Singapore Ladyboy

A few years ago, I happened to be in Singapore for a conference. I didn't know the place and the taxi drivers are talkative and informative. I asked one to take me somewhere the girls were friendly and the beer was cold. I ended up getting dropped off at a place on Orchard Road, the Towers, it was called. I was soon to find out it was four floors of massage parlours and bars.

As soon as I walked in the first one, it was full on, girls asking me to buy them a drink. To say they were fully clothed would have been a stretch. I declined the offer of companionship as the night was young and I was wanting to just chill in the corner, enjoy some cold beers and watch the ebb and flow of the patrons and the girls that worked there. I did buy a few girls a drink, and they were expensive, 3 times the cost of my Tiger beer. Turns out, they get a percentage of every drink they get someone to buy them, quite a racket.

After checking out three or four bars and having a few beer in each one, I thought I am only on the first floor, I should travel upward and see what's on the next two. Maybe something more exotic, maybe more of the same. Turns out it was both. A dance floor on one level occupied a good portion of the second floor and there was girls standing outside bars, trying to lure you in with calls like, "2 for 1 beers". There was bars with Russian girls, Vietnamese girls, girls from the Philippines, whatever kind of girls you wanted to buy a drink, you could probably find somewhere on one of those floors.

As I approached the top floor on a wide set of stairs, there happened to be a girl coming towards dressed to kill. Short girl with a short skirt and decent sized tits for her small frame. I said a good evening and flashed a smile, thinking, "that girl is way out of my league" and was about to carry on up the stairs when she stopped me.

"Where you headed to?" not a greeting or asking my name or anything, just, "where ya to?" I was almost at the top of the stairs and pointed to the first bar at the top of the stairs.

"I'm off to check this place out" I told her. She smiled back and stood with a provocative posed, turned sideways on the stairs, one leg on the next stair down, "that place is nice, if it's what you are looking for and that's the kind of thing you like, but I could show you a bar around the corner where the drinks aren't as expensive and the only girl looking for your attention will be me.

Well, I was halfway back to her and telling her, "Lead the way", I would have to check out the top floor of that place another time.

We ended up at a small sports bar, quiet and sitting at the bar, stools were close together and I am 6 ft tall. She was short to me, but over 5 feet. From the time we sat down until the time we left, our hips were touching and it was distracting as hell. Sasha was her name and she told me about how she worked in an office nearby as an assistant and was originally from Malaysia.

While we talked about our backgrounds and what had brought us to Singapore, she would laugh at a small joke I had made and put her hand on top of my mine every time. It seemed she always had to be touching me and it was driving me crazy. I hadn't really gone looking to take a girl home that night, but I found myself thinking, "Could I be this lucky?"

Around midnight, Sasha asked me if I had to be at any meetings the next day. I figured, OK, this is when we make a date to meet for lunch, I was disappointed as I was hoping maybe I could convince her to come back to my hotel to continue this touching that she always seemed to be wanting. I told her I was free tomorrow but the following day I had a full day. She had a bit of a pensive look on her face and came out with something I wasn't expecting. "I'd like to spend the night with you, if you want, but I need to make sure you know something before we leave here." At this point, I was not quite sure what was coming, is she married, some big Singaporean is going to want to kick my ass? She put her hand on my inner thigh and at this point I was getting so hard I was thinking whatever it is, we'll deal with it tomorrow. She started stroking my cock through my pants right there at the bar and I told her, "c'mon, lets get out of here."

"Before we do" she said, "I need to make sure you know I am trans". I sure wasn't expecting that, but I was so hard at that point and she was still slowly rubbing my cock, I didn't care. I had never been with a trans girl before and I was thinking, to hell with it, it's not like I haven't thought about it. So, I paid for the drinks and we went to a taxi stand nearby.

Now that we both had committed to her coming over to my hotel she was more touchy than ever. Held my crotch of my elbow as we walked and held my hand when we finally got to the hotel. Once we got to the elevator and the doors closed, I was getting a bit nervous, thinking, this is actually happening. This little girl, a foot shorter than me pushed me up against the wall, grabbed the back of my neck and pulled me down to her. She gave me a passionate kiss that probably lasted a good 10 seconds as the elevator ascended. As she kissed me, she put her hand on my cock that was quickly getting hard and gave it a squeeze.

