The Trans Ultra Collection Vol 3

by Ursula Lovelace

  “The only thing that matters is that came at the right time,” he said, sounding dismissive of my skills as a mechanic. This was by far the most bizarre job interview I had ever experienced. Jerry didn’t seem the slightest bit interested in my qualifications. “I’m expecting business to boom over the next few months. I’m short on mechanics and I need people to fill in on short notice.”

  I smiled. “Thank you, I’ll-”

  “You’ll be hired on a probationary period,” he interrupted, lacing his fingers under his chin. I had worked under some tough managers before this guy was something else. “I’ll need to see what kind of woman you are before I make you a permanent addition to my team. You give me lip, I show you the door. Understood?”

  My smile instantly disappeared. “I understand, sir.”

  “I see you’ve got a good idea of what we do around here,” Jerry said, eyeing my outfit. It wasn’t too different from the shorts and shirt combo the workers wore here. “You’ll be given one to use while working. Keep it clean and make sure you can fit in it. Count calories if you have to. I have a brand to maintain.”

  Jerry sounded like some total pervert. He made his mechanics dress up like they were strippers or something. I wouldn’t have been surprised to learn that he tried to get playful with his employees. I’d have to keep my head down and do my work. I didn’t want this guy to put his hand inside my pants. Nevertheless, I nodded and got up to leave. “I will, sir.”

  “Not so fast, Samantha,” he snapped. “I demand complete and utter loyalty from my employees.”

  I gulped. “Loyalty?”

  Jerry chuckled. “I don’t let any girl in a short skirt work for me. I need them to see their… devotion to me before I give them a job.”

  I resisted the urge to rush out the door. “I don’t follow…”

  “There are a lot of pretty girls gunning for this job,” he continued, getting up to sit alongside me. “It’s a steady paycheck with a good benefits package. But just how far you willing to go to get it?”

  This would’ve been enough of a warning sign on its own. When you added the fact that I was a guy cross-dressing as a woman to land a job, things got a hell of a lot more complicated. I sucked in my lower lip and whispered. “Jerry, I need work…”

  The man smiled and spread his legs. I stared at his crotch as he said. “Let’s see how good you are with your hands.”

  Chapter 3

  Without the slightest bit of ceremony, Jerry unbuckled his pants and pulled out his cock. His growing erection was thicker than mine. That man wanted me to stroke and blow him in order to get this job.

  I wanted to get the hell out of here. I came here to work on cars instead of my boss’s erection. However, I was in too deep to back out now. I needed money and everything else about this job was perfect.

  It didn’t help that I was committing fraud by posing as someone else. I wouldn’t just get humiliated. Jerry could have me arrested and charged with a crime. I couldn’t risk raising any suspicion.

  Whether it was the money or role-playing as Samantha, I agreed to his terms. “I’ll do it…”

  Jerry grinned as an idiot as he gripped the base of his shaft. “Let’s what those hands of yours can do!”

  I began by gripping his cock and slowly stroking it. I had one and I knew its sweet spots. I figured it was the same for any other guy. I felt Jerry’s prick pulsate against my fingers. The man groaned in approval so I knew I was on the right track.

  On the other hand, I wasn’t sure how to do a blowjob so I decided to wing it. I started placing my lips on the soft underbelly of his cock and extending my tongue. I used the tip to lick the length of his shaft down to kiss balls.

  Jerry moaned when I began licking his balls. His prick began leaking pre-cum. I knew I had him by the pair.

  Literally.

  Finally, I went all the way to the top of his cock and swallowed it. It was briny like swallowing a mouthful of seawater. I felt his shaft throb between my cheeks. Whatever repulsion I felt at first seemed to melt away as I suckled him. It was easy to roleplay myself as Samantha who was doing this to become a mechanic.

  Likewise, Jerry sounded like he was having the time of his life. He held onto the back of my head and growled. “Oh, baby… that’s it… suck it down!”

  I felt his cock grow thick inside of my mouth. It was almost like I had an innate talent for sucking a man. I reached down to ease his balls as I licked his prick. Jerry’s eyes were shut as he submitted to my blowjob.

  I didn’t need to be an expert to know that he was going to go off at any second. I felt his prick grow stiffer and stiffer with each passing second. It was a sign that his climax was at hand.

  Suddenly, I felt a splash of semen in my mouth. It was sticky and briny. I coughed and tried to pull away but Jerry kept on top of his throbbing erection. His prick was like a machinegun with how quickly it unloaded into me. I could do nothing but swallow his hot cum.

  The more he came, the more I swallowed. I instinctually drank down every drop. It wasn’t out of fear. I was actually starting to enjoy this a little.

  Finally, Jerry finished coming and pulled out his spent erection from my mouth. He had a wide smile on his face as he told me. “What a blowjob! You’re a regular sucking machine. And those hands of yours…”

  I wiped my mouth with some Kleenex on his desk. “So, do I get the job?”

