Opening my eyes, I focus on the blades of the unfamiliar ceiling fan slowly circulating above the bed. 

To my left, sound asleep, is the wealthiest heiress on the Upper East Side. Just beyond her, on the nightstand, is an envelope full of cash. 

To my right, resting on the ledge of an easel, is the real reason I am here.

Trish’s words echo in my head. Not sex work. Art.

I take a long, hard look at a painting. Or should I say, what's left of a painting.

Trish’s words return, crisp and matter-of-fact. Sit back and watch a woman create a self-portrait. Satisfy… No… Fuck the woman. And then blow your load on the painting.

Perhaps I should start at the beginning.

Three weeks earlier…

“I’m close! Where?”

“Mouth!”

I pulled out and shifted around her, one knee beside her shoulder, my hand already working my cock.

It didn’t take long.

The first three bursts landed in Trish’s mouth.

Thinking I was finished, she closed her mouth and swallowed. 

“Wait. Not done!” 

Before she could react, another burst caught her across the forehead. 

“Fuck, so much…” she gasped, eyes squeezed shut as a trail ran down her face.

“I’ve got more,” I said, still stroking.

“More, more. Paint my tits!”

I aimed lower. Thick streaks landed across her neck and chest.

I dropped onto the bed next to her. Trish rolled on her side to face me.

“Holy shit,” she said. “I’ve never seen anyone cum that much.” 

She wiped a finger across her chin and licked it clean. Studying the mess, she exclaimed, “Jesus. How is this even possible?”

“What can I say? I’ve always been an overachiever." 

“Fitting.”

“Paint my tits? Where’d that come from?” 

Trish grinned as her fingers traced lazy circles around her nipples. “You don’t watch much porn, do you?”

When I didn’t answer, her smile faded. “Hey, I have an idea.”

“Do I even want to know?” 

“How long before you can do that again?” 

“Half hour. Maybe forty-five minutes.”

“That much cum?”

“I’m a unicorn, Trish. But even unicorns have limits.”

“Tomorrow, then?” She leaned forward. “Could you do that again tomorrow?”

“Tomorrow? Yeah, sure.”

Springing from the bed, she motioned towards the front door. “Then we’re done. Off with you!”

I pushed myself upright.

“Go home, get some rest. Drink lots of fluids. Do fluids help? Never mind. Just make sure you can give me a repeat performance!”

”Okay, tomorrow night. Eight?” 

“Perfect!” She disappeared into the bathroom and closed the door.

I took the hint and gathered my clothes.

Through the bathroom door, Trish called after me.

“Tomorrow, stud.”

The next day…

“Come in. I’m back here.”

I followed her voice through the apartment. Trish stood naked in front of an easel, brush in hand.  

“What’s going on?”

“Community education,” she said. “I took an oil painting class last winter.”

I looked from Trish to the painting.

“Fun fact: people fucking love art. And the stranger it is, the more they love it”

“I’m not following.”

“Take off your clothes and get comfortable. I’ll be done in a few minutes.”

I didn’t move.

She glanced over her shoulder. “When I’m finished, I’m going to fuck you senseless. Then, when you’re ready, you’re going to cum all over the painting.”

“Your self-portrait?” 

“Yes. Oil takes forever to dry. I want to see what happens. Pretend it’s my face.”

I took my time undressing and settled onto the bed before propping myself up on one elbow. 

“You’re talented, Trish. Are you sure you want me to ruin it?” 

“Trust me. The painting can take it.” 

She set down her brush and palette. A moment later, she crawled on top of me. She kissed me and pushed me back against the mattress, working her way down my chest. Her hand closed around me and my cock responded immediately.

“Good boy,” she mumbled as she took me in her mouth. 

She tightened her grip on my hips. I slid my hand through her hair and guided myself deeper. 

She gagged.

I eased my grip and let her breathe.

“Don’t stop,” she managed.

I took her head in both hands. Then I pushed deeper. 

She took me without hesitation. 

After a few minutes, Trish pulled back. She wiped the corner of her mouth with the back of her hand and grinned. “You like this?”

I pushed myself up on my elbows for a better look.

