The Last Time I Saw Doug

Though they call it a May-December, my relationship with Doug spanned the months of January to April—exactly one semester of my third year of art school. He entered the picture during the last week of school before winter break, which coincided with my 20th birthday.

It was an unusually busy morning at Crema, my favourite café and study spot. There weren't very many seats there, so I would typically try to get to Crema early to claim a table. I was parked at my usual window seat with my nose deep in a book when Doug approached me and asked me two things: "What are you reading?" and "Can I share this table with you?"

At first, I reluctantly obliged to sharing my table. I was in no mood to entertain small talk with a random old man, but the hospitable Maritimer in me just couldn't say no. Being from Halifax, it was not in my nature to shy away from showing kindness to strangers.

Doug offered me the piece of complimentary chocolate that was served with his latte. I opened the foil-wrapped square, popped the chocolate in my mouth, and answered his question. "I'm reading a design textbook," I replied.

My best guess was that Doug was in his late 60s. He was thickset, solid, and no taller than 5'10. He wore a black beret that covered his short gray hair, and a pair of thick-framed glasses were perched on the bridge of his nose. His salt-and-pepper beard was the perfect match for his houndstooth scarf. He was dressed in an unfastened navy wool toggle coat, which revealed a black sweater and a pair of red trousers underneath. I would be lying if I said I wasn't admiring his look.

"Design, huh? What do you design?" he asked.

"I'm a graphic designer," I replied, "or, I guess, I'm becoming one. I'm in art school. They make you learn different mediums before choosing your major, and I picked graphic design, so I guess I'm stuck with it."

"Trust me, it might feel like you've made a consequential decision, but you really don't have to choose now," he replied knowingly, looking at me with earnest and reassuring eyes. He looked like a wise owl peering at me through his coke bottle glasses.

"What do you mean?" I asked. I knew he wasn't talking about degrees or school.

"Well, I must have changed careers three or four times now," he said, speaking with his hands, "I started by taking over the family business after high school, and then I got into selling clothing, eventually designing it. It wasn't until the late 80s or so that I became a photographer, which I've been doing ever since. I've photographed a number of celebrities and people, from bands, to writers, to filmmakers."

Doug's compact retelling of his life story all sounded like a tall tale, so unimaginable and far removed from my reality. I just listened and nodded, trying to decide whether or not I should believe what he was saying.

"I've lived in London, Paris, and New York," he added, "but the point of telling you all this is that it took me almost 50 years to figure things out, and I still don't know what I want to be when I grow up, so you'll be fine. If you're as focused as you looked just moments before I came and distracted you, I'm sure you'll go far."

"Well, that's nice of you to say," I said, smiling at him shyly. "It feels like I'm anything but focused these days. You're not a distraction, though. I'm always up for an interesting chat. I'm Jess, by the way."

We talked for just a little bit longer that day, but we quickly managed to bond over our shared interest in jazz piano and a mutual love for the osteria around the corner.

As he packed up to leave, Doug waved his business card at me and urged me to email him. He even offered to take my portrait sometime. I grabbed the taxi-yellow rectangle from his hand and gazed down to read it. In bold black type, the card read "Doug Baker," above the title "Toronto Portrait Photographer" and a link to his website. The other side of the card displayed his phone number in jumbo text. I filed it between the pages of my book.

When I got home that afternoon, I felt compelled to open up my laptop and type Doug's URL into my browser straight away. The website must have been made (and last updated) in the year 2000. The simplistic look of the webpage did absolutely no justice to the beauty of his work. Though he was no Annie Leibovitz, he had taken the portrait of some fairly notable, high profile people.

I'm not sure what possessed me that day, but I ended up tracking down Doug's email address on the website to write him a quick note:

Hi Doug,

It's Jess (we shared a table at Crema). It was nice meeting you today. Thanks for the chat.

Just leaving you a quick note to say I loved looking through your photography. Amazing work.

Don't be a stranger!

Jess

Over the winter break, I was delighted to receive an email from Doug with the subject line "Happy New Year." He had written me a cordial message wishing me a happy holiday season. There was mention of eating too much food with loved ones, dreading the Toronto winter freeze, and looking forward to our next chat at Crema, where he was somewhat of a regular. He signed off with, "Yours truly, Doug."

