One Night in Bangkok

I swallowed nervously as I stared down the door of the coffee shop. I was in Bangkok for the summer. I had been having a good time, but had actually been fairly G rated. Tonight though? Tonight, I was ready to get laid.

I had been chatting in various online chatrooms the last few days. Today, I met a lady who I hit it off with right away. She was up front that she was transsexual, which was fine with me. I had never had any kind of sexual contact with anyone with a penis before, but to be honest, I had thought about it, and I was excited to try. I was 20 and she was 40, which made me more nervous. Based on her pictures she easily could have been a model, so fuck it. Age is just a number, right?

We had been chatting all day, and we just hit it off. It's hard to describe what clicked so nicely between us, but the conversation just flowed, and I think we both felt it. We both got off at 5, so she invited me to a coffee shop downtown near her office at 6. My summer internship was near my apartment, so I had time to stop by and change into a clean pair of slacks and a nice button up shirt.

I was excited right up until I started walking down the stairs to the subway. As I started walking down through the crowd, my nerves started to settle in. The fuck was I thinking? I'm straight. What if her pictures aren't real? What if I'm about to meet up with some dude in half-assed makeup who knew how to work photoshop? And meeting in public? Everyone will know I'm on a date with a transsexual. A transsexual twice my age. I can't do this.

I rode the subway downtown, knowing the whole way that I wasn't going to end up at the coffee shop. At every single stop, I warred with myself about whether to get off and get on a train headed back to my place. But I wasn't that kind of guy. I had made a date with her, and the least I could do was call her and let her know I wouldn't be making it. I didn't get cell phone reception in the subway, so I might as well head downtown, call when I got reception, then find dinner somewhere downtown.

I hadn't actually talked to her on the phone yet. All of our conversations had been by text in the chatroom, then by email when we sent each other a few pictures. She gave me her number in case I got lost on the way to the coffee shop. So it was a surprise when I called her and a woman with a very sexy voice answered. She was an alto, not a soprano, but definitely not a man pretending to be a woman. She had a bit of a Thai accent, but her English was very clear with maybe a bit of a British accent to it.

We chatted for a few seconds just as easily as we had been chatting all day in the chatroom. She mentioned how excited she was to meet me, and I started to feel conflicted all over again. This was the moment of truth. I nutted up aaaannnddd..... told her something had come up at work and we would have to reschedule. She was disappointed, but actually totally ok with it. She worked a busy job, and she understood things come up. As we chatted some more about rescheduling I was feeling worse and worse about lying to her and more and more like I was missing out by not taking the opportunity to meet with her. Finally, I confessed. I admitted that I wasn't busy, I was just really nervous because I had never been with a lady like her before. She didn't hesitate at all as she told me she completely understood. She had just gotten out of a long relationship, and she was really nervous about meeting anyone too. Then she said those stereotypical words that appear in every one of these first timer stories: "it's just a cup of coffee. Why don't we talk some more in person, and if either of us isn't comfortable, neither of us has to do more than drink some coffee."

She made it sound so reasonable. How could I say no? If it ends up not working out in the pants department, I could already tell that she'd be a great friend. So I walked the block and a half to her coffee shop. It was on the second floor. I walked up the stairs, stared at the door as I swallowed nervously, and there she was.

I recognized her from her pictures, but she was a terrible photographer. Her pictures didn't do her justice at all. She was a fucking knockout, and I couldn't believe that I was here to see if we might want to get naked and sweaty together. She was wearing a black and white, sleeveless dress with a kind of floral pattern on it. Above the knee, just short enough that I could see her incredible legs. But also long enough that if I saw her in an office environment, I wouldn't have done a double take thinking there was anything in appropriate about it. From her exposed arms and calves, she clearly worked out. Not bulging muscles, just nicely toned. My prior concerns about being embarassed to be seen with her in public were completely unfounded. I was proud to have this model looking, clearly powerful business woman smiling enthusiastically as she greeted me and pulled me right in for a hug. She told me she was 5'6, so she must have been wearing 4 or 5 inch heels because she was just slightly shorter than my 6 feet.

