In Over My Head Ch. 02

I stood before the mirror and looked at my fresh from the shower naked body. Clear of all body body hair, and of course my eyes focused in on the new metal chastity cage neatly confining what little actual manhood I had.

The cage and lock had arrived in the mail at the beginning of the week. I hadn't ordered it but I was fairly certain i knew who had. She had, after-all, taken a cell picture of my license which contained my address so the origin of this newer cage was obvious.

It was a steel cage and while the part that tightly encased my little penis was smaller than the old plastic chastity device, this one was significantly heavier and a bit bulkier. When it arrived I of course put it on immediately and worn it to work the past two days. It was surprisingly comfortable most of the time given its weight. If there was much of any stimulus applied to my weak brain it became pretty uncomfortable but then again that was the whole purpose, was it not.

The week before had been a constant battle with myself over what I should do about the impending "date" with the mystery woman. My rational brain of course told me to flee, but that was being overridden by my more powerful weak and submissive side. When I put that new chastity cage on there was little doubt that I was going to follow through with the meeting on Thursday. As if there was all that much doubt.

One more look at the effeminate reflection in the mirror and the decision seemed simple. Even though any doubts I had about what awaited me, it was obvious that i was going so it was now time to get dressed and just go. Sure the day and night were almost surely going to be humiliating. But being who I am only tended to excite me to the point where that cage was starting to get uncomfortably tight.

I chose to put my bra on first. It was a slightly padded b-cup in lilac. The treatments had been progressing so well I now had breasts that filled an A-cup. Needing the excitement of it all I wanted the small bumps in my chest to be noticeable. Next to be put on was the diaper and suntan shade pantyhose. I simply love the feeling of a nice silky hose as they are carefully stretched over my legs. How great they made my legs look was a bonus. The hormone treatments had been working well and as I scanned myself in the mirror my hips and waist seemed more clearly defined. I covered it all over with a full slip, also in a soft lavender.

I had 4 dresses to try once more as each had been given a test run during my after dark walks. They were all new and I loved them all so it was going to be a tough choice. I has noticed that my closet tended to feature conservative shades and modest prints so when I went shopping this time I went for bold patterns and bright colors.

Dress one was a silky pleated number in a light pink print with bright flowers. It had frilly cap sleeves and a tie at the close neck. The dress hung right at the knees. I did worry that my blouse might not cover up the tie collar. The print was bold and bright and would never be confused with anything manly.

The second dress was a soft wrap dress with a double tiered skirt and a v-neck. The sleeves were longer but soft and full. It was shorter, about mid-calf, so of course I couldn't wear this slip with it. It was a solid lilac color which simply flourished with color. This dress showed a lot of his legs and arms which I liked.

The third dress was a simple v-neck dress with a very full skirt in a hot pink and white print that didn't shout dress, it screamed it. The sleeves were short, exposing my thin girly arms quite nicely. The dress hung a few inches above the knees so my slip peeked out seductively about a quarter inch below the hemline. I watched myself do a few twirls and loved the way the dress flowed around my legs.

The fourth choice was a simple dress in a stunning print of small flowers and designs in multiple shades of purple and white. I liked it in the catalog and loved wearing this dress. It wasn't elegant or fancy but oh that print. I loved all of those pretty shades of purple. Purple shades were my favorite and this dress featured them all. It had a round neck line and large flowing short sleeves.

I love soft full and flowing sleeves on dresses because they made my slender weak arms look even thinner thus emasculating me completely. The dress hung just below the knees and was full enough that I could add the frilly half slip or the petticoat or both.

Feeling the moment I tried on an extra dress, a pleated v-neck dress in a very bright and bold print of pastel purples, lavenders blues and whites in random splotches. The pleats danced softly at the knees. I had taken a long 2 hour walk on the streets in this and loved the feel of it. I had more than one passing motorist give me a friendly toot of the horn. The trouble was it had long full sleeves and I was certain that it would be hard to cover it up with even a long sleeved blouse.

