Dating Penny Pt 04

Penny and I had dinner at a trendy Asian restaurant. It was strange being there with her, because on the one hand I couldn't believe I was sitting at a table with such a sexy woman, but on the other hand she spent much of the dinner speaking down to me or teasing me.

"I really need to get fucked tonight. Don't let me down, cuck."

"I won't, Goddess."

Penny took the liberty of ordering for me, and after ordering me an Asian spin on a panna cotta for dessert, she pulled a small sealable plastic cup from her purse and put it on the table in front of her. I looked at her inquisitively, nervously.

Then, without breaking eye contact with me, she reached under the table and shuffled herself a little bit. Finally bringing her clasped palms above the table.

"What have you been thinking about during dinner?" She asked. I wasn't sure if this was a trick question.

"Umm, well I've been thinking about how sexy you are and how lucky I am to be here with you."

She smirked. "Good. You know what I've been thinking about?"

I shook my head. She leaned closer and spoke a little softer.

"I've been thinking about a big stud ripping my new lingerie off and filling me up with his big cock. And making you watch what real sex looks like. What do you think of that?"

"That sounds amazing, Goddess." I gulped.

"Does it make your little dick hard?" she asked.

"Yes."

"Ha. Well I get it. I've been soaking through my panties thinking about it all dinner." And with that she opened her hands and her panties fell to the table. She had taken them off right in front of me. I immediately got even more hard but also nervous that someone would see. Luckily it was pretty dark.

She continued. "Smell them. Smell how wet I am."

I quickly grabbed her panties off the table and brought them to my nose in my fist, trying to be as discreet as possible. I sat there smelling her panties as she stared straight at me, smiling.

"How do I smell?" she asked.

"Amazing," I said.

"Just remember it's not you who makes me wet like that."

"I know, Goddess," I said.

"Now this is what you're going to do." She leaned forward again. "I want you to stand up and walk to the bathroom. Do NOT take my panties away from your face. And take this cup with you." She pushed the resealable cup towards me. "Go into the bathroom, let out your little dick, and jerk it to my scent and to the image of what got me wet. And when you cum into this cup and bring it back to me."

I continued to look at her, starting to shake from nerves and a strange excitement, checking to make sure she wasn't bluffing. She wasn't. I apprehensively reached over for the cup, stood, and walked quickly to the bathroom, feeling very odd and exposed while holding my fist to my face the whole time.

Once I reached the men's room, I rushed into a stall and finally took a deep breath, taking full stock of the situation I was in. Truthfully, I was hard. And when I looked down in the full light at the damp sexy panties in my hand, I got even more aroused. I had no idea what Penny had planned with the cup but I decided to just try and embrace the moment. I unbuckled my pants, all of a sudden remembering I was wearing panties myself. I took my dick out, pulled the panties to my nose again and started to jerk myself off. I closed my eyes and imagined someone ripping Penny's lingerie off, and having the privilege of being able to see her get fucked. Between the images in my mind and her aroma at my nose, I found myself on the verge of cumming within a matter of seconds. I then remembered the cup. I quickly fumbled for it, got the cap off, and placed it in a way that would catch my cum. I managed, clumsily, to do it just in time, and the relief was incredible. Penny had been teasing me so relentlessly that I had built up quite a store of cum, and I couldn't believe how much I was filling the cup. When I was done, it seemed that almost a third was full. I quickly caught my breath, put the cap on, and pulled up my pants. Not sure what to do with the panties, and wary of upsetting Penny further, I put them in my fist up to my nose again as I left the bathroom and returned to our table.

As I did, I noticed our dessert had arrived and Penny had started eating without me. I sat down.

"Well that didn't take long," she scoffed.

"Where's the cup?" Again, I was amazed how quickly she could turn stern.

I awkwardly pulled the cup from under the table and slid it to her, not fully believing I was sliding a cup of my own cum across a restaurant table.

She picked it up, seemingly unconcerned that someone might see. "Wowww, someone had a lot saved up. I honestly didn't know a pathetic cuck could even create this much cum. Good for you. Although...maybe not so good for you."

I looked at her suspiciously. She unscrewed the cap, swirled the cup and eyed towards my dessert.

"Pass that here."

I looked down at my dessert, and up at her. She had a devilish grin on her face. I started to realize what I was in for.

"Hurry up!" she yelped. I reluctantly pushed my dessert towards her. She grabbed it, continued swirling the cup, and then slowly poured out my cum all over my panna cotta. I was horrified. Both at people potentially seeing and about what was about to happen.

