My Story of Degradation Ch. 02

This story involves BDSM and crossdressing, change of lifestyle and full submission both mentally and physically. If this is not for you feel free to read elsewhere, please.

As I sat there sipping my coffee, I thought about our brief email exchanges, I still knew nothing about her, and I realised that I was very nervous, how should I address her, was I going to like her, did it matter if I liked her if she gave me want I wanted, would I be able to please her and if I didn't how would she punish me.

I guess I was in a bit of a dream when I looked up to see a beautiful woman standing before me. I leapt to my feet, mumbling "Hello Mistress." "Sit down boy," she said harshly with a deep gravelly voice, then she turned to a small girl next to her and said, "Go and get me a coffee, you know how I like it."

She sat opposite me and I sat down again. She was dressed in a 50's style outfit, silken blouse unbuttoned at the top to show a hint of cleavage, her skirt was flaired and fitted snugly to her waist, and flared, I was sure she had a petticoat underneath, she was at least six foot with her high heels, and beautifully made up, she looked like a real woman, but I guessed after 20 years she should.

The girl returned with her coffee, she was petite, had small breasts and was pretty, dressed a bit like a schoolgirl, long hair platted down her back, white shirt tied at the waist showing her belly button piercing, and a very short flared skirt, what I often referred to as a pelmet, and if she bent over she would definitely show her knickers, he had on red fuck me heels that had what looked like at least five inch heels and tiny padlocks locking the strap preventing her from removing them and finally I also noticed that she was wearing a collar, pink and pretty, and as she turned to sit down I noticed a small padlock at the back, hidden mainly by her hair.

"Derek this is Cindy, one of my toys." Cindy sat saying next to Mistress. She turned back to me and said, "Now you have finished ogling us are you happy with what you see."

I went bright red and for the first time in my life stammered "Yes Mistress." She just grinned replying "Oh I can see that you love to be humiliated, don't you boy."

Blushing again, "I am not sure I have ever been truly humiliated Mistress." She laughed at that.

We then chatted for quite some time, Cindy went and got more coffees for us, I offered her the money to pay and she took it from me returning with the coffee. We discussed all manner of things, mainly about my submission and what I was and was not prepared to do for her. She seemed to be happy with what I said and then out of the blue she reached into her bag and passed me a collar, it was black and had studs like a dog's collar, and there was an open padlock attached to it.

"I want you to prove to me you can obey an order whatever the circumstance and wherever we may be. Go to the toilet, put the collar on and lock it and return here." I went bright red and was about to protest then looked at her, she was testing me, and I didn't want to fall at the first hurdle.

Reluctantly I got up and went to the toilet, going into the cubicle and putting the collar on, it was a snug fit, I then looked at the padlock and thought to myself this was the point of no return. Without thinking too hard I reached behind me and fed the lock though the eye, snapping it shut, sadly I did not have Cindy's long hair to hide it. I then returned to the table seeing people look at me then look away, I was sure I was crimson, and my face was burning with the humiliation.

As I sat again both Mistress and Cindy were grinning broadly. "Well done boy, I see you will obey me, regardless of your circumstances. Now where is your car parked?"

"In the multi-storey Mistress." "As am I she replied, come on let's go." And with that she stood up and walked to the door, Cindy and I following her. Once outside the Coffee shop the town was busy, when she slipped a leash onto my collar, and said "Follow me boy show me where your car is."

I was a bit shocked by this, but had little choice, as she yanked the leash, but to follow her towards the car park. Cindy trotted along beside me, smiling and winking at me behind Mistress's back.

As we entered the Car Park she said, "Take me to your car." I headed off that way and she followed closely still not letting of my leash. Once we got there "Unlock it." She said simply and I did as was told. She held out her hand "Keys." I handed them over. She then opened the boot, I had a Range Rover at that time, and she roughly pushed me into the boot, and although there was plenty of room she made sure I was under the parcel shelf so could not be seen.

"Hands." she demanded, and I held my hands out to you and before I knew it I had handcuffs fitted and the other hand pulled behind my back and the second cuffs clicked home, I was helpless.

"Good boy. Now Cindy will drive this home following me, it is too early to let you know where I live, we will see how you get on this weekend." She turned to Cindy and just said "Knickers girl." Cindy had no hesitation in taking her panties off and before I knew it she was holding my nose and as soon as I opened my mouth she pushed the panties into my mouth and stuck a bit of gaffa tape on to stop me spitting them out.

I had been about to protest about the weekend comment as I had not expected that. It didn't really matter as I had no plans, and as I thought about it I began to get quite excited at the prospect of my 'kidnap'.

Mistress slammed the boot, and Cindy got into the driver's seat and we were off, we travelled for about half an hour before the car turned onto what I thought was an unmade road, and within a couple of minutes we stopped.

The boot was opened, and Mistress was standing there looking at me and I saw Cindy hand her my car keys. Mistress grabbed my arm and helped me out and to my feet. I could tell by her grip she was strong, probably fitter and stronger than me, she obviously worked out and kept herself in shape.

