A Diary of Travelling and Travel Flings
I found David in an AOL chat room. It started like this:
My then boyfriend, Winston, only wanted to have sex with me once every two weeks and so I turned to the internet in an attempt to make him jealous. It turns out he didn’t even care; the breakup that followed was mutual and amicable.
I kept with the online chatting though. I must have been a chat room creeper’s wet dream then. Sweet little 19, willing to take my clothes off for you on webcam while you jerked off.
One of the men I found was David. There was something kind of timid and sweet about him. He was shy, yet forthcoming. Good sense of humour. What distinguished him the most was that he wrote with proper spelling and grammar.
Our conversations started platonically. Either David was ambivalent about protecting his “real life identity” from me or he was internet-incompetent like some people in their early-40s are. And my curiosity coupled with Gen-Y googling skills very quickly lead me to figure out who he is. Who he’s married to. Where he works. A professor living in New York City. Married with children.
Instead of this scaring him off, it established a bond of trust between us. We told each other our secrets, but we only saw each other through a screen. And we lived in different countries. Close enough to confide in. Far enough to coexist with real-life committments.
I became infatuated with him. He was idealistic, thoughtful, artistic, genuinely witty, and just eccentric enough to be endearing but not weird. He was deeply devoted to his wife. But she rarely slept with him. Most days she didn’t even want a hug. Though he never explained why, he hinted at some sort of traumatic event that turned her off of sex, probably a rape.
And where would he turn to but the internet? Home of impressionable, newly sexually-awakened girls like me.
Our online chats quickly turned sexual.
When I stripped in front of him, I felt like I was unveiling something wondrous. His gaze was hungry but full of reverence, as if he was looking at a particularly beautiful artwork. It was very empowering to be the object of that gaze. His gift was that I never felt like I was doing something dirty or degrading, even as I was tasting my own juices on my fingers, describing what it tasted like (limes, musk, and pennies.)
After the cam-sex we would cam-cuddle. You see, it was an emotional relationship as well. As in, we would lie in bed with the laptop propped up in front of us. And look into each others eyes as if we were really in bed with each other. And touch the screen as if we could actually stroke each other’s faces.
Reader, you are probably cringing (or laughing) as you read this now; believe me, I am cringing as I type it.
After two months of this we drifted apart. I think we both realised we were taking it too far. We exchanged emails every couple of months. He would always add that he still looks at my naked pictures occasionally.
Two years later, I let him know that I was going to be in NYC… Would he like to finally meet? I tried for a tone that neither suggested I was propositioning him, nor ruled it out altogether.
We met in front the Metropolitan Museum, where he was going to show me his favourite paintings. It was closed that day though, so we took a long walk together in Central Park. It was a snowy January day. We were alone.
(Photo from Wikipedia)
David was very nervous. We meandered through the park and then checked into a hotel room where we finally consummated the relationship.
Dear reader, it was much better in my imagination.
Firstly, he couldn’t really get hard. Which is from stage-fright I guess. Other than that, I can’t really think of anything else remarkable about the sex. After taking a break, he came on my chest.
And I had two years of life and many men since I had first met him online, so perhaps I was more jaded than I was then… But he seemed to be just another man to me. He had his admirable characteristics and not-so-admirable ones just like all other men.
The David that I had crushed so hard on 2 years earlier was mostly an illusion. He was more special in my fantasy. My clandestine admirer. My stranger in the night.
The David of reality lived in a different city, was married, and had little in common with me besides being sexually frustrated at a time when I was as well.
I got my first taste of older men at 19.
Mark was a 56-year old who sat down next to me in a bookstore. He was a lawyer who grew up in Toronto but was now living in Bermuda. He came back to his hometown often to visit friends and family.
I wasn’t initially attracted to him. He was about 5’7”, bald, but in great shape. But his voice was sounded, amazingly, just like Nicholas Cage’s. And he was charming, so much so that next thing I know we were having drinks in his hotel lobby. And then we were having drinks in his hotel room. And then I was putting my legs over his lap.
Yup, I was the one who put the moves on him.
I think my panties were constantly wet during our whirlwind weekend fling. It was the Easter weekend and the weather was warm and beautiful. We walked around in parks, went to museums, feasted on oysters. But we never wandered too far from his hotel; our appetites for sex needed to be sated many times a day.
I remember sitting on the statue of Al Purdy in Queen’s Park, my lap in its lap, and Mark standing in between my open thighs. His face was perilously close to my pussy, dripping under my skirt.
It was amazing how turned-on I was by him.
Before he was a lawyer Mark was a jazz pianist and song-writer. He would sing Bruce Springsteen’s I’m on Fire to me while walking down the street. As if people didn’t stare enough at us already… but oh I loved the attention.
