“I understand,” he replied, his eyes lighting up at my reply. “But I can be very persuasive, Samantha.”
I couldn’t help but blush. “See you this weekend.”
It was weird getting ready for the date. As Simon, I wasn’t exactly the dating type. I preferred to brush up on my skills with a training manual than go to some nightclub. Now, I was going to date another man while dressed as a woman.
Nonetheless, I was more than prepared for him. As Samantha, I had accumulate a large wardrobe over the past few months. I had also expanded my makeup collection to include a large variety of tools and colors. I changed into a tasteful one piece dress and used a subtle designer perfume.
Satisfied, David arrived in his car to pick me up at the garage. I didn’t want him to know where I actually lived. The man wolf-whistled when he saw me. “You look stunning!”
I rolled my eyes and laughed. “Take your jaw off the ground. We got dinner waiting for us.”
He smiled back at me. “You’re the boss!”
David was used to treating clients out for dinner so he knew a few good places. We settled on a nice French restaurant that he enjoyed. Apparently, it was pretty famous but I wasn’t exactly a foodie. My date must have been a favorite customer since the place gave him the star treatment.
“It’s good to see you again!” the hostess greeted David. She gestured to a waitress to help us. “Your regular table?”
David nodded. “Yes, I want to have some privacy tonight.”
“Excellent,” she said, letting the waitress to guide us. “We’re having an evening special. The duck is especially good. Furthermore, please enjoy a complimentary wine.”
When we sat at the table, I remarked. “Do you get the five star treatment at every restaurant you visit?”
My date grinned. “You’ll be surprised what kind of doors will open if you tell people that you’ll help them with their taxes.”
“This place is too rich for my blood,” I said, staring at the expensive furnishings. David must’ve had a lot of power and influence to land an easy reservation at this place. I felt even more of an impostor due to who I was than what I wore. I was the type of guy who was happy with a microwaveable dinner. “I’ve never been to a restaurant this fancy.”
“Believe me, Samantha,” he said, gesturing for the waitress to take our orders. “You’re pretty damn classy.”
After a half hour of sipping wine and enjoying appetizers, our delicious food arrived. I couldn’t remember the last time I had been treated out to a dinner like this. At work, Jerry would try to get me to go with him to a local bar for beer and chicken wings. It was his idea of a fancy dinner.
Nonetheless, David’s company was just as enjoyable as the food. He knew how to make me laugh at a moment’s notice. I never thought I’d end feeling this way about a man. For months, I had focused on survival than the finer things in life.
After we finished, we went upstairs to rest in a lounge. It gave us a good view of the city. David took me to a balcony where we would have some privacy.
With his hand on my waist, I stared out at the cityscape and remarked. “What a view…”
“The view is the biggest reason I came here,” he replied, turning to face me. The man looked unbelievable handsome against the moonlight. His hands moved down to my hips. “Among other things…”
Just like that, we kissed.
It hot and wet. I forgot that I was even a man posing as a woman. I was falling hard for David. This wasn’t going to end well but it was too late to stop it now. For now, I enjoyed our sensual kiss.
In the back of my head, I couldn’t help but get worried. It felt wrong to deceive him after all he had done for me. We could never be a real couple. The closer we got, the more likely he was to uncover the truth.
Nonetheless, I’d just have to take it one night at a time. As it neared midnight, I asked David to drop me back at Jerry’s Shop. Otherwise, I could’ve led him back to my apartment as Simon.
Predictably, he raised an eyebrow. “At the garage, Samantha?”
I tried to put on a straight face. “I’ve got some work to catch up on.”
He eyed me from head to toe. “In a dress like that?”
I giggled nervously. “A mechanic’s work is never done.”
Nevertheless, David did what I requested off him. He gave me a lingering goodbye kiss. However, I wasn’t eager to leave him just yet. No one had been as kind and thoughtful to me as he had.
I didn’t know whether it was the guilt of deceiving him or the love I felt for him but I wanted to please David. I reached down for his belt buckle. I knew he had been hiding an erection this entire night. Now was the time to relieve him of tension.
Before he could even react, I pulled down his pants and took out his growing hard-on. Even in its budding state, his prick was much thicker and longer than mine. I remembered how I had sucked Jerry off to get a job as a mechanic. Now, I was sucking David because I deeply cared for him.
I began by stroking the length of his shaft. My fingers had honed their talents from years of working with delicate car parts. My dexterity was making David as hard as a steel bar.
Satisfied with its hardness, I lowered my mouth to swallow the head of his shaft. I felt its bulbous tip radiate with heat. I took more and more of him inside of my mouth. He was so long that it was hard to take him.
I gave David the star treatment. I teased the tip of his prick and licked its soft underside. I even went down to lick his balls. Glancing up, I saw that he was delirious with pleasure. Soon, his cock throbbed and warned me of what was to come.
