#Yes I did misspell shepherd what's your point

[bewaretheundead91]

A very Eventful Christmas Part 2: Wine and Tiramisu  

Summary: You are on your way back to Washington D.C. to spend time with your family for Christmas. On your way you run into a man from your past.

Duncan Shepherd X Reader (Y/N)

A/N: Christmas is around the corner? I’m sorry, due to my job I tend to hear Christmas music earlier than most. So I’ve been inspired to start a Christmas series. Subject to be edited and changed.

Warnings: (none)  a slow burn, inspired by cheesy Christmas rom com tropes...a lot of rom com tropes/clichés here...and plot.

Part 1

“Chicago to D.C. is ready for boarding,” A woman calls from over an intercom. “All heading to D.C. from Chicago may board the train now. The train will be departing in 30 minutes.”

After taking a glance up at the wide eye and smiling train attendant, you drop your eyes back down to the phone in hand, still angrily texting Erica, your cousin, about the free coffee you had taken from Duncan Shepherd. If only you were the girl you were 5 years ago, that made men cry when you had the chance. The girl that was brave and said what was on her mind. Fast forward to the present and your raging fire has transitioned into a timid candle flame. Chicago was too cold most days for a social life.

And he remembered my coffee order, you type out, misspelling the word remember a few times, out of typing too fast, my damn coffee order and he thought he could just talk to me. I was trying to hide from the guy and it was obvious. The audacity of it all, Erica responds ending with a eye rolling emoji, Did he say where he was traveling to? You look around your surroundings, there is no gray coat wearing man with soft wavy locks and a scruffy beard. You sigh. He didn’t say anything and of course I was not going to ask you text then shove your phone into the pocket of your coat. You stand up and walk to your train car. Your fingers grasp the ticket and you pull it out so that attendant can scan it.

“Good evening,” The smiley attendant greets. Her makeup is on point and her hair is perfect. “You’re seat is actually not too far from here, just a few rows down and on your left.”

“Thank you.” You reply stepping onto the train and instantly hit the heat on blast from inside of the cart.

You look down at your carry on bag to make sure it was still zipped and continue deeper into the train cart. Quickly you find your seat near a large window with a collapsable trey large enough to fit your computer. The seat looks comfortable enough for the multiple hour travel, being cushioned. You secretly hope that no one has the seat beside you. You sit down and make yourself comfortable. There was an urge to turn your phone off during the ride, but you couldn’t commit to that or the potential pile up of voice mails and missed calls from your editor or family.

“Estimated arrival time to Washington D.C. is…” You block out the rest of the dialogue and glance around the exterior of the train. People were still running to board the train, family and a cute couple walking hand and hand closely. You roll your eyes at the romantic scene before you. Young love around the holidays, good for you guys, I’m sure something will mess it all up, you thought to yourself and cross your arms over your chest, wow that was vile thought. I take it back, all of it.

Your mind wanders to what going back home would be like, your younger sister planning a wedding to be married to a young entrepreneur for a the latest electronic selling out off the shelves. Your mother being delighted to see the couple together and then nagging about how you have been single for years now since you left the D.C. area. That dreaded city, she would say you think to yourself, full of dreadful people, just like your late grandfather. Dreadful people you should even think about dating let along marrying. Washington D.C. has many eligible men for marriage.

The train had been making its way for a few hours and you start falling asleep with the ambiance of the train car along with the subtle hum of the train. Your face falls flat against the window and mashes against the glass, you were tired and finally you have a space to sleep. Your mind drifts off to the couple you earlier, than to  a series of different romantic Christmas comedy movies where young people fall in love and then to the cheesy cookie cutter, over formulaic movies you also equally love that would marathoned on cable. The movies where most of the main characters fall in love by Christmas.

The thoughts transition and you find yourself sitting on a couch sipping hot cocoa wearing a matching flannel pajama set. A series of knocks come at the door near you along with soft singing voices. You get up and answer the door to a group of Christmas carolers singling the chorus of All I Want For Christmas is You. Feeling a cool breeze, you wrap arms around your body and listen to the carolers with am excited smile. The group of singers, break apart a low voice starts to sing along with them. Your eyes meet the bright blue eyes of Duncan Shepherd who was wearing a red sweater with a large fuzzy Christmas tree on it and a big red Santa hat. He looks up at you lovingly holding a poster with large letters that wrote out “To me you are beautiful”…he flips the poster to reveal another one, “Than all the diamonds I could buy, than anything I could ever buy”…he places the poster behind another,“You are priceless, and I love you”. The heart in your chest begins to pound and you feel your face blush.