She let the final remnants drip out with a shake of the cup, put it down, pushed the plate towards me and folded her arms.

"Now I'm going to watch you eat every drop. Don't stop. Don't pause. Don't speak - just eat. Until every. Single. Drop. Is gone."

I slowly grabbed for my spoon.

"NOW," she emphasized.

I closed my eyes, gulped, and dug in. I tried to block the taste of my mouth, and swallow quickly, but what passed through my mouth could only be described as a mushy mix of salt and sweet. It was gross. I tried to distract myself by staring at Penny and taking in how sexy she was.

"Mmm, yum," she said. And then she giggled. "Do you know how pathetic you are?"

I knew better than to try and speak. She spoke forcefully, in a clear whisper.

"Real men get to fuck me. Pathetic cucks like you? You get to cum, alone, in a public bathroom, and then eat your own cum in front of me. Fucking sad. And tonight, while you help find me a real man to fuck me, I want you to continue to taste your own cum in your mouth, and feel your pathetically drained balls, and remember why you're never going to fuck me." She chuckled.

"Hurry up," she said. I tried to shove the remaining clumps of cum soaked food in my mouth.

I closed my eyes, took one last painful gulp, and set my spoon down.

"Don't forget all the juices!" she cheerily said, grabbing my spoon. "Here, I'll help you." She tilted my plate to the side and diligently scooped up the remaining disgusting juices. She held the spoon in front of me and said "open wide!"

I opened my mouth, she shoved the spoon in, and I sucked the last remaining cum off. "Gooood boy," she said, and smiled a devilish smile.

Just as she put the spoon down our waiter came over. "How did you like your desserts?"

"He LOVED his." Penny said, with a smile.

"That's lovely to hear. Anything else for either of you?"

"Just the check please," she said. I was relieved to be leaving.

I paid for dinner and we stepped outside. Penny walked towards the curb, turned around, crossed her arms and tapped her foot expectantly. "Well? Where are you taking me? I'm ready to see some hot guys. I'm sick of staring at you."

I panicked. In all the weirdness of dinner I had completely forgotten about my mission for the evening: find a place to take Penny where she could find a hot guy to fuck her. I Iiterally hadn't thought about it for a second.

"Don't tell me you haven't thought of anything," she scoffed, "I'll ditch you right here on the curb."

"No no! I'm just deciding which to take you to!" I mustered.

"Well decide faster."

I gestured for us to walk down the street, pretending I was going somewhere in particular. As we walked, Penny held onto my arm, and for a moment we felt like a real couple. It felt blissful, for a moment. But I needed to focus. It was too late to try and take her to a club. I hadn't booked anything and we'd end up standing in line all night. And I couldn't just take her to a random bar, because there is no guarantee there'd be any hot guys there. And then I remembered a place in my old part of town. It was a bar that on weekends had a DJ who spun hip hop, and it often had a line of people trying to get in late into the night. Most notably, the clientele tended to be primarily young black and Latino, which I expected was more of Penny's type.

"So the place I have in mind is a short cab ride away, is that ok?"

"Then why the fuck are we walking?" she asked.

"Sorry, Goddess, just it's easier to get cabs just up ahead." She rolled her eyes. She could see right through me.

We walked a few blocks up and I hailed a cab, and told the driver the intersection, and we were off.

As we rode, Penny took out her phone. Soon I started seeing her texting, wondering who she was talking to. Wondering if she was telling them how she had recently humiliated me over dinner.

"Ugh this guy won't stop texting me," she complained. "I fucked him once and he won't leave me alone." I was already jealous of this guy.

"Sorry, Goddess," I commiserated.

"He keeps sending me pics of his dick. Like, ok dude you have a nice, huge cock, that's why I fucked you, but I'm not trying to see that blowing up my phone all the time." Again, a tinge of jealousy hit me.

"Although I guess it's better than seeing your little dick," she scoffed.

"Yes, Goddess."

"Next time I have a one night stand I should just give the guy your number and pretend it's mine. Then you can receive all their dick pics for me. OMG that's actually fucking genius," she said. "You get to see the kind of dicks that get to fuck me, and I'm spared all the bullshit. What do you think?"

"It's a smart idea, Goddess," I said.

"Damn right. Fuck. I love it. And you can act like me and string them along just in case I do want to fuck any of them again. You'll be my little...cock manager. Little-cock cock manager!" She laughed out loud.

