High School Memories... and Regrets

High school, for me, conjures up bittersweet memories.

For the most part, they were happy years. Despite lacking a life plan while in high school, I was a good student. My friends and I never got in much trouble. At least, the police were never involved. A better than average athlete, I was a starter on the varsity basketball team. My parents are happily married, and home life was better for me than most of my friends.

So, what's the bitter part? Despite being generally self-confident, I was a basket case around girls. I tried dating a couple of times, but my shyness sabotaged any possibility of a relationship.

My name is Mark Murphy, 'Murph' to my pals. I am currently a 24-year-old freshman, enrolled in Engineering at the University of Calgary.

With no clear plan at graduation from high school, I took a job in the oilfields of northern Alberta.

Oil prices were high and so were the wages. In five years, I managed to save enough for my tuition and living expenses to see me through four years at the Uni.

As I left class on a Friday of a hectic week, my cel vibrated in my pocket. 'Jake the Snake' came up on my screen.

Answering I heard "Murph. Clear your sched tomorrow. I scored tickets to the Flames/Boston game at 1:00 and we'll do a pub crawl on 'The Red Mile' after."

Jake has been my best pal since junior high. I hadn't seen him for a while, so I accepted immediately.

The hockey game was great, even though our beloved Flames lost in overtime.

The first bar was disappointing, so we left after one draft lager.

As we found a table in the second pub, Jake said, "What's the woman situation these days?"

"Same ole, same ole. Just trying to stay serious about my courses."

"Bullshit! You gotta get over your hang ups."

"Easy for you to say. You always had a way with girls. Can't say I'm not envious."

"What if I set you up with Darla?"

"Darla Engels? What have you been smoking?" I replied dumbfounded.

"None other. I ran into her this week. She works near me, and we agreed to meet for lunch next week. She's available too."

Darla Engels! I had a thing for her the first moment I laid eyes on her.

She was a curvy blonde with big green eyes, and to me, she was the prettiest girl in the whole school. Oh yeah, she was also the smartest girl in the whole school. Hell, male or female, she was probably the smartest person in school, teachers included.

After the first two years in high school with no direct contact, we ended up in the same Grade 12 class. Better yet, we were assigned to each other as Chemistry Lab partners. We got along well enough. Chemistry was a strong subject for me so I didn't embarrass myself too badly. It even got to where I could talk to her somewhat comfortably in lab class.

"So, what do you say?" Jake asked. "Should I talk to her?"

"Why would you think that she would want to go out with me? She could probably have anyone she wanted."

"You always got along great with her. She said to say hi to you. Tell you what. I'll give her your number. If she calls, you will have to believe there is a chance. Don't make me look bad."

We may have stopped talking about Darla but, three bars later when we parted ways, I had not gone five minutes without thinking about her.

The next week was the same.

Jake was meeting Darla for lunch Thursday. I was careful about having unrealistic expectations, hopes even. By Sunday, I had not heard from Darla and Jake hadn't replied to numerous texts. It had been nice to think about, but it was time to let that fantasy go.

Leaving my last class on Monday, I checked my cel. I had a text message from an unknown number.

'Hi Mark its Darla Engels. Jake gave me your number and I'd love to catch up sometime. Call me'

'Great to hear from you. Love to chat. When is it good to call?'

'After six tonite not too late early flight tomorrow.'

It was like the sun came out after endless cloudy days.

I did not want to appear too eager, so I waited until almost 6:02 before I scrolled through my 'Favourites' contacts. Optimistic to have placed her there, I know. Anyway, I tapped her number to make the call.

After three rings, it went to voicemail. I hesitated and briefly considered hanging up. Oh hell!

"Hi Darla, it's Murph. I'll try again later."

Five minutes later, my cel chimed, and the display indicated 'Darla'.

"Hi Darla." I answered, not knowing what to say next.

"Sorry I missed your call. Work stuff. It's great to make contact after all this time."

"Yeah, for me too. How have you been?"

"Well things are crazy at work right now. In fact, I have to go into the office right now to put out a fire before I leave for Vancouver first thing tomorrow. Can we get together after I get back?"

"OK..... sure." I replied.