Touched by our email exchange, I found myself back at Crema after the holidays with hopes of running into Doug. One Wednesday morning, he finally appeared, beret and all.

"Jess! I was hoping to find you here," he exclaimed.

"Hi Doug. Nice to see you again. Would you like to sit with me?" I asked.

"Of course, Jess," he replied, "I'm so lucky to be in the company of such a lovely young lady."

"Oh, please," I said, though his comment tickled me.

We reconnected a little, but we mostly sat in silence, reading. Somehow the quiet between us signalled an unspoken understanding that we appreciated each other's company.

From then on, Wednesday morning became our thing. Doug would walk in at 11am, give me a nod, and take off his coat, leaving it on the chair across from me as if to claim his seat. He'd order his drink and bounce around the other tables to greet all the regulars—his coffee shop friends—before eventually settling down to sit with me at our table by the window.

Like clockwork, Doug handed me the small piece of chocolate that came with his drink, a sweet offering for saving him a seat. He grabbed my attention by sitting in front of me with his chin resting on his fist, looking me in the eye, and raising his eyebrows as if to ask "how are you?" without speaking.

As the weeks went by, Doug imparted wonderful wisdom on me. He was worldly and well-travelled, knowledgeable, told great stories, and made plenty of room for me to vent about my undergraduate-level problems. I loved hearing about his jet setting days and his family's stories in particular.

By April, we had spent a string of wintry Wednesday mornings together and Doug had become a true-blue friend. I knew our friendship was in full swing because we had developed inside jokes, nicknames for the other regulars at the café, and a fun habit of indulging in a cheap slice of pizza together. I probably learned more about art from him than I did that entire semester at art school.

With the school year coming to a close, Doug asked if he could take me out for dinner as a bit of a send-off before I went home to Halifax for the summer. I suggested we pay a visit to the neighborhood osteria that bonded us. We made a reservation to dine there on my last Friday night in the city.

We planned to meet at 6pm outside the restaurant. I was running late and began rushing towards him once I turned the corner and saw him waiting for me. From afar he was almost unrecognizable, looking more gentlemanly than I'd ever seen him before. He'd traded his beret for a cap, his usual pilled jacket for a spiffy overcoat. He'd even groomed his beard.

"Doug! Who knew you cleaned up so well?" I teased.

Doug looked me up and down and said "I could say the same for you. I adore your look today Jess."

I was wearing a belted beige trench coat over a little black dress; a skin tight, long-sleeved number with a turtleneck that clung to my body all the way down to my knees. Though it covered most of my skin, the fabric was thin, and I'd neglected to wear a bra, letting my perky, B cup breasts with pierced nipples poke through the fabric of the dress. I was wearing a pair of short velvet pumps that lifted me to 5'3, some gold hoop earrings, and red lipstick to finalize the ensemble. I let my wavy, ashy black hair stream down my shoulders, and combed my bangs into place along my forehead.

I had grown accustomed to Doug using my arm as a crutch, especially while walking the icy Toronto sidewalks together. Though the city had already thawed, I still offered him my elbow to walk the short path into the restaurant.

I hadn't given much thought to what a wild combination Doug and I must have been to the other patrons at the restaurant: a young woman linking arms with a much older gentleman, stepping into a candlelit restaurant full of couples on date night. I dared not look around to confirm whether heads were turned our way.

Once we were seated, Doug's first order of business was to order a bottle of wine. It didn't take long for him to land on a Barolo to go with our meal. When our waiter came by with the bottle and two glasses, I enjoyed the spectacle that was Doug doing the dance of wine tasting.

Doug's face changed unpredictably, his eyebrows shifting as he inspected the bottle, and our server offered him the first pour. He took the glass in his hand and sniffed it subtly, all while carefully eyeing the wine inside. He tilted it towards him, only to take a sensual, lingering sip. I waited anxiously for him to give his nod of approval.

Knowing how particular he was, I let Doug order all our food while I picked at the fennel-marinated olives in front of me.

Suddenly our setting felt so formal, so adult. We were in an intimate restaurant, enjoying a bottle of wine together. I was at a loss for words. Thankfully, Doug always had something to say.