“Yeah.”

“Good. Because we’re just getting started.”

She smiled.

“Perhaps I should’ve mentioned that art makes me super fucking horny.”

Without another word, she lunged at me. She wrapped an arm around my waist and drove me back onto the mattress. 

She turned to face the foot of the bed and swung a leg over me. Then she reached down, took me in her hand, and lowered herself onto me.

Her head fell back.

“Yes!”

Then she started fucking me. 

The first time we had sex was good. Better than good. Tonight, Trish was insatiable. 

I had never had a woman fuck me like this. 

Ever. 

One position gave way to another. 

Then another. 

Trish came at least three times. Maybe four. 

Eventually, I felt myself getting close.

“Fuck, Trish. I’m close.”

Trish stopped and lifted herself off me. She grabbed my hand and pulled me off the bed. 

“What the fuck?” 

“Trust me.”

She led me to the easel and positioned me in front of the painting. Then she stepped behind me.

Reaching around me, she took me in her hand.

“How’s this?” she asked. “Faster?”

Trish’s naked body pressed against my back. Her painted face stared at me from the easel.

“Yeah,” I managed. “Faster. Spit in your hand.”

She did as I asked.

“Tell me when,” she said. “I’ll aim.” 

*****

“It’s beautiful,” Trish whispered.

I stepped back and wiped the sweat from my face.

Trish stood beside the easel with a proud smile. “What do you think?”

“I feel like I just ruined something beautiful.”

The portrait was still recognizable. White canvas showed through where the wet paint had broken apart. Below it, oil and semen slowly crept down Trish’s painted face. As it turned out, the two did not mix.

Trish’s smile grew as she studied it. “I think it’s perfect!”

Six days later…

Over the next few days, I learned a lot about Trish.

She had grown up on the Upper East Side. And she was connected to a corner of society with too much money and very eclectic tastes.

Another marathon session ended with me defacing the fourth portrait that week.

“I think we can sell this,” Trish said.

“You are going to sell your paintings?” I asked.

“No, we are going to sell an experience.” 

“Excuse me?” 

“It’ll be easy. I’ll help our client with the painting. That’s where you come in. All you need to do is sit back and watch a woman create a self-portrait. Then you’ll satisfy… no.  You’ll fuck the woman. And then blow your load on the painting.”

“How much?” I asked.

“How much?”

“You said ‘sell’. How much will this cost a prospective client?”

“Excellent question. They’ve got deep pockets. A few thousand, maybe. It might even vary based on…”

Trish looked at me and laughed. “I see where you are going, Dan. This isn’t sex work. This is about creating art. The sex… that’s just a bonus.”

“And where will you be while I’m… creating art?”

“Maybe I’ll record the session.”

I stared at her.

She laughed.

“Kidding, Dan. Part of this is about the sex. And yes, this is also about art. But it’s also about discretion. I’ll probably excuse myself and hit the coffee shop across the street.”

I rolled my eyes. “Okay. Who’s our first client?”

*****

“Are you fucking kidding? And she’ll be here in two hours? But we just fucked. Don’t you want me — how did you put it the other day? — well rested and hydrated?”

“After your first performance, I didn’t know what I didn’t know. Since then, we’ve fucked, what, nine, maybe ten times over four days. And we’ve ruined four paintings. You’ll be fine.”

“How do you even know her?” I asked.

“She’s a friend from high school. Like me, she’s from new money. Unlike me, she followed her parents’ plan and married old money. She confided in me a few months ago that she’s tired of vanilla sex with her ‘prim and proper’ husband. She’s paying for both the experience and the confidentiality…”

“Feels like sex work, Trish.”

“... and the art, Dan. The art,” she said with a wink, as she disappeared into the bathroom. 

“Speaking of, we need to get the apartment set up. Wanna join me in the shower first?”

*****

The door opened, and a gorgeous woman entered the apartment. 

She walked past me and handed Trish an envelope.

“Cash, as requested. How exactly does this work?”

“Dan, this is Erin. Erin, Dan,” Trish said with a warm grin. “Follow me, we’re gonna start in here.”

Trish led Erin into the bedroom, and I hung back.

