“I think you are a genius,” he praised. “I loved all your work, especially the one about airplanes. Is it true that you were on a plane that was hijacked by terrorists?”
I giggled. “No, I’ve never had that happen to me. It’s just that a joke sounds better if it’s first-person. If I said I heard it from a friend or second-hand, then it wouldn’t have the same punch. Sometimes, it’s more about how you say it than what you say.”
He pointed a finger at me and laughed. “Perhaps I should sue you for false advertising!”
I held up my hands in mock defense. “I can show you my new material.”
“I’d love to hear it,” he said, flashing another smile at me. “But first, why don’t we have dinner?”
I laughed nervously. I didn’t exactly expect to be wined and dined like this. I was still a man cross-dressing as a woman. “Is that a joke, Damian? It’s very funny.”
He shook his head. “No joke. It’s dinnertime after all.”
It would be suspicious of me to refuse such a kind gesture. I didn’t want to be rude to a fan like Damian either. “That sounds wonderful. I didn’t expect to be treated out like this.”
“It’s no trouble at all, Megan,” he said. “Tell me about yourself.”
“There’s not much to say,” I said with a shrug. “I go on stage and tell jokes.”
“You’re famous.”
I shrugged again. “It just spiral out of control after that video went viral.”
He leaned in closer. “The funny thing is that I can’t find anything on the internet about you. No private Facebook account. No idea where you went to school. Nothing at all.”
“Oh, I like my privacy,” I answered, cooking up a lie. It wasn’t too far from the truth. “You can never be too safe these days. I like to keep my life as a comedian separate from my personal life.”
“That’s understandable,” Damian replied. “I know a good bar around the corner. I think you’ll appreciate taking a break, having a nice drink, and listening to someone else tell the jokes for once!”
I had received quite a bit of fan mail over the past few months. Some of it came with nice gifts. However, no one had offered to treat me out for dinner. I always tried to keep my distance from my fans since I was afraid of my disguise following apart. Yet, Damian had an uncanny ability to disarm me.
I needed to keep my guard up. He was more intelligent than the average fan. I couldn’t reveal too much information and get caught in a lie.
We arrived at a nice bar and found ourselves a private table. The place was much classier and larger than Jim’s bar. I would’ve loved to perform here. However, a man was on stage doing his comedy routine.
Damian was friends with the bar’s owner and got all kinds of perks. It didn’t take long for us to be served. He clinked his glass against mine. “Cheers.”
“Cheers,” I replied back, sipping the drink. I watched the comedian on stage do his routine. It was as boring as watching paint dry. “At least the drinks are better than the jokes here.”
Damian smirked. “What’s your professional critique, Megan?”
“His material isn’t too funny,” I said, slipping into rival comedian mode. In my profession, you were constantly analyzing other acts. I always wanted to see what worked and what didn’t. “He has a nice delivery but he keeps repeating the same jokes. It gets stale after a while.”
“You’re more intelligent than the businessmen I work with,” he praised. “I love good humor.”
I smiled at him. “Thank you for supporting me. Without people like you, I couldn’t possibly do this for a living. Not that every fan I met is rich like you!”
Despite my new income, I never felt too comfortable in these clean, luxurious places. After all, I was an imposter. I had spent so many years working in dingy clubs that I had gotten used to them.
Over drinks, I learned that Damian was a self-made man. He didn’t inherit his hotel empire from his father. He built it up from nothing.
In turn, the man sensed my humble upbringing. When he asked about where I came from, I was careful to recite my made up backstory. I didn’t want to get caught in a lie.
I wasn’t just attracting Damian’s attention. Some of the other guests were staring at me. I was becoming a bit of a celebrity in these circles. The men looked at me with desire. However, the women were steaming jealous that I was with a handsome hotel mogul. It would’ve been funny if they weren’t staring daggers at me. Sometimes, even I forgot that I was a man.
When it came time to pay for the drinks, Damian stopped me by placing his hand over mine. “When I treat a woman out for the night, I pay.”
His touch was absolutely electric. My nipples became hard as stone. Even my cock gave a stir. I blushed and replied. “Thank you.”
I didn’t know why I felt this way. Sure, I liked being Megan but I still thought of myself as a red-blooded male. I never had an attraction to another man before this point. Maybe the alcohol was getting to my head…
“No need to thank me,” Damian replied, his hand still on mine. “I’m sure you have plenty of admirers wanting to meet you. You are a very… special woman.”
My heart thundered as I withdrew my hand. My cock hardened in my panties. “I’m not sure there’s much to admire other than my wit.”
Damian flashed a boyish grin. “Don’t be too sure about that. There is a reason that you’re so famous.”
I giggled nervously and shrank under his hot gaze. “Why is that?”
