Jamies Descent

Jamie's Descent Part 9

This chapter is dedicated to Lexi, who used to be a twink, Tristan

I live for feedback nikkie.silk@outlook.com

Vanessa smiled to herself as she viewed the edited version of the film she had made of Jamie getting fucked. Jamie obviously had no idea that she had been filmed but Vanessa was already very pleased with the result. This film together with a similarly edited version of Jamie's first session with Fiona would form the basis of the marketing plan for Jamie.

Vanessa knew that there would be a number of existing clients who would cream themselves at the prospect of a session with Jamie already but Vanessa, as usual, was thinking much bigger than that. She felt Jamie had a star quality that she hadn't seen in anyone else for a long time. With careful grooming, the right training and good management she could turn Jamie into a star. Jamie had vulnerability mixed with a sex appeal that just dripped off the screen. She was young, could be beautiful and just might make them a fortune, one way or another.

Right now, though, Jamie was just a diamond in the rough, and there was a lot of polishing that had to be done before you could assess the true value of this precious little stone. Fiona had turned him out very satisfactorily and as a bonus Jamie had voluntarily submitted to Fiona, and would now do anything that Fiona wanted. Jamie was now on the verge of sissydom and it would take only take a tiny push for Jamie to become a perfect little sissy.

The hormones had begun to work on Jamie and her breasts had begun to develop, her skin was looking beautifully soft and her hair was improving too. Fiona had told her that Jamie's cock was still functional which was another bonus. Fiona was happy to let things move on. Fiona let me sleep late the next morning but then woke me up and told me I had a job this evening.

"What job Miss Fiona?" I asked very nervously.

"It's still part of your training, Princess, but it's something different for you."

I thought that different could be good or bad.

"Every so often there's a party held for wealthy men and women who like girls and boys like you, Jamie. They get together and have a good time and they are served and waited upon by little sissies and femboys. At the end of the evening if you're lucky someone might take you up to one of the bedrooms. Now we don't normally do this, but Vanessa thinks it's a good way for you to develop some skills that will be useful in the future."

"What kind of skills?"

"Nothing you haven't practised with me, so there's nothing to worry your head about. If you do a good job, there might be something nice for you when you get back."

"Get back? Where is this party?"

"It's in a big private house in the country, I'll take you there and I won't be far away so there's no need to worry. Now, what to wear?"

I started to worry. This would be very different from what I had been doing with Fiona. I trusted her and would do anything for her, but this will be with different people. I started to imagine the most horrible things happening to me and began to hyperventilate. Fiona immediately grabbed me and held me tight and stroked my hair and spoke softly to me and I immediately began to calm down. She had that effect on me.

"Jamie, princess, there is nothing to worry about. I will be there and nothing bad will happen, I promise." She cooed to me. "Jamie girl, do you trust me?"

"Oh yes, Miss Fiona, of course I trust you."

"Then my pretty little sissy, you should know that I would not tell you to do anything that would be bad for you. I am your mistress now and that means I have to look after you. It also means that you need to trust and obey me. Do you understand?"

Mistress! My eyes opened wide as I thought about that word and what it meant. I was already devoted to Fiona but this would take everything to a new level. Fiona was my mistress, she owned me. I shivered with delight at the thought.

"Yes, Miss Fiona, I mean Mistress, I understand and I do trust you completely."

Fiona smiled to herself as she heard Jamie accept her role and to use Mistress without even being asked.

"Good, Jamie, now let's get you ready for tonight."

I felt a tingle of fear and apprehension as I looked at the clothes laid out for me on the bed. The party girls would be in fancy dress and the guests in formal clothes and Fiona had selected a devil theme for me. Everything was in a bright scarlet and I picked up a tiny pair of bright red panties and drew them up my legs. I would never get tired of this feeling, I thought, as I pulled them tight to cup my cock and balls. It made me quiver inside.

