Dating Penny Pt. 03

I made a good decision by dishing out for a fancy hotel room for Penny. Despite having already dropped thousands of dollars on her before sundown, I felt a tinge of pride when Penny "oohed and aahed" at our suite.

After taking a quick look around the room and putting her coat down, Penny skipped past me as she said "Ok strip. I want you in nothing but your cute new panties." She disappeared into the bathroom as I slowly undressed.

"And call down to room service for some champagne!!" she yelled cheerily from the bathroom.

I felt truly strange calling down to room service in nothing but lace pink panties, even though I knew no one could see me.

Penny came out of the bathroom almost tipsy with glee. "Did you order champagne?"

"Yes, Goddess."

"Yay!" she said, and jumped up to give me a peck on the cheek. I blushed.

She then plopped down on the side of the bed, crossing her legs with her arms behind her, and giggled at me. "You look ridiculous."

"I know, Goddess." I managed to laugh too. Then there was an awkward silence as we stared at each other, me not knowing what the next move was.

All of a sudden a knock at the door broke the silence. We still were staring at each other for a moment, until Penny drew her eyes towards the door, as if to say "uhhh, I'm not getting that." I panicked, but also knew I had no choice, so I sheepishly walked to the door.

I opened it a crack and awkwardly stuck my head out. A friendly bellboy said "Hello Sir! I have your champagne - may I come in?" I started to mumble "no no that's fine I can ju--" and then I heard Penny's voice from the room yell "yes please! You can come in! Over here!" The bellboy and I looked at each other, and then I pulled the door open as I attempted to hide behind it. He came in, and I could see Penny's devilish, toothy grin as he walked into the room, briefly none the wiser. As he made small talk with us and set up our champagne, Penny smiled with glee awaiting the big reveal. I attempted to hide behind the door as he set up the champagne but eventually he turned around and did a double take. He kept his cool but clearly was startled. I was humiliated. Penny was ecstatic. "The boy in the corner has your tip," she said. I don't know which of us was more mortified, me or the bellboy, but in an effort to quickly end this humiliation, I rushed over to my pants to get my wallet, dished out a few dollars, clumsily pushed them into the bellboy's hands and said "thank you we're all set", all while Penny giggled in the background. He hurried out.

As the door closed, Penny's giggles turned into full blown cackles as she rolled on her back on the bed. I stood there awkwardly, finding it difficult to join her in laughter. She looked at me and sighed. Suddenly her attitude became full of scorn. "You better get used to this if you want to be my cuck."

"Yes, Goddess," I said.

"Pour me a glass of champagne," she snapped. I was at once impressed and terrified how quickly she could go from glee to scorn.

I poured her a glass and handed it to her. She took a sip and looked at me. "Get on your knees," she said. I knelt before her. She wasn't smiling anymore.

"This is what's going to happen now," she said, no longer making eye contact, as if already bored with me. "You're going to help me get ready to go out. Lucky you. Then you're going to take me to dinner. Then your mission starts: you must find a big dicked stud to take me back to the hotel and fuck me. If you fail to find one by 2AM, I will refuse to see you again. If you do find one, you get to watch me get fucked. Understand?"

"Yes, Goddess," I said.

"Good. Any questions?"

"Umm, how will I know if someone has a big dick?" I said.

She chuckled. "That's for you to figure out. But if he isn't hung, you fail."

I gulped. "OK, Goddess."

"Now let's get ready," she said, standing up and handing me her champagne. But before I could move she said "you stay right where you are, and stare straight ahead. If I catch you looking at me there will be punishment, ok?"

I nodded.

She started moving about the room, and soon I could sense out of my peripheral vision her clothes dropping to the floor. It was torture trying to stare straight ahead. Occasionally she would approach me, take her champagne glass out of my hand and stand in my peripheral vision, while I was desperate to look at her. Eventually, she disappeared into the bathroom and I heard the shower turn on. I was tempted to sneak into the bathroom and watch her but was terrified of upsetting her.

After what seemed like forever, I heard the shower turn off, and I tried to listen for hints of what might be happening in there. After a minute or two, I heard a stern "Brandon! Here!" being yelled from the bathroom. I hurried over, and as I turned into the bathroom I saw her standing in just a white towel, wrapped around her chest.

"Did I say you could look at me?" she sneered. I quickly looked away. "Sorry Goddess." I said.

"It's fine," she said, "I have a new task for you." I looked back up at her, and with that she dropped her towel. For the first time I got a glimpse of her naked body from the front side. She looked incredible, and she knew it.

"Come pick up my towel and hang it up," she said as she turned to the mirror and started primping herself. I rushed over and did as she asked, and then stood awkwardly behind her waiting for her next order. She turned, and leaned back against the sink with her arms to the side. "I need somewhere to sit while I do my makeup," she said.

I was about to run out to the main room and find a chair when she swiveled around to face the mirror again and said "your face will do just fine."

I paused, not knowing what she meant, not knowing what to do. Then she made eye contact with me through the reflection in the mirror, and sternly said "get your fucking face down here so I can sit down."

I quickly but awkwardly dropped down to figure out how to get my face to serve as a stool, finally figuring out that if I sat backwards, propping myself up with my arms and looking straight up, would do the trick.

I looked up and saw her beautiful body, her small but plump ass, her small perky tits, and her beautiful face looking down at me. She said "good. Now you are to keep your mouth closed and your tongue inside your mouth. Breath only through your nose. If I even THINK I feel your mouth open or your tongue slip out, I'm kicking your ass out into the hall in just your little panties, to find your way home, understood?"

"Yes, goddess." I quivered.

"Good," she said. "And you may have trouble breathing. That's normal." And with that she lowered her beautiful ass onto my face, with my nose sitting right in her little asshole. She wiggled her butt on my face to get a good seat.

For 10 minutes I struggled to breath as she put her makeup on while gradually putting more and more weight down on my face. A few minutes in, she started talking. "Remember, I like tall guys. Preferably dark skinned, well built, confident, and extremely well hung. I don't have a hard time attracting guys, as you probably know. So your job is simply to take me somewhere with hot guys, and make sure only the hottest, most hung guys are occupying my time. I deserve only the best. Right?"

"Ymph," I managed to say under her ass.

Finally, she stood up, stepped off of me and walked out of the bathroom. "Come help me get dressed," she said. She sat on the edge of the bed again, and I fetched her some more champagne. "Well done!" she said. I briefly felt proud. "Now go fetch my new lingerie."

For the next few minutes, I blissfully helped Penny get into her sexy new lingerie set. I slid her underwear on, fitted her into her stockings, and clipped her garters to her stockings. Finally, I stood up and fitted her into her bra, clasping it behind her. She turned around and did a little curtsy. "How do I look?"

"So fucking sexy, Goddess."

She chuckled, walked up to me, grabbed my ear and yanked it down so she could whisper to me. "That's right. And if you do a good job tonight, my little cuck, you'll get to see a real man rip this all off of me."

With that, she pushed me away and walked to her suitcase. "Now get dressed, but keep your panties on underneath. I'm ready for some dick, let's get out of here. Hurry up."

She slipped on an incredibly sexy dress and some heels, grabbed her little purse, and was ready before I was. I hurriedly got dressed and rushed to the door.

"Are you ready?" she smirked at me.

"Yes, Goddess."

She laughed. "We'll see. Let's go."

I opened the door for her and we stepped out.