Two hours later, I joined them.

Seeing me enter, Trish motioned to a plush chair in the corner. “Have a seat, Dan. We’ll be done in a little while.”

I settled in and watched as Trish guided Erin through her self-portrait.

After another twenty minutes, Erin handed the palette and her brush to Trish. She unzipped her dress and let it fall to the floor. Turning to me, she gave me a predatory smile. “Good enough. Can we fuck now?”

Trish started collecting the art supplies. “You know what to do, Dan. Give me a minute, and I’ll be out of your hair.”

“You going somewhere?” Erin asked.

“I was going to go grab some coffee, give you some space. Dan’s got this from here.”

Erin unclipped her bra and flung it to the side. Then she crawled onto the bed, wearing only thin lace panties and four-inch heels. She reached down, unbuttoned my board shorts, and started stroking me.

“Oh, yeah, he’s got this,” she said with a smile. “But Trish, wait. Sit. Watch.”

Trish paused in the doorway. “Watch?”

“I’ve always wanted to have someone watch me fuck. And I’m your first client, right? Consider it quality assurance.”

Erin motioned for me to get to my feet. She took hold of my cock and led me to the bed. 

Then she looked at Trish. “Sit, please.”

As we crossed the room, gravity pulled my shorts and boxers down. I easily stepped out of them. 

Erin dropped to her knees beside the bed and took me in her mouth. Then she pulled back. Looking me in the eyes, she smiled.

“Haven’t sucked cock in God knows how long. You have no idea how much I’ve been looking forward to this.”

Erin proceeded to give me one of the best blowjobs I’ve ever had.

While she took my cock in her throat, I glanced at Trish. Erin noticed and stopped. “Wait a second. Are you two a couple?” 

I honestly didn’t know how to answer that. I’d known Trish for less than a week. What I’d assumed would be a one-night stand had evolved into something else. Granted, we had been fucking like rabbits for a few days now. 

“Business partners with benefits,” Trish answered without missing a beat.

“Fair,” Erin said before turning back to me. “Okay, big boy. Time to fuck me in front of your business partner. And I want it rough. For the next hour, treat me like a fucking whore.”

I pulled my shirt over my head and tossed it across the room. Then I pulled Erin to her feet and pushed her onto the freshly made bed.

Crawling between her legs, I slid her panties to the side and took her clit between my lips. 

“Oh, yeah. Fuck,” Erin moaned. 

I slipped a finger inside her while I circled her clit with my tongue. I added a second finger. Then a third. And then I took her clit in my mouth.

Suddenly, she clamped down around my fingers as she flooded my mouth. “Oh, my God!” she gasped. “Fuck. I’ve never squirted before.”

She held my head in place, her body trembling. 

When Erin stopped shaking, I pushed myself to my knees. I reached down, rolled her over, and positioned her onto her knees. I took a handful of hair, mounted her, and started fucking her. Hard. 

“So. Fucking. Good!” she screamed. “More!”

We didn’t stay in one position for long. As we fucked, she begged me to pull her hair, choke her, and slap her ass hard enough to leave handprints.

After she’d cum several times, I realized I was close too. 

I pulled back.

She collapsed onto the bed and looked across the room. “Get your hands out of your shorts and come over here, Trish.”

It was only then that I realized that Trish had been masturbating in the corner.

“Finish him off. I want to watch from here.”

Trish got to her feet and adjusted her shorts. Nodding to the painting, she held out her hand. 

I slid off the bed and let her lead me across the room.

Shifting me so that Erin had a clear view, she spat in her hand and started jerking me off.

It didn’t take long. 

After I came, I returned to the bed and stretched out next to Erin. “Bring it over here, Trish. I want to get a closer look.”

Trish retrieved the painting. 

Erin looked at it for a long moment. 

Several small bursts dotted the portrait’s cheek and jaw, each one settling onto the uncured paint with only enough force to dimple its glossy surface. Pale beads gathered in separate clusters, some holding their shape, others beginning to sag and draw faint threads of color downward. Erin’s face remained recognizable beneath the scattered marks.

“I love it! Worth every fucking penny.”

