I, TEIRESIUS Alaric Leong, Singapore

‘Yes, they’re real.’ A pause. ‘One hundred percent real.’

Talk about being jolted; I felt like a school kid who’d just been caught doing something naughty in class. I mean, that clarification came from out of nowhere. We had been talking about the advertising industry when suddenly my companion there at the bar had thrown that at me.

‘Uhh… excuse me. I didn’t mean to—’ No, I didn’t mean to, but the worst thing was that the moment I was accused of it, my eyes automatically slipped down to peer at the things I’d been just sneaking peeks at until then.

She put her hand under my chin and lifted it just a little, to face level.

‘My eyes. The colour? This is the real colour of my eyes, this hazel brown. One of my great grandparents was European, from Bohemia or somewhere. I evidently inherited that gene from him.’

‘I see. Yes, your eyes. I was… wondering about that colour. I mean, these days, with all the things you can do, shaded lenses and all.’

‘Believe me, I don’t have any lenses. I don’t need them.’

‘That’s good to know.’

Then came that sly smile. ‘The other things, they’re also real. The things you were just sneaking repeated looks at.’


‘Excuse me, I didn’t—’

‘Haven’t we been here before? Anyway, to put your doubts to rest: these tits are mine, too.’

‘Of course. Who else’s would they be?’

And then he… she… this strange person sitting opposite me threw his, her head back and gave this husky, deep-throated laugh. Which only deepened my suspicions. Whatever the current status of this woman, I was pretty sure she did not start out life as a female. There were all sorts of clues; that manly laugh was just one of many.

‘By the way, what’s your full name, Mr Advertising Accounts Executive?’

‘Oh, that’s right, I didn’t… Raymond Chua.’

‘Raymond. Nice name. I’ve always liked that name. I’ve often thought that if I have maybe six sons, one of them will definitely be called Raymond.’

‘Yeah? Well, like they say, everybody loves Raymond. And your name is…?’

‘Teresa. That’s good enough for now. A simple Teresa.’

‘But not so simple a person, I think.’

Teresa then crossed her very shapely legs and smiled. ‘I court complexities. Simple is, for me, just a synonym for “boring”.’

‘I see.’

‘I hope you don’t see! If you did, I wouldn’t be complex enough.’

‘Okay. Uhh… can I buy you another drink?’

Teresa nodded. ‘I think so. But only if I can buy you a drink in the next round after this one.’

‘I wouldn’t say “no”.’ And I didn’t.

And so it went for four more rounds, each of us alternating on buying the next round. Her drink was white wine, mine was red. And after that fifth round for both of us, in vino veritas had taken command of the conversation.

It also produced a certain level of physical comfort. Teresa had already slipped her hand over mine a couple of rounds back, and had now moved it up under my shirt sleeve, lightly stroking the hair on my forearm.

‘So… do you like me, Raymond?’

‘I think I do.’

He.. she laughed. ‘Why are guys always like that? I wasn’t asking who you think is going to win the World Cup. I asked you about your feelings, what you feel. You’re not sure what you feel?’

‘Well, I… what I feel is complex. It’s… I don’t know how to explain.’

‘Okay, Raymond, I do like you. Like you quite a bit. Like you enough to let you ask me.’

‘Ask you what?’

‘Ask me the question you’ve been wanting to ask since you first saw me earlier this evening, across the room, when you liked what you saw and then wondered what might be wrong with you for liking it.’ There was then a tense pause. ‘My sexuality. You’re not curious?’

‘Sure I am.’ I took a deep breath. ‘Okay: Teresa, are you really a man?’

Teresa looked me right in the eyes. ‘Not anymore.’ Bang. Like being hit over the head.

She then inched her left hand over and pulled her plunging neckline down a couple of plunges. ‘Like I said, these breasts are real. I had to undergo treatment to grow them, but they are real, they are all Teresa. And Teresa, nee David, is now a woman.’

‘Do you… Uhhm, what’s the state of your plumbing?’

‘Complex. But the main thing is, I don’t have a penis. I lost that.’