Choice number 4 was it and I pulled on the lavender petticoat and covered it all up with a royal blue pair of slacks with an elastic waist band and small slash pockets. It had wide legs and no fly and was obviously women's slacks. I covered up the top with a light blue button down blouse that was left to hang just over my hips.

I slipped into my women's loafers with a 1 inch heel and before I could think all that much about where I was going and what I was about to do I was driving to the casino.

The casino hotel room was booked so all of the hooks were set. As I was pulling into the parking garage of the casino I realized in my eagerness I hadn't brought any other clothes with me. Not even a back up dress.

The valet took my keys and drove off in the car and surprisingly I walked into the lobby of the hotel portion of the complex confidently. I registered for the room, the same exact room as last time and went up. I put all of the cash and my ID's in the safe and looked around. It was only 5 PM. This fairy boy was so very eager.

I eagerly went to the same lounge area anyway despite being about 3 hours or more early. My mystery woman hadn't specified an exact time so who knew.

I found a nice little table in an out of the way location and sat. The same waitress walked over. I nervously watched her approach. Dressed in her uniform of a white blouse and black mid-thigh skirt she moved with a certain powerful grace that I hadn't noticed last time. Then again I was massively on edge last time.

"Drink," she asked in a pleasant tone?

I stumbled out an awkward request for a beer. To which she laughed and said, "Do you actually care what kind?"

I blushed furiously and said with all the savior-faire of a three legged dog trying to lift a non-existent leg to piss, "Any light is ok."

Ok, ok, OK, not smooth. Then again I am never smooth. Regular women intimidate me, while attractive women turn me into a molten puddle of goo that cannot put even the most simple of sentences together. She was all of that and more.

She walked away giving me no sign that she recognized me from the last time. Hell, that was two weeks ago and you are a man completely unforgettable. She must see a thousand people in a week working this job, so why in the world should she give you even a second thought. Besides, it is probably a good thing.

As I watched at the bar I began feeling less and less comfortable. Everything I wore was designed for women, real women, not a fake one like me. All that material of the dress and slip and petticoat were bunched up in the legs of the slacks and that had to be noticeable and the pant legs were up high enough so my hose covered ankles sticking into women's shoes was clearly visible.

And now that I think of it, I felt like those little b-cups were pushing out through my blouse in Dolly Parton-esque fashion. By the time she came back I was a mess.

Her casual smile relaxed me a little as I started a tab on my hotel room and declined anything to eat. I was far too nervous at that point to eat anything.

I was trying my best to settle back in but the dress, slip and petticoat seemed bulky and far too visible beneath the slacks and blouse. "Relax," I said to myself. "The woman behind the desk at check in didn't seem to notice and the waitress didn't seem the least bit concerned or even interested. So try to rel......."

She placed her hand on my shoulder and said softly, "You are early. Very early and very eager it seems."

The mystery woman sat across from me and smiled sweetly. I almost jumped out of my skin as the waitress mysteriously appeared and placed a glass with an amber brown liquid in it and left just as quickly.

She picked up the glass and took a sip and smiled triumphantly at me. She crossed her elegant legs beneath a knee length slim skirt in a grey tweed giving me the impression that she was pleased I was there. At least that was the mood her body language spoke.

Her eyes played amusingly on me as I watched the waitress leave. She gave me a little wink and said almost casually, "She is my sister. Just for the purposes of full disclosure. She doesn't know what went on between us but....." Her voice trailed off as she took another drink. "She did comment on your excellent choice of clothing, however."

She leaned back in her chair bounding her right foot clad in an elegant looking high heeled pump in dark grey and swung her purse from her shoulder onto the table. She pulled something out of it. She then laid my bank card on the table and tapped it lightly.

"It was nice of you to leave this active," she said with a little smile. "I used it a few times, but I don't really need your money. But you do of course know that it is important for us both that I keep it and you keep obediently depositing your pay checks. Don't you agree?"

I said nothing and simply looked back drawn in by her attractive face and demeanor. She took that as acceptance and slipped the card back into her small but very elegant purse.

