Kiss and Tell: “The first time I had sex was on a cruise ship—and my date’s grandma walked in on us”

Welcome to Kiss and Tell, a series about the steamy, surprising and frequently absurd world of Toronto dating. Send your most memorable stories from the pursuit of love and lust in the city to submissions@torontolife.com.

—As told to Juliann Garisto

The summer I was 17, my step-grandparents planned a family cruise. I didn’t want to go, but I ended up agreeing out of a sense of obligation. I shared a room with my sister, who was 13 at the time. There was a sliding door that led out to a small balcony, which connected our suite to my grandma’s room next door. Basically, I had no privacy.

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Fortunately, I wasn’t the only person my age on that cruise. There was a whole little community of us that hung out in a designated space called the “Teen Area.” It was a rec room with faux-velvet couches and matching ottomans. I spent almost every evening there with 10 or 12 other people. We passed the time playing games and watching the giant TV, which had a decent selection of movies and shows.

One night, we decided to play trivia, except we made up the questions ourselves. I came up with: “What was the last year the Toronto Maple Leafs won a Stanley Cup?” I didn’t really care about sports, but I assumed it would stump the opposing team since most of them were either American or British.

Without missing a beat, one of the girls answered 1967—which was right. Her name was Sidney. She had dark hair and piercings, one in her eyebrow and another in her bellybutton. “How did you know that?” I asked. She told me she was from Toronto.

We quickly found out that we lived in the same neighbourhood. What were the odds? The two of us drifted away from the game and talked about how we’d come to be on the cruise, what we liked to do in the city, which high schools we went to. I ended up planning a date for us at one of the cafés on the ship.

I was pretty anxious. What if we had nothing to talk about?  To avoid any awkward silences, we ended up playing a version of I-spy. We’d look around at our fellow passengers and give each other points for spying certain clichéd clothing items, like Hawaiian shirts, Birkenstocks or Ray-Bans.

The following evening, we went back to the Teen Area and played truth or dare with everyone. Someone asked one of the other girls if she’d ever had sex. In response, she started crying and said she missed her boyfriend. Apparently, her phone wasn’t working on the ship, and they hadn’t been in touch since she boarded. She begged to borrow my phone and, once I gave it to her, ran off to a remote corner of the Teen Area to call him. The girl who’d initially asked the question then directed it to me. I answered honestly: no. Then other people started to answer. When it was Sidney’s turn, she said no as well.

The following day, Sidney and I were hanging out at our usual spot on the main deck when sex came up in conversation again. It turned out she was ready to try it. She flat out asked me if I would be down. I said that I wasn’t in a rush but that I wasn’t not into it. It felt like the best chance I was ever going to get. So I suggested that we meet up in the evening and then take things to my room. She agreed.

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The only issue was that I would need to keep my sister away for a couple of hours, at least. I’d seen her crossing the deck with a friend she’d made, so I went to find her. I told her I had a favour to ask. “I need you out of the room for three hours tonight.” She was like, “You got it, no problem.” With that settled, I went to get ready.

If it was my first time having sex, I wanted to look nice. I decided to wear a tux. I had been watching a lot of How I Met Your Mother. Sidney, apparently, had a similar idea. She showed up wearing white tights and a colourful dress with flowers on it. We both recognized that this was a rite of passage. The mutual understanding was a turn-on for me. I guess I’m a bit of a romantic.

We didn’t even end up eating—we just went straight to my room. We started fooling around, but after just 10 minutes, there was a knock at the door. It was my sister. Thankfully, we were still decent. “What are you doing here?” I asked her. “I told Mom what you told me and she said to come right back here.” Sidney overheard and said we could go to her room. “My grandma should be out for the night,” she said. So we went. The layout was an exact replica of my room.

We picked up where we’d left off, making out and taking off our clothes. My dress shoes were laced pretty tight, so I didn’t bother removing them—I just took my pants off over top of them. After that, we were ready to go.

The whole affair probably lasted less than three minutes, but in essence it was a success. We’d officially had sex. I felt bad not knowing whether she’d had an orgasm, but I was too awkward and flustered to ask.

Then we heard the door start to unlock. “Oh no,” Sidney said. “You gotta hide.” I dove under the bed, still wearing nothing but my dress shoes. Sidney shoved all my clothes under there with me. Her grandma came in, saying she just had to use the washroom. I rolled out from under the bed while she was in there and continued to get dressed. But, when the bathroom door started to open, I had just my pants on. I ran out onto the balcony.

I was starting to button up my shirt when Sidney’s grandma began walking toward the balcony door. I panicked and walked around the fence to the neighbouring balcony—which turned out to be connected to the room occupied by Sidney’s other set of grandparents. Thankfully, I had only one button left on my shirt. I didn’t bother with the vest. I just balled it up and clenched it in my fist.

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The second I was done dressing, Sidney opened the balcony door, saying, “This is my friend, Noah.” I stepped forward timidly. Her grandma was a bit surprised but very polite. I guess she wasn’t expecting to see a random guy on the balcony with messy hair and a poorly done-up shirt. After all this, Sidney and I left her room and found somewhere to sit. She said, “Do you think I’m pregnant?” I said, “Definitely not.”

The following evening, we stopped at a port near Spain to pick up more passengers. There were some new teens, and one of them, a girl with blonde hair and blue eyes, kept looking at me. Eventually, we got to talking. I guess I accidentally started flirting with her—leaning in close and whispering, giggling, that sort of thing. Maybe it was the confidence I’d gained from my first sexual experience. Sidney definitely saw us, though. Later in the afternoon, when I went back to my room, I found a note that read: “If you ever get tired of blondes, here’s my number.” It was obviously from her.

By then, my family’s time on the cruise was almost over. While I was packing, I found an earring Sidney had left in my room. I texted her, but she told me she’d already left the ship. I’d have to give it back to her in the city.

A week or two later, we met up in Toronto. We had sex again, but it was very casual. Although I liked her, I wasn’t expecting anything serious to come of it. A week after our second hook-up, I sent her another message, but she didn’t answer, and I never saw her again.