Which shemale pornstar converted you?

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Kimberly Devine. She actually confirmed to me that finding Trans women hot was a thing for me.

The first time I thought about it was when Lisa Edlestein played a transwoman in an episode of Ally McBeal. I thought ,hell yeah if I was with a hottie like her ,a bulge in her panties wouldnt be an issue. In fact ,it might be HAWT!

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Barbie Woods, back when I hit puberty 15 years ago there was talk about a Transsexual golfer on the news here in Australia, being the young boy I was I obviously had no idea who or what that was so I googled, pretty much the only image on google was her back then, I was hooked instantly!


I think it was this exact picture.
 

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Bailey Jay certainly was one of a few to get me interested.

Just started to curiously browse shemale stuff and most of what I initially saw was meh.
Then I stumbled on Bailey and saw how hot she was so kept looking up her stuff which led me to find some other shemales that I liked.

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one more vote for Sarina Valentina

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Recently 'converted' thanks to Kimber Lee, who I'm not sure has been mentioned yet. She's incredible, and with a huge cock too. I would love her to take my TS cherry:

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I don't know the name of the model, it was an ad in the back of a Hustler magazine from the late 80s for a Best of Both Worlds video.

That was the first time I ever saw a woman-looking person with a dick and my young mind was blown. I'm a big Sci-Fi fan and always read

about aliens that could be both sexes so that never bothered me. After that every chance I got I picked up shemale porn mags & videos.
 
For me it wasnt porn that got me hooked.

It was a holiday in Thailand, I was at one of those cheap bars that are packed with beautiful asian girls. I was a little ***** and this one girl caught my eye. She had fantastic legs and a short dress that you could tell she had a nice thigh gap. (I was always a fan of thigh gaps on skinny chicks cos it means you can really get balls deep in them when your fucking them)

Anyways, this chick ticked all the boxes and I ended up taking her upstairs into one of the hourly rooms.

I stood with my back against the wall while she crouched down and started to give me the best blowjob I ever had in my life. (I now realize it was her plan to get me to cum in her mouth so I didnt find out her secret in her pants.)

I could have easily cum a pint down her throat but I wasnt letting her get off that easy. In my mind I was thinking "im gonna fuck this little slut in her arse and make her cry" (I had been trying to find a girl who did anal for my whole holiday, but they all declined due to my rather long and girthy cock)

My plan was to fuck her pussy and then rather than ask "can i fuck your ass for extra money" I was just gonna stuff it in her ass without asking after I managed to spit enough saliva on her asshole to lube it up.

So, I put my hands under her arms and lifted her up from the crouching position, turned her around and pushed her towards the bed. I lifted up her skirt from behind and pulled down her thong. As I glanced at what should have been a dripping wet pussy, I noticed a set of balls and this fantastic looking asshole.

Her erection was growing as I gazed at it and I thought to myself "Fuck it, looks like im finally gonna get some anal after all"

She spread her ass cheeks and took my whole length with just a slight whimper. Inside her ass was incredibly tight as it gripped my entire shaft like a vice.

I fucked that girl in every position you could imagine until her asshole gaped every time I pulled my cock out.

Then I pulled off the rubber and shot my load inside her asshole.

Here are a couple of pics

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Eva Robbins http://www.hungangels.com/vboard/attachment.php?attachmentid=138695&d=1193804461
Cristina Bianchini https://shemalestardb.com/cont2/2/21271_4.jpg
+ many more!

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i don't remember which video but if i had to pin it on the first trans girl i watched that turned me LOL id say Bailey Jay maybe
 
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