  Jerry chuckled as he answered. “You’ve earned it. Oh, that worry about that probationary period thing. You’re a full hire with all the benefits.”

  I lit up at that. Even if this had been the most bizarre interview process of my life, things were starting to look up for me. “Really?”

  “You’ll fit right in with my crew,” Jerry said, leaning forward. He placed a hand on my arm and caressed it with his fingers. I resisted the urge to recoil back in discomfort. “You can make good money working under the hood but you can make a lot more in my office. Don’t be afraid to stop by from time to time if you want to earn a bonus. Some extra cash in your pocket sounds nice, doesn’t it?”

  As much as I enjoyed it, I didn’t look forward to blowing Jerry on a daily basis. Nevertheless, I needed to sound appreciative of my new boss. “I’ll keep that in mind.”

  I pulled my arm away as Jerry said. “Run along now, Samantha. I expect to see your curves in our uniform tomorrow.”

  With the interview over, I went to get briefed by the other mechanics. I thought they suspected what had happened between Jerry and me in that office. Thankfully, they didn’t ask any questions about it. I was beginning to guess that this was normal in a place like this.

  The garage management was supposed to teach me the ropes but they learned that I was a quick study. I probably knew more about cars than anyone else in here. Hell, I didn’t think Jerry had ever fixed a car in his life.

  What was more interesting was the garage’s uniform. It was a pair of trimmed shorts with a tight shirt. The outfit was much more form fitting than the one I wore. It also left quite a bit of skin exposed which was strange in this line of work. I guessed it was a good enough marketing gimmick. Jerry’s Shop got plenty of customers.

  While the garage’s owner may have been a jerk, all the other girls were nice enough. I conjured up a fake story about how I was taking online classes at an out-of-state university. They seemed to buy my cover story as long as I put in the work at the garage.

  None of them seemed to know that I was actually a man. I expected an idiot like Jerry to be fooled but I was more nervous about being around women. It was an unfounded fear since they remarked that I was one of the prettiest girls on staff. It seemed as though they were just as impressed with my looks as they were with my skills as a mechanic.

  I couldn’t believe I had pulled off such a crazy stunt. My plan hadn’t involved blowing off the garage’s owner but I got the job. Now, I just had to keep my cover and let the paychecks come home.

  There was still the issue of sucking Jerry’s cock fo
r some extra income. Although I enjoyed it more than I would’ve liked, I wasn’t keen on being around my new boss if I could help it. The guy was a total sleaze. Hopefully, he would leave me alone and allow me to do my work in peace. I would be bringing him a lot of money with my talent for car repair.

  Besides, a guy like Jerry would make me do all kinds of wild stuff. If he tried to forcibly take my clothes off, then he could discover that I was actually a man. An ego-manic like him would have me arrested on the spot. It was better for me to avoid him and focus on my work.

  It was strange to think of Samantha as a mere disguise. She felt more like a person onto herself. My alter ego had a personality that was different than mine. She also didn’t mind sucking cock either. There was a certain thrill to hiding in plain sight as a beautiful woman.

  Regardless of my thoughts on Samantha, I knew I had to focus on being the best mechanic I could be. If I wanted to resist Jerry’s unwanted sexual attention, then I had to make myself an indispensable employee. Within a few days, I managed to be the certain of attention for both my looks and my skills.

  It helped that customers weren’t above giving the beautiful staff a few gifts as a show of thanks. While the basic salary was adequate, the customers were a real cash cow. I got expensive presents ranging from gift cards to gold band watches. The net worth of all these gifts was over a thousand dollars. I was making more money working as Samantha than I ever did as Simon.

  The attention I was attracting at work made me feel more like a celebrity than a mechanic. It had only been a few days since I had been unemployed and desperate for work. It helped that the customers were civil to me when I was trying to diagnose their cars for problems. The average customer was likely to think that you trying to cheat them when in actuality you were giving them a good deal. I never got into an argument while working as Samantha.

  Week after week, I made a reputation for myself as the best mechanic around. People from all over the state came to Jerry’s Shop to have their car looked over by me. Of course, men were interested in for more than just my car repair expertise.

  I got asked out on a date more times than I could’ve counted. I was started to suspect that men were sabotaging their cars just to get in a room with me. Of course, their plans for me were more intimate than I was comfortable with. I always had to let them down gently.

  Well, not all of them.

  There was one guy who brought his Audi in every few weeks for a tune up. I didn’t know too much about him other than that all the other girls at Jerry’s Shop fawned over him. I couldn’t blame them. This guy was young, tall, and quite handsome.

  “Samantha, can you tell me what’s wrong?” he asked, leaning against his car. I appreciated that he was polite while not being overbearing. “The steering’s gotten stiff over the past month.”

  “Nothing wrong with this beauty,” I said, closing the hood of the car. The man kept his car in much better shape than most of the other customers. I suspected that he was pretty handy with a monkey wrench too. I knew he was more interested in me than the services I provided. “I just needed to adjust the power steering fluid. Everything else is fine.”

