The Journey Pt. 05

Job Interview

I received more special commissions, perhaps the strangest for me was Head Mistress Kendra, who had me in her office dressed as a school girl, she could have had everything she took and willingly, for free in my bedroom, but she needed it to be in her office. Afterwards she told me how she had wanted me the first time I bent my bare ass over her knees, I asked why she hadn't taken me, there wasn't a girl who went through that school who would refuse her, but as she explained I understood, using charges outside the school structure as they were trying to come to terms with their new sissyhood could have bad consequences.

That night, as I lay in Chrissie's arms, my pussy still resonating with the effects the fucking she had just given me, I mentioned how lonely I thought Kendra really was. She didn't ask me about the sex, but about what was said and how it felt. In the morning we invited Kendra to come over and spend the night, we were sure a lusty threesome would make her feel considerably less lonely.

Things weres going well when I was again removed from the shift roster and sent to the special room at the top of the tower which overlooked the city. I had heard of it before but never been in it, it was only for the most VIPs of VIPs. In the room, a very richly dressed man stood, the watch he was wearing would have paid for my boob job.

I curtsied as I entered, "Sissy Slut Josephine at your service Master."

He beckoned me over to him, "Scotch, neat," he said, I moved to the bar and I could feel his eyes on my ass, "the same for yourself," his voice rang out. I returned with the drinks, he sat on the expensive leather seat, and without the need of a command, I sat on his lap. He said little, I leaned in to kiss him, "Not yet," he growled, his hands began to explore me, I sipped my scotch as he did. I returned to the bar twice, my pussy had been gently fingered, my clit lightly played with, but I still had done nothing for him.

He looked at me, "Strip," I started to disrobe, "not like that, dance."

It wasn't an unusual request, and I had become a very good dancer, my clothes came off gradually, and I pressed myself against him more and more, finally, in just heels and panties, I began to feel an erection rise as a reward for my efforts.

He stood and pushed me to the floor, he grabbed my hair and dragged me towards the bed, I didn't know what I had done wrong, and I could feel the first tears flow down my cheeks, then I was picked up and dumped on the bed.

He quickly stripped and joined me in the bed, the unexpected mistreatment has scared me a little, but his naked body excited me, I could feel the blood flow into my clit, and my pussy was wet. He slipped my panties to the side and entered me, I gasped, he knew how to use his cock, I moaned in pleasure as he fucked me in that one position for 45 minutes, hard. I came time after time, and still, his cock slipped unrelentingly in and out of my pussy, finally, he filled my pussy with his spunk and withdrew.

He grabbed the back of my head and pushed me down, "Clean my cock, slut."

It went on for hours, I was ridden silly, I didn't think my pussy could take another thrust, "Reverse cowgirl, mount me," he was really powerful and terrifying, my legs trembled as they spread across him, I found his cock, guided it to my pussy, and with one movement accepted all of him in me yet again. It hurt like never before, but I fucked him for all I was worth, minutes passed, I moaned alternatively in pleasure and pain, he liked to buck his hips to give himself that little bit of extra depth inside me at the apex of each thrust, when he came I felt only a sense of relief.

"You'll do he said," moving toward the shower, "you may leave."

Chrissie didn't fuck me that night, she only held me in her arms as I told her het story, in the morning I woke and reflexively started to play with her clit, I don't know why I did it, my pussy still hurt from the night before, she laughed as she bent me over, "You asked for this honey," and fucked me through my pain.

Kendra.

Once a month the salon put on a special show, a full audience participation evening. They changed the theme each month, but Chrissie had told me it always ended up the same, a massive audience participation sex show, it was the wildest of nights.

This month the theme was a Roman Orgy and I had just received my invite to perform on the following night, "Don't be nervous love," Chrissie told me, she was on the schedule as a serving wench tomorrow "you'll love it, you never know what's going to happen, but trust me, there will be plenty of fucking."

I smiled at her, our apartment doorbell rang and I swished my ass over to open it, behind me Chrissie laughed. I let Kendra in, and she joined Chrissie on the sofa, I poured each of us a chilled glass of Asti, handed them over and scooched Kendra over and into the middle.

"Thanks for having me over girls," she said, "it's so nice when one's star pupils remember you."

