Working for Miss Black Pt. 03

I drove to a secluded farm out in the sticks. Miss Black sent me there as part of an executive retreat on Servant Leadership, and I had no idea what I was walking into. I doubted there was any cell-phone connection and if there was, it'd only be a bar. Miss Black told me to let my fiancé, Staci, know I wasn't going to be able to contact her this week anyway.

I parked over by the entrance, and walked up the long dirt road, passed the stables, to the house. I walked up to the door and rang the doorbell. When the door opened, I saw Sasha, Miss Black's secretary, there, naked, wearing only a black dog collar with a large steel o-ring, a tight waist corset, leather cuffs, and black thigh-high boots. Startled and not what I was expecting, I didn't know what to say. She opened the door all the way and stood at attention. "You may enter."

I walked through the doors and she escorted me to two large wooden doors at the end of the hall. She opened the doors to what appeared to be the library. She walked over to a replica of Edvard Munch's "Madonna" on the wall and took it down. Behind it was a wall safe. She spun the dial and pulled the lever, opening it. "You are to put all your belongings in here where they will stay for the duration of this week." I immediately stripped down and neatly folded my clothes, placing them in the safe. I turned off my cell phone, and placed my keys on top, before Sasha closed the door and spun the dial to hide the last number.

"Let us begin." Sasha escorted me down to the cellar. There were projection screens on each wall and a lot of video equipment that was in the process of being set up. There was a single wooden chair in the center with a dog collar on the seat. A tag on the dog collar said only "#28." I heard Sasha command, "Sit," and I slowly sat in the chair.

Once I sat down, a video appeared on the front projection screen. Immediately, I saw Miss Black. Seeing her was like giving a starving person a crumb of bread. My heart skipped a beat.

"This is your orientation. For the next week, you will follow the directions of Sasha as my proxy. I will not be in attendance until later in the week, but I will be checking in via cameras periodically. You will wear what I want you to wear. You will do what I want you to do, but you must wear your collar at all times. By the end of the week, I expect you to be the perfect servant leader. Sasha will now escort you to your quarters."

Sasha escorted me to the stables were I was placed in an empty room with no windows, an open grate to use for the bathroom, and a small trough where I assume she will feed me. "Take this...it's your first lesson...a lesson on listening." She handed me a pair of bluetooth headsets, and I could only guess that anything broadcast would come from outside the room.

"Thank you Sasha." She raised her eyebrow, obviously irked at something I said.

"Don't be shy about falling asleep listening to the music," she smoothly sighed as slid the door close, leaving me in darkness.

I slid the headphones on and sat in the corner. A very pleasant, slow paced, relaxing music flooded my ears. It set me at ease. Shortly, I heard a voice echoing lightly in the background. It was Miss Black.

"Relax...set your mind at ease...trust in me...let all the muscles in your body relax...feel the tension in your legs evaporate...and with each drop of stress leaving you, drop further..."

The voice came more to the fore front as echoes of what she said continued in the background. "Release all that tension in your arms (Relax)...let them hang there with no ounce of stress (set your mind at ease)...just exhale out all that stress (drop further)..." The only other part I remember is Miss Black saying, "...and now..."SLEEP!"

Day 1:

"Get up! Rise and shine!" Sasha said as she slid opened the door. I had no idea what time it was or what I was doing. As I sat up I remembered I was naked with the exception of the dog collar around my neck, and the headsets over my ears. As I looked up at Sasha, I saw her dressed in horse-riding attire, holding a leather crop between her leather-clad gloves. "I am not going to order you again. I would like my morning ride before breakfast." I stood up and slowly walked over to the door, taking off my headsets. "Faster!" Sasha commanded as she slapped my ass with the crop. I did a quick hop-step and moved quicker. "Mmmm, that's better. As I walked by her, I got a whiff of the perfume Sasha was wearing. It was the same as Miss Black's. It started to fill my senses, and made it harder to think. Made me more aroused for Miss Black. I mindlessly marched over to the edge of the stable where I heard Sasha command, "Stop! Kneel." I followed her order.

Sasha first put a leather hood over my head, and started lacing it tightly shut. She then put a half-saddle on my shoulders and leather straps around my arms and torso. She wrapped her leg one side of my head, and slid herself on the saddle. I caught another whiff of that perfume, dropping me further. Sasha put a harness over my head, and bit in my mouth. She strapped it tight around my head and grasped the reins tightly. "Up!" she ordered as the heel of her boots gave me a swift kick to the side. I stood up and did as ordered. "Giddyup!" She ordered as she gave me another slap of her crop across my ass. "You will go where I tell you to go #28." I did another hop-skip and started walking forward.

