In Over My Head Ch. 01

The casino was not all that busy and I found a semi secluded table in one of the lounges build a few floors above the casino floor. There were four other people in the lounge, save the bartender and waitress, a pair of older women and a middle aged couple.

I nervously sat in the chair and looked around. The couple talked softly as they romantically touched hands. The pair of women drank their glasses of wine and chatted noisily.

The waitress came over and I absentmindedly ordered a draft beer. She gave me a non committal but pleasant enough smile and left.

Watching the shapely waitress walk away I ran through the grand plan in my mind. I had no idea how any of this would work or if it would work at all. My guess was that the night would be a dismal failure, but here I was trying to make a go of it.

The idea that I could connect with and actually contract a prostitute in this fine establishment was laughable. The possibility that it would be just a regular woman, preposterous.

The waitress, who would have been perfect for the plan based only on appearance, brought the beer and as she placed down a napkin with the glass of beer on top she asked, "Tab?"

The only response out of my mouth was an inelegant, "Huh?"

"Do you want to start a tab," she repeated in a semi irritated tone.

"That would be nice, yes," I responded as I felt my face grow more flushed by the second.

She shrugged and left as so did the couple as they ever so slowly drifted away, close coupled, likely seeking a more private and comfortable location. Her short pleated skirt flapping good by as they left. I envied that woman for wearing that killer skirt and for looking so very good in the process.

I envied him for having such a lovely woman cling affectionately to his arm. Certainly a feeling I had never enjoyed and as dim as my outlook for the future was, not likely to any time in the future.

I was then free to finally get a good look at the waitress as she cleared the table as I was far too flustered while she was waiting on me. Attractive women do that to me as they intimidate me and she was certainly all that.

Her conservative long sleeved white blouse did little to enhance her attractiveness but her short black a-line skirt broadcast her lovely legs. She almost caught me watching her clear that table. She would be so perfect for this because it was clear that she held no interest in me at all.

To my chagrin she walked over to me. I hoped that my face did not blush as bright red as it felt.

"Care for another," she asked sweetly.

I looked down at my glass, which, although I wasn't certain as to how, was almost completely empty. I mumbled a soft, "yes."

She walked away and I tried my best not to have my eyes riveted on the hem line of that skirt as it flipped seductively with each step. And those legs. Whew. A woman like her always made me feel better even if she would have nothing to do with me.

She returned with my glass of beer and smiled again as she placed a fresh napkin on the table and carefully centered the glass, now dripping with condensation, on the napkin.

"Sorry I was snippy before," she said. "It has been a bitch of a day."

"Not a problem," I responded. "We all have days like that."

She turned and left without another word.

'That was the best you could do,' I mumbled to myself. This was the perfect time to strike up a conversation. She was not busy and would have had the time. Well too late you fool. You fail again.

Three men arrived and parked themselves at the bar. They seemed like regulars because the bartender and the waitress immediately started chattering away.

I watched and had to think that those were things I never seemed to ever do. Out for a night with friends and chatting up smiling a woman who seemed to enjoy their company.

My moments of envy and self pity were soon shattered as a purse clattered down on the table and an attractive woman slapped herself into the chair opposite mine.

She smiled at me and with a playful little wink said, "well don't just sit there get me a drink."

I sat there mouth agape virtually unable to speak. I was rescued by the waitress who had seemingly teleported herself from the bar to my table at light speed.

"Can I get the lady something," smiled the waitress.

"Do you have Knob Creek," the mystery woman asked? "I will have that, straight-up if you do. Make it a double."

"Good choice," nodded the waitress who retreated to the bar without another word.

My eyes returned to the mystery woman as my mind going as fast and in as many different directions as a Formula 1 pit stop. I just sat there like a dope and couldn't find anything at all, charming or otherwise, to say to her.

I was getting drawn into her, those dark blue but definitely blue eyes commanding my complete attention. I still had failed to utter a single word. You suck, I said to myself.

