An Oral Contract

I watched Tony, his thick cock in his hand, hovering above me and glistening. He was such a natural submissive, so obedient. I reached up to stroke his hair.

"Good boy...you've been a very good boy tonight."

I pushed my breasts up and together with my upper arms, round swells beneath his gorgeous shaft.

"I've changed my mind...I want you to cum on my tits and lick it from there."

I'm a very lucky woman, I thought.

When Madame said “Stroke yourself”, I was happy to obey. I pumped my cock assertively.

When Madame said “Good boy”, I spanked the monkey even faster, seconds away from filling my other hand with a hot load.

When Madame said “Cum on my tits”, I could scarcely adjust my aim fast enough. I flexed my pubocoxyc muscles and spewed a half-dozen pearly trails over Madame’s magnificent globes.

Then without a moment’s hesitation, I leaned down and licked up every drop. Even licking a few places where there was no drop.

“Thank you Madame.”

Without hesitation, to the letter, he obeyed. Any domme would begin to suspect he had done this before, but I knew he had not. I knew Tony had been a sheltered child, because Carlyle had known his father. The red light on the camera blinked off.

I looked up to his breathless face, deep eyes gazing down at me. I was having the urge to open up to him, something I knew would be folly and would also compromise my research. I couldn't very well hold him, though that was my immediate urge.

"You may lay at my feet now, Tony."

I curled up on the bed at Madame's feet, keeping my eyes fixed on her face. I forced myself to keep alert and not fall into a post-orgasmic torpor. It was a challenge, for I truly felt at ease, warm and satisfied in Madame's presence. I wondered if this was what a submissive should feel for his domme. I felt like I was still clueless about what I was doing.

"Permission to speak Madame? Am I working out to your satisfaction? Meeting your needs for a research assistant? And if not, what else must I do?"

I looked down at Tony, laying prone and worshipful. He even asked permission to speak. His learning was rapid, but I knew I had been going easy on him. I knew just as sure as my own Master did. The next session would not be so simple.

"You are progressing, Anthony, but you need to know that I will be asking you to do things that will make you uncomfortable. You are always welcome to use the safe word. I will respect it, but we will also discuss why.

In the coming days, I expect you to begin keeping track of your feelings. There is a leather journal next to your new phone in which you will record your thoughts. My Master may attend a session and you may have to interact with him.

Do you understand?"

“Yes Madame. Thank you for starting easy on me. I don’t expect to be coddled, but I appreciate your kindness. You’ve been fair to me and I hope to be honest about my feelings. I promise I’ll do better in my next interaction with Master.”

Even as I promised, I wondered how I would respond when confronted with something I really didn’t want to do. I realized there was so much I didn’t understand. I had so much yet to learn.

I sat up enough to reach him and stroked his hair once, placing a kiss on his cheek.

"Now dress and go home. Do not forget your gifts and I will see you tomorrow."

I refrained from adding the 'good boy' this time, as I had already praised him enough. I desperately hoped I had pleased Carlyle this session, but I knew I was in for another lecture and possible punishment. It was clear I had affection for the boy, and that was going to be a problem.

I dressed in silence, afraid I may have said too much already. Oh well. She asked about my feelings and I tried to be honest.

I picked up the cell phone and the leather bound journal, thinking both items were evidence of commitment to our relationship. I intended to keep my end of the contract.

"Thank you for the gifts Madame," I said and nothing more. Then I left the room and went straight home.

My mom was not waiting for me. She'd left a note, 'be back late, casserole in the oven'. I ate some, had a little wine. I wrote in the journal, mostly what I'd told Madame already. Plus I wrote about my wondering what I will do when asked to do something I'm not comfortable with.

I slept well and deep. Woke the next morning feeling very refreshed.

Work was even more boring than usual, now that I had a very secret position in the back of my mind. Always.

I did not get punished in the end, though I did get fucked soundly. Carlyle flipped me over and teased me for being too kind to my sub, ramming into me all the while.

The next afternoon, I texted Tony.

On your lunch break, I want you to go to the department store. Buy a pair of lace panties and wear them for the rest of the day.

I heard a tone from my phone and quickly checked for a message from Madame. I’d been expecting her to make my next task a challenge, and I was not disappointed. Lace panties? I replied by text ‘Yes Madame”.

Fortunately, my office was only a few blocks from Union Square. I’d have plenty of time to walk there on my lunch break and pick up a sandwich on the way back.

I figured Macy’s would have a good selection, so I went there to shop. Lingerie was on the second floor. I quickly selected a black lace item. The hardest part was deciding what size to get. Trying not to seem too creepy, I watched a woman select a size 10 off the rack, decided my hips were smaller, so I picked size 8. The salesclerk didn’t bat an eye when I paid for them. If she only knew!

