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Driving in Arizona

I was living in Arizona and taking a break from the corporate world. I decided to start driving for the rideshare services in the area, at first I was driving in the day and not making much money. I decided to start driving overnight as I heard the tips, and the business was more consistent. Many nights I would pick up drunk, sorority girls and fraternity guys and drop them off at their destinations. A couple times I had to carry some unfortunate drunk girls from parties to their dorm door and hope they made it in OK. However, on this night, I found myself far south of the city near an Indian reservation , I knew the area as I often frequent it for good tamales and Mexican breakfast. I was about to call it a night when I got one more ride and it was very nearby so I decided to go for it. When I arrived on the scene, I saw a tall, dark woman with jet black hair down to her waist and a red dress in high heels. She enters my car quickly and was very excited that I picked her up as she said she was having a rough night. I asked her why such a rough night? She said business was slow. I said oh, what type of business are you in? She said well, I meet up with men and help massage them and please them however, they like. I said well that sounds like an interesting job. She then went on to tell me how she loved giving blowjobs and she was upset as she hadn’t given one tonight. She then asked me if I liked blow jobs. I thought for a second and then said of course who doesn’t love a good blow job. As soon as the words left my mouth, she reached from the backseat and started massaging my cock through my pants. She asked if I liked how that felt. I said of course it feels really nice. She then asked me if I’d like a blow job and I said that sounds pretty nice as well. She then went on to say, is it OK to get a blow job from a cross dresser. I said well you could’ve fooled me. I thought you were the hottest woman I’ve seen all night and I’ve been driving for about eight hours. She then continued to reach from the backseat and unzip my pants releasing my now growing cock and started jerking me off. I started getting very excited and we were driving down a dark road two-lane highway. At the time we were the only car on the road, I decided to pull over and as soon as I did, she jumped out and jumped in the front seat. She then immediately devoured my cock and started sucking me like a lollipop with immense suction and head bopping. The blow job was amazing. We sat there on the highway as cars flew by, and I was getting one of the best blow jobs of my life from a cross dressing man. Never in my life did I think this would happen, however, in hindsight, it was an amazing night , as we continued sitting on the road, I started feeling her ass and she started getting more excited and jerking me and sucking me. It only lasted about five minutes and I shot my load in her mouth and she hungrily swallowed every last drop. She then gave me a quick kiss, jumped out of the car and back into the backseat, and then I proceeded to drive her to her house. As we drove we talked a little bit more about her life as a prostitute , when we finally got to her house, she asked if I’d ever had sex with a man and fucked him anally I said no. She asked if I’d like to try. I gave it some thought and said unfortunately I think I have to call it a night. She then gave me another kiss, a nice wave, and as she walked away, she smacked her ass as she got to the door. She looked back one more time and gave me a wink and said to me I should stop by anytime. I left that night from her house not believing what I had done or experienced, but still felt that it was an amazing experience and was glad I did it. I never ever saw her again, although I drove by hoping to pick her up. Maybe someday we’ll meet again and I’ll fulfill the desire. She wished of me to guck her in the ass.

The End

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