Chrissie laughed, pulled her towards her and kissed her soundly, "Hey, greedy," I said, "don't enjoy yourself too much," my hands were undoing Kendra's blouse, she was a small woman and her tit almost fit entirely in my mouth as I leaned over to suck on it.

Chrissie and she were still kissing deeply, knowing Chrissie it would be a while before I got my turn, I slipped my hand under her short skirt, no panties, it's good when there are no miscommunications on nights like this, after rubbing her clit for a while I let a finger enter her wet pussy, they explored around until I found what I was looking for, I pushed on the little nub of nerves and I felt her body respond.

I worked her pussy until her juices were flowing and dripping down her thighs, Chrissie came up for air, I looked at her, "I'm good sweetheart."

Kendra let her blouse drop to the floor, "Oh my god, yes you are."

Chrissie and she started kissing again, my fingers were soaked with her pussy juices, and I let them slip back a little entering her ass, lubing her there as well.

Chrissie and I were still fully clothed, well just bedtime Teddies, Kendra has slipped off her skirt and lay back on the couch naked as our fingers and tongues explored her, she was already breathing heavily, and her moaning was catching a nice rhythm. I pulled her hair dragging her face to mine, now it was my turn for a little kissing, Chrissie has spread her legs and slipped down to her knees, her tongue came out like a snake tasting the air, and darted straight for her clit, in moments we felt Kendra's back arch a little, and she screamed, "Fuck yes," as she climaxed.

Chrissie and I stood, each holding a hand out to her, "Care to join us in the bedroom."

All three of us were soon naked and lying on our bed, we formed a suck circle, I had Chrissie's clit in my mouth, Kendra had my Clit, and Chrissie was eating Kendra's pussy.

We were playing a game, first to cum loses, Kendra's whole body shuddered this time as she orgasmed, she lay on her back, eyes closed, "What will her forfeit be my love?" Chrissie asked.

"Don't you two need to play on to see who the winner is?"

"Oh no, first we both win, and secondly we don't need to play to know who losses, Josie always loses, she's such an easy slut," Chrissie was speaking as she was helping Kendra into a seating position, Kendra used a hand to hold her pussy lips apart and started to sit down on Chrissie's raging clit.

I let them have their fun for a few minutes, then I lubed up my clit and approached from behind, Chrissie made her still, and I spread her cheeks wide, I took a few seconds to appreciate the view, Chrissie filling her pussy, and her ass just sitting there twitching for me.

I easily entered her, and Chrissie and I got a rhythm going, Kendra was on the express train to ecstasy, her orgasms were so close together now that it was hard to tell where one ended and the next started, after about ten minutes she screamed like a banshee, and fainted on us.

We slowly withdrew from her and covered her with a silk sheet, I was looking at Chrissie, neither of us had come yet, I turned around, pushed my ass in the air and wiggled it, she giggled as she approached me clit in hand.

The orgy.

"Ladies and Gentlemen, your players for this evening's entertainment, Michelle, Rachel..."

My name was called sixth, I walked out dressed in a diaphanous slave girl outfit, it was light green, and the material was so thin, it left nothing to the imagination, I was naked, not even heels, except for the collar around my neck. There was a silver tag attached to the collar, "Sissy Slut Josie, the property of the Salon, use as you see fit."

Twelve of us lined up at the very edge of the stage, bowed to the customers and then started milling around. Nothing was going on yet, one of the girls dressed as a Roman senator walked past me, she read my tag, "Use as I see fit, don't mind if I do."

She dragged me to the front of the stage and pushed me to face a piece of scenery, I raised my hands over my heads to grip at a hold bar only I could see, she lifted the back of my slave dress and tucked it into my collar. There was no foreplay, no lube, she simply pushed my legs apart and thrust her clit into me. I hadn't been ridden dry very often, I moaned loudly, and then she started to move inside me, luckily I was such a slut, I self lubbed quickly, and then she added a load of come into the mix.

The fucking had started, I could hear the moans as other girls were taken, and my pussy had another clit in it almost seamlessly, it was maybe ten minutes before the first clients decided to join us, with the bouncer standing at the side keeping the numbers manageable.

