That was his cue to come.
That made two of us.
I came on his hand and it covered both of our bodies.
He came in me and filled up my bowels with his seed.
We were both yelling and screaming.
Ben thrust his cock into the depths of my ass.
I had been stretched to my absolute limit.
Together, we fell upon the couch in utter exhaustion. I was too tired to escape him. Even then, Ben looked too tired to chase after me.
However, he wasn’t looking at me as if he was some rogue FBI Agent. Instead, I saw the look of a man utterly in love with me. I wanted to lie down next to him and bask in his warmth.
Ben tenderly stroked my cheek. “That was the best sex I ever had.”
I whispered back. “What are you going to do with me? Will you still tell the mob?”
“Hell no,” he said, shaking his head. “I sure as hell not going to hand over a treasure like you over to them. Hell, they can’t even pay me if I did the deed. They’ll be dead in a couple of weeks and I don’t plan on going down with them. You’re staying with me.”
I planted a kiss on his lips. “Thank you!”
“I’ll tell them that they took you to Alaska and I can’t get to you,” he began. “Just on one condition.”
“A condition?”
“We’ll meet up together once a week,” he said. “But you come to me as Loretta.”
“You want me to dress up as a woman?”
“No, I want you to be a woman for me.”
It was a lot to chew over. Yet, I didn’t mind being Loretta. I enjoyed being her more than I ever liked being Larry. Going back to being a boring bank teller felt like a betrayal. I didn’t have to think twice about this. “Deal.”
Of course, I had ulterior motives to just staying alive. I enjoyed sex with Ben. Most of all, I enjoyed having sex with him as Loretta.
We split for the next few weeks. I met up with Amy who told me that the mob had been thoroughly dismantled. I didn’t have to go into hiding any longer. I could go back to my old job.
Of course, I didn’t do that. Ben used his contacts to make new documents for Loretta. I moved into a new flat close by him. I got a job as a waitress at a local pub. I had begun to settle into my life as a girl.
Ben did a disappearing act of his own. The FBI agent changed his identity when his fellow agents began an investigation on him. He was on the straight and narrow now under his new identity. I feigned ignorance when Amy came to for any leads. I hated to lie to her but I wanted to move on with my life with him.
Yes, it would be a new life with Ben by my side. I felt him place a hand on my shoulder and beckon me to our bedroom. “Are you ready, Loretta?”
I put down my journal and smiled at Ben. “I’ve just finished writing. Let me doll myself up first.”
I had that itch again.
I was an actor by nature. As a young boy, I knew being an actor was my calling. I loved putting on someone else’s clothing and pretending to be them. I didn’t mind dressing up as a woman. Hell, I even preferred it.
There was so much to do in order to create illusion of being a woman. I had to make sure my makeup and clothing were perfect. One small mistake could ruin the effect.
I was thankful for the fact that I lived alone in my condo. It was small but that also meant I could pay for it on my own. I didn’t have to split the rent with a roommate. I could dress up without someone judging me for practicing my art.
Nevertheless, I had other important things to worry about, such as my job search.
Are you looking for an actor?
Then Harold B. Jacobs would love to be at your service!
Acting jobs were hard to come by these days. I made due by doing various odd jobs, such housekeeping and dog sitting. I had saved up some money but I was waiting for next break as an actor. I’d love it if someone paid me to dress up as someone else!
I had begun putting on women’s clothing just to develop my skills as an actor. Another actor had suggested it to me during a workshop. At first, I thought he was crazy. How would putting on panties and a dress make me into a better actor?
More out of boredom and curiosity than anything else, I gave it a try. I went to a store and brought some women’s clothing. I made sure to say that they were a gift for my non-existent girlfriend.
In all honesty, I wasn’t exactly an expert in what women wore. I just picked up anything within my price range. Nonetheless, I was surprised at the quality of the clothing. They were soft, silky, and beautiful. Some of them were rather sexy and exposed a great deal of skin.
To my surprise, it completely changed my life. Dressing as a woman stopped being an acting exercise and became a preoccupation. I started buying more women’s clothing than actual men’s clothing. At work, I made sure to take any dresses a production company would normally throw out. Soon, I had built a sizeable wardrobe.
The clothes looked quite good on me. Sure, I didn’t have a woman’s curves but the clothing fit my body nicely. The fabrics were soft and comfortable. I actually had a hard time going back to wearing heavy men’s clothing.
After some brainstorming, I decided to put on a set of bras to give myself a bust. A couple of strategically placed gel molds finished the illusion. It filled out my dress and made my appearance look more believable. A sexy set of garter stockings completed the look.
Week after week, I built up my stock of clothing. I didn’t have much money as a chronically unemployed actor but I spent it on clothing and makeup. Soon, my cosmetics collection was even bigger than that of my sister.
