Detour My First Date

My mistress informed me that we needed to have a meeting in advance of my first appointment. First of all, this was my first meeting. Secondly, this client had some particular peculiarities. Ushering me into her study, she first ordered me to put my hands behind my back. As I did so, she produced hand cuffs from a drawer in her desk. Locking my wrists behind me, my mistress informed me, "Your date has specified that you be bound when meeting her. She will have the key. Her name is Annette. When she arrives, you are to greet her by name and let her know how excited you are that she chose you. Since this is your first meeting, it will take place here. In a sense, Annette is helping me to train you. You are to do anything and everything that she asks of you. I will be here to handle any problems. There better not be any problems. Is this clear?"

"Yes, mistress," I replied. "I will do my best to ensure that there are no problems."

"No," she snapped, "You do not 'try.' You just do it."

When the door bell rang, my mistress answered the door. I could hear two women exchanging pleasant conversation. The sounds got louder and louder until the two of them entered the study, where I was. The woman with my mistress was tall, about 5'10." She had long, coal black hair and piercing green eyes. She did not have the appearance of any high-level executive that I had ever known. She wore a low-cut, black leather miniskirt that hugged her thin frame. Black spiked heels completed the ensemble.

"Hello Annette," I began enthusiastically. "It is so nice to meet you. I am really looking forward to spending some special time with you."

"Well, you may want to hold off on that for the time being," Annette responded as she winked at my mistress.

Annette and I were taken to another wing of the property. Annette, though, seemed to know where she was going. We were taken to a large, open chamber that I could tell was a kind of bondage lair. As she closed the door on us, my mistress commented, "I will leave you two lovebirds alone." And, to Annette, "If there are any problems, let me know."

I was now alone with my "date." It was obviously not going to be like any other first date I had ever experienced. Looking me over, she commented, "First of all, let's do something about the size of this penis." Leading me to a medical table, she ordered me to get onto it and lay back. When I did so, she spread my legs and placed them in metal stirrups. She then produced a pump device. Placing the glass over my cock, she used an attachment to pump air into the enclosed. I could see the size of my penis expand as the air entered the chamber. Annette informed me that I would have access to this pump daily from now on. I was to use it for thirty minutes every morning. My mistress would put it on me It was, in a sense, my morning exercise.

Annette further informed me that another part of my daily routine would be a daily "milking." She removed the pump. But I would now need to be "milked." I did not even know what that involved, but I would find out. Annette attached straps to the base of my cock and balls and to the tip. The straps attached to wires that extended from a hand held device with knobs. Teasing me, she laid on my stomach an anal plug with a hose attached. Pumping air into the plug inflated it. I could not imagine that thing inside of me. But Annette spread lubricant first on my anal opening. She then liberally covered the plug with the ointment. I grunted and clenched my teeth as she slowly pushed it into me. "Now for your milking," she said cheerily. I jerked and moaned as she turned the knobs on the hand held device and electricity surged through my cock. I could feel the plug growing inside me as she slowly sent air into it. Caressing my cock, she lovingly pleaded, "Give me you milk, slave. Give it to me." She turned up the knobs.

"AWWWW, GOD, Help me," I cried.

Eventually, juices started leaking out of my penis. "Good boy," she purred. "Now, we will do this every morning after you do the cock expansion exercises." Annette calmly removed the straps from my cock and pulled the plug out of me.

My breathing was labored as she helped me up from the table. Leading me to another section of the chamber, she pulled down a set of two clamps that dangled from a spring running from the ceiling. One clamp was placed above my penis. The other below it. They were then attached with screws on both ends. I groaned and shivered as the screws were tightened.

Annette then produced a flogger. She lovingly caressed the tip of my cock, which extended from the clamps. Taking sure aim, she brought the flogger down upon it. I moaned and pulled away from her.

"Get back here. You are to never do that again. You hear me," she barked? Again.,, the flogger came down on the tip of my cock. I squirmed but refrained from pulling away from her. Again and again, the flogger came down on me. Sometimes, I could avoid pulling away. Sometimes, not. Eventually, Annette mercifully replaced the flogger. Loosening the screws that held the clamps in place, I leaned my head back and took a series of deep breaths.

Annette complimented me, "You did quite well--for a beginner. We will expect you to improve with time, however. And remember. Each morning will begin with your mistress where you will do the cock stretching exercises and the milking regimen. Are we clear on that?"

Not looking at her, I replied, "Yes, Annette."