It was a gloomy Tuesday afternoon. The skies were grey, the weather was rainy and the temperatures were chilly. I found myself on a city train headed towards north of the harbour. It was my first time across the bridge on a train, and it reminded me ludicrously of a recent joke I made with a friend. North of the harbour? Like across the bridge? What's there?
As a visitor who doesn't call this part of the world home, crossing the harbour from south to north can sound very foreign. Much like naive dwellers and visitors on the island of Manhattan who never make non-airport related journeys across the Hudson or East River.
The plan was for the guy to pick me up from Milsons Point, the immediate stop that comes after Australia's iconic steel-arch bridge. I was a little anxious and worried as to how this sex date was going to turn out because firstly, it began as a faceless profile that initiated contact. Then came attached in the chat window were two photos of a good-looking man with a chiseled body. The catch? He's probably in his fifties.
While waiting for him on the side of a pavement, I got carried away in a sea of thoughts. Should I walk away? What if he turns out to be much older than his pictures? Am I sure I want to do this? Why am I so damn nervous? It's not like I haven't done sex dates before.
Then came a loud honk that jolted me out of my thoughts. I hopped swiftly into his car while trying to avoid the rain. The man wore a grey hooded sweatshirt and looked exactly like his picture. Thank God!
In his car, we shot the breeze and that was where I got to feel him out emotionally in flesh. I probably shouldn't be giving unaccredited advice to future 'gay and invisiblers' who are discovering their own experiences when it comes to sex dates, but for me, I tend to rely a lot on instinct, gut feeling and the personal energy that guys carry with them into the date.
A lot of people tend to ask me, especially my friends: "Do you have any idea how dangerous it is? How can you just trust somebody you've never met? With your life? With your whereabouts? With your body?" To be honest, I don't know. I'm afraid I am not at liberty to answer that because every time I meet someone, what I am taking is in fact risks. Big risks with no guarantee.
Back at his big spacious apartment, there was that quick apartment tour, prerequisite glass of water before the first kiss at the dining table. The kiss was not mind-blowing but no complains. The make out lasted for approximately two minutes before we adjourned into his bedroom and got down to business.
He has a really chiseled body which I find amusing for a guy his age. His penis was pretty nice-looking too, with a silver cock ring at the base of his shaft. I've never been with a guy who wore or needed a cock ring so this was interesting. Although it is not up to me to judge what that ring is meant to do.
The session with him was good. Not too long a foreplay, not too long of other things. The blowjob was good, the touching was good, the rolling around in bed was good. I particularly love the part when he rimmed me. He was amazing at it and I suppose he was very clear about his position as a top so I played along with being the bottom again. Jeez, does anybody here ever ask me about what I want for a change?
Then he wanted to fuck me, with protection of course. Initially I was hesitant because I really am not a fan of bottoming for people, then I thought: "Oh what the hell". So with lots of lube and fingers, he finally slid himself in and what I felt wasn't as bad as how I anticipated it to be. As long as it doesn't hurt or provide overwhelming discomfort, I am fine.
When we finished, we cuddled in bed for about twenty minutes before he started giving obvious signals that he should be dropping me back at Milsons Point. During the drive back, I asked him honestly about his age, for I can't see no reason why he wouldn't dare say it now, now that the risk of me rejecting him for his age is gone.
"So, how old are you actually?", I asked and he hesitated big time.
"Hah! My real age or the fake one?", he asked in return with a slight grin.
"The real one. You didn't put any on Grindr. And I mean come on, now that we've had our fun, what's the harm in me knowing? Although just to clarify that it wouldn't have mattered because you look all right."
"I'm actually about two years from sixty"
"Wow! Really? And you still fly?"
"Yes. It's a job and the airline allows us to stretch our years to keep working."
"Wow. You do keep yourself looking very good. I mean for a guy who is entering his sixties? I have to say that you still look pleasantly good in comparison to what many of us would become when we turn sixty."
"Why thank you."
"Really, I am just in awe. I mean if you're gonna ask God for a gift, you might as well ask him to let you age gracefully. Seeing you today, it kinda made me wonder how I would look like when I'm nearing sixty. But probably not as good as you I might have to say."
"What is the oldest person you have ever slept with?", he asked.
"Now that you've told me your age, definitely you!", I answered with a non-judgemental smile and he chuckled.
After turning a couple of corners, we were finally back to where he first picked me up. I shook his hand, said my goodbye and got out of the car. Back on the train, I couldn't believe that I actually had fun with someone who was almost sixty. On one hand, it was very tempting to judge myself. But on the other, I was very grateful for the entire human experience that came to me in the form of him.