"Faster!" giving me another slap, speeding up my pace. I started to enjoy being a pony...like a mustang, free, unbroken.

I then gave Sasha her ride around the grounds. It was then I noticed there were other trainers here. Each of them on their own naked man-ponies. Each "pony" wore a black latex mask concealing who they were and their collars. "Focus on the road!" Another crop sting shocking my sensitive ass and reminding me of my place.

After Sasha's ride, she took me to the farmhouse, where she unharnessed me. She then poured what looked like protein shake into a wooden trough. "Mmmmmmm...eat up. You'll need your strength for later."

After eating my slop, I was shown down to the cellar once again where I was seated in the wooden chair I sat in for my orientation. I was then strapped to the chair, with something placed on my head, but everything was like I was in a void. All the sudden, a digital signal flashed and it was like I was sitting in a class room.

Click...click...click...click...click...The steps of high heels slowly stepping behind me reminded me of Miss Black and our last meeting...my meeting in her office. I then saw Miss Black's crossed leg, wearing the same red high heels from our meeting bouncing to the right of me. I turned my head to the right to see Miss Black dressed as a teacher, sitting playfully on the desk next to mine. Sitting at that desk was Sasha, sucking on a lollipop, dressed as a little schoolgirl with pigtails, and class uniform.

Miss Black looked so sexy, like a teenager's wet dream. Tight skirt. Hair up. Cleavage busting out from her top. Her blue eyes staring over the glasses she had at the end of her nose to give the thought of you being inferior.

"This is your Virtual Reality session...this first one is on awareness and stewardship... Each day you will be brought here where we will go over further training. Do you understand?"

"Yes, Miss Black."

"Then follow me to the chalk board." Miss Black stood up and walked to the front of the room, sitting at her chair behind the desk. I followed her, not taking my eyes off of her. It was like I was floating. I couldn't feel my legs. It was like they were full of air. I got to the left of her desk and was able to see Miss Black.

"Pick up the piece of chalk...I want you to write 100 times, "Miss Black comes first."

I picked up the chalk and began to write, "Miss Black comes first...Miss Black Comes first." As I did, I saw Miss Black stand up and unzip her skirt, letting it fall to the floor, before kicking it over to my feet. I stopped writing to gaze at Miss Black.

"You're not writing!" I snapped out to see the crooked line I created.

"I'm sorry Miss Black."

I started writing again. "Miss Black comes first...Miss Black comes first." As I did, Miss Black slowly unbuttoned her top, letting each side to barely conceal her breasts. Again, I couldn't help but stare.

"You're not writing again!" She stood up and walked over to scold me. She stood behind me, her tits in back. Grabbing my right hand, she guided my hand to write, "Miss Black Comes First!"

"I'm not asking for much. Just 'Miss Black comes first.' Is there something the matter?" She then grabbed my stiff cock. "Ugh! Always this organ getting in the way of learning...Sasha honey..."

"Yes, Miss Black," she excitedly said.

"Will you come up here and help #28 with his lesson?"

"Yes, Miss Black." Sasha then hopped up and kneeled in front of me. Setting her lollipop on Miss Black's desk. Immediately, Sasha started to suck my cock. Miss Black sat back down and resting her feet on her desk as she watched, letting her hair down. "Is this right, Miss Black?" Sasha asked before smashing her mouth up-and-down on my shaft again.

"That's perfect, honey...now #28...Miss Black comes first."

I was mindless...I didn't know what to think. I started writing, "Miss Black comes first... Miss Black comes first ...Miss Black cums first...Mistress Black cums first..."

Miss Black pulled her thong aside and started rubbing her clit, moaning...purring...sighing, "that's right...keep going..."

I kept on finding it harder to concentrate as Sasha looked up at me, licking the tip of me cock, grasping the base before slamming down hard again. I looked over at Miss Black. She arched her back in ecstasy as she continued to finger herself. The sides of her open blouse exposing her tits fully now.

I kept writing, "Mistress Black cums first...Mistress cums first...Misstress cumms...Misstress cummmmms...Cummmmm...

Sasha was moving faster, faster...up-down, up-down...squeezing harder and harder.

"Sasha honey."

She pulled her head off and clutched my cock to reply, "Yes, Miss Black." Drool hanging from my cock to Sasha's lips.

"Why don't you bend over to let #28 feel your wet pussy on his cock?"

