An Oral Contract

[VixenEV]

I ran the back of his my hand down his cheek.

"Bend over the desk."

I watched as he obeyed, wondering if my own Master was peering through the peekhole. He could be at any time, I knew. I could not let the infraction slide just because some college kid was making me feel a little mooney, with his doe eyes and eagerness to please.

 

[Ambisextrous]

I stepped closer to the desk and leaned forward. I let my chest and shoulders rest on the polished oak top, turning my face to the side. The position was uncomfortable and I knew that was part of the punishment. I opened my mouth to breathe deeply, but I kept quiet about it.

And I waited for Madame to deliver the first blow.

 

[VixenEV]

I crossed to the bookshelf, opening the safe beside it, filled with a dazzling selection of gear. Best to start small, break him in...and he was so willing, there was no need to rush. I chose a small riding crop, leather, with a wide fan. I walked around to the side of the desk, so Tony could see his fate.

I smiled wickedly, lips still swelled from our kiss, and slapped the crop on the desk, not too far from his head. It made a loud sound in the silence of the room.

 

[Ambisextrous]

After a short wait, I saw Madame appear at the side of the desk, holding a leather riding crop. I gasped and I'm sure my eyes registered some fear. I had assumed my spanking would be by Madame's hand. But now I had my first inkling of what her cruelty might be.

Madame slammed the crop onto the desktop inches from my face. The loud snap shocked me. I knew this was going to hurt, really hurt. I hoped I would not need to use my safe word on my very first test.

 

[VixenEV]

I saw Tony's eyes widen with shock and a thrill ran through me. Now I knew what Carlyle felt like--the power and responsibility of having another person give into your will completely. I looked at the antique clock standing in one corner of my office. An hour had passed. Enough time left for discipline and orgasms. I leaned down, petting Tony's head to calm him, then placed myself at his back.

I leisurely ran my hands over his pert ass again, taking my time to feel all the delicious curves through the flimsy white boxers, then placed the crop on his left cheek. After a few whacks, those boxers would certainly have to come off. I hesitated, waiting before bringing the crop down. I didn't want him to know when it was coming. A few loaded moments passed; I could hear him breathe.

 

[Ambisextrous]

Madame patted the top of my head tenderly then stepped around behind me, running her hand over my butt. She massaged my backside firmly for a few moments, rubbing my boxers against the skin and stimulating blood flow. Her fingers tugged at the boxers for a bit, I supposed to remove my one remaining garment; instead she tucked the back seam into my asscrack, stretching the fabric snugly over my round cheeks.

Madame removed her hand and it was immediately replaced by the crop. She rested it gently on my left cheek for a long time, letting me feel its slender substance and consider how it might feel in action. Through the anxious seconds of waiting and considering, I forced myself to breathe deeply.

Suddenly, the crop lifted from my cheek and returned to it with a speedy snap. The force was shocking and painful. I groaned and felt tears gathering in my eyes.

 

[VixenEV]

The first snap resounded through the room and I smiled at his groan, which was half pain, half pleasure. I delivered another slap of the crop to his right cheek--I've always been fond of symmetry. In a momentary pause, I laid the crop on the desk and curled on top of him, my breasts pressing into his back, the wetness of the open panties seeping into his boxers. I leaned to whisper into his ear.

"How many do you think you deserve, Anthony?"

 

[Ambisextrous]

I liked the way her body pressed against me, even with the sting on my butt. I could have said I'd had enough already, but I felt neither of us would be satisfied with only two swats.

"You know best, Madame. Will you still be reminded tomorrow of how I embarrassed you tonight? Maybe I should be reminded tomorrow and feel the sting when I sit down. Make the punishment fit the crime. I trust you Madame."

 

[VixenEV]

"For someone who knew nothing of domination before today, you are a very quick study."

I smiled, shimmying down his boxers, careful not to pin his cock anywhere too uncomfortable.

"Therefore I'll only make it slightly sting when you sit down at the office tomorrow. Just so I am never too far from your mind."

