In Over My Head Ch. 02

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"Well I think you look nice," said the dark haired woman.

The five of them were all about 30 give or take and while not beautiful in the standard of a model they were certainly all very nice looking. They were all clustered around me now but in a strange way I didn't feel at all threatened. They were for the most part very complimentary.

"We are all going out for drinks and since we feel like we owe you, you are coming with," said the blonde.

"Seriously," answered the woman who didn't seem impressed with me at all. "You seriously think that is a good idea?"

"What could go wrong," answered the blonde woman with a shrug.

I gave her a dubious look and stayed put as they started to walk to the elevator. The two sisters, each taking a firm grip of an arm walked me along with them. A large part of me wanted to protest and stay where I was. But a small part, that little voice of self destruction that I dealt with so much of the time when dressed said why not. Besides these two sisters have other ideas. When the elevator door opened I got in with them.

In the elevator no one said much so I took that moment to take a closer look at each of them. They were all nicely dressed for a night out. The blonde and one of the two dark haired women wore short dresses at mid thigh while the two sisters wore slacks. One with a nice sweater and the other with a white jacket over a black shell. The woman that had expressed displeasure with him was nicely dressed in slacks in a more manly way. He thought it almost comical that the most manly dressed person in the elevator was a real woman.

As we got out of the elevator I suddenly realized something. I am not tall for a man being slight of build and just over 5'7". So one issue with passing is that I am not very tall usually. But I was in 3 inch heels. But here's the thing with my present company. The blonde was by far the shortest, but she was only about 2 inches shorter. Maybe. All the rest were taller, even the manly dressed one who was in flat shoes. My height relative to them gave me confidence as we walked into the lobby of the hotel.

Walking through the lobby and into the casino the sisters no longer saw the need to escort me force ably so we all walked along in a group. Them being talkative and loud and me feeling very self conscious as we walked. But a part of me LOVED IT. I was OUT and in public.

I started to feel less confident and calm when I noticed where we were going. Well maybe she is done for the day I though about the mystery woman's sister because we were going to her little corner bar up in the upper reaches of the casino.

"We love this place," said the blonde as we walked in. They found two tables and pulled them together and we all sat. To my chagrin I looked up and guess who was standing there giving me a little wink?

"Well this looks like a fun group," the waitress said. "What are we having tonight?"

"Class of thirteen and MAAC champions," said the blonde proudly. "And we all wants shots of jack and then a Sam's for me."

"Make that a Sams for me too," said one of the sisters with everyone else nodding in agreement. "Or a pitcher. Or two."

"We don't do pitchers here," said the waitress. "But I will stay on top of it. So five shots and five of our finest Octoberfests then."

She left and I quickly excused myself and jumped up to follow her back to the bar.

"Thank you for, well you know," I said blushing. She waved it off with her hand like it was nothing. Two hundred dollar tips do come in handy I suppose.

"I don't suppose my tab is still open, because.......," I said shrugging and holding up a purse that i assumed was empty.

"It is not, but I can easily re-open it no probs," she said with a sweet smile.

No one said anything upon my return as they were all chatting away about nothing specifically but everything in general.

The waitress brought a large tray with the shots and beers and started handing them out.

"Can we start a tab," asked the blonde?

"Already been taken care of," said the waitress looking at me.

"Well see, I told you it was a good to bring....., " Started the blonde. "What was your name again."

"It is Louise," said the waitress quickly. "Louise is her name."

She didn't have to jump in all that quickly because I was just sitting there slack jawed not knowing what to say. But I did like the fact that the boy in the dress was suddenly Louise and not Louie and was being referred to as she. Yes, 200 dollar tips work wonders.

"Here's to Louise then," offered the dark haired woman that was not so keen on having me along.

"And here's to the thirteens, the best fucking team ever," said the larger of the two sisters.

"To the thirteens," they all echoed as they drank down their shots of Jack Daniels.

That night was the most incredible I had ever had. For one night and for what ever strange reason I was one of them. Or at least they were treating me as such and not for any tangible reason, but they were. Or at least for the most part.

What I thought I was involved with was five women that played college basketball together and were having a reunion to celebrate a championship. Turned out I was mostly right as they did not play basketball but their sport of choice was volleyball. Then again what does a dress wearing sissy like me know about sports.

