Are You a Sissy?

There I was, early Friday evening, standing on the front steps of my co-worker, Liam's house. As instructed, I brought with me a small overnight bag with the following items: a toothbrush, toothpaste, razor, shaving foam, and flip flops.

I was nervous. I was not sure what was in store for me. But I had an idea.

On Tuesday, Liam had called me into his office. He had been reviewing my internet history and found that I had been looking at porn. He told me that I could be fired and that he could go to HR with the information. I begged him not to do it. I told him I would do anything. I needed to keep my job. He said he would think about it and that we would talk the next day.

On Wednesday, Liam asked to take me to lunch. I was surprised, but I agreed. At lunch he asked me about the porn sites in my history. He had visited some of them himself.

"Are you a sissy, Michael?" Liam asked.

"What do you mean?" I looked down into my lap knowing exactly what he meant.

"The websites you visited—there were videos of crossdressers and transgender women having sex with men." Liam's voice was measured and confident. "I've always thought that perhaps you were gay. You are certainly quite feminine. But after seeing these sites, I realized that you must be a sissy, or perhaps you are a transgender woman and haven't come out yet."

I sat quietly, not responding to Liam. I felt exposed. I was too scared to speak.

"No matter what the answer, it's ok Michael. But I need you to be honest with me."

"Ok," I said.

"Are you a sissy? Is that a good word for what you are?"

"Yes. I think so."

Liam smiled at me. It seemed genuine and warm. "Good girl. Thank you for being honest. Can you answer a few more questions?"

I nodded yes.

"Do you like to wear women's clothes?"

"Yes, I do."

"And are you attracted to men...sexually?"

"Yes, sometimes, when I'm dressed as a girl."

Liam took out a small bag from his briefcase and handed it to me. "Look inside. What do you see?"

I opened the bag and peeked inside. "Pink underwear."

"Would you like to be wearing them?"

"I... I don't know." I desperately wanted to be wearing them.

"Let me put it another way, Michael. I would like you to wear them."

"Ok."

"I want you to go to the bathroom right now, here in this restaurant. I want you to take off your underwear and throw them away. And I want you to put on these pink, silky panties and keep them on under your clothes for the rest of the day. Can you do that for me?"

"Yes."

"And one more thing. When we are alone, and you are speaking to me, I'd like you to call me sir. Understood?"

"Yes, sir." I smiled at Liam and shuffled off to the bathroom with my gift.

Was this really happening? Did Liam want me to be his sissy? I never thought Liam was gay. He was older than me, much stronger and taller, with a salt and pepper beard and square jaw, the epitome of a successful business man.

Just as I was about to slip the pink thong on, my phone beeped. It was a text from Liam: 'Make sure to take a picture.'

I texted back, 'Yes, sir.'

I suddenly felt queasy. What if he's just toying with me, getting me to humiliate myself before he goes to HR with my web history? I had to risk it. I had to take a chance that this would please him. I hiked up my shirt, and took a picture of the front of the panties, with my now thick cock pressed up against the fabric.

I hadn't been this turned on for quite a while. I felt flushed and my breathing was shallow. I walked back to table and sat down.

"Did you take a picture?"

"Yes, sir."

"Send it to me."

I took out my phone and texted him the photo. He smiled and turned to me, placing a hand on my knee, "Good girl."

We drove back to the office and Liam parked the car. "We will talk again tomorrow. Until then, you are not to touch yourself, understand?"

"Yes, sir."

On Thursday afternoon, Liam called me to his office. He closed the office door and offered me a seat.

"Have you thought much about our lunch date yesterday?" Liam asked.

"I couldn't stop thinking about it, sir. I could barely fall asleep last night."

"And did you touch yourself?"

"No, sir. I did not. It was difficult, when I think about the pink thong you gave me, I get excited."

Liam stood in front of me and leaned against his desk. He looked down at me and I looked down at his shoes. "Do you have a name? You know, a girl's name that you like to use when you are online?"

"I like the name Bethany, sir."

"Then I will call you Bethany. Would you like that?"

"Yes, I would like that, sir." My little boy clit began stirring. I liked how my name sounded on Liam's lips.

Liam reached out and nudged my chin up slightly encouraging me to look into his eyes. "Then I shall call you Bethany."

He made his way around his desk and sat down. We talked for a few more minutes. He told me that he was willing to destroy the records of my website browsing on two conditions. First, I would agree never to look at porn at work again. And second, I would agree to spend the weekend at his home.

"What will we be doing over the weekend, sir?" I asked.

"Only things that you want to do, Bethany. The things you have been dreaming about."

Liam gave me a piece of paper with his address and a list of things to bring with me.

