Dating Penny Pt. 01

Her profile picture was unusual, but it caught my eye. For one, she had most of her face obscured, but I could still see her pouty lips and jet black hair. Also, she was posed in a more "flirty" way than most profile pictures - lying on her stomach with her heels in the air behind her.

I clicked.

Her profile was straight to the point:

"I am looking for a cuck. Message me if you are fit, have a good job, and are ready to spoil a Goddess."

My stomach immediately tightened. For years I had had secret cuckolding fantasies, but had little success getting my partners to engage with me in this area. I had also tried unsuccessfully to find women online who wanted a cuckold relationship. I was starting to think it was a pipe dream - but then I stumbled on this. Could this be exactly what I'm looking for? Worth a shot.

I composed myself and sent her a message:

"Hi there - Brandon here. Your profile caught my eye. I have long sought a cuckold relationship, and would love to hear more about you and what you are looking for."

After I sent, I obsessively refreshed the direct message chain to see if she saw my message. Then, only a few minutes later, I saw she logged on. I got a "read" receipt. Then, a notification that someone looked at my profile. I anxiously awaited a response. But nothing came. She logged off.

How could she dismiss me so quickly? She wasn't even willing to talk to me? How could she already tell that I wasn't what she was looking for. I felt deflated and frustrated. After more than an hour of obsessive refreshing, I logged off and tried to distract myself.

Right before bed, I logged on again. Still no response, even though she had since logged on again. Then all of a sudden I see a green dot on her profile - she was online. Again, I obsessively waited, but nothing came in. Finally, as a last ditch attempt, I messaged her again:

"Hi there. Just wanted to say, I am very serious about finding a cuckold relationship. I would love to hear more about what you're seeking, and at the very least we may find we have similar interests. Hope to hear from you."

Almost immediately, she read it. Then, a minute later, a response.

"Are you married?"

That's a weird response, I thought. I wrote back right away.

"Nope. Single."

She wrote back right away again.

"Good. I have had problems with married men reaching out to me. So tell me more about you, Brandon."

"Well I'm in my late 20's. I work as a consultant. I have desired to be in a meaningful cuckold relationship for as long as I can remember and am finally ready to make it a reality. What about you?"

"That's good to hear. I am looking for a cuck to treat me like the Goddess I am. I want to be spoiled and taken care of. And I don't want any BS or drama."

"No drama from me. :-) I would love to spoil you and take care of you."

"Good. :-) Here's my number. Send me another picture."

Wow - I already got her number. I quickly found another photo of myself, and sent it over.

"Here's another pic," I said as I sent it.

"Goddess," She replied.

"What's that?" I said.

"You will always address me as Goddess."

"Got it. Will do, Goddess."

"Good. Not too happy that you're fucking up already, tbh."

"I am sorry Goddess, it won't happen again." We're only 15 minutes into chatting and I'm already subservient to her. The conversation is getting me hard.

"Thank you for the pic. You need to work out, I like my cucks very fit. But this will do for now."

"I would be happy to get in better shape for you, Goddess."

"Good. Are you hung?"

"I am average size."

"What's average size?"

"6 inches or so."

"Lol. Average for you, perhaps. I like hung guys. Don't you think I deserve hung guys?"

"You do, Goddess."

"So why do you deserve to be my cuck?"

"Because I will spoil you and take care of you and always do what make you happy."

"Goddess."

"Goddess! Sorry!"

"You really are a fuck up, aren't you."

"Yes, Goddess. I am sorry, I will do better."

"Good. I am going to sleep. So are you going to ask me or what?"

"Ask you what, Goddess?"

"Ugh. Are you going to ask me out or not?"

"Oh, I'm sorry Goddess. Would you care to accompany me on a date?"

"Yes. Next time don't make me wait. Friday, take me out. Find a good restaurant, and expect to take me out afterwards. Talk to you soon."

"I will, Goddess. Sleep well!"