“Excuse me, Miss,” You hear a voice over the the carolers and Duncan. The carolers do not stop. You look up at the ceiling of the room you were in and frown in confusion. “Miss, I’m sorry to bother you.”

A hand touches your shoulder and you jump in your seat, colliding with the collapsable table. Before you can prevent yourself, you fall back and hit the window, face first clumsily. Finally your eyes open to see a train attendant holding a trey with a glass of red wine.

“I’m sorry for scaring you,” She beams. It was the attendant from earlier. “Are you okay? Did you hit your head hard?”

“I’m fine, but I didn’t order that,” You say sitting up in the seat. You rake your fingers through your hair smoothing the strands out and pat your cheek that made contact with the window. You look over to the glass and see a faint makeup print. “I’m sorry you have the wrong person.”

“The gentlemen in the gray coat sent it over,” She says with a smile. “He thought you might enjoy a nice red blend while you look out the window. He’s so charming.”

“Excuse me what?” You ask tilting your head in confusion.

“The gentlemen a few rows down.” She points out down the isle.

You sit up a bit more and straighten your back to gain height. You look down the isle to see Duncan Shepherd speaking to another train attendant who was handing him a glass full of a brown liquid. A frown scrunches across your face and you slowly slump back down in your seat, fixing your coat.

“Whiskey,” You snarl, looking up at the ceiling. “I can’t take this.”

“You would prefer whiskey?” The attendant asks.

“No,” You say wide eye tilting your head even more. “Just please take this back, I’m sorry for the inconvenience, but I don’t take drinks from strange men…I mean strangers.”

“But he made it clear that you two knew each other.” She nods.

“Miss,” You look at the name tag on her blue blazer. “Ms. Jessica, he might think he knows me, but I don’t know him. So please just take this back or give it to him. Or how about have a glass of wine on him.”

“Oh,” She nods. “I see.”

“No,” You shake your head. “Whatever you are thinking…he’s an acquaintance and I’m not really in the mood.”

The attendant walks away with the glass of wine and you peek behind the seat in front of you to witness his reaction. The attendant, Jessica, approaches Duncan and shows him the trey with the glass of wine. Duncan was resting his head on his hand casually staring down at his glass of whiskey.

“Mr. Shepherd,” Jessica’s voice changes, it goes lower in pitch, like she is attempting to be seductive. You scrunch your nose. “She does not want the drink, sir.”

“Oh really?” He posture changes and he turns his head to the side glancing at the seat beside him. His wavy hair bounces and you mash your lips together tightly. “Y/N refusing a red blend?”

“Yes, sir,” Jessica responds with a disappointed look.

Duncan shifts his body so he can turn towards your direction. He quickly turns his head and makes eye contact with you. You duck down behind the seat in front you of you embarrassed, feeling your cheeks burning.

Please don’t come over here, you think to yourself, please do not for the love of God come over here.

“Do you have any desserts?” You over hear him ask Jessica. “If I’m going to drink this wine I need something sweet to eat with it.”

“Would you like a menu?” She asks.

“Is tiramisu available?” He asks.

“I believe it is, sir.”

You pull out your phone and send Erica another text, he just tried to send me a drink on the train. He’s on the train with me.

Jessica shortly walks back down toward your direction, this time she has a trey with the glass of wine and piece of tiramisu. Jessica pulls out your trey and places the drink and dessert in front of you.

“Mr. Shepherd was adamant that you enjoy these treats on behalf of himself,” Jessica says then glares at you. “Just take the damn drink and dessert so I can go back to what I’m supposed to be doing, please. I’ve got three cars on this train that I need to check up on.”

“Just leave it then.” You say with a sympathetic look.

“Thank you, Ma’am,” Jessica says. “Try to enjoy them. They are expensive.”

“Of course they are.”

Before you sat a glass of wine from Duncan, another one of your favorites, and a big chunk of tiramisu, also another one of your favorites. The idea of Duncan Shepherd remembering those tiny details about you makes you annoyed. You groan to yourself and an idea pops into your head. To deliver the items back to Duncan yourself and walk away.