One client had a whipping post set up, grabbed me and shouted towards the audience, "Runaway would you," he ripped the dress from my body and threw it away, one of his friends rushed to the edge of the stage to collect it, then he manacled my hands above my head and pulled on chains until my feet were six inches off the ground.

The special lash he used produced a great deal of pain, but it left no marks, and I screamed as tears rolled down my face. "More," the audience cried, the lash fell again, "more," after a dozen strokes I made no more sounds, my body was hanging limply, he approached me and pinched my nose, I opened my mouth and he inserted the lash horizontally, I bite down on it, and laughing he said, "let that be a lesson to you wench," and left the stage.

I was taken behind the curtains where the Doctor was waiting, he gave me a fresh miracle injection and over the period of a few minutes, I came back to life. "Good," he said, "let's see how that worked," for the first time with me he pulled out his cock, I gratefully sank to my knees and accepted it.

I returned to the stage with a spunk covered face, "Josie's back," the PA announced, I heard a cheer, a customer rushed to the stage, he grabbed a handful of my hair and dragged me over to hurdle at the side of the stage, his cock, he pushed me over and entered me, he really wasn't very good, and I knew he wasn't very experienced as he came too quickly then withdrew.

I was angry, the whipping and then this ineffectual fuck raised an ire I very rarely felt, "Is that it," I growled as I stood and faced him, "you useless boy, do you need to be taught how to fuck, bend over."

He looked at me slightly fearfully, "Yes ma'am."

"Get that ass in the air and your head down, higher, higher, do you think I'm doing all the work here, get that ass higher," I gave his ass a vicious slap leaving a bright red hand mark on it, "higher."

The reality was dawning on him when I started to lube his ass hole up, he was murmuring about not being sure, but his rock hard cock argued against him. I pushed the head of my cock into his hole, he moaned loudly, a virgin, but I had him well lubed and pushed further in, he started to cry out with regret, "Play with your cock," I ordered him.

I let him get used to the feel of me inside him, and then started to fuck him, slowly and gently at first, he moaned and precum leaked from the eye of his cock, I'd never actually fucked a man before, sissies didn't count, we were really girls, it felt good, he was whining that he'd had enough, I laughed in his ear, "No one's ever had enough at the Salon."

My rhythm was picking up, and I started to give his ass some more work, he was panting heavily, each time my clit fully penetrated him, he moaned, it was very sweet, then I gave myself free rein and fucked him as hard and as fast as I could, he was pulling on his cock with equal abandon and as he came I filled him.

"Clean that up I said," he looked around for a cloth, "with your tongue you silly bitch."

That was my last action of the night, Chrissie was waiting for me after I cleaned and changed, "The last act was pretty angry," she said as we walked back to our apartment.

"I think I might be in trouble Chrissie, did I just rape him?"

She laughed, "You enter the stage at your own risk, everyone knows that, besides he tipped you five grand, I think we can safely say he won't be raising any complaints."

I felt better, she had a strange look in her eye, "But if you're still in the mood for a little rape fantasy, I know just the girl to assist you."

The Birthday Party

Apparently, I had passed another test that long day in the VIP room, I was to be the rich mans present to his son on the occasion of his eighteenth birthday. I stood naked in the main room of the son's suite, except for a pair of heels and around my neck a card, "To Mark (and friends) on his eighteenth, enjoy, love, Dad."

Mark was the first to come through the door, he didn't look at all surprised, the four friends who followed behind him did.

I moved forward, buck naked except for a pair of six-inch patent leather heels, Mark was still taller than me and I had to put my hand behind his neck and stand on tiptoe to kiss him, "Happy eighteenth birthday master Mark."

He pointed to his friends, "James, Phil, Eric, and Tony," he looked at them, "help yourself to a drink boys, we'll call you in soon." Eric and Phil had already sat down, video game controllers in hand, while Tony was opening bottles of beer he had taken from the Fridge. Marks' hand caressed my butt, and was guiding me towards the bedroom door, he was shedding his clothes as he walked.

We were both naked as the door closed behind us, "We're all virgins," he said.

I was already kneeling beside the bed, I took his cock in my hand and guided it towards my mouth, "Not for much longer," I said looking up at him, he groaned and grabbed a handful of my hair as my mouth covered the head, I slowly took more and more of him in, teasing him with my lounge, lips, and teeth, I felt his cock begin to quiver, "none of that young man," I let my fingers squeeze his cock in just the right place, "we don't want to come too quickly."

