by Ruby Madden
I’d been judicious in the way I’d handled contract negotiation with Ethan and his attorney. Unlike my other clients, where there was no sexual intercourse, just domination on my part, over them – I’d switched up my usual agreement and contract.
I’d tailored the one between Ethan and I so that we could be mutually, sexually intimate with one another, and satisfied.
He may not have realized it, but I’d already revealed my end-game to him. I was counting on his lack of experience to allow this gift, this bow tied at the end of our arrangement, to hopefully be the momentous gesture it truly was.
I’d also included a clause that allowed either one of us to nullify the agreement, our arrangement at any time. It included a fourteen day ‘suspension’ period of time so that neither of us would make too hasty a decision, but once invoked – it was to be honored and the contract would be dissolved.
I’d done this as I had realized something very simple about Ethan the moment I’d met him for our initial consultation. He was exactly the man I had been looking for – to fall in love with. In all my years on the planet, I’d yet to have this most desired of all experiences and I wanted it.
I wanted it badly.
Ethan was a vexing combination of Scottish and Native American heritage. At six feet, two inches, he was just the right height for my liking. He had a lithe, sculpted body and a deliciously shy and sexy persona.
A lover of books, cinema and art, I knew we had a lot in common in terms of what we appreciated. The type of lives we cultivated. He’d attended Stanford where he’d created a web-tool that was essential in the every-day world of eCommerce. At the tender age of thirty, he’d sold his proprietary interest to one of the tech giants and spent his time finding other budding projects to invest his money into.
He was humble and never bragged about his wealth or intelligence. His intelligence, his shy and gentle disposition were immensely attractive to me, as attractive as his beautiful, sexy body.
He may not have realized it, but for me – he was the complete package.
And now, here he was kneeling before me with an erection that I wanted to use and abuse, unabashedly. I sucked in my own deep breath of air to gain control over my senses. It was of the most utmost importance that I remain in scene during this, our first session.
He needed someone like me, a woman who intimately understands her innate power, erotic or otherwise. I respected his needs. His wants. His desires. Perhaps, by appearances, to those who don’t understand the erotic power exchange of a Mistress-slave/sub relationship, I may not treat him as if I respected him. However, any good Mistress knows – our submissive’s needs are more important than our own in certain ways. We’ve been gifted with the privilege of guiding them on their own journey of self-discovery and service, tailored to their unique self.
The key? Allowing them to submit, worship, beg and suffer.
Much of the satisfaction we achieve is about the inherent beauty and truth of being in command, of the power-play in the psyche, of how our minds like to trick us into denying our biological imperatives and physiological wiring. For men, this is especially so – in a world and society that seemingly denies them nothing. The very experience they crave is to be denied. Then to a phase of acceptance and becoming that creates the erotic freedom so vigorously sought.
Complete disempowerment. True submission.
Ethan was learning fast and I could tell by the tone of his voice that he was sincere in what he said. My affection for him was already endearing.
This meant I needed to be inordinately mindful of the ‘basics’. I dutifully pushed aside my own needs, wants and desires – as ironic as that may seem and remembered that we still had many sessions ahead of us in firmly entrenching the basics of male submission. Ethan’s training had begun the moment he’d stepped into the lobby of my condo high-rise.
* * *
“Do you like my toe cleavage, Ethan?” I wiggled my foot in my expensive footwear a bit and watched him suck a deep breath in.
“Yes, very much so Mistress.”
“Would you like to lick my shoe, Ethan?”
He didn’t even hesitate or answer but immediately lowered his face to my shoe and began to lick, one long elegantly done lick. As if waiting for me, he paused – suspended in place.
“Please do go on Ethan, lick my shoe. Lick it as if it’s my foot, my skin.”
He did, with a sweetness of blossoming devotion that stirred me. His face was so beautiful, so sexy – not to mention his hidden erection that was peeking up at me.
I allowed the shoe to fall to floor with a clang. “Lick my foot and toes…”
He lapped at my soft, petite feet and when his tongue darted between my primary big toe and the toe next to it, I had to keep from squealing, it felt so luscious. A zip of energy went coursing through me. He eventually got around to suckling each of my toes and was ever so tender.
And then I saw it, the first look of adoration on his face, that first glow of being allowed to worship. He was already there, barely into our session, minus the time I’d made him wait in the lobby.
So much for ensuring he was naked and vulnerable at the start of our session. I’d have to maneuver this a bit differently to get it back on track.
“Unzip your pants Ethan, pull out your cock for me.”
I watched him as he nervously fumbled with first his jean’s top button and then the zipper to pull out his erection through his boxer briefs. I extended my foot groping his groin and cock, allowing the bottom of my foot to glide along the length of his shaft.
I always got a secret thrill from the contradiction of a man’s sex – how it felt to the touch. So soft, so hard. Warm and pulsing or twitching. Velvety even. I teased his cock-head with my big toe, circling the base. I felt some of the droplets of his pre-cum dribble down between my toe cleavage.
“Lick and suck your pre-cum from my toes, Ethan.”
He did and I could tell this only aroused him further. I was loving this man, more and more. He suckled me deliciously.