She walked me over to the counter, ordered a fancy espresso drink, then asked me what I wanted. I ordered, then pulled out my wallet to pay. She quickly knocked my hand away as she pulled some cash out of her designer purse. "You're a student. I'm not. My treat."

We got our drinks, and she steered me to a table by the front windows. The conversation flowed just as smoothly as it had online and on the phone. It felt like we were old friends. She was an executive who handled imports and exports. She had recently broken up with her boyfriend of many years because he cheated on her. I clarified that I wasn't looking for anything serious, and she looked at me like I was stupid before laughing and reminding me that she knew I was only in town for a few more weeks. After a while, all my nerves were gone. Forget being nervous about being with a transsexual. At this point, I wasn't even convinced she was a transsexual. We had only exchanged clothed pictures, and she was way too gorgeous to have ever been anything but a woman. I was mostly curious why this gorgeous executive was hanging out in a coffee shop with a 20 year old college student. Though I wasn't dumb enough to actually ask her that question.

I'm not sure how long we sat there talking. I could have been 20 minutes, it could have been 2 hours. We hadn't actually had any physical contact other than the initial hug and maybe her ocaisonally putting her hand on my arm. But finally, I felt her hand on my knee as she looked me in the eye and just asked "are you ready to see my place?"

All the nerves came flooding back. She was great to hang out with, but I really wasn't sure I wanted to know what was under that dress. I stammered nervously about some bullshit, ending in we hadn't even kissed yet. She didn't even let me finish the sentence before she leaned in and planted a kiss on me.

"So, we've kissed. Are you ready to see my place?"

I was stammering again like a fool. "I, ummm... wow. I wasn't sure about going home with someone I didn't like kissing, but that wa-" I have no idea what the rest of my sentence was going to be because her lips were back on mine. This time for more than a quick kiss. We were making out like teenagers right there in the coffeeshop. Her hands on my face, my hands on her elbows, her tongue way, way in my mouth. This is going to sound gross, but her coffee breath was intoxicating as she completely took control of the situation.

Before I knew it, we were in her SUV as she drove us to her place. My hand was on her thigh, confirming that it felt as toned, smooth, and incredible as it looked. We made out at every red light, and my hand inched up her thigh under her dress every time we kissed. I could feel the heat coming from her crotch, but I was too afraid to actually touch her there. I still wasn't quite convinced this gorgeous woman was actually a transsexual, but I was also too afraid to find out either way. So I inched my hand higher and higher up her thigh as she kept breathing harder and harder and as she got more aggressive about launching her lips onto mine at every red light.

Finally, she pulled into a parking garage. We got out and walked over to the elevator, where she promptly grabbed me by the collar and pulled me in for more kissing. There was no coffee shop table or car gear shift between us, and she pulled us firmly together so it felt like every millimeter of our fronts were touching. Of course, that only lasted for about a second because I finally knew. I had been rock hard since somewhere during the car ride, and as she pulled us together and our crotches met, it became apparent that she was rock hard too. I gasped and stumbled back, completely surprised. I don't know what stupid look I had on my face as I gaped at the tent in the front of her dress, but I must have looked funny because she just laughed before grabbing me by the collar and pulling us back together.

All concerns about being with someone with a penis were gone as we made out in that elevator. Her hands on my chest, my hands on her hips, our cocks grinding together through our clothes. She was wiggling her hips about, laughing in delight every time she knocked our cocks together and my hips instinctively shot back.

Then we were at her floor, and I swear she skipped out of the elevator. I followed quickly behind, my eyes glued on the hemline swishing around her thighs. She let us in, then directed me to sit on the couch. After the car ride and the elevator trip, I was ready to go. But my confident, sexy executive suddenly disappeared. She had kicked off her shoes the moment we walked in the door. And now she sort of stood there awkwardly in front of me, barefoot with a tent in her dress, asking me if I'd like something to drink.

I didn't even answer about the drink. I just leaned forward and pulled her down onto me. She straddled me, back to making out as our cocks rubbed together. I had both hands on her ass, marveling at how great it felt through her dress. Then she was kissing down my neck and unbuttoning my shirt.