As a visitor who doesn't call this part of the world home, crossing the harbour from south to north can sound very foreign. Much like naive dwellers and visitors on the island of Manhattan who never make non-airport related journeys across the Hudson or East River.
The plan was for the guy to pick me up from Milsons Point, the immediate stop that comes after Australia's iconic steel-arch bridge. I was a little anxious and worried as to how this sex date was going to turn out because firstly, it began as a faceless profile that initiated contact. Then came attached in the chat window were two photos of a good-looking man with a chiseled body. The catch? He's probably in his fifties.
While waiting for him on the side of a pavement, I got carried away in a sea of thoughts. Should I walk away? What if he turns out to be much older than his pictures? Am I sure I want to do this? Why am I so damn nervous? It's not like I haven't done sex dates before.
Then came a loud honk that jolted me out of my thoughts. I hopped swiftly into his car while trying to avoid the rain. The man wore a grey hooded sweatshirt and looked exactly like his picture. Thank God!
In his car, we shot the breeze and that was where I got to feel him out emotionally in flesh. I probably shouldn't be giving unaccredited advice to future 'gay and invisiblers' who are discovering their own experiences when it comes to sex dates, but for me, I tend to rely a lot on instinct, gut feeling and the personal energy that guys carry with them into the date.
A lot of people tend to ask me, especially my friends: "Do you have any idea how dangerous it is? How can you just trust somebody you've never met? With your life? With your whereabouts? With your body?" To be honest, I don't know. I'm afraid I am not at liberty to answer that because every time I meet someone, what I am taking is in fact risks. Big risks with no guarantee.
Back at his big spacious apartment, there was that quick apartment tour, prerequisite glass of water before the first kiss at the dining table. The kiss was not mind-blowing but no complains. The make out lasted for approximately two minutes before we adjourned into his bedroom and got down to business.
He has a really chiseled body which I find amusing for a guy his age. His penis was pretty nice-looking too, with a silver cock ring at the base of his shaft. I've never been with a guy who wore or needed a cock ring so this was interesting. Although it is not up to me to judge what that ring is meant to do.
The session with him was good. Not too long a foreplay, not too long of other things. The blowjob was good, the touching was good, the rolling around in bed was good. I particularly love the part when he rimmed me. He was amazing at it and I suppose he was very clear about his position as a top so I played along with being the bottom again. Jeez, does anybody here ever ask me about what I want for a change?
Then he wanted to fuck me, with protection of course. Initially I was hesitant because I really am not a fan of bottoming for people, then I thought: "Oh what the hell". So with lots of lube and fingers, he finally slid himself in and what I felt wasn't as bad as how I anticipated it to be. As long as it doesn't hurt or provide overwhelming discomfort, I am fine.
When we finished, we cuddled in bed for about twenty minutes before he started giving obvious signals that he should be dropping me back at Milsons Point. During the drive back, I asked him honestly about his age, for I can't see no reason why he wouldn't dare say it now, now that the risk of me rejecting him for his age is gone.
"So, how old are you actually?", I asked and he hesitated big time.
"Hah! My real age or the fake one?", he asked in return with a slight grin.
"The real one. You didn't put any on Grindr. And I mean come on, now that we've had our fun, what's the harm in me knowing? Although just to clarify that it wouldn't have mattered because you look all right."
"I'm actually about two years from sixty"
"Wow! Really? And you still fly?"
"Yes. It's a job and the airline allows us to stretch our years to keep working."
"Wow. You do keep yourself looking very good. I mean for a guy who is entering his sixties? I have to say that you still look pleasantly good in comparison to what many of us would become when we turn sixty."
"Why thank you."
"Really, I am just in awe. I mean if you're gonna ask God for a gift, you might as well ask him to let you age gracefully. Seeing you today, it kinda made me wonder how I would look like when I'm nearing sixty. But probably not as good as you I might have to say."
"What is the oldest person you have ever slept with?", he asked.
"Now that you've told me your age, definitely you!", I answered with a non-judgemental smile and he chuckled.
After turning a couple of corners, we were finally back to where he first picked me up. I shook his hand, said my goodbye and got out of the car. Back on the train, I couldn't believe that I actually had fun with someone who was almost sixty. On one hand, it was very tempting to judge myself. But on the other, I was very grateful for the entire human experience that came to me in the form of him.
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