An Oral Contract

That orgasm was good for me too. I was on a sexual high and I didn't want to stop. I slowed my thrusting to give us a little breather. Madame was looking up at me, mouth slack as she gulped air.

I gave her some more dirty talk between thrusts, "You're a real . . . hard cummer . . . aren't you . . . pussy gusher . . . I like 'em like that . . . gonna cum again!"

I accelerated again, slamming into her vigorously and urging her toward another orgasm. She was beautiful in her ecstasy and her second cum led right into a third cum. By then I was too close to the edge myself and I didn't slow down. My cock was throbbing and spewing into her convulsing pussy.

Madame hadn't said where I should finish, so I stayed deep in her hot pussy, flooding her with my seed. I lowered my head to her shoulder, panting hard.

"That was . . . you are . . . incredible Madame . . . amazing . . . epic!"

I thought my time was probably up for tonight and wondered about how to exit gracefully. Then I began worrying about tomorrow.

I was insensible by the time he finished, my face red and sweaty. Though I was gratified, I knew I had failed. I never should have given him control so soon, never should have let him know what turned me on. It gave him power.

His dick was softening in me, his cum leaking out of my pussy onto the desk. I could feel his hot breath on my shoulder, hear his satisfied words on my skin. As much as I did not want to, I had to reassert myself. I pushed on his chest, easing him off of me, hoping he did not hear the quaver in my voice.

"Very good, Anthony. Dress and get the hell out of my office."

Madame called me Anthony this time, so I knew I was in deep shit.

I dressed quickly, looking anywhere but at Madame. I put the collar in my pocket. Before I exited the office, I turned with my head bowed and my gaze on Madame’s feet, to say with genuine contrition, “Goodnight Madame.” I didn’t expect a response.

I left immediately, got in my car and drove home. Of course, at 8:30 on a Wednesday evening mom was there. I wanted to avoid her and get right upstairs to my room, but she heard the click of the front door.

“Tony? You’re late,” she stood in the kitchen doorway. “Extra work at the office?”

“I should have called. I went for a workout.” I lied, which I rarely got away with.

“I kept your dinner warm. You’re probably hungry. Come eat and talk with me.”

I sat down at the table and mom served me. I knew she wanted to take care of me even more with dad gone. We talked about our days and of course I had to lie. I didn’t get away with it. I reeked of sex. She didn’t ask, but she knew something had happened and I knew that she knew it.

I slept poorly that night. I kept thinking of different scenarios for my next meeting with Madame, and they were all going to be painful.

* * * *

The next day at work was fraught with worry. I worried that someone would see my red-chafed wrists, although I kept my long sleeves buttoned. I worried that I would slip up and say something about Madame. I worried that I had failed horribly last night and that Madame would never forgive me.

Miss Judy called me to her office that morning. I was sure that I was going to hear that Mrs. Adriana Smith Pennington had complained about me. I was wrong. Miss Judy was nice to me, as usual. Like my mom, Miss Judy knew me very well, but today she didn’t seem like anything was amiss.

Miss Judy gave me the file copy of the contract Madame had signed yesterday. I was asked to file it. I went to the file room and took a minute finding the box in the active accounts shelves, labeled Pennington #6. While I was notating the latest addition on the index log sheet, I was impressed that the index was 23 pages long. I looked back through the pages interested to see how many years Pennington had been represented by the firm. What I found shocked me.

The first dozen pages, starting from twenty years ago, were all initialed with “JW”. My dad, John Wilson, had been Pennington’s attorney. Then one particular line item on the first page caught my attention. It was a contract for the construction of an 80 foot yacht. That notation jogged my memory to the time when my dad was first appointed to the bench, 15 years ago; I was 9 years old and dad brought me with him one day onto an enormous boat. It was a day-sail out to the ocean and there were a dozen men there, my dad’s friends. I remembered being thrilled to hold onto the wheel, to steer the boat for a few minutes. I remembered a tall blond man, with a big smile and a big barrel chest. I’m sure I met Carlyle Pennington when I was a boy.

After lunch, I had a moment alone with Miss Judy and I asked her what she knew of my dad’s relationship with Mr. Pennington outside of work. Her reply was that was not her business and I should ask Pennington.

* * * *

At 6 p.m. I stood on the doorstep of the townhouse. I already had my collar on as I rang the bell.

