An Oral Contract

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My name is Tony Wilson and I’m 24 years old, 5 foot 11 tall and 170 pounds, with brown hair and eyes. I grew up in the San Francisco Bay Area and spent 6 years in high school and college rowing Crew. I still keep in shape at the gym four times a week with circuit training and swimming. I tried a local qualifier for the Ironman Triathlon last year, but finished in the middle of the pack, probably because I hadn’t trained six or seven times a week like serious athletes do.

After graduating from Berkeley 18 months ago, I postponed starting law school to spend time with my mother. My dad, the judge, had passed away unexpectedly that summer, which shattered so much for mom and me. Her training as a marriage and family counselor didn’t give her a free pass from going through the stages of grief. So mom and I supported each other a lot as we worked to find our new normal life without dad.

I am going to start law school in a few months, but in the interim I’m working as a paralegal with a big downtown law firm. Dad was a partner with the firm for 15 years before becoming a judge, and it was his dream for me to follow in his footsteps there. I really didn’t ask for the job myself. It just took one phone call from my mom to her best friend Judy, who is the executive assistant to the managing partner.

One day of my second week on the job, Judy asked me to take a contract to an important client's house for her signature. I had never met the client, one Adriana Smith Pennington, but the other paralegals called her the "ice queen trophy wife".

The townhouse was in an expensive neighborhood and was the biggest on the block. A servant answered the doorbell then had me wait in the front parlor for, as he called her, “Madame Pennington”. The foyer and parlor were furnished entirely with antiques; I recognized a Stickley table and chairs like my grandmother had in her home.

I waited about five minutes then the lady breezed into the parlor wearing a cream silk robe tied loosely at the waist. I could see a sports bra underneath and by the sheen of sweat on her clavicle she appeared to have been working out.

"You have something for me to sign?" she said, getting right to business with no pleasantries.

"Yes, ma'am. Three copies here. I've got them flagged where you need to sign."

I had the documents laid out on the table. The lady sat down while I waited beside the table. She took a couple of minutes to read the document. I took the opportunity to have a good look at her.

Adriana Smith Pennington appeared to be mid-30's and quite attractive even without makeup. Her long strawberry blond hair was tied back and it looked like her natural color; I saw no hint of darker roots. Her bright green eyes were scanning the pages quickly, to focus in on a few key sections of the contract. Meanwhile, I focused in on the lady’s charms, like where the robe could not conceal the toned shape of her legs, nor the alluring fullness of her bosom. The aromas of her sweet perfume and tangy sweat blended nicely, and made a lasting impression on my senses.

After signing the contracts, she turned her face to me. I saw her gaze stop for just a moment to notice the tent that had developed in the front of my trousers. When her eyes got to mine, I was beginning to blush. With only a flicker of a smile, Madame Pennington resumed her no-nonsense business face.

I let a smile creep onto my face slowly, the sexy one that has never failed to encourage an erection. What an afternoon treat, this pretty little paralegal. Heaven sent, it seemed, as I had just lost my last slave to a relationship. Judging from the bulge, he was just the size, too.

I liked to see how men reacted to silence, so I let it hang in the air a bit. I wondered how Carlyle, my husband, would react later when I told him. He'd probably call me a tease, playfully, and he would be right.

I uncrossed my long legs, letting the robe fall open a bit more while I handed him back his papers.

"What's your name, hmm?"

I let my voice roll huskily, watching him.

"It's Tony ma'am, Tony Wilson."

The lady didn't seem to have anything else to say to me, so I offered a compliment.

"Ma'am, I must say you have a beautiful home. I love the antiques and this Stickley is amazing."

"Impressive. Stop with the ma'am. If you must call me something, Madame will suffice."

I raked my eyes over him again. Strong...he definitely works out. Always a plus, I've never liked weaklings.

"Men have to earn the use of my first name."

I brushed my hair back over my shoulders, deliberately allowing a glimpse of the swell of my cleavage, round and ample.

I couldn't help looking at her cleavage when she brushed her hair back. I kept reminding myself to behave, that she was an important client.

"So uhm, Madame, I think I'd better get going back to the office. That is unless you have anything else you need me to do for you. Miss Judy said to ask you that. You know Miss Judy? At the office? I think everyone knows Miss Judy."

"Did she now? Very good of her. I've always been partial to Miss Judy."

My lips curled again. Judy knew my husband and I well and had always been a great help with our...interests. Of course she'd send the new dish to deliver my papers, she had to have known what would happen.

I stood, not bothering to fix my robe, which was now barely tied. The slit in the front exposed a line a creamy skin and showcased the fact that I had not put on any undergarments after my workout.

"Actually, Tony, I wonder if you might be interested in a position..."

I let the deliberate innuendo hang.

