This is the second story follow up for my first time experimenting with a ladyboy (newhalf) that I’d arranged in Tokyo, last year. I am not exactly the studliest of men, as a matter of fact, I’m a husky hairy guy who has been called attractive. I have a lot a few sexual exploits and after reading for so long I thought I’d share some of my riskier or better exploits. Any PMs or comments are welcome
After my first run in I was conflicted… I was really turned on by the experience but after how rough the ladyboy had been with me I wasn’t sure about paying for and having the experience again without knowing what I really wanted.
I live and travel in Vietnam, so I have a wide access of ladyboys from the area and I’d been searching through social media and craigslist looking for my next hookup. I would send some test messages… I figured if a girl wasn’t willing to exchange some messages then she wouldn’t be receptive to my first time nerves. After while I found a ladyboy that was quite beautiful but not heavily operated on. She, I’ll call her Di, spent time to talk to me and ask me what I was interested in and after some back and forth we arranged a time to meet in the evening.
I was so nervous after my first encounter that I made sure to have a couple of drinks and an ativan before meeting with Di. When she opened the door she was more beautiful then her pictures, which I found to be surprising. She was wearing a sexy little button up top with a skirt and high heels. She didn’t ooze sexual appeal, but she was confident with me and aware that I was nervous. She started to undress me and soothe me. She ran her hands over my body and undressed herself. I could feel her soft panties against my ass, her dick pressing through as she kissed down my neck and slid my boxers down to get me completely naked.
Di played with my dick for a little bit while whispering dirty things in my ear… teasing me about being straight and how her dick felt. She told me to reach behind and play with it. It was much smaller than I would have liked, but it was fun to play with. She sat me down on the bed and took off her bra, revealing her small, almost non existent breasts and slid down her panties to reveal her dick.
We made small talk as she moved behind me to give me a massage… laying my down on my back and pouring oil down my back. She straddled me with her dick pushing in to my ass crack. I was so nervous… I wanted to push her dick in my ass right there but she wouldn’t budge until she had finished the massage. She worked her oiled hands down and slid over my anus. She rubbed me butt and spread my cheeks, probing my asshole with her finger and making me moan a bit.
She flipped me over and started to work on the front of my body. She started with kissing me on my neck and working her way down to my hard dick. I watched her and she made eye contact while she swallowed my cock whole. It’s a strange feeling… looking a ladyboy in the eyes while she licks your balls. The feelings are very sexy and conflicting. It was hard for me not to come as she made nice, long strokes with her throat. I’m not huge, but at 6.5 inches, it can be a struggle to get it all down.
After the blowjob, she sensually talked dirty to me and grabbed the lube while mounting me. She put her dick and balls on top of mine and squeezed them together, stroking her dick with my dick. THIS FELT SO GOOD! If you ever have a chance as a dude to get a second dick, put them together and stroke them. If one of you cums, keep using it as lube. Trust on this.
I won’t even act like I’m some adonis. I would have loved to fuck more. In actuality, we had a really great connection and as she talked dirty and rubbed our cocks together, looking deep in my eyes, I lost it… My body started to convulse. She actually screamed no, she didn’t want me to come like that. It gave me quite a laugh.
It was a little embarassing actually but she was understanding and said she regretted that I hadn’t said anything as I hadn’t brought money to have a second shot. But to follow up on the connection, after I was finished i laid with her for an hour, stroking her dick and taking turns playing with eachother while we talked about circumstance and travel, her journey as a ladyboy. Not exactly the “sexual” stuff you expect but something I enjoy… I was only supposed to be there for an hour and a half but we ended up laying in bed for almost three hours (No extra charge, so you know it’s real ha) since we had such a great connection. We even said we’d meet again when she came back to Vietnam and we have had some phone chats. I’m excited to see if we have another adventure, as she’s mentioned role play and really experimenting with some of my fantasies.
Maybe not quite the ending you expected, but it was a really hot experience and it’s changed my outlook after my first session. It’s made me hungrier for ladyboys and regular cock, I’m currently trying to find a couple to experiment with and to tell my gf about my desires. I definitely can’t tell her about my experimentation though.
Source: reddit.com/r/gonewildstories/comments/8rw9vl/my_second_time_with_a_ladyboy_in_asia
Fascinating! Thanks for sharing!