Yesterday morning…

Over the next two weeks, Trish and I entertained around a dozen clients. But the experience itself had evolved. 

Some women wanted traditional self-portraits. 

Others opted for nude self-portraits. 

Others cared more about getting fucked rather than the art. They still left with a ruined painting. 

Most of the time, Trish slipped out once the painting was finished. 

A second woman wanted Trish to stay and watch. 

And another surprised us when she asked Trish to join us. Trish surprised all of us that evening, including herself.

Trish walked into the bedroom with a steaming cup of coffee. “Rise and shine, stud,” she said with a grin. 

I rolled over and accepted the coffee. Then I pushed myself up against the pillows.

Trish crawled into bed and cuddled up beside me.

“Who knew that art could be so profitable?” 

We were making several thousand dollars every session. I was seriously considering quitting my full-time job. 

“Tonight, we’ve got someone special.”

“Special?”

She casually dropped the client’s name. 

I laughed.

She wasn’t joking.

Tonight’s client was one of the biggest names in the city. 

Maybe the world.  

“A few changes tonight,” Trish explained. “First, we are going to her. You’ll need to follow a very specific security protocol to ensure we are as discreet as possible. Second, I will definitely not be there. I will go earlier and help her with the painting. But when you arrive, I will be long gone. Oh, and plan on spending the night.”

Then she dropped the bombshell: The client was paying four times our normal rate. Twenty grand. 

Before I could respond, Trish took the coffee from my hands and set it on the nightstand.

Then she leaned in and kissed me.

 “Enough talking. Fuck me, Dan.”

Yesterday evening…

Linda greeted me at the doorway to her penthouse wearing only a black silk robe. 

She welcomed me inside and led me up a circular staircase, which led to a large bedroom with a panoramic view of the city. 

Linda was unlike any of our previous clients. 

The first thing I noticed was the age difference.

All of our previous clients were around the same age as Trish. Late twenties to early thirties. Linda was older. Maybe early sixties. 

But despite being older, Linda was one of the most beautiful women I’d ever met. And under that beauty, there was something else. Something familiar. Something I just couldn’t put my finger on.

Linda paused next to the recently completed self-portrait. “What do you think?” 

“I think you’ve painted before.”

“Lots of free time, too much money,” she said as she made her way to a massive bed on the far side of the room.

She paused to remove the robe, revealing the most exquisite lingerie I’ve ever seen. She then crawled into the bed and turned to find me gawking at her. 

“Everything okay, Dan?” Linda asked.

I nodded.

“Good. Take your clothes off.”

I took my time undressing.

When I looked back towards Linda, she licked her lips and held up her index finger. Curling it towards herself, she purred, “Trish was right. You are spectacular. Now, come over here.”

Joining her on the bed, I crawled towards her and let myself hover over her, our faces inches apart. 

Most of our clients insisted on not kissing. Linda had other ideas. 

I felt her hand run through my hair as our lips touched and her tongue made its way into my mouth. 

For several minutes, we shared a deep, passionate kiss.

As if reading my mind, Linda pulled back and looked deep into my eyes. “Are we going to kiss all night? Or are we going to fuck?”

I rolled onto my side. Her fingertips traced an invisible line down my stomach before she took me in her hand and started stroking my cock.

I traced my hands along the curves of her full breasts through her bra. Reaching behind her, I unclipped the clasp and eased the bra over her shoulders, revealing her perfect tits.

Cupping one, I brought my mouth to her nipple. It was already hard. I took it between my teeth, playfully biting down and teasing it with my tongue.

While I suckled and pinched her nipples, I let my other hand follow the intricate lines of the lingerie.

As I made my way between her thighs, she willingly spread her legs, revealing sheer panties already moist with arousal. 

I drifted down between her legs. Hooking my fingers in the sides of her panties, I eased them down.

I buried my face between her thighs, breathing in her scent and letting my gaze linger for a moment. Then I extended my tongue and tasted her. 

The contact made Linda shiver.

“Oh, God! I appreciate a man who isn’t afraid to use his mouth…” she moaned, her head falling back.

A few minutes later, I felt Linda’s thighs tighten around my head as she screamed my name. 

