You weren’t sure that you were living your dream. You thought that getting your MFA would mean that you’d be up late selling your art at parties to absurdly rich clients. You thought you would be dating your future husband. You thought you might be living in the countryside, maybe in Colorado, just a short drive from Denver.
Instead, you were stuck in Chicago as Gwenn’s personal assistant. Not only had you gone against your better judgement in taking the job with Gwenn, but your father insisted that he came to the United States so that you could become more successful in life. You supposed this was a start. You were still able to paint and sculpt some nights and weekends. Maybe you’d sell a piece to Gwenn one day, like that French asshole, Louis, had, but, until then, your workdays consisted of being Gwenn’s personal assistant.
That wasn’t what you expected, but that was the reality.
Gwenn was wealthy, and didn’t have any children. She confided in you once that she wasn’t sure that she’d ever get married. That said, she didn’t exactly have the time to date normally. But, she still had needs.
In addition to you setting up her dinner dates and setting up other activities for her, you also sometimes accompanied her to playdates or movie nights. You were never in the room with her and her playdate. If the playdate was at her condo, you kept to yourself in the kitchen and living room – except for that one time with Randall when she wanted to fuck him on the new couch. You made yourself scarce by hiding in the bathroom until he left and she was dressed.
Randall had always been her favorite. There were a handful of other men you’d set her up with from time-to-time. She appreciated the variety. Her recent interest, however, was Louis.
They first met, and first fucked when she met him in Nice while on vacation. They first met four years ago at a nude beach where she noticed his athletic figure… and massive cock. Louis is a struggling French artist. After first hooking up in his loft, she purchased three of his paintings for far too much money. He has sold some paintings since then, but is in a bit of a rough patch and has hoped for a meeting with Gwenn to sell her new works. Gwenn, however, is only interested in him sexually. Once, when she was drunk, she admitted to you that she would never let him fuck her in the ass – something that you knew she only reserved for Randall, but she “loved how completely full her pussy felt on his cock.”
Then, after constantly trying to get on her calendar, he managed to sell another painting to another client. He bought plane tickets to Chicago, and told you to let her know that he had relocated to the city.
You were always jealous of Louis. He was an artist, and you hadn’t sold a painting, sculpture, or anything. He was stealing lots of her time from Randall, who you always liked for her as a potential romantic match – even if you knew he cheated on his last wife with Gwenn, and others. But you also noticed that you were feeling jealous of him sexually.
It started with a small sex toy in a novelty cup for Valentine’s Day – which you had to sign for at Gwenn’s office, which led to several dozen encounters between Louis and Gwenn throughout February and March. In April, it seemed that she was done fucking Randall. And then, she took Louis for three days straight. She wasn’t even trying to be modest with him. She left her curtains open. She frequently didn’t wait for you to leave her apartment before they were half-naked – and sometimes further.
It angered you. It made you jealous. You either bottled those emotions up or expressed them in your art. But, sometimes… you’d find yourself masturbating yourself to sleep thinking about the things she told you he had done to her, or the things you’d seen. You just couldn’t fucking stand Louis though. The next time she wanted a playdate booked, you’d decided it would be with Randall. It didn’t matter that Gwenn was more enamored with Louis’ butt-plug gift for Valentine’s than Randall’s dozen bouquets. Her next fuck needed to be Randall. The next several fucks needed to be Randall, really.
The jealousy that began boiling over and starting to boil out in your artwork now gave way to nothing but resentment toward the man who took up so much of Gwenn’s time. You also found your fantasies coming out onto the canvas as well. You would think about how she surely must have felt about Randall, to have been carrying on with him for as long as she had. When you thought about that, you’d paint figures of women feeling joy, even love. Then, you’d think about Louis, and you’d paint over-sexualized women – or even just their anatomy – ruined by an undeserving man. You once painted an entire canvas that had nothing on it but a thoroughly destroyed vagina, bruised and coated in undeserving cum.
All the while you painted, tears flowed down your face.
