First Experience - Free Shemale Story #4 

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First Experience

I grew up in a very religous house, my mom was pretty easy going but my father was a hardcore Christian. Like, I believed that when my parents had sex it had to be the missionary position and that was it. At birth, my father of course wanted a boy. They ended up with a very feminine boy and according to my dad it was a sin to be anything but straight. So when I hit the age of eighteen I was out of there. 

I packed my bags, kissed my mom farewell and hit the road with four hundred bucks in my pocket. 

It took me about five days to make it from Maine down to New York and I tried to save every cent I had for when I got there. So basically I starved for those five days till I got into New York safely. I arrived and gave my parents a quick call to let them know I had gotten there safely. My dad hung up in my ear. 

I found a run down place to stay, it was a real dive but I had no choice, I only had a hundred bucks left. I needed to find a job quick if I was going to survive in this city. It was going to be tough being on my own. It felt good though to be on my own and able to be myself. It was the first time I could dress as the woman I felt I was. And I think I was beautiful. 

Quickly I realized that I wasn't going to get a job right away. I needed money though, I was already two days late with my rent and if I didn't have something by tomorrow I was going to have to head back to my parents house and that just wasn't going to happen. That's when I made the choice to becoming a working girl. My only problem with that was that I was still a virgin. I would just have to suck it all in and make some cash. 

We all do things we are not proud of and at this point I knew this was going to be one of those things. Nothing was going to send me home begging though. So that night I dressed myself up, packed on the make-up and headed out the door. I stood outside realizing I had no idea where to go. So I just started walking. Half an hour later my feet were getting tired in the heels I had put on, I couldn't walk any farther. I was about to turn my ass around and head back to the slum of a room I had when a car pulled up beside me and asked me to get in. He was a big bear of a man, not really my type, but I had no choice, I needed cash. 

He parked in a dark, empty parking lot and started pulling at my clothes and groping at my body. I got nervous because this man had no idea I had a penis and I didn't think I wanted him finding out. I pushed him back against his seat and ran my hand over his leg to his zipper. I thought I was going to gag at the thought of putting my mouth anywhere on this man. I closed my eyes and just did it. The most humiliating part of this experience was this man spilling his cum all over my face. He paid me forty dollars, then asked me if he could get more if he paid me more. As he drove into me I kept my panties on to hold my hidden surprise from this guy. I exposed my bung hole to him and he was happy with that. 

I got my rent paid for another week with just that one nights experience. Luckily by the end of the week I had landed a job waitressing at a local bar. I had to venture out for one more night to make another weeks income but never did it again. It certainly wasn't the most romantic way to lose my virginity but I'll never forget how it all happened. 

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