Maddy Sheridan smiled down at me, as I knelt on the stone patio outside the ballroom and dabbed the wine from her skirt with my tie.

I worked fast, terrified someone would walk out the french doors and catch me there. I worked fast, I felt my face red with shame...but my erection was straining my black dress pants, and I couldn't tear my eyes from her knowing, pleased expression.

Her gray eyes dug into me, hooked me and kept me. I felt the moan grow in my throat but fought it. 

"Don't look at me, Tom, look at your work."

I immediately bent my head and stared hard at the spot of red wine on her gray skirt. Steel gray to match her eyes, I thought, and had to fight not to look back up at them. 

The moan did escape when she began to stroke my hair. I leaned in against her hand, but kept rubbing.

Maddy laughed. "That's a good boy, Tom," she crooned, and her fingernails grazed the nape of my neck.

I fought the feeling that came over me whenever Maddy focused her attention on me - she was the only woman who'd ever made me swoon like that - and leaned in to lick the spot where she had spilled the red wine. Where she had intentionally spilled the red wine, after summoning me out to the patio.

I lapped hard, and couldn't help but imagine it was her pussy my tongue was stroking, and not a thousand dollar dress. I moaned again, and her fingers pulled my hair hard away. I let her, and stayed on my knees, with my neck turned, while she examined the spot. 

"Good boy, Tom, you got it all." She let go of my hair. "Now go get yourself cleaned up before the clients begin to arrive."

I quickly stood. "Yes, Ma'am," I murmured, my voice thick with lust as I addressed her in the only way she permitted when we were alone, when no one else in the agency would see me slip into the total submission she asked of me, and that I eagerly gavce. She narrowed her eyes at me, smoky and angry gray eyes taking me in and measuring me in an instant... but her lips curled in something between a sneer and a satisfied smile.

"You've worked hard to pull off this year's charity ball, Tom. I knew I made the right choice when I hired both of you."

I smiled. "Thank you, Ma'am." 

She flicked her hands, and I turned and stepped inside the ballroom, edging past the posterboard elegantly lettered with 'Maddy Sheridan Charity Ball, 2009'.

I took stock of the bar, the decorations, the food servers.. all seemed to be in order. I looked over everything a second time, just as I saw the first limousine arrive through the main door across the ballroom.

Everything was perfect. I felt my cheeks warm, as I thought how pleased Maddy would be.

I'd just survived my first to years at the recently renamed Sheridan Agency, two years in an internship with a dozen other men and women. She'd fired all the women for incompetency and all the men for... well, any reason she could I suppose. I never did find out why she chose me, but I was so glad she did.

I had survived because I worked hard, and because I didn't give in and become a yes-man... well, I thought and smiled, not in public anyways. I was a damn good advertising writer and I'd proven it, generating hundreds of thousands of dollars for Maddy and the agency that now bore her name alone, after she'd successfully ousted all her partners in a hostile takeover just a few months ago.

At forty-five, Maddy was on top of the world. High profile clients lined up for her precious time, and not a week went by she didn't appear in the fashion an design magazines. Papparazi eagerly clicked shots of her male friends, wondering when husband number four would show up, and women around the world admired her for her business acumen, success...and probably for her beautiful body as much as her brain.

The world loved Maddy, and so did I... though I never said that, not even to her.

I also loved Beth, the only other intern to survive the internship. We both had small offices on the opposite ends of the top floor of the skyrise that Sheridan Agency owned. She was hard as nails, a viciously clever and merciless editor and a brilliant co-creator of advertising. Most of our female clients asked for Maddy and Beth, whereas most of our male clients asked for Maddy and me.

We were engaged, and I loved Beth with all my heart. Well, all except the one small part of my heart and body that Maddy had introduced me to: the submissive, aching-to-be-obedient part. Maddy had known I was fucking Beth before she'd informed me I was hers to do anything she wanted to.. even though so far her ...well, her ownership of me.... only extended to permitting me to clean cream cheese off her fingers the day she told me what the arrangement would be, kissing her shoes behind her office's closed door the day she hired me, and now, licking her thousand dollar designer dress clean of wine that she herself had spilled.

But every day there were the conversations.

As I hurried into the kitchen to make sure the meal prep was going well - Maddy wouldn't brook any imperfection in her clients' experience of the yearly charity ball that had become one of 'the' parties to attend in New York every year- I thought back to that first conversation.

"How do you like fucking our little Beth?" she had asked me, that fateful day she had struck and I had weakened and accepted her in my mind and heart, as she had known I would. Every day now I waited for her to ask more of me, beyond the sharp, witty, dirty of commanding words we'd share during our morning meetings or other chance encounters, but nothing further came of the unique relationship she had informed me we were in.

How did I like fucking Beth? As much when we were just fucking as I did now we'd bought a condo together and were engaged. A lot. Beth turned quiet and submissive once the tall wooden doors to our apartment near Central Park closed behind us at the end of every day. She wasn't a weakling, but she enjoyed giving in to me, and there was love and respect and surprise between us all the same.

