A night out with a Thai ladyboy | 2016

I am a very straight guy. I've never been turned on by a man in the slightest way. I have a couple of gay friends who I am completely comfortable around. But no matter how "good" they look when they're all dressed up I never think anything other than, "how funny, he's trying to be pretty, but he's still an ugly man." So my initial thought when my girlfriend suggested we go to see a ladyboy cabaret during our vacation in Thailand this summer was "what's the harm".

We showed up and a squadron of men in drag were lined off outside, in full costume like it was the Brazilian carnival, wooing customers for the show that was about to start. They were all obviously men, and no amount of makeup had changed that. I was neutrally surprised, since I had heard so many stories of the indistinguishable Thai ladyboys. Anyway, I knew the cabaret would be pretty mild and nothing like a sex show, so I didn't really care.

We went in and the show started, with obviously manly participants. A couple were pretty and had feminine faces, but I always saw them as men. I started to become aware of the tiny details of femininity which were often a giveaway. Bony knees and ankles, large shoulder blades (or was it should muscles?), and something about the cheekbones and the jaw. They pranced about onstage performing routines that would have been risqué in the 20's. It was pretty good entertainment, and fairly harmless. At one point they were wearing thongs. The nudity gave me the kind of feeling that you get from seeing a muscle chart in a biology book. "Oh, buttocks".

As the show went on, the waitress came over, a young thai girl with a pretty, round face. We ordered some (expensive) drinks and continued watching. As the show progressed I started to get confused. Some of the ladyboys had feminine figures, feminine faces and virtually no masculine features. Two were very pretty, and rather sexy. I found it was funny that i thought so, and told my girlfriend which ones I liked.

Eventually, the show wound up. The DJ switched to party hits, and some rubes from the crowd got pulled on stage. The music was actually pretty good, and we started dancing too while we finished our third round of beers.

Eventually, everyone had left and it was just us dancing. The ladyboys who were still around came over to dance with us. One was older and milf-ish, one was fairly overweight, and one was the waitress I had thought was a girl. She said something to us in a soft, feminine voice. But there was no mistaking it - she was definitely a ladyboy. I found her so sexy that the realization threw me off. I actually felt somewhat repulsed, like she had fallen in attractiveness by this revelation. Not that it mattered, my girlfriend and I aren't in an open relationship or anything.

After some more dancing, my girlfriend came over and told me the ladyboys had invited us to go out dancing somewhere new with them. That seemed like way more fun than the sterile cabaret, so off we went.

We all walked off and the older ones, in their very manly voices and broken English, basically said they were too old for this shit and were going to sleep. They left promptly, leaving us with the young waitress. She told us to come with her and we walked to a main street to find a tuktuk. As we walked and talked with her, I noticed she had somehow exposed more of her cleavage. She was overall extremely attractive. It confused me. It gave me an erection.

I have no idea why this turned me on so much. I have never been attracted to anything but a woman, and here was this very feminine, very sexy person who was neither woman nor man but some new category (which also made me think my girlfriend had no need to be jealous). Being so confused about what was happening to me only seemed to turn me on even more.

We reached the main street and hailed a tuktuk. A tuktuk is basically a motorbike with a two-person seat attached to the back, so it normally seats just two. We got in with my girlfriend on the right, me in the middle, and the ladyboy - Katy - on my left. Since it was a pretty tight fit, I had my arms up on the seat back. i was touching my girlfriend on one side, but not touching Katy on the other.

It occurred to me that I should have put my arm around Katy as well, just for fun. But it was kind of too late. I tried inching forward, but felt a little silly. I stopped. I still wasn't touching, but I was close. Then I came up with a trick that I thought was clever. I leaned forward to look at something on my right, so that my left shoulder naturally came forward. I very lightly pressed against Katy. I felt kind of childish and was going to go back when I felt a small push back against my shoulder... So soft and feminine and shy, it really turned me on. When I leaned back again, Katy came with me and snuggled discreetly. But only two seconds later, we arrived at the bar.

I had thought we were going to meet her friends somewhere, but it ended up being just the three of us. I felt a little awkward, but we ordered some vodka mixers and took a table. My girlfriend and I sat down but Katy obviously wanted to dance so we stood back up, near to the table.

Both my girlfriend and I were fascinated by Katy, and we asked her about herself after some alcolubrication. She had been taking hormones since nine and had had breast implants. That meant she hadn't gone through puberty. Does that make her a girl? A girl with a history different from other girls? I was still grappling with how sexy I found this non-woman.

