Mistress Madeline's Play Date

It was a cool, violet evening in late September. The glow from the fireplace lit the living room in a feverish crimson glow as the branches from the old oak tree delicately brushed their tips over the front window. I sipped my wine slowly, relishing its tangy flavor.

At precisely 9:30 pm, the doorbell chimed. A deliberate smile played across my lips as I rose to greet my guest, pleased at his punctuality.

I opened the front door and there he stood, impeccably groomed as usual, with his dark hair neatly styled, pale face smoothly and freshly shaven, and smelling lightly of Burberry for men, the cologne he knew I especially enjoyed on him. In his arms he held a large rectangular box, elegantly wrapped in blue paper with a silver bow fixed to it.

"Good evening, Mistress Madeline," he warmly offered, grinning cheerfully.

"Yes it is, dear Ethan. Do come inside, " I held the door open, stepping to the side to let him by.

Ethan is one of my favorite playmates. He and I have been engaging in D/s games for nearly two years now. He lives out of town, but makes it a point to visit at least once a month. An intense and affectionate man in his mid-forties, Ethan came late into his submissivehood and I have been more than delighted to show him the ropes, (pun intended!).

Once in the foyer, he removed his black wool coat and I hung it in a nearby hall closet. Ethan was dressed semi-casually, in a pair of black trousers and a light blue-grey button down shirt made of hand woven silk.

He leaned forward to place a delicate kiss on my cheek. Our relationship, while always cordial, is one I feel most at ease with, as Ethan has proven to be an exceptionally trustworthy and loyal sub to me.

"I can't tell you how wonderful it is to see you, Mistress Madeline, " he spoke softly. "For you, my darling." He placed the gift box in my hands.

"How thoughtful you are, sweet Ethan, " I mused as I held the box. "Come, let's sit by the fire."

Before making himself comfortable, Ethan paused at the table to retrieve the bottle of wine I had set there and came to the couch where I sat and offered to refill my glass.

"Just halfway, please, " I instructed and he obeyed diligently.

I began to unwrap the box, wondering what surprise it contained. This particular play-thing of mine was a most generous man and his gifts were always tasteful and considerate. Once the wrapping paper was torn, I could see the Nieman Marcus logo on the top of the box. I grinned happily as I lifted the lid and its contents were revealed: a stylish pair of cola-colored calf-skin suede boots with 4 inch heels. Amongst his various kinks, Ethan was a foot-fetishist through and through...

"These are quite impressive," I smiled at Ethan, as he sat expectantly across from me in an overstuffed chair.

"I saw them and immediately thought of you, " he said coyly.

"They will be put to good use, I promise, " I assured him.

For the next 20 minutes or so, we chatted and caught up with one another. Ethan told me the latest news about his family, work and such. I listened intently, as he was a marvelous conversationalist and I appreciated his notable intelligence. I also liked for him to tell me about any transgressions he may have committed in the weeks leading up to our session. It turns out, my dear Ethan hired a young pretty secretary for his company last week. His eyes gleamed while he described her long, supple legs and the cute shoes she often wore to the office. Poor little Ethan is having a most difficult time keeping from becoming aroused in her presence!

After our chit-chat, I told Ethan it was time to begin our "play date". I led him downstairs to the play room/dungeon, in my large, remodeled basement. Ethan was always a bit awestruck when he first entered the play room and I loved watching his doe-like eyes scan the room, his mind spinning as he wondered what the night had in store for him. I giggled softly to myself, as tonight would be a particularly special night for my boy toy!

Once in the dungeon, I removed my lilac kimono to reveal my outfit to Ethan. Tonight I wore a black leather corset with black fishnet thigh high stockings affixed to the rings that dangled from my hips. I wore no panties, and I reveled in knowing how aroused the sight of my smooth, bare pussy lips made Ethan. He sucked his breath in quickly before lowering his eyes to the ground.

"Strip, " I ordered him.