What were you feeling for her? In all this time booking fucks for her with Louis and Randall and everyone else, your own dating life had ground to a halt. You hadn’t even been on Tinder in… you couldn’t remember since. Were you developing an attraction to her? Were you feeling threatened, or envious, of Louis?
One night, in the middle of a painting session, something more abstract – maybe about your absent thoughts of your own dating – Gwenn sent you a message asking if she could use your business credit card from her account. Her card had been damaged in a card reader, and the replacement would arrive in 2-3 days. You told her that you could get it to her, but you didn’t expect her to knock on the door a few minutes later.
“Can I come in?” She asked. You nodded demurely and let her inside.
You were so unprepared, coated in splashes of paint, still in your overalls and a t-shirt. Worse yet, the canvases you meant to hide before she arrived were still all out, all over your apartment. You just knew she would glance over them and recognize the similarities between her own figure and the figures in the paintings. You hoped she’d just say nothing.
To your shock, and agitation, Louis walked in behind her.
His eyes lit up at the sight of all the canvases, all your work. “May I…” he motioned with his hand, “…look around.” You couldn’t bring yourself to say no. The fucking artist just had to stop and analyze every painting he saw. Worse, Gwenn followed him around and listened to his musings about your work.
“I’m amazed,” he said. “These are incredible.” You blushed, caught off guard for a moment. “It’s like she knows how to really capture the essence of what a woman is feeling or experiencing in the paint.” He spoke slowly and with reverence. “She feels something so strongly for her muse.”
Your own sense of being exposed heightened when he suggested your subject was happy, which only intensified the surge of guilt you experienced when you realized that Gwenn was not looking at the paintings as much as he was. She was looking at you. Your muse figured out what she was.
***
The next day was nerve-wracking. Every part of you felt tense as you walked into the office. Gwenn hadn’t said anything about what she’d figured out. She hadn’t confronted you about your feelings. Her and Louis had just left your apartment with the credit card she wanted in the first place. Besides, you hadn’t been doing a great job gate-keeping with her evenings if Louis was monopolizing her time.
Then your phone went off. Randall had sent a message asking for time on Gwenn’s social calendar for that evening. This was your chance. You agreed and booked him for that night after work. You even sent him a message, which you asked him to keep private, “She’s hoping for something special, Randall. She really needs it.”
Then she walked in. She walked straight to your desk. Every part of you felt tight and exposed. She asked you, knowingly, “So, I am your muse?” She didn’t even wait for you to reply. “I didn’t even know you painted,” she said. “But I like the work, and I am flattered.”
She sat across from you, crossed her legs, and neatly placed her hands on her knee. “So, what is my schedule like today?”
You covered the basics of her work schedule, a few calls with investors, and you let her know that you booked time for her to review some market conditions she’d asked you to gather reports on. Then came the discussion of that evening. Her dinner had been booked months in advance – just an investor meeting with a couple old Hollywood acquaintances. Then after dinner, “And Randall asked to be on your calendar, so I booked him for this evening.”
“Thank fuck,” she said. “Louis has been driving me a little mad. Always wanting me to buy more art.” She uncrossed her legs and spread them slightly, “And fuck he makes me so sore the next day.” She looked up at you, “Don’t get me wrong, I love it. A fuck and orgasms like that are a rare find, but sometimes it can be too much. I may only have a few dates with him left in me.”
How many exactly?” you asked, curiously.
She gave you a knowing look. “Two,” she said casually. “Or three. It depends.” Then she got to her feet. “Well, I better go make myself presentable.” She got up and started to walk off towards her office before turning back and asking, “Do you not like him?”
You hesitated. “I do not.”
“He picked up on that,” she replied. “Despite what he was saying at your apartment, he didn’t like your work.” She shrugged, “His opinion doesn’t really matter on that though. If I want to hang your art in my bedroom, he can just stare at it while he fucks me for all I care.”
Something inside you felt relieved to hear that your distaste for him wasn’t unfounded. You also felt relieved that he would be set aside for a while if Gwenn had her way… and, for as kinda as she was, she always got her way. You remembered what it was like the last time you made a mistake in her bookings. At least she apologized for how she reacted after that incident.