I had only had one sexual relationship previous to Mark. To put it frankly, my first boyfriend didn’t like me so much as he liked the idea of having a young, hot girlfriend. But you know something’s wrong when your boyfriend only wants to fuck you once every two weeks. I felt ravenous for sex and attention by the time I met Mark, and he was only too happy to provide.
The great thing about older men is this: they take care of everything. I never worried when I was with him, I trusted him to take care of my needs, to ply me with food and drinks, to satisfy me sexually, to show me new things and to provide a good time. My job seemed to be to just to look pretty, go with the flow, and blow him often. That wasn’t too hard for me; back then I hungered for cock in my mouth the same way I hungered for food.
I even met his 90-something mother! She and I had a hilarious conversation:
Me: Oh, you like operas? I love them too! Which one is your favourite?
Mark’s Mom: Madama Butterfly
Me: I think that’s the most performed opera in North America
Mark’s Mom: Oh yes, it would be. The drama of it! The older American soldier taking such advantage of the young Asian girl!
At which point I burst out laughing. (I’m Asian.)
A month after our weekend fling, Mark flew me to Bermuda for a week.
We rode around the island on his little motorbike, drank dark-and-stormy’s (dark rum + ginger beer), and fucked on every semi-deserted spot we found on those pink-sand Bermudian beaches. The standouts were Elbow Beach and Horseshoe Beach.
I don’t need to write about how beautiful it was there. The photos speak for themselves. Mark loved taking pictures of me, and I loved being his muse. He burned me a CD of all the pictures he took of me. Just accidentally I saw the folder name on his computer “[Wanderslut] in Bermuda.” But I could see that it was part of a large collection of folders “Laura in Israel,” “Roxanne in Korea,” etc. What a player!
When he met his friends, he would introduce me as his “ward” and him as my “guardian.” To which I would reply, “Certainly not my moral guardian!”
It is true that Mark was slightly patronizing to me. I felt that I was his intellectual equal… that was misguided and naive of me. Even if were of the same intelligence, Mark’s experience and wisdom far outstripped a silly 19-year old girl’s. I suppose all women who date older men think themselves precocious and mature.
There was particular song he loved to sing: Steely Dan’s Hey Nineteen. The significance being of course that it’s a song about an older man dating a 19-year old.
The song featured such condescending lyrics like “Hey nineteen, that’s Aretha Franklin. She don’t remember the queen of soul… No we got nothing in common, no we can’t talk at all."
There’s also a lyric that goes “The Cuervo Gold, the fine Colombian, makes this night a wonderful thing.” Mark was kind enough to explain that this meant that the two in the song have nothing to talk about and the man drinks a lot to have a good time. I felt indignant of course, I know who Aretha is!
We once came upon an old tree split by lightning and Mark launched into a story he had once read in a book about the Shahs of Persia. It was about a wealthy man who ruins himself and his fortune when he falls in obsessive love with a young girl. And the illustration accompanying the tale was of a gnarled, bent old tree. Sprouting up in the wasted tree was a young sapling.
"Why are you telling me this?" I asked him, "Could it be a metaphor??" /s
I understand now that what Mark probably enjoyed most about me was my young flesh, but I have no regrets. He remains one of my most fun and uncomplicated flings. And he showed me Bermuda. How can I complain about that?
When we parted he gave me a small gift. It was the novel I had been reading when he first met me in the bookstore: Joey Comeau’s Overqualified. (You can actually read it online here. Yes this is Joey Comeau of A Softer World fame.)
Inside Mark had inscribed this:
You are truly overqualified.
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So, I’ve decided to start a new blog about my favourite things in life: travel and sex.
In a month and a half I am leaving on a 3 month long solo trip to South East Asia. It’ll be a perfect opportunity to gather “material” for this blog! And I’m an old hand at travel flings, so I will write about some interesting past adventures.
I am a 23-year old nomad and nymphomaniac based out of Toronto, Canada. I love thrills, sensory pleasures, and intellectual stimulation, but not necessarily in that order. Occasionally contemplative and often reckless: a combination perfect for telling good stories. Lady in the streets, freak in the sheets, exhibitionist online.
I am in a committed open relationship with my fiance, J. However, when we’re away from each other we live (and fuck) like we’re single.
I maintain anonymity because I can’t stop self-censoring if I know people who know me are reading. I deleted my previous blog because of this. So if you know who I am in real life, I don’t mind if you read this blog (in fact I hope you get some satisfaction for your prurient curiosity, plus some laughs along the way.) Just… keep it to yourself.
The photo above was taken on a secluded part of Horseshoe Beach in Bermuda. I love being naked; it’s the natural state!