She pulled on my lead saying, "Let me show you around my humble home, I think you will find it quite enlightening." She then pulled me round the side of the house to an old barn which looked as if it was about to fall down. Once she opened the door it was clear it was anything but run down. The entry area was concreted and spotless, to the left there was a pig pen, no pigs in it but there was dirty hay, mud and a feeding trough, to the right a stable with horse's tack hanging up but no horse.

She smiled as she saw my inquisitiveness, but I was too stunned to ask any questions. She opened a pair of French doors to the main part of the barn and there was all manner of BDSM items from spanking benches to crosses attached to the walls, to a rack of paddles, whips and crops to cages in various sizes, one standing, a couple sitting on the floor, one so small you would not get me in it.

She said "No doubt if you stay with me you will get to use these items, or at least I will use them on you, there is always a reason for me to punish you. You will learn to obey and suffer for my pleasure, isn't that right Cindy." I could see Cindy blanch and stammer "Yyyes Mistress."

With that she pulled my leash and led me back out into the sunlight showing me a pit with a metal grid locked over it, I saw her grinning as I shied away from it, then on into the house.

It was large, I was later to find out it had 4 bedrooms, three of which were ensuite, a lounge, study, kitchen dining room and another large room that she described as her entertaining room.

"Well boy what do you think." She ripped the gaffa tape off and pulled on Cindy's panties which she threw at her, "Well."

"It's a wonderful home Mistress, may I ask what you do for a living, to be able to afford such a home, and the barn is so well equipped."

"I am a professional TV Domme boy, and a successful one if I may say so."

"Oh, but Mistress I am not looking to pay for your services, I never have paid for anything like this and never will."

She laughed at me, "You misunderstand, I am not looking for you to pay me to submit to me, I want you as a companion and maid in my business, once you have been trained to please me and others, will that be a problem, that is why I mentioned possibly moving here in the future."

I blushed again, it seemed I would have to toughen up or I would be permanently red in the face.

Mistress climbed into a chair which I could only describe as a throne, no doubt what she used when having slaves to visit and to deal with them. She picked up a riding crop and sat facing me and Cindy with the crop over her lap.

She then held out her hand saying simply "Cindy." Cindy walked over to Mistress and took a small bunch of keys from her then moved behind me and she removed the handcuffs.

"Now boy are you interested in coming into my business and being trained by me."

"Yes Mistress, most definitely, could you give me an idea of what I would be expected to do for you."

"Well we will teach you to always be dressed when here, how to carry yourself, serve me and others, both as a maid and personally in my case, be available to others for use if directed. You will also be subject to tight bondage on occasions, and you will, once trained, perform with Cindy and sometimes Amanda, who is my SBBW, for the pleasure of others. Does that sound like something you would enjoy."

I simply answered, "Yes Mistress very much."

"Good we will discuss what time you have to serve later, but for the moment it is time for me to see what I have to work with. Now strip."

I looked at her nervously and started to undress, taking my shirt off first, then undoing my trousers and pushing them down, then I realised I was wearing my satin pink sissy pants with the lace trim, I felt myself blushing yet again, as I saw her smile and grin at me.

"You enjoy your pretty underwear then girl." I didn't answer but saw Cindy lift her hand to her mouth and giggle behind it.

I stood there, wondering what next when she said "Are you undressed? I want you naked NOW."

I immediately pushed my shoes off and bent to take my socks off and step out of my trousers, then I pushed my panties down and stepped out of them as well, that left me in my birthday suit.

She stood and stepped down from the throne, and with the crop in her hand she circled me, looking at my body, tapping my ass with the crop, then my nipples, which reacted and stood hard for her, then she stood in front of me, lifting my cock with her crop, then letting it fall again, this in turn excited me and I started to grow.

"Have you ever been in chastity boy." She smiled at me. "No Mistress never." I replied, my cock twitching at the thought. "Well I don't allow hard cocks in this house, except when I desire it, so chastity will be a must." She flicked the head of my cock gently, top and bottom, and I grew even harder.

She looked me in the eye and said "Your body is adequate for a boy and I like the fact you are fully shaven, that shows that you feel yourself to be inferior to real men. Your cock is of an adequate size and we can easily control that with a suitable cage, you have a nice ass, and with a good corset we will make you look like a woman. If you are here long enough we might even invest in some breast enhancements, save having to stick falsies on you. I suspect from what you have said before that you are an anal virgin, we will train you to take whatever I decide in there."

"Now a final question, are you happy for me to take control of you and teach you to please me, and others, a simple yes or no will suffice, your training will start now if the answer is yes."

She turned and climbed onto her chair, looking at me and waiting expectantly.

My mind was churning, did I want this? Wasn't this what I always dreamed of, but there is a world apart from dreams and reality. And I had to decide now.

To be continued...