Did she even have a penis? While my gf was in the bathroom, I drunkenly asked Katy this directly. She blushed and said yes. I had expected that. But I was confused that it didn't turn me off. I was still convinced that Katy was a she, a very sexy she, just a special she. But she wasn't a girl, so my girlfriend didn't need to be jealous. I drunkenly touched Katy's lower back. It felt unsatisfying, and a little too muscular. There wasn't enough of that girly softness which I love. Soon after, my gf returned.

After the first touch, I was continually turned on, fascinated and confused. I wanted to experience this Ladyboy. I felt like my girlfriend had no reason to be jealous, since Katy wasn't a girl. But like I said we weren't really in an Open relationship. Still, every time my gf went to the bathroom I got as close as I could with Katy. I became more and more forward. The first time, I had just touched her lower back. The second time, I grabbed and squeezed her ass, and caressed the space between her skirt and shirt.

I never doubted that she wanted me to do this, I don't know why. With a girl I would have been almost certain that I would be called out, and I would never have risked it. Maybe because of the tuktuk incident, I felt confident that my desire was reciprocated and confidential.

Also during the second time, we ended up dancing back to back with her ass against mine. I couldn't actually feel her ass, she was wearing some kind of Robin-Hood-Men-in-Tights underwear that gave away less than normal jeans do. No idea what that was all about.

The third time my girlfriend went to the bathroom, I was still erect from my confused but powerful attraction. I moved close towards Katy and rubbed my cock against her thigh while murmuring something bold and obscene. She asked me if I had a six pack and put her hand inside my shirt, then suddenly pushed me off of her. I shrugged to myself and kept dancing. Then suddenly, my girlfriend was at my side only twenty seconds after she had left. Shit! She had definitely seen me.

"You didn't give me enough change for the toilet." (The toilet was public and had an attendant that you had to pay each time, as is common in Thailand.) I gave her more change and she went. This time I only talked to Katy and kept a safe distance.

When my girlfriend returned, she acted completely normal. Okay, so she wasn't jealous. I began to drunkenly imagine that she was as attracted to Katy as I was, and that there was a possibility that we may all end up in bed together that night. So I didn't worry about it but I thought I would probably get in trouble later...

We continued drinking, me partly fuelled by my sexual confusion and desire. With some more time and alcohol, I became convinced that my girlfriend hasn't seen anything. So, I became more reckless.

The next time my gf went to the bathroom, I again made advances on Katy. Fully erect from the excitement of sexual confusion, I pressed my cock firmly against her, moved close to her ear, and declared, "I want you." She moved slightly back, creating a gap between us. But she wasn't rejecting me. She slipped a hand between us and squeezed my shaft for a full second. She released it and moved closer to the tip for a second full squeeze while repeating the same words more emphatically, pausing after each: "I want you." I was utterly turned on. It was the first time anyone but my gf has touched me in years.

Eventually, the party wound down and we had to leave. We grabbed a tuktuk and piled in as before. I was now fully drunk and fully aware that my ridiculous idea of a threesome was not going to happen, and my excessive drinking would probably also not be repeated in the near future. But I was still overwhelmed with curiosity about this Katy creature and this was my last chance.

As we sat in the tuktuk, I put my arm right around Katy's waist and on her outer leg. I moved to hold her hand briefly, it felt large and veined and manly and I drunkenly released it and put the thought out of my mind. I went back to her smooth, soft leg and noticed that her pretty large purse was making a wall between my hand and my girlfriend's eyes. What a coincidence. I unashamedly began stroking Katy's inner thighs, they were smooth and soft and had strange grooves between the hamstrings and the quads. It was an extremely exciting exploration of new sexual territories that had never before been explored.

After exploring her legs, I began to wonder about the space between them. I tried to push her panties aside. But they were literally inflexible. I cupped, and felt a vague warmth and nothing more. I threw caution to the wind, I moved my hand to the waistline, I pushed inside, I reached in to feel the smooth skin in the No Man's Zone, I pushed deeper in search of the truth, finally, I came to a small area of softer flesh.... It was completely unidentifiable. It was probably the base of a small penis that was folded down under the legs, but it felt vaginal. I was confused, not turned on. All of a sudden we arrived at Katy's house, and she got out, said goodbye normally and went in. The tuktuk carried on to take me and my girlfriend home. I passed out almost instantly. My dreams of a ladyboy threesome remained a fantasy. Maybe it's better than she was wearing those impenetrable panties.