Thanks for the support to capcrunch and dickrick.
Let me recall my first time i actually dressed up and met someone. Some details might be lost as it's been really a long time ago that this incident happened. Nonetheless, enjoy! 
Back in the days, probably about 8 years back before I entered NS. IRC was a pretty common program to use for chatting and making new friends. I remembered I went on IRC and proceeded to go this channel called #ladyboys using the alias
Sheryl-XD to chat up people.
One day, I was chatting pretty late in to the night with one chatter and it was a really hot and raunchy chat. We were chatting about sex with me obviously being a girl and it was getting me excited. Just as i was about to go offline as it was already 7am, he asked me if I wanted to come over his house and dress up and have some fun now. I was kind of dumbfounded as I didn't know whether I wanted to or not. Scared as I was, it was kind of exciting. Before I knew what had hit me, I already had said yes and was packing up my clothes to head over to his place.
We had exchanged number so he dropped me a SMS with his address and I took a cab over to his place. Many thoughts flashed across my mind, "What am I doing?, Am I gay doing this?, What are we gonna be doing?" Feeling nervous and my hands feeling cold, I was already at his door steps and was reaching out to press the door bell. A few seconds later, a guy opened up the door and was inviting me to come in. As you see, I am not dressed up when I showed up at his place. We sat down and chatted about non-sexual chat and asked about personal question. You see, he was a married man without any children and was about 30+ years old and at that time I was about 20 years old only.
After awhile, he asked whether I would like to get dressed or not. So I was off to the toilet to change and as a token, he gave me a new pair of his wife's black thigh high stockings to wear with the garter belt i brought along. I dressed up myself in a smooth black bra and a lacy black panties. Used some nubras stacked on one another to create my small little "perky" breast. Slipped on my garter belt and attach them to the black stockings I had received and was wearing a black mini skirt and a black spaghetti top. Everything is basic black! Oh and not forgetting my long black hair wig. I stepped out the toilet and headed back into the living room where he was waiting for me. When he saw me he said:
"You look good and sexy." I gave a slight smile and in my highest pitched voice i said:
"Thanks".
We chatted for awhile before we proceeded to the bedroom and I was lying in bed next to him while we were watching a porno flick to get ourselves in the mood. Next thing was that he was rubbing my shoulder with one hand across and the other was groping my tits through my top. Instinctively (I watch a lot of porn) as a girl, i started rubbing his cock through his shorts and could feel it getting hard and harder. I pulled his pants down and threw them on the floor, my hands were now stroking his cock up and down. As I was working on his cock with my hand and watching porn at the same time, i felt damn horny. I felt like I was like one of the pornstar in the porn clip that we were watching. I went down slowly on him and started licking his inner thighs and moved towards his balls and started licking and sucking on them. I recalled how pornstars sucked cock and of course I had girlfriends before who gave me BJs. I re-enacted how they would do it and was sucking on his cock not before long. I opened my mouth as wide as I could and finally closed my lips around his cock. I let my lips run along the full length of his dick while I sucked in. Then I licked his balls and licked the entire length of his dick. I pulled back the excess skin and licked his entire head. Then my mouth went back down on his cock again, I could feel it starting to gag me so I slowed down and went down farther and farther until I had almost his entire cock in my mouth. After awhile of gentle sucking, he stood up, got out of bed and asked me to get on my knees on the floor. So I got off the bed, knelt infront of him and started to suck on his cock but this time I sucked on it faster and more furiously. I stroked the base of his cock while I went down on it again, being careful not to touch his cock with my teeth, I started going up and down on his cock with my mouth, tongue and lips while also stroking the base. Faster and faster I went, and he was pumping his ass up in the air to fuck my mouth. He pushed the back of my head down on his cock and I took his full length in my mouth. I sucked his cock for close to 10 mins and my mouth was feeling very sore. So I stroked his cock faster and harder while sucking to make him cum. After 5 more mins of stroking and sucking, he said:
"Oh I am going to cum, you want me to cum in your mouth?" As I was not prepared to taste cum yet so I replied:
"Don't cum in my mouth, cum on my face." The next 3 - 4 strokes, he took his cock out from my mouth and started to jerk his cock infront of my face. I closed my mouth (in case some cum accidentally flew into my mouth) and closed my eyes. After awhile, I felt his first spurt of cum hit my face on my cheeks. He didn't cum quite a lot, but a reasonable amount. At this point of time, I had my first FACIAL! The next thing I did was running to the bedroom toilet and washing it off. He was nice enough to give me facial foam to wash my face with and a towel to dry off.
I walked back into the room, still dressed and sat on the end of the bed and chatted with him for 15 more mins at the same time continuing to finish watching the porn clip before I decided to go home. I changed out of my sexy attire into my guy clothes and left his house. He left his house together with me and showed me the way to the bus stop which we took together as we head to town, Orchard Road. Once we reached Orchard, we parted ways as I made my way back home.
Once I reached home, i unpacked my clothes, crossdressing items and stored them away in my secret hiding spot in my room. Awaiting in anticipation of the next adventure I might have. This was just a beginning of what I had opened myself up to.
