My Ladyboy Cupid

How to tell my friends I’m dating a Ladyboy

I took a deep breath, hesitated briefly and clicked on the folder marked “photographs”.

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“That’s the lady I’ve been talking to on MyLadyboyCupid for the last 4 or 5 months,I explained. “She’s a post-op Transgender woman from Manila.”

John and Bill were momentarily speechless. “No way she’s a Ladyboy!” declared John, finally. “She’s beautiful. She just looks like a genetic woman to me.”

“You’re joking with us, right?” asked Bill stroking his beard. “She’s cis-gender, right? Or do you want to see what we’ll say if you say you’re dating a Trans woman.”

“No, really that’s Winnie. She’s really beautiful, right?” I asked, flicking through another 5 or 6 of her photos. “Look at her in a bikini on a beach in Cebu.”

“Stunning,” agreed John. “But what made you join a Ladyboy dating site? Surely you could have found a Ladyboy closer to home in one of the bars or clubs in London? From what I hear there are all sorts of Asian Ladyboys living in UK nowadays.”

There’s only really one effective way to find a Transgender woman

“I’m not sure really,” I replied. “I thought about going to some of so-called “Trans bars” in the city but it’s very much hit and miss. A lot of the Ladyboys who go to such places are only looking for short-term liaisons.”

“And paid for at that,” said John. “Remember when we went to Thailand and met those Ladyboys in Pattaya a couple of years back? Absolutely beautiful but they only interested in short-term relationships.”

Bill laughed. “Yes, short-term meaning one hour or less!”

My nerves about telling Bill and John that I was dating a Ladyboy beauty were rapidly dissipating, and I decided to tell them more. “Actually, I think it was when we met those Thai Ladyboys that I realized that I’d really like to have a girlfriend who is Trans. I’ve read so much about Trans-pinay, Trans women from The Philippines in case you don’t know. The only real dilemma was how to meet a lady I could talk to and get to know before we met.”

“I guess that’s one of the great things about an online dating site,” mused Bill. “It gives you the chance to really get to know someone over a couple of weeks or months before you decide to hook-up.”

“Especially when we are talking about Ladyboys,” I said. “Apart from the issues of finding a nice lady in a club, a Trans dating site leaves no room for error. That’s is, you know all of the girls on MyLadyboyCupid are Trans. No mistakes and no wasting time chatting to a girl only to find she is not Trans. Or worse not available!”

Ladyboys want an easy way to find a man, too

“Well, the same goes for the Ladyboy,’ added John. “Must be very frustrating for the lady if she is talking with a man in a bar and he doesn’t know she is Trans. Then, I can imagine, problems may happen once he finds out. Even violence if the man is an idiot—and there are plenty of them around.”

“Yes,” I agreed. “Dating sites have definite benefits for both parties. Plenty of choices, certainty and quick and easy to join. Then, there is also security issues plus a confidential angle. They keep your data confidential and no-one needs to know you are a member until you want to tell them.”

“Just like you told us,” laughed Bill. “I am surprised I must say. But, there again, it makes a lot of sense if you want to find a Ladyboy. Why waste your time in bars and clubs when you can find several beauties to date simply by logging on to a website in just a few minutes and from the comfort of your home? If I wanted to find a Trans woman, I think I’d do exactly the same.”

“You know I was really quite concerned about telling you both about Winnie. I know you’ll be discreet as you are my best friends. But I don’t want to tell anyone else until our relationship has developed further.” I looked at the center of my watch where the date is shown. “Actually, I’m heading to The Philippines in about a month. Planning to be there for 2-3 weeks and see if Winnie is all she seems to be.”

“Oh, why don’t you go sooner?” asked John.

“Winnie has got her final exams in 2 weeks. I want her to concentrate on her studies and think I’ll be a distraction.”

“What is she studying?”

“It’s the last part of her exams to qualify as a doctor. If she passes, she’ll be able to practice as a GP in a few months.”

“A doctor!” exclaimed John. As beautiful and as young as that. You lucky man! I’m really quite jealous.”

“Well, here’s the link to MyLadyboyCupid in case you want to join and find a Transgender woman of your own!”

“I might just do that,” John replied. “I might just do that!”

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