They were not at all what I expected from college level athletes of the female variety. They were all girls and spoke of girly things and I had a great time talking fashion with them. All except for Becca. Rebecca as what most might use as an assumption for the typical female athlete. She was tall and strong and was more or less dressed like a man and for the most part acted like it. She and her friends spoke openly about her preference for females and her dislike for the male of her species.

She didn't much care for me at all. And in one moment when we were alone she told me I was the worst of both sexes. In that moment of open candor I told her that I more or less agreed with her assessment.

But aside from that she was not openly hostile and in all cases went along with treating the dress wearing sissy as just another one of the girls. I think she did it more to humor her friends than to be sympathetic toward me. But she was fine. More than fine.

"Damn, Becks," said the tall dark haired girl in a more than half drunken slur. "I don't think I ever saw you so loose. Don't tell me you had actual fun tonight."

"Fuck you," Rebecca shot back. But then gave her a big hug. "You are the best, Beanie girl."

No one ever explained what significance the name Beanie had and I didn't feel qualified to ask. But these women, they went back and forth going from sharp jabs to loving hugs in a matter of seconds. I had never seen a group so closely bonded. They could say anything to each other and it was laughed off. And it was all so foreign to a person that had never even had one close friend.

What was also both foreign, but in other ways all very familiar was being allowed to live life as he had always wanted. People, particularly men who have never felt the softness of a dress lapping gently at your thighs and knees as it is blown by a warm breeze simply cannot understand the magic in those moments. Being in a dress and proper underthings for a cross dresser is the closest thing to heaven for someone like me. The feel of the soft fabric, the lure of something seen as disturbing or disgusting, and the uncovered appendages covered in hosiery all make a cross dresser feel free and alive.

As someone that had frequently walked in dresses and skirts even on the sidewalks at night in semi-public, well that part is a bit old hat and so very common. But now to do it in front of others in a very public setting. To be wearing this pretty dress and doing it with other women, real women, and feeling accepted was just so very exhilarating. My spirit soared.

As I said I was in my glory. I was dressed and more or less passing. I even had a man ask me to dance. Sure he was totally drunk but still. The rest of the girls all had a good laugh about it. The rest of MY girls.

I was in a place I had never been and not just about being dressed in public. I had never been with the cool girls, or guys, for anything as I had spent most of my childhood and all of adulthood alone. The one lurking in the corner. The one left out. Tonight I was one of them. I didn't know why because I didn't have much to offer, just a cross dresser who loved being a girl, but they drew me in and seemed to accept me anyway.

And damn it, I loved being a girl. They let me be a girl and I think I did a good job of it. But sadly this night couldn't last forever. It was well past 2 AM, the sisters had long since petered out and the beautiful and so very clever "Beanie" had hooked up with a guy and been led away to some high stakes game.

Now it was just the blonde, Rebecca and me getting out of the elevator on our floor. The blonde said good night the best she could and staggered into her room. Thinking that I, myself, should leave now, I started to go. Even though in actuality I had no place to go.

Rebecca grabbed my arm and said, 'I want to talk".

With her grip I was going nowhere so of course I followed her into her room.

She made herself coffee and failed to offer me anything. She asked a lot of questions of me and I answered them honestly. She wanted to know all about my cross dressing and why I did it all and why I wanted to be and act like a girl.

Finally she gave me a funny look and said, "You disgust me, you know that."

It took me aback a bit but I just nodded sadly.

"I guess if I am honest I just want to punch you in the face," she said as she took another drink of her coffee. "Sissies like you need to get beaten up. Wasting a male body like that. I know you are a nice person just trying to do what you feel is right and like, but that is just how I feel. And don't let my friends fool you. Tomorrow they will be laughing at you."

I got up and moved to the door but turned and said, "Look, I understand completely. I don't blame you because a lot of people feel that way. The woman who made me up and sent me out of the room was probably hoping someone would give me a beating tonight. I don't know. I do know she will not let me back in the room."

"Boo hoo," she said unsympathetically then added in a sarcastic tone. "If I beat you up I would only have to explain the blood in the room."

"I am going to leave now and then go down by the back, where the dumpsters are," I told her trying not to cry. "I will wait there for a half hour or so. If you show up there is little I can do to stop you from giving me a beating."

"Don't tempt me, you sissy faggot," I heard her say as I left her room.

At that point I wasn't sure what I would do. It was somewhere around 3 or 4 AM and while the casino operated 24 hours the place would be rather empty. I had had such a good night I wanted to see how I fared by myself. I walked past my room and thought about knocking but did not as I continued on. From there I brazenly took the elevator down to the lobby.

