind.

“When you achieve what you set out to achieve before we started any of this, I will return the key to you.”

I trembled, and so did Alyssa, and then Marlena looked at her and spoke again.

“If you agree, kiss my foot.” She kicked off her left shoe and set her heel on the desk, presenting it to Alyssa and looking down expectantly.

“And you,” she said, kicking off her other shoe as I watched Alyssa’s head bow forward and heard the sound of her kiss. “Crawl forward and do the same.”

She sent us home with the chastity cage that night along with another set of instructions about placing it on. It involved more little ritual, and she demanded to be sent videos proving we had done as she said.

“It’s just for a little while,” Alyssa whispered as she put me into the cage. “You’ll still be able to please and worship me. And when I make partner it’ll all be worth it.”

Marlena made us start a group chat over text and said Alyssa was to report every time she was horny for penetration. It was nearly every day now that she said, several times a day, how hungry she was, and every time Marlena would respond with strict discipline and motivation, giving status updates and progress reports. She’d sometimes send Alyssa videos of her fucking herself with her own dildo, just to remind her how good it was. And she wore both of the keys to my cage on a chain around her neck.

Finally, the home stretch was coming up, and Alyssa kissed me on the cheek as she left for the morning. “We’re getting close,” she said. “I can feel it.” She reached down and patted my locked package, tucked away in my underwear. I could still smell her on my face after her morning service, and I felt so swollen and full of cum.

I was flustered and swollen on a regular basis now, I was used to that to the extent I could be, but now that I had actually acclimated to some degree relief and release seemed like even more of a challenge than the chastity. Not unwelcome, just unnerving, particularly because I didn’t know what it meant they were going to do to me once they let me out.

And then, somehow, even before she texted me that day I felt I knew. I knew she had done it, and I knew it was all beginning to happen. It was time.

* * *

My heart pounded as I stood before them, and both Alyssa and Marlena seemed proud and delighted in their accomplishment. They smiled knowingly to each other, sharing something powerful, and then they rose together and Alyssa went and sat on the desk.

She beamed at me as I turned around, and Marlena went behind her and felt in the desk drawer for something. She came back around and sat beside Alyssa, and took a deep breath before presenting her with a black velvet jewelry box, and she smiled as Alyssa’s face lit up.

“This is for you,” she said, sitting down beside her and ordering me down to the floor in front of them, opening the lid and looking down at what she had gotten her.

Alyssa blushed and sighed, clearly overcome with emotion as she looked down, and she pulled out the tiny paper card. “The keys to the castle…,” she read, and she teared up and leaned over to kiss Marlena before pulling it out.

It was a short, bright silver chain with a pendant heart, and attached were both of the keys to my cage.

She clutched it and smiled, looking tearfully at Marlena, and then so appreciatively down at me. She looked me over for a moment, and then asked her, “Will you help me put it on?”

She slipped off her ankle boots and I heard them fall to the floor, and then she presented her ankle into Marlena’s lap. She had taken to wearing black thigh high stockings, like Marlena did, even when she was dressed more casually, in jeans and a blouse on days when they didn’t have any meetings, and the soft silkiness of them brushed gently against Marlena’s thigh.

“Wait,” she said, leaning forward as Marlena reached down.

She reached for the chain, and she took off one of the keys and handed it back to her. Marlena fastened the chain around Alyssa’s ankle, and Alyssa looked down and admired it, rolling her ankle in Marlena’s lap before holding it out towards me and dangling it in front of me, shaking it around.

She pulled her leg back and reached up for Marlena’s neck, the necklace she had been wearing all this time. She opened it up and returned the key to its place, and held it up, open, to offer it to her.

Marlena smiled and lifted her hair, and as Alyssa clasped it in place she kissed her again, more deeply this time. “Partners,” she whispered, and she smiled widely at Marlena.

Marlena grinned and they kissed again, and then they both looked down at me.

“I didn’t say I would let you out when this time came,” Alyssa said, her voice suddenly possessed of volume and authority.

“Yes,” Marlena echoed, “And I only said she would have the power. It’s hers what she chooses to do with it.”