There was a short tutu skirt which barely covered my panties and I knew would show everything I had if I bent over. I tightened it around my waist and the layers of material immediately made it flare out. The top was a scarlet basque that Mistress Fiona had taught me to put on back to front and swivel it round. It felt very tight and uncomfortable at first. It pulled me in at the waist and pushed me up at the top. There were also red thigh high stockings, long red gloves, a set of small red horns on a head band and a pair of 3 inch red heels to complement everything.

I looked at myself in the mirror and I almost fainted. The outfit looked stunning. The basque top pushed up my small breasts to such an extent that it really looked as if I had a cleavage. It pulled in my waist as well which emphasised the flare of the tutu. Of course, everybody would be able to see my small scarlet panties but that was the point I guess. I turned and looked over my shoulder in the mirror bent slightly forwards and wiggled my bum. Oh, that made me feel all warm inside.

Fiona walked round me to inspect how I had done. As she disappeared behind me I tried to follow her with my head, which earned me a stinging slap on the bum.

"Eyes straight ahead."

"Yes, Mistress," not daring to rub my bum which was sore from the slap.

"Not bad, sissy, not bad at all. I think you'll do."

"Thank you Mistress Fiona."

Fiona said that I should learn how to serve properly before I got to the party. I was confused, how difficult could it be to serve someone a drink. She asked me to pretend as if I was serving her a drink. She sat down and clicked her fingers at me and I walked across to her and stood there waiting.

No. no. no, that won't do at all.' She looked angry and I wondered what I had done wrong. First of all, you need to walk properly. Work that cute little bum of yours. Make it wiggle, God gave you that pretty little butt for a reason and the reason is to show it to everyone. You really have to emphasise it, throw your weight from one side to the other, I want to see it move. Secondly, when someone calls you over, you need to curtsey and say, `Good evening sir or madam, my name is Jamie, I'm at your service this evening, what can I do for you?'

I was looking confused.

`Oh my God, watch me you silly little girl.'

Fiona stood up and walked slowly away from me, her bum wiggling from side to side as she walked. She stopped, walked back and curtsied, bending her right leg and bringing the left one gracefully behind with the toes on the floor and dipping her head towards me.

`Good evening sissy, my name is Mistress Fiona, I'm at your service this evening, what can I do for you?'

I had to put my hand up to my mouth to cover my giggles.

`Jamie, do you want me to hurt you?'

No, Mistress Fiona,' I tried to stop giggling and said, let me try, please?'

It took me about three of four tries to do it properly and Fiona seemed happy so she said we should move onto serving. She asked me to imagine I was bringing a drink back to her. I started to walk back, this time wiggling my bum for all I was worth, and bent at the knees to put an imaginary drink down.

`No, no, do I have to teach you everything?'

`Yes, I mean, no, yes Mistress.' I was horribly confused, what had I done wrong this time?

First of all, nice bum action but you are serving drinks not a sack of potatoes. You will be bringing the drinks on a serving tray, holding it underneath with the palm of your hand. Then when you reach the guests you stand still for a moment until they let you know they are ready for you to serve. You say Your drinks Sir or Madam.' Women are served first, of course. You bend from the waist keeping your legs straight and your knees together. When you have handed the drinks to the guests you say, `thank you for allowing me to serve you' and wait until they dismiss you. Is that clear? Try it.'

It only took me a couple of tries this time to get it right, but what was obvious was that when bending over I would be revealing my bum to everyone. I blushed at the prospect, whether with shame or anticipation I wasn't sure. Fiona was eventually happy with my practise and she declared that it was time to go. She gave me a long red cloak to wear over my outfit to keep it neat and tidy and we stepped out of the house and into a chauffeur driven car. The driver appeared to know where to go without being told and we slipped through central London, past the suburbs and out into the countryside.

Fiona and I sat in the back seat of the car and I cuddled close to her as I grew increasingly nervous.

"Stop shaking," she told me, "there's nothing to worry about."

"Yes, Mistress," I said, "but you will be close to me won't you?" I pleaded with her.

She put her arm around me and gave me a tender squeeze.

"Yes, Jamie, I will be close."

Just then the car turned into off the main road, drove through a set of huge metal gates and along a long driveway. The car eventually pulled up outside the biggest house I had ever seen. Fiona tapped me and said, "We're here, you can get out now."

