The Trans Ultra Collection Vol 1

by Ursula Lovelace

  Eventually, we broke apart. I looked at Jack with desire apparent in my eyes. “It’s time for you to fuck me…”

  Jack entered my ass with a loud groan. He was bigger and thicker than any man I had before. He made love to me as if we had been together for years. He pumped into me faster and faster as I held onto his powerful frame for dear life. I shuddered as our mutual orgasm began. I closed my eyes and let out a loud moan with each of his thrusts. “Ah! Ah! Ah! Aiii!”

  Jack couldn’t hold back either. He came loudly and powerfully inside of me. All the while, he pumped into me as the hot cum spilled out of his shaft. Only the soft kisses we shared tempered the intensity of our orgasms. I stared at him wildly as the aftershocks of climax reverberated throughout my body.

  My cock grew hard and spurted its load. My hot cum stained the bedding. I went on and on until my strength left me.

  We were in love with each other. I wanted to live with this man forever. I was slave who had been just granted freedom. He was a killer seeking redemption through a woman who he had once hurt. He had no right to have my love or forgiveness… but he had both. However, I knew our love could not be. The world he lived in was too dangerous for me to live in.

  Yet, it didn’t matter who we were tonight. We were just a man and a woman holding onto hope. Jack held onto me as he caressed my satisfied body. Soon, sleep overtook our spent bodies.

  For the first time in what felt forever, I felt happy to be in the arms of a man. I didn’t know what tomorrow would bring. However, I knew we would do it together.

  For those not in the know, Uber is a transportation service where anyone can become a driver. You just needed a car and a phone to become a driver or request transportation. Drivers like me delivered everything from people to pizzas.

  After each drive, passengers rated their drivers from one to five stars. If you received a poor score, it would negatively impact your overall rating and that specific passenger would never be paired without ever again. I was rated four out of five stars. It wasn’t a terrible rating but it wasn’t the best in a highly competitive city. Uber drivers lived and died by their rating.

  The whole thing was a bit in the grey market but that was for the politicians to decide. It was a fast evolving technology so governments were slow to regulate it. I just wanted to make hay while the sun was still shining. Nonetheless, I just wished the sun shined brighter above me.

  Working as an Uber driver, I always heard that female drivers were tipped better than men. Their passengers were nicer than the usual troublemakers you attracted. They also gave female drivers better reviews. Hell, passengers even took photos with their drivers and posted it on social media. I wouldn’t know since I was a man named Tom instead of a woman named Tommy.

  As someone who had been working part-time for nearly a year, it never made much sense to me. My customers were all looking to save money. It was why people used a taxi service like Uber in the first place. Perhaps, women attracted a different kind of clientele.

  Female Uber drivers were a rare sight around these parts. However, I did know a few since the Uber community here was close-knit. We shared all kinds of secrets and anecdotes about our work.

  These women were much better off than a guy like me. They told me that they had made a small fortune working as drivers. Their passengers were nicer than the usual riff-raff and even gave them expensive gifts. Some of the women had even quit their day jobs to work full-time.

  I couldn’t help but feel envious of their success. In my experience, the job didn’t pay much but it helped supplement my income as a call-center worker. I was happy to get out of the office and meet new people more than anything else. The extra paycheck was just a bonus.

  You see, I loved encountering new people through this part-time job. They always had stories to tell and interesting places to go to. It helped me deal with the grind of ferrying people from one place to another in the fastest, most convenient route possible.

  As for my car, it was a creaky sedan that had seen better days. Nonetheless, I was a good driver and had positive reviews from my customers. I just needed that elusive five star rating before I truly made it big time.

  However, I just wasn’t attracting the level of business I wanted. I had to depend on tips beyond the usual fare to make up for gas and car repairs. Doing the math, I was barely making out a small profit.

  I was already working hard as it was. Instead of partying on the weekend, I drove others to parties. This whole gig had really killed my social life. Let’s not even talk about my romantic life.

  I had heard that female drivers didn’t have to work as much to make big bucks. I knew a woman who only drove on weekends and was making money hand over fist. It made me feel quite jealous of her success.

  Strange as it was, people tended to mistake me for a woman at a glance. I always had a lean, girlish figure. It always made me feel self-conscious.

  It was why I decided to work in a call center. I never liked front facing jobs until I became an Uber driver. If you put a wig on me, then maybe I could pass as a woman.

  Hell, I even had a naturally high pitched voice. If I moved it over a few octaves, I could talk like one of my sisters. Speaking in a falsetto never failed to entertain some of my passengers.

  That’s when I had a crazy idea.

  I could dress up as a woman and drive people around. If the stories I heard were true, then I could double my income! I could use the same car with a new identity. Tom might haven struck out but Tommy would be up at the plate.

