Close this search box.

Train Wreck – Chapter Four

Chapter Four

By Cassidy

We employees of the dealership decided to work in costume on Halloween. Everyone laughed when I showed up as the Wicked Witch of the West sporting a green face, stick on warts, big nose, pointed hat, broom, and a black dress five sizes too big for my size fourteen frame. The impromptu costume contest winner ended up being the service manager who dressed as a pregnant Mother Theresa.

With no deliveries I spent most of the afternoon as a valet. Margaret Collins drove her two-seat sport model up the drive.

“Dan is that you? You look hideously gorgeous,” she said with laughter just short of tears.

“Yes, it’s me,” I said through a smile that included three blacked out teeth. “How may I help you?”

“My windshield washer fluid level light came on and I wondered if one of the technicians could top it off for me.”

“I’ll do it – pop the hood.”

“No don’t,” she grinned, while checking her vanity mirror and tending to her disheveled hair. “I wouldn’t want you to get your dress dirty.”

“I’ll be careful.”

As I placed the top back on the reservoir, she accidentally sounded the car’s horn. It startled me and caused me to bump my head and bend the top of my hat on the hood of the car.

“What the fu…? Dumb bitc….”

“I’m so sorry.”

Her apology caused spirits to rise from the grave, just listening to her voice.

“I reached for my cell phone and my elbow touched it.”

I closed the car’s hood. “You’re all set.”

She pulled away, stopped, and then backed up. “Have dinner with me tonight?”

“No, not tonight. It’s amateur night like New Years Eve and St. Patrick’s Day. I don’t want to be out on the street with a bunch of drunken fools and neither should you.”

“Tomorrow then?” she asked in anticipation.


“Come to the house. The boys are still in school at the academy and my parents are in London on business. It’ll be just the two of us.”  She threw me a smile. “Eight o’clock, then. And, one last thing — dinner’s formal.”

After checking her hair in the mirror one more time she drove off. With my witches hat in one hand and an empty bottle of wash fluid in the other I mumbled, “A dinner date.  That should be interesting – could turn out to be an awkward evening talking about learning to ride a motorcycle, but maybe….”


“What to wear – what to wear – what to wear,” I said as I looked through my bedroom closet. A formal dinner — just the two of us — with probably a servant or three. The man tailored woman’s tuxedo . . . the red silk empire waist gown with its crinolines . . . the hand painted Japanese styled dress . . . the mid thigh length black satin and velvet strapless cocktail dress . . . the blue sequins gown with its white chiffon boat neck  . . .  or jeans and a sweatshirt. Whatever I wore, I wanted to look and feel special.

With the exception of the witches costume she’d only seen me in the dealership’s uniform of a blue oxford shirt with the logo and navy blue slacks or the state’s motorcycle training long-sleeved t-shirt and jeans. If I showed up wearing the cocktail dress the worst that could happen would be that she’d ask me to leave. The words weirdo, freak, faggot, sissy, and he-she had all been heard before. The battle to dress full time en femme had been won years ago. If it offended her, then so be it.

I descended the four flights of stairs wearing the black satin and velvet dress with fish net stockings, three-inch heeled black suede pumps, opal bracelet and rings over black satin elbow length gloves, earrings, necklace, black velvet clutch bag, honey-blonde shoulder length loosely curled wig, and a mink stole draped over my shoulders.

“Don’t we look yummy tonight,” Annie said. “I wish I could wear a dress like that.”

“Be thankful you can’t. It’s a size fourteen.”

“Where are you off to this evening?”

“I have a date with the woman I told you about. You know, the one from the course?”

“You’re going on a date with a woman dressed like that?” she asked, her tone somewhere between shocked and astonished. “Does she know about this part of you?”

“You know me. This is who I am, take me or leave me.”

“Aren’t you asking a bit much of her on a first date?”

I shrugged and she returned it with one of her own.

As she closed her apartment door, she said, “Have a good time.”

My stylish appearance contrasted greatly with the twenty-year old Monte Carlo I drove to the Collins’s Mansion. A startled guard announced my arrival.

The doorman greeted me, opened the car door, escorted me to and through the front door to the foyer, and then departed, leaving me alone. A moment later Margaret entered the room swaddled in chiffon and dripping in diamonds.

“Dan?” she asked, her face registering shock and something else I couldn’t quite read.