I had asked her about that, the first time we'd fucked, in the file room at the office, working long past the time everyone else had left for the day. She'd wiggled her ass against me to get a file, and I'd politely backed up, even as my cock swelled in my pants. 

Beth growled and backed up again, grinding her ass into me. I'd acted without thinking, instinctively growling back and wrapping my fingers around her throat. She'd melted into me and sighed 'yessss'. Then electricity and power had flown through my body as I pushed her forward against a filing cabinet, pulled up her skirt, ripped her panties off, and fucked her as she cried softly and begged me to pound her harder.

I stood just inside the kitchen, nodding outwardly to convey that I was pleased with how things were proceeding, as the memories of that first hard fucking played inside my brain.

Then I remembered the second time Maddy had played with me, in one of our daily meetings, two weeks after I'd licked her finger clean of cream cheese, and she'd informed me I was her plaything in no uncertain terms.

"Excellent work, Tom. Get graphics to lose some of the whitespace in the cover image, and I'll sign off on this." I'd leaned back in my chair and smiled, pleased to have done good work. Everybody loved pleasing Maddy - she'd lavish praise when you did, and tear a strip off you so deep you'd bleed for a week when you didn't. Of course I had another reason to want to please her: the deep insecurity of my position, as an intern, and the deeper insecurity of having recently letting her make me into her toy... only to not hear another word about it for almost two weeks of daily meetings.

It was exactly two weeks to the day after I'd sucked her finger clean, I realized then, as I stood in the kitchen... Exactly two weeks after she'd asked me how I liked fucking Beth and ordered me to the executive bathroom to masturbate and leave the sounds of my orgasm on her voicemail, that she made her next overture to me.

As I sipped my coffee in the chair opposite hers in the little discussion nook of her office, with the cityscape of Manhattan stretched behind her like something out of a movie, she crossed her legs and smirked at me. It was the very unique expression she'd made as she'd told me how things would be between us, and I'd accepted. When I'd started calling her 'Ma'am'.

Wearing that smirk, she waited as my eyes roved over her strong, lightly tanned legs. When my eyes met hers again, the expression on her face called to that part of me we didn't ever discuss unless she initiated, and I blurted an apology. 

"Sorry, Ma'am," I said, using the expression she insisted I always use in private - and wish I used more and more every day, hoping for a reaction.

"Sorry for what, Tom?" she asked playfully, letting one high heel fall halfway off as she swayed her toes. It did things to her legs that I liked, and I fought my eyes back to her face. 

"Sorry for staring at your legs, Ma'am!" 

She laughed. "I made you, boy. I know how to move if I want to... stir you."

"Yes, Ma'am," I said, practically gasping. 

She laughed again. 

"I want you to go to Beth's office, right now. Call my private line, put the phone on speaker, on her desk, then bend her over and fuck her doggy style. Make sure her mouth is near the phone so I can hear."

I felt myself go red. I opened my mouth to protest, but her eyes narrowed and instead I stood, and left without another word.

She still played the recording of my girlfriend's meek gasps and 'thank you!'s every once in a while. But she'd never asked me to perform the same way and it drove me crazy with desire. 

Truth was, licking wine from her dress was enough to almost make me cum in my pants. 

I nodded to the chef and told him I approved of his plans, and left the kitchen. Thin strains of music were coming from the live band, a string quartet playing mood music quietly as the first of Maddy's clients lined up to hug her or kiss her cheek before mingling.

She asked a question of me from across the room and I nodded, assuring her there were no snags in the evening's events.

She turned back to her line of admirers, dismissing me from her thoughts, and I felt a moan of need build in my throat again.

The party was a success, as always. By the end of the night, which came after two in the morning, I'd gotten verbal assurances of contract renewals from three drunken millionaires, and Maddy had slyly held up seven fingers in response when I'd told her the good news.

I only wish Beth could have attended. I missed her like hell, but a client had asked for her on-site, out of town, for some last minute tweaks to an advertising campaign. 

Which meant, I thought, as I watched Maddy see off her last client across the room, maybe, just maybe...

I waited by the front doors of the ball room as the chubby owner of a sporting goods chain laughed, hugged Maddy again and teetered into his limo. She gave a half wave as the black car moved away, then turned and stared at me.

"Drive me home, boy," she whispered. 

"Yes, Ma'am," I said, after gulping down my shock... and pleasure.

- - -

I drove Maddy home to her country house that night. She lived in the middle of nowhere, forty minutes out in the country. I parked her Aston Martin in front of her garage, opened her door, and escorted her, arm over arm, up the stone walkway towards her hundred-and-fifty-year old stone home. 

"You did excellent work tonight, Tom," she said casually. "It's like I've always told you, attention to detail, every little detail, is what wins the client, and gets their business. But none of those hot sausage bits next time, save those for the ball park, will you?"

