Ladyboy First Time

Ladyboy First Time
How was your first experience with a ladyboy in Thailand?
BU Head ( 2003 – present ) · · 6 mo ·
What’s the naughtiest experience you’ve ever had with a trans person?
As a straight person, have you ever accidentally gone home with a transsexual? If so, what was your experience?
What are the best websites to date ladyboys?
Is it normal to be in a relationship with a ladyboy in thailand?
How does it feel to be married to a transsexual woman?
I own my own retail business · Author has 71 answers and 827.3K answer views · 2 y ·
What’s the naughtiest experience you’ve ever had with a trans person?
As a straight person, have you ever accidentally gone home with a transsexual? If so, what was your experience?
What are the best websites to date ladyboys?
Is it normal to be in a relationship with a ladyboy in thailand?
How does it feel to be married to a transsexual woman?
A ladyboy invited me to her place in Thailand. Should I go there or take her to my hotel? Why not here place?
What is the difference between a ladyboy and a transsexual? Can I see some pictures?
What's it like dating a ladyboy, aka a “kathoey”?
Have you ever had a massage from a ladyboy?
Is it okay to sleep with a trans person and be straight?
When was your first underage experience?
As a trans person, what has been your biggest “oh shit” moment?
How often do Thai ladyboys live as men when they grow old?
Is it true that males are changing gender to earn money in Thailand?
What is your experience with a transgender woman?
What’s the naughtiest experience you’ve ever had with a trans person?
As a straight person, have you ever accidentally gone home with a transsexual? If so, what was your experience?
What are the best websites to date ladyboys?
Is it normal to be in a relationship with a ladyboy in thailand?
How does it feel to be married to a transsexual woman?
A ladyboy invited me to her place in Thailand. Should I go there or take her to my hotel? Why not here place?
What is the difference between a ladyboy and a transsexual? Can I see some pictures?
What's it like dating a ladyboy, aka a “kathoey”?
Have you ever had a massage from a ladyboy?
Is it okay to sleep with a trans person and be straight?
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I am a single, mid 40s female. My job requires me to travel a lot.
On one such trips, I got along with one of the receptionists at the hotel I had stayed in. I'd constantly invite her to my room, have drinks, discuss sex. She would always brag about how a friend, a ladyboy, of her would always give her multiple orgasms. I asked her if she'd help hook me up with her friend and she immediately agreed.
Next day, she turned up with her friend. It turned out to be one of the best days of my life. I ended up completely surrendering myself to him. He gave me several earth shattering orgasms and climaxe
I am a single, mid 40s female. My job requires me to travel a lot.
On one such trips, I got along with one of the receptionists at the hotel I had stayed in. I'd constantly invite her to my room, have drinks, discuss sex. She would always brag about how a friend, a ladyboy, of her would always give her multiple orgasms. I asked her if she'd help hook me up with her friend and she immediately agreed.
Next day, she turned up with her friend. It turned out to be one of the best days of my life. I ended up completely surrendering myself to him. He gave me several earth shattering orgasms and climaxed in my rear. We spent the rest of the day cuddling on my bed.
My cousin and I (two mid 40s sex starved single ladies) were staying on holiday in a small hotel in the tourist area of Bangkok last year. We used to chat to the lady owner in the little bar at night and watch guys arrive with sexy young ladies and go to their rooms for sex. The owner told us that some of the ladies were “ladyboys”; we would never have spotted it.
The owner told us that some of the ladyboys were “female friendly” if we were interested in having an experience she could arrange it for us via an agency rather than us finding freelancers or going in bars etc.
My cousin and I (two mid 40s sex starved single ladies) were staying on holiday in a small hotel in the tourist area of Bangkok last year. We used to chat to the lady owner in the little bar at night and watch guys arrive with sexy young ladies and go to their rooms for sex. The owner told us that some of the ladies were “ladyboys”; we would never have spotted it.
The owner told us that some of the ladyboys were “female friendly” if we were interested in having an experience she could arrange it for us via an agency rather than us finding freelancers or going in bars etc.
We decided to do it for a giggle and within 30 mins she had 2 arrive at the bar (not giving us time to back out). The hotel owner sold us a box of condoms and we went up with the ladyboys to our twin room. My cousin and I have done group sex with boyfriends together since we were teens so no discomfort there.
When got to the room and naked I was fascinated by their bodies. They were early 20s with fabulous bodies; hard to imagine that they are basically guys with boobs and wow they had great boobs and then lovely cocks and balls down below. The one I was having wanted to try my sexy bra on and loved it and we swapped bras; his/hers was a sexy front-fastening with push up, I still have it.
Well the oral I got was the best ever, followed by a long, solid, vigorous banging that blew me away. After they had fucked my cousin and I, they wanked each other off which was so sexy to watch.
We had booked 3 hours and so after a little rest they asked if we would like a Yoni massage which I had never heard of. Anyway we went with it and basically they massaged our pussies until we climaxed. My tranny used a combination of internal massage on my G-spot and external stimulation around my clit.
Because we booked and paid via the hotel lady we probably paid over the odds but it was well worth the money.
We were due to visit again this year for some more fun but the covid19 has put the damper on that for a while yet.

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