Oh the many places you will get to suckle, sweet, sweet Ethan…
Without giving him any warning, I pulled my foot out of his mouth and stood up. The clock was ticking and I needed to move forward with the session.
“Ethan, I need you to go into the bathroom through that door, strip, take a five minute shower to clean yourself, and then come back to this kneeling spot, in the nude. You may NOT touch your cock or arouse yourself. You may NOT come. Do you understand?” I stood and pointed to where he was to go.
“Yes, Mistress.” He got up immediately and did so.
My first test was underway.
He went into the bathroom. I stepped into my den, where I would watch, unbeknownst to him, while he showered, from a hidden camera. I would know whether he had obeyed me or not. This would determine how the rest of the session would go. While he showered, I kept a watchful eye on the computer screen. Observing him, I began to change into my next outfit.
As I changed, I watched him lather up his sexy body. About halfway through the shower, I saw his hand start to wander and touch his cock. Just as quickly, he pulled it away and thumped his hand against the wall in a fist. I grinned and felt my own arousal as I now had the justified pleasure of abusing his ass. Just the thought of putting a ball gag on him, my welt marks on his ass, making him squirm and then milking him, was making me wet.
Get a grip Cherry!
Beneath the dress I’d just taken off, I was already geared for our session. An expensive and tight corset pushed up my size D tits, wonderfully containing my buxom, curvaceous body. My signatures were my cherry-red lips, my enhanced red hair, my cherry-red manicured nails and the cherry-red laces of my corset.
The rest of me was complimented by a barely-there thong. I zipped up a pair of thousand dollar, thigh-high, cherry-red, Italian leather, high-heeled boots. Part of the art in being a Femme-Domme was deciding what skin and parts
of my body a puppy-slave most desired to touch and then denying that privilege with a layer of sexy clothing and gear. This simple barrier would then be taken off in due time to become a reward, in and of itself, as I saw fit.
When I came out of my den, somewhat pleased that I’d have good reason to make use of my favorite riding crop, he was butt-ass naked, trembling a bit and kneeling – just as I’d asked him to. I came up from behind him allowing him to hear and sense my presence first before I made our first contact. I trailed the tip of my crop along the contour of his shoulder.
He shivered.
When I arrived in front of him, peering down at him, he was still erect. His cock was gorgeous.
Good boy…
“Ethan, did you obey your Mistress while you were in the shower?”
He faltered, I knew he was trying to figure out what to say.
“Mistress, I failed you. I touched myself momentarily and then remembered I had been told not to. I’m sorry…”
I was immensely pleased. He’d been completely honest as that was exactly what had happened. I’d witnessed it on the computer monitor myself.
“Ethan, in this exchange – you’ve agreed to punishment when you disobey me. We agreed to explore the ways in which I choose to punish you. Do you understand?”
He double-gulped. I could see that his pulse was raising. “Yes, Mistress. I understand.”
“Good.” I said.
I moved a bit further away as I wanted to afford him the momentary opportunity to see me in full uniform, to allow his arousal to continue.
It did, his eyes were glued to my body.
“Ethan, there are going to be times when what I seek to teach you won’t make sense at first, but it’s your trust that I’m earning. Your trust is very important to me. Because of that, we’ve agreed to certain words and movements so that you can express when you’re feeling unsafe or would like to discuss what is occurring. I will never disrespect you when you use these phrases and words. I will stop whatever I’m doing immediately if you indicate you are in true distress. This is very important. Do you understand?”
“Yes, Mistress. I understand.” He said.
“Good. I will use a ball-gag on you today. Do you remember the movement you are to use if you need me to stop?” I asked.
“Yes, Mistress – I remember.” He answered.
“Ethan, demonstrate the movements so we can both be sure.” I said.
He did so, in the order he had been shown. I was pleased.
“Ethan, you may position yourself so that you are lying on that ottoman, on your belly, your legs slightly spread.” I used my crop to point to the luxurious cherry red velvet ottoman that I was to punish him on.
He immediately stood and did as he was told. Once he was half-lying on the ottoman, his torso over the top if it and his ass just hanging over the edge, his gorgeous and still erect cock was pushed down towards the floor, his sweet ass dangling there for me. This position forced him to still be semi-kneeling, but somewhat supported for the lashings that would come. I couldn’t wait to mark it and make it red. I couldn’t wait to have a session when I could torment his scrotum and his cock.
Be patient Cherry, in good time…
{ ethan }
I couldn’t believe I’d already failed her.
She was unbelievably sexy in her Dominatrix outfit. Her plump curves were contoured seductively by tight leather. She’d replaced her sexy, toe-cleavage revealing, cherry-red shoes with a pair of thigh-high, leather boots that made her look and feel even more-so the commanding goddess she truly is. She held a riding crop in her hand as natural as if it was a purse, not an implement of punishment and pain.
I was both mortified and thrilled.
Equally terrified of the inevitable sting that I knew was coming. My fascination between being punished and who would punish me was just about the best mind-fuck I’d yet had. It was so simple. She’d given me the simplest task, the smallest ten minutes of momentary freedom and I’d already disobeyed her. This was exhilarating, it truly was.