I had been taught the proper way to get out of a car and as the driver came round and opened the door I kept my knees together and swung sideways to put both feet on the ground. Wearing a normal skirt that would have been fine, wearing what I had on it made no difference, but you should still do things correctly I thought.

Fiona hurried us through the house and she took my cloak away so that I stood only in my tiny little outfit. I felt very vulnerable and all I wanted to do was to hug Mistress and have her to protect me. She walked me into a larger room and my mouth opened wide in surprise. The room seemed to be full of girls and boys. I looked more closely and I saw that in fact they were either girls en femme like me or femboys.

Fiona scanned the room and whispered to me, `You're the prettiest one here by a mile, Princess. You will be popular tonight.'

She escorted me across the room until we stood in front of a tall woman, dressed in a long evening gown. She turned to us and exclaimed, `Fiona, how perfectly wonderful of you to come. Oh, I say, what have you brought me? She looks deliciously devilish.'

Fiona smiled sweetly and said, `Sissy Jamie, meet Alicia Courtney, she will be in charge of you all this evening. In my absence you must do whatever she tells you, is that clear?'

Yes, Mistress, perfectly clear.' I curtsied to Fiona and Alicia clapped her hands in delight. She's adorable, Fiona, can I borrow her for a while? Please?'

Fiona looked at me and then said, `Yes, Alicia, but I want no harm to come to her, is that understood?'

`Clear as a bell, Fifi, clear as a bell.'

I thought, Fifi? The look on Fiona's face made me think I should never call her that.

Fiona and Alicia were deep in conversation and it gave me a chance to look around. It was an incredible sight, maybe fifty or so people in the room, some chattering to each other, some stood on their own and some like me with a Master or Mistress. There were a lot of different costumes; school girls, policemen and women, slave girls, slutty boys with makeup and fishnets, a couple of cat women and at least two supermen eyeing each other up. There was a lot of flesh on show but I agreed with Fiona that there was nobody there as pretty as me and that cheered me up.

I saw one femboy stood beside his master, he had on very tight blue shorts on over fishnets and heels, with a tight blue shirt with a mesh panel at the front so you could see his lithe and flat chested figure. He wore light makeup and a policeman's flat cap on top of his flowing hair. He looked over at me and smiled. I thought he was very cute and smiled shyly back.

Fiona finally left and Alicia came over to me and with a lecherous look and her face said t me, `You heard what your Mistress said, you are to do anything I ask, is that clear?'

`Yes, Miss Alicia, anything you ask.'

`In that case come with me.'

She led me away from the main room and into a much smaller side room, she locked the door behind her and said, `Get down on your knees where you belong and keep your eyes on the floor.' I slid to my knees, placed my hands behind my back and stared at the floor.

I heard Alicia light a cigarette and she took a deep drag. I heard the rustling of her dress and she came round to stand in front of me.

`Look up now,' she commanded.

I looked up at her and she had pulled her dress up at the front to reveal a pair of black lace panties framed by black stockings and a suspender belt. I looked up to her eyes and she took another long drag on the cigarette and said, `Pull them down.'

I reached up, grasped the dainty lace panties carefully and slowly pulled then down. To my surprise there was a small but very nicely shaped cock nestling between her thighs.

`You may start,' she ordered.

I reached out and took the cock in my hand and it jumped and I felt it begin to grow. I leant forward and kissed the tip and felt it growing still more. It wasn't large and I could easily fit it into my mouth. I used my tongue and lips as I had been taught and it wasn't long before Alicia's hands came down on my head and she began to rock her hips forward to push her cock faster and faster into my mouth. I felt her cock tense in my mouth and I heard her grunt just before she came into my mouth, her cum filling me up. I swallowed it as fast as I could as her cum did not taste that nice and I wondered what she had been eating to make it taste that bad. I licked the residue from the end of her cock and I tucked it back into her panties and stayed on my knees my head bowed down once more.

Very, very good,' she said, Fifi has taught you well. You are a very good cocksucker.'