You unzip your carry on bag and pull out a compact to check your appearance. Other than your eyes looking tired and your mascara minimal smeared beneath your eyes, you look good for a long train ride. Your hair to your atonement was only mildly messy and starting to look gross. You close the compact and pull out you minty lip balm and coat your lips generously, then grab the drink and plate. Boldly you walk down the isle and approach Duncan’s seat. His head perks up, his piercing eyes meet yours, and a warm smile appears across his full lips. Heat rises up from your chest and to you cheeks.

“Please stop all of this,” You shout, practically throwing the wine and dessert onto his collapsible table. “I know that you think spending money is a personality trait, but it isn’t. If it is, it’s not a great one.”

“Y/N,” He says looking hurt and rubs the tips of his fingers across his lips. You quickly make your way down the isle towards you seat. You hear the squeaking of a chair and boots meet the floor of the train car behind you. A firm hand grabs your bicep. “Is it so wrong that I want to treat an old friend to something sweet?”

“Please, don’t touch me.” You say trying not to gain any attention. Duncan takes a step closer and towers over you. His eyes looking just as tired as yours, sheepish, and looking a bit more scruffier than usual once you get a better look at him. But you admit to yourself that he is still the attractive man that has made many women and men swoon.

“I just thought two of your favorite things could make the trip a bit more comfortable. I did not mean to offend.” His voice was soft, something different from earlier. You look down at his large hand still laced around your arm. He drops it. “Sorry.”

“I’m not offended,” You say taking deep breath. “I’m confused and annoyed. I didn’t expect you to be on this train, but out of course you expected me to be here.”

“I only assumed you were going back to D.C. because of the holidays, where did you assume I’d be off traveling to? Of course I’d want to spend the holidays back at home with my mother.”

“I just didn’t expect you to truly be on a train.” You say licking your lips. You watch as his eye stare down at your mouth.

“We are on a long train ride with nothing to do, perhaps we could talk.” He suggests.

“I was honestly hoping to sleep and relax before having to see my family.” You close your eyes and shake your head. “And I can’t be seen with you. Actually you can’t be seen with me. I don’t want to be affiliated with you.”

“I understand, but tell me,” He begins. “Who’s going to notice? Especially on this train.”

“That’s why I love Chicago, no one really knows me and I want to keep it like that. That is one reason I decided to take a train as well.”

“Is that true?” He laughs. “Do you really not enjoy being the center of attention?”

“Typical Shepherd.” You roll your eyes.

“But also who didn’t enjoy watching you,” He smirks. “You knew what you were doing.”

“You were watching a lot of people.” You say.

“Maybe I was,” He says raising his brows. “But there was one I had a focus on.”

At that moment the train starts to buckle on the tracks, making the individual cars move bumpily around the tracks. Suddenly you lose balance and fall forward colliding with the tall man before you and arms wrap around your body in attempt to soften the impact. Your hands meet the rough fabric of his coat, touching his chest, and you land directly on top of him. A grunt escapes his mouth and you feel his hot breath on your lips. You open your eyes to see your lips mere inches from each other and forehead mere centimeters. His eyes bolt open wide and his lips slightly part. There was whiskey on his breath. His hands slide up your back and you shiver.

“Sorry,” You say attempting to get up, but you fall between his legs in the process and chest meets his harshly. “I’m really sorry, this train, the tracks…”

“Can be bumpy, traveling across the country. It’s okay, are you okay?” He asks sounding genuinely concerned. He sits up onto his backside and runs his finger through his now wild hair. “You didn’t hit your arms or twist an ankle did you?”

“I’m fine,” You say finally getting to your feet. The heat flares in your cheeks again. “I’m the one that fell on you and your arms secured me in place.”

“You’re right,” He laughs. The train car shifts again and you fall forward against Duncan’s chest again. He wraps his arms around you holding you in place. You gaze up at him and shake your head. Honestly the view was not bad from there. Stop it, you internally scold at yourself. “Maybe you should sit down.”

“I was on my way to my seat already.” You say pushing him away. He laughs. You adjust you coat.

You walk back to you seat and sit down. To your surprise Duncan did not follow you. He was certainly a charmer for the kind of man that he was.

#duncan shepherd #duncan sheperd x reader