Uber Love
A Short Story
By Maryanne Peters

After being laid off from my job I started driving for Uber. I had a good car and it seemed like a way to make money, but to be honest it was more that I enjoyed the company of people and couldn’t stand being stuck at home. Even after I picked up a new job, I kept driving for Uber in the evenings.

People get into your car and some talk, some don’t. I always strike up a conversation and if people don’t want to engage, or they are on their phone and clearly devoted to that, I leave them alone. But most people are ready to talk. The way I see it, here are people you don’t know, and you never will. You get just a little bit of time and you can learn something from them, or be satisfied that they have learned something from you. It may not sound like company, but it is.

People sound off at Uber drivers sometimes. They are the same – you are a stranger they will never see again, so get it off your chest. Let me hear your opinions. If I am offended, who cares? I am just driving the car. I take it in that spirit. I am trapped, and I listen. I could give a contrary opinion, but if I do, I won’t get the rating, and my rating is good.

When I had no job my passengers were the only company I had. I was in the same job for years and I was friendly with the people I worked with, but they were not friends. After my wife left, I realized that I had nobody, but while I had that job, I just did that.

My new job is OK but I have nothing in common with my co-workers. It is strange that when you talk to a passenger in your car, you can quickly find that you have something in common, and you talk about that. Then they are gone, and that is fine. There will be another passenger. You just check your app and there is another name and another location.

I remember seeing the name “Crystal” and seeing the location – a nice restaurant on the cliffs, miles out of town. But I was closer than others, and I was up for the drive, so I accepted the job.

I pulled up outside, and I saw her. She was dressed up – maybe a little over-dressed. She was not young and she was wearing what I guess was a short cocktail dress showing off great legs. She had long blond hair and heavy makeup, but to my mind, under that, she was a pretty woman. I pulled over and she stepped in. I set off before I said anything more than confirming her name and destination.

“Your date brought you here and did not drive you home?” I said it with a smile so she could take it as she liked.

“It went badly tonight,” she said. Her voice was husky but high. It gave no clue that she was anything other than a woman – or not to me anyway.

“It’s a long way home,” I said. “To abandon you here means he’s not worth it.”

My words were supposed to comfort her, but instead, I could hear behind me that she was crying – softly sobbing and hiding her face from the rearview mirror. I suppose like most men, I had no idea about dealing with a sobbing woman. Somehow, just me and her in the car made it worse. It was a long drive.

“There’s a diner up ahead. What say I pull over and buy you a cup of coffee?” I just could not imagine driving on silently with her in that state.

“That would be nice,” she said. “I will need to fix my makeup. I must look a mess.”

“You look great,” I said. I was not flirting. She did, even with some mascara running.

I pulled over beside the diner and stepped out and opened the door for her. You always get a good rating for doing something like that.

When she stepped out I could see that she was tall – maybe just a little taller than me in those heels. I rushed to the door of the diner too. She walked inside, her hips slim, but her butt round and bouncy in that figure-hugging dress.

I ordered two coffees and two slices of cream pie.

“Maybe you’re watching your figure,” I said. “You’re in great shape. But I figure that sugar and cream are always a cure for tears.”

“You’re wonderful,” she said. “I feel better already.”

The coffee was bad, but the pie was good. We just ate and it was up to her whether she wanted to speak. I would not have been surprised if she hadn’t. It seemed to me that she was holding back - as if she had a secret that she did not want me, a total stranger, to know.

“It was just a terrible evening for me,” she said, at last opening the floodgates. “It was my first time, you see. My first time presenting as a woman. My first time out on a date with a man.”

It took me a moment to understand what she was saying. I said – “Please, I never would have guessed that you weren’t a woman.” It was not an idle compliment – it was the truth.

“You’re very kind,” she said. “Coffee, cake and now kind words. I think that you’re a special person. It’s nice to know that there are men like you around. I wish I had been on a date with you.” She smiled. It was such a pretty feminine smile that it left me doubting her sex again. Could she really be male?

“He didn’t know?” Perhaps it sounded as if I was judging her.

“I wasn’t going to deceive him,” she said. “I just wanted him to meet me, to see and to hear me. I was planning on telling him earlier than I did. It was just that things were going so well. I didn’t want to burst the bubble – his or mine.”