Her praise sent shivers through me and I felt very warm and proud.

`Thank you, Miss Alicia, you're too kind.'

She clapped her hands once more and almost squealed, "You are too good to be true, I swear it. But let's get going the guests will be arriving soon."

Alicia, or Miss Courtney, as she wanted us to call her, gathered us all together and told us what our duties would be. We were all given a number and told to put that on our costumes so that the guests could see it. Some had been here before but quite a few were new like me and Miss Courtney paid special attention to us. I could see my pretty police boy stealing looks at me all the time and I blushed once when I looked up and he winked at me.

`You, police boy,' Miss Courtney's voice boomed out. My pretty boy tried to look innocent, but she went on, 'the boy dressed as a policeman, pay attention.' He looked chastised and I grinned at him.

We all gathered together after the briefing chattering away, comparing costumes and a lot of touching went on, some innocent and some surreptitiously not so innocent. Miss Courtney clapped her hands and said, `Be quiet, all of you, including you, police boy.'

I glanced over at him and he stuck his tongue out at me.

`The guests will be arriving shortly, so go through to the main hall and stand by the walls and wait for someone to call you over. Remember what you have been taught.'

We stood where we were placed against the walls and watched as the guests began to enter the room. There were tables in the centre and some guests sat and some stood chatting to each other. They were formally dressed with the men in dinner jackets and the women in evening dresses.

All would have looked perfectly normal at a company dinner or a society event, except for the fact that everyone wore a mask. The men wore simple black masks and the women wore more elaborate ones, but all served to conceal their identity. They all seemed to pay no attention to the masks and it seemed they were accustomed to them.

We began to be called over to serve and a tall elegant black man called me over. I remembered all my practising with Fiona and curtsied and made my little speech. He asked for a scotch on the rocks in a voice that seemed to come from somewhere deep in his chest. I have to admit it made feel quivery inside and I felt my cock tingle just a little bit. I came back with his drink and waited while he finished talking to another man and then nodded to me to bring his drink over. As I served him his drink I noticed he looked at the number I was wearing but I didn't think much of it at the time.

Time passed quickly as the room began to fill up and we were kept busy serving guest after guest. It was obvious that there were no holds barred when it came to us and I had been felt, caressed, pinched, rubbed and even slapped on my bum and indeed the front of my panties too. It was the same for all of us and there was only one incident when my police boy managed to drop a drink on one of the guests who had just pinched my bum very hard, making me squeal. The guest was still laughing until the drink landed in his lap. I looked at the police boy and he just winked at me as he was cleaning the guest's trousers, who seemed to be enjoying the attention he was getting around his groin.

At that moment one of the men stood up on the stage at the end of the room and clinked a glass with a spoon to get everyone's attention. Conversation gradually fell away and when the room was quiet he began to speak.

Good evening everyone and welcome to our little gathering tonight. An especially warm welcome for those of you returning tonight and a very special hello to those joining us for the first time.' There was some applause and he held up his hand for silence and then continued, I don't want to delay the proceedings so let me just say that we will be having our entertainment in a few minutes. So take the chance to have another drink before the performance begins and get the chance to examine our pretty little sissies and femboys one more time'

We all had to run around to serve the guests more drinks and I was touched again more times than I can remember, both at the front and back of my panties. My feet were aching with spending so long on my feet and I was glad when the lights began to dim in the room and music began to play. Of course, the darkness allowed someone to grope my cock hard and I squealed and jumped away.

Spotlights ripped through the darkness illuminating a stage at one end of the room. Everyone turned to watch what was going to happen on the stage so I moved slowly to the wall on one side of the room and watched from there. The music dropped away to a steady background rhythm and I saw a tall figure walk out onto the stage. I gasped and my hand shot up to cover my open mouth as I recognised Fiona, it was my Mistress. She was wearing a black cape wrapped around her body, and a mask to cover her but I could tell my Mistress anywhere.