‘Are you a…’

‘Full woman down there? Well, I have a vagina. A functioning vagina.’

She then drew a long, sad breath. ‘And with that, I think I’ve just signalled an end to our pleasant conversation this evening. I think I have told you more than I should have told you.’ She took her wine glass and rapidly drained the last third. She had the saddest look on her face.

For a moment, I didn’t know how to respond, so I just sat there, gazing at her like a fool. ‘And you don’t have to apologise, Raymond. Or make up some lame excuse. Just tell me that you enjoyed our little intimate chat, but you can’t go any further with a woman who grew up a man.’

She sat there, staring off into the corner with a defeated expression. A few moments later, she turned back, managed a loser’s smile, then blew me an air kiss, slid off the seat and turned away.

‘No, wait,’ I called out. ‘I’m not turned off by you. In fact, I’m… I find you even more enticing now that I know the truth.’ In vino veritas was in full force here.

‘Really?’

‘Really.’

I didn’t tell her, as I should have, that I had long nurtured this fantasy of being with a transsexual. The whole idea of being inside a woman who had once been a man was really a major turn-on. I wanted to know what it was like. In some ways, Teresa was playing right into the core of one of my kinkiest fantasies.

Our conversation then took a sharp turn to the more intimate and more friendly. We each had a half a glass more wine and then decided to take our little party for two to cosier surroundings. I was willing to take her back to my place, but was very glad when she suggested we go to her apartment instead. I was incredibly excited, more than I’d been in a long time. Hell, the moment we stepped out of the club, I was hailing a taxi I spied two streets away.

We held each other tightly in the cab and about halfway back to her place starting kissing rather passionately. I was hoping that the cabbie didn’t get a good look at her, but was willing to tell him to go to hell and mind his own business even if he did. I had taken this big step and wasn’t going to turn around now.

Back at her place, she offered me another drink, but I decided I didn’t need any more alcohol at that point, so just asked for a large glass of water.

While I was drinking, Teresa said she wanted to step into the other room for just a few minutes.

When she emerged again, she was wearing a kimono. ‘It’s genuine, from Kobe. An old boyfriend bought it for me.’

‘Oh, that was nice of the old boyfriend.’

‘And when I say old, I mean old; he had at least 25 years on me, this guy. But he was so sweet and so intelligent. He was a financial analyst, but we liked to discuss literature together. He was incredibly well-read. I really liked him.’

Back at the bar, Teresa had told me that she was a Lit major at university; NUS, in fact. I never cared all that much for literature, so I quickly steered the discussion off in another direction.

We ended up talking about the standard things, starting with where we grew up, where we went to school, all that duty conversation stuff. But with Teresa, it somehow came out relevant and even interesting.

At one point in our conversation, Teresa loosened the cord on her kimono and opened it slightly. ‘Do you know that for traditionalists, it is considered very crass to wear anything under the kimono. Anything at all.’

I suddenly realized how wildly aroused I had become. ‘I see. And are you a traditionalist? I wouldn’t have thought so.’

‘I am in some things. Very much so.’ She smiled this very warm smile.

It was almost unbearable. God, did I want to get close to her. ‘In other ways, I’m not at all traditional.’ Then that carefully poised smile again. ‘I told you I was complex.’

At this point, in the half-light of the room, I also realized how beautiful Teresa was—in a complex way. Sure, I was attracted to her from almost the moment I saw her, but this was a special kind of beauty which you only see after some time.

From her looks, and also from a few clues she had dropped into the conversation, I determined that in addition to that Bohemian ancestor, she also enjoyed a mixed pedigree of Chinese, Malay and probably even a bit of Indian. Maybe some of the other ASEAN members as well. And it all came together in a strange symphony of stunning features.

We continued kicking around various subjects for maybe another half hour. During this time, she fiddled with the opening of the kimono, occasionally edging it open slowly, then pulling it back together. Finally, at one point, as if it were the most natural thing in the world to do, Teresa pulled the flaps apart, threw her head back like she was posing for a fashion shoot and let the kimono slip off to her sides.