"Well, it's nice to be here together, Jess," Doug said. "Thanks for going out with this old guy."

Doug's brand of self-deprecating humour never failed to make me chuckle. I giggled and replied, echoing his sentiment, "Well, thank you for inviting me to dinner. You've really become one of my closest friends. I see more of you than some of my friends from school."

"Jess, that makes me so happy," he replied, "I'm lucky to call you my friend. You have this way about you, such a good head on your shoulders. How do you like the wine?"

"It's lovely, Doug," I said, swirling my glass to mirror his mannerisms, "I think I've become a red wine gal."

"Excellent" he said, "I hope you like everything I ordered for us."

"I eat just about anything Doug, so I'm sure I will," I said, "and I've yet to have a bad meal here."

I gazed down sheepishly, feeling self-conscious about the way I was holding the stem of my wine glass, searching for something to say next.

"Doug, I have a question. Why did you first approach me at Crema back in December?" I asked.

"That's a good question, Jess," he replied with a furrowed brow. "First of all, you know how small it is in there. You can't get a table unless you're really lucky. You were sitting alone, and I was so intrigued by the look of focus on your face when you were reading. I knew I wanted to know more about you and thought I'd strike up a conversation. I just had a feeling about you."

I felt heat growing behind my cheeks as I received Doug's words.

"Thank you, Doug," I said, "I think you're great too. I look up to you a lot. I really like the way you tell stories. Since we're at an Italian restaurant, can you tell me the funicular story again?"

As pasta, bread, salad, and porchetta began appearing at our table, Doug told the funicular story, one of his that I loved and had heard twice. He always started the story by asking, "You know what a funicular is? They're steam powered locomotives."

In the late 70s, Doug found himself in Bergamo, Italy with his girlfriend, Julia. They were exploring for the weekend, and found themselves utterly entranced by the town's funicular. As it ascended, they basked in the breathtaking golden glow of the buildings set against a blue sky and lush greenery.

Doug always took a deep breath and closed his eyes when remarking about how "The Bergamo air was crisp and crystal clear" in an enthusiastic cadence.

"Julia was a great gal," he always said, marking the end of the tale. I felt him pining for Italy, and for Julia, whenever he told me about it.

"Have you had any significant lovers, Jess?" He shot me a sharp look.

Though I considered Doug to be a good friend, we'd never gotten this personal. Throughout the time we spent getting to know each other, I had mentioned in passing that I was single and bisexual. He'd been there to hear a couple reviews of (mostly bad) recent dates I'd been on.

"Yes, Doug, I've had two significant girlfriends," I said, between bites of porchetta, "Jordan, Olivia, and one boyfriend, David. After getting my heart broken last year, I've resigned to being alone."

"Stop with that nonsense, Jess. I don't know how anyone with eyes could not want you. You are so effortlessly beautiful. I still really want to take your portrait to capture it."

"Thank you, Doug," I said, tossing my hair behind my shoulders. The warm glow of a little red wine, combined with Doug's endless stream of compliments, was working wonders on my confidence. I sat a little bit taller in my chair, chest out, shoulders back, nipples hard. I'm certain he saw them pointing his direction.

"That's nice of you to say, but I am genuinely content with being single. I just miss touch sometimes, you know? Like cuddles, and being held."

"You and me both, Jess," Doug said, "I'm almost 70, but I still crave a woman's touch."

Sex talk was typically a welcome topic of conversation between my girlfriends and I, but not one I imagined I would find myself landing on with Doug. My brain needed a moment to process his comment.

"I guess you're right. We both need a woman's touch," I replied, giggling nervously.

"Do you still, you know, do it? When was the last time you did?" I asked. I felt my gut drop from the embarrassment of asking such a question. This side of Doug was too titillating.

Doug laughed for a moment, looked me straight in the eye and said, "Yes, Jess, I still have lovers. I've never brought it up with you before, as I wasn't sure how you'd respond, but, since you're asking, I was just with a lover last weekend."

My eyes popped wide open hearing Doug tell me about having a lover as recently as last week. Meanwhile, I couldn't even remember the last time I went all the way with someone. I looked Doug up and down, trying to picture what his lovers saw in him. Perhaps it was the inquisitive look behind those round glasses, or the way he livened up when he spoke. Maybe he was very good with his dick. I was full of questions.