I took my purchase back to the office and changed in the men’s room. The size fit OK, a little snug in the waist band and of course with no pouch in front. Walking back to my workstation was a new experience; the lace rubbed my cock with every step. I wore them the rest of the day, feeling self-conscious enough that I was sure others were starting to guess my secret.

I arrived at the townhouse right at 6 p.m. and rang the bell. My cock was hard and I could feel its head sticking out above the panties waist band.

It was Carlyle who answered the door, not the butler. I knew that he wanted to examine the new sub further, but I had been dreading it. Possessively, I wanted to keep Tony to myself. But I could not very well tell Carlyle no.

I watched the exchange from the monitor in the study. Thanks to a microphone in one of the potted plants near the door, I could hear Carlyle, but Tony's voice was a barely distinguishable mumble as he stood on the porch.

"On time," rumbled the voice of my husband, my Master. "Are you wearing what your Madame requested?"

He made no move to let Tony in; his whole frame filled the door.

Carlyle Pennington opened the door and I immediately felt challenged. I wasn't sure how to behave, but I was certain I needed to be even more submissive to the Master of my Madame.

The man had not said to come in, indeed he stood in the doorway. I didn't move except to cast my gaze downward. He asked if I was wearing what Madame requested.

"Yes Master." I answered, without offering any comment. I was not about to presume anything. I would carefully, precisely do what I am told, and nothing improvised.

Carlyle stepped aside to allow Tony to come in the house, but he did not move enough that Tony could pass without brushing him. The subtle ways that he dominated were a lesson to me always, and I was always impressed.

"I am not technically your Master," I heard Carlyle say, shutting the door. "Though I could be, if you make it past this week."

He strolled down the hallway, expecting Tony to follow. The lens of the little camera moved with them and I was treated to the view of both of their backs.

I could tell Pennington wasn’t going to make it easy for me. By stepping aside a bit, he tacitly gave me entrance, but only if I brushed against his larger body to do so. I was close enough that I couldn’t miss his cologne, which was pleasantly old school, like aged bourbon and fine cigars.

Then he corrected me and made it quite clear that my status here was still conditional. I kept my mouth shut.

When he turned and walked down the hallway, I followed closely but not too close. About half way down the hall, it opened to an alcove on either side. Pennington stopped by the left alcove, where I saw a closed door with a low bench beside it.

“You will leave your clothes on the bench, except for what Madame required. Put that blindfold on, tied securely.” I could see a long strip of black cloth hanging over the door knob. “Then you will enter the room, shutting the door behind you. Madame will be waiting for you inside. Or she may keep you waiting for her. That is her choice and you won’t know until you’re inside.”

“Remember these directions, boy. You will be expected to present yourself to Madame like this every night for the rest of the week.”

With that, Pennington left me.

I quickly stripped and folded my clothes on the bench. I couldn’t get my stiff cock to tuck inside the lace panties, so I left it poking above the waist band. I picked up the blindfold, stretched it over my eyes and knotted it behind my head.

I opened the door, stepped through into the next room, and closed the door. I waited. The floor was colder than in the hallway; it felt like stone or tile.

Carlyle's playroom was larger than mine and it was where I had learned everything I knew about love, domination, and submission. Tony stood near the door, the blindfold making it impossible for him to know that I was standing barely ten feet away, watching him. I wanted to see what he would do if he was made to wait a bit. Was he a shuffler? Would he sigh? Would he go soft?

I hoped not the last one--his gorgeous, rock hard cock poked out of the little lace panties in a very arousing way. I liked that he'd bought a pair a bit too small for him, even if he had not meant to do so.

I ran my fingers over the nipple clamps in my hand, no sound in the room disturbing the quiet. I heard Carlyle enter behind me, the door making no noise at all. The room was sound-proofed beyond belief--it had needed to be, I was very vocal in my submission in the early days.

Carlyle wound his arms around me, cradling my naked breasts in his hands from the back. I wore only a red thong and heels this time.

I stood waiting and wondering. What did Madame have planned for me next? Pain? Pleasure?

Pennington said Madame would be in this room. Didn't he? I wasn't sure. I couldn't hear anything but my own breathing and heartbeat. The silent, sightless waiting was strangely exciting. What was I waiting for?

I shivered. Did I feel a breeze? Was Madame standing right in front of me, watching me wait? Was my cock still hard? I think so.

I wondered if Pennington would be watching me? Had he been watching all along? Was it Madame that would ultimately decide my fate, or her Master?

I waited.

I nudged Carlyle's hands away, eager to get to my task. Tony was waiting patiently, still poking out of his little panties. A delicious sight.

I approached him, my heels clicking in the marble floor. I did not speak, but ran a hand up his torso, starting from the tip of his cock and ending at his left nipple. I pinched it until it stood at attention.

Then I captured it with the metal clamp and closed the mechanism.

I heard the click of high heels echo in the room. Madame had been here all along, watching me. As she stepped closer, I could smell her perfume and the hint of Pennington's cologne.