I was ready to leave the minute she raised an objection.

“Chambers, please serve the champagne,” Margaret said regaining her composure. “I could use a drink.”

“I could use one too,” I said awaiting her verdict with some anxiety.

“Halloween was yesterday,” she said taking a glass from the tray that Chambers held in his right hand. “Why are you dressed like that?”

“This is the way I dress during my non-working hours. I’m a cross-dresser,” I said accepting a glass of champagne from the tray that had been placed before me by an openly distracted Chambers.

Between gulps she said, “I would’ve never expected this.”

After draining the first glass she motioned Chambers to refill it. With the world set right with Moet and Chandon she seemed able to move on. “Chambers please take Dan’s wrap and serve the hors de oeuvres and champagne in the study.”

The crinolines beneath her pale blue, floor-length, chiffon gown coupled with the clatter of our heels against the tiled and then oak floor broke the decreasing un-easy silence that enveloped the foyer and study as we made our way arm in arm.

“Chambers,” Margaret said. “Leave the bottle. Dan and I want to share a quiet conversation.”

“Yes Ms. Collins,” he responded as he backed out of the study, closing the two mahogany study doors in the process.

“Have you ridden a motorcycle since taking the course?” I asked while sipping my champagne.

“No, but the boys rode all summer. When their father arrived, the three of them rode the fire roads and trails that surround the vacation house.”

As she spoke, she seated herself on one of the leather couches, and then gestured to me to take a seat by her side. I watched in envy as her gown engulfed it. One day my wardrobe would feature such a magnificent dress.

“Is that why you took the training course where you did?” I asked following her lead toward a “normal” conversation.

“That training site was only thirty minutes away from the vacation house.”

“Do you stay at the house when he arrives?” I asked. ~ What was more exciting, sitting next to her dress — or what was in it.~

She slid closer to me. “No, – I come back here for the week. I’m not at all interested in the women he drags up there when he’s with the boys.”

“Was the divorce amicable?” I asked, wondering if Chuck’s story had been valid.

“It was horrid.” She placed a hand on my cheek to position my face toward hers. “I felt bad for the boys, but they’re getting used to the idea. At first they blamed me, but then realized that their dad had a string of women; and when they found out that he’d beaten me, they refused to see him at all. I had to force them to spend the annual week with him — after all, he is their father.”

“What about you? Do you have a string of well to do bankers, attorneys, and accountants beating down your door?”

“I date occasionally.” She shrugged. “No one special.”

There was a knock at the study door, and Chambers poked his head into the room. “Ms. Collins? Dinner is served.”

We headed toward the dining room. In the center was a table that rivaled the flight deck of an aircraft carrier.

When Margaret had been seated, a napkin placed on her lap, and after filling our wine glasses with the first of a variety of different wines, Chambers took a statuesque position near the sideboard in anticipation of serving the first course of our dinner.

“So what possessed you to ask me to dinner?”

“It’s my way,” she paused to take a sip of wine “of saying thank you for helping the boys and me when we learned to ride.”

“Where’s Tim?” I chuckled.

“He’s a bit over the top, isn’t he? Your opal earrings are lovely.”

There’d been more going on with her look than just earring envy.

“Thank you,” I said simply. “Speaking of the boys, what was Sean’s problem?”

“He was embarrassed by my presence. He’s trying to be grown up, but at times he’s still a boy.”

After the appetizer of stuffed shrimp followed by Manhattan clam chowder, our main dish of filet mignon, potatoes, broccoli, and salad had been served. The desert of chocolate mouse brought the meal to a close.

Each course had its own special wine and by the time the aperitif and espresso had been served, I’d become quite light-headed.

Even though my appearance bothered him, Chambers performed his duties and demonstrated the courteousness of his station.

“At about this time, my father would invite the men to accompany him to the game room for cigars and brandy. Would you like to do the same?”

“I’ll pass on the cigar and say ‘yes’ to the brandy. I would like to get some air. – Care to join me?” I folded my napkin and placed it on the table while attempting to rise from the table without falling off my heels.

“Chambers, please get Dan’s mink and bring mine as well – we’ll be going out to the patio. Serve the brandy in the study and please draw the patio drapery.”

He returned with the furs and helped Margaret with hers, while leaving me to fend for myself.

