Date and location of initial meeting: Sydney, February 2016
I matched with the Entrepreneur in mid February 2016, and after a few back and forth messages, he was quick to arrange a date. We made plans to meet up on a Saturday night at Papa Gedes in the city.
When I got there, the Entrepreneur was already there standing at the bar, but I missed him and sat down. He soon found me though, and we sat down and had a drink. I would rate him on the scale as average to cute, but in person, there was something about him that made me want to hold his face and kiss him. The Entrepreneur was from Seattle originally and had just recently moved to Sydney after living in SF for two years. He was a 4th generation American, but had Japanese and Chinese heritage. He was currently working on bringing a software engineering school to Sydney.
Our conversation flowed smoothly and naturally. I told The Entrepreneur about my near-future plans to move to New York, and he seemed very enthusiastic about this, and said that he might be moving there in a year as well. By the end of our first round, The Entrepreneur asked if I wanted another drink. I asked him if he wanted to bar-hop, and he said we could walk around Darling Harbour and drink wine at his place.
And so we walked back to his place, and settled down on the balcony there drinking wine and chatting. After two glasses of wine, he leaned and kissed me, and we made out for awhile but then resumed talking. Shortly after that, his two gay flatmates returned home, and said hello to us.
Entrepreneur and I continued to drink and chat on the sofa, and then decided to go to Arq, which is one of Sydney’s most notorious gay clubs. We got an Uber there, and while waiting for it, Entrepreneur made playful little ways to touch my body. We spent maybe 2 hours at Arq, dancing and chatting, and making out. While at Arq, Entrepreneur made a comment about how he had been in a BDSM parade before in the US, and in my intoxicated state, I must not have been able to conceal my interest, because he turned around with a curious expression on his face, and asked whether I liked that sort of thing. I didn’t say no, and he leaned in and kissed me passionately.
We didn’t stay much longer after that, and got an Uber back to the CBD, where we ate bad Chinese food and also basically got kicked out of the restaurant because they wanted to close (it was only 2am by this point, but Sydney is a city that sleeps, unfortunately for us night owls).
We walked out of the restaurant, and I told Entrepreneur I was going to Uber home, and he kept saying to come back and hang out at his place, while I said that it was out of the question as I had a full day of hiking tomorrow and I didn’t want to be tired. We stood on the street corner for about 5 minutes, Entrepreneur protesting that he “didn’t want to do anything” and me, saying that I was leaving. There was something a bit childish in the way he insisted it, and it was a bit of a turn off really. I was glad when he finally let me leave.
He texted me shortly after saying he had fun with me that night, and we should do something again soon.
Soon, happened to be a few days later. He had initially asked me to go for a picnic on a Thursday, but on Wednesday he had instead had some meetings cancelled, and so invited me to go paddle-boarding. It was a hot day, and so, excitedly, I got ready for paddle-boarding and wore my bikini underneath my clothes, but when I was about 10 minutes away from the city, Entrepreneur messaged me and said that apparently the wind was picking up and we wouldn’t be able to go paddle-boarding anymore. He then told me to meet him at his place instead, which annoyed me quite a bit. I wondered if this had been his plan all along.
However, when I got to his place, he was just packing up his things and didn’t try anything. We decided to go to Old Clare Hotel for a swim, and hung out there, before grabbing gelato at Central Park and then playing table tennis. I managed to play horribly (as usual) and we didn’t play for very long, before he came around to my side of the table and laughed and hugged me, seemingly suggesting that my inability to play table tennis was simply to horrible to put into words.
After that, we sat on the sidelines discussing our childhoods, holding hands and generally opening up to one another, when he asked if I watched television. As a seasoned Tinder veteran I knew where this was heading, and Entrepreneur began talking about this television show that he wanted to show me.
Not wanting to end the evening, I agreed to come back to his place. We grocery shopped for some ingredients for dinner, and then when we got back to his place, he cooked a simple dinner of roast salmon and asparagus for the two of us, which we drank with chardonnay.
Afterwards, we went into his room, and Entrepreneur proceeded to try and download Rick and Morty. I felt slightly annoyed at his lack of preparation, and was considering leaving then, but I didn’t. The show downloaded quickly, and we lay there on the bed not touching, but gradually I moved in towards him, and we made out for a bit.
He moved his hand into my shorts, and I decided things were moving too quickly, so I pulled away and murmured that I should probably go home. Entrepreneur took the hint and backed off and said “we don’t need to have sex”. We just cuddled then, but shortly after we started making out again, and I’m ashamed to say that I was the one who started it, and also who initiated sex after that.
I completely contradicted myself, and I felt like I couldn’t control my urges anymore. Entrepreneur had a giant penis (surprisingly) and we had great rough sex, to the point where I was dripping wet. But afterwards we put our clothes on awkwardly and hurriedly, like we hadn’t just exchanged bodily fluid.
I decided to leave shortly after that, and he didn’t walk me to the station, but kissed me goodbye at the door, and I was sure I’d never hear from him again. Honestly, I felt quite shitty after that. It was the first time since my Craigslist BDSM encounter that I felt so bad after sex. I cursed myself for not having greater urge control and went home feeling utterly miserable.
It was then that I started to wonder if I should stop having casual sex.