Whether it was his pent up desire for me or the sheer intensity of my blowjob, my date couldn’t hold back. David came powerfully and loudly in my mouth. I drank down his sticky release as he groaned above me. Finally, I let him go and wiped my mouth clean with some tissues.
“Oh wow…,” David groaned, a look of complete satisfaction on his face. You would’ve thought he had just won the lottery. “What a woman…”
It was bittersweet to hear that. “I’ll see you around, David.”
After he left, I took a bus home to my apartment. My mind was a jumble of different emotions. What I felt for David was real. Yet, I had been deceiving him all this time. I didn’t know how he would react if he found out. Like the rest of my relationship with him, I kicked that can down the road.
I knew I couldn’t go on being Samantha forever. I had more money than I knew what to do with. I could stop being her and retire. At the same time, I wasn’t looking forward to going back to being boring old Simon.
I’d just have to deal with it later.
Chapter 5
It was hard going to work the next week. Normally, I loved burying myself in work and repairing multiple cars at one time. It always put me in a Zen-like state of mind. However, my mind was now fixated on David.
I loved being with that man. However, I knew a long-lasting romance was impossible. As real as she as felt to him, Samantha was a constructed person. She existed so I could work at Jerry’s Shop. I couldn’t risk everything I had accomplished so far just to be with David.
For the time being, I continued to date him. David treated me to romantic dinners and trips to the museum. We even visited his upscale apartment in the city on occasion. I gave him a round of fellatio from time to time but I never escalated it to full blown sex.
David always acted like a gentleman. He never pressured me to put up or do anything I wasn’t comfortable with. I was blessed to be with such a man. I really didn’t deserve him.
It was like wearing a straightjacket all of the time. I couldn’t fully express my love to him. I told myself it was best if I kept my emotional distance from him. Our romance was a ticking time bomb waiting to go off at any second.
And it did one day.
A month later, David and I were heading back to his apartment after a hot date. We had a great time hiking in a nearby mountain trail. It was fun getting out of the garag
e and enjoying new experiences with him. I couldn’t blame myself for falling so hard for the guy.
When we got to his place, David looked unusually serious. Throughout the trip, he had been acting a bit distant. I wondered if he was planning on breaking up with me. I couldn’t blame him for looking at the door. Our intimacy had hit a wall since I was not willing to have sex with him.
That’s when David sighed and said. “Samantha… I know the truth…”
I sat still as a statue. “David, I don’t know what you’re talking about.”
He pulled out his phone and pulled up a photo. It revealed a picture of me as a man back at my old garage. “I know who you are… Simon.”
Panic spread across my body as my heart thundered. “David, I-I can explain!”
“I didn’t intend to snoop,” he explained, locking eyes with me. “Working for the IRS meant that I always knew when someone’s cover story didn’t add up. You kept asking me for tax advice. You never let me know too much about your personal life. It didn’t take me too long to piece together everything and find out that you were actually a man named Simon.”
I felt completely deflated. “I’m sorry, David. I never meant to trick you. I just needed this job and they only way I could get it was by becoming Samantha.”
David paused for a moment and asked. “Who else knows? Your boss, Jerry?”
I sat up straight at my boss’s name. “He doesn’t have the slightest suspicion. No one else at the garage knows who I really am. Please, you can’t tell them or else I’ll lose my job!”
He shook his head. “No, I’m not going to do that Simon- I mean Samantha.”
I stared back at him in disbelief. “You’re not? But I lied to you!”
David chuckled and sat down next to me. “Samantha, I’d never hurt you. I won’t tell anyone else who you are. It doesn’t matter if you’re a man or a woman. I love you… and I want to be with you forever…”
I couldn’t believe what I was hearing. “You love me, David?”
“Of course I do,” he said, planting a soft kiss on my lips. “We have something special and I wouldn’t trade it away for the world.”
The sheer love I felt for David in that moment made me lean forward him and kiss him back. He loved me who I was rather than what I looked like. All those months of uncertainty and fear evaporated as we locked lips. Samantha stopped being a disguise and became as normal as my skin.
My lover and I fell onto the couch as our tongues tangled. I felt his hands begin to undress me. He wanted the soft, untouched flesh I had kept hidden from him. I watched as he took off my skirt and removed my panties.
The man cupped my buttocks and felt my bare flesh bubble in between his fingers. I didn’t have a pussy for him to fuck but I did have another entrance for him. David got the same idea when he brought a finger between my ass cheeks. I moaned as he began rubbing my backside.
I helped David take off his pants. We had always stopped at a blowjob. Now, we were going all the way to the end. With my guidance, I brought his massive erection to the rosebud of my ass. Finally, he entered me with one swift thrust.