I couldn't believe it. 30 minutes prior, I thought I was going to be fully ignored, and now I had a date scheduled with someone who wants me to be their cuck. I couldn't believe it. I immediately started researching good restaurants. I hadn't been so excited for a date in ages. It was hard to fall asleep as my mind raced with what was to come.

---

When I woke up, I picked up my phone, and saw I already had a text from her.

I am excited for our date Friday. Have you selected a restaurant yet?"

"I have. I made a reservation." I sent her the link.

"Ugh, and I had to ask you."

"I am sorry Goddess. I am excited too."

"Good. But if you keep fucking up I'm not going to bother."

"I am sorry Goddess. It won't happen again."

"OK. I expect a gift on our first date."

"Of course, Goddess. What would you like?"

"I like fancy lingerie."

"Wow, I would love to get you nice lingerie."

"Nice panties would make me happy. I am a size small."

"Thank you, Goddess :-)"

"OK now fuck off."

"Have a great day, Goddess."

No response. Less than 24 hours into my "relationship" I was already suffering whiplash. But I loved it.

She didn't text me again all day. I spent the day shopping for panties, something that was very new to me. It was not as easy as I thought. I ordered a pair that I thought she would like and made sure they would arrive overnight, as it was already Wednesday.

---

The next morning, I woke up early and texted her:

"Good morning Goddess."

"Good morning," she responded immediately. "I am looking forward to our date tomorrow."

"I am too, Goddess."

"Did you get me something?"

"I did, Goddess."

"Good boy. You might not be such a fuck up, after all."

"I try :-)"

No response. I decided to leave her alone so as not to arouse her anger. Before bed, I sent one more text:

"I Hope you had a great day Goddess, I am very excited to meet you tomorrow."

"Likewise. Good night," she responded after a few minutes.

I struggled to sleep. I was so excited.

---

On the morning of our date, I awoke to a text.

"Good morning. I look forward to seeing you later. I hope I like my gift."

"Me too, Goddess."

The day was enormously unproductive. I was jittery from the excitement. I left work early to get ready, struggling to decide what to wear. What does a cuck look like? I got a haircut and tried to look as put together as possible. I went to a nice store to get a gift box and tissue paper for her gift. Our dinner reservation was at 7. I showed up at 6:45 and paced outside with excitement, holding the gift in my hand. At 6:50, my phone lit up.

"Running behind. Please get our table and order me a drink. I like mojitos."

"Will do, Goddess."

I got our table and sat nervously. Then, at 6:12, she walked in. She was short, no taller than 5 feet. She was asian, with jet black hair and a petite body. She seemed to already know who I was - maybe there is a "cuck" look after all. She walked up to me, slowly.

"Brandon?"

"Yes."

"Hi," she smiled, her face was gorgeous. "I'm Penny."

"Nice to meet you, Penny."

She took off her coat. I tried to hide my reaction to how stunning she looked. She wore heels, black leggings, a short, tight leather skirt with a navy blouse tucked in. I couldn't believe how good looking she was.

Unlike our text exchange, the dinner felt like a real "normal" date. She didn't ask me to call her Goddess. She didn't get mad at me. We didn't even talk about the basis behind this potential relationship: that I wanted to be her cuck. At the end of dinner, I realized I hadn't even given her her gift. I mentioned I had it for her.

"Good," she said. "You can give it to me at the bar you're going to take me to."

Shit. I had completely forgotten to find somewhere to go afterwards. I played coy, said "Of course," and excused myself to the bathroom. I quickly searched for an upscale bar and found something a few blocks away. After I got back to our table I asked if she'd like to get a drink with me nearby. She smiled and said yes, and we started walking.

Thankfully the walk was short, because we seemed to run out of normal conversation. It was getting a little awkward. Was either of us going to break the "cuck" ice?

The bar was nice, but a little empty. We sat down and a waitress took our orders. I took the opportunity to give Penny her gift.

"I hope you like it," I said as she opened the small box and dug lightly through the tissue paper.

She didn't react much as she pulled out some satin, light pink panties. But she was smiling slightly.