"You are here because you want and need what I offer," she continued. "And you definitely amuse and entertain me. So I think I will keep you."

That last line seemed to amuse her as she drained her glass through smiling lips.

"That is a very handsome blouse," she said as her eyes scanned over me. "It will be a shame but you know what has to happen to that blouse. And those slacks as well."

I blushed brightly as I knew that both blouse and slacks would be sliding down a trash or laundry chute sooner or later. She leaned forward lightly and continued, "Hopefully there is an equally pretty dress under that blouse. Unbutton that blouse and let me have a peek. Right now."

I looked at her and then looked around nervously. Her eyes and sly little smile simply said "Do it"

She confidently leaned back in her chair and I of course reached up and began at the top button slowly unbuttoned my blouse as she winked at me. I was afraid to look down as I could feel the blouse opening slightly and with only two buttons left closed she waved for me to stop.

I looked down briefly and could see the bright print of the dress almost glowing through the opening in the blouse. She smiled and voiced her approval, "Nice pretty dress, dear."

"I agree," said a familiar voice to her left. "Very pretty indeed."

As my focus was on the smiling eyes of my mystery woman I hadn't noticed that the waitress had arrived and was placing another bourbon on the table as I was unbuttoning. Well hell, she already knew so why not her too.

She said nothing else and smoothly glided away.

"Very good," cooed the woman. "I like an obedient boy."

I held my hands up by the buttons hoping she would allow me to close them but she said nothing else as she took a little sip of her drink. I let my hands fall helplessly to my sides.

She moved to get up and when standing she took her drink and her purse saying, "You know where to go and what to do. I will see you in about 10 minutes or so."

She started to walk away and then over her her shoulder she added with a smirk, "And keep that shirt unbuttoned. You look cute like that."

The waitress was over right after she left with the bill for me to sign. I added a $200 tip to the bill. She gave me a little wink of thanks and left me there staring down at an untouched beer.

The walk through the casino was very nerve wracking but I walked, with the blouse slightly open at the top. I tried my best not to think about what anyone could or could not see. I found her in the lobby, standing in that very impressive grey business suit. When we got into the elevator I handed her the card for the room and the blouse and slacks came off immediately.

"I do like an eager and obedient boy," she said as the elevator rose to the top floor.

We went to the housekeeping room on that floor and she opened it. It was then that I noticed that she had a card key for the room. I wondered how she had come to have one as I deposited my blouse and slacks in the chute and watched them disappear. She was already out of the room and walking away.

"One hour, and then come to the room and we shall see if I decide to let you in," she said with a smile. She left me standing there in my dress.

"That dress is killer," she shouted out as she approached the elevator. The elevator swallowed her up and she was gone.

I heard a door opening down the hall and I scurried to the relative safety of the stairwell to hear an arguing couple leave their room and summon the elevator. I stood there in that lovely dress and asked myself almost aloud, "What the hell are you doing?"

I did my best to try to track the time but had no idea how long I had been trying to hide out while fully femme. Thankfully I had seen no one. Or more importantly had not been seen by anyone.

As I was approaching the door 4 lightly-intoxicated women came frolicking out of the elevator. They saw me and all burst into laughter. The had me pose for them and model my dress for them and they all had a good laugh. They loudly complimented me on my dress as i nervously glanced around to see if any other guests would hear the ruckus and come out to investigate. Thankfully they were bored taunting a sissy in a pretty dress and walked away to their rooms.

When the hallway went quiet I contemplated if I should try to knock at the doom to my room requesting entrance. As an answer to my internal questions the door opened and mystery woman stuck her head out.

"Now wasn't that fun," she said barely containing her laughter. "Come in I have a surprise for you."

I walked into the room not knowing what to expect. I was greeted with nothing out of the ordinary. She ushered me over to stand before her and I was once again modeling my look. Lifting my dress and showing my diapers and then my little caged penis.

"I knew it would fit perfectly," she said. "It is definitely you. She produced a different lock and keys and locked it on. "That little penis is MINE now," she added almost triumphantly. As if it wasn't hers to control completely prior to that.

