[MasterBilly]

Wednesday morning and I was shown into the front room, on the table were the usual clothes, t-shirt, shorts and flip flops in addition there was a small butt plug and a bottle of lubricant. I looked at the butt plug, it was about four inches long, thin but with a sphere about halfway down it. Whether I liked it or not, this was going up my bum at some point today. I accepted it, Mrs Jordan had fingered my bum hole several times yesterday and I currently had £130 in my wallet, in a few hours time that would be £195, riches beyond dreams to me! What was the difference between a butt plug and a rich ladies finger anyway? I was not looking forward to the plug, but I accepted it.

I undressed leaving my clothes in a pile on the floor, naked I asked Mrs Jordan what she would like me to wear. Wordlessly she picked up my grubby underpants and looked inside, turning them inside out she showed the inside to me. I could feel myself getting smaller and smaller in utter shame. There was a light skid mark down the back, to the front there was a visible piss stain as well as a small cum stain. I was so incredibly embarrassed, it would have been bad enough in any environment, but here, in the spotless, sumptuous arena of Mrs Jordan’s house it just looked worse.

“These are disgusting Tony.”

“Yes Mrs Jordan,” I replied, not knowing what to say.

“Why are you wearing disgusting underwear?”

I thought about replying with, ‘I’m not, I have taken them off’, but quickly dismissed it, even if a cocky answer did not incur her wrath it was unlikely to do me many favours.

“Mum didn’t do any washing this week,” it was true, mum used to wash every Monday, but of late she started washing every second Monday, none of my clothes had been washed in over a week.

“Then why didn’t you put a clean pair on out of the drawer?”

“I haven’t got any, I only have four pairs of undies,” my eyes were welling up in the shame of it all. But it was true, I only had four pairs of underpants and by now they were all dirty, though I admit that I could have found a cleaner pair, but I did not know that Mrs Jordan would be inspecting them and I certainly did not know that she would put me through this.

“So what is to stop you washing them by hand?” She asked.

“Er I didn’t know, er, can you do that?” I had never even heard of washing clothes by hand, that was what washing machines were for. I did not have a clue how they worked, but somehow they did.

“Oh Tony, Tony,” Mrs Jordan sighed. “You should at least wash your socks and underpants, it’s hygienic. I will show you how later. In the meantime just put the flip flops on, I would like you to tidy the garage this morning.”

Still feeling humiliated about the underpants I put on the flip flops as Mrs Jordan picked up the butt plug and squeezed some lubricant on it, smearing it over the length of the plug with her fingers. She handed it to me and I held it by the base as she wiped her fingers dry on my dirty underpants. She then told me to come with her and I followed her into the garage. You could of course access the garage from the house, what else in a house this size.

The garage was a mess, things piled up untidily, shelves empty, spanners and screwdrivers left on the floor. There was also a chair by the wall that Mrs Jordan pulled into the middle of the garage. Sitting on it she pushed her knees apart and called me over, I stood a couple of feet in front of her.

“Closer Tony, come right up to the chair, stand between my knees,” Mrs Jordan told me.

Conscious that my limp cock was only inches away from her face I stood there as she admired my bits for a few moments.

“Now Tony, I would like you to put that plug into your bottom,” she told me with a casual look on her face.

I tried, it felt strange, but when it got to the ball it hurt too much. Mrs Jordan gave me advice like ‘try squatting down’, ‘lean forwards’, ‘push out like you are having a poo’. It did eventually slip in and as the sphere went up through my sphincter it was the strangest feeling in the world.

“Now stand up straight between my knees again Tony,” Mrs Jordan loved calling the shots.

I complied and watched happily as Mrs Jordan took my penis into her mouth, unlike yesterday afternoon though, this was the full monty. She slowly worked me up to a full erection and then as I started to get close she reached around and grabbed hold of the base of the plug and slowly pumped my arse with it. I had never even considered ‘anal’ before, yes there were a few schoolboy jokes about homosexuality and taking it up the bum, but I had never seriously considered it. But it was great, I actually enjoyed it. So many things were going through my mind, anal is wrong, this is so right, I am getting paid to receive blow jobs. All these things came together in my brain at the point of explosion, I fired several streams into Mrs Jordan’s mouth and she continued to suck me dry before pushing the plug all the way in, getting out of the chair and leaving me alone in the garage.