Maybe you didn’t hear the chime come in on your phone or something, but another mistake was about to happen. You wouldn’t find out until later that Louis had sent a “request” of his own. “Let Gwenn know I’ll be stopping by tonight. She isn’t answering my texts this morning. She’s probably busy.”
***
Dinner with her old friends and investors came and went well. You and her were off to her condo together to get the place ready for her playdate with Randall. It was your job to make sure that the place was clean and that any sort of other arrangements were taken care of before the playdate arrived. For example, if there was supposed to be wine, you needed to get the bottles and glasses ready, make sure that any food deliveries were set out and ready to go, and even make sure that the lighting was set how Gwenn wanted it.
After getting to her condo, you set about preparing the two bottles of wine, one red and one blush, and she went off to the bedroom to put on lingerie. She came back a few minutes later just as you finished setting the pillows up on the large six-seater couch.
The black lingerie was new and not something you would ever see her wear. The straps seemed to cross over her chest and reach behind her back where they connected to a decorative clasp. You could tell by the fabric that the bra itself did little to keep any secrets about her body. “Is this too slutty?” She asked. “I know this is not the sort of thing you’ve given your opinion on before, but, after seeing how you imagine me in your paintings, I feel like I can ask for your opinion. Is that okay?”
You nodded to say that it was okay for her to ask. Secretly, somewhere inside you, you always hoped she’d ask your opinion like this. You knew then that this was what you’d always wanted to see but never admitted to yourself. It would have meant nothing to you except that it now meant everything.
Her black lace panties were attached to matching thong by strings, very brief, almost to the point of being no underwear at all. You could hear men murmuring in the hallway outside her door, but it seemed so far away. All you could do was look at her. Sure, you’d experimented with your sorority sisters in college, but you’ve never wanted a woman more. You imagined kissing her lips, her tongue touching yours, your fingers on her skin, and her fingers sliding into you. You felt high, like you were floating in a sexual fantasy you’d never had before.
Then, the knock at the door deflated your dreams.
“Who is it?” Gwenn called from inside.
“It’s Lou…” You heard. You could hear muffled voices coming from the other side of the door. Voices? What was Louis doing here? You panicked and didn’t know where to go, so you ducked beside the large arm of the couch. Gwenn walked over and opened the door.
Louis barged in past Gwenn with something of a huff. Randall walked in, much more calmly, after him. You could see Gwenn’s eyes grow wide as you peeked over the arm of the couch. You knew that look. You’d never seen it with her nipples growing hard like she was cold before, but you knew what that face meant.
“You did not tell me that you were seeing other men,” Louis said to her. He wasn’t completely angry, more shocked. He had that look on his face that some men get when they think that they aren’t special. Or worse yet, when they think that someone else has stolen their thunder, done better than them.
“Lou, why don’t you go pour yourself a glass of wine and let me talk to Randall alone for a minute?” she asked him. Louis looked agitated, but he then nodded and stepped to the bar to grab the bottle.
“What are you all dressed up for?” she asked Randall. “You’re wearing my favorite suit of yours. And what’s in the bag?”
“Well, I didn’t know this was what your assistant meant by special,” he whispered glancing over to the artist, then back to her. He opened the red, shimmery bag enough her her to see inside. “It’s a couple bath bombs, massage oil, a robe, and incense,” he explained. “It’s been a while since I’ve had a devil’s threesome, and I’m down for one if it’s what you want, but I’m not really into him at all.” He shook his head. “I wouldn’t want to touch him or vice versa.”
“My assistant?” she asked loud enough for Louis, and you, to hear.
“Oui,” Louis spoke up, “I messaged saying that I was coming by tonight.” He shrugged and took a gulp of his wine. “She never said anything back.”
“Oh really? How interesting.” Gwenn said in a louder tone. She directed her attention towards where you were hiding on the other side of the couch. “Considering that her job is to ensure that my appointments, both professional…” she paused and turned to look at each of the men, “…and personal, are properly organized…” she paused again, running her fingers along Louis’ forearm and then down Randall’s tie, “…I think feedback is warranted.” By this point, both of the men had figured out that you were in the apartment with them and, approximately, where you were. “Don’t you agree, gentlemen?” she asked them.