By the time we had made our way to my room and got the door open, we were all over each other and when I grabbed her tits, they were firm, yet soft where it counted. I can't even begin to describe it and her nipples were rock hard and sticking out ready for my mouth. She sat on the bad, or I sat her on the bed and I slowly opened her blouse while kissing her neck. Her skin was so smooth, I worked my way down and before I knew it she was giving small gasps as I rolled her nipple around with my tongue.

I felt her wiggling beneath me, and realised she was kicking off her skirt and panties. She had her hands on the back of my head running her hands through my hair as I kissed first one nipple, and then the other. I kissed her belly and repositioned my self to go down on her and right in front of my face was a rock hard cock. Easily 7 inches and fairly thick, thicker than mine. I was in such a state, so horny and wanting to please, I never even skipped a beat.

My girlfriend back home and I had tried pegging and it had gotten to the point she was fucking me more than I was fucking her, so I wasn't adverse to being fucked but I had never sucked a cock before.

The precum was oozing out of her cock and I tasted it with my tongue. Now, any guy that says he has never tasted cum is lying. We have all done it, even if its just to see what the fuss was all about. I had a girlfriend a few years ago that would rub my precum on her nipples and ask me to suck them. I got to like it, as they were slippery. I would even take precum from my cock and rub it on her lips before kissing her passionately, but I digress.

I have had blowjobs by girls that weren't proficient at it so I tried my very best to ensure my teeth never touched her cock, and I opened my mouth wide, and before I knew it, I had most of her cock in my mouth and I was bobbing up and down with abandon. She still had a hand on the back of my head and was encouraging me with words like, "oh baby, you are so good at that" and "omigod, please don't stop". If you would have told me I would be sucking the cock of a beautiful Asian girl before that day, I would have laughed in your face but after the connection we made, it just seemed natural to go with it.

I had been sucking her cock for a good five minutes and my jaw was starting to ache when she started to tense up. She told me, "OK, stop, or I will cum". She was still bucking her hips into me as I bobbed up and down so I knew she really didn't want me to stop. Her hand was still on the back of my head applying pressure as I went down each time.

"OK, really baby, stop or you're going to get a mouth full of cum", her sentence was broke up into three or four parts as she gasped each time I went down, getting ready to orgasm.

I never even thought about stopping, the only thing I wanted right then was to feel her rock hard cock shoot her load into my mouth, like I was about to accomplish a mission I had set out to do since first putting her inside my mouth.

I had one hand on her ass and with the other I started stroking her cock, taking my first finger and thumb and wrapping it around like an OK sign and stroking as I bobbed up and down. This was probably the most erotic thing I had ever done, I could feel the precum oozing out of my own cock, even as I tasted hers as it flowed into my mouth. My own cock was so hard it was almost painful.

She tensed, held my head tight and exploded into my mouth, hot cum in spurt after spurt. She groaned aloud as she pumped load after load into my mouth. I had never given anyone a blowjob in my life, let alone swallowed somebody's cum but I was still going up and down, milking it for all it was worth. Cum ran out of the sides of my mouth and onto her shaved balls. Having that post orgasm sensitivity, she finally pushed me off and giggled at me, cum running down my chin.

"That was so good" she said, "you must do that a lot". I told her that was the first time I had ever sucked someone off and she laughed at me and didn't believe me. I told her, "honest, not even kidding."

"You have never been with ladyboy?" she said. "You were headed into the Crazy Horse at the top of the stairs and that's where all the ladyboys hangout so I assumed you were looking for just what you got" I started laughing, "I had no idea what bar was on the fourth floor and I certainly never knew you were sporting a cock bigger than mine when we first met." I still had a raging hard on and when I mentioned my cock, she seemed to realize I was still waiting for mine.

"If you've never sucked a cock before, have you ever fucked a girl in the ass?" Before I could even answer, she was pushing me on the back and quickly grabbed some lube from her purse. She stroked my cock like I had hers with it and precum oozed out, mixing with the lube. She straddled me, facing me and positioned her ass to my cock. Reaching behind her, she guided my cock to her ass and slowly eased herself down onto me. Her ass was so tight and warm, and the sight of her sitting on me, facing me and her cock hanging there, her beautiful tits, again I found myself thinking, who would have ever seen this coming?