Her beautifully sculpted breasts were tastefully displayed. I couldn’t believe how perfect they looked, how… real. I punched myself mentally. Of course, they were real, she said they were real. Just a little… late in coming.

Even more interesting to me was that feature a bit south of the breasts.

The pussy looked somewhat strange, but pussies can look strange. It also looked real. One thing I noticed was that there wasn’t a lot of fuzz covering it.

It was almost as if she had shaved it and the hair hadn’t fully grown back yet.

I think she read my thoughts, because just as I was thinking about this interesting feature, Teresa deftly moved her hand down there and started stroking slowly. I couldn’t believe it. Until that moment, I was even wondering if I would get to realize my long-time fantasy that evening. Now it was clear: Teresa wanted me and, my god, did I want her.

After that we talked for another five minutes, though I cannot possibly remember what we talked about.

Suddenly, Teresa fixed me with those sexy, hazel eyes and jumped to the main topic. ‘I think I want to share myself with you. Do you want to share yourself with me?’ I’d never heard anyone describe sex that way, but it immediately seemed like the perfect approach to the subject. I nodded, as slowly and as ceremoniously as I could.

Within moments, Teresa had stood up, kimono still wide open, moved across the room and taken me by the hand. Without saying anything, just flashing a smile, she led me to another room. The door was closed, but I knew it wasn’t the kitchen.

Then, right before we reached the room, she turned and asked me the weirdest question of the evening. ‘Who’s your favourite character from Greek mythology?’

‘My favourite character…?’

‘Yes. Who do you really like? Or really identify with.’

Greek mythology? All I could think about was that bang-up movie with Eric Bana and Brad Pitt-Bull. I saw it three times, once on DVD when I was really drunk. ‘Umm… I guess Hector. Or Achilles. One of those two.

Depends on my mood really.’


She smiled. ‘Yes, they’re interesting too. Very manly.’ She then tossed her longish, full hair around vigorously, like a banner. ‘My favourite is Teiresias. Obviously.’

‘Oh yeah, of course. That’s what I would have guessed.’ I had no idea at that point who the fuck Teiresias was. But it didn’t really matter, because two seconds later, she took my head in her hands, pulled me towards her and started kissing me passionately.

Her tongue eased its way into my mouth, then started twisting slowly against my tongue. Then it started moving more intensely, desperately almost. It was as if there was something inside me, perhaps concealed, that Teresa needed to find, to recover and then take as much of that as she could before we broke our kiss.

As the kiss went on, I started feeling really strange. She slid her tongue out, grabbed the sides of my head—she was somewhat strong still—and looked me deep in the eyes.

‘Don’t resist. Just don’t resist it. Let your feelings come through and swirl you in any direction they’re moving. Be honest with your feelings.

Please.’ She then closed her eyes and we started kissing again. But even more intensely now. It was incredible.

She moved her hand down to the front of my pants and started rubbing.

I was already standing tall and proud, as hard as I could possibly be. She stroked me expertly with a skilful palm. I imagined that she must have been a great masturbator back when she was still a guy.

Abruptly, she broke the kiss, put her mouth against my throat and whispered. ‘Let’s go inside. I can’t wait any longer.’

‘I can’t wait any longer, too,’ I replied—which was pretty obvious at that point.


Without turning from me, Teresa reached back and opened the door.

She flipped on a low-glow light and stepped to the bed. The kimono slid to the floor. With her back still towards me, she raised her head and moved it gently. She also twisted her torso slightly as if to show off all the contours of her naked back and rump. She then arched one foot upwards to flaunt her shapely legs. I was pulling wildly at my clothes to get them off when she finally turned her head. ‘Hurry with that. You want some help? I can’t wait to feel you inside me.’

‘No, I can handle it. I’m almost there.’ I pulled my pants off roughly and tore off my underpants. She was now lying back on the bed, her left knee arched upwards, legs spread, eyes focused on the ceiling as if there was some message, some instructions there. Or some warning.