"I'll see you at 7 tomorrow evening."

"Yes, sir."

And that brings us back to Liam's front steps on Friday. I knocked on the door and a few moments later, Liam answered.

"Hello Bethany," he said. His smile was warm and inviting.

"Hello, Sir."

He brought me into kitchen where I met a pretty woman in her thirties. Her name was Rachael and I was to go with her and do as she said. She brought me upstairs to the guest bedroom and told me to undress. She followed me into the bathroom and started the shower for me. She instructed me to clean myself thoroughly and then to use the razor and shaving foam to remove all the hair from my body. After, she helped me dry off, she applied moisturizing lotion all over my body. Then she sat me down to give me a makeover. She plucked my eyebrows and applied makeup: a little eyeliner, a little color for my lips. She painted my fingernails and toenails pink. She styled my hair and gave me some jewelry to wear. I was always a bit feminine and my hair was always a little long, but she transformed me. When I looked in the mirror, all I saw was a girl, not a boy in makeup.

She helped me get dressed. Liam had picked out an outfit for me: pink underwear, a white blouse, a pink tartan skirt and white anklet socks with a bit of lace on the top and pair of schoolgirl mary jane shoes.

I looked in the mirror, astonished. I had dressed myself more than a few times, but I never was this convincing, never this girly. I hugged Rachael.

"Thank you so much! I love how I look."

"That's what I do. It's my job, honey." Rachael handed me her card. "Have fun, sweetie. I'll probably see you tomorrow."

And with that, she left. I wasn't sure what to do next. I sat on the bed, wondering if I should head back downstairs or wait there. Then I heard Liam's voice on the intercom.

"Hi sweetheart. Are you all done with Rachael?"

"Yes, I am, sir."

"Good girl. Come back downstairs and find me in the den."

After a little bit of poking around, I found Liam sitting in his den. It was furnished with leather chairs and bookcases lined the wall. He still wore a suit, although his tie was gone and he hand unbuttoned the top button.

He showed me to a chair and he stood a few feet away from me. He handed me a glass with a small amount of whiskey. He drank from his and I took a sip of mine. It warmed my throat.

"Are you ready to have a good time, Bethany?"

"Yes, sir. But can I ask you one thing?"

"You sure can."

I took another sip of my drink, hoping my next question would not turn him off. "Instead of calling you sir, can I call you Daddy?"

A sly smile came across Liam's face. "You sure can. I'd like that."

"Thank you, Daddy." I drank down the rest of the drink and set aside the glass.

"Now, what would my girl like to do first?"

I stood up and walked over to Liam and kneeled down on the ground in front of him. "Awe...is my little girl hungry?"

"Famished, Daddy."

And with that, I removed Liam's belt and unzipped his pants. I lowered them to the ground allowing him to step out of them. Then I pulled down his boxer shorts and revealed his cock, already stiff and erect. I grabbed it in my hand and gently but firmly stroked it. I looked up into his eyes and let the tip slide into my mouth.

It felt wonderful. It was a sissy dream come true, me dressed like a schoolgirl, sucking on my Daddy's cock. He gently put his hand on my head and slowly moved his hips back and forth, fucking my mouth and throat. Somehow, he managed to penetrate me in a way that was both gentle and forceful, loving and animalistic.

I put my hands behind my back and let him take full control. I moaned every time his member pushed against the back of my throat. I felt him grow harder and thicker. His precum mingled with my spit and dripped down my chin.

After a few minutes he pulled back and told me he was going to cum. I leaned my head back and stuck out my tongue, eager to be his little porn star. "Yes, Daddy! Cum on my face."

I felt a warm thick cream splash against my lips and tongue. It smelled familiar. It wasn't my first time tasting cum, but it was the first time tasting someone else's cum.

After several spurts, he brushed my lips with the head of his cock as he squeezed out the last drops. He seemed overwhelmed. His breath was shallow and quick. He sat down in one of the chairs of his den. And handed me his glass. I took it over and poured him another whiskey and brought it back to him.

I was still licking some of the cum from around my lips when he pulled me down onto his lap. He kissed me deeply, pushing his tongue deep into my mouth. I could feel his wet cock against my thigh, starting to get hard again. This was just the first of many rounds, I hoped.

"Did you like that, baby girl?" he asked.

"Yes, Daddy."

"You are a good cocksucker, Bethany."

"Thank you, Daddy." I leaned against his shoulder nuzzling into his neck and started giving him little kisses. My hand reached down to hold onto his cock and tugging at it softly. "What are we going to do next, Daddy?"

"Whatever, my baby girl wants."

And with that, he picked me up and took me to the master bedroom. What happened is for next time.