“You’re going to have to earn that, even if you’ve been such a good boy until now.”

“This moment is your reward,” Marlena said grandly, “and you should be proud of your goddess, and grateful.”

“Yes ma’am,” I responded reflexively, even as shocked and as devastated as I was by having my chastity prolonged.

They stood up and went around behind the desk together, and Alyssa stripped off her jeans. She was wearing black, lacy panties along with her stockings, and she unbuttoned her blouse to reveal her incredible breasts in their matching bra.

Marlena pulled off her tight, professional dress and stepped out of it, wearing panties like Alyssa’s but nothing else, apart from her stockings and heels. My heart pounded as I saw her bare breasts emerge, and she turned back to the drawers and pulled out her harness.

Her dong was already attached to it, and she pulled it on and stood up proud in front of Alyssa, her shoulders back and her hands on her hips. She let Alyssa marvel at her and drink in her raw sexual power, and then she reached back into the drawer and pulled out another harness and dong that matched hers perfectly, and she smiled again as she handed it to Alyssa.

You could see now that Alyssa really did want to cry. She took it in her hands and held it gingerly, and Marlena reached down and put a finger under her chin. “Put it on,” she said as Alyssa gazed up into her eyes. “Panties off.”

Alyssa looked back at me as she pulled off her panties, revealing that glorious cunt I had been enslaved by, and she knelt down and stepped into the harness. She sighed audibly as she pulled it up against her thighs, and Marlena reached down to help her adjust the straps and make sure it was fit properly. Alyssa put her hands on her hips and raised her chin, and for the first time I saw her so possessed of her full strength and power, so beautifully and abundantly confident, and she and Marlena shared a relieved, celebratory laugh together.

“Bend over the desk,” Marlena said softly, putting her hand on Alyssa’s shoulder. “I want to show you how good this new power feels.”

The desk creaked slightly as Alyssa pressed her stomach against it and she raised her head high before lowering her chest down to the desktop, and placing her hands alongside her. I knew how wet her pussy must be, how wet it had been getting every time we had done anything over the last couple of weeks, and how hungry she was for a fucking. I thought about all of the texts she had sent, at all times of day, moaning to be filled and saying how desperate she was.

Marlena’s discipline had softened now, and she caressed Alyssa’s back and arms, and gently touched down her backside before grabbing handfuls of her ass, and stepping forward behind her.

She reached down and grabbed for her cock, and she lifted it up to press against Alyssa’s crotch. Alyssa whined gently and I heard Marlena whisper as she leaned forward. “This is the power that you have now. This is what it feels like.”

She leaned back and tensed up her arm, and then I watched Alyssa gasp as she pressed and then pushed herself inside of her.

Alyssa let out a long, screaming moan, and Marlena fucked her deep and hard, grabbing for her hips and pulling on her body. I saw Alyssa’s toes reach down for the floor and stand up to press against her, taking Marlena’s cock as she thrusted deep inside her. She gasped and clutched and splayed her palms against the desktop, and then finally she lifted her head and started grunting.

“Cum,” Marlena said, thrusting. “Cum pretty girl. You deserve it.”

Alyssa let out a shrieking, groaning shout, one that traveled deep into her chest as she was pushed over the edge, and she came. Marlena fucked her all the way through her orgasm, grasping at her and guiding her back and forth slowly on her cock.

“Mmm, good girl,” she said, pulling out and letting Alyssa pant and breathe.

When she stood up she threw her shoulders back proudly and her cock hung in her harness, and it shook with her as she breathed, in and out. Her whole face was alive and I could feel her feeling the weight of it as she squared up her hips, her perfect breasts hanging proudly from her chest.

She took a few deep breaths and smiled her incredible smile again, but this time she looked at Marlena differently, as if understanding something she had wished so much for before.

“How does it feel?” Marlena asked sultrily, and Alyssa just stood there for a moment, breathing and sighing in response.

“Him next,” she panted, finally. “I want to do to him what you just did to me while you shove my cum down his throat.”

© 2019

This story appears in

HARSH: The Collected FemDom Erotica, Vol. 2.