“You’re funny and you’re beautiful,” he answered, glancing at the comedian on stage. “You’re the complete package. Compared to that comedian, you’re a whole other level. You’re a stunner, not a slob.”
My heartbeat slowed down. He was right about one thing. As far as comedians went, I looked pretty damn classy in my dress. “You most know a lot of comedians through your work. What makes me so special? Other than being a woman.”
“It feels like you’re more experience than you first appeared,” he stated. The man was dangerously close to uncovering my identity. Thankfully, a server came to offer us a complimentary dessert. “I’m good. Megan, what would you like?”
I shook my head. “I got to keep my sweet tooth in check. Nothing for me.”
I didn’t want to get too relaxed like some idiot and spill the beans that I was cross-dressing.
We headed back to the limo and continued our night there. I had to admit Damian was a charmer. Most women would’ve swooned before him. I guessed that was why he was so interested in me. I hadn’t immediately given into his charms.
The man even made a move on me. His hand trailed his way to the inside of my thigh. I didn’t know why I didn’t stop him. He could easily uncover the erection trapped under my panties.
Perhaps, the danger of the situations was getting me off. I was a man disguised as a woman on a date with another man who was head over heels in love with me. The power I felt was intoxicating. I suppressed a moan was his finger made circles against the bare skin of my legs.
Damian teased me mercilessly. His finger ran across the frills of my panties. His fingertips stopped to go under the elastic band.
My prick grew unbearably hard from his touch. I had never felt this way before. Stranger still, it was another man who was making me feel this way. I didn’t know whether I would come first or that he would discover my erection.
Chapter 4
Thankfully, the limousine came to a full stop. That brought an end to our frisky activities for now. Damian guided me out of the vehicle. “I knew you were special the moment I met you in person.”
We were in front of a massive hotel complex. It had everything from an outdoor pool to a massive buffet. I wondered where I would have to perform. Damian said he wanted a private show so an auditorium was out of the question.
“I guess it’s because I’m a female comedian,” I replied. I tried not to think too much about what he was saying. If he had any suspicions about me, then he woul
d have already called the police. “There aren’t too many like me in the business.”
He held my hand in his. His skin was warm against mine. “There’s no one like you, Megan.”
I thought about canceling the performance. Damian was way smarter than I had initially given him credit for. I could risk losing everything by staying here. However, I didn’t want to leave without doing my routine. It could set off his suspicions about me.
“Something wrong?” he asked, genuinely concerned. “I hope it wasn’t the alcohol. They always make it a bit stronger than you ask for.”
I shook my head. “No, I’m just thinking about my comedy routine for you tonight. Where will I be performing it?”
Damian grinned. “My private hotel suite. It’s a penthouse, actually.”
This sounded more like a romantic date than a comedic performance. “You want me to perform in your penthouse? Talk about going beyond the call of duty.”
He chuckled. “What better place to host a talent like you? Come, follow me. I’ll take you up the penthouse elevator.”
It was too late to back down now. “Lead the way, Damian…”
I tried to formulate a plan. He was obviously enamored with me. Unfortunately, he was going to be surprised by what was between my legs.
I figured I could do my bit and then leave. I could let him down gently to avoid upsetting him. Damian seemed like a really good guy. I hoped we could still be friends after this.
Nonetheless, the man had a serious thing for me. He wasn’t just wining and dining his favorite comedian. He wanted to get under my skirt.
Literally.
I was at risk of being found out if he got too frisky under my skirt. That foreplay back in the limo was a close call. He could go even further once we went upstairs. If Damian found out the truth, then I would be exposed as a fraud. I could lose everything I had worked so hard for.
Despite the danger, I liked the attention he was lavishing upon me. After all, the man had been a complete gentleman to him. I just needed to entertain him for the night and leave before it got too hot under the collar.
Damian told me about the hotel as we rode the elevator up to the penthouse. I barely listened to him as he talked about the custom marble tiling in bathrooms. I didn’t even pay any attention to the hotel’s luxurious furnishings. My mind was a jumble of a million different thoughts.
I felt as if the slightest mistake would reveal everything. Damian was so kind that it was disarming. I watched as he opened the door. A part of me wanted to stay with him. The other part feared he would discover the truth.
Nonetheless, I followed him through the door. My heart felt like it was running a marathon in my chest. The penthouse suite was utterly gorgeous. It had a beautiful view of the city. I turned to Damian and said. “I always wanted to crack jokes in a place like this…”
“I’d prefer somewhere more intimate,” he replied in a low voice. The man glanced at a nearby bedroom. “I don’t suppose you’re in the mood for another drink?”
I could sure go for something fiery. I needed some liquid courage to steady my nerves. “I’d love something that’s not too strong.”
His bedroom was as fancy as the rest of the suite. There was a queen-sized bed that had more than enough room for two people. I sat in a nearby chair as Damian poured an expensive bottle of brandy into a pair of glasses.