She rubbed a fingertip over my cock head then traced a line up to my nipple. She grabbed the nipple and pinched it, twisting and pulling it. She pinched hard, painfully hard then let go. Before my nipple could begin to throb, I felt something cold latch onto the raised nub and tighten.

The pain was horrible, bringing tears to my eyes and causing me to whimper. I thought of my safe word, but kept from speaking it. This pain was bad, but so was that whipping the other night, and I survived that.

Madame started working my other nipple, pinching and pulling hard. By the time she latched onto it, I was so shaken that I couldn't stop my yelp of anguish. I clenched my fists and almost raised them against Madame. But I knew I was only getting what was promised and what I promised to accept.

What could be next?

I watched as he squirmed, my eyes taking it in. For a moment, I thought he was going to use his safe word, the way his hands balled up. I was surprised when he stayed silent, gritting his teeth. Even Carlyle could not doubt Tony's commitment now, as he stood there in tight clamps and lace underwear, blindfolded. He had placed himself entirely in my hands.

It made me very, very wet.

I knelt in front of him, running my hands up his strong thighs, my fingers dancing toward his lace covered shaft. I looked up, the nipple clamps still tightly in place. He hadn't lost his erection, nor given into his safe word, so I was going to reward him. Behind me, I heard Carlyle sit down, heard the soft unzipping of his trousers.

The tip of Tony's big cock poked out of the panties, so of course I had to start there. I flattened my tongue against it, teasing, salivating. His salty goodness hit me and and gave a little moan, swirling my tongue around it, tracing the tip, the delicious little edge.

I was able to quiet myself to a whimper, but the pain kept me on edge, quivering. I felt Madame touch my thighs, fingertips on either side of my cock. I thought she was going to pinch it next and I prepared myself for that.

It was her tongue that tormented me next, licking my cockhead and giving me such sweet pleasure. My cock throbbed and my precum bubble up even more. The sensations of intense pleasure on top of intense pain was maddening.

I didn't think I could take much more of this. I wanted to scream at the pain and cum with pleasure. But I didn't know which was Madame's goal for me, and that was the real torture.

I looked up at Tony, my view from my knees very pleasing, the long expanse of his smooth chest and the clamps keeping his nipples red and hard. I popped the tip of his cock out of my mouth and cupped his balls with one hand.

I looked behind me. Carlyle took his cock out of his pants, his legs spreading wide on the chair. His eyes were fixed on me as he began to stroke.

I shimmied Tony's little lace panties halfway down, licking newly exposed shaft. His veins throbbed, the elastic of the panties hitting his cock in the middle, still trapped. I sucked the precum that oozed out of him.

"My master is here, Tony. Watching you. Watching me."

I heard Madame confirm what I'd surmised, that Carlyle was observing tonight's session.

I replied with a moan, not trusting that I could speak well in my current state of pain. I knew that my response to Madame's discipline tonight, my every move, my every sound, was being judged by Madame's Master. He was probably judging her more critically than me. She was his protégé; she had a higher standard to meet. Still it was my submission that would best validate her dominance of me.

So as Madame sucked my now steadily pulsing precum, I called on every last ounce of my will to hold back any premature ejaculation or uncalled for verbal response. I was committed to perform exactly as Madame told me to act.

"Quiet boy," Carlyle said from behind me as I hovered at Tony's crotch. His deep voice reverberated across the marble floor. "Very good. He doesn't speak unless you tell him to do so."

I licked the visible part of Tony's cock, over and over, slowly. My hands wandered up to his ass, still half-covered with lace, a finger tracing in the crack. I tried to ignore Carlyle's assessing; I knew he was encouraging Tony and I without trying to intrude. I grazed my teeth over the tip of Tony's cock.

"You may tell us how you feel," I said, my breath hot on his throbbing manhood.

Madame's teeth scraped lightly over my swollen glans, teasing the bubbling slit at the tip, and making me shudder. She said, "You may tell us how you feel."

I took a deep breath to answer. The rising of my chest brought another shock of pain to my nipples. I steadied myself and spoke. "I'm surprised by the way I feel. The pain is terrible and I should hate it. But I can't, because I agreed to submit to what you want for me. I really enjoy what you're doing to my cock. Overall, I feel amazing."

I had said a lot, hopefully not too much.

"Very good, Anthony."

I could tell it unnerved him when I used his full name, so I did so to keep him off balance while I pulled the lace panties down to his feet. His cock sprang free and hit me in the face. I gave it one long lick.

Behind me, Carlyle gave his cock a few more good pumps before shedding his pants altogether. I could hear him approach softly, just as I took Tony's cock fully in my mouth.

My cheeks were filled with his hardness, his taste. I could tell he had been close to cumming all this time, but held back. Good boy, I thought, but did not say aloud.