If You Miss Once, Try, Try Again

Story Info
For love must always triumph.
6.8k words
4.64
54.8k
51
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Disclaimers:

These characters are totally and completely mine.

Love/Sex: Well yes, of course. On both accounts.

Violence: Nope.

Feedback: I love feedback! Please, please, please with cherry on top, tell me what you think.

*******

Dr. Terri Childs has been dating my brother for the past three months, the exact time I have been diligently touring the country with my band. I know it's a strange way to start a story but I think you'll understand better once I take it from the beginning and go from there. My name is Jaime Shepherd and I am a musician. I'm twenty seven years old and I have been in the music business since even before I can remember myself. This story, however, is as much about my success as it is about my brother. As I have said before, for the past three months I have been busy with a tight schedule of almost daily shows throughout the country. My band and I love nothing more than touring with our music.

here is something about creating music and presenting it to the fans for the first time that simply makes my heart stop then immediately beat faster as though I have just jumped from the highest building into an endless abyss. I'm the lead singer of the band, as well as rhythm guitarist and I happen to write most of our songs. I'm self sufficient, what can I say? Back to the story though. As I have been making my way from place to place I managed to get in a few calls to the family, checking in and making sure all was well while I was away. Can't ever stop worrying...that's what you get when you're the oldest. How surprised do you think I was when I first heard that my little brother, who is not that little actually, barely twenty five, has found himself a girlfriend...and a doctor, no less. I was thrilled for him and for my parents, who were beginning to worry about his flaky countenance and attitude toward dating and women in general. During each conversation I managed to pull a bit of information about the new girl but was constantly faced with a wall of silence. What could one do? I was happy and wanting to meet her but that was all. I had practically forgotten about the entire deal by the time I was on the flight back home for the holidays.

As I rested my head against the soft headrest of the seat, images from past shows popped into my mind, putting a large smile onto my sleepy face. The flight over and done with, I knew I had some business to take care of before being able to go home. During these long times away I missed my family but I knew it was a sacrifice I was delighted to make. It was a dream come true and I had given my all to become who I am today. As I reached my place of business, my cell phone decided to ring, making my entire backpack vibrate with impatience. I pulled the phone and checked to see who was calling. Smiling, I picked it up, "Hey mom."

"Hey baby. Where are you?"

"I'm at the office, I'll be home in about half an hour. I have some things to take care of and I have to pick up my car."

"Okay, but don't be late. You know your brother is bringing his girlfriend home for lunch."

Smiling as I handed my assistant the piece of paper she had given me to sign, I said, "Oh right, she's coming today. Don't worry, mom, I'll be there on time."

When the call ended, I hurried through a bit more paperwork with the assistance of my assistant and left the office. The parking lot in which my car had been staying for the past three months was nearby so I decided to walk the few blocks. Enjoying the fresh air and slight wind blowing softly at my face, I inhaled deeply. A few minutes later I had reached the parking lot. I turned the corner and went to the booth situated in the middle of the entrance. "Hello." I greeted the person inside the booth. The young man turned his face up to glare at the intrusion but as he noticed me, a smile suddenly graced his lips. "Miss Shepherd, welcome back."

"Thanks Tony, it's good to be back. How is my baby?"

Everybody knew how much I cherished my beautiful, sleek black Porsche Boxster. It was practically the very first thing I bought with my first pay check from the music business. Well, not exactly the very first...my entire family received a car...each to his own tastes and likes.

Tony smiled and said, "Oh, she's perfect. I even washed her up for you yesterday."

I grinned, thinking what a smart boy that Tony was...he knew I was going to give him a serious tip after his kind treatment. "Do you have the keys?"

"Well of course, ma'am." He stepped out of the booth, keys in hand and walked me to my car. I felt my heart quicken for a second before my eyes captured the shiny chrome. Just like the first time when I saw her in the store window. Call me childish, but it was still a thrill to know that I own the car of my dreams. Anyhow, back to the story. Tony handed me the keys and opened the door for me. I thanked him and climbed inside. I love the smell of leather and the car smelled like it was brand new. Well, considering I had bought it only several months ago and driven it even less, it was fairly new. I smiled at Tony in thanks and appreciation and fumbled for my wallet. Taking out a hundred dollar bill, I handed it to Tony who took it greedily and more than happily. Putting the keys in the ignition, I thrilled at the sound of the roaring motor and pulled the door close. Waving to Tony, I put the car in first gear and rolled out of the driveway smoothly. The car ran like a dream as I shifted from one gear to the other. The streets were practically empty at that hour considering the fact that it was holiday time and everyone was probably at home or someplace else with their family. I glanced at my watch briefly during a longer wait at a stop light and frowned in surprise. I was already late and I was even more surprised that my phone hadn't rung. As if my thoughts had been read, the phone started ringing and vibrating in my pocket. Holding the wheel with one hand, I answered with the other, "Yeah?"