I touched my glass to his. “Cheers!”
“Tell me,” he began, swallowing his drink in one gulp. “Do you drink before a show?”
“No, of course not,” I giggled. “I know some comedians are crazy enough to do it before a show but not me.”
Damian helped himself to another glass. “I didn’t think a comedian would be so self-conscious.”
“You always have to know your audience,” I replied. My skin was a flame. My cock was forming a tent in my panties. “You find the right joke for the right audience.”
He leaned in with interest. “What types of jokes do you think I would like?”
I thought about it for a second. “You have a dry sense of humor. I can tell you like jokes about your wealth. You wouldn’t be offended if I made fun of your hotel chain.”
“You’re the most intelligent woman I’ve ever met,” he said with a laugh. Damian sat and the bed and gestured towards me. “Enough chit-chat. Let’s get this show started.”
I raised an eyebrow. “Okay, where should I begin?”
Before I knew it, Damian walked up to me, picked me up, and threw onto the bed. In a show of blinding speed, he got on top of me. With desire in his eyes, he caressed my face.
I knew the man could easily find out that I was a man. I took the initiative by cupping my balls and stroking it. My hand hid my growing erection. It gave the illusion that I was touching myself.
Pinning me down with one hand, Damian began to undress himself. Despite his demanding job, the man kept in shape. He could have landed himself on the cover of a fitness magazine. He could also be on a naughtier magazine with how long his cock was. It was bigger and thicker than mine.
I never felt such an attraction to another man before. I guessed part of it was the act of being Megan. I felt like a real woman who was in awe of Damian.
As the man approached me on the bed, I crawled closer to him. Blood pulsed through my veins as my skin tingled. His growing erection swung between his legs. I reached out to gingerly cup his balls. They were as big as the rest of the package. His pubic hair tickled the soft skin of my hand.
The man wasn’t completely hardened and I knew I had to change that. I began to pump the entire length of Damian shaft. The man tiled his head back and groaned. “Yes… that’s it… touch me.”
It was almost like we were getting even. Earlier, he had teased me and nearly discovered I was a man. I was playing a dangerous game with Damian but I couldn’t stop myself. I rubbed my cock while also stroking his erection. I would’ve told a joke about what we were doing if I wasn’t too busy enjoying myself.
Touching Damian was like trying to rub a steel pole. As stiff as my cock was, his felt rock solid. I knew he wasn’t going to go soft anytime soon. I continued to stroke him while rubbing myself.
When he tried to undress me, I quickly stopped me. “No, I like fucking this way.”
Thinking it was a kink of mine, he smiled. “We’ll do whatever you want, Megan.”
The man was utterly in love with me. It was so strange having power over a man. I felt something similar when telling jokes to a crowd. There was a power in controlling peoples’ emotions. Here, Damian felt like putty in my hands. I could make him do anything if I wanted to.
The mere sight of me seemed to get him off. His breathing was rapid as if was running a marathon. His erection brushed up against my thigh.
He wasn’t the only one getting aroused. My nipples were like eraser tips. I was thankful for the fact that my dress and padded bra hid them.
As for my cock, I hoped my panties would continue to hold. I had never been so hard before. My prick threatened to rip a hole in the gusset of my panties.
I wanted Damian to fuck me. I never had an attraction to men before becoming Megan. Now, this disguise felt as comfortable as my skin. I needed that man’s cock inside of me. I felt it pulse in my hand as I stroked it.
With his cock still in my hand, he moved up to kiss me. His lips were absolutely nuclear. Down below, there was another thermonuclear reaction in my panties. My cock was sticking out noticeably under my dress. Thankfully, Damian was too busy making out with me to notice.
I had never been a looker as Mark. My lean figure never attracted much attention other than a few insults. Megan, however, had all the boys lining up before her. The look on Damian’s face was that of worship. It was funny how a dress and a bit of makeup could completely transform me.
We kissed as I rubbed his cock. Damian reached behind to cup my buttocks. At least my ass was as nice as a woman’s was. I just wished my erection didn’t balloon under my dress. It f
elt like a cannon ready to go off at a moment’s notice.
The illicit nature of my encounter added to my arousal. Here I was, a man dressed as a woman, lip locking with a man I had just met. I felt something special for Damian. Despite the risk, I wanted to stay here with him.
I locked eyes as I stroked him and he groped me. He kissed for what felt like minutes until we finally broke apart. He guided me onto my back as I still held onto his hard prick. I knew what he planned on doing with it. However, he was in for a surprise if he wanted a pussy to fuck.
I decided to take control and guide it elsewhere. I brought it to my face and kissed the moist tip of his shaft. It was already wet with some pre-cum. I rubbed his prick against my face.
The Trans Ultra Collection Vol 2 Page 19