She was older than I, but it was hard to tell how old because she obviously took care of herself. She was attractive but not beautiful. Her mannerisms suggested that she was more than comfortable with herself but not to the point of excess.

The waitress brought her a nice glass containing the drink of her choosing, set it carefully on the table and after a little knowing smile to the woman left without a word.

The woman picked up the drink and took a slow almost delicate sip and then another.

"Oh, that is soooo good," she said and with a wink offered, "Thank you for this. It is expensive but well worth it."

'You are probably expensive but again more than likely also well worth it' I thought to myself.

She took another sip of her drink and held it in her slender fingers as she looked straight at me. Studying me. I blushed and tried to look away but those radiant smiling eyes had captured me and and drew me in, commanding my full attention.

My mind raced with a thousand unanswered questions. Surely she was a prostitute because only a professional would bother..... but she was so pretty. So beautiful, at least to me. Surely there were no professional women working this place that looked like her. Surely.

She derailed my train of thought as she leaned forward and said in a low but commanding tone, 'This is the way this is going to work. I will speak and you will listen. I am limiting you to yes and no answers. Nod for yes. Say nothing for no."

She took another delicate sip and continued.

"I have to almost admire your courage for coming in here dressed like that," she continued. "The blouse and slacks are nicely tailored but they are definitely a more feminine cut. But they are well made and well fitting. You wear them well. But then you have probably had a lot of practice. Most men wouldn't know the difference but most women, if they bothered to look, can definitely tell. And those shoes. Well....."

She turned away and made a wave to the waitress who brought over menus.

"We need something to eat because I am absolutely famished," she said to no one in particular.

She placed an order for three appetizers and a bottle of Cabernet before the waitress could leave and then refocused her attention to me as the waitress left to fill her order.

My thought then was, 'OK,she is just using me to get some free drinks and some food and when she is done will leave just as quickly as she came.' But I definitely admired the way she just took over. Just the kind of woman that suits a beta personality like me.

"So, let me guess," she said evenly and almost without emotion. "You started wearing mommy's dresses and slips as a young boy, I'll bet."

I blushed and nodded.

"It's ok, I generally like sissies and girly boys who like to wear dresses. They are usually generous and fun for the most part," she said waving her elegant left hand dismissively.

"Not to mention easy to manipulate," she added with a playful little wink after a slight pause to take another sip of that high priced bourbon.

The food and wine came and she ate most of it and drank the wine. I ate next to nothing and didn't get a sip of the wine. I just sat there watching her eat while she grilled me about my sad virgin life.

Her questions were every where from my virgin life and how I had never even been on a real date with a woman let alone been with one sexually. And, of course, about my fondness for wearing women's clothing.

And then.....

"And of course you have a little bitty penis," she said with a certain amount of delight. "How could you have anything else."

I of course nodded sadly.

She finished eating and said, "That was excellent. Now onto more important things. You do have a room here, yes?"

I nodded yes.

She gave me that little wink and took another sip of the wine and said in a manner that offered no wiggle room for discussion. "I will leave now and meet you in the lobby of the hotel in 10 minutes. You will pay the bill and meet me there."

She got up and picked up her purse and then leaned over and whispered in my ear, "And tip the waitress VERY generously. She deserves it. Besides which, you would kill to be her."

I nodded because all of that was true but the nod was to no one as she was gone in a flash leaving only her sweet cinnamon aroma behind.

She walked away and it was then and for the first time I really noticed what she was wearing as her gaze had held me transfixed for the entire time she had sat at the table.

The bill came and it was $180. I nervously handed her three one hundred dollar bills and before I could say keep the change, she took the bills with a broad almost genuine smile and left me there with only a little sly wink. She sure knew what was up.

I slowly made my way through the casino and into the lobby of the hotel. I had no idea how long it took but hesitantly walked up to the mystery woman. She flashed me that beautiful smile.