"Where are you? We're all here already." Said my mom's angry voice.

"I'm sorry, mom. I didn't notice it was so late. I'm on my way. I'll be there in about ten minutes."

Hanging up, I concentrated on maneuvering the car down the streets toward my parents' house. Entering the enclosed driveway, I pulled the car to a stop behind my parents' car and shut off the engine. Looking in the backseat, I smiled. It was littered with beautifully wrapped presents. Not only were the holidays coming up, having come back from a long tour I was struck by an uncontrollable urge to spend; on my family, no less. Stepping out of the car, I straightened my shirt and pulled my leather jacket tighter around me. Piling the gifts in my arms, I looked in the side mirror once more to make sure everything was in place and headed for the front door. Knocking softly, the door was immediately opened and I was engulfed in a big, warm hug from my mom. The presents, luckily, survived the onslaught, allowing for a one-armed squeeze and a smile. Pulling away, I gave her a peck on the cheek and entered the house. "Hey everybody." I greeted the people waiting in the living room. My dad was standing next to the beautifully set table, smiling in welcome while my brother sat on the couch next to his girlfriend. Jack was wearing a long sleeved white shirt with blue stripes and a pair of blue, low hung jeans. He was sitting sprawled on the couch as he waved hello. "Sorry I'm late, I had some stuff to finish at the office." I placed the presents on the couch, took my jacket off and went to introduce myself to our guest since my brother seemed a little reluctant on making the introductions. As I gazed upon the girlfriend, an instant smile lit up my face. She was one of the sweetest looking girls I have ever had the pleasure of gazing at. She was blonde with big blue eyes, tiny in stature as I soon found out and pretty as heck. Rolling my surprised tongue back in my mouth, I greeted charmingly, "Hi, I'm Jaime."

She smiled as well, showing a mouth full of perfect white teeth and shook my hand warmly, "Hello. I've heard a lot about you. I'm Terri."

I flashed her one of my famous lopsided grins, "I'm sorry to say that I can't say the same about you." I noticed my brother blushing a bit from the corner of my eye. His darker complexion usually prevented my detecting a blush, but this time it was quite prominent.

"Anyhow, I've picked up some things for you guys while I was on tour..." I said, changing the subject smoothly. Handing the presents out, my heart swelled when I heard the appreciative sounds.

Since I had barely heard anything about the beautiful stranger, I had had some trouble finding a gift. But, as I've learned from the family, you can't miss when you go expensive.

With everybody overjoyed and grateful, my mom implored with a slight tinge of reprimand, "Let's eat, the food is getting cold."

I smiled shyly and went to the table to find my place. Sitting with my dad to my right, Terri to my left and my brother to my front, I was surrounded. My mom, whose place was next to my dad's, brought the food onto the table. Charming and helpful as ever, I offered to help, but was refused and admonished to sit quietly in my place. Frowning indignantly I sat back down and blushed slightly at the soft chuckle I heard from my left.

As we started eating, all embarrassment faded and we began conversing and the getting to know each other process. "I can't believe I'm actually sitting here with you and your family, I'm a big fan of your music." Said Terri shyly.

I smiled crookedly and said, "Thanks. I'm glad you enjoy my music. Next time we perform around here, I would be happy if you'd join the family."

Terri beamed, "Thank you, I would love that."

"So, you're a doctor. That's amazing, beautiful and smart." I said, oozing charm. I winced slightly as my brother kicked me in the shin underneath the table. I glared at him and turned back to the beautiful doctor at my side, who was turning a pretty pink shade right in front of my eyes.

"Thank you." Answered Terri.

"Where do you work?"

"I work at County."