Yes, Miss Black." Sasha then stood up, lifted up her skirt to reveal no panties, and bent over, thrusting her pussy to my throbbing cock. It was so hot and wet. My cock filled every inch of her tight pussy as I balanced myself with one hand on her back and the other writing. "Mistress, cum"

Miss Black rolled her chair closer to Sasha's head. "Lick your Mistress' pussy, honey" Miss Black leaned back in the chair giving Sasha closer access. Sasha immediately started tonguing Miss Black's clit. Her hands on Miss Black's knees, spreading them apart just as her mouth parted Miss Black's juicy pussy she was licking.

I continued to fuck Sasha, but imagined I was fucking Miss Black, like there wasn't anything between us. Miss Black moaned louder and louder. With each moan, I thrusted harder and harder into her. Her pussy feeling so good. Better than anything I ever felt before. The louder she moaned, the harder I thrusted.

My hand, still mindless writing..."Mistress cums...cum for mistress...Cum for your mistress...YOUR MISTRESS...cum...Cum...CUM"

Oh, fuck...

Just then, Miss Black's moans punctuated the level of her orgasm, "OHHHH...!" Her orgasm visually flooded through her body. Her body tightened up as she pushed up on her chair's arm rest. "Don't fucking stop!" Instantaneously, I couldn't hold it any more. I shot my load, still pounding away at her. Every nerve in my body firing at once.

Then everything went black. The only sound was my deep inhales as I tied to catch my breath.

My virtual reality headset was removed to show the empty cellar. I looked down confused. Here I was still restrained naked to the chair. A month's worth of my cum all over me and on the floor. I then heard those heels from behind me...click...click...click... I felt a hand softly pet my head before clenching my hair and pulling my head back.

"What was the lesson for today!" Sasha demanded as she stood there. Black lipstick, black thigh high boots. Black corset. Black collar. Her black hair banded, just like Miss Black's. She flung her flogger at the side of the chair several times to let me know it was there as she sternly stared at me, trying to make sense of everything. "I asked you something #28!" Sasha then came down with the flogger across my thighs.

"Miss Black comes first."

"Do you see Miss Black here?"

"No."

Another lash of the flogger across my thighs again, with some of the straps slapping across my balls this time. "Ouch..."

"Am I not Miss Black's proxy, her steward?"

"Yes," I cried back.

"It wasn't a problem for you when you were fucking me, but thinking you were fucking Miss Black, was it?"

"Yes," I blurted out

Another lash across my thighs, this time even more flinging more of my balls. "Yes, what?"

"Yes, Miss Sasha." Another lash of the flogger. "I mean, Miss Black."

"And did I cum?"

"No, Miss Black."

"That's right. Now eat your cum off the floor." She released the restraints and I fell to the floor in exhaustion and pain. I pulled myself over to the cum puddle on the floor, meekly stuck out my tongue, and licked the load of cum I exploded.

"Mmmmmmm...that's better," she coyly replied. "Make sure you eat all of it. You're going to need all you can get this week. Here ends your lessons on Stewardship."

I woke up in my stable. I was already on all fours. A harness collar kept me from doing anything but looking straight ahead of me. The collar was chained tightly to the side wall to keep me from moving at all. I felt a soft pat of leather gloves along my side. Stroking my back, my ass, the back of my thigh, back up to my ass where the gloves gave a soothing relief from my sore welted ass and the flogging I took from Sasha (Miss Black) last night. I felt a belt strap thrown over and wrapped back around through my groin. Something rubber was then placed over my cock and wrapped around my balls.

"Hummmmmmmmmmmm..." It started humming.

I felt the rubber contraption start to constrict around my cock, stiffening it and becoming faster. Faster...Faster...faster...harder...faster...until I came again.

I heard the person stand up, place the leather gloves on the small of my back...fingernail against my back, slowly walking up the front, and squatting in my view. It was Miss Black. I inhaled her smell, floating me higher. I felt euphoric.

"We're going to I drain every last drop of resistance from you. Do you understand?"

"Yes, Miss Black." I felt the device continue to constrict and vibrate, harder, faster...bringing me to the edge of wanting to cum again.

"Milking time." Miss Black laughed.

"Get up! Rise and shine!" Sasha said as she slid opened the door to my windowless room in the stables.

I woke up. Where was Miss Black...Was that just a dream? I couldn't tell what fantasy was or what reality was anymore. I pulled the headsets off my head and stared in amazement.

Sasha (Miss Black), in her riding attire but this time going crotch less grabbed me by the collar. "Day 2, today I'm going to take it so much harder on you. I'm expecting a more exciting ride than yesterday."

I inhaled that scent and said the only thing in my mind..."Yes, Miss Black."