For Their Pleasure Pt. 03

I expected to find Henry when I awoke from the previous night's haze of sex and even more sex. Henry had used me in so many different ways and brought me to climax after climax. He pleased me in more ways than I had ever been able to please a girl when I was Alex. Was I ever meant to please a girl? Or was Alexis always who I was meant to be? The haze started to lift and I realized I was alone in Henry's bed. Naked, of course, but all alone.

There was a note left on a tray, as well as two shots of what looked like vodka. I picked up the note and read it through and through.

"Hey Babe,

Had an early morning meeting. You'll understand. But don't think that means you're off the hook. Your first assignment is this afternoon. And don't be late. Mr. Nail hates it when you girls are late. Better take those two shots before you go. Car's waiting for your cute little ass downstairs when you're ready.

-Henry"

Mr. Nail? Was my first job as a tranny call girl really going to be with a guy called Mr. Nail?

That thought ran constant through my brain as I tried to pick out an outfit from all the stuff Henry got me last night. What would Mr. Nail want to see me in? And then not see me in? Picking out an outfit, and more importantly the right outfit, was definitely something I was going to have to work on. After I picked out a short skirt and the most perfect top to go with it, I decided to pamper myself in Henry's recently remodeled looking shower. I lathered up every inch of my now hairless body, and as I did, I truly felt the real presence of Alexis. She had been awoken inside of me and now was more me than I had ever been. Even to touch my skin in the pure heat of the shower was enough to get me erect. I jerked myself off, figuring it was the best move for the day ahead of me.

After I felt thoroughly clean and now ready to get dirty with Mr. Nail, I slipped on a matching pink lace thong and bra set that Henry had purchased for me the night before. I was nearly aroused again just feeling the soft lace as it started to ride up my tight little asshole. I had to stop and admire myself in several full length mirrors I found around Henry's apartment. Then I finally got fully dressed and got my make up and wig ready for the day's excursion. I appreciated every last drop of the smooth shots of vodka Henry had left me as I grew slightly nervous for my first day as one of his call girls. He was so good to me.

As Henry said, a black car was waiting for me outside of his apartment building. I felt the distinct stare of several men's eyes on my light and slender frame as I walked with a new sense of purpose to the open and waiting door of dark sedan. I climbed in and the driver closed the door behind me and I felt my fate sealed. This was it. This was my new life, as Alexis.

The driver got behind the wheel and smiled back at me, without a word we were off. This was my first day on the job, but it obviously wasn't his. He kept silent throughout the drive, and I appreciated it. I had enough going through my mind without having to make small talk with yet another man in my life. He was cute though, and I liked his little moustache. God, being a girl just a day and some change was already morphing my thoughts and how I saw others. But enough over-analyzing it all. Now I had to mentally prepare myself for Mr. Nail.

The car pulled up in front of what almost looked like a gothic castle. I knew this had to be the place. The driver got out and opened the door for me, his hand practically the size of a catcher's mitt as I placed my hand in his and he yanked me from the backseat. I got back on balance as he whispered coolly in my ear the only words he'd say to me, "Have fun." And in a second, I was back off balance.

He got back in the car and drove off without giving me any further instructions. I stared up at the somewhat foreboding fortress before me and the clack of my high heels rang loudly on the stone steps as I approached the set of double front doors painted a lush red.

A note was stuck to one of the doors, or else I would have already knocked a feeble knock. It told me to enter and I'd find what I needed. I assumed the note was for me, but I soon learned to stop assuming anything about this business. Many others, but certainly Mr. Nail, would soon teach me that.

The door gave way and I hesitantly entered Mr. Nail's world. Just as the note said, I quickly found what I would need, and what Mr. Nail would need and want from me. There was a pedestal set in the middle of a room and on the pedestal, a wooden box. Much like the one Henry had first given me and which had first stirred my curiosity of this new world. With less hesitation than I expected, I opened it. What was inside made me wish I hadn't wasted so much time earlier picking out my outfit for the day, for Mr. Nail had clear designs on what I should be wearing for him. It was a maid outfit.

Not your typical maid outfit, but also not your typical sexy maid outfit either. It was certainly not the kind you paid twenty bucks for on amazon. Mr. Nail had money. And he wanted nothing but the best for his sexy, slender little maid. I ran a finger or two over the silky black material and with even far less hesitation I began to strip off what I had on in favor of my coveted new uniform. I couldn't wait to slip it on and appear as what I had often fantasized of when I had once been Alex, a shapely as hell maid just dripping with sexuality and waiting to be used by her master. It just now happened I would be that maid to be used, and my master, still remained unseen.