I wanted her to inflict pain on me.
To feel shame.
To remain aroused by her, I’d never had an erection last this long or remain so hard in all my life.
Cherry Stuart is my Mistress.
I said it to myself, gleefully, in my mind.
She stepped in front of me and in the most practiced, skilled move ever – fitted a ball-gag on me.
“This will sting, Ethan and although my suite is mostly sound-proofed, I enjoy controlling my puppy-slaves’ sounds.”
Puppy-slave…
She then pulled my arms forward and directly in front of me, I realized that there were leather restraints that looped perfectly to a wooden post. She wrapped each one around my wrists, ensuring a snug fit and then pushed the ottoman back a bit so that my body was extended and stretched out.
My erection was agonizing at this point and its current positioning had me suffering. My legs strained beneath me in the awkwardness of my position. It was as if she had known I wouldn’t be able to completely lay on the ottoman, or otherwise crush and ruin my erection.
It was then that I realized something so elemental. Why she’d reviewed the movements I would need to use to indicate that I wanted her to stop. How could I ever say a safe word? It seemed she preferred to use ball-gags…
Having my voice taken away from me exhilarated me.
Her gloved hand touched my bare ass and I practically lurched. I hadn’t realized how tense and wound up I was until she touched me.
“Now, now Ethan… Let me at least warm you up a bit. You’ll be thankful that I did.” She said.
She continued to rub and massage my ass, creating a bit of friction beneath her touch. When she seemed satisfied, she executed her fist skilled strike.
God damn!
It hurt like all hell, the sting of it lingering. She came down quick with another strike, equally executed just as strategically on the other side. She didn’t waste time and before I knew it, I was grateful for the restraints.
I would have gotten up and ran from her, I’m sure of it.
The impulse of the body to physically run away overwhelmed me. With each strike, I truly doubted my ability to handle another one, but before I was even able to complete the thought, I was feeling the professional sting of another expertly executed strike. She delivered what felt like a hundred. In truth, it was around twenty.
Tears were pouring from my eyes along with my muffled moans of agony. This hurt like hell.
What was I thinking?
And then she did it, she paused and delicately stroked my scrotum with the tip of her crop. Pain and arousal fused together into some semblance of erotic insanity. I suddenly reveled in how vulnerable and exposed I was to her, in this position. That if she wanted to, she could strike my balls or my cock at any moment. She trailed the riding crop from my scrotum up to my anus where she teased its opening.
Then I felt a gloved finger, thankfully lubed, enter my ass.
Again, glad for the restraints.
Nothing had ever been near my ass and it had never been penetrated by anything or anyone but my physician for my annual exam.
“Have you ever had your prostate massaged, puppy?” She asked.
I’m not quite sure how I managed it, but I gasped out a mangled ‘no’ through the ball-gag, shaking my head back and forth, just in case.
“It’s an odd sensation at first, simply for the fact that you’re unacquainted with this sort of penetration. It’s important to relax and breathe. Eventually, you will grow to like this… and request it even.” She explained.
I lolled my head and realized that to an extent, I’d been clenching my ass-cheeks. I relaxed them.
“Thatta boy…” She purred, massaging and probing gently.
With one gloved finger in my ass, and applying a pleasing pressure, she then stroked my erect cock with her other hand. Not
that I could see any of this, but I didn’t need to it. It felt so delicious.
“Ethan, your Mistress loves your cock, it’s beautiful…” She shared.
I didn’t know what to say or do as I was muffled, but secretly thrilled to hear her say so. I whimpered a bit and this seemed to please her.
“Whimper some more for me, Ethan. Beg for it. Would you like your Mistress to stroke you to completion?” She asked.
And right then and there, I did something I thought I’d never do. I whimpered and begged, just like a puppy.
Like a god-damned dog.
Anything to have some release. Her hand felt divine on my aching balls and firm cock. And though I was somewhat loathe to admit it, inside my ass.
Despite my doubts about the awkward positioning of my cock and the painful stings of pain that were still burning the flesh of my ass from her riding crop, she milked an eager come out of me that felt like a volcano had descended into my loins. When I came, I thought I was going to break free from my restraints. Restraints that I was now grateful for, as there was something so wonderful about being limited and confined.
She stepped in front of me, a look of satisfaction on her sexy face. She crouched and showed me her open-palmed, gloved hands. She’d collected my come. She managed to take off my ball-gag and with one word, one command – she made me do something I’d never done before.
“Lick.” She commanded.
I licked my come completely off of her gloved hands as quickly as I could. She seemed pleased, a smug grin of satisfaction on her gorgeous face.
“You’re a quick study, Ethan. Mistress Cherry likes playing with her new puppy.” She said as she literally, petted me on the head and scratched a bit behind my ears. “You took your punishment AND reward, most excellently.”
She unfastened the restraints and walked away, as casually and calm as a cat. “You may leave whenever you have collected yourself enough to do so. Your task until our next session is that you are not allowed to masturbate, watch any porn or receive any type of sexual pleasure from anyone else. This will be the last week your cock is free. Next time we meet, I will be caging that gorgeous cock of yours. Do you understand, Ethan?” She asked.
