July 8, 2024

I am a thirty-seven-year-old crossdresser living overseas in southern Japan and I have recently started going out dressed up.

It started funnily one day when I just decided I would put on a skirt while in a park and crossed the road to go into a shopping complex. I wasn't even disguised, and two young women noticed me walking towards them, and shared a laugh as we passed. What a cool feeling, exposing my legs, and flaunting my ass in panties riding the excalator, and it led me to plan going out again, but dressed more fully. So that's what I did.

As weeks passed by, I found a few more opportunities to go out, dressed with a wig, heels, jewelry, shoulder bag, even lipstick, but no other make-up. And I covered my appearance with a surgical mask, which I realised was against the point. Nevertheless, I presented myself openly, but always away from my neighbourhood, and I felt quite excited but nervous at the same time. With the goal of looking as feminine as possible, I had bought hip pads, and breast forms to achieve some curves.

While people each crossdress for their own reasons, I began to realise that I wanted people to see me as an object of sexual curiosity. Throughout my life, I had/have had only me to female sexual encounters because I'm totally hot for women, but dressed as a woman, I started thinking about sex with men, which led me to search for ways to meet them.

A few times out in the streets at night on the weekend, resulted in laughter, incredulity, and a couple of friendly conversations too. But no sex. Finally, I found this webpage that had a forum and bulletin board about lgbt activity, and I started posting messages, and others replied. Unfortunately, although I can speak Japanese somewhat, communicating by text presented misunderstandings, leading to missed opportunities.

One afternoon in May, I announced to the forum that I was going to a local park that night. After showering, shaving all over, smoothing and moistening my skin, I set out my clothes and accessories. I, then painted my toe nails and applied make-up to my face, leaving off mascara and lipstick. Spraying my body lightly in a floral, scented perfume, I prepared to dress. I got dressed in a cute, blue and white, horizontally striped, bodycon, sleeveless dress with a scoop neck and knee-length hem. Underneath, I was wearing a matching, lavender-coloured bikini and bra set with a satin finish. Accentuated with breast forms and hip pads, held into place by a pair of sandalwood, open-crotch pantyhose, I felt I had the curves I needed to look feminine, on my 5'8". 150lb body. I was almost ready.

I carefully did my eyelashes with mascara and painted my lips. After looking closely in a mirror, I finally applied artificial fingernails, matching the colour of my lips, toe nails, panty and bra. The fingernails and make-up are hardest parts for me to do. Almost last but not least, I slipped on my jewelry. I had chosen a ring for each hand, plus a necklace running through an open heart pendant. All in silver. I then put on my dark-brown, wavy, shoulder length wig that I had found in a thrift shop, very near the park I was going to.

Looking into the little white shoulder bag, I was taking with me, I made sure I had what I would need. Moving to the front door, I wrapped my shoulders in a wide, cotton scarf, the colour of matcha, before slipping into white, three-inch, high-heeled sandals with ankle straps. And out the door I went.

After locking my door, I descended one flight of stairs to the ground outside, my heels making a sexy, clackety-clack sound. I was very excited but also worried that any of the neighbours should see me. Still, it was 11:30 at night on a Saturday, and the six dwellings in our building were housed with young families, apart from mine, so I wasn't too worried. I walked to my car, opened the door, got in and drove away.

On the way, I stopped to buy a bottle of water at a Trial discount store, on route 3. Although I felt a bit shy, no one caused me any problems, and I arrived in the carpark in front of the park a minute or two later. It was about 11:45 then, and the air was warm and moist. A beautiful May night.

I looked around but didn't see anyone, although a steady stream of cars, pedestrians, and cyclists behind me on the main road provided a consistent hum. I got out of the car, approached the steps into the hilly park, and climbed, reaching the first plateau. I felt so free in the dark, and as I scouted the area, I practised walking and moving my arms, shoulders, and hips in a feminine way.

