Discretion

Rowan

Rowan was a forty-year-old gay man that behaved like a twenty-year-old twink. He had a constant aura of youthful wonder. He'd recently moved to the City from the West Coast and claimed that he wanted to start a new life.

His Amex Black Card had gotten us a seat in the VIP section of "The Black Box" and a bottle of Cristal. He watched the guys in the club wrap themselves around each other on the dancefloor in utter fascination.

From time to time he would point out a guy he liked and ask for my opinion. He wanted honesty so I gave it, even if I didn't agree with him.

"I am done watching," Rowan said, standing up suddenly. "Let's dance."

Soon, we were surrounded by guys who had their hands all over me and him. Rowan kissed and touched the bare-chested boys like a kid in a candy store. I wasn't here to be seduced by random pretty boys and kept my focus on my client.

It felt like Rowan was stalling for some reason. Most clients liked a little foreplay but there was something else going on here. Rowan was good-looking and masculine but he didn't set off my gaydar.

I know it sounded strange and it was probably just me. I'd been working a lot and hardly found time to spend with my sister. She was still unresponsive but I missed seeing her, holding her hand.

It was past midnight when we left the club. Luckily, it was a Friday night and I didn't have to go to the bank the next day.

Rowan invited me to his lavish apartment with a view of the Park. He offered me a drink and told me he would be right back.

When he returned, he stood before me completely naked. He was very nice to look at and the sight got me going.

"When you look at me, what do you see?" he asked carefully.

I told him the honest truth. "I see a very handsome, charming man. Frankly, I don't understand why he needs to pay for my services."

He smiled and walked toward me. "Thank you for your candor. Now, I want you to suck my dick," he whispered in my ear.

I lowered to my knees and fulfilled his request. I'd seen a lot of dick but his was for a lack of a better word... perfect. I swallowed it whole and he moaned as he grabbed me by the back of my head.

Once undressed, he made me lie on his sofa on my back. It was easier for him to fuck my throat this way and I enjoyed every one of his deep thrusts.

He was clearly not interested in sharing pleasure because he went from my mouth to my ass and had his way with me.

Finally, Rowan cried out together with his orgasm. When he pulled out of me, I saw him remove the condom and something caught my eye.

"Why would you fake an orgasm?" I asked carefully. It wasn't a very appropriate question for a client, they should be able to do as they pleased.

"So that's the only thing you noticed all night?" he said with a smirk. "I can find a way to work around that."

Huh?

"You were my... Turing test," Rowan said, playing with his dick like a boy in a bathtub.

"I don't understand," I said slowly.

"I wasn't planning on telling you but since you caught me, I guess you'll get an explanation."

Was this a very weird prank?

"I recently had my top and bottom surgery done by the best doctor in LA," Rowan said proudly. "I hired you to see if you could tell but clearly the surgeon did a phenomenal job."

He was trans?! Holy fuck, I really hadn't noticed. Apart from some insignificant details, I could have walked away tonight none the wiser.

"There's a guy at work. I like him a lot but I didn't want to engage  with him till I was sure."

"Sure of what?" I asked.

"That he would see me like the man I am," he whispered.

I pressed my hand to his heart and said, "What you are is here, Rowan. If he can't see that, he doesn't deserve you."

Rowan looked at me for a long while and said, "So you are a whore and a counselor?"

"Actually, I'm a University graduate who can't finish his doctorate because his sister's coma is too expensive for the shitty insurance company we have." Wow, that was harsh! I might get in trouble for that one!

"Oh," Rowan said, no longer fondling his expensive dick. "I'm sorry."

"Don't be, the world is as it is. I hope that you find happiness with your guy."

Rowan now looked like a sad puppy. The carnal drive from moments before was suddenly gone.

Suddenly, he stood up and grabbed his phone.

"I'm not going to insult you and give you money but there is something that I can do for you," he said, writing down something on a scrap of paper.

"This is a number of a friend. He is a highly respected neurologist here in the city. He can give you a second opinion on your sister's condition. Tell him that Rowan sent you, he owes me!"

"Thank you," I said in utter astonishment.

"You're welcome! Now, turn around so I can  fuck you one more time before I call it a night."