My TS Journey

I'm a straight, married guy in my 30's, at least that how I appear to everyone that knows me. I have an intense obsession with Trans women that I have been indulging since I was a teenager. Over the years this fixation has grown into something that ranged from watching porn initially, to having my ass pounded on multiple occasions by gorgeous trans escorts.

Thinking back to when this all started, I remember I was 15 when I saw my first shemale porn video, I was searching through some of my favourite categories "Big Tits, Anal, MILFs" when I came across a video of a trans woman being ravished by 2 men. I remember being shocked when I saw this beautiful 'woman' being passionately fucked while her large cock flopped around on screen, after a minute I snapped out of it "OH THIS IS SO GAY, FUCK THIS" I thought as I instantly clicked back to some heterosexual porn. In that moment though I think a seed was planted, even to this day I remember that beautiful trans women's features clearly, her bronze skin, curly blonde hair, tight athletic ass and of course a glorious cock that put my teenage package to shame.

Over the years I found myself incorporating more trans porn during my masturbation sessions. I would usually start & finish watching straight porn but I would always find myself building to climax watching beautiful shemales being pounded. As time went on I had made the transition to only watching shemale & ladyboy porn. It wasn't until I was 17 before the urge to explore my own sexuality began to grow, I found myself day dreaming about being penetrated by huge shemale cocks. I started fingering my ass while I masturbated and it took me to new heights of pleasure, I wanted MORE!!

Around the age of 20 I started looking into new ways to heighten my sexual pleasure, I did this in the form of sex toys. I purchased a butt plug & poppers from a local sex shop, at first it appeared my eyes were bigger than my ass could handle. I never really got close to being able to fit the butt plug inside me, even when using the poppers, at most I would get it a third of the way in but as the toy widened my ass began to hurt and I would have to stop.