"Really? That's really close by. You look too young to have been working for too long..."

"Well, I'm a resident, I haven't been there for long, but I like it."

"That's good." And before I could continue my chat with the lovely doctor, my brother decided to barge in and ask one of his unimportant, out of place questions.

"How was the tour?" Ok, so it wasn't exactly out of place but it was unimportant at that specific moment in time. It wasn't like I was doing anything to his girlfriend, I was just inquiring and getting to know the woman he's been dating, as any good older sister should do, even if she did embarrass her brother along the way. I turned my gaze to my brother and smiled, "Just fine, thanks. How has work been?" Jack studied four years of physical therapy and had already gone through a year of practice. He was now working at a clinic a few blocks from the hospital where Terri worked. I figured that was how they had met, having a common patient. My brother is a good guy with a good heart but he has a way of ruining it by opening his big mouth and spewing some really nasty things when mad or just annoyed. He was also a very diligent and dedicated worker as he had gone through much trouble in getting accepted to the clinic he was working for. Perhaps too dedicated at times.

"Work has been fine as well. When do you get back to working?"

I smiled, "I just got back. Are you so eager to see me back at work already?" My mom shot me a look that said we should cut it out before she'd kick us both, so I stopped...for the moment. Turning my attention back to the pretty little blonde, I asked, "How did you two meet?"

"A patient of mine needed physical therapy and I sent him over as it turned out, to your brother. Jack later came by to check out on him when he came to a check up and we met and started talking, and that's it."

"Wow, way to go, bro." I smiled at Jack, who kicked my shin yet again. This time I couldn't stop the small yelp from escaping, but I made sure I got him back good. My mom got up abruptly and told us to help her clear the dishes and bring the dessert onto the table. I could see Terri smothering a slow smile. I smiled as well and gladly got up to help my mom.

Lunch was soon over and I realized I still had some work to do at my own apartment and if I wanted to finish it in time for me to catch up on my sleep, I should be going. I went over to my mom and hugged her, thanking her for the wonderful meal; mom always did know how to prepare a perfect, holiday feast. I hugged my dad goodbye and then went to my brother, whom I punched lightly on the shoulder. He grunted and that was the way we said goodbye to each other. I then stopped in front of Terri and said, "It was a pleasure to meet you. Anytime you'd like to talk or hear us sing, you're more than welcome to call me." I gave her my cell phone number and left the house.

The next day came before I had a chance to get rid of my jetlag and I rose tiredly from my bed when a few rays of sunshine hit me square in the face. I crawled toward the bathroom and took care of business, grabbed a bagel from my counter, which was probably three months old and went out the door. I had a meeting with my manager and assistant about the organization of my schedule and then I was free for the rest of the day. Climbing into my car I drove over to the office, smiling in surprise at actually finding my manager there at such an abhorred hour and on time, no less. "How was your homecoming, Jaime?" He asked, sipping from the dark brew in his hand slowly and methodically.

"Just fine. Yours?"

He grunted. He reminded me a lot of my brother at that particular moment. "So, what does my schedule look like for the next month?" He started going over the schedule; things I approved he marked with a 'V', things I didn't, he made a note to speak with the respective person and notify them of the changes. My schedule done and decided, I was finally free for the rest of the day. It had been quite a while since the last time I had had a day off and I was nearly clueless as to what I should do with myself. I looked at my watch and saw it was just about time for lunch so I decided to go out on a limb. Terri's clinic was a couple of blocks from my office and I wondered if she would like to have lunch with me. I wanted to get to know her better and what better way? Now I know what you must be thinking; me, alone with a beautiful, young doctor, who also happens to be my brother's girlfriend. I have never stolen any of my brother's girlfriends and I wasn't intent on doing so now. Besides, they were all quite bad looking or had at least one character flaw. But I'm again digressing.

I got out of the building and went to take my car on the short drive over to County. I parked the car and got out, walking toward the entrance. When I entered the hospital, the strong smell of antiseptic struck me full force. I walked to the nurses' station and smiled charmingly at the nurse on call. "Hello. Can you tell me where I can find Dr. Terri Childs?"

The nurse looked at me wide-eyed and pointed down the hall. I thanked her and as I was about to turn and walk where she had pointed, I ran into someone. "I'm sorry..." As I looked at the person whom I was holding in my arms, preventing an imminent fall, I smiled in recognition, "Hi Terri."

