The Trans Ultra Collection Vol 1

by Ursula Lovelace

  “I know staying with me is an inconvenience,” Charles said. “But I’ll make it worth your while… considerably.”

  I smiled at his generosity. Besides, I wanted to stretch and relax after a long month of work. “You’re the boss. I’ll take it easy since I’m the one driving!”

  We chatted for the next ten minutes until we reached our destination. I parked the car in the bar’s parking lot. Charles deftly got us through the long line and onto his reserved table.

  In my new outfit, I didn’t look too out of place in the luxurious setting. It was truly gorgeous. This place wasn’t some pub you would find in a hole in the wall. Instead, everything looked handcrafted from top to bottom. The ceilings were high and the rooms were elegantly furnished. Our table was handcrafted with several fancy paintings overlooking us.

  The place was too rich for someone used to drinking light beers at a sports bar. Then again, I was Tommy now. She was a sophisticated woman if the backstory I had made for her was the slightest bit true.

  After we placed our orders, Charles and I made some small talk. He told me he had a problem with wanderlust. The man always wanted to experience new things. It was why he loved traveling across the country through his job as an executive. Nonetheless, he enjoyed his time in this city.

  I couldn’t help but notice how handsome he looked. I never thought men that way until now. Perhaps, I was just jealous of how attractive and sophisticated he was compared to me. Most of the women at the bar were eyeing him with erotic intent.

  That’s when I realized they were also looking at me with jealousy. Having dressed up, I could be mistaken as Charles’s date. I couldn’t help but feel a little smug at the thought.

  Even Charles honed in on the idea. “Don’t mind them. I much prefer being with you than a stuck-up woman.”

  My mind reeled at the thought of being seen as Charles’s girlfriend. Tommy had begun as a way for me to get a bigger payout as an Uber driver. Now, she seemed like her own person. People loved talking to her and getting to know her. Other women were dead jealous of her. It was getting a bit out of hand. Nevertheless, I told Charles. “I’ve never been to a fancy bar like this. I usually visit the local sports bar and watch the big game with the rest of the plebs.”

  “You’ll have a great time here,” he assured, giving me a half smile. “The menu here is to die for. It’s why I chose to share it with you.”

  “How long do you plan to stay here?” I asked. A server arrived to deliver our drinks before heading out to another table. “I know that you’re just here on business.”

  “Two weeks,” Charles sighed, leaning back on his chair. He didn’t seem eager to leave this city. “I’m asking my employer for an extension. I just love this city, especially the new people I’ve met…”

  I smiled. “I hope you get that extension.”

  He reached across the table to put his hand on mine. “As do I.”

  I felt my cock harden at his touch. I didn’t know why my body was reacting this way. I chalked it off to just nerves. I tried to look as stoic as possible. “Give me a buzz if you’re still in the city. I can give you a ride anytime.”

  Charles retracted his hand. I immediately missed the feel of his skin on mine. “I’m sure you have so many customers waiting to hitch a ride with you.”

  The man looked questionably at me. I avoided his piercing gaze. “My job would be easy if every passenger was like you.”

  “You’re not like most other women, Tommy.”

  My heart raced. The head of my cock formed a tent in my panties. I wondered if he had seen through my disguise. “Ha-ha… what makes you say that?”

  He smiled. “Most women would’ve given into my charms by now.”

  “I respect you too much,” I giggled, calming down. “I don’t like mixing business with pleasure. I wouldn’t want to lose such a model customer. I got to pay the bills after all!”

  Charles wasn’t letting me go so easily. “Is there a man in your life, Tommy?”

  Before I could answer, our waitress arrived and served us drinks. “Sorry to keep you waiting. This cocktail takes quite a bit of time to make. Your next order is one the house. Please forgive us for the delay.”

  “The service here sure beats the old sports bar!” I laughed as the waitress left. Then, I shared a look with Charles. “I’ll stick to the soft stuff for now.”

  He looked at my glass of soda. “You sure you don’t want anything harder, Tommy?”

  I took a sip of my sugary drink. “Can’t drink on the job. I got to get both of us home in one piece.”

  More importantly, I didn’t want to risk getting drunk off my ass and admitting that I was a serial cross-dresser.

  The two of us bonded over the drinks. I didn’t believe how an average guy like me got along so well with Charles. Then again, I was Tommy now. She was a well-cultured, classy woman. Well, as classy as an Uber driver could be.

  Nonetheless, I learned that Charles was single. His work and travel prevented him from starting long-term relationships with anyone. The man could have any woman he wanted between his good looks and charming personality. He could certainly drink with the best of them with the way he went through the drink menu.

  Charles finally cajoled me into sipping a glass of wine. He ordered an expensive looking bottle of wine for us to share. We toasted each other as I tried to stomach the strong wine.

  While Charles ordered another bottle for himself, I talked about my life as a driver. I told him about the people I had met and the places I had visited. I also mentioned that he was by far the nicest, most interesting man I had ever met.

