Meeting Mistress by Anonymous

“Meeting Mistress” by anonymous based on a true story, blended with a few other true stories, but with wildly distorted facts and a few bits of fantasy.

Mistress came to visit just as winter transitioned to spring. She travels internationally for work and her next client was in my city. She emailed me a few days before to inform me of her pending arrival. In the email I also found a list of items to gather and bring to her suite.

My mind raced through all the possibilities as I read the list. I ran all over town collecting the items, a few of the items were somewhat humiliating to buy. In a small travel satchel I packed rope, clamps, clothes pens, cuffs, a gag, blindfold, panties, negligee, high heels, butt plug, and an enema kit. Then I slid the brand new crop she requested into a document tube.

Mistress texted me when she, her assistant, and another member of her staff had arrived at the hotel. My instructions were to be in the parking lot no later than 4pm and to wait. Promptly at 4pm I parked my car and waited….and waited….at 4:23 my phone rang…

”hello?” I nervously said
“Room 932, 5 minutes, knock 4 times” and she hung up.

I walked into the exclusive hotel, past the clerks and into the elevator. Up to the 9th floor I went. I approached room 932 knocked 4 times….and waited….and waited….finally my Mistress opened the door, smiled, and welcomed me into her world.

For about a minute we smiled at each other and hugged, it was amazing to be in her presence, not just in second life, but now in the flesh here was my Mistress. Then she spoke softly and said “to the bedroom.” Mistress had a rather large suite with a living room and a completely separate bedroom.

“Place the bag on the bed and go to the bathroom, strip, fold your clothes neatly and return to my feet. That will be your last moment of privacy for the night.” she said firmly.

Instantly I obeyed and hurried off to the bathroom.

As I stripped and folded my clothes, my cock….I mean my Mistresses cock began to respond. In full disclosure, Mistress keeps her cock locked away in a cage with 5 rigid spikes that go across the back of the shaft. Erections can be very painful at times. Mistress finds pleasure instructing me to get hard just for the mere fact she knows it hurts like hell at times.

Naked except for the cock cage, I returned to my beautiful Mistress who gestured me to the floor. I knelt before her as she inspected the items from her list. Pleased she placed her fingers on my lips and I knew I would not be allowed to talk. She then took each of my wrist and padlocked hard leather cuffs to each of them.

“Up on the bed slut!” Mistress commanded “on your back.”

I obeyed immediately. Even though this was our first time together in person, it was so natural.

Mistress tied me spread eagle to her bed, slipped a blindfold over my eyes and started dragging her fingernails over my body and near Her cock. God it hurt, it betrayed me and responded to her torments. Then she gently pushed in a starter butt plug into me.

She leaned down and whispered “Now be a good slut and stay silent. I going to have dinner, then the rest of the evening we will have together. Not a peep from you, do you understand?”

I nodded….and with that in my darkness I heard her close the door. I tested my bonds as I laid there. It couldn't have been more than 10 minutes when the knock came at the outer door of the suite. My heart leaped as I could hear my Mistress welcoming her staff into the main room. There was business talk and laughing. Then another knock
“Room service”.

“OMG” I thought “They are having dinner in the room. here I am naked, bound, and blindfolded and dinner is being served.”

At least two hours past before her guest left  and Mistress returned. Not saying a word she checked my bonds before without warning whipped my inner thighs with her crop. I bucked wildly.  This was the real start to the evening.  Over the next 4 hours or so my Mistress whipped me, gagged me, humiliated me with an enenma...my first ever in my life, had me dress up in my panties and negligee. She had me walk around in my high heels, balancing a book on my head, then to finish the night off, my Mistress removed my gag. bound my wrist behind my back, then she took off the cock cage and pushed me back down on my knees before her.

There she said “Now my slut, stroke!” Her cock was tender from enduring the hours of torment the spikes provided. I stroked slowly as my Mistress reached behind her and produced a black velvet bag. The pulled out a glass dildo and whispered “Tonight my pleasure is watching you and pushing your boundaries” and with that she pressed the tip of the glass cock to my lips “Take it in my slut” she commanded. And with that I sucked and licked her glass cock eagerly as I stroked my cock. Mistress had me take my time and brought me to the edge at least 5 times. Finally when I came she had me catch it in one of those hotel cups. And thats when the final humiliation for the night name...she stirred my cum in the cup with her glass cock and had me lick it clean...she repeated this until the cup was dry.

The evening coming to an end, my Mistress held me close, petting me and telling me how  proud I made her. Then she locked the cage back on her cock and pointed to the corner of the room. I crawled over and curled up. She graciously gave me a pillow and I slept.

When morning came, Mistress was gone already to her work meeting, she left a note, I packed my bag and crop and left.

The End