“I suppose that you had the protection of a crowd.” I was guilty of imagining the scene, as if it was a movie melodrama playing out in my head. There would have been the recoil in horror, the look of disgust, abusive words through gritted teeth so as not to disclose to the world that this poor fool was dining with another man in drag.

“The embarrassment of a crowd.” I stood corrected. “Perhaps I should have told him later. Perhaps earlier. The result would have been the same, I guess.”

She licked the last dob of cream off her spoon – her pink tongue between red lips seemed the very epitome of sexiness, or was it because she was such an exotic character? I had never before been close to this kind of woman - if that is the right term.

“We should get you home,” I said. “We all learn from our experiences. I guess you will.”

When she got to the car I opened the door for her in a gentlemanly fashion. Then I took my seat and drove off to the address on my phone.

“May I just say that I’m surprised that this is your first time dressed as a woman,” I said. “Your look is flawless, and your manner is perfect. Honestly, I had no idea until just now.”

“I didn’t say that it was my first time dressed as a woman,” she said. “I said it was my first time presenting as a woman in public. The truth is that I’ve been dressing as a woman as long as I can remember in private. And when I’m dressed as a woman my true manner, as you call it, emerges. It’s my behavior as a man that is a pretense. I want so much to leave it behind. I just needed to prove that I could. That was what I was doing tonight.”

“You mean you would like to live as a woman full time?” I knew a little of such things, but very little.

“I have been growing my hair, and I have been taking hormones,” she said. “But now I’m thinking that I’m wasting my time. Nobody wants a woman who is not a real woman. I don’t want to be alone in my life. I don’t want to be a freak.”

“Don’t use that word,” I scolded her. “And don’t let one bad experience make you give up. You just had a bum date – that’s all. It happens to lots of people, even beautiful women like you.”

She laughed. I looked in the rear vision mirror to see her. Her laugh was even more attractive than her smile.

“Is this your place here? Let me pull over. I will get the door.” I wanted to show her that some men were the very opposite of her date that night. I held out my hand. She swung out her legs in practiced style. They were magnificent in black patterned stockings.

It was a small unit with just a short path to her door. It was not my plan to walk her there, but I did.

“Thank you for everything tonight,” she said.

“Be sure to give me five stars,” I said.

I am not sure whether she leaned towards me, or I leaned towards her, or whether we leaned together at the same time, but in a flash we were kissing. What might have just been the merest brushing of two pairs of lips had suddenly become a fevered embrace with tongues wrestling like mating snakes.

I could hear her fumbling with her keys with her spare hand while the other held my head to her. The door opened. We tumbled in. The door closed – by my hand I think.

No words were exchanged or needed. It was a man and a woman, and she was the woman, I was never more certain of it. I would not have started taking off clothes if I had thought otherwise. The thought that sex might not be possible never crossed my mind. We would make it possible. Two people so hot for sex would find a way.

When her bra fell away, I could see the padding, but I could also see that it revealed two breasts that would have more properly belonged on a pre-teen, but with nipples standing up. I could not resist shifting my tongue to those and hearing her gasp.

“Please don’t be shocked when I slip down my panties,” she said. There was a look of genuine fear in her eyes – dilated pupils – fear and desire produce the same physical response.

The only physical response on my part was a huge erection, which she took in her hand as if it were a sacred object.

“I have been exercising and using a plug,” she said. “I can receive you.”

She turned her back to me as the panties came down, exposing her butthole and the plastic device that she was referring to. But I did not want to make love to her back.

“No, turn around,” I said. “Lie on the sofa. I want to see your face.”

I could see it, but by then, I was too aroused to care. She even slipped off the wig, but the hair underneath was soft and brown and not short. She was still the woman she was when I first saw her, but now honest and real. She removed the object and allowed me to penetrate deep inside her.

“I am an Uber driver,” I said as I drove into her, rhythmically. “I can take you anywhere you want to go.”

“Take me to heaven,” she directed.

So I did. I took us both there. And we have been there ever since.

The End

Author's Note: Please check out my blog post about my new anthology on Amazon "Heroes of Romance" which includes this story. This latest book is my 20th collection on Amazon and, like the others, it includes stories not posted online.

Erin’s seed: “A guy works as an uber driver picks up someone who looks female … The passenger breaks down in tears … They go to a coffee shop together and she confesses that this is her first time out as female and she had a horrible experience on a date. The driver takes her home and gives her some compliment, tells her to call him next time she needs a ride. They kiss …”.