I felt like it could be worse at this point. I was sold or at least rented out to the highest bidder by my Master and now it seemed like my fears were unfounded. The little old fellow who bought me seemed only interested in my learning how to be his twink even though I was somewhat hairy and thick. He had me dressed up in a white mini dress that was so small and tight that I had to keep pulling down the hem line with a wiggle of my hips to keep my somewhat large round young ass covered. The shoes were so small my feet hurt as soon as I was able to struggle into them. I was made to walk and move like a whore but just not falling off the high heels was about all I could manage. Even though I could see the bluge in his pants as he sat in the dining room and gave me commands on how to walk, move and even my facial expressions to mimic a lady, I still felt silly. After a while of this I heard a chime melody play somewhere in the house. He put me on my knees and told me not to move. I knelt in front of the chair as he got up to answer the door. He returned with a hot looking middle aged lady carrying a large case of some sort. "Now sissy boy you will learn how to really be the bitch I want. Do as she says and you may get a surprise later tonight". Well let me say that I did not learn much about how to apply makeup but crazy thing was when she was done making me up I thought "damn Im not a bad looking chick with a dick made up like this." I had very dark and thick eye liner on with eye shadow a call girl would be jellous of in , 3 different colors. A little blush and blood red finger nails matched the glossed red lips. I said to the nice make up artist "wow, I'd do me".
She laughed and said "well let me help you try to walk like a lady .....or a slut in those shoes". After about an hour and a half I was strutting around like a whore! Of course in those shoes i had no choice to but through my ass and hips like a street walker. And my calf muscles started to burn but I was strangly turned on and the instructor noticed. "Oh...ok we need to strap that thing down or I fear you will be punished severely if he even sees your manhood. Remember that to him you are female."
"Ok, how do we do that?"
She reached into her bag of tricks and pulled out a wicked looking stainless steel contraption with leather straps and a master lock on it. "Male chastity belt, or aka a cock cage. In this he will not see your uh...manhood as it goes in here". She indicated the small metal cock shaped part and ring of the cruel device.
"My cock goes in that?" I asked.
"Cock and balls" she said with a devious smile. "Put one foot on the chair, spread your legs and pull up the dress". I did as told as she tied a short string to my cock head and passed this through the Chasity device. She used the string to pull my semi hard cock deep into the cock cage. It was to small and it hurt and i inoticed that it had small metel spikes inside digging into my dick so I asked "there is not enough room in it for my cock when it gets hard."
"Then don't get hard" she said with a smile. Next she put the small metal hinged ring around my cock and balls and closed it with much trouble as it seemed way to small. She hooked the part on my cock to a shaft in the metal ring and clicked it together with the master lock. The straps went between my legs and around my waist. With the chasity device completely on I saw that it would not come off without removing the lock. It was very tight and wirh my balls already swollen with pent up cum, the pain was intense! "Ok my friend we are done so kneel down and wait for Edw...uh..your master." With that she winked at me, collected her stuff and walked out. I thought "well still not to bad" as I knelt down, eyes on the floor and waited for master.
It was not long when he returned. "Stand slave and do a turn". He stood back and looked me up and down. "Well now my cunt, you are stunning!"
"Thank you master".
"Ok, ok now let me see you move, walk away from me and back. On the way back look at me and convince me that you want me like you want no other man"! I did as told and walked away from him in the most sluty sashay I could manage. Oh my God it turned me on and I got rock hard with much pain as the cock cage spikes dug into my cock deeper! I heard him say "mumm humm" as I made my turn. I lowered my head just a touch letting my longish hair fall on my face and looked right in his baby blue eyes and opened my mouth just a little to let my tongue sensually snake out to lick my upper lip! I stopped a few steps in front of him with my hips cocked and legs apart. Again he ate me with his eyes and asked me "ok, are you hungry?" A little stunned i just looked at him for a second before answering "ah, yes master."
"Great then my lady, we shall go eat but drop the master thing in public. Just call me sir."
He even asked me what I wanted to eat. Wow, this was a happy surprise as I just answered "Steak...sir".
I have never been wined and dined before but I could grow to like it with this man. We ate steak and sea food at a fine restaurant. The staring and wispering did not spoil the dinner and the humiliation of me obviously being a guy in a dress did keep me hot , hard and in pain. That just got me hotter and harder! Kinda a painful but exciting cycle that had me going out of my mind sexually charged!! On the drive back to his huge house he had me go down on him as he gently stroked my hair. He just unzipped and unbuttoned as i moaned and said "oh yes master, thank you master." I leaned over and pulled his hard cock and balls out from his shorts and butterfly kissed his cock head up and down the shaft to his balls! Kissing and licking them for only as long as I could before my lips were drawn back to his now rock hard cock. Moaning, i licked slowly back up the cock to the gourgess purple head and took it in my lips and sucked , flicking my tounge on it till I tasted his precum. He pulled my mini dress up over my pantiles ass and gave me a hard smack!! As he did this I quickly rotated my hips and was kneeling on the car seat legs wide inviting him in. He did not disappoint me as he shoved two or three fingers deep!!! I said "thank you master" as best as i could with his cock in my mouth! He did not cum but believe it or not I almost did even though i could not even touch myself with the cage. But the pain it caused, the hard cock in my mouth and the wine had me so close!! As we pulled into the garage that first night I was on top of the world and not even thinking about my Master and Madam that owned me!! But before that night was over the fear and trepidation returned along with the desire to get away as fast and far as possible!!!