They both nodded.
“Unless her intention was, in fact, to book a night that I’m sure to remember,” she said in a tone that was somewhat wistful, lusty, and inviting. It prompted you to slowing rise to your feet where you hid. She beckoned you over to her with her finger.
You nervously walked around the couch and slowly approached her.
You could swear you could smell Louis’ wine-breath as you stepped past him.
The look on Randall’s face was one you weren’t initially sure of, but, after a moment getting closer, you recognized it: it was his competitive look. His eyes, while he took a couple glances at you as you approached, he eyed Louis like an enemy to out-compete and Gwenn like territory he needed to conquer.
You had to admit, in that lingerie, she looked all-powerful, stronger than you’d ever painted her. In that moment, she seared herself into your carnal memory and took control of your desires for that evening.
You stood in front of her, starting to feel the wetness inside your panties and trying not to tremble. She looked at you and asked in a way that needed to be outside of the moment but did not tarnish it, “Do you want to stay tonight?”
Your eyes glanced to each of the men.
“No,” she said, “they won’t be touching you. And you won’t touch them.” A comforting, yet desirous look came over her face. “May I touch you?”
You nodded.
She stuck out her index finger and slowly ran it down the buttons of your blouse. “I didn’t ask for this kind of night…” she said, back in her commanding tone, “…but I am not about to turn it away.” Her finger ran over the lip at the top of your skirt. You tingled everywhere beneath your clothes. You could feel goosebumps all over you. Her finger ran down over your sex, down to the hem of the skirt, and then clawed around it. She lifted your skirt up with that finger, and you were frozen, hoping for what came next.
You could feel her hand slide between your thighs, along the underside of your panties, where you could practically feel yourself opening for her fingers – if only the fabric there wasn’t in the way.
“Gentlemen,” she said, gently teasing you, “walk to the couch. Remove your clothes along the way. Take a seat.”
She whispered to you as they did as she commanded. “You are going to watch me own them. That is your punishment.” Her caressing you felt like a timer winding down to an inevitable explosion, and she wasn’t even touching your clit. “You will undress, but you may not touch yourself. At any point. You may have wine, but you may only watch what I do to them. What they do to me. Is that understood.”
You nodded, breathing deeply.
“You will watch as Randall strokes his cock, while I suck Louis’.” Her fingers slid up from the sopping wet bottom of your panties to your clit.
“You will watch when Louis strokes his cock, while I suck Randall’s.” She pressed her fingers firmly and circled to your pleasure.
“You will watch as I slide this thong to the side and ride Louis.” Consistent circling, consistent building. “Then Randall.”
“You’ll watch as I bend over for Louis, revealing the plug I’m wearing – the plug you didn’t know about.” More caressing. She drew herself closer to you. “You’ll watch him fuck me while Randall is in my mouth.”
You were transfixed by her, falling into her powerful eyes like a prey giving into the jaws awaiting it.
“You’ll watch as they trade places.” Firmer circling. “Then I’ll peel my panties off, set Louis down, and take out the plug.” Firmer, consistent. “I’ll get on top of his cock, let it fill my pussy.” Her fingers quickened their pace. You lust intensified. The sensation building. “Randall gets my ass.”
Your breath quickened.
“Both of them.”
Your breath deepened.
“Inside me, at the same time.”
You could feel it coming.
“Maybe there will be more than one position.”
The verge of climax was fast approaching. Her fingers damn-near demanded it.
“Maybe they will both explode inside me. Louis in my cunt. Randall in my ass.”
Her fingers quickened. Your pussy was drenched. The cliff of cumming was in sight.
“You will paint it.”
And she took her hand away.
“Go take your seat. Get one with the best view you can.” Her commands halted the hope of that desired orgasm. “I’ll expect your painting when you feel like it’s done.” She grabbed your jaw and kissed you before you could catch your breath. Her lipstick lustfully smeared itself all around your lips.
“And don’t you accidentally double-book me again.”
That night, and all the other nights with Gwenn thereafter, were never what you expected.