I was now down to my pink panties, bra, and heels, quite a sight to be seen as it was. I assumed Mr. Nail must be watching me from some vantage as this was surely part of the show that must not be missed. I quickly learned this was exactly the case. As I reached for my uniform, and was about to dive my tight and hairless little ass inside, I heard a voice echo loudly through the large room.

It was a thunderous, "NO!"

It had the crackle of coming from some type of speaker system. My body froze from the sudden shock of Mr. Nail now finally entering my world. And yet I didn't know quite what he meant by his interjection. I remained frozen until I heard the burr of his voice again.

"My servants shall never wear undergarments. Remove them before further preparing for your tasks."

His voice was rough and commanding, and thoroughly threw me on what had already been a day of new and odd experiences. But I was here to do a job, and wanted to prove to myself, and more importantly to Henry, that I was ready for the task of being that perfect crossdressing companion.

I removed what little still covered me, making sure to take my time as I bent over and slid the thong first out of my crack and then down my softly supple legs. He made no noise of approval, but sometimes, you just know when you've done something exactly right. I was now naked and down to just my heels, which I assumed he still wanted me in as they actually matched the maid outfit and, of course, were designer as fuck.

He had clearly found out my measurements somehow and, tricky tricky, had made sure it was extra snug pretty much everywhere. The black and white silky material was so smooth, and the bust was extra padded so I actually looked like I had a healthy rack. The skirt had so many frills and was so short there wasn't a chance of hiding anything if I had to bend over, and with his firm order to strip all articles of clothing from me, it meant there would be absolutely nothing hidden from him.

Well done, Mr. Nail.

After I slipped into that snug and sexy number, I was off. There was a little duster left for me as well. At first I really didn't know what to do. I mean, should I actually dust the giant globe in the corner? I figured my best move was to be as suggestive as possible with every move I made. Which really wasn't that hard with what I was wearing.

Mr. Nail provided no further instruction, he just watched and did what he did in whatever room he was hidden away in. And what I did was titillate and tease the hell out of him the best I could. I assumed he was the more voyeuristic type and was watching from hidden cameras placed probably everywhere, capturing every move I made. I was worried at first he might be using the tapes to make videos of me or something, but eventually I just got lost in the exhibition of the whole thing.

I walked through a few of the open rooms, which seemed to grow larger and larger as I quested further into his lair. Everything in these rooms was immaculately clean and taken care of, further telling me that my body and my outfit were all a grand show, a show for one. I began to get hard as I caught sight of myself in a few well-placed full length mirrors. These men adored their full length mirrors. This was unlike anything I could have ever imagined, unlike anything I could have ever done as Alex.

I felt him fading farther and farther away from me as my mind started making decisions only a slutty tgirl could make. I'd reach over and dust something super far away, so my body was fully stretched out and exposed. I bent over, constantly, as I presented my perfectly round ass and my dick and balls that would dangle down and sometimes get squeezed between my legs. There wasn't an inch of that place that didn't see my smooth bare ass and hanging balls. I made sure of it.

Eventually I made my way to a long hallway that had at least fifteen doors. I tried each one of them with the same result, locked. That is except for one, the one at the very end of the hallway. The door gave way and I knew I was where I was supposed to be. It was a bedroom, but like every other room in this place, not a soul could be found. Just little old me, little old Alexis.

There was something on the bed, though. As I walked closer I saw it was another wooden box. Another box set to surprise me once again. I opened it without any prodding and found three items inside: a blindfold, a note telling me what to do with the third item, which was a dildo.

The note read, "Leave the uniform on, put on the blindfold, then climb into bed and do what I know you want to with your toy."

To be honest I was a little intimidated. Sure I'd seen plenty of girlfriends from my past use their own dildos to pleasure themselves, but to pleasure myself? Never. But this was a bold new world I was now taking part in. And part of it, I now had to figure, was taking a good sized dildo up my ass. Alex would be screaming and cursing me for even considering this, but he wasn't here anymore, it was all Alexis' decision now.