What was I supposed to do now, I was naked apart from flip flops, I had a butt plug up my bum, the lady of the house had just given me a blow job and then wordlessly got up and left me, presumably to spit my load out. Was I supposed to start tidying things up, just like that!

I looked inside a couple of boxes, nothing of interest lay within. I was browsing around when Mrs Jordan came back in, she told me roughly where she wanted things putting and that she would be back in an hour, she did not expect it to be finished but she did expect progress.

About an hour later she came to get me and led me into the drawing room (what the hell was a drawing room?), insisting that I removed the flip flops before going into the house. There was an upright chair with its back to an empty fireplace which I was told to sit on, Mrs Jordan insisted that I sat on my hands. I sat on the backs of my hands as I did in the bedroom yesterday.

“Now you are to remain sat there Tony, I will be about half an hour, when I return I may have somebody with me. If I do then we may ask you some questions. In the past Tony you have told me some white lies.”

“I haven’t, I’ve told you the truth,” I blurted out, how could she accuse me of lying.

“Like on Monday when you said you had experience of sex and were currently between girlfriends,” she said with raised eyebrows. I went red, bright red, I could feel my face burning. The fact that I was sat stark naked in her drawing room was irrelevant, I had been caught lying and I could not handle it.

“Whatever, you will not tell lies in front of my guest, if you do then I will spank your arse until it is red raw and then humiliate you to the very core, do you understand?”

“Yes Mrs Jordan.”

With that she left, I sat there and literally watched the clock, relieved that she had not pressed me anymore over the lying incident.

I heard several people arrive at the house over the course of the next 20 minutes or so and they all had female voices. It was about half an hour after Mrs Jordan had left me when she re-entered the room, she had said that she may bring a guest in with her, she brought them all in. I sat there in a state of shock as I counted 8 females as well as Mrs Jordan enter the drawing room and sit down in the various lounge chairs. I had not really noticed before but all the lounge chairs were in a semi circle facing me. Sitting on my hands, which were now getting numb, I had no way of covering my bits up. They examined me at their leisure. Most of them seemed happy, not surprising as they had a naked 16 year old boy to stare at, though a couple did seem very serious. The ladies themselves were all in the 25-35 year old bracket and all appeared refined, elegant and rich; similar to Mrs Jordan, who herself was probably one of the youngest of all 9 ladies.

“Right then ladies, this is Tony,” Mrs Jordan told the assembled group. Murmurs of greetings spread around the room.

“Tony, tell the ladies about each of your sexual fantasies, you have three of them. Go into detail and leave nothing out.” I stared at Mrs Jordan in shock, those fantasies were private, I would never even tell my closest friends. Mrs Jordan had coaxed them out of me in a moment of passion, now she wanted me to tell eight female strangers about my most private thoughts and if I did not do it then she would punish me. How could she, how could she treat me like this. I was aware of her promise to spank my arse red raw, I looked up at her with my eyes pleading for mercy.

“Tell the ladies your fantasies, don’t keep them waiting,” Mrs Jordan said with a hard edge to her voice.

“Please Mrs Jordan,” I whimpered.

“Tony, you know what will happen,” this time Mrs Jordan was virtually growling.

Crestfallen I let my eyes drop to my bare feet, taking a deep breath I began with my fantasy about finding a girl masturbating in the woods, it seemed the least embarrassing until got to the point where I got my phone out and started recording it, I suddenly found myself extremely humiliated telling this part of the tale.

“Tony, look up when you are telling this story, you are speaking to an audience, not your feet,” Mrs Jordan said forcibly. I looked up and saw all the female faces in front of me, they seemed to be eating into me, this was just awful.

As the fantasy went on I talked about me blackmailing the girl, tears of shame started to form in my eyes. I was stuttering and shrivelling up in my seat as I slowly got to the end of the story.

“Well done Tony, now move on to your second fantasy, remember,” Mrs Jordan snarled. “Leave nothing out, tell the whole truth and face your audience when you speak.”

I moved on to the two girls that I knew from school having lesbian sex in my bedroom. I found it slightly easier, it was still fucking embarrassing, but it did not seem as bad as before. At the end, without waiting for Mrs Jordan to tell me I went straight onto my final fantasy about finding a woman tied spread-eagled to the bed, this story I did find embarrassing to tell and by the time that I had finished I was in tears yet again.

“Now Tony, tell the ladies what you do when you are thinking about these fantasies,” said Mrs Jordan.

