tagTranssexuals & CrossdressersMy Transsexual Lover

My Transsexual Lover

byDark Warrior©

I looked around the café as I entered, checking out the patrons. My eyes fell upon a beautiful woman, alone in the corner booth. She seemed not to have noticed me, her attention still on the coffee cup in front of her.

She was, as near as I could tell, about 5'10" or thereabouts, with a womanly build and just the slightest hint of muscled arms – an attribute that never turned me off a woman. She had curly, shoulder-length black hair, and a large set of perfectly rounded breasts barely contained within a white, low-cut top. Her eyes were hidden by a pair of large, very black sunglasses. Below the table, she wore only a black skirt, and my eyes ran over her long, smooth legs admiringly.

With a smile I picked up my courage and strode over to the woman, her face turning up to look at me as I came over. I took the chair opposite her in one hand.

"Mind if I have a seat here?" I asked, putting on my most charming smile. She paused a moment, and I assumed she was looking me up and down from behind the safety of her glasses.

What she saw was a 23 year old, 5'11", with a fairly average, lightly muscled build. I had short, brown hair, and blue-green eyes. I was what you would most likely call 'ruggedly handsome'.

"Sure, be my guest." She spoke in a thick Italian accent. I took the invitation up, seating myself opposite her. I motioned over to the waitress, quickly ordering a coffee.

"So, may I have the pleasure of knowing your name?" I asked, looking up into her perfect face. Again she paused a moment, a smile playing at one side of her full lips.

"Vivian." She finally said, her foreign accent sweet on my ears. She seemed to be waiting for me to respond.

"Nice to meet you, Vivian. I'm Luke." I said, accepting my coffee from the waitress who had just returned. I took a sip, decided it was too hot, and put it down on the table for a moment.

"I don't know how to say this, but… well, are you single?" I asked, provoking the smile from her.

"Yes, I am. And there's only one reason why you'd ask that so soon after our meeting, am I right?" Vivian said. I blushed.

"Well, yeah… I was just wondering if you want to do something sometime." I said.

Vivian picked up her coffee and finished it, before answering my question. "Why, sure, honey. If you'll excuse me, I have somewhere to be, but how about tonight?"

I couldn't believe my luck. "Sure, sure. Where do you want to go?"

"Well, I know a good place not far from here. We could meet here at, say, 9-ish?" she asked after a moment.

"Sounds good to me." I said with a grin. She smiled and nodded, before standing up and stepping up next to me. She bent over me and kissed me softly on the lips, her lips pausing a moment just centimetres from mine to tease me. She whispered goodbye before she pulled away from me, then left the café.

I ran a hand slowly against my lips, a smile spreading on my face. I then returned to my coffee.

* * *

I sat outside the closed café, waiting for Vivian. I glanced down at my watch: just a minute before 9. I heard the sound of a car engine, and looked up the nearly empty street to see a red Porsche coming down the road slowly. I looked longingly at the car, my eyes following it as it came closer and closer. The look on my face was that of surprise as I saw who was driving the Porsche… Vivian. As she brought the car out in front of the café, I walked over to the curb, leaning into the convertible.

She was dressed in a red dress, which revealed the top of her cleavage and a fair amount of her legs. For the first time I looked into her beautifully deep, dark brown eyes.

"Hey Vivian." I leant over and kissed her softly, before looking down at the leather interior and giving a whistle. "Nice wheels." I said.

"Thanks, hon. Get in." she purred, opening the passenger door. I climbed into the passenger suit, shutting the door behind me. Vivian turned the car back on, the engine coming to life with a purr of power. She pulled back out into the street, immediately continuing the way she had been going.

"So, what's this place you're taking me to?" I asked.

"A club. I know the people who run the place." She replied, never taking her eyes off the road.

"Sounds good." I said, smiling as I watched her smooth hands on the wheel.

After just a minute more of driving and idle chit-chat, Vivian pulled the car up in front of a building, highlighted by a neon light, above the door, that read "Midnight Moot". The car turned off with a gentle purr, and Vivian pressed a button, and the soft-top began to cover the car. She got out, followed soon by me, locking and immobilising the car. I followed her to the door, where two burly bouncers stood on either side. One of them broke out with a smile and practically ran forward to take Vivian into his huge arms. He kissed her softly on the cheek.

"Ah, Vivian! Good evening! Please, go right through!" he said, releasing her from his grasp. She smiled at the bouncer, before gesturing back at me.

"He's with me." She said softly, and the bouncer nodded. Vivian stepped forward and entered the door, and as I followed her, the bouncer gave me a wink and a smile. The other stared at me with a rather odd look on his face, but I ignored him and walked in after Vivian.

The thump of the dance music that I had heard ever since getting out of the car became many times louder now as I stepped into the club. The door swung shut behind me, and I looked around the club. There were lots of people, most of them on the dance floor, which was illuminated by coloured strobe lights. Out the front, there was a DJ, the source of the music. Further over, there was a bar, a few people sitting on stools with drinks in front of them.

"C'mon, Luke!" Vivian yelled over the music, taking me by my wrist and pulling me towards the bar. She sat on a stool, and I sat down next to her. The bartender came over, a wide smile on his face.

"Ah, Vivian! What can I get you?" he asked.

"Nothing for me, thanks. How about you give my friend here your specialty?" she replied, gesturing at me. The bartender looked at me, smiled and nodded, before beginning to prepare his "specialty". After a moment, he placed a long glass in front of me, filled with a black liquid.

"Thanks. Add it to my tab." Vivian yelled out, and the barkeeper nodded before hurrying to take someone else's order. I stared at the liquid in front of me somewhat uncertainly.