And so I decided, fuck it. If this was what Mr. Nail wanted, and he would pay me handsomely for it, then Alexis was all for it as well. I grabbed the blindfold and the dildo from the box and climbed into bed. The dildo, a strong and sturdy, and ribbed, shaft was light blue in color. It felt strange in my hand as I was used to the warm flesh of my hard cock, and now as well, the hard cock of many other and older men. I proceeded to blindfold myself and shroud my sight in darkness. The image of the blindfolded sexy maid in bed was one I wish I could observe as well, but this was all for Mr. Nail's delight.

This was the moment. My asshole quivered a bit as I led the head of the dildo along my crack and slowly slid it between my ass cheeks. There was no turning back now as I pressed forward and felt the dildo begin to penetrate and work its way into my tight hole. I began to realize how much I enjoyed my ass being played with as I became harder and harder as the dildo went deeper and deeper. Moans started to escape my mouth as the electric spark of having something inside me once again filled me with ecstasy.

Once it was near all the way in, I realized there was a switch on the end of it. I flipped that switch and the dildo began to vibrate and pulse inside my sweet little ass. I became wet and started dripping cum immediately. My moans grew louder and longer as my world and my ass were rocked by the new sensations I was being exposed to. I began to push the dildo in and out of me as I rode that new toy of mine to pure bliss.

"Oh Mr. Nail. Thank you Mr. Nail!"

I didn't know what else to say to the man who brought a new form of pleasure into my life. No wonder my girlfriends loved these things. They were almost better than the real deal. Thinking of my past girlfriends and what they would think if they saw me now brought me back to where I was and what I was doing. In the darkness of the blindfold I could only picture how I looked, with my ass and cock exposed, thanking and begging for more from a man I still had yet to see and who had me dress as his sexy maid without even a second of hesitation on my part. I was fully accepting it. I was a cock slut now. And I took every order of me with pleasure and a desire to serve.

All these thoughts, as well as the deep and quick thrusts of the dildo filling my insides, finally caused me to cum. I let out the loudest moan I had yet and collapsed on the soft and welcoming bed. The dildo remained rock hard and up my ass, its vibrations a reminder and a tease that it could always out last me. That, if anything else, I was most sure of.

I didn't know what to do as my wits slowly but surely faded back to me. I didn't know if Mr. Nail wanted me to leave, or maybe was expecting even more of a show than the exuberant performance I had just given. If he did he was going to have to wait awhile as I barely felt I could even lift my hand at the present moment.

That's when I heard footsteps. They were slowly working across the floor to the bed, and I knew it must be Mr. Nail. I wanted to reach for the blindfold and finally see the man with the master plan, but then I realized he was the master. And you always wait for master's instructions. The footsteps ceased their echo through the room and I could feel his form so close to me. And yet he still didn't speak.

I curled my body to look as pleasing as I could, pushing out my chest and giving my lips a soft pouty look. I was starting to see what Henry meant about a particular kind of man who would want me in this way. Mr. Nail was definitely a particular kind of man. He could open me up to so many new things and I was eager to explore every one of them. My breathing was still deep from the dildo I had just been used by, as his breath remained steady and firm.

I felt a large hand on my bare knee, and then I felt his other large hand reach for my ass. That's when I felt the dildo being pulled out of me ever so slowly. Once the tip had popped from my opening I let out a sudden, "Oh!"

He put a finger on my lips to hush me. Then I felt his hot breath on my face as he embraced my lips in a long kiss. I thought he wanted more so I began to stick out my tongue for him to take and own as well, but that's when he pulled away and again stood over me. I heard the footsteps walking away from the bed and then, there was nothing. No sound, no orders. After a minute or two I finally removed the blindfold and confirmed I was alone yet again.

There was something on the bed though. Something that hadn't been there before. It was an envelope. When I opened it up, it was filled with more one hundred dollar bills than I could count. God bless you, Mr. Nail.

I left the bedroom and returned the way I came. I made my way back to the front room and removed my uniform, making sure to pose and bend over as much as possible, and delicately placed it back in its box. The clothes I had arrived in, undergarments and all, were where I had left them, and I slowly slipped them back on as well.

Before I left I blew Mr. Nail a kiss. I knew he was watching and wanted to make sure he knew I enjoyed myself as much as I damn sure knew he did. When I left, the same car with the same driver was waiting patiently out front for me. He again opened the door for me as I climbed into the back seat, exhausted but still tingling from head to toe.

As he headed for home, he looked back and said again, "Have fun?"

"Oh yes."