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Old 11-27-2012
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crosstown crosstown is offline
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Smile My first experience with a ladyboy - a true story.

I have always been excited by lingerie, especially the feel of my cock and balls in it. I have stolen panties to wear while masturbating and even bought lingerie outfits to play with at home. Being a bit of a photographer I quickly discovered that I could dress up and photograph myself.

What I didn't realize till recently was that I was turned on by other TV/TSs too - the more passable the harder I would get. I didn't think much more of it though. I'd never have considered myself bisexual and I'd only ever had sex with women. But then, not long ago things changed completely. I had an unexpected torrid but brief affair with an astonishing lady-boy.

I met her at a Thai takeaway joint. She was serving behind the counter and frankly I thought she was a she. She obviously had an eye on me because she came over to where I was sitting and introduced herself. Her name was Yindee. She wasn't short - probably 5'10". She was of slight build but had large breasts which she was clearly proud of. I could tell this by the way she would lead with them when she turned her body. She had long black hair, immaculately groomed; big lips, high cheek bones and beautiful skin. She had hips too but her ass was flat. I thought this was odd. We had a little chat - she was so sweet and kind. We agreed to meet up later. When she left she gave me a little peck on the cheek. Watching her walk away I suddenly noticed while staring at her ass that she was a he. I was genuinely shocked.

When we met up a few weeks later, we had a drink and ended up back at her flat. We kissed and played around for quite a while and we were both getting aroused. Then she did something I was really not expecting - she insisted on crossdressing me! Of course I was keen as I already had a fetish for panties but I'd never had a full transformation. She started by choosing her sluttiest outfit, with gaudy tiny pink panties, lace top stockings and suspenders. Then full makeup, a pink wig and heels. After admiring her creation by making me parade around the loungeroom (while taking a few clandestine pictures on her iphone), she drew me towards her and firmly pulled my head down on her elongated and strangely crooked stiff prick. She was still wearing panties so I wasn't sure how big it actually was - but when I got closer I could see it was huge - thin but long. I'd never sucked a man's cock before but I guess I knew what to do. I licked up and down the shaft wetting it with my saliva before taking the head in my mouth. Slowly I took more in till eventually it was on the way down my throat. It was ironic really because I'd many times tried to force my own cock down girl's throats before. Now it was my turn. I managed to resist the gag reflex long enough to get more than 2/3 of her cock in. I was actually deep throating, taking the shaft most of the way in and out rhythmically, up and down along most of the rod. She said something in Thai which was obviously an expression of surprise. As she was moaning she was fingering my cock, balls and finally my ass. She licked her thumb and pushed it up my ass. I looked up at her and she winked. I sensed a change a pace.

Suddenly she stood me up, bent me over, pulled up my skirt, parted the pink panties and drove her tongue deep in my asshole. It took my breath away but before I could get used to this I felt the head of her cock pressing on my anus. Involuntarily I was puckering it tightly shut! She pressed a little harder. I was really scared. Finally my anus surrendered and opened. With one hand she softly rubbed my cock through my panties while at the same time slowly pushing her cock up my ass. She was gentle but it hurt like hell. By slowly rocking her hips she inched it in further and eventually she had the whole thing in there. It felt like I was impaled on a fence post. Gradually the pain eased and she started to pump me. At this point she whispered in my ear that she loved New Zealand men! She then proceeded to fuck my virgin ass harder and harder and to be honest I loved it.

Finally, she withdrew from my ass and motioned me to lie on my back. Accompanied by loud moans and very slow deliberate strokes with her hand, she blew herself across my stomach and face. I've really never seen so much come - really a small river of it - certainly more than I would have imagined possible and certainly much more than I had ever produced. My face was half covered as well and some of it had even found its way into my mouth. It gathered in big pools on my belly and then spilled onto the floor. My ass was stinging like mad but I was more fascinated by the come sea. I was staring down at it on the floor when she tapped me twice on the knee and motioned with her head to pay attention. It was not over yet.

She addressed her mouth to my cock which by now was aching from being hard for so long. She masterfully fellated me and I could have come right there and then but she had other plans for it. She held it in her hand and positioned me behind her, all the time gently jerking me onwards. Without really realising what was happening I was already penetrating her asshole. Her ass felt gritty but surprisingly tight. It was quite a sight. She was on all fours, polka dot panties pulled to the side and my cock planted right in her ass. It was an unfamiliar view - because I could clearly see her cock bobbing between her legs and her ball sack bouncing left and right.

But my god did she squeal! I stopped - thinking I was hurting her but she angrily shouted "fuck me, man". I pounded away for a few minutes - she knew I wouldn't last long. Then she pulled herself off me, turned around and held her lips just an inch from the tip of my cock. She looked up at me and smiled cheekily. I'm sure I didn't disappoint her as I unleashed a mini torrent of my own. She clearly enjoyed being comed on. She moaned and groaned, licked and cooed. I felt oddly proud of myself.

It was extraordinary, unexpected and completely mind blowing!
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  #2  
Old 11-27-2012
jodarling jodarling is offline
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So what happened next, have you seen here since?
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Old 11-27-2012
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crosstown crosstown is offline
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I saw her for a few months. It was a truly wild and bumpy ride. We had a few more encounters like the one described plus one other super bizarre episode that I'll describe in detail later.
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