I hesitated in the empty lobby. Do I turn right and walk into the casino and walk around as I was and see if anyone said anything or did anything? Or do I turn left and go out the back entrance and go down where the dumpsters are and see if she shows up. If I did go down there and that woman shows up I am in for a beating for sure.

"What would the mystery woman want for me," I asked myself. The answer was obvious and I went left and down the stairs to the back. I walked out into the cool air of the very early morning. There was a light breeze that ruffled my dress against my legs and it felt so good. It had felt so good to be allowed to be the girl I always wanted to be.

I walked around a bit and saw nothing. I could hear the occasional car leaving the garage or driving past on the road but not much else. The last time I was there was two weeks ago when I was killing time and trying to decide how to get home. I had the same concerns but for some reason they seemed distant and unimportant.

At that moment I was thinking of my mystery woman for the first time most all night. My time with those lovely ladies made me forget all about her. It was now that i wondered what she did on that night. Was she successful increasing the money she had taken from me? I had no way of knowing.

I heard a noise behind me and I turned to get greeted by a fist in my face.

While I used to get frequently bullied and beaten up as a child I had never been in a fight or gotten hit as an adult or even teen. Got bullied some in high school but never got a beating. She hit me hard. I went down to the hard asphalt and knelt there for a moment to get my bearings.

I looked up and there she was standing over me. While I will admit to frequent fantasies about getting beaten up and face punched by a women the reality was no fun at all. I was dazed and hurt and she wanted more.

"Well 'Louise'," I said to myself. "You have always avoided this in the past but now, right now, you are going to get a beating and there is nothing you can do to stop it."

"Get up faggot," she said.

Reluctantly I got up. Which probably was not a good idea.

Even if I could or wanted to put up a fight I was over matched. She was taller, stronger and quite obviously meaner. And to make matters worse for my dress wearing sissy ass she did not like me at all.

She punched me hard in my left breast which stunned me and I backed away and against a dumpster. She followed me and grabbed my dress and started slapping my face. She slapped hard. At first I started to defend myself but instead dropped my hands to my side. She just kept slapping me. Each slap was hard and made my head ring. She obviously didn't care as she kept right on slapping.

What I saw in her eyes scared me as I saw only hate and disgust. She punched me hard in the belly and I went down hard. I was on hands and knees gasping for air. She grabbed at my hair but the wig came off. She threw that on the ground and then took a firm old of my real hair and pulled me to my feet.

She held me by my hair and I tried to put my hands out to protect myself but she just flicked them away and she punched me in the face, once, twice and then a third time.

"Is this what you wanted you stupid little faggot," she said as she spit into my face. First one eye and then the other.

I can say in all honesty that I have often fantasized about having a woman spit on my face as well and she was a good spitter as she delivered quite a load of sloppy spit. I had never really fantasized about getting spit on quite like this however.

She held me up and used me as her punching bag as she punched my face twice more and then simply let me go and fall on the hard pavement.

I lay on the dirty pavement and just cried. She stood over me and grabbed my hair again pulling my head up to meet hers as she bent over me.

"Is this what you wanted you faggot sissy," she told me shaking my head by my hair. "Did you really want to get your face punched in?"

I cried and wept, "No, I definitely did not want this, but I thought you did."

"Oh I did," she said with venom in her tone. "I most definitely did. Now get up. Get up you stupid faggot sissy."

She let go of my hair and let me fall. Eventually I collected myself to stand once again. I stood knowing that I was only standing so she could hit me again and again and make me fall and yet I stood and waited for it.

Rather than another fist to the face she was standing there and roughly trying to put the wig back on my head.

"Are you really locked out of your own room you stupid sissy," she said sternly. "Let's get you up to my room and try to get you cleaned up."

Is this how one is supposed to meet what might turn out to be ones best friend?

Life is strange but if you are someone like me life usually goes well beyond strange.

Tune in next time for Chapter 3.

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FailedscoutFailedscout5 months ago

I strangely find myself drawn to this story even though I wish that there was a lot more compassion in it and a lot less harsh disregard for our narrator. Also the change of point of view in a couple of paragraphs threw me.

Thank you for writing and posting here.

MsCruellaMsCruella5 months ago

A story of contrasts - delightful to read.

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