Gentlemanly Fantasy Complete
Back in 2014, my girlfriend, whom I met on a dating site, had an acrimonious breakup. I quickly moved out of our apartment in Sydney's north shore and moved to the city's inner west. Unfortunately, the house was small, an old railway worker's cottage and my roommate was not amenable to me bringing back dates. I understood why since the two bedrooms were back-to-back, and we could hear each other roll over in bed. One of us knocking boots would have been intolerable to the other.
Unable to resist, I rejoined the dating site and reactivated my profile with a different username so that my ex-girlfriend, if she rejoined, would not see me. After all, there was a 90:10 ratio of men to women, so being "noticed" by my ex was most unlikely.
I paid for a three-month membership that allowed me to send DMs to people who looked interesting, participate in the chatroom daily, give me access to explicit photos and private galleries and allow paid members to message me directly.
I would occasionally get hit on by men, and while I was partial to that side of my sexuality, I had not indulged in such a long time. Many of the profiles were sleazy or uninteresting and did not appeal at all. I responded to every DM. However, I was very polite with my rejection.
One day, while I was in the chatroom, I struck up a conversation with another paid member named Guy. He was ten years older than me, married with adult children. There was an unusual bonhomie about him that made Guy an interesting person to chat with. He also was not sleazy and rarely brought up the subject of sex.
I perused his online profile, and Guy stated his sexual orientation as bisexual but admitted he had never dipped his toe into the pond. He was an attractive silver fox, and his photos showed a wide smile and sparkling eyes. His bio was about his interests and personality rather than a tedious and seedy 'fuck-it' list.
"Most of the men hitting on me don't do a great job of promoting themselves!" Guy joked.
"Yep, that's for sure," I replied after describing a message I received from a male member while we chatted online one evening.
"When was the last time you met with another dude?"
I described in high-level terms a male-on-male adventure that occurred six years earlier on the west coast of Australia. There was chemistry between us that made the encounter so satisfying.
"Yes, chemistry is important," Guy admitted, "I haven't encountered much of that on here."
"It seems to be a hookup mentality between dudes on here," I said, "You have to work so much harder to score a date with the handful of women."
"I can imagine," Guy replied, "It was hard enough to woo my wife when there was no internet."
Guy was not interested in connecting with another women. He was satisfied with that part of his sex life. He was curious about male sexual relations and had been for many years. Sydney has a thriving gay scene, but did not appeal to Guy. His approach was based on traditional dating: attraction, personality, conviviality and intimacy.
"Even if it's an ONS, I want it to be memorable and worthwhile," He often told me, "I don't want to feel used afterwards."
Guy's consideration brought back a painful memory from a few years ago when I foolishly decided it would be a good idea to meet with an ex-girlfriend from the late nineties. I was used physically and monetarily and felt fully appalled when I was ghosted when the weekend ended.
While I had only been with a handful of men, my standards were much higher than for the fairer sex. I shared Guy's preferences when it came to male partners and felt a nascent attraction to him but kept it to myself.
We chatted daily, mainly platonic conversation, but Guy began bringing up his sexual fantasies with increasing frequency, but it was never unpalatable, which I was happy about. I wondered if he was talking with other prospective partners, but I doubted it.
"Do you fancy meeting up for a drink?" Guy asked one evening.
"Sure, what do you have in mind?"
Guy worked for the local council and we agreed to meet at a hotel in Parramatta which was equidistant from where we lived. Inner West versus Penrith at the foot of the Blue Mountains to the west of Sydney.
"I can be there between 6-6:30 PM," I said after looking at the train schedule.
"Sounds good," Guy replied, "My wife has a work function that day."
When the day arrived, I stayed on the train after leaving work in the CBD and arrived at my destination a little earlier than expected. On the matter of expectations, I tempered them.
"Nice to finally meet you," Grinned Guy after I had downed two beers waiting for his arrival.
We had been chatting online for at least a month by the time of this in-person meeting. After choosing a table underneath a gas heater as this winter's evening was blustery.
Guy looked better in person than his dating profile. He towered over my six foot, very muscular and masculine as evidenced by his crushing handshake. We both dressed in classy suits, reflecting our respective professional careers.
"How was your day?" I asked after handing Guy a beer.
"Better now," He smiled and took a deep draught of the amber nectar, "I fucking hate the public service."
I sympathised since I worked in an adjacent industry and railed constantly at the inefficient fat and outright laziness of many government parasites. Someone with Guy's intellect and ability was hamstrung in such an environment.
We enjoyed a pleasant evening that included a steak dinner and free flowing drinks. At 9 PM we parted at the train station heading in different directions.
I was massaging my hand after its second crushing, my phone pinged. It was from Guy thanking me for meeting.
"I could see myself exploring my bisexual fantasies with you," Guy wrote, obviously nervous about this admission, "If you'd like to, of course."
My cheeks flushed, my smile widened and there was a twitch in my pants.
"If you don't want to then I understand," He added before I could reply to his offer.
"I'd love to explore with you," I tapped, fingers shaking over the letters.
We exchanged further niceties and compliments before settling on a follow-up meeting. This was not an easy task because Guy did not want his wife becoming suspicious of his extra-marital experiments.
"Can you come to Penrith?" He asked.
"Sure," I replied, "I have never been but I know that it is at the end of the train line."
"Let's meet at the Australia Hotel for a drink and go from there?"
"Yep, I can do that," I replied after Googling the meeting place, "When and at what time?"
"Sunday works best for me," Guy tapped, "My wife will be out for a couple of hours."
"See you then."
