As for the pleasure he’s given me… hmm, every time I think about it… I bite my lip to stifle the moan that threatens to slip out. I giggle softly. I don’t want the cab driver knowing what’s on my mind but the slightest vibration of the car transfers to the object currently stretching my back passage. It heightens the awareness of my already sensitized throbbing sex.
It’s been days since my last release. On the directions of Mr. Callahan, I have not touched myself, have not made myself cum; the arousal has been building to unknown heights. I’m a tinderbox, ready to self-combust.
Today has been excruciating. Mr. Callahan, seemingly by accident, but probably on purpose, often brushed his hand against my arm, on one occasion even my hip. Also, he’s stood just a bit closer than usual when we’ve been going through documents. In my super sensitive state, I noticed these things and became more and more flustered as the day crept along. It was almost a relief when he left early for a meeting, while I stayed behind to prepare a file on a new client.
The cab runs over a pothole, and I’m again reminded about the object in my ass. As if I needed a reminder! I’ve not been able to stop thinking about it since it was introduced to my body, or what will replace it when Mr. Callahan removes it.
My thoughts wander back to yesterday afternoon when Mr. Callahan, out of the blue, told me it was time for my small butt-plug to be exchanged for one of a bigger size. One minute we were discussing possible mergers, the next I was bent over his desk, skirt raised, panties pulled down to my ankles.
He told me to spread my ass-cheeks and hold that position for his perusal.
“Hmm, yes.” The deepening of his voice tone was an indication that he wasn’t as unaffected as he pretended to be.
“Have you been wearing it at all times, as instructed?”
“Yes Sir.”
“Hmm, good girl.”
I smiled at his praise. It made me so happy that he was pleased with me.
Then, I felt his hand at the small of my back, his thumb rubbing small circles, as he grabbed the plug with the other, slowly pulling it out. The sensation was exquisite, so different from the times I’d needed to remove it myself.
“Ahh,” I moaned.
He put the toy on a piece of paper and prepared the bigger plug, covering it with a generous amount of lubrication. Again his hand soothingly rubbed my lower back.
“Now relax. This one is considerably bigger, closer to size of my cock.”
At the word cock, my pussy visibly clenched, and Mr. Callahan chuckled. “What a horny little slut you are; you really long for me to take your ass.”
“Yes Sir. I am Sir.”
I flinched when I felt the cold lube touch my sphincter.
“Shh, you’re doing fine.”
His encouragement helped me to relax again, and he gently pressed the plug against my rosebud. Remembering the instructions from last time, I pushed backwards, opening myself up as much as possible. It was still a stretch, the much bigger plug needed some force to enter. But then my tight muscle gave way, and I felt it filling me.
“Ahh, Sir, gaaah,” I panted through the sensation of it stretching me like nothing before. It ached but, at the same time, I liked it. In fact, I liked it a lot, feeling almost overwhelmed by the sensation of having something that big in my rear passage.
He let me regain my equilibrium before lightly nudging it. My shallow gasps awarded me another chuckle.
“Hmm yes, perfect.”
He bent over me, and I felt his erection against my rump as he whispered in my ear. “Feel that stretching you, preparing you to take my cock.” He emphasized the word cock, elongating it, as if he knew that would make me shiver in anticipation.
“Yes Miss Steel, that’s right. Next time I’ll replace this…” his finger nudged the plug again, making me quiver, “with my cock.”
My answering moan left no illusion to how incredibly arousing I found that thought.
Then he stood, telling me I could let go of my ass-cheeks before giving my rump one hard slap, and that was it. One single smarting smack on my ass and then nothing. Just the instruction to pull up my panties, and get back to work, not even requesting a blowjob, like the one I’d so enjoyed giving him when the smaller butt-plug had been put into place.
When I hesitated, he just looked at me with raised eyebrows and calmly said, “That’ll be all, Miss Steel.”
Disappointed, I walked to the door to leave his office but he called out, almost as an after thought, “And Miss Steel, you are having dinner with me tomorrow night at the Duke. Seven o’clock. Don’t be late.”
I’m jolted back to the present, hearing the driver tell me we have reached my destination. I pay him and head into the Duke, for what I believe might be a life-changing experience.
A hostess shows me to a private dining room Mr. Callahan has booked. Seeing him, I halt, catching my breath. I’m suddenly nervous, not knowing how to behave, now that we’re out of the office. He’s striking in his pinstripe suit, dark hair slicked back, the distinguishing grey at his temples. His sharp grey eyes light up as he looks at me. I’m glad I dressed up for the evening, a black form-fitting cocktail dress hugging every curve. It gives my confidence an extra boost watching his eyes looking me up and down, admiring me.