Still breathing hard, she managed, “Fuck me. Now.”

Repositioning myself, I spread her legs wider and entered her. I quickly settled into a slow rhythm, watching her body move beneath me.

I slowed down when I noticed something in Linda’s expression.

Without asking, I leaned in and kissed her. For a moment, I was lost in the kiss. It wasn’t necessarily about Linda. There was something else. 

Then, Linda wrapped an arm around my waist and drove me back onto the mattress. Just like Trish.

And just like Trish, Linda swung a leg over me. Then she reached down, took me in her hand, and lowered herself onto me.

For a moment, I just stared. Déjà fucking vu. Then I stopped thinking and watched Linda ride me.

A few minutes later, she settled hard onto me and her whole body tensed. 

I held her through it. 

When she was done, she looked back over her shoulder. “Wow, that was fucking amazing. But I think we still have a painting that needs to be defaced.”

Sliding off me, she pushed herself off the bed. She then reached out, took my hand, and helped me to my feet.

“How about a quick blowjob?” she asked, with a wicked grin as we approached the easel.

I don’t know if it was years of experience, a technique she learned from a former lover, or something else, but the things that Linda could do with her mouth were unlike anything I’d experienced. It only took a few minutes. I told her I was close. 

Getting to her feet, she took me in her hand and started stroking. 

When I started cumming, Linda’s eyes lit up. “Holy shit! Trish said you came a lot, but… Wow. I’ve never seen anything like this!”

When I was done, she stepped back to observe the self-portrait. She didn’t say anything. She didn’t have to. Her smile told me everything I needed to know.

Linda turned toward the bed and took my hand. “I have one rule that Trish may have neglected to tell you. I always insist that all of my lovers spend the night. And that’s not up for debate.”

Then she led me back to the bed.

Now… 

I feel Linda stir next to me. She drapes an arm across my waist and I feel her hot breath warm the back of my neck.

“I’m sure you get this all the time, but that was really fucking good.”

Pushing herself off me, she slips out of bed and reaches for a robe. She crosses the room and stops in front of the painting.

She stares at it for a moment and then motions for me to join her.

I come up behind her and wrap my arms around her waist. After last night, it just feels right. 

The impact had cratered the wet paint. Surrounding the initial impact, cum and oil had marbled together, yielding to gravity and forming tiny comets that streaked across Linda’s once-beautiful face and neck.

“Trish was right, as always. It’s stunning.” 

I shrug and rest my chin against the back of her neck.

Linda turns and gives me a knowing smile. “Last night was amazing. But we should probably wrap this up. As much as I’d love to go another round, something became clear to me yesterday when we were making love.”

I raise an eyebrow.

“When most guys fuck me, they don’t pause to kiss me. It was almost like you saw something in me. Someone in me.”

I have no idea where she was going with this.

“Don’t play coy with me, Dan. I know you two tell everyone you’re just business partners. But in that moment, it became obvious that you are in love with my daughter.”

I am speechless. 

“I’ve had a lot of lovers over the years. And I know when the man I am fucking is in love with another woman. I’ll admit, though, realizing in that moment that the other woman is my daughter, that was a first.”

“Your daughter?”

“You didn’t know?”

“No.”

“That Trish is my daughter, that you are in love with her, or that she has feelings for you?”

Again, I am speechless.

Linda shakes her head. “I should have realized it earlier. When I first heard about this, I expressed interest. Art? Sex? What I missed was that she hesitated. Trish never hesitates. That’s her tell.”

“What?”

“Trish is in love with you, Dan.”

“I… I had no idea.”

“Well, now you do. Don’t fuck this up, Dan.”

She kisses me on the cheek. Then she smiles.

“But this…”

“Last night was fun, Dan. And this little thing you two are selling? It’s cute. But do me a favor. I’ve never seen Trish this happy. Do not break her heart.”

I swallow hard.

“Oh, and don’t forget to take the money. As I suggested, the experience was absolutely worth it.”

With that, Linda leaves the room and I am left standing naked in front of what might be the last piece of art I’ll ever be paid to ruin. 

Closing my eyes, I smile.

Trish.