Towards the end of college I was dating a guy, named James, who was into the whole stranger sex thing. For example we would go to a party and towards the end he would find me and pretend he was picking me up and taking me home for the first time. It was fun and harmless. Added a little excitement to the night sometimes. Once we got out of college we both started working so obviously fewer parties and more real life.
One night James suggested that we do it again but I would play a hooker and he would pick me up. I was into it right away because who doesn't like a little extra excitement in their sex life? However, as he started telling me his whole elaborate plan it was obvious that he had been thinking about it for a while. He wanted to actually pick me up off the street. I was reluctant but willing to give it a try for him.
When the night of the plan came I tried to follow all my instructions perfectly. James had told me to find my best hooker-looking outfit. I wanted to look sexy but I knew other people would see me. I had just gotten a pair of high-heeled black booties and I knew they would be perfect for my outfit. I decided on a stretchy red skirt that I could pull up and make super short when I was ready. A little black tank top I had matched perfectly with the black boots. For my classic hooker look I went with a red bra that definitely was visible with the little tank top. I originally decided no panties but then I found a tiny red g-string that just seemed perfect. To top it off I grabbed a few condoms and put them in my bra.
James was going to pick me up on a street corner that was on his way home from work. I drove my car over to the nearest shopping center and parked. I texted him that I was there and he told me to get out and leave everything I had in the car even the car keys. He told me to walk out to the place we agreed on and wait for him. As I stepped away from my car I heard it lock. James had used the app and locked it from his phone. The sun was starting to set but it was still plenty bright out and people could easily see me. I looked like I was either a hooker or about to hit the hottest club in town and since it wasn't 7 pm yet I think the answer was obvious.
Walking out to the street my heart was pounding. I didn't have anything on me except the condoms in my bra. I hadn't done anything illegal but I felt like I was on the run from the cops. Once I found the spot on the street corner I realized it was a damn busy intersection at rush hour. I tried to pull my skirt as low as possible but it barely covered my ass. It felt so much longer in my bedroom mirror than it did standing out in the open. James had told me he would pick me up but without my phone I had no idea how long he would be. Looking back I think he wanted me to stand out there on display for all to see. Minutes standing on the sidewalk seemed like hours. Every time I saw a car that looked like James I took a few steps forward. This certainly got some strange looks and a few honks. I swear one guy actually pulled over to pick me up but I walked the other way. My mind was racing as I was both nervous and incredibly turned on.
After what seemed like hours I saw James. He pulled into the bus lane and I tried to get into the passenger seat. He just rolled down the passenger window. Annoyed, I leaned in to ask what the fuck he was doing, I was ready to get off that street. He started with the whole act of, Hey baby you working tonight? How much for an hour with you? Since I was stuck there bent over in my hooker shoes with my ass sticking up I figured I better play along. I told him $50 for the hour and he can do whatever he wants with me.