When the lady stood up, her robe opened a bit more in front. Before I could stop them, my eyes glanced downward just long enough to notice she wasn't wearing panties. When my eyes returned to her's, I knew I was busted. I listened to her question. Was I interested in a position?

"No. Er, uhm, I mean I'm working just for a couple months at the law firm, then I start law school."

My answer didn't seem to satisfy the lady, so I asked, "Madame, what kind of position would you be offering?"

I moved a little closer to him, robe swaying with my swinging hips, allowing brief glimpses of my body. Certainly enough to show him that I was fully shaved and aware of his roaming eyes.

"Well, Tony, I'm working on a book. My primary interest is anthropology, with a focus on human relationships. I could use a dedicated research assistant."

I paused, reaching up to tug on his tie.

"The book is about domination. And submission."

The way she moved and her tugging on my tie caught me by surprise. I was painfully aware that I had a boner, and was embarrassed by it. The lady was an important client and a married woman. What do I do?

"I have no experience with that Madame. But I think I'm very good at research and did well in pre-law. Would that really qualify me for what you have in mind?"

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"Hmm."

I did not move back, though he was obviously uncomfortable, especially in the pants. He was young enough that this came as no surprise. It would be fun to teach him, I thought. Ever more I became sure he would make a perfect pet. Time to take the idea further...

I slid a hand down to his straining erection, covering it but not squeezing.

"I think you're more than qualified. You reacted to me, you sound sexy when you call me Madame.

Mind you, Tony, this is not a position with a salary."

I now had no doubt that the position being offered was nothing my education had prepared me for. Everything about Madame Pennington--her beautiful face and what I could see of her body, her alluring scent, and now her brazen hand--made a compelling case for me to say yes. Her bold self-assurance made me believe the lady was not accustomed to taking no for an answer.

"I understand Madame, no salary, but may I ask about the hours and benefits?"

I stroked my thumb over his long, thick cock while I spoke. I could feel it jumping inside his pants and boxers, already eager to obey me.

"I will require you for two hours after your shift at the firm. Every day. You may have to stay late sometimes, but in that case I will make generous accommodations.

Your benefits will be slightly painful, warm, wet, and very satisfying. Your benefits are pleasure beyond anything you can imagine.

Do you think you can be a good boy for me, Tony?"

"Yes Madame, I do. You'll tell me what I must do to be a good boy, right?"

Her finger was strumming over the crest of my cock head, where there was now a wet spot in my slacks.

"So we <gasp> Madame, it seems we have an oral contract. I <gasp> I need to know <gasp> is cumming in my pants being a good boy or bad?"

I lick my lips, studying his face. Oh, he's going to be fun.

"Just this once, dear. But you'll have to learn to control yourself better in the future."

I trace the very tip of his throbbing member through his pants, smiling down at the wet spot. I reach up, exposing one breast, perfect pink nipple puckered.

"You may cum for me now."

I was lost and I knew it. It was like rowing in choppy waters when both oars don't bite together. I'd never had a premature ejaculation and certainly never cum in my pants before. Of course I'd never been in this position before either.

Madame was rubbing my cock head through the wet fabric of my slacks when she pulled her robe aside to reveal the most perfect breast I'd ever seen, with a nipple that seemed begging to be sucked. Then she said "You may cum for me now."

I groaned out loud as my jism exploded in my boxers, making the wet spot in my slacks bloom hugely. It was such an embarrasing moment and as soon as I could put words together, I said, "Madame, I truly regret my lack of control. Please forgive me."

When I hear his delicious groan, I squeeze his cock, relishing the feeling of it exploding under my palm. I keep rubbing, softly, with just two fingers as he empties himself. Then he apologizes and I know I've made the right choice. He'll be perfect and more than ready to serve me.

"Oh, you'll make up for it."

I pull my robe closed and retract my hand, fixing his eyes to mine.

"You start today. Six o'clock exactly. I assume I don't have to tell you that lateness is intolerable?"

I gathered up the contract copies and put them into the large file folder I brought them in. The large brown folder was just what I needed to hide the large wet spot I now had in the front of my slacks. I hurriedly left the townhouse and got in my car. I knew I had to get home and change clothes before going back to the office.

I arrived at home and thanked my lucky stars that mom wasn't home early today. I changed clothes quickly and rushed back to the office. I'd been gone over two hours and came back wearing different slacks. I don't think anyone noticed.

Miss Judy seemed pleased that I returned with the contracts signed. She smiled as I handed them over to her, but if she noticed my change of pants, she didn't say anything.

The rest of the afternoon was as non-productive as I'd ever been. I was too anxious thinking about arriving at Madame Pennington's at exactly 6 pm.