Mr. Callahan rises from his seat. “Miss Steel, you are absolutely beautiful tonight.”
He holds my hand, kisses my palm. A bolt of electricity runs through me at the light touch.
“Thank you, Sir.”
I exhale. I'm hypnotized by his nearness, drawn to him by his magnetism, his incredible charisma.
With a hand at the small of my back he leads me to a chair, pulling it out for me. He kisses my neck softly before returning to his seat facing mine. His tiny, gentle touches so far have lit my fire and my pussy is salivating for him, a dull aching throb beginning to build. I squirm in my seat, trying to rub some of that ache away.
Mr. Callahan’s smirk shows me that the movement did not go unnoticed. Taking a deep breath, I refocus. If he can pretend to be unaffected so can I.
I look around the small dining room. The walls are painted in a deep rosewood, the floor is covered by a thick charcoal carpet, sconces with lit candles give an ambient light. The table is covered with a linen cloth and set with fine china. It’s really very romantic, in a dark and sensuous way.
A waiter arrives and we order. Through dinner, we talk quietly, the words flowing easily. I realize I’m comfortable in this setting with him, enjoying the meal and his company. Neither of us mention the heated tension building between us, but it’s there, almost a tangible presence in the room. The way Mr. Callahan steers the conversation away from anything alluding to our erotic encounters, has my blood boiling hotter than if he had been crudely flirting with me.
This planned seduction, because that is what it is, a seduction by a master seducer, has me tense with anticipation and, simultaneously, tranquil. I feel safe and yet, it’s like feeling safe with a predator lulling me to let down my guard before the beast strikes.
He seems so sure of himself, so confident, knowing he has me exactly where he wants. I like him this way, how he steers me in his chosen direction, but I’m still baffled by his quiet certainty.
“Sir, if I already had plans for this evening, what would you have done?”
“I would have told you to cancel them.”
The way he says it, as if it’s the natural order of things, makes me smile. I know from working for him for years that, when he has his sights set on a particular goal, he does not back down. And now his sights are set on me. I like that, I like it a lot.
When we’ve been served dessert, a mouthwatering rich chocolate cake, he mentions the butt-plug for the first time, instantly changing the topic and tone of our conversation.
"You are wearing your new butt-plug." It’s not a question, more a statement.
However, I still choose to answer him. "Yes Sir."
"Good."
He hasn’t looked up from his plate, seemingly focused on his cake. He picks up a piece with his fork, puts it in his mouth, savoring the taste before continuing, “Have you touched yourself? Made yourself cum?"
“No Sir. You told me not to.”
At this he looks up smiling. I can see that he is happy with me, with my compliance. Seeing his pleased expression fills me with a calm contented joy, a jubilant feeling making me want to please him further. However, his next request has me on edge.
“Take off your panties.”
“Here? No, I cant. What if someone comes?”
He doesn’t answer, just looks at me with one raised eyebrow. His gaze is forbidding, stern. I know that look: it’s not to be argued with. I sigh in resignation.
Slowly, I raise the hem of my skirt so that I can reach the edge of my lacy underwear. I put my fingers under the hem, raise my bottom slightly and slide the panties down my legs, looking at Mr. Callahan all the time. I put them in the palm of his outstretched hand.
He lifts them to his nose, inhaling deeply before putting them in a pocket of his suit jacket. The act has me squirming in my seat.
"Good girl. How are you feeling?”
“Hot and aching for you, Sir.” My voice is breathy.
“You may touch now, but not cum.”
“Here?”
“Yes. In fact, I would demand it of you, but I don’t think I need to.” He tilts his head to one side, regarding me, while a small but wicked grin plays across his lips. “You secretly want it, want to touch your soft wet petals, right here, knowing the effect it will have on me. How I will get hard for you.”
At that revelation my breath catches. He is right. I’d like that very much. I put my hand between my legs.
“Slowly Miss Steel. Do it with care.”
My fingers trace the inside of my thigh, bit by bit closing the distance to my aching sex. I automatically gasp with sudden pleasure when they reach my mound.
“Softly trace the outside of your labia with your fingers,” Mr. Callahan instructs.
I do as he tells me, even though I’m burning to let them slide through the wetness. I implore him with my eyes, appealing to him to let me go further. But he just sips his wine, taking another bite of chocolate cake before giving me the go ahead.
“Slide your fingers between your wet folds.”
The action has me moaning, closing my eyes.
“Don’t close your eyes Miss Steel. Keep looking at me.” My eyelids snap up at the command in his voice. “Yes, better, I want to see your pleasure.”
So, while my fingers slip and tease through my drenched pussy, I keep looking at him, my gaze locked with his, my mouth slightly open, as my breath becomes shallower with the building pleasure.
