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Train Wreck – Chapter Six

Chapter Six

By Cassidy

There was a break in the meal between dinner and desert as the guests rested and digested.

As I sipped the remainder of my dinner wine in the relative quiet of the home theatre room, Preston approached.

“Dan, you look familiar,” he stated as his eyes examined me from head to toe.

“That’s not likely Preston,” I said, turning my face away from him hoping that he wouldn’t recognize me.

“You know Dan — when you get tired of Margaret – I’ll take your sloppy seconds,” he said with randy eyes.

“Excuse me,” I said as I placed the thumb of my right hand under his chin. I lifted, and his head arched back. “Make one more comment like that about Margaret, and I’ll render you dickless like your hero Milkin.”

I released him and watched as he staggered back into the great room. I’d made a mistake with the Milkin comment as it would probably aid him in identifying me.

The diners reconvened to savor dessert. Pumpkin, pecan, apple, peach, and cherry pies covered the table along with an assortment of fresh fruits and nuts. The dessert wine flowed, as did the espresso, anisette, amaretto, and ouzo.

After dessert, the moment that I’d been waiting for arrived — brandy and cigars with father. The men made their way to the game room to enjoy smuggled in Cuban cigars and snifters of Courvoisier, Grand Marnier, and Remy Martin. The congregation had gathered around the pool table to further discuss business, sports, cars, and politics.

Preston made his way across the room shaking hands and backslapping anyone close enough not to take exception.

“I figured it out, Dan,” he said taking hold of my elbow.

Trying not to show boredom I asked, “Figured out what?”

“Where I know you from. It must have been twenty – twenty-five years ago. You were an arbitrager at Drexel, Burnham, and Lambert. Weren’t you the guy who wore women’s clothing to work one day and got dismissed because of it?” He nodded. “Uh huh. Right before the boat went down, wasn’t it?”

“Some of us tried to keep things going for the sake of our clients, but you’re right — that was me.” I chuckled, trying to diffuse his comment with humor.

“I could keep it quiet, if you know what I mean.”

“Let me see if I understand you,” I said in a tone just above a whisper. “You’ll keep quiet the fact that I cross-dress. What’s the quid quo pro?”

“Margaret,” he said with a devilish grin.

“Hmm,” I grumbled and thought for a minute. “Tell you what. Let’s gather everyone around so you can announce to all that I’m a cross-dresser. Then I’ll announce to everyone here that you called her sloppy seconds and a nice piece of ass — oh, and you thought the touch of her mouth and lips on your Johnson would feel like velvet. Then after the announcement, I’ll reach down your throat and rip out what passes for your heart.”

Preston became dead in the water.

“What’s it going to take to keep you quiet?”

“Nothing at all, Preston. The ball is in your hand,” I said handing him the nine-ball that sat alone on the pool table. “You talk — I talk. You dummy up — I dummy up. You see Preston, I could give a rat’s ass who knows what I wear, or when – but for the sake of today’s festivities, I’d just as soon not go there.”

“What’s going on in here?” Margaret said in questioning tones as she entered the room and looking upon Preston’s drawn face.

“Oh nothing,” I said putting my arm around his shoulders. “Preston and I were discussing which BMW motorcycle would go with his BMW car. Isn’t that right Preston, old buddy?”

“Excuse me I have to talk to Stewart Long about sharing in a possible loan transaction,” Preston said lifting my arm from his shoulder and stepping away.

“That didn’t look like any kind of friendly chat. Are you going to tell me or do I have to tickle it out of you?” she said while reaching under my jacket to stroke my ribs. “Come with me, there’s dancing in the great room.”

“No, not yet. I’ve waited all day to smoke this cigar. It’s loaded with testosterone and I need all I can get. I have to catch up with Preston and the others.”

“Give me that thing,” she demanded while wrestling the cigar from my hand. After taking a few puffs from it and then a sip from my brandy snifter, “If I have to kiss a mouth that tastes like a sewer – you’ll have to as well.”

She crushed out the cigar, put the snifter on the pool table, linked her arm in mine, and then pulled us into the great room.

The musicians had switched to danceable music and many of the guests had begun to stumble through a waltz. We joined them. I reveled in holding her as we danced.

“This is nice,” I whispered.

“What really went on between you and Preston?”

“Preston was going to tell everyone that I cross-dress.” I felt her body tense. “His intent was to humiliate me in front of you, your parents, the boys, and the guests. He wants to date you so he figured if you knew the truth about me, it would cause a break up, and then he could step in.”

“And what did you do?”

“He’s not an altar boy. I reminded him of a few things from his past.”

“Do you know him?”

“We’d met in a former life.”

“Really? Where from?”