I drove from work to the townhouse, getting there at 5:20. Too early, so I went to a drive through restaurant for a quick bite, then returned and parked down the block from the townhouse.

I rang the bell at 5:59 according to my watch. I hoped that would be on time for the Madame.

One of my staff had been instructed to let Tony in, and I was pleased to see him ushered in at exactly 6. I didn't show it, of course. I didn't even greet him. The butler shut the door and I stood, behind my desk. I was now in a black silk robe, with plenty of surprises underneath, and towering stiletto heels he could not yet see.

"Strip."

My voice was harsh, appraising him.

"Down to your boxers. Fold your clothes on my desk, your tie on top, as your Madame will need it. You will do this every time you enter my office.

I expect you to arrive hard, as well.

Do you understand, Tony?"

After ringing the bell, the door was opened within seconds by the same man I’d seen in the afternoon. He was an older gentleman and, by the looks of his uniform, the butler. I was ushered into the room across the foyer from the parlor I’d been in earlier. Like the parlor, this room had a large stone fireplace and was furnished entirely with antiques, a side table and chairs, bookshelves along the wall on either side of the door, and a large oak desk.

Madame stood behind the desk, wearing a black silk robe and looking even more stunning than before. My cock had been half-hard with anticipation as I rang the doorbell; the sight of Madame definitely got my heartbeat up and my erection too.

As soon as the butler shut the door behind me, Madame said, “Strip,” and told me exactly how I would do this every time I entered her office. She expected me to arrive with an erection, which I didn’t think was going to be a problem. “Do you understand, Tony,” she asked?

“Yes, Madame,” I replied.

I quickly undressed exactly as she said. I folded and stacked my clothes on the desk, with my tie on the top of the pile. I noticed how my hard-on was straining at my white cotton boxers.

Then I took one step backward and stood with my hands at my side, hoping that I had been a good boy so far.

I took a moment to let my eyes wander over him. The sight made me wet, but he didn't need to know that just yet. Tony was in peak condition, lanky and cut, his body much like a swimmer's. My favorite.

I came out from behind the desk, towering in my heels, which clicked on the wood floor. I stopped just in front of him and silently appraised his erection, pressing out fervently in the white boxers. The outline was perfect.

I ran my fingernails down his chest, dancing lightly.

"Before we get started, my Master wants to inspect you. You will not speak unless spoken to and you will respect him as you would your Madame.

Don't embarrass me, Anthony."

Madame walked around the desk to stand directly in front of me. In high heels, she was a couple inches taller than me and I had to look up to meet her gaze. I saw her glance down at my bulge, but saw nothing in her expression that said she approved or otherwise.

Madame traced her fingernails down my chest then her eyes returned to mine. She spoke slowly and precisely, “Before we get started, my Master wants to inspect you. You will not speak unless spoken to and you will respect him as you would your Madame. Don’t embarrass me Anthony.”

I didn’t know what I expected tonight, but I was not prepared for what she said. Her Master? I did not see that coming. But what really sent a chill down my spine was that she called me Anthony. No one ever called me that, except for my mother when I was a kid and had done something very bad. Hearing the name as an adult still had an unnerving effect on me.

"I won't, Madame."

I walked back to my desk and pressed the button that would ring in Carlyle's study, which adjoined mine. It was barely ten seconds later that he stepped through the door, though you would not know it was there, since it was hidden by the bookcase.

My husband, my first and last dom, is an imposing man with salt and pepper hair, piercing blue eyes, and a barrel of a chest. He strode into the room, glancing at Tony before looking at me.

"Sit down, Adriana."

"Yes, sir."

I sat at the desk, folding my hands in obidience as Carlyle approached my new pet.

I waited silently at attention, afraid to even fidget. I noticed the bookshelf move then a big man with salt and pepper hair step around the corner. He took one look at me and said to Madame, "Sit down Adriana" to which Madame replied "Yes, sir" and sat obediently.

As the man looked me up and down, I got a pretty good look at him too. He was maybe 6 foot 1 and 200 pounds, handsome with bright blue eyes and white, even teeth. I couldn't guess his age, but he seemed to be my father's generation, although he looked very fit and healthy for that. There was something familiar about his face, like I'd seen it before in another context.

I kept my mouth shut.

Carlyle's face never showed what he was thinking, I knew that all too well. I felt a bit squirmy in his presence, as always, but I did my best to hide it. It wouldn't do for Tony to see me go fully submissive.

Carlyle turned his eyes to me.

"Cute. Good age. He has potential."

I smile. "Thank you, sir, I thought so."

He turned back to Tony, crossing his arms, the muscles in his chest rippling.

"Tony, right? I wonder if you realize yet how lucky you are that this little minx chose you. Are you prepared to serve her?"