Shemale Ride Along Part 1

I'm going go ahead and get this out of the way. During my freshman year of college, I was confused about my sexuality. It sounds strange saying this right after calling myself confused, but I loved girls. I really did. I loved all of their shapes and curves. I loved tits, pussy and ass.

Now, I know what you're thinking. You're thinking that I'm just some gay guy that doesn't want to come out of the closet and is overcompensating. I honestly don't care what you call me. Up until freshman year, I considered myself one hundred percent straight. However, I quickly learned that sexuality is not always black and white.

I made a fairly startling realization that year. I enjoyed putting things in my ass. It started off as a curiosity thing. I had always heard, "How do you know if you haven't tried?" Plus, I learned that the equivalent of the male g-spot could be stimulated through the ass. So, I stuck my middle finger up there while I masturbated once.

I really enjoyed the sensation and it made my orgasm stronger. Just like that, I was hooked. Soon, I was putting all kinds of things up my butt. I would go to the store and buy a pack of Sharpie markers or a hairbrush to fuck myself with the handle.

I watched a lot of porn at that age.... Who am I kidding? I still watch a lot of porn. Anyways, I started watching these videos of girls fucking guys with strap-ons. I was dating a girl named Tina at the time, and I would imagine her fucking me with a strap-on while I masturbated. It was a huge turn on for me.

So, one day I gathered up my courage and confided in Tina my secret fetish. I asked her if she would be into using a strap-on on me. Her reaction was not the desired effect. She was repulsed by the idea. More than that, she was repulsed by me. In fact, she broke up with me over it, telling me, "I don't date faggots, Matt."

This struck a nerve. Up until that point, I only thought of my desire as a fetish. What if she was right? What if I really was gay? So, I tested it out. I looked up some gay porn and watched it. I watched several videos, in fact, with all different kinds of guys fucking all different kinds of other guys. I gave jacking off to it a good try, but nothing worked. I wasn't turned on by any of it.