Once he had removed all of his clothing he remained standing in the center of the floor, head bowed and arms to his sides. I turned the overhead lights off and shone a single spotlight on Ethan. I then made my way to where he stood and began my inspection of his person.

"Arms behind the head, legs spread" I instructed in a stern tone as I circled him.

Ethan was a man of slight build, only about 5 feet 8. He was especially self conscious about the size of his penis, which by any standard was on the small side, barely measuring more than 5 inches when fully erect. It was a favorite game of mine to mock his tiny member during our sessions and this verbal humiliation excited him greatly.

"Very nice, you remembered to shave your pubic hair. Now, bend over, " I commanded Ethan.

This act was particularly humiliating for him, as it was for most men. Nothing like exposing one's bare ass hole to make a man feel completely vulnerable. Still, Ethan knew the drill and spread his ass cheeks wide open for me.

"Very well then. You pass inspection," I announced.

Next I had Ethan make his way to the heavy steel spreader bar and I secured his wrists into the suspending cuffs that I had attached to either side.

"Ethan, you are going to be punished tonight and I think you know why, " I whispered slyly into his ear.

"You should know by now that ogling your new young secretary is completely inappropriate and a very disrespectful act, " I informed him. "Do you agree?"

"Yes, Mistress Madeline, I agree, " he replied.

"You need to learn how to exercise self control at all times, " I went on, reaching for my favorite flogger--the one with 45 tails made of deerskin.

I moved in front of Ethan with the flogger draped casually over my shoulder. His eyes widened in excitement.

"Really now, look at you. With a dick so insignificant, do you really think a young, pretty, long legged little thing would even give you the time of day?" I cajoled.

"No, Mistress. She would most likely not, " Ethan answered quietly.

"What do you think she would do, if she ever saw your puny pencil-dick?" I pressed on.

"She'd probably laugh," he replied.

"That's right! " I beamed, slowly moving the flogger down the front of Ethan's body and resting it for a moment over his quite erect penis.

"Such a pity, with a cock so tiny, you might as well be a girl, " I sweetly intoned.

Ethan's eyes remained fixed onto the floor. I moved behind him now and got into place to begin his flogging.

"Ethan, you are to remember that it is not your place to stare at beautiful woman such as your secretary. You are a lowly male with a clitty dick and you have no business entertaining impure thoughts about your secretary, " I stated matter- of-factly.

I delivered 15 blows to Ethan's bare ass, building up from a gentle caress to whopping thuds. Ethan took it with great stride, wincing quietly, but never begging me to stop.

I then helped to release his wrists from the cuffs on the spreader bar, but quickly replaced them with a pair of good old fashioned hand cuffs and instructed Ethan to sit in the chair I had placed right beside the queen sized bed that stood in kitty-cornered in the play room.

I then sat on the edge of my bed and placed my leg on his lap...inching my fish-netted foot up his thigh. His hands are bound behind him, so there is no way he can touch my leg or foot. I delight in rubbing my toes over his pathetic cock, watching it jump to life and throb from the feeling of my soft foot applying pressure to his ball sac. I spread my legs a bit so he has full view of my bare pussy ... only being able to look but not touch or have contact with in any way.

Ethan is almost in a trance-like state as I rub my feet on either side of his cock. Imagine his surprise then, when he becomes aware of another male appearing in the room. I laugh deviously as I make introductions.

"Ethan, this is another play mate and good friend of mine. Meet Julian. Julian, this is Ethan."

Julian and I have played together many times and I chose to have him join this scene tonight because he would serve as an intimidating factor for Ethan. I parade his glorious naked body before Ethan.. Julian's cock is outstanding, a nice meaty organ of at least 9 inches long. I point this out to Ethan, reminding him of his inadequacy, as if he needs reminding! I instruct Julian to lie down on the bed as Ethan is forced to watch me tease his cock with my feet and toes...and when I look over at Ethan, I notice his baby boy dick at full attention, dripping with pre-cum.