Finally naked, I climbed onto the bed, pulled myself against Teresa’s naked body and started kissing her. It was again that intense, deep penetration kiss. I had my right leg arched over her legs and she immediately started stroking it with her left hand. She then slowly ran her fingertips up the leg until she hit the fork in the road, applying just enough pressure with her nicely clipped nails to make it painfully sensuous.

I rolled back over slightly and started stroking her pussy, first with tightly drawn fingers, then with just two fingers stroking the gash. Then I slowly inserted the middle finger, making a circular motion as it moved deeper into her. She gave out a gasp. ‘Oh god; that’s so nice.’ I twirled a little more and then, strangely, she grabbed my wrist sharply and pulled my hand away.

‘I want to come with you inside me. Also, you shouldn’t do that too long or it will go dry. See, I have to use a lubricant. Natural wetness is the one thing the operation couldn’t provide.’

She then grabbed my sides gently and helped ease me onto her eager body. I suddenly spooked, like a young horse, and was afraid I might go soft.

The finger was one thing, but here I was about to enter a woman who’d spent most of her life as a man. That was still bothering me somewhere deep inside.

But I was very close already, so Teresa eased me down, then took my rigid penis, pulled it against the lip of her vagina and twirled it around on the hair and the wet entrance, then started pulling me into her.

After she had taken in the crown of my cock, I did the rest, with a slow, easy push all the way in. Then I suddenly said to myself, ‘This is it. You are inside a woman who nature had intended to be a man.’ What might happen in here??

At first the pussy felt funny, like something that didn’t belong there.

I wanted to pull out, apologise, wipe myself off, apologise again, dress as quickly as I could and run out of there. But I knew I wouldn’t. After a few strokes, I felt much more comfortable. And before long, it became very pleasurable. Teresa’s vagina was very tight and though not as deep as I would have liked, it fitted me nicely.

In fact, I thought I was about to come after less than a minute; that’s how good the pussy was. I closed my eyes and stiffened up my lower parts. Teresa slowed down her own stroking to a near halt. ‘You almost came, didn’t you?’

‘Yes, but—’

‘Don’t worry, darling; that often happens. Most of the guys I’ve known, they lose control quickly with my vagina. So let’s just relax, take it slow, and get used to the feel of the pussy.’

Which is exactly what I was trying to do. After another minute or so of soft thrust and pull, I felt more used to the sensation. Then we steadily picked up tempo and force, moving with an intensity I’d only known with a few women.


As we moved, Teresa started thrusting energetically. She suddenly called out, ‘I love it, I love it. Oh, I really love it. You feel so right. This is what I want; you.’

‘You’re what I want too. You feel so right.’ We were now going full throttle. Teresa’s pumping under me was, not surprisingly, unique. It was as if she was trying to regain some lost and essential part of herself in the act of sex. Though I was trying to constrain myself as much as I could, I came more quickly than was usual for me. As she was still going, I kept pumping as long as I could, but finally, I slumped against her, thoroughly exhausted. I was sucking in short, shallow breaths and the air in the room had this wonderful sour taste to it.

For the next I’m-not-sure-how-many minutes we lay there, holding each other, mumbling words. I asked her if she enjoyed it, what it was like, if she came. She answered ‘yes, definitely yes’ to all three. I wanted details, but thought I should let the whole thing simmer for awhile before I started trawling for them.

About ten minutes later, we started kissing again, first just affectionately, then passionately. I was getting hard again after about thirty seconds of this. I started to climb aboard, but she pushed me back and said she had to go to the loo first, to urinate and then to re-lubricate. Before she climbed out of bed, she took my head in her hands and gave me a soft, very loving kiss. I may have been wrong because of the dim light, but I thought I detected a sadness in her face as she moved away.

As I waited for her to come back, I tended to the maintenance of my erection. I wanted to make sure it was ready for action upon her return, but that return was delayed… and delayed. It wasn’t too long, I suspect, before I slid into a deep sleep, probably a combination of the wine, the excitement and the exhaustion of our love-making.


I woke up in the early shafts of morning light, all alone in the bed. I hauled myself up to a sitting position and noted the slight headache pushing against my temples and forehead. I somehow found my shorts behind a chair, pulled them on and headed out to the living room.

