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.
Making our way over to the pilings by the boardwalk we stopped to admire the moon.
“Isn’t this so wonderful?” she asked.
“Yes, really nice” I replied.
She was wearing a tank top and short shorts and I too had on a T-shirt and shorts. Leaning against the piling she finished her drink and looked over at me.
“Do you have a boyfriend or girlfriend?”, she asked.
“Neither. Do you?”
“No, I’m gay. Guys never interested me.”
“Well, I think I’m gay too. I’ve only fallen in love with one woman and she actually broke my heart about 10 years ago”, I confessed.
“Why?”
“I don’t really know, but I think it was because she was afraid of the gay thing.
She didn’t want anyone to know that we were lovers.”, I told her.
“That’s too bad. You seem really nice.”
“I am. Her loss.”
With that she came over to me and leaned in for a kiss. I guess she felt kind of sorry for me after I told her I was trying to get over my broken heart.
Hesitantly, I kissed her back. She had the softest lips and wonderful scent about her as we kissed passionately against the boardwalk pilings.
She put her hand under my T-shirt and began feeling up my breasts. I was so
turned on by her fingers massaging my nipples that I swung her around and put both arms around her waist sliding my hands around her backside. We slid down onto the sand. There wasn’t anyone around and it was pretty dark, so we began undressing right there on the beach.
All you could see was the ocean’s waves breaking against the shore as we began to undress eachother. It was so naughty of us but so exciting to be out in the open and so turned on, that we didn’t care.
It was the first time I had had sex with anyone since my breakup with the one woman I know I truly loved. As I began to finger her vagina and kiss her passionately, I knew it was just a sex thing as I didn’t have any real feelings for this girl. She was nice and all, but I knew it was just because we were both horny and wanted to have sex on the beach. Who doesn’t”?
Afterwards we got dressed and headed back to the house. She invited me to stay over, and I told her I really didn’t have any other clothing with me.
“You won’t need any”, she teased.
“Ok. I will stay over. Thank you for the invitation. I will leave in the morning”, I told her.
When we got back to the house, she ordered a pizza and we stayed up watching Neflix on the couch. After a couple of hours, we went to bed. I stripped naked and she did the same. I was so turned on just looking at her in the light, that we couldn’t keep our hands off eachother for hours. It was really a wonderful experience with this beautiful girl and at the beach, my favorite place!
I never heard from her again, but wanted desperately so many times to look her up at the diner or at shore house. I imagine she found a forever partner and I tried to forget about her telling myself it was just a ‘fling’.
#3 – Boob Girl
It was a hot August night when I happened to get a rider in the city around 7PM.
Pulling up to an apartment building in lower Manhattan, I waited till she came down and walked over to my car.
She was in her late twenties with gorgeous black hair and green eyes. Wearing only a halter top and nylon shorts as it was extremely warm that evening. I couldn’t help but notice that she had a big smile and walked with a bounce in her step.
“Wow, it is so hot in my apartment. I don’t have air conditioning.”
“That’s too bad as it is really steamy out there”, I said as I drove away
Looking in the rear view mirror I watched as she took a hair clip from her purse and put her hair up on top of her head.
“Do you mind if I take these babies out for a little while to cool off?” she asked.
I was kind of confused at first but then realized she meant her breasts.
“Just want to cool them off for a little while in your air conditioning”, she said again wanting me to understand what she was saying.
“No problem”, was all I could respond.
I couldn’t help but wonder if I were a male driver would she have done the same thing? I don’t think so.
With that, she pulled down her halter-top and two huge boobs flopped out. Her breasts were firm and I noticed her nipples were huge and hard as they were exposed to the air. I couldn’t help but look as I started to get excited just seeing this unfold in the back seat. She placed her arms on top of her head and with her eyes closed, began to sway in the path of the cool air coming out of the vents.
It was all I could do to keep my eyes on the road and not on this hot girl in my back seat!
It was fairly dark and my windows are kind of tinted so I don’t think anyone really noticed that she was naked from the waist up. No one but me of course.
Trying hard not to over stare at this beautiful girl, I knew she was getting me all hot and bothered as my attention was on her beautiful body only inches away from me.
As we approached her destination, she pulled up her top and thanked me for allowing her to cool off while we cruised along.
“Have a good day!”, she said as she opened the door and was gone in a flash.
“You too!”, I said trying to compose myself wiggling in my seat a little as I made my way to my next pick up.