My TS Journey

I wanted to fit it in my ass soooo bad so I could experience the anal pleasure I could see the trans women achieving in the videos I watched, they would take long strokes from cocks even thicker than my plug, and they did all this with cheeky smiles and lustful eyes. I knew I could feel even more euphoric orgasms, but I needed to train my ass to take it.

A few weeks later I was having a really horny jerk off session, my cock was rock hard as I slid multiple fingers in my ass, simulating the stroke of a cock. Eventually the urge to be fucked grew so intense that I reached for my butt plug and began pressing it against my lubed up asshole. With each push I would manage to get it a little deeper, up to the point I had it halfway in my ass. At this stage the pleasure had turned more to pain, my ass just couldn't handle the width of the plug, but I was still so horny and edging closer & closer to cumming. I resisted the urge to pull it out and began softly pressing it in a little more, just as I thought " this wont work, it hurts too much" I gave it one more little push, it was enough to pass the halfway mark of the toy and the plug was engulphed by my asshole. I let out a shriek of pain as this toy filled up my ass and stretched my hole farther than ever before. The sensation was so intense I instantly shot my load all over my chest, with each orgasmic pulse my asshole would grip tighter on the plug. I had done it, I had pushed past my previous limitations and over the coming months I became quite good at handling the plug, even to the point were I had stretched my ass so much that all I felt was pleasure.

I found myself starting to visit escort sites from time to time. It was nothing more than curiosity at first as I never thought I would ever pay for sex, I knew nothing about it other than it was illegal were I live. As the weeks past I became particularly interested in one escort "Jessica". She was close to where I lived (about 15 mins away) and she had great reviews on the site, not to mention she was drop dead gorgeous in her photos.