She had me open the safe and I got out the envelope with the cash in it. I had thought about giving her only some of it to begin with but of course she got the entire contents of the envelope.

She fanned out the 100s on the little table and smiled. "Very nice," she smiled. "Given your eagerness to please I have a surprise for you."

She pulled a nice woman's wig from the bag at her feet and within moments she was fitting it to my head. It was a very well made piece in a deep mahogany color that danced nicely at my naked neck and on my shoulders. I looked into the mirror and almost fell in love with the person looking back at me.

When she was done with her makeup kit I was definitely in love with the image in the mirror.

"Such a sweet looking boy," she said proudly. "Of course you know what this means for you tonight my sweets."

I thought about it and knew exactly what she meant. I wasn't going out dressed and wigged for a walk in the darkness. She was going to send me out into the hotel and casino. I took another look at myself and wondered just how "passable" I really was. She didn't seem the least bit concerned.

She reached into her bag and pulled out a nice pair of mary janes with about a 2 inch heel. She could see by my face that I loved them. I tried them on and to my surprise they fit wonderfully. If anything they were a half size too big.

"Walk in them and see how you do," she said seemingly proud that she had completely hit the size spot on. "I am not sure how you will do with a 3 inch heel so those are a 2-inch, but it looks like you do just fine. Practice does make perfect I suppose. Now try these."

She took out a pair of square toed mary janes with a 3 and a half inch heel and I loved them when I put them on. They were so very comfortable as they fit perfectly. She complimented me on how well I handled the higher heels but I love heels and have spent a lot of time walking in them.

"You can, of course, keep all of these shoes because I certainly didn't pay for them myself. I used MY new card to buy them and they will not fit me," she said as a I modeled the shoes for her. I was really enjoying this part. Trying to put off in my mind what she had planned for me.

She then reached into the bag and said, "You are going to freak when you see these because of that dress you have on."

She was right. I freaked. She pulled out a pair of sling backs with pointed toes and a thin 3 inch heel. In purple. A purple that matched my dress perfectly. I of course tried them on immediately and they also fit perfectly.

"A perfect match," she said proudly.

"but how," I thought to myself.

She produced my wallet from her purse and laughed, "Remember this? There is so much information in here. So I knew just what you were looking at and exactly what you purchased. So I knew your shoe size and I knew you bought THAT dress. I was hoping that you would wear it. But then again my little sissy, how could you resist."

"You know what comes next right," she said with a little grin. "We both go out. You go your way I go mine with this debit card to use. You are not welcome back into this room. Maybe I will let you back in at 7 or 8 in the morning. If I bother to wake up that early. Then again it might be easier to get home in the dead of night in that cute little dress and matching heels."

She reached into the bag and pulled out a small purse in black with a shoulder strap and tossed it to me.

"Now get out of my sight you flaming fairy," she said firmly.

She was laughing when I exited the room.

I got out into the hallway and didn't know what to do. I walked toward the staircase but before I got there a door opened and two men walked into the hall. They both nodded respectfully, one of them giving me a little smile, and they continued on their way to the elevator.

"Damn," I thought. "I just might be able to pull this off."

My reverie was broken when yet another door opened and right there were two women, one of whom had been in that group of four that had confronted me before.

They smiled at me and then they were quickly joined by the other three.

"Oh look girls it is the queen of all sissies," she said mockingly.

"Oh give it a rest, Mags," said one of the two black women behind me. "He isn't hurting anyone."

"And he looks kind of cute," said the blond to my right as her roommate was closing the door to their room. "You are just jealous because he is wearing a prettier dress than you are Maggie."

"Oh fuck you," said the woman obviously named Maggie or Margaret. "He is better dressed than all of us."

"Sorry about before," said the black woman. "We were just having fun."

"What did you do sis," asked the other black woman?

"We were just teasing the boy a little is all," the blonde woman answered for the sister. "He has to expect it, i mean at least a little, going out dressed like this."