"Sounds good, Goddess."

"Mmmm, hahahaha." She leaned over and affectionately laid her head on my shoulder. The whiplash between humiliation, scorn, and affection was truly messing with my emotions.

The cab pulled up. We had arrived.

The line wasn't as long as usual outside the bar, maybe we were early. But it looked crowded inside, and the clientele looked promising. Penny showed no opinion on her face. We just got in the short line as she gauged the situation. Before long, we were let in.

The bar was crowded, and I definitely looked out of place. It was mainly black and latino guys, with a definite 2:1 ratio of men to women. People were half mingling around the bar and half dancing to the DJ. Penny and I found our way to a tall table next to the wall and checked out the scene. She said, without looking at me, "you might not have totally fucked up." I felt a sense of pride. Then she looked at me. "Get me a drink. A vodka soda."

I left her there and made my way to the bar. It was crowded and I definitely had to try and be aggressive to get to the front of the bar. It didn't help that most of the guys were bigger than me and all seemed to know each other. Finally I reached the bar but of course the bartender was ignoring me. Finally I got a drink for myself and Penny and returned to our table. As I emerged from the crowd around the bar I noticed three black guys hovering around our table. As I got closer, I noticed one talking to - or perhaps at - Penny. She seemed mildly disinterested.

I returned her drink to her, she nodded in benign appreciation, and the guy talking at her gave me a dismissive glance. I stood nearby - somewhat awkwardly - and let them chat. Eventually the conversation dried up between the guy and Penny and I reinserted myself. I was a little disappointed that she didn't seem interested in these guys - I wouldn't know what else to do to find her someone.

"What do you think of this place?" I asked.

"It's pretty good," she said. "But those guys were annoying."

"Sorry," I said.

"It's fine. But eventually I will want you to be able to tell when I'm not interested in someone and get rid of them for me. You shouldn't be completely worthless."

I was just glad there was an 'eventually'.

"Of course, Goddess."

She turned to face the crowd around the DJ area as she sipped from her straw. "I like him."

I looked in the direction she was looking. "Who?"

"Who do you think?" she said.

There were a bunch of guys, but one did stand out in particular. He was young, black, handsome, and wearing jeans and a dark blue t-shirt that showed off a lean but well-built frame.

"The guy in the blue shirt?" I asked.

"Mmm hmmm," she said, still staring in his direction. "I want you to go over to him and tell him I want to fuck him."

"What??" I said, shocked. She turned and glared at me.

"What's the problem? I told you your task would be to find me hot guys. I'm doing half the fucking job for you. Are you not even going to do this? Are you that fucking useless?"

"No, Goddess. I just.. don't know how he'll react."

"Well he'll probably think you're pathetic. But are you saying he won't react well to me wanting to fuck him? Is that what you're saying?"

"No, no, I guess it's just the first part."

"Well you ARE pathetic. So what?"

I stared at her silently.

"GO!" she said, sternly.

I walked away from the table, my heart beating heavily. I tried to stall but there was nowhere else to go. I walked straight toward the man Penny wanted, and luckily he was standing looking at his phone, allowing me a way to interrupt him without others noticing. I walked up and stood near him, hoping he'd look up. He ignored me. I looked back towards Penny and her glare was intensifying. I knew I just had to go for it.

"Uh, hey, excuse me."

He looked briefly up from his phone but assumed I wasn't talking to him. Again, "hey, yea excuse me?"

He looked at me suspiciously.

"You got a second?"

He continued looking at me suspiciously. I kept talking.

"I'm, uh, I'm here with my friend, Penny, over there." I pointed to Penny in the corner. He looked briefly but then back at me, still confused.

"She, um, she wanted me to tell you, or let you know..." he kept staring at me, more confused, "uh she said she wants you."

He was taken aback, but then chuckled. "What?"

"Penny, my uh, my friend over there, wanted me to tell you that she wants you."

He looked over at her again and really took her in. He started to get the message, "Wants me to what?" He turned and slightly grinned at me.

"Uh, I think she wants, I dunno, I think she wants to like, hang out with you." I couldn't say what she wanted me to say.

"Uh huh," he said, looking back in her direction, smiling. They were making eye contact. "And who are you?"

"I'm just her friend. Her name is Penny."

"Penny, eh? OK. She's a dime, for sure. I'd be happy to hang with her."