Almost as soon as Tony left, Carlyle opened the bookcase-door and strolled into the room. I had expected him to be furious, stalking in, but he was holding a newspaper and he barely looked at me. I was still splayed against the desk, naked, with another man’s semen leaking out of me, and Carlyle barely glanced over.

“Take a shower,” he said, his eyes finally grazing me, but not settling. He tapped the paper against his thigh, terrifyingly casual. “My study, ten minutes. No more than ten minutes, Adriana.”

When I entered his study, in a long and flowing peach nightie, I immediately knelt at his side. I had not done so for a very long time, as he had been training me to be dominant. Carlyle looked down, meeting my eyes, and stroked my hair. I didn’t say anything, I knew better…he would speak first.

“One session and you let it get out of hand. Some kid barely out of college and yet you cannot keep control. I am both shocked and disappointed.”

I did not apologize; he did not want an apology. “I know.”

“I should stop this,” he said. “But there is the book to think about. And as much as a failure tonight was, it was your failure. Tony was perfectly submissive in every way, until you let him open his filthy mouth.”

Which I had loved…but that was not something Carlyle needed to hear. It did not matter, because he was unzipping his pants, which meant I was to immediately put my mouth to better use than arguing. His cock was soft when I put it in my mouth, but it did not stay that way for long. He continued stroking my hair.

“I know why you let him fuck you so soon. He’s handsome, he’s eager, and he must be talented. You have the rest of the week to get him in line, and if you can’t, I will have to step in.” I was moving up and down on Carlyle as he spoke, but his voice remained steady. His hips, however, did not. He thrust himself further in, not gently. He fisted a hand in my hair and yanked roughly. He meant to make me gag, and I did. “Go get your collar, Adriana. You need a throat fucking, and I mean to tie you up while I do it.”

****

I slept in the next afternoon, then spent the day recounting the first session in my notes. I dressed to receive Tony, this time in my bedroom.

The door opened for me almost before the chime faded. The butler had to be waiting in the foyer. He said, "Follow me, young man," and led the way up the broad, grand staircase. At the landing we took the left-hand steps upward. There was a balcony above the landing and hallways in three directions. We took the hall toward the rear of the house, which had a door up a short distance on either side and another door at the end about thirty feet away.

The butler knocked on the left hand door and waited two seconds before opening the door. I was ushered into the room then the butler left and shut the door behind him.

I was in a bedroom, Madame's bedroom, and she stood there waiting for me. I avoided her eyes and immediately cast my own eyes down at the floor, bowing my head. I waited for her to speak first.

(Attached, what Madame is wearing for this second session.)
______________________

"I am pleased that you are wearing your collar already, Anthony, but you have not undressed."

My room is designed to be debauched and though it looks like a bedroom, it's rightfully a playroom. It was a gift from Carlyle upon my graduation to dominatrix, which now seemed to be in question. He had kept me up for punishment, well into the night. I hoped this would not be my last time in the room.

A large chest stands in the corner, shining black lacquer, and all the curtains and bedding are a deep red. Every inch of furniture is mahogany, the wood shining and oiled. Candles burn to illuminate the room, but there is no other light.

"I will at once, Madame."

I took my clothes off quickly, folding every item carefully and stacking them on the floor beside me. In the light of a dozen large candles that stood around the perimeter, I noticed the room's mahogany furnishings, a large four post bed, a table and two chairs, a large leather upholstered bench. A large black chest stood in the corner.

I sneaked a peek at Madame; she looked awesome in a little black dress and a black leather corset. She was not smiling.

As soon as I was naked, I dropped to my knees before Madame. I was intent on showing total respect and obedience tonight. I hoped to obtain mercy.

I walked over to him, stopping beside him, my thighs and short skirt in his eyeline.

"Good boy."

I did not touch him at all, just stood next to him. He made quite the tantalizing picture, kneeling for me, his tight chest pushed out slightly. He had instinctually put his hands behind his back, too.

I had worn black stockings to hide the fact that my knees showed a prominent rug burn from my own punishment.

"But you have been bad indeed. Tell me, are you hard?"

I could, in fact, see that he was, but I wanted to hear it.

"Yes, Madame, my cock is very hard."

I flexed my pubocoxyc muscles to make my erect shaft wag up and down. It was a cheap trick, but one I hoped Madame would appreciate.

I snickered, I couldn't help it.

"Cheeky, Tony. Sit on the edge of the bed--I want you to stroke yourself while you tell me how you felt today, after our first session."

I paced in front of him, my ass swinging.

"I should mention, I am recording these sessions for my book. I will not use your name, to protect your privacy. If you have a problem with this, you must tell me now."