“He and I spent some time at Drexel, Burnham and Lambert before it collapsed. Family ties kept him relatively clean while I stayed to turn out the lights and close the door when it ended. I’d almost made it to the end when it all seemed so false to me. To add a bit of integrity, I went to work cross-dressed.”

“How did that work out for you?”

“I don’t work on Wall Street, do I?”

She placed her head on my shoulder as we danced. We didn’t speak all that much and her grip on me softened.

It killed me to have her worried about someone exposing me. I’d gotten by that years ago and had expected more from her.

Between tunes Preston approached.

“Margaret,” he asked. “Care to switch partners for the next dance?”

She agreed and I chuckled thinking about the double meaning of his invitation while taking my leave.

From the safety of the potted palm I watched as they danced. They talked, smiled, and then laughed. I hoped that I would have another opportunity to dance and hold her. Jason and Sean took turns dancing with her, as did her father. Beneath the trappings of wealth beat the heart of a family. ~ Could this motorcycle riding, car humping cross-dresser find a spot in a well-to-do family? ~

Later, Preston took up a position next to me.

“She is a beauty isn’t she?” he asked, as we both watched her dance with Stewart Long.

“Uh huh – that she is,” I answered, wondering why he suddenly switched from passing off-color remarks to compliments. I didn’t trust him and feared that his history of unpredictability would in some way cause her harm.

“Dan … we could be friends.”

“At what cost?” I asked with suspicion.

“No cost at all.” He looked me square in the eye. “I know that you know what I did with — and for — Milken. I was a half step away from an indictment by the SEC and a huge fine or jail time. Everyone on the street knew the deal my lawyers worked out.”

“Uh huh. You sang and Milken took a mini-bath.”

He nodded. “What’s in the past, is in the past.” He extended his hand again. “Let’s try to be friends, okay?”

Margaret joined us before I could answer.

“Are you two at it again?” she asked.

“It’s just ended. Right, Preston?” I shook his hand.

“Right you are. My lips are sealed.”

Something about the way he said that left me uneasy. My cross-dressing wasn’t on a par with bilking widows out of their retirement. He’d managed to make me feel like a co-criminal. ~Further, why should I trust someone who had blatantly broke his fiduciary responsibility to so many by selling them junk bonds that were worthless? ~

“You know what, Preston . . . Margaret,” I flatly stated, “I’m no damn good operating with a sword hanging over my head.” I raised my voice. “Everyone, could I have your attention.” Every eye in the room swung to me. All those Collins who had become important to me smiled.

“Honesty is important to me. I don’t know any other way to live. Preston here was going to tell you all that I’m a cross-dresser.”

Several of the men laughed.

“And he’d be right.”

All the smiles faded.

“That’s my lifestyle and no one is going to make me feel inferior for living it.”

I set down my glass on a tray provided by the quick thinking Chambers, and then walked toward the door.

“How could you,” Margaret called after me. “There’s a time and place, and this was neither.”


Annie popped her head out from behind her apartment door as I made my way up the flights of stairs.

“That’s a different look,” she said gazing upon my tuxedo-encased body.

“Yeah, I guess.”

“What’s wrong? You look like someone just took a dump in your soup. Come on in and tell me about it over a cup of tea.”

“Do you remember the woman who comes over here every once in a while – the one who I went to dinner with?”

“No, but go ahead.”

“She invited me to Thanksgiving dinner and the whole thing blew up.”

“Wait – don’t tell me – you stood up over the after dinner drinks and told one and all that you’re a cross dresser.”

“Yeah, something like that.”

She sipped her tea and then began to laugh. “Well at least you’re consistent. You ruined your motorcycle training career because you thought everyone was doing it wrong and your way was the only way, then you did the same thing with this woman. She probably likes you, but you figured out a way to put an end to it by demanding everyone look at life from the same side that you do.”


Fall became winter, and New Years Eve followed Christmas. There’d been parties, but I’d decided against attending any. The holiday spirit hadn’t arrived.

On New Years day, dressed in a red cashmere sweater, black calf length pleated wool skirt, two-inch heeled black knee high boots, my ever faithful fedora, and a toggle coat, I walked along the snow lined hiking paths in the town park. Snow threatened, but it had yet to break the silence of the day.

As I walked along, thoughts of Margaret entered my mind. She’d never understand why I believed motorcycle training had become dangerous. Nor would she understand why I detested the quid-quo-pro game and those who lived by it. She called it a defense mechanism to drive people away. I called it morality.

The deeper I walked into the park, the quieter it became. The sound of residual leaves crashing to the ground, the footsteps of a wayward squirrel, and the puffing of the down of the chickadees occasionally broke the silence. At times I could hear myself breathing.

To be continued……..


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