Once she had slowly impaled herself on me a few dozen times, she leaned over and kissed me, tasting her own cum on my lips and then whispered in my ear, "hold on baby". She put her hands on my shoulders and started riding me hard and fast. My cock was slamming into her and I was doing very little work as she was in complete control. I could feel her squeezing my cock as she went down and then releasing as she travelled upwards. The sight of her tits and her cock bouncing off my pubic area as she rode me hard with her eyes closed, I knew I wouldn't last long. Her cock was semi-erect and as I watched it bounce up and down, it was getting harder and harder, more erect as time passed.

I told her I was going to cum and she showed no sign of slowing, if anything, she picked up the pace. I took this as permission to cum in her ass and I exploded inside her. I don't think I had ever had such an intense orgasm. She slowed yet still seemed to be milking the cum from my cock with her ass as I sent wave after wave into her. I laid there in shock after just in awe of what had taken place from the moment we got to the hotel to now, my cock going soft in her ass and the taste of her cum still in my mouth.

I could see that me coming in her ass had made her rock hard again, and she got off me and rolled me over. "You're not done yet baby" she said. Any time she called me baby, made me putty in her hands. I had never been fucked in the ass before by a real cock but I knew what I was in for when she started lubing up my ass. In for a penny, in for a pound, as the saying goes. I knew how good it felt to be pegged by my girlfriend and her 7" strapon so I wasn't apprehensive at all. By this time, all caution had been thrown to the wind anyways. I felt the head of her cock putting gradual pressure on my ass and then in she went. It hurt for a bit but after some encouragement from her and me relaxing I finally felt her pelvis area touching my ass cheeks and knew her whole cock was inside me. I felt so full. she just stopped and let my ass relax and accept it and without even thinking about it, my body seemed to have a will of it's own, I started moving up and down on the bed. She felt me begin to move and with a chuckle said, "oh, you are ready, are you?" and she reached and put a pillow under my hips so my ass was up in the air a bit. She shuffled me over to the edge of the bed, her cock almost came out but didn't and she planted her feet on the floor.

Grabbing my hips, she knew what I wanted and started slowly fucking me. I couldn't believe how great it felt and why had I never done this before? A strapon felt great but this was a whole new level. I told her to fuck me faster and she refused, keeping a steady pace, sliding her cock all the way in and then almost all the way out, to the point I thought she was going to quit but then she would plunge back in, teasing me.

Finally, when I thought I could take it no longer and was begging for her to go harder, faster, she took pity on me and started slamming into me hard and fast. My cock was rubbing on the pillow below and I knew I was going to come soon and told her so. She had been fucking my ass for what felt like forever and I didn't want it to ever end. I started squeezing my ass cheeks together like she had done to me, and I dimly wondered who was going to come first. I figured I would, because I knew I was close when all of a sudden I felt her cock throbbing, emptying load after load of come inside my ass. That was it, put me over the edge and I came all over the bed beneath me, the come getting all over my pubic area and soaking the bed.

Sasha seemed to come out of a daze and kissed the back of my neck while she still pushed her semi hard cock in and out of me. She laid down on my back and I felt her cock shrinking as she went soft and I felt a sense of loss so profound. I had just came twice and all I wanted was her cock back inside me. We had both had a couple of orgasms but after a short interlude of cuddling and playing with each others cock, Sasha asked me how long it would be until I was ready for round two. "Don't you mean Round three?" I asked her. "There is no way in hell that is your first time taking a cock" she said, "you were like a pro" I laughed a bit and told her it sure was, but I had experience with pegging. I told her the difference between being pegged and what we had just done together was quite a bit, no comparison whatsoever.

I lost track of how many times I had her cock in my mouth, from the shower to the bedroom and back again, how many times we fucked each other that night. I just did what I asked and let her lead, she had done a good job so far and I wasn't disappointed.

I slowly came to around noon, remembering we had fucked off and on until dawn and found Sasha cuddled up to my back, spooning me. I reached back and gave her cock a slight caress and heard her mumble, "seriously?"