  In turn, I learned that Charles was a creative director at his art company. He went around the world meeting clients. He had humble beginnings growing up in a rundown neighborhood. It explained why he felt so much more approachable than most of the rick folk I had encountered in this line of work.

  I didn’t know whether it was the atmosphere or my lack of constitution but I couldn’t help but get a little frisky with Charles. Sitting next to him, I spread my legs so that the edge of my panties could be seen past the short skirt of my dress. My erection was hidden under the gusset but I still showed quite a bit of skin. Then, I raised my skirt and exposed more of my thighs.

  Charles wasn’t blind. He noticed what I was doing and his hand found its way on my leg. His fingers trailed upwards until they reached the inside of my thigh. As risky as it was, I wanted to him to feel the bump on my crotch. However, he was content to trail his finger up and down my thigh before grabbing fistfuls of my skin.

  I was so aroused from the sheer audacity of what I was doing. Here I was, a man cross-dressing as a woman, on what was practically a date with a handsome business executive. The man was clearly attracted to me from the way he caressed me.

  Charles caressed me for what seemed like hours. No one seemed to know what we were doing under the table. It was exciting to do in a public place, especially while dressing as a woman.

  I would’ve came in my pants if not for sheer willpower. I had never been so aroused before in my life. Strangest of all, it was another man doing it for me. However, I couldn’t risk getting caught, especially in these circumstances. Thankfully, Charles stopped when a waitress came over to order

  A moment later, we got our drinks. Charles handed it to me. “Here you go.”

  Our fingers briefly touched and I felt a surge of erotic energy. My prick was painfully stiff in the soft fabric of my panties. Tonight had been the wildest thing I had ever done in my life. “Thanks…”

  Charles looked at me with desire in his eyes. “Anything for you.”

  Again, I sensed his hand travel towards me. It rested upon my knee before moving alongside the interior of my thigh. I gasped when his finger traced the edge of my panties. I prayed that he would not go under the band and discover what I was really keeping under it.

  It was so reckless, dangerous, and audacious. I just couldn’t help but give into his teasing.
All of my anxiety melted away as Charles touched me. I felt like an integral part of his life rather than some driver he had hired through the Uber app.

  For better or for worse, it came to an end as another round of drinks arrived. With it came another round of conversation. Charles took a hold of my hand again. “Tommy, you’ve been an absolute delight tonight. I can’t recall the last time I’ve had so much fun. I was lucky to have chosen you as my driver.”

  “Why pick me?” I asked, genuinely curious. I had many customers ask me out on a date. However, none were as persistent or charming as Charles. Or frisky for that matter. “I mean, there are better drivers with fancier cars than me. Sure, I get good reviews but you could easily hire a fleet of limousines.”

  “It was your photo,” he answered, sending a shiver down my spine. “You stood out from the rest. There’s something special about you, Tommy. I can’t put my finger on it. Nonetheless, it was a good choice since you’ve treated me so well tonight!”

  “That makes two of us,” I giggled, trying to shift the subject. “I feel like I’m being treated like royalty here. I can’t say the last time I had so much fun… or acted so wild in public!”

  “The pleasure is all mine,” Charles replied. “I’ve had such a wonderful time with you. Yet, I don’t want this to end so quickly.”

  I raised an eyebrow. “What do you mean, Charles?”

  “There’s something special about you,” Charles said, staring at me with his beautiful eyes. I was too distracted by his looks to be afraid of his probing words. “I just can’t put my finger on it.”

  I laughed in spite of my nervousness. “Maybe it’s that I’m a female Uber driver? How many of those are out there in the city? We’re like rare unicorns.”

  “Aside from that,” Charles chuckled, placing his hand over mine. His touch was absolutely electric. “It’s been a very special night for me. Normally, I don’t get too close to people and do something like this.”

  “How come?”

  “I’m usually gone the next week,” he explained. “I try not to get too attached to places or people. Of course, I’ve made an exception for you.”

  “I don’t suppose it’s the alcohol,” I said with a shrug. “I’ve never done something so crazy before in my life.”

  He looked at me with a glint in his eye. “The night’s still young, Tommy.”

  “Well, I’ve enjoyed sharing this night with you,” I replied, glancing away. A part of me wanted to leave before he found out the truth. The other half of me wanted to jump this sexy guy. “This is the most fun I’ve ever had on the job.”

  “Perhaps, this night doesn’t have to end so early,” Charles stated, looking at me with desire in his eyes. “It’s awfully lonely in my penthouse suite. I wouldn’t mind some company.”

  I couldn’t believe what I was hearing. “Is that an invitation?”

  Charles nodded. “I’ve booked you for the night. I can pay more and make it worth your while.”

  This was getting a bit out of hand. At the same time, I didn’t want to leave so suddenly if he was already suspicious about me. It would look too strange. I figured I could be polite and have a drink at his place before taking my leave. “What do you have in mind?”

