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Train Wreck – Chapter Five

Chapter Five

By Cassidy

After reporting to work the following Monday and beating back the morning attack of vehicles requiring service, I’d been asked to report to the service manager’s office.

“What’s up?” I asked after knocking on his office door before entering.

“Dan,” he said. “I need you to go up to the Collins’s house and pick up their sports car.”


“Mr. Collins called me this morning and said that his daughter is having trouble with it. Take Chuck with you.”

We headed to the house and at the gate I announced myself and then walked up the drive.

I arrived at the garages where Baker greeted me and handed me the keys. “Ms. Collins said that there’s a hesitation when she attempts to accelerate.” His voice would have dried the ocean.

“I’ll tell the service manager. We’ll try to get it fixed and bring it back to Ms. Collins by tomorrow.”

Seating myself in the smallish car, I started it, backed it out of the garage, and then headed down the drive. Margaret appeared at the front door and gestured to me to stop with a big wave.

“I have to apologize to you for leaving so suddenly. I’d forgotten that I had to work the refreshment booth at the boy’s academy. Soccer and football games you know.”

“Oh. I thought that it’d been a one night stand.”

“You weren’t a one-night stand. I have to run, but I’ll call you.”

I watched her butt wrapped in pencil skirt sway as she headed up the three steps that led to the front porch and the front door. The sight of it caused me to re-adjust my seating position.


Margaret’s car had been serviced and returned. I dropped it off with Baker and headed back to the dealership. It’d been a long week and I’d looked forward to a quiet evening alone with a favorite dress.

While sipping wine and seated in my recliner in the un-lit room thinking about Margaret’s comments about our evening, a knock at the apartment door startled me. I flipped on the kitchen light, unlocked, and then opened the apartment door.

“Margaret! What are you doing here?”

“I came to apologize again and offer you a peace offering,” she said handing me a bottle of Australian Merlot.

She wore a little black dress that I wouldn’t dare wear.

“Thank you, but it’s not necessary. Care to have a glass with me?”

Her smile and the little black dress told me that she expected to share it.

“I love your dress. Where did you get it,” she said while taking a seat at my kitchen table in anticipation of sipping her first glass of wine.

“The church thrift shop at Waverly and Green.”

“Really. I wouldn’t have thought that such elegant things found their way there.”

“Who knows, it might have belonged to one of your friends.”

“It could have. It looks like something one of my mother’s bridge partners would wear.”

“Thank you — I think.”

“Seriously, their bridge games are events. I think they’re veiled fashion shows.”

“So I look like an old woman about to play cards.”

“No silly. I’m saying that you look deliciously feminine and….”

“And what?”

“I’d better stop.”

“Stop what?”

She grew pensive as she momentarily stared at the table’s placemat and then faced me.

“This is a first for me. I never met a cross-dresser and it’s confusing me. I don’t know if….” She paused for a moment and picked at the edge of the partly frayed placemat. “I don’t know if I’m turned by it — or you.”

“Would we have ended up in bed if I wore a tuxedo to dinner?”

“I don’t know. Maybe.”

“Do you want to find out?”

“Right now all I want to do is kiss you.”

She moved to my lap, put her arms around my neck, and then began kissing me. Kissing led to foreplay which led to love making which led to exhaustion, and then sleep.

I awoke to the touch of her hand upon my penis. When erect she mounted me.

“I think that you like being on top,” I said placing my hands upon her breasts.

“It seems I do, too — more so with you than with my ex or with others. Does it bother you?”

“Not really,” I said trying to discover what she was thinking through her facial expressions.

“Can I ask you something?” She cooed.

I felt her muscles tighten against my penis. ~ I thought of Jim Morrison’s words “…Wrap your arms around my neck…your hands around my feet…your hair around my flesh….”~

“If I were to ask you to Thanksgiving Day dinner, would you come?”


“What would you wear if I said it would be formal?”

“I don’t know. If something strikes my eye that’s hanging in my closet, I’ll wear it. If not I’ll comb the thrift shops and come up with something special.”