"Thank you, Brandon. I will say, however, I prefer something a little sexier."

"Oh, I'm sorry. I would be happy to return these and get you something else."

"You can get me something else. For now, I want you to take these, walk outside, and throw them in the trash can on the corner."

I paused, I was a little surprised by this request. But she was serious. I said "Ok," quickly repacked the gift and walked outside to throw them away. I came inside and she was unfazed. Coyly drinking her cocktail. Finally, she broke the ice.

"So, have you ever been a cuck before?"

And with that, we were off to the races. I told her about my experience trying to bring up my cuckold fantasies to exes, and how they were all horrified. I told her about trying to get women I had dated to play around with this fantasy and how it never really went anywhere. I told her about the kind of things I fantasized about, but kept it pretty tame. I didn't truly reveal the depravity of my fantasies. She listened intently and asked polite questions. Then, after our drinks were done, she said "take me dancing."

I probably looked like a deer in headlights. I had no idea where to go dancing, that wasn't my typical scene. She could tell.

"I know a place," she said. "Get the check and let's go."

I got the check and paid for our drinks while I panicked inside. I can't dance. Did she expect me to dance with her? I felt very uncomfortable.

We started walking, with her leading the way. We get to a bar/nightclub-type place, with a very small line to get in. As we waited in line, she sized me up: "You look nervous," she smiled devilishly. "Don't worry. It will be fun. And you should know: I love dancing."

I smiled nervously. We went in and I was relieved to find that it was really more of a bar than a dance club. We headed near the bar and I ordered more drinks for us. After I handed her her drink, she gave me her coat and her handbag. "Hold these for me," she said. Strangely, I got slightly hard in response to this command. She looked gorgeous as we surveyed the scene of the club.

All of a sudden she leaned close to me, still with her eyes on the dance area. "He's hot," she said. It was pretty clear who she was talking about. A muscular black man was dancing with an attractive white woman about 10 yards away.

"Is that your type?" I asked.

"Mmhmm," she said. "I like dark men. Muscular. Tall."

"A little different than me," I nervously joked. She looked at me. "You're a cuck. You're useful for other things. You'll see." I smiled.

After a few more minutes of watching this attractive man dance, the song ended and he and his partner split ways. All of a sudden, Penny said "go tell him I want to dance with him."

"What?" I said, more than a little caught off guard.

She turned to me, and was now more forceful with her words. "Go over to him, and tell him that I want to dance with him."

I felt uncomfortable, I didn't know how this would look. It sounded incredibly awkward. But she was clearly serious. She stared at me - no longer smiling.

"Uhhh, ok, well, what should I say?"

"I just told you what to say."

"Uhhh, ok. Ummm," I was clearly stalling.

"Are you worried he won't want to dance with me?"

"No, of course not! I just, I don't know, it feels a little weird."

"Do you want to be my cuck?"

"Yes, of course."

"Well this is one of the things my cuck does. He asks hot guys to dance with me."

"Got it. Ok." She was still staring at me.

"If you don't go and ask him to dance with me right now, you can fuck off and never message me again." That was all I needed to be pushed into action.

I put down my drink and handed her back her coat and handbag. She took the coat but pushed the handbag back to me. "Take that with you. It's girly and makes you look like the cuck that you are."

Humiliated, I gave up any pretense of pushing back. I accepted my role. "Ok," I said, and walked over, sheepishly.

This handsome man was sitting on the edge of a banquette, scoping out his next kill. He was sort of with a group of people, but lucky for me he was separate enough that I could go up to him without having his whole group hear. I approached and got his attention.

"Excuse me, sir?"

He looked up at me, and didn't seem too happy that a guy was speaking to him.

"Hi, apologies, this may sound a little odd, but see that woman over there?" I nodded in Penny's direction. She was looking straight at us - sexy as ever. The man looked. "Yea," he said.

"She is wondering if you'd like to dance with her."