His posture is rigid, all his attention centered on me, the cake now forgotten. I see him swallow, lick his parted lips and then notice a movement than can’t be mistaken for anything but what it is: he adjusts himself. He must be hard.
I grip the tablecloth in a fist, biting my lip to stifle a groan. My pleasure is building, heightened by the awareness that I’m affecting him in such a way. I’m so close to the edge, threatening to tip over any second when he speaks a single word with quiet authority.
“Stop.”
I immediately pull my fingers from my pussy.
“Show me how wet you are.”
Timidly, I raise my hand, showing him my sticky fingers. He groans before leaning over the table, grabbing my hand and licking my fingers. He closes his eyes for a short moment, obviously relishing my taste. When he opens them again they are dark stormy wells of carnal lust.
“Come. It's time." His voice is coarser, darker than usual.
“Time for what?”
The only answer I get is a devilish grin. My stomach flips as he confirms my suspicion; it’s time for that, for him to claim new territory, to take what no other man has taken. I’m suddenly tense, scared and yet eager.
Mr. Callahan stalks around the table and pulls me to my feet, staring down on me with that voracious gaze. He grasps my hand and leads me from the dining room. He’s all but pulling me through the restaurant, exiting through a different door than the one I’d entered.
“Shouldn’t we stay and pay?” I ask. I’m flustered by his apparent urgency. He’s gone from aloof teasing to ferocious urgency in nano-seconds. And I’m just trying to keep up with him.
“What?” He sounds impatient, irritated even, at my question.
“We left the restaurant without paying.”
“Of course not, all cost will be charged to the room.” He says it like it’s the most obvious thing in the world, making me feel stupid for not understanding the simplest facts.
“What room?” Now I’m irritated as well.
Something in my tone must have jolted him out of whatever mindset he was locked in, because he stops to look at me, really look at me. Then his features soften.
“I’m sorry, Miss Steel. I forgot my manners for a minute,” he says tenderly, stroking my cheek. “You are such gift to be treasured and I treat you like a harlot at a beer bash.”
I lean into his palm, delighted by his gentle touch and can’t help giggling at his words.
“Oh, my beautiful Miss Steel. If you knew the effect you had on me, you would praise me for my endurance.”
He pulls me into his arms. I feel his erection poking my stomach. It does funny things to me, makes me forget that we’re in public, and I grind my hips against him.
“I guess I’m not the only one affected,” he chuckles. Embarrassed by my behavior, I blush, try to pull away from him, but he holds me fast, whispering in my ear. “I am dying to fuck you, burning not only to once again claim that gorgeous cunt of yours, but also that tight virgin ass.”
A shiver runs through me. My drenched pussy clenches, and I feel the gush of added wetness coating the insides of my thighs. In my ass, the butt-plug feels like a welcome intrusion, making my rear passage throb in anticipation of the cock soon to replace it.
Contrary to his coarse language, he kisses my forehead with profound gentleness, before letting go of me. I now notice that we are in a hotel lobby and, all at once, his previous comment about a room makes perfect sense. I blush again at my stupidity.
Where was I thinking he would fuck me? At the restaurant restroom? In the parking garage?
Mr. Callahan leads me through the delicately furnished lobby towards an elevator. We’re not the only people entering when the doors slide open. At this hour, the hotel seems busy. After pressing the button for the twelfth floor, Mr. Callahan positions us in the back, the others filing in to stand in front of us.
We seem to stop at every floor, letting someone on or off. It’s slow going.
Halfway up, Mr. Callahan pulls me closer to him, as if creating more space for a group of young women. But his hand moves to the base of my spine, slowly sliding further down, over the curves of my ass, stopping level with the butt-plug. I gasp as his fingers lightly touch it through the fabric of my dress, sending small vibrations traveling along the toy to deep within me.
I pant and bite my lip to prevent from moaning out loud. I lean in to him, the back of my head resting on his shoulder, my legs suddenly struggling to keep me upright.
His mouth at my ear, he whispers salacious promises of what’s to come. “First I’m going to undress you, to see you in your naked glory.” His free hand is brushing over my arm, making goose bumps appear. “Then I’m going to fuck…” his erection presses into my rump, “your dripping wet cunt. Ah yes, I can smell your arousal from here you little whore, a slut so hungry for this.”
Again he thrusts against me, making very clear what he is referring to.
My insides tremble at his words; I’m almost at breaking point.
“I’m going to give you so much pleasure that you will loose that brilliant mind of yours, becoming only the wanton creature I know resides inside you. I’m not going to let you cum until you are begging me to fuck…” slowly he increases the pressure on the plug, ”your ass.” The last word is said with a hissing deep groan, as if he can hardly contain himself anymore than I can.