I laughed. "Yes, Maddy, only haute cuisine from now on."

She let go of my arm at the bottom of the wide staircase to her front door and continued up the short flight alone. "As for the other kind of hot sausage..."

She stopped at the top, turned and sat, folding one leg over the other elegantly.

I watched, hypnotized, as the leg appeared from the slit of her dress, and as she leaned over, letting her breasts tease out the top of their fabric carriage, as she pulled off her shoes.

I was almost hyperventilating by the time she leaned back, shoes in hand, sly smile on her face, and her eyes roaming over my tuxedo'd body.

"Unzip," she said, quietly. 

I quickly worked my zipper with trembling hand, and reached my hands inside-

"Ah-ah-ah!" She shouted, and I froze.

"Do as your told, boy," she sneered. "Don't get eager. Don't think for yourself. Do. As. You're. TOLD!"

I waited, knees trembling, hands at my sides. She turned, the wind moving her hair, and looked into a stand of trees. 

I swallowed again, and fought the urge to beg. Finally she turned back to me, and her face was alive, when she saw my need.

"Now the belt." 

I worked the belt open. 

Her chin tilted downwards. "Throw it down there."

I ripped the belt free and threw it to the stone walkway. 

"Step out of your pants."

I did so, my foot catching the prong on the belt. I let out a little yelp, and Maddie laughed. 

"Ohh, poor boy. It's just a little sting. I'll give you much, much worse pains."

"Please!" I whimpered, the word escaping without conscious thought.

She jerked to her feet, charged down the stairs and slapped me.

"Don't speak!" She slapped me again. "Don't think!"

I nodded, eyes locked on hers, my entire body shivering at her closeness.

She reached out and ripped the tuxedo open. Buttons spilled to the ground and bounced. She ripped it off my arms and threw it down, stepping over it, grinding her feet into the fabric. 

I bit my lip and waited as she walked around me.

"Who do you belong to, Tom?"

"You," I breathed, before the words got out.

"I don't want you. Beth can have you." 

I stopped breathing, unsure how to respond. I half-turned my head, then stopped. Her fingers grabbed the tip of my left ear and turned my head painfully front again.

"Would you ever cheat on Beth, Tom!" she barked, accusingly.

I didn't know what to do. I stood there, shivering from the cold and the intensity of the encounter I'd waited so long for.

Her warm hands touched my hips from behind, then worked their way around and up my chest. I gasped, and it took everything I had not to back into her... just like Beth had ground into me, I realized.

Her thumbs dug into the waistband of my briefs and pulled them to the ground in one motion. A sticky drop slapped my abdomen as my penis spilled free.

She walked around me again. And again. I began to waver... swooning again.

Finally she stood in front of me, and sidled close. Close enough that the head of me pressed against her. Then Maddy moved closer, until her belly was against mine, and my throbbing cock was wedged between us.

"I own you, Tom."

"Yes, Ma'am."

"This could take years. Will you give me ye-"

"I'll give you anything. Everything!"

She chuckled, and didn't correct me on my interruption. Then she stepped back, her smile widening as I whimpered.

I watched her reach down and run her fingers over the dress across the heat of her legs. She rubbed her thumb and forefinger together, then put them in her mouth.

My cock roared as if it was on fire, and my ass tightened, giving a little thrust forward.

She turned and walked up the stairs.

"Go home, Tom. Clean the house and make a nice welcome home meal for Beth. I'll see she's back in time to enjoy it." At the top of the stairs she turned to look back down.

"I see a long future for you here with me Tom. Be a good boy... and wait your turn."

I nodded, fighting not to beg. I wouldn't' beg.

She opened the door. "You'll take Beth to the zoo on Sunday. There's a photo booth there. Be a dear and take a picture of her sucking your cock, will you? I'll expect it in my email before you bed her that night."

She stepped inside, the door creaked. It was almost closed, then sprang back open. 

"Oh, and Tom?"

"Yes??" I almost shouted, and she laughed.

"Boxers only from now on, hm? Silk, only. Oh, and you can take the Aston Martin home. After, you cum. Right there, before you take one step."

The door closed and clicked locked. My hand was already rubbing my aching, throbbing cock.

I gasped and moaned. My head rolled back. My ass bucked again, and I shouted once, loudly as the semen sprayed from the head of me. I found I was on my tip-toes, and my ass was bucking as if it was Beth's face I was fucking.

I finished, sagged back onto my heels, and opened my eyes. The curtains of the leaded-glass door were pulled back, and there stood Maddy, smiling at me.

Then she made a flicking gesture with her hand, and the curtains closed. 

I collected my pants and my shirt, which had little flecks of cum on them, but found that my underwear was missing. Maddy must have taken them with her. 

I smiled as I slipped the clothes on, turning like the little slut I felt like to show her my ass and hoping she was watching as I got dressed.

I wondered what was next, as I walked back to the garage. Then I remembered. I had to shop for dinner, and buy tickets for the Zoo.