"As even a person of low intelligence should be able to gather I greatly enjoy humiliating little losers like you," she said as I got near and stopped. "And like a good little boy, you are going to do anything and everything I tell you to do."

I obediently nodded.

"Immediately and without question," she continued as she started walking to the bank of elevators. "Get us an elevator."

I pushed the button and then she added almost cool detatchment, "When we get in the elevator you will select the very top floor. When the door closes you are to immediately take off those slacks and blouse."

I let out a little nervous sigh but nodded just as the elevator doors parted. We got in and I immediately took off my shirt exposing the top of the dress I was wearing and then pants came off quickly letting dress fall softly to just above my stocking covered legs.

"Cute," she said with a little hint of a laugh.

There I nervously stood, as the elevator seemed to crawl to the top floor. With all walls inside the elevator fully mirrored it was impossible for me to avoid the sight of me in that dress and her eyes dancing with delight as she watched my uneasyness.

The elevator made it to the 21st floor and she got out and I followed. She walked slowly down the empty corridor and I dutifully followed. Clutching my pants and blouse. When we got to the alcove where the soda and ice machines were she pointed to a small silver door.

"That is a laundry chute," she said with a smile. "Your pants and blouse go in there."

With out a question I opened up the flap and first dropped in my shirt and then the pants.

Without another word she walked back to the elevators with a scared little sissy boy close behind, his dress softly flapping at his stocking covered thighs.

She pushed the elevator call button and we waited. When it arrived and those doors parted I almost wet myself. Fortunately, the opening doors revealed an empty elevator.

I pushed the button for 5 and down we went Thankfully this trip yielded no extra stops or added passengers so we got off on floor 5 without any issues.

We walked down the hallway to room 511 and then she held out her hand and demanded, "Card key and wallet, loser."

I placed them into her hand immediately. She opened the door and let herself in but when I tried to follow her she held up her hand.

"Nope, not yet, loser," she said with a wicked smile. "I don't care where you go or what you do but don't even think about showing up at this door for at least another half hour. And then I will consider letting you in. No wait, make it an hour."

She let the door close with a bang in my face.

Of course as a cross-dressing sissy I had always fantasized of moments like this. Trapped, wearing a dress, in a public location. No possible escape. I had certainly done this many times before but this time was a bit different as I was under the control of someone else.

A true sissy wanting exposure and humiliation would have wandered the halls and even used the elevators to go to different floors. But I chose a half hour of hiding in the stairwell of one floor then another. Thankfully there was no activity. Time seemed to drag and the longer I waited the bolder I became.

I was walking down the 4th floor hallway and as I was nearing the soda and ice machines I heard a door open and I hid the best I could. Fortunately the laughing women went the other way to the elevators.

I had no idea of time as it seemed to crawl past so at one point I started counting seconds. After that and another bit of time on my floor three laughing women came bursting out of a room right in front of me. They had been drinking and all of them burst into laughter upon seeing me in my pretty dress right in front of them.

The commotion in the hallway caused my mystery woman to come out of the room and smiled as the women were mocking me. As she came out the women amused them selves by giving the little sissy boy some nice hard face slaps which prompted her to encouraged them.

They were laughing and mocking me as they moved away to the elevator and as I turned I heard the door to my room close. I knocked softly at the door.

"Go away and come back later," she answered from the other side of the door. I could here her laughing as I sheepishly walked away.

After hiding out in the stairwell and hallways she finally she led me into the relative safety of the room.

She sat in the only padded chair in the room and made herself comfortable as she commanded me to stand before her with a wave her hand. I of course eagerly complied.

She sat in the chair and looked me over. Her eyes made me very nervous as they studied me.

"Raise your dress sweetie, show me what you have," she said with an almost reassuring smile.

I fumbled nervously but was able to immediately raise my dress and slip above my waist. She laughed out loud at what she saw because as you see, I was not there to try to hire a prostitute for sex of any kind. I was there to hire a professional lady and take her to my room and expose myself in this pretty dress and then invite her to laugh at me and mock me when she saw my little penis tightly locked up in a metal chastity cage.