The hell with that, I wanted to see her naked too. I tried pushing her dress up, and she stood up and pulled it over her head. She stood there with her incredible legs, her six pack, and her cock tenting out her red thong. I was surprised. She felt huge when she was teasing me in the elevator, but she was clearly not very big now that she was mostly out of clothes. As she straddled me to start kissing again, my hands instinctively went to her breasts. I tried to rub the front of her tan bra before realizing that she had no breasts. She was wearing an empty padded bra that puffed to about a B-cup. I tried to move my hands back to her ass, but she was already sliding to her knees and undoing my pants.

I didn't have time to think before I was in her mouth. It felt amazing as she took me deep into her throat and moaned around me. I'm not small, but she apparently had no gag reflex. The professional looking executive disappeared with her dress, but I was an even bigger fan of this slut that replaced the executive.

She sucked me like she'd been dying of thirst and the only available water was in my cock. Moaning the whole time, making this incredible vibrating feeling around my cock. I let her go for a few minutes, but I wanted more.

I put my hands in her armpits and pulled her up so I could lean down and kiss her some more. She actually made a loud disappointed noise when my cock left her mouth, but she quickly refocused to finishing taking off my shirt as we kissed. I reached behind her and unhooked her bra, then pulled her the rest of the way to her feet. She shrugged out of her bra as she stood, and I was a little surprised that she had no breasts of any kind. Not small... nonexistent. Oddly, my gorgeous date having no breasts under her dress made my brain freeze more than her having a cock had. But her body was still spectacular, and I was 100% in at this point. All nerves were gone, and I wanted a turn making her feel good too.

As she stood up, I hooked my thumbs into the sides of her thong and slid it to the floor. Her hands shot in front of her crotch and blocked my view the moment her underwear dropped. I was still sitting on her couch while she stood in front of me, so I had a great view of the backs of her hands. I kissed under her belly button and down her flat stomach to the top of her bush. Loving the feel of her fur tickling my lips as I kissed her. Her hands were locked in place though. She tried to turn away, telling me it was time to go to the bedroom, but my hands were on her hips and I didn't let her twist away.

I told her I wanted to see everything before we went any further. She hesitated, visibly nervous, and I had a second to think about how I was going to make her comfortable enough for her slut side to come back again. Worrying that I had ruined things by pushing too hard. I didn't have to do anything though as after just a moment's hesitation, she moved her hands to the top of my head. And there she stood in all her glory. Her cock had felt huge earlier, but looking at it, it was tiny. Maybe 3 inches, but rock hard and drooling. A drop started oozing toward the floor, and I couldn't let that go to waste. I quickly leaned forward and took all of her into my mouth. I don't know what I was expecting, but it surprised me how not weird it felt. I didn't feel like I had a penis in my mouth. More like I was sucking her little finger. Though of course it tasted a lot stronger than a finger would have as I swallowed her precum. She was so small that I there was nothing to do but slide my lips to the base. While her penis felt surprisingly normal to have in my mouth, it was absolutely intoxicating to rub my lips and nose in her bush as I sucked on her.

I had probably less than ten seconds to suck on her before she pulled back, grabbed my hand, and pulled me to my feet. The rest of my clothes disappeared as she pulled me to her bedroom. I loved watching her naked ass bounce in front of me before she reached the bed, turned around and fell backwards onto the covers. I crawled between her legs and moved up to kiss her, but she put her hands on my head and with a mischievous grin pushed my face back into her crotch. I went back to blowing her. Still perplexed by how not weird her cock felt in my mouth, but loving hearing her moan and feeling her writhe beneath me as I bobbed up and down on her tiny shaft.

I could feel her body tensing up when she suddenly pulled me up to her face and started kissing me again. She had a huge smile as she told me she didn't want to cum yet. Then she rolled over and told me to lay down. She fished in her nightstand drawer for a moment; facing the other way doing something I couldn't see. Then she turned back and planted a kiss on me. Her hands were behind her back, and it looked like she was fingering herself.