“Er, I don’t do anything,” I said confused.

“Tell the truth Tony, you play with yourself don’t you?”

Hell fire, surely she did not want me to admit that in front of all these did she?

“Well Tony, tell them all what you do, tell the truth,” Mrs Jordan said.

“I touch my pe ..... penis,” I said, I was completely in tears now, tears of pure shame were streaming out of my eyes and down my face.

“Do you just touch it or do you stroke it?” Mrs Jordan asked, again there was force in her words.

“I stroke my penis,” I replied looking up at her through bright red eyes, thinking how could you put me through this, how could anyone put another person through this.

“Is it called a penis or a cock Tony?”

“It’s called a cock,” I knew that is what she wanted me to say, though I could not understand why she wanted me to call it a cock.

“Then tell your audience what you do and when you do it.”

I looked around at them, about half of them were smiling, thoroughly enjoying my humiliating predicament, the other half seemed to have curious expressions on their faces, I suppose they were wondering if I would actually say something as humiliating as that, but what choice did I have, I was in a deep pit with Mrs Jordan staring down at me.

“I str ... stro ... stroke my cock,” I stuttered.

“When do you do it Tony?”

“When I’m thinking about my fantasies,” I sobbed.

“Then tell the ladies what you do and when you do it.”

“When I’m thinking about my fantasies I stroke my cock,” I blurted out now crying out loud.

“How long do you do it for?” Mrs Jordan asked again.

“Until I cum,” I whispered, looking down at my feet.

“No Tony, say it out loud and look at your audience, how long do you do it for Tony?”

I looked up at the ladies, unable to see them clearly through my tear soaked eyes.

“I stroke until I cum,” I repeated loudly.

“Now Tony, I want you to tell everybody what you do, when you do it and how long you do it for,” Mrs Jordan said cruelly.

“I str ... stroke my co ..... cock ... when I’m ... when I’m thinking about my fantasies,” I stuttered through tears before continuing. “And I do it until I cum.”

“Moving on Tony, I would like you to tell everybody what state your underpants are in,” Mrs Jordan said to my utter horror, I could never do that, ever.

I just sat there with my mouth open, shaking my head, this was unthinkable. Mrs Jordan repeated her instruction, but I couldn’t, I just couldn’t.

“No please,” I whispered out loud.
“For the last time Tony, tell my guests what state your underpants are in.”

I just sat there silently with tears streaming down my face, I could never, ever bring myself to openly discuss that.

“Very well, there will be consequences Tony, but if that is what you want, so be it!” With that Mrs Jordan went across to a chest of drawers, opened the second one down and using a single finger and thumb extracted my underpants, I felt sick as she passed them around.

“Have a good look at these ladies, I suggest that you pay particular attention to the inside, quite gruesome actually. But these are the underpants that Tony turned up for work in today.”

I sat staring at my feet as my undies were passed around the group of women, despite repeated instructions from Mrs Jordan to look them in the eye, my body simply would not do it.

“They are disgusting!”

“What a dirty little boy, he needs a good spanking.”

“Tony, you are disgusting.”

“I want to be sick, I do not know how anybody could be that dirty. Tony, do you actually know how to wipe your own bottom?”

“Oh my God!”

“They are truly disgusting, how can anybody allow their underwear to become so dirty, let alone put them on at the start of the day. I have never, in all my years, seen anything as disgusting as that, he has actually cum in them as well and still put them on the next day.”

I do not know who said what, I was staring at my feet throughout, but all those comments bit very deep.

“Tony stand up and turn around,” Mrs Jordan told me. It took a few seconds to register what she had said, but I complied, just happy not to be looking at the throng of female faces.

“Now touch your toes,” again I complied, in this bent over position I fully expected to receive another spanking but Mrs Jordan actually wanted to humiliate me more, not cause physical pain. She pulled on the butt plug, pulling it part way out so that the sphere was caught in the tight muscle of my sphincter.

“Look ladies, he enjoys wearing a butt plug as well, Tony tell the ladies why you enjoy wearing a butt plug.”

“I just like it,” I said whilst still crying my eyes out, not knowing what to say, but scared of going against Mrs Jordan.

“Okay Tony, you can go and wait for me in the conservatory,” Mrs Jordan said, pushing the plug all the way up me.

I got out of there as quickly as I could and headed for the conservatory, I sat down in one of the chairs and looked out over the garden, shaking like a leaf.