  “Perhaps another round of drinking at my place,” Charles teased. His voice was low as if to avoid being overheard. “You haven’t had anything too hard here. Come to my place and we’ll fix that. I’m sure room service would accommodate us.”

  “Sounds almost like a date,” I whispered back, unsure of his intentions. The man seemed genuinely attracted to me. He was going to be in for one hell of a surprise. Then again, I wasn’t sure how to get out of this offer without upsetting him. I was developing a soft spot for Charles. “And you just met me today.”

  He held in his head in mock grief. “I must be losing my touch. Most women fall head over heels when I ask them to come home.”

  “Oh, it’s not that,” I said, trying to humor him. It didn’t seem he was going to let me off so easily. It was probably best if I played along for now. At the very least, I didn’t want to get a bad review on Tommy’s sterling record. “It’s just that I like to keep my work relationships purely professional.”

  Charles leaned closer over the table. “What about when you punch out for the day? Besides, I’ll be sure to leave a glowing review.”

  I couldn’t help but blush. “You got me. I can’t refuse such a generous offer.”

  As strange as it was, a part of me was attracted to Charles. I never thought of men in this way. Now, I was mentally undressing him.

  More than that, I imagined us making love. I wanted him to suck my nipples as he thrust into me with all of his strength. I wanted to feel his balls slapping against mine as we he took me from behind. He would do all kinds of things with his hands while fucking me.

  I didn’t know why I was experiencing such wild emotions. Something about cross-dressing and becoming Tommy had emboldened me. She seemed like another person altogether. Tom, the boring male Uber driver, was just along for the ride.

  Charles read my mind. “Are you imagining the romantic night we’ll soon have at my suite?”

  I didn’t blush this time. “I can imagine that and then some.”

  “Then it’s settled,” Charles said. He lifted his hand and caught the attention of a nearby server. “Check please.”

  I was nervous as hell when I drove us back to Charles’s hotel. It wasn’t from the alcohol. The mouthwash I had used in the morning probably had more alcohol than whatever little I had drank. Instead, I was drunk on lust as well as the danger that came getting so close to him.

  At the same time, I knew I was taking a big risk getting so chummy with Charles. The man had a way of getting me to lower my guard. I hoped he didn’t plan on getting naughty with me tonight. It had already been a crazy night to begin with.

  And it didn’t seem like it would end anytime soon.

  I entered the driveway of his hotel and circled around to enter private parking lot. The night was surprisingly quiet with more trees and lights than people. Ever the helpful Uber driver turned chauffeur, I walked to the backdoor and opened it. “Right this way, sir.”

  Charles chuckled and flashed me a smile. “Believe me, I’ve seen worse service from luxury taxi drivers. Shall we head to our room?”

  I blushed. “Our room?”

  The many was seriously hitting on me. I wondered how far we could go. He could touch and kiss me. Anything further would reveal my secret. I wouldn’t just be humiliated. I could lose my lucrative career as one of the top Uber drivers in the city.

  As they said, in for a penny in for a pound. I didn’t want to disappoint Charles after all he had done for me. I just had to think of an elegant exit when things got too hot.

  I followed Charles into his high-class hotel. I didn’t bother to take in the luxury of the building. My heart thundered as I followed this strange yet alluring man. I felt exposed as if all of my sexual desire was laid bare in some courthouse. I just didn’t know whether this was from Tom or Tommy.

  Charles walked hand in hand with me. Every so often, he would give me a soft smile. No man had the right to be that handsome. It was so disarming that I jolted up from my daydreaming when I heard his keycard unlock the door.

  I wanted to say my goodbyes and chicken out of this. This scenario was a powder keg. My disguise had held up so far but it couldn’t withstand so much close scrutiny. He could find out who I really was.

  However, my desire overcame any inhibitions I had left in me. Charles had the uncanny ability to stir the primal instinct within me. It felt as though I couldn’t stop my alter ego Tommy’s desire for him.

  She was in charge now.

  It would be an understatement to say I was going above and beyond the typical services provided by your neighborhood friendly Uber driver. With my heart thundering against my ribcage, I followed him inside.

  It took me awhile to gather my thoughts. I tried to rati
onalize this as just my natural friendliness to all of my passengers. However, I couldn’t believe that myself. After all, we had touched each other intimately at the bar.

  The hotel suite was as beautiful as I had imagined it to be. The balcony had a beautiful view that I gravitated to. I took a breath of fresh air as Charles walked up next to me. Together, we stood and basked in the moonlight. Glancing over my back, I saw that Charles had already prepared some champagne for us to drink.

  Finally, Charles broke the silence. “Care for a drink in the bedroom?”

  I nodded. “Sure…”

  The two of us walked into the bedroom. It had regal red carpeting that gave the room an erotic if aristocratic flair. I sat on the king-sized bed as Charles sat in a nearby armless chair. With a smile on his lips, he poured two glasses and handed one to me. “Cheers.”