I pulled back, winging the crop through the air, harder than before. Once, then twice, on each cheek. I watched his skin spring against the crop and redness started to bloom.

 

[Ambisextrous]

Madame slid off my back and pulled my boxers down to my knees. The abrupt exposure to slightly cooler air did nothing to relieve the heat I already felt in my asscheeks. Without another word, Madame delivered two more crisp swats on each cheek. Each swat seemed more forceful and painful than the previous.

My breathing was reduced to shudders and my tense leg muscles quivered. I knew I would definitely remember pain tomorrow, if I would even be able to sit down on my burning ass. I didn't want to admit it, but I would be satisfied if Madame was finished now.

 

[VixenEV]

I could hear the change in his breath, the tenseness of the taut muscles in his shoulders. He had had enough. One more for good measure, a test of his dedication. I made this one a little softer, but aimed it between both cheeks. They quivered with the motion.

I noticed my nipples were quite hard.

"Turn around, Tony."

 

[Ambisextrous]

Madame gave another swat that stung into my crack. It felt lighter, so I hope that was the final one. Then I heard her say "Turn around Tony" and I knew she was finished.

I stood up slowly, feeling real pain in my tense glutes. Before I turned to face Madame, I blinked my eyes to clear the tears. After I turned and saw how noticeably aroused she looked, I had to smile.

"Thank you Madame."

 

[VixenEV]

I maintained a bit of distance from Tony, only leaning into his naked body for enough time to untie his hands. I knew his wrists had to be aching at this point and sure enough, there were little bands of red from the friction.

I looped the tie around my own neck, fabric hanging between the swell of my breasts. For the first time, I saw his cock, still half-hard, but somewhat tamed by the pain.

"You're welcome, dear boy."

 

[Ambisextrous]

After Madame untied my hands, I rubbed my wrists to get the blood flowing in them. I hoped the slight chafing of the skin would fade before morning, or I'd have some explaining to do. I wondered what mom and Miss Judy would say if they knew what I was up to.

My smile grew bigger as I feasted my eyes on Madame's charms. What did she have next for tonight? And tomorrow and after that? I was getting more excited at the wondering and my cock was getting stiffer.

 

[VixenEV]

I watched his grin widen as he got hard again, my hand wandering down to grasp his shaft, smooth and tightening every second.

"You did well taking your punishment. How do you feel now? Answer well and I'll let you cum. After me, of course."

 

[Ambisextrous]

"Thank you Madame. Well aside from the physical pain, I feel good about the experience. I'm happy to be here, happy to be in this position. And you've got me so damn hot I'm not going to hold off cumming much longer."

 

[VixenEV]

I wound my arms around him, pressing my wetness in his hardness, and kissed him again. When I pulled back, my pussy was throbbing, soaked and in need.

"I know I said we wouldn't be fucking the first day, but we both need to cum...and I want you in me."

I glanced over at the settee, which was large enough for the purpose.

"Are you up to the task, Tony?"

 

[Ambisextrous]

"I've been up since I got here Madame. I'm not prepared to sit right now, but I think I can give a good poking. And your pleasure Madame is not what I think of as a task."

I did hope my stiff cock would make up for any stiffness I felt in my glutes.

 

[VixenEV]

I looked to my side, seeing Carlyle's eyes through the peek hole. Gray steel, staring. I looked back at Tony, grasping his shaft fully in my hand and stroking languidly. With my other hand, I pulled down one cup of my bra, letting my luscious breast spill out.

"You may put your mouth on me."

 

[Ambisextrous]

I didn't waste another second, but leaned down to take her erect nipple between my lips. I heard Madame gasp as I sucked and licked it fervently. Her breast more than filled my mouth, but I took as much into my mouth as I could, slobbering over it joyously.

Madame jacked my cock shrewdly, just enough to keep my pre-cum bubbling steadily. I had cum much too quickly this afternoon. I was not going to let that happen again.