"So like, it all still works down there, Doug? Even though you're almost 70? How many lovers have you had?"

Doug shot me a smug smile.

"Jess, I've had more lovers in the last two decades than I ever did before the age of 50," he said. "I love to please women."

Doug went on to tell me about his recent lovers and hookups. He even used the word "hookup," a term I thought only people my age used to describe their sexual encounters. He had lined up dozens of lovers over the years, and he'd been quite active on online dating sites—often skipping the dating, and going straight to the bedroom.

"Essentially, I've been more sexually-driven in the last 10 years than I was in the first 60 years of my life, Jess," he said.

"Oh, wow. I feel like I just asked you a million questions, Doug. Thanks for letting me pry a little," I said.

I was left still wondering what Doug liked to do in bed, all while grappling with the novel idea that I was now feeling a sexual attraction to him. I couldn't look at his mouth without imagining his lips puckering to kiss my pussy; I looked at his hefty body and thought about being smothered underneath it; I imagined his big, animated hands cupping my small, pointy breasts.

"Don't apologize, Jess," Doug said, "I'm happy to share, and I will answer any questions you have for me. I do have a question for you, though."

"What's that?" I asked, bracing myself to share intimate details.

"You mentioned craving a woman's touch, but that you have also had a boyfriend," he said, with a twinkle in his eye, "so, if you don't mind me asking, do you prefer women, or men?"

I took a big sip of wine, gulping as I formulated an answer to his probing question.

"Well," I replied, "I'm reluctant to give you a definitive answer, but I've always known I liked women, and prefer them over men." Doug cocked an eyebrow. I hoped to be having an effect on him.

"When I was younger," I continued, "I thought something was wrong with me for not liking boys all that much. When the girls at school would gush over boys in our class, I always felt left out, and thought maybe I was a late bloomer or something. I just didn't care for boys. But when I eventually realized that I felt this way because I was into women, everything suddenly made so much sense. It was like putting glasses on for the first time. You don't realize how much you're missing out on when everything's blurry."

I swirled my wine a little more, adding "Plus, lesbian sex is the best. That I can say with certainty."

I filled our glasses and let Doug digest my pointed comment. He shifted in his seat to lean in towards me, looked around to see if anyone was within earshot, and said, "Jess, this is why I find you so intriguing. At just 20 years old, you seem to know already what you like. When did you discover that you liked women?" Doug asked.

Normally I'd shut down questions like this one for fear of giving too much away, but a flick had been switched in my mind. I was getting horny talking about my sex life with Doug. I wondered if he was as turned on as I was.

"I was in high school, Doug. I guess I realized I had a thing for my friend Alex. She was bi. Well, we both are," I replied, trying to gauge Doug's reaction.

"Can I ask if you did anything with her?" Doug said, without a pause. My pussy twitched.

"I won't share too many details, but we used to have these sleepovers where we shared a bed, and our parents were never suspicious about what we were up to. They just thought we were good friends. Gal pals."

My voice trailed off as I told Doug about those early times with Alex. He had a serene smile on his face, but his eyes were twinkling a little bit, as if he was hoping I'd elaborate.

"I haven't been with a woman for over a year, though," I continued, "the last girl I was with dumped me and immediately started dating some guy."

I felt myself yearning for the soft body of a woman, while feeling the dull ache of rejection in the pit of my stomach. Doug nodded along as I spoke, his silence my cue to continue.

"Since then, I've been dating and sleeping with guys, but I think I'm ready to see women again, you know, the woman's touch thing."

"Women can be heartbreakers," Doug said, "but speaking from experience, guys your age know little about a woman's pleasure. I can see why you're ready to move on. If I knew then what I know now," he said.

I was chewing on a slice of bread and nodding along when Doug asked, "Have you ever been with an older man, Jess?"

There it was. Sometimes talking about sex gives people the impression that you're interested in having sex with them. I'd become aroused by our conversation, and I could tell this was Doug's indirect way of suggesting we fuck—a thought I started to toy with, but had only just permitted myself to explore.