I jump up and slap Ethan's cock into submission and demand, "You are to stay flaccid, dear pet, and heaven forbid if you think you are going to be allowed to cum!!"

Ethan timidly complies, as difficult as it is. He then watches in amazement as I sit on my knees on the bed in front of him and begin to stroke and finger my increasingly wet and engorged pussy lips. I tell him that a pathetic, filthy boy like him would never even be able to dream of being worthy enough to put his miniature toothpick inside my silky, glorious cunt. I then proceed to straddle my Julian and Ethan can do nothing but watch as his masculine cock pushes its way past my pussy lips and fills me up in a way he knows he never could.

To make Ethan's agony worse, I slow down for a moment and then climb off of Julian's pulsing cock and order Julian to get off of the bed and stand before Ethan. Ethan looks horrified, his pale face becoming even more ashen.

"What are you--?" he begins to protest and I slap him hard across his face.

"Shut the fuck up, you pathetic boy, " I snap. "Its pointless to whine Ethan, because you are my toy and I play with my toys however I want to."

I tell Julian to stand in front of Ethan and put his beautiful slimy cock to Ethan's lips.

"Ethan, you are going to suck his cock for me, my doll..." I inform him sweetly.

Julian has had dozens of scenes with men before and probably gets off on humilating my subs almost as much as I do.

Before Ethan could realize what was happening, I was leaning over behind him, with my hands on his face and edging it closer to Julian's dick.

"Mistress Madeline, please..." Ethan begged.

"Shhhh...its ok darling...you are doing this for me. You do want to please me, don't you?" I press my lips to his ear, darting my hot tongue around his earlobe.

"Yes, I do want to make you happy, but I've never---"

Its too late, I pry Ethan's wide mouth open and Julian takes his cue and shoves his prick right into Ethan's (somewhat) unwilling mouth.

"There, there, love...it isn't so bad, now, " I warmly encourage Ethan.

He gags a couple of times and this excites Julian more, as he thrusts his pelvis into Ethan's face with increasing demand and persistence.

"You look so beautiful getting your face fucked by Julian, Ethan...really, you look spectacular, " I say lovingly, enjoying the way the scene plays out.

Ethan beging to relax a bit more, I can sense his body becoming less tense and his mouth opening wider around Julian's penis. Julian is moaning in ecstasy and I continue to move Ethan's head from behind the chair and guide it back and forth over Julian's cock.

I am quite pleased with the choreography taking place before me. In fact, I am so pleased that I feel my pussy lips opening up and my clit quiver a bit. I decide its time to redirect Julian's cock and I tell Ethan to stop sucking and Julian to lie back down on the bed. I climb on top of Julian and his dick effortlessly slides into me.

I watch Ethan throughout the time I am riding Julian's gorgeous meat and tell Ethan how fucking incredible his cock feels inside of me and how he makes me cum so very hard. I allow Julian to squirt his juices into my pussy and then I climb off of him once more. I pull Ethan up from the chair and push him down to the floor, where he lies on his back, his hands still cuffed behind him. The final delight is when I crouch down over his face and order him to clean out my lover's sperm with his tongue. His stinky puny cock once again becomes enraged as he is allowed this treat and greedily laps up Julian's juices from my cunt.

"That's right, little toy....clean my pussy with that tongue of yours," I softly say, thrusting my cunt down hard on his mouth.

Ethan has orally serviced me before and he is quite above average in this skill. I reach down and place my hands on both sides of his head and push him harder and further into my dripping cunt, pulling his hair.

Before long, I orgasm again...and again.

Finally, when I feel satiated, I order both boys to dress and be on their way, and we say our goodbyes. The grandfather clock strikes twelve in my foyer. The witching hour. Feeling very much like a sorceress of sadistic pleasures, I retire to my room and settle in for a good night's sleep.