  I’d just need a disguise and a new Uber account. It would be easy to acquire both. If I used my real name, then all the money would go to Tom as far as their accountants were concerned. It didn’t matter if it was a man or a woman as long as the name and address was correct.

  Technically, it was illegal to pull a stunt like this. However, the registration process for a new Uber account was lax enough. The bigger worry was having a passenger see through the disguise and lodge a complaint. I could lose my Uber account or even go to jail!

  Nonetheless, the idea took a hold of me like some spell. I went to work making the preparations. I bought women’s clothing and created a new account for a woman named Tommy.

  I was surprised at how easy it was to dress up as a woman. I thought it would be awkward like playing dress up as a little kid with your parent’s oversized clothing. Instead, I found that the fabrics were soft and form-fitting. Going back to wearing my office clothes for my day job was a pain.

  It helped that the feminine clothing looked good on me. It fit my body in a way most men’s clothing didn’t. My old clothing was heavy as if I were bundling myself up for the winter. A large wig finished my new look.

  Going a step further, I bought a set of bras to give myself some semblance of a bust. I padded it out to give myself a respectable bust line. It helped the whole get-up look believable.

  The hard part was makeup. I couldn’t exactly ask my sisters for help or go to a beauty parlor. I had to look up a Youtube video to find out how to do my nails or put on mascara. After a few trials, I managed to get the hang of putting on everything from lipstick to eye shadow.

  Then, I went to on to practice my speaking voice. I had already done it enough as a charade that I was well-versed in it now. I actually felt more comfortable speaking as a woman than as a man.

  Soon, the transformation was complete. None of my friends or family would’ve believed I was actually Tom. More than that, I felt so much in love with my new look. I never thought of myself as beautiful but Tommy certainly fit the bill.

  However, my new persona was not battle tested. If someone saw through it, then they could press charges. I could lose my Uber license and be ostracized.

  Finally, it came to put Tommy to the test.

  I made my profile, uploaded a good profile photo, and waited for the customers to request me. To my surprise, I got a flood of requests within minutes. Typically, Uber drivers without any reviews had a hard time
getting work. Some of them had to work below the market rate to get work.

  I guessed they liked my profile photo.

  To my surprise and glee, none of my new passengers suspected that I was a man. They were friendly with my new persona. More importantly, they all tipped well. I made more in one day as Tommy than in two weeks as Tom.

  The passengers were also much more talkative with me. I often had to make up a backstory to keep them entertained. I told them Tommy was a part time model who masqueraded as an Uber driver on her nights off. The story kept them interested in me.

  Many of the men even asked for my personal number. However, I couldn’t risk getting close with any of them. They would just find out who I really was and the whole charade would fall apart.

  As a man I had been fairly unremarkable. As a woman, I couldn’t keep these guys from hitting on me. It didn’t help that many of them ogled me while their wives and girlfriends were sitting beside them.

  Many of the women were jealous of me. I didn’t know why when several of them were beautiful enough to be supermodels. I guessed I just had this natural charm that worked its magic on men.

  Over time, I began taking in richer and richer clients. That’s what happened when you got five star reviews all the time. They were better dressed and groomed than my usual clientele. I even had to drive to the nicer part of the city to pick them up.

  My beat-up car felt a little out of place in their wealthy neighborhoods. So I decided to lease a new car. I could afford it now that I wasn’t poor and living on macaroni and cheese. It wasn’t a fancy sports car but it was an upgrade from my old sedan. More importantly, its license plate couldn’t be easily traced back to Tom.

  I didn’t know why these rich people used Uber. I figured they would have nice limousines services on speed dial. I guessed the convenience of getting from Point A to Point B on short notice beat having a hot tub inside the car.

  These passengers wore expensive jewelry and visited ritzy restaurants. The clothes on the women were out of this world. On the plus side, they also tipped well. All thanks to my rich benefactors, I could quit my horrible day job at the call center.

  By now, I had great reviews and feedback from my customers. While I rarely had conversations beyond the usual pleasantries as Tom, I found myself constantly speaking to people as Tommy. They wanted to know everything about me.

  One day, I decided to put some extra effort in my appearance. I was inspired by the rich women I ferried across the city each day. I focused on my hair and makeup so that they looked immaculate. I had a strong claim to being the sexiest Uber driver in the state.

  With my newfound wealth, I purchased a new set of clothing. It was a stylish dress that looked nice while allowing me to drive comfortable. Underneath, I treated myself to a set of designer lingerie. I had ordered them from a reputable shop in France and had them shipped to me overnight.

  The new undergarments were a delight. The skimpy panties fit nicely against my backside. The crotch section was big enough to hide my cock. Likewise, the bra worked well with my padding to give me an impressive cup-size. Of course, it wasn’t like anyone else was going to see them.