  He nodded. “Thanks, my name’s David by the way,”

  “You have a nice ride,” I replied, eyeing his Audi. We got some nice cars through the garage but David kept his ride in pretty good condition. “What do you do for a living? Stockbroking?”

  David laughed. “No, I work for the IRS. I don’t go around telling people that since I just get angry looks!”

  I laughed as well. “I can’t blame you.”

  “Maybe you can give me some car advice over dinner,” he offered. The man wasn’t that much older than me but had a sense of maturity about him. It was a breath of fresh air after dealing with Jerry and annoying customers. “I know a great place in the city.”

  I wished it was that easy. “I’ll think about it…”

  It was hard watching David drive off in his Audi. He seemed like a swell guy. I knew I couldn’t have a romantic relationship with a guy like him. I was a man dressing up as a woman to land a job. For that matter, I didn’t know why I was even having feelings for another man in the first place.

  Chapter 4

  I had a good thing going with Samantha. I was making more money than I knew what to do with. I couldn’t risk all that I had accomplished just to get close with a customer. On the other hand, I had to deal with a more persistent man at work.

  Jerry.

  I was dead set against going to his office and blowing him. It wasn’t the act itself that bothered me. A man like Jerry would want more than oral sex. He could get frisky with me and discover what I was hiding in my panties.

  Normally, I would’ve felt pressure to give into his demands. The man was my boss and could cut me loose at any time. However, I had quite a reputation at the garage. I wasn’t just well-known for my looks. I was also the best damn mechanic Jerry had.

  If I left, then he was likely to lose a deal of business. A rival business could pick up the slack. Jerry decided to live and let live as long as I brought in money. It wasn’t like I was desperate for money anymore.

  Despite this, I couldn’t help but think of myself as Samantha first and Simon second. It made sense once you thought about. I was spending more time as her than as myself. It wasn’t just for the money either. I was starting to think of her life and personality as mine.

  This included her sexuality.

  I didn’t know why but I was starting to develop a thing for guys. Something about being a woman all the time had made me start liking guys. Just thinking about being with a man made me hard.

  As Simon, I had never given my romantic life much thought. Every day was a struggle to make ends meet so I could pay the bills. I never had much time for dating. My family joked that I preferred radiator grills to girls.

  I was much happier being Samantha than as Simon. People were kind and respectful towards her. I never had to deal with angry customers at work. It sure beat getting into a shouting match over a simple oil change.

  It was why I liked working with David. He loved to stop by at the shop for some advice about his car. I suspected that he just wanted to talk with me.

  It was strange not having to worry about money. It was just so easy to make money off tips and gifts from my customers. Well, that wasn’t entirely true.

  I was working under the table at Jerry’s Shop. It would attract a lot of attention if I went on a spending spree as Simon. It wasn’t exactly easy to tell people that I was cross-dressing as a woman to get work as a car mechanic.

  I wasn’t sure how to report the money come tax season either. I figured I could ask David for some advice since he worked for the IRS. It was only fair after how much advice I had given him about cars.

  Speaking of him, I got to know my favorite customer even better. David was head of a local IRS branch in a nearby city. He tended to drive his car a lot for work. It explained why he came in periodically to do checkups and tune ups.

  It was no secret that the other girls at Jerry’s Shop were attracted to him. The man looked like a movie star with a tall, athletic body. It was just as well built as any sports car. I couldn’t help but feel the same way about him.

  It was strange being Samantha. She felt more real than the lifetime I had spent as Simon. I didn’t stop being her when I came home after a day of work. I still wore her clothes and makeup while I watched TV or made dinner. It was what scared me the most about being caught cross-dressing. I would never be able to continue being her.

  Regardless, I got closer to David over the next few weeks. I wanted some tax advice. He wanted some car advice. Well, he wanted more than just that from me.

  “Samantha, are you free this weekend?” David asked me one day. I was surprised he was being so straightforward. Typically, he was more subtle about asking me out. Then again, I kept letting him down gently. “I know you got work off. Maybe we could go somewhere special in the city.”

>   I bit my lower lip. “That sounds like a date…”

  “It is a date,” he replied with a laugh. “And I know you don’t have a boyfriend. So how about it, Samantha?”

  That left me a bit of a dilemma. I genuinely liked David’s company. He made a busy day at the shop feel like it passed by in a second. However, I ran the risk of him finding out the truth about Samantha. I didn’t know how he would react. He could easily go to Jerry and have me arrested.

  I let my gut make the choice.

  “Sure, David,” I said, surprising him. Hell, I surprised even myself. I was putting myself in a lot of danger for a romantic date. Then again, I owed David one for giving me some financial advice. If we couldn’t date, then at least we could be good friends. “I just don’t want to lead you on or anything. This job comes first before anything else.”