I went back to my task, I wondered how long he would let me suck him for, "Fuck yeah, arrgghh,oh fuck," he moaned as I pleased him, then his hand pulled my head up, "I think we'll fuck now."

He asked me to lie back and spread my legs, I suggested a few pillows under my butt, then he was in position, breathing heavily but not quite committed, I grabbed his cock and guided him to the entrance of my pussy, "Now honey," he grunted as he pushed about half of his length inside me, a credible effort, his stoke was slow at first, as if he was trying not to pull it out in case he wouldn't be allowed back in. I kissed and encouraged him, and I could see the confidence in his eyes grow, he lengthened his stoke, and began to gradually increase his pace, for his first time he was quite a credible fuck and I was taking a great deal of pleasure from him as his eyes darkened and then his cum filled me, sticky and warm.

I lay in his arms and he kissed me, "Thanks" he said,"that was great, you really are as good as poppa promised me you'd be." I was casually stroking his cock, looking for a fresh erection, he was young enough he should be good for at least a couple more, "Can you call Jamie in," he asked me.

I opened the door, "Master James," I winked at him as he put down the game controller and stood up.

He came through the door already naked and moved to the bed where I had already rejoined Mark, "Stop," Mark said, "You know the club rules Jamie, you know the hierarchy if you want to stand second to me, prove it."

James nodded at him, he didn't look too happy, but he didn't look too upset either, he crawled between Marks' legs and inexpertly began to suck his cock, Mark allowed that to continue for a short while, he had been absently fingering my pussy as he looked down at James struggling on his cock, "Show him how it's done, Josie."

I swung around and took James cock in my mouth, I barely had time to get the whole lot in when he came in my mouth, Mark must have noticed, and forcing James's head down, reciprocated the experience for him.

Mark was to my right, James on my left, James cock was hardening again under my hand, he looked at Mark, who nodded to him, he turned me over and slipped between my legs, his cock didn't slip in the first or second time, on the third attempt he just got the head in.

"Stop," I said, "lean forward and push in as you do," I felt about another three inches enter me, "that's perfect darling, now fuck me," he was enthusiastic, sometimes too enthusiastic, and I had to guide him back in a couple of time, but he fucked me as hard as he could and managed to make me pant and moan a little, not bad for his first time, he pulled out to shoot his cum down my back, and rolled over.

"Club rule," Mark said to me, "only the senior member presents get to come in your ass, everyone else, well," then he brushed his fingers down my spunk covered back, held them up to me and laughed as I licked them clean.

In turn, Eric and Phil went through the same performance, each sucked Marks cock, then each of them fucked me, rather inexpertly. Given the quality of fucks, I received that night young master Mark had got his hierarchy just about right.

He dismissed the others one by one and finally and I called Tony in, he came in still dressed in his casual clothes, "Watch," Mark said to him.

I was on my back, propped up on pillows, while Mark knelt over me fucking my face, little dribbles of silvia mixed with precum rolled down my chin, soon Mark lay down, I reversed myself over him, spread my legs, and guiding his cock into pussy gave a mocking, "YeeHa," as I started to ride him.

Mark looked at Tony, "It's OK T," he nodded.

Tony's cock was soon out and he was wanking furiously as he watched me slide happily up and down his friend's cock. This was the third time he'd fucked me that afternoon and he was getting better and lasting longer each time.

We changed position often, my legs behind my ears, my ankles on his shoulders as he kissed the soles of my feet, Mark standing with my legs wrapped around him, my face to the wall, slam, slam, slam, in and out his cock slid, and I rode the ecstasy with him. Tony was wanking furiously, he'd come at least three times, and he was still pulling on his cock. Mark grunted as he finally came in me again, and I shot over the bedspread as our orgasms merged.

"Who would you rather be Tony, Mark or Josie?"

That was a little unexpected, I looked over as Tony's face reddened and he shyly said, "Josie."

I laughed, with him, not at him or mocking him, "Then you better get on your knees, and use your tongue to clean up that mess young man."

Mistress

I gave Mark a long goodbye kiss, told him to visit me at the Salon, and left with a healthy tip in my purse.