  In all modesty, I looked like a knockout. My low-cut dress revealed much of my skin. My new designer heels pumped up my height. I had even tied my wig into an elegant bun with a ribbon. I finished the look with a pearl necklace I had recently splurged on.

  With my persona being in-demand, I could be picky about the people I drove around. I preferred driving people around in the nicer part of the city. It didn’t matter if they had a lot of money or not. I just liked a nice, relaxing drive across freshly paved streets with beautiful scenery.

  I pulled up before a fancy hotel. I never got tired of marveling at such opulence. It was a funny feeling since I had been dirt poor a few months ago. Despite my new wealth, I knew where I came from.

  Looking down at my phone, I examined the request. My client was a well-to-do traveling businessman named Charles. Well, that’s the impression I got from our brief phone call. He seemed like a nice enough man.

  Charles had booked me for the entire evening. Rather than rely on someone else, he wanted me as his designated driver for the night. The man probably planned on drinking heavily. It wasn’t too unusual but only someone with a lot of money would go through this much effort.

  I didn’t have to wait long before Charles made his stylish entrance out of the hotel doors. The man was tall, dark, and handsome as they came. I could make out his muscles from under his custom tailored suit. The man’s features were chiseled like a male model. However, it was his piercing blue eyes that struck me from the distance.

  I didn’t know much about Charles other than I knew I liked him. Some of the rich men I drove could be a bit snobbish. They thought of me as some sexy chauffeur they could order around like a servant. Charles, however, insisted that we speak on a first name basis with each other during our phone conversation.

  Over the phone, I had learned that he was touring the country due to his job. He had asked what I liked to do and what places I’d liked to visit. It didn’t matter that his tax bracket was in a different stratosphere than mine. Charles was still interested in my answers. Nonetheless, I still directed him towards the typical ritzy places my richer passengers visited.

  “It’s good to see you in person, Tommy,” Charles said, kissing my hand before returning to the passenger’s side of the car. I couldn’t help but blush at the gesture. “No bags for me, tonight, my dear. I’ll be traveling light.”

  I looked up as the man towered over me. His presence alone sent my heart racing. “Okay, Mr.-”

  “Please, call me Charles,” he insisted with a soft smile. The man took a seat in the back. “I only allow my business partners to call me that. You and I are friends for the night.”

  I chuckled. “I’m just your driver for the night. I can stay out of sight and mind if need be.”

  “No, we don’t have to be so formal with each other,” he said, his teeth shining through a brilliant smile. “I insist that you join me for a drink and a meal tonight. I never liked drinking alone.”

  I raised an eyebrow at that request.

  As close as I had gotten with some passengers, none of them had offered to take me out to a fancy dinner. Sure, I had requests for dates but nothing like this. I wasn’t sure I wanted to cross that line considering I was cross-dressing. Then again, I didn’t mind being treated to a free meal from such a classy guy.

  I decided not to refuse. My payment had a lot to do with my customer’s satisfaction. There were a lot worse ways to earn money than being treated to a nice dinner. “Dinner sounds delightful. I hope it doesn’t inconvenience you.”

  Charles chuckled. “Believe me, it’s better than eating alone.”

  “Well, you’re the boss,” I replied sheepishly, looking into the rearview mirror. “I’ll make sure to get you to your destination on time, Charles.”

  I started to drive to the bar in which Charles had reserved a table beforehand. It was a fancy one that allowed you to taste a variety of alcoholic beverages along with some classy finger foods. It was like an eight course meal for liquor lovers. The two of us would even have our private table and personal bartender. As the designated driver, I guessed I’d have to only have non-alcoholic beverages.

  I had been cross-dressing long enough to feel comfortable as Tommy. Yet, something about Charles made me feel nervous. He was smarter and more perceptive than the usual passenger. Indeed, he noticed my discomfort. “Tommy, are you okay? I hope you haven’t been working too hard.”

  “I’m just not used to being treated to a night out,” I answered truthfully. I was just too jittery to tell a lie. “Don’t worry, I’ll get you back home in one piece.”

  Charles replied. “I heard you’re a popular driver in these parts. It must be why you’re tired.”

  Waiting at a red light, I shrugged. “I just do my best.”

  “You’re certainly a good source o
f conversation,” he laughed. “I’m glad I’ll have your company at the bar.”

  “Why do you want me to have a drink with you?” I asked, genuinely curious. “Isn’t this your big night out? Why ask some Uber driver you hired out of the blue to join you?”

  He gave me a boyish grin. “I don’t like drinking alone. I like to share my experiences with other people. Besides, you’ve already dressed for the occasion.”

  I glanced at my reflection in the mirror and giggled. “That’s true. I try to keep up with my clients when it comes to fashion.”

  “I take it that most of your passengers don’t invite you to join them,” he continued. “What do you do in the mean time?”

  “I usually find other work to do in between dropping off and picking up people.”