I had everything from eyeliner to mascara. It took a few internet guides before I realized how to use concealer and eye shadow effectively. I couldn’t exactly ask a friend for advice when it came to something like this.
With some practice, I became quite good at feminizing my body. Most of my friends would’ve mistaken me for someone else. Hell, they would’ve thought that I was damn sexy!
I just couldn’t stop dressing up. I just felt so beautiful. Just about everything fitted me well. Although, high heels took some work. With time, I could strut in them like any supermodel.
At the same time, I was worried about someone finding out about my secret.
Would they think I was crazy and make fun of me?
Would they believe I was doing it as an acting exercise or see past my excuses?
In any case, I didn’t want anyone to find out. I didn’t tell even my closest friends or coworkers about my secret. Word traveled fast in the acting industry. I could be blacklisted as some weird degenerate if I wasn’t too careful.
The actor in me worked to perfect my craft. I practiced speaking in a woman’s voice by shifting my pitch. After I became more confident in my abilities, I would do phone interviews with film production companies. I posed as an up and coming actress named Harriet.
My performance was so real that no one suspected that I was a man. Some of the interviewers were absolutely head or heels in love with me. Unfortunately, I couldn’t accept any of their offers to come in person and continue with a formal audition.
Strange as it was, I was more successful at finding work as a woman than I was as a man. I thought about applying for a role as Harriet but I knew the charade would fall apart once they asked for my personal information. This female doppelganger of mine would have to stay within the walls of my condo.
One day, I sat at my computer looking for jobs while dressed up as her. As hard as it was finding work, cross-dressing alleviated some of the stress. I had begun to take better care of my hair. I had grown it long and washed it daily with a shampoo. I enjoyed the way it touched the back of my neck.
I was so busy admiring myself that I didn’t notice a man peer through my window as he walked by.
My heart froze.
I recognized him.
It was Jack.
He was a well-connected casting director who I had just gotten in touch with. He
was supposed to interview me for a role in an upcoming television show before I could audition for it. Jack was looking for someone local and I had applied for the role. I was so busy dressing up that I had forgotten about the interview.
Worse yet, he had seen me dress up as a woman. I didn’t know what he was even doing here. Most interviews were conducted at an office. My condo was no place for an audition.
Then again, that didn’t mean that he believed the woman was actually me. It was possible he saw me as just a woman rather than Harold. At least I hoped that was the case.
Regardless, I cursed myself for not lowering the blinds over my window. I raced over to the window to close the blinds. However, it seemed that Jack was long gone.
It took a moment for me to gather my thoughts. Jack was well-connected with the local film production scene. Just about any actor worth his salt knew him one way or another. If Jack had seen me dressing up as a woman, then the secret would be out. I wouldn’t be able to find work ever again!
It didn’t help that I was in need of acting work. All the odd jobs I was doing were wearing me out. I needed a meaty role for the sake of my sanity.
I had trouble sleeping that night. I was worried that my reputation would be ruined. I wouldn’t be able to get any acting role or odd jobs without skipping town. I would be left with a ton of bills and no means of paying for them.
I managed to somewhat relax the following day when I didn’t get any weird text messages about dressing as a woman. Jack probably mistook me for someone else. He may have thought he had found the wrong condo.
That is until I heard a knock on the door.
I looked through the peephole.
It was Jack.
I gulped in terror. I was terrified about confronting him. He had seen me in drag. Jack would think I was insane and needed to be locked up in the nuthouse.
Worse, I needed to find decent work as an actor. My odd jobs barely kept my head above the water. Jack wouldn’t just refuse to work with me. He could have me blacklisted from working with any other production company.
I heard him ring the doorbell. “Hello, Harold? It’s me, Jack.”
He didn’t sound angry or upset. Nonetheless, my heart thundered in my chest. I couldn’t avoid this any longer. I needed to answer him and hope for the best.
I mustered a smile and opened the door. “Hi Jack.”
“Hey Harold,” Jack said. The look on his face was unreadable. It was hard to tell how he felt when I was auditioning for him. Now, it I was having a harder time telling if he was upset or not. “I dropped by earlier but it didn’t seem like you were home.”
I relaxed a little bit. It didn’t seem like he knew that I was the woman that he saw earlier. “What were you doing here?”
“I thought I’d tell you in person,” he said with a sigh. “Management wants to take the role you’re auditioning for in another direction. I knew your heart was in the role so I wanted to break it to you in person. I’ll let you know if something else comes my way.”
I was out of the freezer and into the frying pan. I may have avoided embarrassment of being caught cross-dressing but now I was out of a job. I was just barely keeping up with my bills. It didn’t help that I had splurged and bought a black dress that was on sale. It wouldn’t be long before I had to dip into my savings.
