Boyfriend Hooker Experience 22 [F]

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.

Finally he unlocked the door and I hopped into the passenger seat as quickly as I could. James took a wad of money from his pocket and jammed it into my bra. He was sure to grab a handful of my boob on the way out. This is as far into the plan as I was told so I figured we were headed back home. To my surprise James drove down some side streets and into an alley behind a shopping plaza. He stopped the car and unbuckled both our seat belts. As he undid his pants he told me to get ready because he was going to get his money’s worth from this hour. He pulled his soft cock out of his pants and told me to get to work. The sun was almost set so now at least we had the cover of darkness. I scooted up and put my knees on the passenger seat so I could bend over and suck him off. Once I leaned over he put his one hand on the back of my head and jammed the other one back in my bra. This was the roughest James had ever been with me and I was really into it. As I worked to get his cock hard he pulled his hand from my bra and found his way up my skirt. He didn’t even bother to move my panties as he jammed a finger into me. For a few moments I forgot we were in a public parking lot as we went after each other like high school kids.

After his cock was nice and hard James pushed me off of him and back into my seat. He told me to get ready for him. With the events of the evening so far I was already more than ready and told him so. He then told me No, get yourself ready for me. He reached down and grabbed my booties and spun me to him. I had one bootie on the center console and he put the other one on the dash. James had never told me to play with myself before and just the idea of it sent a shimmer through my body. While making sure to stare him right in the eyes I pulled my skirt up my hips and slid my hand down into my panties. I pulled my top down as low as it would go to make sure he had a good view. Biting my lower lip I slowly began running my fingers around in my little red panties. I made sure to put on a show as I ran my hands across my body while softly moaning his name.

I was really getting into it when he jumped out of his seat and ran around the car to my door. He opened both passenger doors and told me to get in the back seat. As I crawled into the back seat he dropped his pants and tried to get in behind me. However the backseat was way too small for him to get behind me and fuck me doggy style. He grabbed my hips and pulled me backwards out of the car. About the same time my shoes hit the ground he rammed his hard cock inside of me. Half my body was still bend over inside the car and he was just punishing me with that dick. He was using me as a cheap hooker in a back alley. James didn’t care about me at that point, I was simply his fucktoy.

After a relentless pounding James backed away and pushed me to the ground in front of him. He didn’t care that we were outside anymore as he got me on my knees. A few quick strokes with his hand and he unloaded a hot mess of cum all over my face and chest. I started to get up but he pushed me back down. He told me that he paid for a full hour and he was going to use it. He took me by the head and told me to suck him until it was clean. All of the sudden we heard a loud bang in the alley and could hear voices. I froze with his cock still in my mouth. Looking up at him for guidance I was afraid to move. No more than 100 feet from us some workers had come out to dump the trash and have a smoke break. One or two of them started walked over and asked James if he needed some help. It was obvious we didn’t belong in that alley. James quickly pushed me into the back seat and zipped up his pants. He got back in the front and drove us out of there. Neither one of us spoke until we were back on the main streets.

I just laid in the back seat as I was exhausted, covered in cum and my skirt was pushed up over my hips. When the car came to a stop I got up and was ready to get back in my car but we were not at my car. We were back at the bus stop where it all started. James told me this is where he picked me up so this is where he would let me out. He told me he would wait a few minutes before he unlocked my car with the app so I had time to walk over. I was going to argue with him but a bus was starting to pull into the lane and I didn’t want to attract any more attention. I pulled my skirt down as best I could and slid out of the back seat. Before I even turned around James was pulling off.

Just my luck the bus was unloading a full load of passengers into that parking lot. My car was no more than a few hundred yards away but it felt like miles. I had no idea what I looked like after my parking lot fuck but I’m sure it wasn’t good. Looking down I could see the cum spots on my shirt and where it had dripped onto my skirt. I’m sure my face had cum and smeared makeup everywhere. The parking lot suddenly felt like a hallway in high school with everyone looking at me. As I reached my car I prayed that it would be unlocked but as I grabbed the handle it didn’t open. Looking around for an idea I made eye contact with two guys getting out of a car across from me. One of them began walking towards me and asked if I needed help. He was no more than feet from me and he had to have seen the mess I was. Feeling the blood rush to my head I was panicking when I hear my doors unlock. I shouted I’m good to him and dove into my car.

I locked my doors and took few deep breaths to settle my nerves. While I began to recount the events of the past few minutes I found my hands beginning to wander back into my panties. James had fucked me hard but I never got a chance to cum. The excitement of the night was all coming back to me as I pulled my skirt back and slipped my fingers inside. I braced my arms off the steering wheel as the rush of an incredible orgasm rocked my body. I let out an amazing scream before I remembered I was still in a shopping center parking lot. To my horror I looked up and there was a man standing at my side window. I was stunned until I realized it was James, he had circled into the parking lot and was watching me the whole time. I asked him how much of my little performance he had seen up close and he said enough to get him ready for round two at home. I smiled and backed out of the parking space. I drove home with one hand on the wheel and one keeping myself ready for another fuck.

Source: reddit.com/r/gonewildstories/comments/fx7cn5/boyfriend_hooker_experience_22_f