"Hey!" She said in delight. "What are you doing here? I hope there's nothing wrong..." She quickly asked in concern.

I reassured her hurriedly and asked her if she wanted to join me for lunch since I knew she had to eat and since I was having the first day off since ever and before I could rumble on, she laid a soft, manicured hand on my arm and stopped me. "I would love to, but I have two more patients to check before I can leave, ok?"

A slow smile spread over my lips and I nodded, "Perfect."

Before too long, Terri joined me at the door and we left the hospital together. I led her to my car and she gasped in wonder, "That is one beautiful car."

I smiled with pride, just as if it were the very product of my loins (close, my wallet). I went over to her side and opened the car door for her. Waiting for her to get in, I shut the door and ran over to the driver's side. During the ride over to the restaurant we were both mostly quiet, just exchanging pleasantries and information. "Do you like Italian?" I asked.

She nodded vigorously and said, "I love Italian."

Smiling, I said, "Good. I know this great restaurant, not far from here."

A few minutes later we stopped in front of the restaurant and I handed the keys to my precious car to the valet, who was familiar to me. "Hey Danny, be careful, you hear?"

Danny smiled and nodded enthusiastically, "Of course, Miss Shepherd."

I went ahead and held open the door of the restaurant for my companion. We entered and were immediately seated in a private, far off section of the restaurant, enshrouded by plants and privacy. I pulled Terri's chair out and sat down. Old habits are hard to kill. Terri smiled and I sat in front of her. "You are so charming, I wish you could teach your brother some of these manners." She said teasingly, but I knew there was truth to her words.

We had a very pleasant conversation and an even pleasanter meal, which ended with a short argument over the bill. "I can't let you pay for me..."Said Terri, indignantly.

"Terri, please, I invited you, you're insulting me...you don't want to do that, do you?" I asked with a slight cock of the eyebrow.

Terri sighed deeply as she knew she had lost. "Alright, but next time is on me."

I smiled in relief and joy at the prospect of there being a next time. I really had a wonderful time and Terri was stimulating company. Not in that way, you perverts.

I drove her back to the hospital and dropped her off as close to the entrance as possible without actually being an ambulance. She thanked me for lunch and I again told her to feel free to call whenever she needed or wanted anything. She gave me her phone number as well and we parted ways. As I found out later, her friends at the hospital ribbed her and teased her, asking about me. They had recognized me but were too stunned to say anything in front of me.

One day rolled into another and work kept me busy pretty much most of the time, but I always found the time to talk with Terri, either on the phone, over lunch or anywhere for that matter. We grew closer as we saw each other more frequently, since every time I was at the office, I would call her up and ask her to lunch. To this day, she keeps nagging me about letting her pay for a meal. I still haven't caved.

My brother and her had been dating for four months, pushing on five and it wasn't looking particularly good. Terri would complain to me about the fact that he was never there, about the fact that they would almost never go out anymore and that it was getting harder and harder for her to feel anything for him. His work was taking up all their time and he never found the time to spend with her. She was a doctor and she always did her best to maneuver through her patients in order to be able to see him, but he would either cancel at the last minute or not show up at all. I was more than pissed at my brother for treating this wonderful woman so flippantly, especially since I was already wondering how she could have gone out with him in the first place. I tried to talk some sense into him but nothing worked.

One evening, I was at my parents' house, hanging around after a long day of recording and I was too tired to go to my own apartment and be alone. My bother, it seemed, was feeling the exact same way because when I got to the house, he was already there. It was around 9:00pm when Jack's cell phone rang. He went to pick it up and from the one-sided conversation I gathered it had to be Terri. My brother started raising his voice suddenly, sounding upset until he hung up. He came into my parents' bedroom and sat down. My mom asked him what had happened and he told us that Terri called and she was upset because one of her patients had just died. I'm not sure if she actually requested him to come over or just hinted at it, but he immediately told her he was too tried to drive over and that he'd see her tomorrow. Unable to hold my anger inside any longer, I snapped at him and asked, "What is wrong with you? Your girlfriend calls you all upset, asks you to come over and be with her and you tell her you're too tired?! She shouldn't even have asked you to come, you should have gotten into your car the minute you heard her upset voice."

12