After a moment of this, she swung a leg over my head. She straddled my face as I looked up at her equipment hanging over me. I leaned up a little, getting both of her balls into my mouth. She giggled, leaned forward, and started sucking on me. When she leaned forward, I could see how wet her ass was, with a thick trail of what I guessed was lube running down the back of her balls. I tried to lean forward to get her cock into my mouth again, but she pulled off my cock just long enough to tell me to finger her.

Duh. It finally clicked in what I was supposed to do. I reached up and spread her ass wide, admiring the view. I was vaguely aware of her continuing to do wonderful things with her mouth on my cock, but to be honest I was completely focused on her ass at this point. I had fucked women before, but I had never had anal sex with anyone. I tentatively rubbed a finger around her anus, nervous about if I would encounter anything in there. But her moan as I began to rub her quickly did away with any concern I had. I gathered a large drop of lube off the back of her balls and pushed it up her taint, then slid my finger into her. Her moans on my cock felt incredible as I added a second finger to her rectum.

I kept kissing her inner thighs as I fingered her. Loving tasting her sweat. Loving feeling her get more and more worked up as I kept pushing my two fingers in and out of her. I probably should have used my free hand to stroke her a bit, but I was too entranced watching my fingers disappear in and out of her body.

I felt the bed shift again as she moved above me. She didn't ask me to change anything, so I just kept fingering her as she twisted back around to her nightstand, then leaned back into our 69. I had mostly been ignoring what she was doing to my cock, too focused on her ass. But I recognized the feeling as she rolled a condom onto me. Then began stroking my cock with what felt like a very well lubricated hand.

I was just along for the ride at this point as she directed the action. When she felt that her ass and my cock were sufficiently ready, she didn't say a word or ask my opinion on the matter. She just swung her leg back over my face, then turned around and swung her leg over my stomach. Straddling my stomach, staring me down with a sultry smile and huge horny eyes. She scooted back slightly, grabbed my cock, and lowered herself onto me. I was expecting some sort of drama when I popped into her ass. I've never had a cock in my ass, but I'd always imagined that that moment of penetration must feel intense. Well, apparently I imagined wrong as she just slid right down me without the slightest sign of discomfort. She threw her head back, and moaned at the ceiling as she began to ride me looking for all the world like any woman I've ever had ride me. Other than her stiff little cock bouncing up and down between her legs, drooling all over my stomach, of course.

She looked amazing riding on top of me. Her head was thrown back as she moaned loudly at the ceiling. Her completely flat chest still gave me a bit of cognitive dissonance. I was soon distracted by the sweat beading up across her chest, then making an amazing trail down her perfectly flat stomach and into her belly button. And of course, her muscular but perfectly smooth thighs felt divine under my hands as I held on, enjoying the ride.

Without much warning, she leaned forward and her lips were back on mine. I had just a moment to process the lovely kiss before she was climbing off of me. She looked like she was about to roll onto her back, but I decided to take charge. I grabbed onto her left shoulder and held her facing down as I slid out from underneath her and shifted behind her. She made another move to roll over, but I wasn't having it this time. I put a little more weight into my hand on my shoulder, and she took the hint, sliding her face and chest down to the bed, her ass still high in the air.

Her naked ass looked divine, and I leaned down to kiss a cheek as I got behind her. She let out a huge moan as my lips made contact. I was surprised by how enthusiastically she responded to a kiss on her ass, but I kept kissing, loving the amazing sounds that made her emit. It took a moment for it to click that no one would moan like that just from some lips on the cheek. She thought I was about to eat her ass. I had had my face in her ass earlier when we were 69ing, but for whatever reason, this was different. I hesitated, very much wanting to pleasure her, but unable to slide my mouth over the 2 inches from her kissing her cheek to kissing her anus. Instead, I got up on my knees, my left hand gripping her left hip, my right hand planted firmly in the middle of her back, my cock lined up perfectly to slide back into her. I admired her incredible ass for half a second more; watching her anus spasm and a bit of lube sliding back out of her. Then I slid smoothly into her, listening to her moan as I fucked her from behind.