"C'mon, Luke… it's great, give it a try!" she yelled out, and with no further invitation needed, I picked up the glass and threw the contents back, my face contorting as the bitter liquid went down my throat, but it was followed by a very nice after-taste. I put the empty glass down and nodded in satisfaction to Vivian, who smiled, before ordering me another.

* * *

I gave a moan as my eyes blinked open, followed soon by the splitting pain in my head.

I could remember little of what had happened at the club; but now that I think about it, I should have realised. Vivian hadn't drunk a thing, as far as I could tell, but me… I had gone overboard… had she meant to get me drunk?

The answer became clear as I suddenly realised where I was. My hands and legs were bound, so that I could not move, and I was staring directly down at a bed. I tried to shake my hands and legs, only to realise that they were tied firmly to either end of the bed.

And then I realised something else. I was naked.

"Ah, you're awake." Came the familiar purr of Vivian's voice. I could feel her straddling my back, but, before I could say anything, she had reached around and placed a ball gag in my mouth, quickly securing the gag behind my head. I tried to say something, but it was no use, and everything I said was muffled.

"Now, now, Luke. Just relax, and I promise I will take you places you never thought you could go." She purred sexily into my ear as she gently kissed my cheek. Then, a blindfold was placed on my eyes, and my entire world went black. Again, I tried to say something, but succeeded only in making muffled noises.

"Please, just relax, Luke. There is nothing you can do – just give in to temptation…" she whispered, and I felt her lips move away from my cheek, kissing down the middle of my back, lower and lower, her hands now reaching out and cupping my ass cheeks. She began to knead the globes of flesh as her mouth reached my ass. She gently spread my ass cheeks and her tongue ran, slowly, down the crevice of my ass, and I could not help but moan into my gag at the feeling of pleasure I got as her tongue flicked against the entrance to my anal passage. She stopped and pulled away for a moment, before spreading my cheeks further, her tongue now descending again on my ass crack. Her tongue squeezed its way into my virgin back door, gently licking all around the tight hole, and I gave another moan into my gag as my cock began to twitch underneath me and my anus began to give way to her tongue, slowly stretching and opening up for her. Her tongue moved further into my forbidden zone, still slowly licking its way around the passageway. As she moved slowly and slowly further into my tight hole, I heard the sounds of her taking off her clothes, the teasing sound of her dress's zipper coming slowly down drifting into my ears. Her hands began to squeeze my ass cheeks now, not painfully, but squeezing on them as her tongue went as far into my ass as possible. She licked frantically for a moment, before slowly pulling out, and then going back in.

Oh, the forbidden pleasure of my ass being tongue-fucked was just too much… I could feel my cock hardening at the thought of this beautiful woman taking control of me, tying me down, securing me so I could not escape her passion, doing whatever she wanted to my naked body…

And then, she pulled her tongue entirely out, and I heard her smacking her lips. I moaned softly into the gag, strangely seduced by the woman's actions. I could feel her hands release my ass cheeks now, and now they were gliding up my back, up, further and further, before she began to massage my shoulders. I could hear her soft breathing just inches away from my ear.

"I have a surprise for you, Luke." She whispered, massaging my shoulders in slow, sensual strokes. "You may not like it, and… that is why I had to do this to you…" she whispered, her hands now moving away from my shoulders and up my arms, her hands gripping my wrists where the ropes that bound me were, to prove her point.

I wanted so much to just say: "Surprise me. I will love it, whatever it is. I love you, Vivian. I love you. Surprise me."

And then the totally unexpected happened. I felt something… something hard… pressing against my anal passage.

"It's real, Luke. It's now a dildo. It's real." She whispered, and everything started to fall into place. I started to squirm, but there was no use; she had too firm a grip on me, and besides, the ropes binding me were too tight.

"I'm sorry, Luke. I'm sorry… I'm a transvestite. I wanted to tell you, it's just… it's so awkward, and I loved you so much from first sight…" she whispered, her cock pressing between the globes of my ass, teasing me at the entrance to my virgin asshole.

Did I really want this? No, I didn't. I didn't.

I began to say something, but it was muffled, and I tried to squirm from her, but it was too hard.

"I'm sorry." She repeated, before her cock-head slowly began to push into my depths. I moaned in pain and pleasure as my ass cheeks tightened around the head of her shaft.

I was lucky, in that her cock was not large. It was, perhaps, 4 or 5 inches long, and only about an inch or two in diameter.

But, at that point in time, I could've sworn it was as big as Godzilla, as it pushed further into my hole. I heard Vivian grunt with the pressure of my ass around her cock, her hands now grasping my hips, steadying them as she pushed her cock further into me. I bit down as hard as I could on the ball gag in my mouth as she pushed in the remainder of her cock, until she was buried hilt-deep in my asshole. She released her breath as she pulled out, slowly, and I relaxed for just a moment. But, half-way out, she jammed back in as hard as she could, eliciting moans and gasps from us both. Again she pulled out slowly and slammed back in as fast as possible, continuing this motion until my ass began to stretch a little further, and she began to get a more steady rhythm going, in and out, and I realised that the pain was starting to subside.

"Oh, yes, Luke…" she whispered quickly, her hands clenching my skin painfully. And then, as if out of nowhere, I felt her cock release its seed directly into my ass, once, twice, before her cock became limp. As this happened, I knew my own orgasm was not far off, and, sure enough, I soon exploded all over the blankets of the bed below me. A moment later, her body collapsed on mine, and I could feel her huge tits pressing into my back.

The huge tits of the transsexual who had just taken my anal virginity.

And I loved it.

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