"No problem, Madame."

I sat on the edge of the bed and took my cock in hand. I stroked it slowly as I told about the past 22 hours.

"Physically, my ass is still tingling and sore. Worse, I've been challenged emotionally. When I got home last night, my mom met me. I had to lie about what I'd been up to. I'm sure she could smell the sex, but she didn't say anything."

"At work today, I felt sort of a guilty pleasure about having a secret. I felt someone might see the redness on my wrists and ask about it. Miss Judy didn't say anything, but she can be pretty guarded. Mostly, I felt something different than usual, like being fortunate that I have something special that other people didn't have."

"And I'm sorry too, Madame. You showed me mercy by not whipping me too much. Then you let me have control and I took advantage of it. I apologize for any disrespect I showed to you Madame, or to your Master."

I listened as Tony summarized, feeling pleased with all of it, down to the fact that he knew he had crossed the line last night.

"Keep stroking."

I wandered closer to the bed at a very languid pace, my eyes roaming him.

"Did you consider not returning to me?"

"No Madame, I did not. But I did worry that you would not take me back or let me apologize."

"I feel I owe you a great debt that must be repaid. I committed to trust you then I took advantage of you. I promised to be submissive and I failed you Madame. I will do better, Madame, if you give me another chance."

"My Master has given me a week more to see if you can obey. If you fail, I'm afraid I will have to ask for your collar back."

I glanced to the discreet camera in the corner of the room, knowing that Carlyle would be watching closely. I then looked back to Tony, his hand still working his cock.

"The cellphone on the nightstand is yours. I expect an answer to texts or calls immediately, barring emergency. Do you understand, Anthony?"

"I understand, Madame. I must obey. I must answer you immediately. I have one week to prove myself."

I stroked my cock with even more purpose now that I knew that Madame hadn't already dismissed me. I was determined to be obedient and submissive as could be. But I also had to tighten my pubocoxyc muscles, because I couldn't let myself cum before Madame told me to.

I shimmied out of my skirt, dropping it to the ground. Underneath, I wore another pair of open panties, but they couldn't rightfully be called underwear. They were basically only strings framing my pussy and a thong up the back. I bent to retrieve my skirt, deliberately giving Tony a full view of my tight, round butt.

I meant to bring him to the edge of orgasm, but deny him. At least twice, I thought, before I would finally let him release.

I watched Madame closely for any non-verbal communication, any clue. Every movement, every facial expression, every voice inflection was in harmony and proof that she was in total control today. She would not let a repeat of yesterday happen.

Madame paced back and forth slowly as she spoke, not nervously but more to keep my eyes on her sexy body. Then she removed her skirt with as much flair as a stripper but keeping a serious demeanor. When she turned her back to me and bent over slowly, it piqued my lustful attention. I could see her beautiful pussy today showed none of the wetness it did yesterday.

Madame was definitely in control of herself and all business today. I was all the more impressed and ready to be put to the test.

I came to the bed, crawling on and arranging myself back against the pillows. I waited for him to turn to me, then opened my legs, knees bent. I ran one finger down my pussy, feeling wetness begin.

"Today you will be making up for yesterday. I expect you to bring me to my peak without the use of your big, hard cock. You may touch yourself, but you may not cum before me."

I flicked my clit, knowing that if he saw me touching myself, the vision would make it worse for him.

"When I finally do let you cum, Anthony, you will do it into your own hand and then I will watch you lick yourself clean like the dirty boy you are."

The thought of it made me wetter and I slipped a finger inside myself. I saw the camera do a infinitesimal zoom. Carlyle.

I watched Madame walk by me and climb onto the bed. She reclined on a large pillow at the head of the bed. As I turned around to face her, she spread her raised thighs, planted her feet wide apart and rested one hand on her pubis. She rubbed one finger teasingly over her pussy lips while she gave my instructions. I was to provide her orgasmic pleasure, but was forbidden to use my cock.

“As you wish Madame,” I said, moving to kneel between her feet.

I rested a hand on each knee and began gently kissing one leg then the other, working my way up her inner thighs, gradually nearing her center. My saliva was flowing profusely and my breath was blowing hotly on her flesh. By the time my lips arrived at the crease of her crotch, I’d painted a shiny streak down both thighs. I knew the glint of wetness I saw in Madame’s pink folds was not my saliva.