“Could I ask you to come up with a man’s tuxedo?”

“Whatever for?”

“It would be easier to explain.”

Despite my fantasy and the pull of her muscles my erection subsided as we spoke.

“If I come as I am I’m not welcomed, but if I come as you want me to then I’m welcomed.” I lifted her off me, rose from the bed, and then stood over her. “Why should I compromise myself to accommodate you? You already told me that you’re confused by me. Why should I succumb to your current whim when I’ve spent a lifetime evolving to where I am today?”

“It’s not a whim,” she said pulling the sheets up over her firm breasts. “I care for you and would like to spend the holiday with you, but.…”

“But what? You only want to spend it with me if I wear a pair of pants with a satin stripe down the side?”

“Could you compromise just once? I want to know if I’m attracted to the man or the man in the dress.”

“They’re one and the same,” I mumbled while stepping into a pair of briefs.

“No they’re not,” she demanded. “Your manner of speech is much different when you’re wearing men’s clothing. I noticed it when you delivered the cars. It’s overly structured, stiff, and formal. I think that the real you is somewhere in between; and I want to get to know the real you.

The real me. No one ever wanted that. Maybe there was something to her after all.

“I don’t know. I’ll let you know.”

She rose from the bed and hugged me. The touch of her breasts aroused me. We returned to the bed and made love once again. ~ “…Wrap your arms around my neck…your hands around my feet…your hair around my flesh….”~


We saw each other weekly and talked on the telephone daily. When we’d be together it was either at my apartment or in her parents’ house when they’d be away.

“You’re afraid to be seen with me in public aren’t you?” I asked as we took a break from our lovemaking one Friday evening. “It would all be different if I’d wear slacks instead of a skirt, wouldn’t it.”

“Why do you always throw the cross-dressing in my face?” she asked. “It’s like this big defense mechanism. Whenever I try to get close to you…you seem to use it to drive me away. You did it when we first had dinner – thinking that it would scare me off. You’re using it to get out of joining my family and me for Thanksgiving dinner. You probably used it to lose your motorcycle training job.”

“What do you know about that?”

“How unobservant do you think I am? A blind person would realize that you and Tim were at each other’s throats during that course. What did you say? ‘Tim – I cross dress – what are you going to do about it?’ Or was it some other stupid holier-than-thou stance?

I stood silent before her. ~Was this her way to get to know me better, or did she see through me? ~

“Tim and I have fundamental differences and I chose not to follow his mandate.”

“So I’m correct – it was a holier-than-thou stance.”

“Says you.”

“So what’s it going to be — Thanksgiving dinner with me, or sitting at home alone with your alleged principles?”


I watched parts of the Macy’s Thanksgiving Day parade while dressing for the dinner at the Collins’s house. She’d said that there would be in excess of twenty-five people consisting of friends and family. I chuckled as Santa ended the parade, thinking that my opportunity to smoke a cigar and sip brandy in the game room with her father and friends would end the parade that would be my day.

Uneasiness grew as I drove to the house. My experiences with the rich had been limited to brief encounters at the dealership and many of those discussions had bordered on hostile. Their frustrations with the overly computerized micro-processed cars brought out hidden traits. On many occasions I empathized with them. Cars costing in excess of six figures shouldn’t spend as much time in the shop as they’d experienced.

The guard at the gatehouse recognized me and granted passage. The doorman greeted me while the valet drove off with my car. Upon entering the foyer Margaret greeted me. Chambers took my coat while she gasped. I chose to wear a men’s tuxedo with patent leather men’s shoes.

“Don’t you look handsome,” she exclaimed.

“I’m here.”

“Come with me,” she said after a playful slap upon the cheek. “I want to introduce you to my parents.”

As we walked arm-in-arm through the foyer and into the great room she pulled me close and said, “Thank you.”

The great room had been decorated for the occasion and the house staff wore first Thanksgiving pilgrim garb. A tray steeped with champagne glasses had been presented to Margaret and me. We took our drinks and headed toward her parents.