He looked at her again. Then he looked at me, sort of sizing me up. He saw me holding the handbag and raised an eyebrow. "Are you, like, her friend or something?"

Sensing an escape from the awkwardness, I said "Yup, she's my friend. She's just a little shy."

He still looked a little bewildered. But he finally said "Your friend is super hot. Sure. Bring her over."

I signalled to Penny, and she walked over slowly, as if everything was going according to plan. She held out her hand and introduced herself. "Nice to meet you," she said. "I'm Penny."

"Good evening Penny, I'm Rob," the man said as he took her hand. He scooched over. "Would you like to join me for a drink?"

"I would love that," she said, smiling, as she plopped down next to him. He immediately put his arm over her shoulders as I stood near them, awkwardly.

"Hey babe," she said, looking up at me, "why don't you go get me and Rob a couple of drinks?"

Rob looked a little bewildered again, realizing finally I'm not really just a "friend" of Penny's. He chuckled to himself. I say "sure" and ask Rob what he would like. In a half laugh, he scoffs at me "tequila on the rocks," and pulled Penny closer to him. She nuzzled up. She looked so hot. I walked to the bar.

As I waited at the crowded bar I occasionally looked back at them. They were smiling and laughing. She was into him in a way she clearly wasn't with me while we were at dinner. She was actively flirting with him, touching his knee, flicking her hair back sexily every now and then. I felt invisible in the crowded club - completely ignored. In that odd moment of isolation I reflected on the fact that I was only a few hours into a first date with a gorgeous woman, and she was already "cheating" on me with another guy who I totally can't compete with. I was feeling humiliated but also excited. I had never felt this way on a date before, and I kind of loved it.

I finally got the drinks and headed back to where Penny and Rob were. The flirting had been turned up to 10 and they didn't even notice me approach. I put the drinks down, and Penny looked up at me and said "thanks babe! Rob and I are going to go dance. Watch our stuff." And with that she excitedly pulled Rob onto the dance floor.

I stood there, again holding her coat and handbag, as I watched Penny dance with Rob. She looked so incredibly sexy, I immediately got fully hard. I used Penny's coat to hide my clear erection as I watched her sexy body writhe up against Rob's. It was such a hot sight.

I stood there, entranced, humiliated, and with pre-cum dripping from my cock as I watched them dance and, eventually, start making out on the dance floor. They completely ignored me.

After what seemed like forever, they returned to the table. They were both covered in sweat from dancing. They sipped their drinks as they caught their breath - still blissfully ignoring my existence. She said to him "Oh yea, let me get your phone." He smiled at her and handed her his phone. She started typing what I could only guess was her phone number. She handed it back to him. "It was great meeting you, Rob. Call me." He smiled back. "I definitely will," he said.

She started walking away and I gathered that I was supposed to follow her. She finally acknowledged me.

"That was fun. I'm ready to go home now."

"Oh, ok," I said, clearly flustered.

"Did you have fun?" she asked.

"I did."

"Good," she said, and gave me a devilish grin. "Close your tab and meet me outside. A good cuck walks his Goddess home."

"Of course," I said. I closed my tab and met her outside. The cold air was a welcome reprieve from the stuffy, sweaty club. I put Penny's coat on her and handed her her bag.

"You did pretty good for a cuck," she said, and started walking. "Rob had a huge cock. I could feel it through his pants. Just the size I like. But you don't deserve the privilege just yet of seeing me go home with another man. That will happen in time. Plus, I like teasing all men. Not just my cucks. So Rob will have to wait to fuck me."

I walked silently next to her, incredibly turned on. She lead me to her apartment building and said "OK, I'm here."

She turned to me. "Thanks for a great first date. You're cute."

"I had a great time, Penny."

"Good," she giggled. "Same time next week?"

Amazed, I excitedly said "Yes! Definitely!"

"Good. Let's take things to the next level. Good night, cuck."

And with that, she turned around and sashayed into her lobby, leaving me in the cold and without even a single kiss.

I couldn't wait until our next date.