That’s when I noticed Jack look over my head and into the interior of my condo. My heart skipped a beat. Was he looking for women’s clothing?
I was careful enough to not leave my feminine clothing lying around. I tried to play it cool. “Something wrong, Jack?”
He shook his head. “No, it’s just that I saw a woman here when I dropped by the other day.”
I forced a chuckle. “That was a friend of mine… another actress. Her name is Harriet. She’s staying over for a couple of days.”
The expression on his face finally softened. Jack seemed to buy my excuse. “Pretty girl! If she’s looking for work, then give me a call. I’m sure I can find some work for her.”
I would’ve laughed if the situation hadn’t been so awkward. “I’ll keep that in mind. Just let me know if you have any openings for me.”
Jack left which gave me time to gather my thoughts. I needed to find a new acting gig. My various little odd jobs barely paid for my expenses. I knew being an actor was a struggle but I was at my wit’s end.
I thought about quitting acting and getting a regular job. However, I loved acting too much to make the switch. It would be like denying who I really was and admitting defeat. I might as well have stopped existing.
Nonetheless, I needed to find work and soon. Dog sitting could only bring in so much dough. I spent the next few days applying for any acting jobs I could find. It didn’t matter if I was some throwaway extra as long as it paid.
However, no one offered me a role or even an audition. I needed to find work or risk dipping into my meager savings. Even with that small cushion, I was two months from declaring bankruptcy.
If there was a silver lining, then it was dressing up as a woman. Putting on makeup and sexy clothing washed away all of my worries. It was like being a better, more confident version of myself.
In fact, I continued to apply for jobs. This time, I did it as a woman. To my surprise, Harriet had call backs after call backs.
One hot shot casting director named Alex asked. “You sound perfect, Harriet. We should meet up and discuss this further. You’re available, right?”
I blurted in my feminine voice. “Sure, I can see you.”
“Wonderful,” the man replied. Alex sounded absolutely smitten with me. As a man, I had never received even half the compliments and superlatives Harriet had just received. At the same time, I knew he wasn’t just interested in my acting abilities. “How about we meet at my place for a personal… interview?”
The innuendo was heavy with this one. Rather than be repulsed, I was aroused at the man’s attraction in me. It made me feel proud of my acting skills. I hadn’t just pulled a fast one on a casting director. I had made him fall hard for me.
I never had this level of success as a male actor. Most casting directors probably threw my resume straight into the garbage bin. The best jobs I got tended to be roles with a few speaking lines. Now, Alex was willing to give me everything… for a price.
“I’d love to meet you person, Harriet, and hear you speak,” he continued, not bothering to be subtle. “I’m sure you could do wonders with that talented mouth of yours.”
At the same time, I felt a pang of confidence. After months of fruitlessly looking for some confirmation of my acting abilities, a man believed I was a woman. I didn’t have to be Harold the underachieving actor. I could become Harriet who had to wade through the job offers she received from her admirers.
“I’m a busy woman,” I replied, not breaking character. “Could you make this visit worth my while?”
The man paused for a moment. “How about three thousand dollars for a night?”
Now, it was my turn to pause. Alex was plainly asking for a sexual favor. I knew these types of exchanges were common in the acting industry. A few of my friends had sucked cock to make a few extra bucks on the side.
Normally, I would’ve shuddered at the thought of performing a sex act with another man. However, I was beginning to enjoy the attention I was receiving from other men. I didn’t just cross-dress to look like a woman. I wanted to have the sexiness and confidence I admired in Hollywood starlets. If Alex wanted Harriet for just a blowjob, then he would never know who I truly was.
More to the point, I needed the money. Three thousand dollars was over two months of rent. It would give me some much needed breathing room as I looked for more work.
“Three thousand… but only for my mouth,” I replied. It felt strange negotiating over the payment I’d receive for sucking another man’s cock. I wondered how I would even perform the deed. Would I close my eyes and hope he didn’t realize I was a novice? Either way, the money was too good to
ignore. “The rest of me costs a hell of a lot more.”
Alex paused again. “Okay, but you better have the best damn mouth in the business.”
I took a deep breath. It was a lot of money for a quick and simple blowjob. Finally, I replied. “As long as it’s in cash.”
“I always pay in cash,” he said, his voice tinged with anticipation. “I’ll give you my address.”
Now, it was show time.
For the first time ever, I left my condo in drag. I made sure to leave at an odd hour so none of my neighbors saw me. They had the best chance of identifying me. I also didn’t want to run the risk of being mistaken as a trespasser.
The Trans Ultra Collection Vol 1 Page 4