Teresa was there on the long, plush couch, apparently asleep. She had a bath towel wrapped loosely around her waist, a long pink T-shirt pulled over her torso, and was wearing those sort of black blindfold things people wear on planes when they’re trying to catch some sleep. I walked over to her quietly and touched her left shoulder lightly.

‘Is that you?’

‘Were you expecting anyone else?’ She smiled at this.

‘What time is it?’

‘Early.’

‘That must be why I’m still so tired.’

‘May also have something to do with the exercise we managed to sneak in.’

‘Maybe.’ She took a deep sigh. ‘So, Raymond… or should I call you Hector?’

‘Whatever suits you.’

‘Was it everything you thought it would be?’

I didn’t really know how to answer that, but rather than allowing myself to be choked by silence, I said it was even better than I ever thought. I then sucked back my lips before admitting, ‘It was one of the most fantastic sexual experiences I’ve ever had.’

‘Good. That’s what I was hoping I could give you.’

I looked down at that beautiful face and thought I saw tears trickling down from just under the blindfold.

‘Teresa, is there something wrong?’

‘No, no; everything’s just right. Look, there are a couple of things I have to do. I really have to do them before too late, and I need solitude to do them in. I don’t mean to be brusque or impolite, but…’

‘No, no, of course. I understand. You’ve got things that have to be done.’

‘Thank you.’

She sat up from the couch for the first time, pointed to the coffee table next to the couch and asked me to get her the pad of paper sitting there. I did.

She tore the top sheet off and handed it to me. ‘This is my phone number.

Give me a call. I’ll be sort of busy for the next few days, but I’ll be very free after that.’

‘Okay.’

She then slid back into her recumbent position on the couch. I grabbed the last of my things that were lying around and got ready to leave. Suddenly, she spoke again.

‘Let me ask you: do you really have any idea who Teiresias was?’

I laughed. ‘Not a clue.’

She gave a chugging laugh. ‘Teiresias was this guy in Greek mythology who had a good position; a top assistant to one of the gods. Anyone, one day he was walking along, saw these two snakes copulating, thrashed them with his walking stick, and was turned into a woman as a “punishment”.’

‘Ooo.’

‘Then, one day, Zeus and Hera—the king and queen of the gods?—they had this argument about who gets more pleasure in sex, a man or a woman.

So they asked Teiresias, because she knew both sides. Teiresias was certain: woman have much more pleasure in sex.’

‘I see. And would you agree with that?’

‘Who am I to argue with my role model?’ I laughed at that one.

We exchanged a few more rounds of banter, and then I had to go. She asked me to kiss her goodbye, which I did even though she remained lying on the couch with her blindfold on. I tried to lift it off for this last kiss, but she resisted strongly. ‘I don’t have to see you. I still see you, see you the way you were when we were one. That’s the best view, believe me.’ I relented.

I smoothened out the blindfold and leaned into her lightly. It was a warm and gentle kiss, one that promised future meetings.


But I never saw her again. For the next few days, I kept calling and getting a message to leave a message. I left about two dozen of them, some of the later ones rather angry or pitifully desperate. After the third day, when I called, I was told the number was no longer in operation.

I then drove out to where she lived. Because it was a condo, I couldn’t get past the guards. I tried to explain that I needed to see Teresa, to clarify something, but these guys weren’t very helpful. Well, to be fair, I wasn’t even sure of her apartment number or the building she was in. I thought I knew, but the guards, of course, wouldn’t let me go in and wander around to check.

I tried to describe her, but what could I say—that I was looking for a beautiful woman who used to be a man named David? I didn’t even know her last name. For that matter, was Teresa itself her real name? Was there anything about this person that was one hundred percent real?

I went to the club were he had met, went quite a few times in fact, but she never came back. At least not on the evenings I was there. It was as if she’d just disappeared.


Well, she did warn me more than once that evening that she was complex.

I guess I should always be grateful to her for letting me see that I myself was more complex than I’d ever imagined. In some ways, it was the most unforgettable night of my life. In other ways, it was a night I will probably spend the rest of my life trying to forget.

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