As we stood amongst the moon shadows she turned and kissed me. I kissed her back. She submerged her tongue into my mouth. We held each other tight. I hadn’t been kissed in such a manner – or even kissed – in a long, long time.

“Mmm,” I moaned as we broke our embrace.

“That was delightful. I never kissed a man who wore lipstick. For that matter I’ve never met a man who could look better in a dress than me. It’s funny, after the initial shock of seeing you as you are; I haven’t given it a second thought. Shall we go to the powder room to repair our faces?”

Arm in arm, we re-entered the dining room and made our way to the study where a bottle of brandy and two snifters awaited us.

“The powder room is through there,” she said, pointing to a door behind a teak desk and high backed leather chair.

I repaired my face, returned to the study, and then took a seat on one of the couches that faced the gas-burning fireplace. She joined me shortly thereafter.

“Where’d you head off to?”

“I went to my private bath to repair my face. It would be awfully cramped in there with the both of us jockeying for mirror time.”

“Yeah, right.”

“This is nice,” she cooed as her head rested upon my false breast and her arms around my waist.

“I’d better be going. It’s getting late,” I said, freeing myself reluctantly from the welcomed capture.

“Stay the night. You’ve had a fair share to drink and I don’t want you to get stopped or risk an accident. The motorcycle course classroom trainer said that we should know our limitations and I’m quite sure that you know yours. Chambers….”

“Yes, Ms. Collins,” he said, re-entering the study.

“Please prepare a guest room for Dan. He’s staying the night.”

“Yes Ms. Collins.” Chambers’ professionalism had been in high gear as he responded to his employer’s request.

I poured us one more brandy and then re-took a seat.

“Dan,” she said. “I have to admit that I thought about you quite often after the class. In fact I was tempted to have one of Father’s investigators hunt you down.”

“Why didn’t you?”

“I didn’t want Father to interfere. He’s grown quite protective since the divorce. When I saw you in the drive the other day I believed that we were destined to get together.”

“So fate dealt us a hand?”

She gently stroked my cheek with her hand. “Fate can be so kind.”

When we finished our brandy she led me to the guest room and then headed off to her room.

I undressed and retired to the bath to remove my make-up. With the ritual complete I turned out the light and crawled into the down-turned bed. Pajamas that appeared to be unisex had been placed at the foot of the bed, but I chose not to wear them, electing instead to sleep in my Haines briefs. “…falling, yes I’m falling….”

Bathed in the glow of the light from the room’s fireplace, I stared at the ceiling wondering about the difficulties involved in dating a wealthy divorcee. Her kisses told me that this had been more than a thank-you dinner. Her parents’ reaction to her dating an employee of a car dealership, coupled with the openness of my cross-dressing, would surely be a cause for heated discussion.

The door opened and Margaret entered the room dressed in a navy blue cathedral-length nightgown. Its plunging neckline revealed a sufficient amount of breast to excite.

She crossed the room and crawled into my bed — placing her body upon mine amidst a barrage of kisses.

“You’re attractive dressed in a t-shirt and jeans,” she moaned as she searched my body. “You’re absolutely erotic cross-dressed.

We spent the remainder of the evening taking turns as the aggressor until exhaustion took its toll.

I awoke alone. A note had been taped to the bath mirror.


I’m off to see the boys. Wear this warm up suit and this pair of pool shoes for your drive home. Use the tote bag by the foot of the bed to pack up your dress, etc.

Speak to you soon.


“What the hell happened?” I asked my reflection in the mirror.

Once home and after showering, shaving, applying light make-up, and then dressing in a cable knit off white sweater, gray “A” line calf length wool skirt, one-inch heeled boots, and a gray fedora, I took a seat at my kitchen table, and then prepared a shopping list.

As I wandered the aisles of the grocery store looking for food and other necessities, thoughts of the dinner filled me. She had magnetism. A relationship with her would be an absolute joy, but the baggage could be troubling.

To be continued….


2 Responses

  1. Oooooo, that was well worth waiting for!

    We need more like Margaret Collins in the world – it’d be a far more fabulous place!

    Looking forward to next Monday already!

Leave a Reply

Your email address will not be published. Required fields are marked *

Featured Posts

Get The Latest Updates

Subscribe To Our Newsletter

Sign up for the first look at Kandi’s outfits, blog posts, and product recommendations.

Keep Reading

More From Cassidy