Just to make a little extra money I decided to become a livery driver last year. Being a 'people person', I thought it would be interesting as I would meet all kinds of interesting characters driving them around town and into New York City.
These are some of my 'tales' of the more interesting riders I encountered;
# 1 - The Park
Another time I picked up a girl near the park. She had been fighting with her boyfriend and was rather upset when she got into my car. I asked her if she was ok and she told me all about their argument. It seemed that he was cheating on her and she had found out from a mutual friend.
"Men suck", I told her, just making conversation. "Yes they do!", she agreed.
" I use to have a girlfriend and she never gave me any trouble but this guy is a real jerk and cheats on me all the time. I should have stuck to dating women," she told me.
Before she got out, I gave her my card and told her if she was interested in dating women again, to call me. She said, "Maybe I will!" and exited the car. I watched her as she walked away noticing her cute little body and flowing blonde hair.
I was surprised as she called me later on that day asking me if I wanted to meet up with her at a local restaurant. I accepted her invitation without hesitation. I knew it meant she wanted more than just dinner. Her perky ass and boobs made me guess she was probably in her late twenties.
I arrived at the restaurant first and told the waiter I was expecting someone so he showed me to our table. She arrived about 10 minutes later. I stood up to greet her.
"I was afraid you wouldn't show up.", I said.
"Oh no, I wouldn't do that.
I
called
you
, remember?
"Good point. So what is your name?" I asked.
"Charlene, but my friends call me Charlie".
Cute name, I thought to myself. You could see by her muscular build that she was probably a tomboy and seemed to fit the name, "Charlie". I thought it was cute as it matched her personality.
She began telling me all about what a jerk her ex boyfriend was and that she had broken up with him earlier that day which was why she needed a ride home.
I kind of expected that she was using me on the rebound, but I didn't mind as she was beautiful and anxious to date girls again. I was just what she needed. There would be no emotional attachments between us, just pure sexual interludes. That's what I was looking for anyway, and I was hoping she wanted the same.
After dinner we headed towards my car. She told me that she had taken a lift and would therefore need a ride home. I was glad to drive her hoping she would invite me in.
On the ride to her house, she reached over and grabbed me between the legs, rubbing her palm over my genital area. She slid over a little to get into a better position.
"Oh, wow!", I said as she continued to rub and then unbuttoned my jeans at the waist. She slid her hand down between my legs and started to play with my lower lips. I became so aroused as she wanted to have sex out in public. I knew she was a little wild and wasn't going to stop at just heavy petting.
"Oh, Charlie, don't stop!", I moaned.
"Take this next left into the park", she suggested. "It's late and there isn't anyone around".
My arousal heightened as I knew we were about to have sex in a public place.
I drove down the dark road that seemed to go nowhere and pulled over. I turned off the engine and it was immediately pitch black. Only the light from the moon allowed us to see anything.
We jumped into the back seat and started to undress eachother. My jean shorts were already undone and pulled down to my hips as she tugged at my underpants until they slid down to my ankles. Pushing me onto the back seat she began to kiss me as she ran her hands over my pubic area. I was so aroused, I parted my legs anchoring them on the rear door and let her have her way with me. She went at me fast and furious. I was in heaven.
Then it was my turn to pleasure her. We switched positions and I kissed her deeply while allowing my fingers to caress her as she moaned with excitement. Other than the moaning of us both reaching climax, the only other sound was the chirping of the crickets from the nearby pond.
When we were done, we headed out and I drove her to her apartment. She thanked me for a great time and told me she would call me so we could get together again.
I waited in anticipation for weeks. She never called.
#2 - The Night Shift
It was well past 5 AM when I was just about ready to call it a day when I got a call to pick up a woman by the name of Sarah at a local all-night diner.
Shortly after I arrived, she came out and got into the back seat announcing that she was bushed from the shift she had just completed. I told her that I too was extremely tired from riding around most of the night, even though I only started driving around 11 PM.
She was rather cute and had a tight waitress uniform on that reveled her big bosoms as they stretched the buttons of her top to the max without popping open. We made small talk and she told me she also had a day job and was saving to buy a new car. It made sense as she took Ubers back and forth to work.
We seemed to click and she asked me if I was able to drive her down the shore on a Friday night. Not through the company, but more on my own time. I told her I would, so we set it up for me to get her Friday night and take her to her summer house at the Jersey shore.
After my normal shift on Friday I arrived at her apartment around 7PM. She was ready to go. I told her she could sit in the front seat as I wasn't driving for the company, but for myself. We agreed on a modest fee as I didn't want to soak her for the ride. I told her I would probably stay down the shore and go home on Saturday.
We talked and talked the entire hour to the shore and seemed to hit it off really well. I liked her and it seemed that she liked me too.
When we got to the house she asked me if I wanted to come in for a drink. I accepted her invitation and followed her into the bungalow, which was only a 1/2 block from the ocean.
I envied her as I always wanted a place at the shore. Especially at the beach. We went in and she offered me a drink.
"Lets go walk on the beach, it's a full moon tonight", she said.
"Sounds great!"
We made our way to the sand carrying our drinks with us. The moon was bright and hung low over the ocean. It was very romantic. The more I sipped on my vodka, the more buzzed I got.