She twirled around and the cape floated out to show that she was naked under the cloak except for a pair of red heels. She stopped with her back to the audience and slowly let the cloak slide off her shoulders and then down to her waist. She looked over her shoulder and then let the cloak drop to the floor. She remained with her back to the audience and I could see she had oiled her body because it glistened in the lights.

She finally turned to the audience and there was a gasp as they took in the full magnificence of her beautiful body exposed to them. Her breasts stood firm and proud and the oil made her skin glow.

I felt like clapping my hands together and shouting, `That's my Mistress.'

She stood for a moment and then strode across to the edge of the stage where she held out her hand which was grasped by a very pretty blonde girl dressed in a white baby doll nightdress that fell to the top of her thighs. It was sheer and you could clearly see her panties through the material. Fiona brought her to the centre of the stage and the girl did a pirouette to the audience, her nightdress flying out from her body.

Fiona move to the other side of the stage and brought on an equally pretty redheaded girl dressed in the same nightdress but in black. She moved to centre stage and pirouetted as well. Fiona stood between them with her back to the audience and gradually she pushed her hands beneath the night dress of each girl and until she reached their breasts. She began to stroke and caress both girls' breasts as the volume of the music began to rise again. The girls threw back their heads as Fiona continued to feel and squeeze their breasts. Fiona leant towards the girl to her right, kissed her and you could see her tongue flicking out into the mouth of the girl. She repeated the kiss with the girl to her left and then pulled the two girls to the centre of the stage so that they were kissing each other, their hands all over each other beneath their nightdresses.

Fiona walked off stage as the girls began to embrace and kiss passionately, and at the same time they stepped back and pulled off each other's nightdress and tossed them aside. The audience murmured its approval as the girls turned to face the front, naked except for their panties. They stood for a moment until the redheaded girl stepped behind the blonde and slowly pulled down her panties until they were on the floor around her ankles. The blonde now had her hands over her groin and she looked at the audience, smiled sweetly and let her hands drop away to reveal a large cock hanging between her legs.

The audience roared its approval as they saw what the girl had hanging there. Quickly the blonde did the same for the redhead and the roar was even larger for her as it seemed her cock was already hard. My tummy did little flips as I saw these two girls with their cocks in full view on the stage. I liked the redhead best I thought because she had a bigger cock and I started to imagine what it would be like if it were me up there. The thought made my cock tingle and grow inside my panties.

The blonde dropped to her knees in front of the redhead and took her cock in her mouth and started to suck her hard. The redhead put her hands to her breasts and pulled and kneaded them as she was being sucked. The blonde was using her hands and tongue and lips to give the other a great blow job. The redhead tapped the blonde on the head and they swapped places, the redhead on her knees worshipping the blonde's cock. I could see the fully erect cock of the redhead as it flapped around in front of her and I imagined taking that into my mouth and sucking. You could feel the temperature of the audience rising as the action went on up on the stage.

At that moment, Fiona move back onto the stage and the audience gasped again as they saw a huge strap on protruding from her groin. She walked around the stage with this fake cock waving in front of her, the two girls seemingly oblivious of her and it. She came up behind the two and they seemed to become aware of it for the first time. The blonde dropped to her knees to join the redhead and they both started to suck and lick the phallus that Fiona was wearing. My knees were now feeling shaky as I saw the full size of the strap on. It was much bigger than anything I had ever experienced.

The music was now louder and seeming to drive them on as the blonde went down on her hands and knees and Fiona moved to her front and slid her mighty cock in the girl's mouth. She began to suck wildly on the fake as the redhead moved behind her and slipped to her knees. She reached out, opened the blonde's cheeks with her hands and I could see her tongue flick out to lap around the exposed rosebud in front of her. The blonde jumped as she felt the girls tongue and then pushed back onto it and I saw her tongue disappear inside. This went on for a few minutes with the audience becoming more and more excited and I heard a few moans from women in the darkness as they were fondled by their partners.

The redhead finally withdrew her tongue, got to her feet, straddled the blonde's backside and let her spittle drop down and used it as lubrication. Then we all saw her plunge her cock into the blondes gaping hole, she jerked as she felt the cock hit home and then the redhead began to drive her cock in and out very fast. The blonde was jerking and straining to hold the fake cock in her mouth and then suddenly the redhead groaned and her body tensed and she very obviously came inside the blonde. To cheers and applause the redhead pulled her cock out of the blonde.