I breathed deeply of the fragrant flower of Madame’s pussy then blew over it and inhaled again, savoring the way her aroma provoked my own pre-cum. I moved then from my knees onto my belly, putting my arms beneath her thighs with my elbows on the bed and my hands on her hips. I was comfortable now to spend whatever time Madame required of me.

I lowered my mouth to her labia, kissing on the right and left, but still keeping away from her inner folds for a while. My strategy did not work for long, as Madame soon grabbed me by the hair of my head and pulled me right to the center. I was only too happy to be directed.

I kissed and licked at the delicate inner folds, nipping them and bringing them out to play. I dragged my nose through the growing wetness and Madame moaned. I rubbed my nose over the hood of her clit and blew warm puffs on the emerging bundle of nerve endings. I flicked my tongue along the hot pink pussy petals and against the inner walls as far as I could reach.

Then Madame raised her left leg to hook around my head and pull me in tighter. I knew she wanted to cum soon.

I licked and sucked on her labia. I fluttered my tongue on her clit then sucked it. I wanted Madame to cum too. I hoped she would enjoy several nice ones tonight.

"Oh...oh, yes..."

I felt my thighs close around Tony's head, effectively trapping him in my pussy. He did not let up and I felt my pleasure building. I arched, my pelvis rising to meet his tongue and lips.

My first orgasm came in a rush, the wetness seeping onto his tongue, which he lapped up quickly. My breath left me in a whoosh and nipples strained against the rough fabric of the corset. I gently eased Tony back with a foot.

"Very...very good."

I sat up a bit, looking down at him with hot eyes.

"Do you like servicing me, dear boy?"

"Yes Madame. Very much. I've never known a woman to have such amazing orgasms. Servicing you is quite, uhm, well I suppose I'd say it's inspiring."

I raised up on my knees to show my stiff, drooling cock.

"See how you inspire me, Madame. Shall I service you more now? What would you like next Madame?"

I was almost too eager, but I wanted Madame to know I was committed to serve her.

I smiled, eyes flicking to his cock. I lightly traced the tip, smearing the precum around it.

"Do you think you can bring me to climax with just your fingers?"

His eyes were overly bright, he looked almost mad to please me. Good. We were getting back on track. As much as I had enjoyed him seizing control--and I had, he was an amazing fuck--that was not the point of his submission. It would be a reward, much later down the line.

"Yes Madame. How many? More than two?"

I scooted up closer and began with two fingers tracing over Madame's labia. I looked up at her face and saw her smile, almost. I caressed her folds with four fingers, parting them wider and drawing my fingertips through her wetness. I slipped one finger deeper and stirred around the walls. Madame opened herself to me and I slipped two fingers in.

I pressed deeper and rolled my fingers around in circles, rubbing everywhere. I pumped in and out a couple times, getting my fingers slick with Madame's juices. Then I slipped my fingers deeper to reach her g-spot. I found it waiting for me, hot and sensitive. I turned my fingers and began caressing the spot. I heard Madame groan and I knew she was ready for more.

With my two fingers inside waving over her g-spot to come here, I rubbed my thumb on her clit. The pressure on both aroused zones at the same time affected Madame as I hoped. She was beginning to squirm inside and tense up on the outside. I kept the pressure and movement on until she climaxed.

Shuddering violently from my g spot orgasm, Tony's fingers still in me, I arched up against him. The urge to let him fuck me was almost overwhelming. I could barely think to command him anymore. I tried to force myself back to consciousness by looking up at the camera. The little red light blinked, indicated my Master was still watching.

I sat up, unsteadily, and unhooked my corset. My breasts fell to the open air, nipples small and pink, aroused. I laid down, taking my tits in my hands and gazing at Tony while I pinched my nipples.

"Kneel over me. Stroke yourself."

I am a lucky man. That thought occurred to me as Madame was rocking her orgasm on my fingers. I am a lucky man to be in this position, pleasuring a woman who really appreciates it. I was not so lucky with women in college. Maybe it was me. I was only with a few women, but none of them was this responsive. Madame was a glorious revelation to me and teaching me a valuable lesson.

So I exulted as Madame came. I was excited to see her take the corset off. I lost control last night, but I wouldn’t do that again. I was a lucky man and I was not about to fuck this up, so to speak.

I obeyed Madame at once. I raised myself up on my knees and stroked my hard, drooling cock. I was ready to cum when Madame said to. I was ready to catch my jism in my hand and ready to lick it all up. Because I knew this was not for my pleasure, but for Madame’s.

I am such a lucky man.