As we made our way across the room I took note of the string quartet as they performed some form of chamber music. I wondered if the violin player would have felt better scorching her instrument with a Charlie Daniels or a Stephan Grapelli tune.

“Dan I’d like you to meet my father, Horace, and my mother, Grace. Dan taught the boys and me how to ride motorcycles this past summer.”

I couldn’t determine if the sparkle in Margaret’s eyes was from standing next to me, the champagne, or from pride in her parents.

Horace Collins was one of the riches men in the country, the son of a sole practitioner small town lawyer who set out to build a major, influential, law firm. Not satisfied with the law, he branched out into accounting and consulting. Using the law and accounting as a base, he ventured into investment and merchant banking with offices in New York, London, Tokyo, Paris, and Berlin.

“A pleasure to meet you, sir,” I said, mustering a firm handshake to match his. “Your daughter and grandsons were excellent students.”

I shook the offered hand of his wife as well. She too had a firm handshake. I held back laughter as I recalled Margaret’s comment about her mother’s bridge playing friends.

“My daughter can be a challenge at times. There had been no logical reason for her to learn to ride those wretched motorcycles with the boys, but she put it in her head that she had to do it,” he said, giving me one of those pat on the elbow approval gestures.

“She did a good job,” I responded. “A little cautious a times, but that’s a good thing.”

Margaret chimed in. “I was awful.”

“It was silly,” Mrs. Collins said. “You competing with that wretched ex-husband of yours for the affection of the children.”

“Mother, please … not now. Dan doesn’t need to hear about that. Come, Dan. I’d like you to meet some of the other guests.”

“Where are the boys? I’d like to say hello.”

“They’re in the home theatre watching football. I’ll get them.”

“Leave them alone — I’ll say hello later on.”

We again joined arms and headed toward the French doors that opened to the patio. The weather didn’t permit they be opened, but the loss hadn’t caused overcrowding. I felt her leg against mine and it started to arouse me. The un-comfortable-ness of the tuxedo coupled with an erection became hellacious.

“I’d like to introduce you to Preston Donaldson. He manages Father’s New York office.”

“Pleasure to meet you, Mr. Donaldson,” I said once again mustering a strong handshake.

I’d met the Ivy League second son years ago while employed at Drexel, Burnham, and Lambert as an arbitrager. He’d been a recent Wharton graduate and his dad got him the job as a budding young trainee in exchange for transferring seven figures into an investment account. Preston immediately established himself as a consummate ass kisser. After landing himself in the position of the last man on a deal team, he worked his way up the ladder with his dad and brother’s political help. He jumped ship when the Securities and Exchange Commission closed in, as cracks appeared in the junk bond market and insider-trading scandals began popping up. Once again his dad’s money saved him, but he had dirt on his shoes and cuffs.

I went down with the Drexel ship. Despite being clean — arbitrage was unethical, but not illegal — my Wall Street days ended. The mere mention of the name Drexel raised doubt.

He bungled his way around the industry and then, after his dad died, used his brother’s influence with Horace Collins to land a job. Hoping that he wouldn’t recognize me, I didn’t relish a trip down a not-so-pleasant memory lane.

“Call me Preston. Aren’t you the car jockey that Horace was telling me about?” he asked trying to belittle me.

“Yes… ah… Preston,” I responded trying not to show that his question disturbed me. “I work at the car dealership.”

“Be nice Preston — I’ll leave you two to talk. I want to say hello to Stewart Long,” Margaret said excusing herself.

“Nice piece of ass,” he said as she walked across the room. “By the way, where did you rent your tuxedo?”

I ignored his question and comment choosing instead to sip some champagne and hold myself back from spitting it in his face.

“I’ll bet her lips feel like velvet when she sucks your Johnson.”

“I beg your pardon?” I asked, using my eyes to drill a hole through his heart.

Sensing my anger, he excused himself.