 

[VixenEV]

I watched avidly as Tony licked and sucked, making my body sing with need. I knew I should withhold this first time, but being in control had turned me on too much. I wanted the thick, long cock I was now stroking deep inside me. And since I was the boss, I was going to get it.

I took my hand away and gently moved Tony's mouth from my breast. His lips shined and his shaft jutted, an arrow pointing at me. I moved back against the desk, discarding my bra as I went, perfect globes now free to the air.

I arranged myself on the edge of the desk, elbows holding my body up, and spread my legs. My pussy was smooth and wet, the lips parting to receive.

"Fuck me slowly, Tony, and talk dirty. Your Madame likes to hear all your nasty thoughts."

 

[Ambisextrous]

“Forgive me Madame,” I said, ripping her silk panties off, “but these have to go. I want full access to every inch of you. Your pretty titties.” I bent down to kiss first one nipple then the other.

“Your luscious lips.” I straightened up to bite her lower lip playfully and slide my cock snugly beneath her crotch.

“Your wet, wet pussy.” I ground my pubes against her splayed labia.

“Even your little butt hole.” I flexed backward, dragging my cock head along her spread ass crack. “Would you like that, Madame?”

“You want my cock in you, Madame? Which hole should I start with? And which hole should I finish in?”

 

[VixenEV]

I was very pleased with his boldness, which showed on my face and in the rush of new wetness that soaked his grinding cock.

"Mm, you've been a good boy...but not good enough yet to earn access to my ass."

I lifted my hips a little, pressing him into me partially.

"And tomorrow you'll have to make up for ripping my panties."

 

[Ambisextrous]

“If I must Madame, but perhaps I can change your mind.”

I grabbed my shaft and traced the drooling tip up one pussy petal then circled around her clitoris for a moment.

“Do you like to butt heads?” I slid my wet glans over her emergent clit. She responded with the slightest of shudders. “I think you do. You like clitty play, don’t you? ”

I directed my glans back down and stirred it between her glistening pink pussy petals where my mouth had so recently played.

“Pussy’s so wet and ready to fuck.” I nudged in a bit. “You said to go slow?” That was a challenge; she was so wet I slipped half way in before I could stop. “Damn tight cunt.”

I plunged in to the hilt, causing Madame to groan. She was tight as a virgin and hot as a whore.

“Your Master must not tap this much. Does he know we’re fucking?”

Her pussy shuddered at that question. She was no longer in control and I was going to take advantage of that. I withdrew slowly, my cock head tugging at her pussy walls, and stroking her engorged g-spot. She gasped.

“Oh you like that don’t you? Well that how I’m gonna fuck ya,” I thrust back in balls deep, “fuck ya hard and make ya cum like slut.”

I gave it my very best too. I had surveyed the contours of Madame’s pussy; I knew where her hot buttons were. For the next few minutes I was in control. I fucked her slowly, thrusting balls deep, grinding into her clit and g-spot, pulling out and thrusting in again. Over and over again. Gradually increasing the pace. Fucking harder. Balls slapping her ass.

I wasn’t close to cumming yet; I wasn’t worried about tomorrow. I thought only about pleasuring this sexy woman, and giving her an epic orgasm.

 

[VixenEV]

My eyes widened and my mind whirled. Each question Tony posed, dirty and rhetorical, went unanswered. I could not have spoken if I tried, my mouth was so filled with moans.

I was not supposed to be letting him fuck me, and he seemed to know it. Carlyle's eyes steamed through the peephole, but he did not interrupt. I was going to be in trouble myself, for losing control of the situation, for being greedy. I couldn't care at the moment, because Tony was plucking every string in my body, knowing just where to touch and thrust. It was dizzying and I rocked with the force of it, just barely keeping my ass on the desk. When he hissed that he was going to make me cum like a slut, it sent me over the edge. I did exactly as he said, completely losing my dominant demeanor. I was his, for 30 long seconds, an orgasm that stuttered around his cock, my pussy muscles convulsing wildly. I actually moaned his name. One hot syllable, "Tony," like a curse or a prayer.

That would get me into trouble, too. I saw the peephole slam shut.