I groaned as a bolt of sharp pain rippled through me. He was careful not to go in too quickly. David slowly inched his way inside me so I could get used to his prick. Soon, I began to enjoy new sensations I was feeling.
Once inside of me, David settled into a steady rhythm of thrusts. “Damn, your ass feels great, Samantha…”
I moaned. “Yes, fuck me, David!”
The walls of my ass converged on his lengthy cock as he fucked me. His balls slapped against my ass when every thrust. We were both new to this but David made love to me with uncanny skill.
It went on and on without pause. The weeks of holding back only meant that the flood would be that much bigger. David fucked me like a man possessed. His cock had gotten unbelievably stiff inside of me. It was practically a battering ram that buried itself to the hilt.
He wasn’t the only one with a huge erection. My prick was trapped between my body and the couch. There was so much friction against it that it didn’t take long for me to near my climax.
David and I moaned together in erotic delirium. He seemed to go into overdrive and broke out into a series of frenzied thrusts. I heard him groan as he pounded me. “Samantha… I’m going to come!”
I raced to my orgasm by grinding my ass against David’s shaft. The faster he fucked me, the harder I gyrated against him. It felt like a competition to see who would come first.
It was a tie.
Together we both achieved a mutual climax. I felt a splash of warm come inside of me as I unleashed my load onto the couch below. His cock throbbed inside my ass while spewing its load inside my ass’s walls. When he finished, he fell on top of me.
“Simon… Samantha, whoever you are,” David began, catching his breath. His hand caressed my face. “I love you with every fiber of my being.”
I turned to kiss him. “I love you too, David.”
I never felt so happy in my life. It was a huge burden off of my back to have David know my secret. Better yet, he loved me now more than ever before. I decided it was it was time for us to be officially be a couple. Through David’s connections with the government, I forged a new identity as Samantha which would legally keep me in the clear as her.
I wanted to leave Jerry’s Shop behind and start a new life with my boyfriend. Of course, I didn’t mind wearing that sexy uniform from time to time. Nonetheless, I didn’t want to work for Jerry anymore. That guy spent more time harassing my co-workers than running his business. It was time to cut myself loose.
However, David had a better plan. Working for IRS gave him a keen insight into businesses. He knew that Jerry was crooked and ran his business using every trick in the book. The man harassed his employees and paid people under the table. He was begging for some to intervene.
David made a few calls to his friends and had the federal government looking into Jerry’s Shop. My boss started sweating bullets when the IRS wanted to look into his finances. The man could end up in prison for tax evasion. Soon, Jerry started looking around for someone to sell his business to and get out of the country.
That’s where I came in.
With David’s help, I bought the business off of Jerry for a bargain. I would’ve felt sorry for the guy if he wasn’t such a prick. Nonetheless, I became the new owner of the garage. My co-workers were more than happy to see me replace their old boss. I was going to turn this business into a great place to work.
Samantha’s Shop was officially open for business!
Chapter 1
My name’s Greg and I’m the best damn singer you’ve never heard of.
Sure, it’s not the best title for a budding singer like myself but it was the truth. My family always said I had the voice of an angel. I could sing a baby to sleep. I could make women weep with my voice. Even grown men would stop in their tracks to listen to me.
Unfortunately, it wasn’t the masculine baritone voice producers in the music industry were looking for. I was a true countertenor that sounded more like a high-pitched woman. Sure, I had range but producers preferred to hire someone who looked and sounded manlier than me. They wanted this charismatic lead singer that I didn’t resemble the slightest bit. I counted myself lucky to get work wherever I could.
Becoming a singer had always been my dream as far as I could remember. While my brothers enjoyed playing sports and becoming athletes, a scrawny guy like me gravitated to musical activities. Before long, I was singing as lead choir at school and as the lead vocalist for a local rock band. It allowed me to develop my innate talent as a singer.
It took me years to become a professional singer but I managed to accomplish it. I didn’t always get the type of work I always wanted. My voice was too soft and feminine for traditional male singing roles. I couldn’t really complain since most people in my professional struggled to pay the bills. I counted myself lucky to have a steady stream of work.
That wasn’t to say I got the type of work I desired. More often than not, I was in a recording booth for radio jingles and commercial voiceovers. My soft, high-pitched voice was perfect for narrating commercials. I wanted to be in front of a crowd and sing my heart out but I had to be mindful of the bills as well.
I tried to sign up with a few record labels but they all rejected me. I wished it was as simple as the best voice getting the job. However, the big labels were looking for charismatic pop stars. They wanted a guy who they could land on the cover of a Men’s Health magazine. On the other hand, my feminine features made me a front runner for Elle Girl magazine. I simply didn’t have the look these companies were looking for.
The Trans Ultra Collection Vol 3 Page 6