"I get back Friday evening, but I will be too wasted to be pleasant company. I am available any time this long weekend. How does Saturday work for dinner? My treat, as a way of apologizing for the mix up. Do you have a favourite restaurant?"

"Yes, is Italian okay?"

"My absolute favourite as well. Text me the details and I'll see you Saturday. Sorry, gotta run now."

"OK. Bye."

I sat stunned, trying to make sense of what had just transpired. Feeling a mixture of surprise and hope, I tried Jake again. This time he answered.

"Did Darla call?" he opened without a 'hello'.

"Yeah. I think it went pretty well. We are having dinner this weekend, but I'm pretty nervous."

After I gave him my take on the interaction with her, he spoke. "You should chill man. She made contact with you first. It sounds like she wants to see you. I can tell you that she is in a stressful work situation right now. Don't let her get away this time."

Jake had eased my concerns, and I decided to give her a chance to do the same.

Tuesday evening, I texted the name and location of a restaurant, suggesting meeting at 7:00PM.

Wednesday, she replied, 'Luv that place I'll meet you there'

At 6:50 on Saturday, I sat at a reserved table at Gran Caffe Rossi.

Almost seven years since I last saw Darla Engels, she walked in. Her confident poise was still apparent, but physically there were noticeable differences.

In school, she had always kept her blond hair short. Now it was shoulder length, and it swirled provocatively as she moved. Her attire had been plain and conservative, now it caught the eye of every male patron. Many women as well. Back then she tended towards a slight pudginess, now she was fit and trimmer, while still maintaining the curves that aroused me then.

She scanned the room and I raised my hand as she looked in my direction. She smiled broadly and moved toward me.

Standing, I struggled to find the appropriate way to greet her. Darla solved that problem for me by closing in and embracing me with a warm hug.

The opening round of small talk commenced, casual for her but awkward on my part. We ordered meals and a bottle of wine. With a glass of Chianti in hand, she clinked my glass, "It's good to see you again after all this time."

The conversation continued as we waited for our meals and by the time our table was cleared, we had done a pretty thorough recap of the years since we left high school.

Later, enjoying coffees and Sambuca, she went quiet for a moment and hit me with a broadside, "Why did you never ask me out in high school?"

After a momentary freeze up, I replied. "Aside from the time we spent as lab partners, I didn't think you knew I existed."

"I knew who you were. I watched you play basketball. I watched you with your friends and I knew that you looked at me all through Grade 12, when you thought I wasn't looking. I took that to mean that you liked me."

"You are right about me looking at you in Grade 12, the truth is it started in Grade 10, the first moment I ever saw you in fact."

"Wow! Should I have been worried about stalking?" she laughed.

"Dangerously close, I admit. No other girl in school interested me."

"So again, I ask, why didn't you ask me out?"

"I would never have thought I had a chance with you."

"Did you know I never dated in school? Aside from a couple of real creepy guys, nobody even asked me out. I knew my reputation, 'Brainiac' right? Every guy was too intimidated to talk to the 'smart girl'. I wasn't about to 'dumb down' to get a date. I thought you might be different from the rest."

"I admit to being intimidated, but I thought your intelligence was one of your most attractive qualities."

"So where do we go from here then?" Darla asked.

"If you are suggesting that I have an opportunity to make up for my mistakes in school, I am going say that I would like a second chance."

"Maybe you are as smart as I always thought you were." Darla said as she gave me a soft punch to my bicep. "I live a couple of blocks from here. Walk me home."

She hooked her arm through mine as we walked, and far too soon, she stopped in front of a brownstone unit near the river, "This is me." Without warning, she leaned in and kissed me. It was only a brief peck and a light embrace. Releasing me she moved toward the door saying, "I am in town for the next two weeks. Will you call me?"

"Is tomorrow too soon?"

"No." And she was gone.

I barely slept that night. At 11:00 the next morning, I texted 'Wanna do something today?'

'Sure. Do you like the Zoo?'

'Haven't been there since I was a kid. What time should I pick you up?

'Noon works for me.'

'Done. See you then.'

She greeted me at her door with a light embrace.

The rest of the afternoon was spent strolling through the numerous animal exhibits. We conversed casually, more comfortably that I would have imagined me being capable of. At various times she again looped her arm through mine, occasionally holding my hand. She smiled a lot and laughed easily.