My cock was now straining inside my panties and I had quick peek at some of the others standing close to me and they seemed to be in the same condition.

The pretty boy in the police outfit sidled up to me and whispered in my ear, `I bet you're a horny little devil.'

I giggled and he went on, `I'm here to detain you, put you in my handcuffs and take down your particulars.'

I giggled again and said, `If you do I'll have to poke you with my fork.'

He giggled at that and I suddenly felt a hand on my bum, Stop that,' I hissed, Somebody will notice.'

He kept his hand on my bum and started to move it around caressing my cheeks. I wiggled to try to stop him but it only made things worse and he increased the pressure. I was sure someone would notice, but we were slightly hidden behind a column and nobody seemed to be paying us any attention.

`What's your name?' I whispered to him in an attempt to distract him from my bum.

`Lexi, what's yours?' it made no difference; he was still rubbing my bum cheeks.

`Jamie,' I whispered, trying desperately to not wiggle too much but it was so difficult not to.

On the stage the redhead now slipped to her hands and knees and Fiona quickly strode to stand behind her, the fake cock shining under the lights. The blonde now pushed her cock into the redhead's mouth who started to suck vigorously and noisily. Fiona paused with the cock right at the edge of the blonde's hole, like a bullfighter about to deliver the death blow to a bull.

I could feel the anticipation ripple through he audience as they awaited the thrust, and there were a few muffled shrieks from the women and maybe some of the men. The blonde tensed visibly as the massive cock edged into her hole. Fiona rocked forwards and back easing the cock into the girl. The blonde cried out as Fiona forced it through the girl's resistance and finally the cock was inside the blonde.

The audience let out a collective gasp as the length of the cock disappeared into the girl. I was watching with my mouth open imagining that massive cock ripping my insides. My eyes closed and my boy pussy twitched as I thought of that big black strap on penetrating me until I almost cried out.

Fiona kept the rhythm going until the blonde moaned loudly and we could all see her climax, her white cum spurting onto the floor. There was a roar of approval from the audience as Fiona withdrew the cock and turned to show it to them.

Lexi slipped his hand inside the top of my knickers and a finger started to probe my crack. I was now trying to slap the hand away but he just giggled and kept on. His finger sliding down my crack started to feel very nice indeed and I had to bite my lip to stop myself moaning out loud. I turned to face Lexi and he looked so pretty I couldn't resist giving him a quick kiss on the lips.

He giggled and then took his finger out of my knickers and making a perfect little O with his lovely red lips, he slowly drew his finger into his mouth and began to suck.

On the stage Fiona, flanked by the two girls were bowing and taking the applause of the audience, Fiona had removed her strap on and the two girls cock were still erect. The all walked down into the audience and I could just see that they were being felt and fondled by the guest as they made their way through them. I saw one man stop the redhead and take her cock into his mouth and suck for a few seconds. The blonde was pulled onto the lap of a woman who slid down the front of her dress and allowed the blonde to lap her breast. The three of them eventually made their way to the back of the room and Fiona saw me and walked across, her naked body still glistening with the oil.

She stopped by me and kissed me, and then said, `Remember, whatever happens, I'm not far away.' With that she disappeared through the door.

Lexi whispered in my ear, `Fuck, is that your Mistress?'

I looked proudly at him, `Yes. It is.'

`You lucky little bitch,' I heard him whisper under his breath.

The man clinked the glass again to get attention and it took much longer this time for him to get silence.

"Now we will move on to the main event of the evening, our auction.'

More applause and most of the heads in the audience turned round to look at us serving boys and girls lined up against the wall.

I turned to my new friend and whispered, `What's up for auction Lexi?'

He turned to stare at me,

`Don't you know?' he whispered incredulously.

`Know what?' My eyes wide open with surprise.

`It's us, we get auctioned. Didn't your mistress tell you?'

To Be Continued