"Of course you are wearing diapers," she laughed. "I was expecting to see your pretty panties but how could a loser like you not be in diapers. Pull those diapers down to your knees and show me your little bitty boy penis."

Oh that's right I was so nervous and wound up at this point I had forgotten completely about the diapers. It was difficult trying to pull down my diapers and pantyhose while still holding up the dress. Eventually I got the diapers encased in pantyhose down to my knees and dutifully pulled my dress back up over my waist.

"Ohhhh, how cute," she laughed. "The girly boy is properly caged."

She waved her hand commanding me to turn in place. I of course complied but she complained I was turning too fast.

"Not so fast, loser," she said. "I want to get a nice good look."

I turned slower as difficult as it was with that ball of diapers and hose binding my knees together. All while making sure to keep my dress and slip high above my waist.

I kept turning but each time I faced her I noticed that she had taken my purse from the dresser and now had it in her lap. While I turned she looked through the contents of the purse.

On one turn she held up the bills that were in the purse. I wasn't sure how much it was but it was over $700. She waved the money at me and laughed.

"For me," she mocked as she folded it and stuffed it past her blouse and into her bra. "Thank you loser."

She took out the lipstick and made a note of the shade and then the compact, as she commented, "You have all the essentials here, loser. Good girl."

She took out my license and studied it and carefully placed it on her legs, as she said, "I am going to have so much fun with you tonight, loser."

"But first we are going to play a little game called the pin code game,".she said with a smile as she was pulling my ATM card out of my purse.

"The game is simple, I have 20 guesses to learn your pin code. If I can guess it, I get to use it. And just so you understand, you don't have any choices if you want to play the game or not."

Of course I played the game because as she said, I had no choice. I don't know how many guesses she used but she easily got all four pin code numbers well within the 20 guesses she had. She kept me turning, dress held high and gave a little mock cheer with each number she learned.

She gave me a triumphant smile each time I faced her as I kept on turning. She placed my purse on the dresser as she stood and then, with a combined rush of fearful excitement I shivered as she slipped my ATM card and license into her purse.

Without saying another word she moved toward a wall in the room and motioned for me to follow. I obediently waddled along, dress still raised, diapers and hose around my knees.

She positioned me facing the wall and then produced a casino chip and placed it against the wall at face level.

"Bend and hold this against the wall with your nose, loser," she whispered roughly into my ear. "You are to hold that chip right there against the wall. All the time keeping that dress pulled up high."

"You do all of that while I am down stairs trying out MY new ATM card," she said with heavy emphasis on the 'my'. "I will be back when I bother to get back."

From my position it was impossible to see the door to the room but I heard it open and slam shut.

Holding my face against the wall, holding up the dress, in a totally humiliating and soon to be somewhat painful position I had plenty of time to contemplate what had just transpired.

"You wanted this, and you got it, loser," I said aloud as I chastised myself. "And you are in way over your head now."

It sounds simple, keeping something held against the wall with your nose. It is not. I had to keep my face pressing against the wall to make sure that there was enough pressure on the nose to keep that chip in place.

So not fun position as my nose went from discomfort to painful and my thin girlish arms grew weary. I stood there, fixed against the wall. In silence as seconds dragged on like minutes.

I had plenty of time to think about me and my loser life as I stood there. I had plenty of time to question why I was standing there in the first place. Well ok, I knew why. She told me to, that's why.

I could easily let my dress fall and hold the chip with my fingers and then quickly assume the position when I heard the door opening. No normal person would continue this when there was no one present in the room.

But I am not normal and just a loser that had finally gotten myself into a position where a real woman was dominating me. And dominating me hard. In many ways it was a dream come true. Or a nightmare. Take your pick as I was not sure which at this point.

So of course I remained in positioned against that wall. Both physically and emotionally painfully awaiting her return.