At midnight, I checked the website's bulletin board and, noticed a little bit of activity in the thread I had created hours earlier. Although I tried to understand what was written, I wasn't sure if anyone was interested, and walked up more steps, and further into the park. I was having fun but was disappointed at the same time. There was no one around. I decided to go back down below.

As I was going down these long stairs, I noticed a group of five young guys entering the park in front of me, so I stopped and watched. They were then in the lower plateau, talking in a circle. I wondered what they were doing there, hoping and not hoping that they were looking for me.

I turned around and started climbing again, with my heels click, clacking on the steps; a very distinct sound, I thought. Looking back over my shoulder, and down the way, no one moved but I thought I had caught their attention. When I reached the top again, I realised that none of them were going to follow, and I considered what I already knew about Japanese people and their passive ways. It was getting later and I wanted something to happen, so I walked back down the stairs toward them, reaching the landing where they were, only fifty or sixty feet away. I rested against a stone wall, trying not to fidget. Still nothing.

Here goes, I thought, and I walked toward them, saying hello. Their voices quietened a bit, but someone replied, and we started talking.

While I felt that I had made myself look somewhat girly, I must've seemed quite odd. I was standing about six feet tall.

As we were chatting, I explained that I was from England and they asked if I was a guy, which I confirmed. This emitted a bit of chuckle but they were very polite, and said that I looked nice. Anyway, this didn't seem like it would go anywhere, and I was just about to excuse myself when two of them said their good byes, so I resolved to stay a bit longer.

Another minute passed, and two more guys left to go in one direction, with the third in another; up the steps. I decided to try for the single guy, and followed after him. Catching up, I linked my arm in his and asked if he wanted to play. He said he was tired and going home but I persisted gently, and he didn't run off, so I walked with him a little more, saying I wanted to give him a blowjob. He wasn't so sure and we started climbing the steps together.

When we reached the top, he still hadn't gone, and as we came upon the public toilets up there, I led him into the area for people in wheelchairs. Allowing me to feel his bulge through his pants, I asked if I could kiss and lick his penis. Embracing him slightly, he could feel my breastforms on his chest. He reached up and touched a little. I returned his touch, and caressed his cock a little more. I asked again, and he said a blowjob would be ok. I was thrilled!

I slid down onto my heels and pulled his clothes lower, freeing his penis. Touching his penis with my hands and fingers, I moved closer, and started breathing on it, and then I kissed it. I kissed it again, and starting licking the tip. Kissing and licking. Using my tongue, I swirled his knob, one way and the other, kissing and licking it.

Realising I wanted to make a good impression, I applied a fresh layer of stick to my lips and returned my attention to his penis. Opening my mouth, I slowly enveloped his head as I looked up into his eyes. I kissed, licked, slurped and sucked the tip of his cock as well as I could. I licked and kissed up and down his shaft. Lowering his pants a little more, I cupped his balls in my hand and tickled the underside gently. He was so quiet.

With my hands lightly on his legs, I parted my lips again and covered his penis. I continued taking him more and more into my mouth, moving my head in and out, up and down on his shaft, wanting him to enjoy my mouth. He wasn't getting fully hard, though, and I felt a failure, so I asked him what he liked or what I should do. He then put his hand behind my neck and began pushing his penis into my mouth. What a turn-on!

As he began taking more control, his penis started to swell, and I kept working on the head and shaft wanting him in my throat. He wasn't very large, so that never happened, but I kept doing my best to please him. Quickening his pace, I felt very comfortable and wanted more. Sucking on his rod with my mouth and my tongue sliding under his shaft, I jubilantly felt his semen squirt in my mouth. I was overjoyed and moaned with pleasure. His cum tasted mild, and although he hadn't cum a very lot, I had finally gotten what I wanted, and thanked him. Naturally, I swallowed it all.

After that, I cleaned him up a little more with my lips and tongue and we parted ways.

I never did ask or find out, if he or his friends had been following the bulletin board on the web site, and knew I might have been there. It doesn't matter. I felt I had moved a step closer to getting attention from men, and resolved to continue trying for the ultimate.