In the African Pavilion, we sat beside the hippo pool. As they frolicked in front of us, they created a giant wave that overflowed the edge of the pool, dousing us with a mini tsunami. Jumping on my lap, she laughed boisterously and hugged me before kissing me softly. "Take me home, I need to dry off and change."

Back at her place, she unlocked her door and invited me in.

Lighting the gas fireplace, she said, "I have nothing to offer you for food, but there is a Thai restaurant at the corner where we can get take-out if that interests you."

"Sounds great. This one's on me."

She retrieved a menu from her desk and handed it to me. "I need a shower. You order and I'll get presentable. Make yourself comfortable."

After dinner, she sat close to me in front of the fire and spoke. "Have you noticed that I have made every move so far? Is that the way this relationship is going to be?"

Stunned by both her bluntness and the thought that a relationship was even a possibility, I steeled myself and spoke. "Well, I have been wondering what it would be like to kiss you. I am reluctant to admit to you that all my life experience with women is with you."

"All right then," she started. "Why don't you just let go. I don't think that I've given you any signals that I don't want to be with you. Also, it is very sweet that you are so infatuated with me. I recently ended a bad relationship, but I am open to a new one."

Suddenly I didn't feel like talking anymore. I put my arm around Darla and drew her to me tightly as I started a long slow tight-lipped kiss. When it ended, I said, "I can do better," and reengaged. This time I softened my lips and relaxed the Boa Constrictor embrace. Darla seemed to melt into me as I felt the tip of her tongue pushing gently through my lips.

When it ended, she said, "Much better, indeed."

"I hate for this night to end." I said.

After turning off the fireplace, Darla extended her hand to me. "Come with me."

My heart raced as she led me to her bedroom. If I had a pulse monitor, it would surely be registering in the danger zone. We stood beside her bed and undressed each other. My body was jelly. Nothing seemed to be working as I got my first look at a living naked woman. Well my cock seemed to be in fine form as it throbbed painfully, suddenly too big for my confining jockey underwear.

In my life, I had imagined her naked a few thousand times. Darla stood before me more beautiful than any fantasy I had of this moment.

As we touched and kissed each other all over, she seemed to sense my apprehension. "Let's have some fun." She purred as we fell into bed. Time seemed to have no meaning as I caressed her magnificent breasts.

"I have other parts that like to be touched as well." She moaned as she moved my hand down her body.

When I touched her neatly trimmed blond pubic hair, she opened her legs, allowing complete access to the most desirable and mysterious part of a woman's body.

It took all my will power, not to ravish her hungrily. As I touched a woman's pussy for the first time, I made a special effort to pay close attention to Darla's reactions and sounds. I was in awe of how soft she felt, as well as the wetness. The scent of her juices aroused me even more. I searched for her clitoris with the tip of my finger, knowing I had found it when she jerked suddenly. "Gently." She whispered. "And slow."

When I found a rhythm she seemed to like, Darla began to writhe and moan more loudly. Despite my total lack of experience, I sensed she was approaching her climax. "Faster now. Yes.. yes... yeeess!" she almost screamed as her thighs slammed closed, trapping my hand in an excruciating vice grip. Not knowing what to do at this point, I tried to keep my fingers moving. "No more. Too sensitive."

After her heartrate and breathing slowed, she smiled and kissed me passionately. "That was amazing! Let me make love to you now."

Straddling me, she slowly lowered herself until she brushed against the tip of my penis with swollen wet pussy lips. She seemed to be intent on teasing me. I wanted none of it and pushed upward seeking entry And then I was fully inside her. Nothing had ever felt so good in my life.

I would be surprised if I lasted a minute before I erupted, filling her with the biggest load I had ever ejaculated.

"Sorry...." I started to say, when she muted me with a kiss. As our lips disengaged, she moved hers close to my ear. "No apologies.... ever. We have the rest of the night and all day tomorrow."

We spent most of the next two days in bed, making love in positions I had not even fantasized about.

All too soon the weekend was over. Saying goodbye at her door, I said. "That was amazing."

Darla gave me one last lingering kiss on her front steps and then pushed me toward my car. In a lusty voice she said "It's only going to get better, I promise."