"Ok," I said, not sure what to do next. Then my natural submissiveness kicked in. "Uh, do you want a drink? I can bring you two each a drink."

He looked at me strangely, but took the offer and chuckled. "Uh, fuck, sure, get me a bourbon, straight up."

"Got it." I shuffled my way to the crowd at the bar. Out of the corner of my eye I tried to see if he was going up to Penny. It took him a minute, but eventually I saw him walk over to her table. They were now behind me and I had to focus on getting close to the bar. Soon I was in a crowd trying to get the bartender's attention again, and it took forever. Probably about 15 minutes later, I had three drinks and emerged from the crowd at the bar. I saw Penny, still standing at our table, with the man standing beside her, whispering in her ear while he rubbed her ass. She was sipping the remnants of her last drink and smiling. I walked over to them. I put the two drinks on the table and stood on the opposite side of the table from them. She looked at me while he continued whispering to her and rubbing her butt. He caught my (and the drinks) presence out of the corner of his eye and turned around.

"Alright! Thanks cuck!"

Penny burst out laughing. The man smirked and grabbed his drink. My face must have showed a mix of horror and confusion.

"Your girl blew up your spot. Sorry bro. But it's all good. You're not the first cuck I've met. Cucks like you can go to good use."

They looked at me, continuing to smirk. I didn't know what to do or say.

Penny chimed in. "He's still trying to prove himself as a useful cuck. He's at least pathetic enough."

They chuckled to themselves. Then Penny grabbed the man's arm excitedly and leaned up to his ear. She started whispering to him. She pulled away and they looked at each other. She laughed. "I think it would be hot," she said to him, pleadingly.

"You're a freak, girl." He laughed. "But sure, why not. I don't mind putting white boys in their place."

My heart sunk, not knowing what was about to happen. "Meet me in a few, cuck." He walked away from the table. I was really confused.

Penny was smiling ear to ear. "My eye for dominant guys is just as good as my eye for pathetic cucks, I guess. Lucky you. Here's what's about to happen: you are going to meet James in the bathroom, and you will take a selfie of yourself and him and text it to me."

I was still really confused. "A selfie?"

"Yes - you know what that is right? Are you kidding me?"

"Of course, I'm just - "

She cut me off.

"You'll figure it out. It's not that hard. James may have some more directions hahaha."

I looked at her while she giggled to herself and sipped her drink. She then leaned towards me like she was going to kiss me, I leaned close and she stopped right in front of me. "Regardless of whether you do what you're told, I'm going to fuck James tonight. But if you're a very, very good cuck, we might let you watch, or listen. Do you want that?"

"Yes Goddess."

"I thought so. So do what you're told, by James too."

"Yes Goddess."

"Now go!"

I hustled towards the bathroom, excited for the potential to watch Penny and this stud fuck.

I walked into the bathroom. It was pretty small and dingey, still pretty noisy from the sounds of the club. There was a man using the urinal, it wasn't james. There were two stalls, a regular and a handicap. I looked around, no James. Then I ducked down slightly to see there was a man standing in the handicap stall. I assumed that was James. I waited. The man using the urinal left. I continued to wait.

"Cuck?" I heard coming from the large stall. My heart dropped. I looked around. It was just us. "Yes?"

"In here," he said. I heard the stall door unlock. I pushed on it slightly, saw him standing there and walked in. I shut the stall door and locked it behind me. James began to talk, in a loud enough voice for anyone else who might come into the bathroom to hear. I was terrified.

"Your girl wants a picture."

"Yea," I said.

"Alright," he said, and reached down and started unbuckling his belt. My heart sank again, what was going on?

"Uhhh..." I mumbled, and stumbled for the door as if trying to leave."

"What the fuck are you doing?" he said. "She said she wants to see what I'm working with, and wants you to take the picture."

"Oh, uhhh, got it," I said, as if that made more sense, "she just told me to take a selfie."

He paused and then started cackling. "Ohhh hahaha. Got it. I got you, I got you." He continued to unbuckle his belt just as he had before. He then slowly reached into his underwear, shuffled slightly, and pulled out his dick. He let it drop outside his underwear and I stood and stared, in awe. He must have been 6 inches fully flaccid, and extremely thick. He picked it up and let it rest in his hand. "Get a good look, cuck. There's a reason you're in here taking pictures and I'm gonna be the one fucking your girl tonight." I was shocked how quickly this random guy we had just met was falling into the dominant role. He clearly had experienced this dynamic before.