I was 25 years old, had just finished law school, and had a great girlfriend -- who I loved. But there was a desire lurking deep in my mind...I fantasized about trans-girls. I remembering stumbling across a video on pornhub during college, and was surprised to feel the blood rush to my cock as I watched a young CD strips off her panties to reveal a perfect, smooth cock. After only 20 or 30 seconds, I immediately came -- experiencing the most amazing orgasm I have ever had. Suffice to say, I never turned back. Almost every day I fantasized about meeting a trans-girl, and though I had girlfriends and hookups throughout that period, I would always imagine a stiff she-cock bouncing back and forth as I made love.
As I took my last exams, and started preparing for a new job, I found myself with about a month of free time. My girlfriend was on assignment for a magazine, and I was alone -- left to my own devices and desires. This was my moment to make a real effort hookup with a trans-girl; and I had my eyes on a cute little thing whom I suspected might be more than what she appeared to be.
Her name was Jessie, and she worked at the pet store where I regularly got food for my cat. She always caught my eye: cute, petite -- about 5'3", maybe 110 lbs soaking wet. She had green eyes, a smooth complexion, small perky tits, and a cute, tight ass. Her hair was brown with pink highlights. I knew I wanted to make a move.
I was relatively confident that she recognized me as a returning customer, and so I started going to the store more often -- making up a story that I was planning a large aquarium. It was at this point that I introduced myself, made her laugh, and eventually caught her checking me out as I was contemplating what kinds of fish would be best in a community tank. We locked eyes a few more times that day, and I chatted with her at the register as I bought some cat treats, and promised to come back for the fish tank supplies. As I turned to leave the store, she called my attention -- offering to help me select the fish and plants for my tank the next time I was in. Seeing my opportunity, we swapped numbers under the guise that I would text her next time I was swinging by -- just in case she was not on shift. We both knew why we actually swapped numbers...