“Dopey bastard,” I mumbled as he took his leave.

The quartet played Bach as I eavesdropped on the conversations that swirled about me.

The BMW owners Bitch, Moaned, and Whined away about their precious cars while the Lexus, Acura, and Infinity owners regaled listeners with tales of quality and fit. The Mercedes owners mourned the merger with Chrysler as two Rich Urban Bikers quoted passages from the text of the Harley-Davidson biker creed.

When the testosterone level rose to boiling point, I made my way to the freestanding bar to escape it. I exchanged my champagne for Jack Daniels.

Once standing at the quiet safety of the bar I surveyed the grounds through a nearby window. Swimming pool, tennis, basketball, racquet, and squash courts, caretaker’s cottage and a guesthouse dotted the landscape. It all seemed vaguely wasteful. Toys without playmates … playmates without toys. It seemed they were toys for the sake of toys, there because someone could afford them, nothing more. A perfect example of wealth without purpose.

Margaret joined me.

“Having a good time?”

“So far,” I mumbled. “This is new and strange to me.”

“Relax,” she said, kissing my cheek and nibbling my ear. “Father thinks you’re nice and Mother thinks you’re cute.”

“And what do you think?”

“I think you’re hot.” She kissed me with the passion that had been shown when we our lips first met. I could grow comfortable with her kisses as they frightened and excited me.

After our kiss I’d noticed that Preston had observed our actions. His look expressed disgust and envy. Envy that she hadn’t kissed him and disgust because she’d kissed me.

It appeared that he hadn’t changed over the years. The buzz on him had been that he’d been prone to temper tantrums if a deal hadn’t closed or if things had gone wrong with his latest conquest. I controlled my emotions when he’d made those comments about Margaret and my suit in fear of a physical confrontation. My tolerance for sophomoric language would probably crumble should he voice an additional comment.

Chambers announced the start of dinner causing the family and guests to make their way to the dining room. Margaret and I took our seats at the right hand of the Father while Sean and Jason took seats at the left hand of their grandmother.

“Hi, Dan,” Jason exclaimed. “That foot pivot thing you showed me during training really works. Thanks.”

“Good for you,” I answered quite pleased with my performance as a trainer. “It’s a road racing technique. Keep in mind it’s not always used in street riding.”

“Oh I know, but it really looks cool.”

I smiled at him as I sipped some of my refreshed Jack Daniels.

“Hello, Sean,” I said trying to get some kind of response from the morose teenager.

“Well I see that you did get to sniff my mother’s seat.”

“Sean,” his mother and grandmother exclaimed.

“Happy Thanksgiving to you, too, Sean,” I said after downing the remainder of my drink and reaching for the now filled wine glass.

The meal could have been considered the traditional Thanksgiving dinner: turkey, goose, ham, pheasant, venison, and a variety of vegetables coupled with various types of potatoes.

The dinner would be quite different from the ones of my youth. The Collins’s guests remained seated as each course had been served. The holiday meals of my past resembled barnyard feeding frenzies. Platters of food would be placed on a kitchen counter or an auxiliary table and family members would rush to them with plates in hand and scoop gobs of food upon them. In polite circles it would be called buffet style, but in my family it would be a race to the trough. “In the name of the Father, Son, and Holy Ghost, the one who eats the fastest gets the most. Over the teeth and through the gums, look out stomach — here it comes.”

Guests at the Collins’s house chewed their food with utensils placed on their plate while my relatives used them to point in weapon like fashion and talked with their mouths full or with food falling out along with the words they spoke. Dare to put a utensil on a plate during the meals of my childhood and risk losing one’s plate, as it had been the signal that one had completed the feeding process.

They called the soup “wedding soup,” but from my childhood it had been called escarole soup, holiday soup, or tiny meatball soup. Despite longing for a bowl of freshly made pasta buried in tomato sauce and fresh grated parmesan cheese with hot and sweat sausages, meatballs, and a chunk of fresh baked Italian bread, I enjoyed the meal.

To be continued……


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