Dating Penny Pt. 02

On Saturday morning, I sent Penny a text thanking her for such a great date.

"I too had a great time," she wrote back. "I am excited about what lies ahead for us. I think this could be a good relationship."

Before I could write back, she followed up.

"Next Saturday is our next date. Book a hotel room for Saturday night. It must be nice. Pick me up at my apartment at noon. Don't fucking text me until then. See you next weekend."

"Yes Goddess," was my reply. She did not respond.

I was so excited. A hotel room! Would this mean I would get to spend the night with her? My mind raced with anticipation all week. It was so hard not to text her, but I behaved.

---

On Saturday morning I still hadn't heard from Penny, but I made sure to get to her apartment building early. At noon on the dot, I texted her:

"I am downstairs, Goddess."

"Good boy. I am coming down," she said.

A few minutes later, I saw her coming out of the building. She was wearing an elegant wool coat that covered up whatever else she might be wearing, other than her black leggings and heels. She had her hair pinned up, and was carrying a small purple quilted day bag.

"Good morning boy. You can carry my bag." She handed me her bag and started walking down the street.

"You are taking me to lunch. I did you a favor and made a reservation at my favorite restaurant."

"Thank you, Goddess," I said.

"After lunch, you are taking me shopping. I need something sexy to wear tonight."

"Yes Goddess."

"Did you book a hotel room?"

"Yes, Goddess."

"Good. Our evening will begin there. But later you are taking me out."

"Yes, Goddess."

We continued to walk to lunch. As we arrived at the restaurant, I realized that today was going to be an expensive day for me. We got to the table, and the waiter took Penny's coat. I then got to see that underneath her coat she was just wearing a short, tight black dress over her black leggings. We sat down, and Penny took the liberty of ordering for both of us.

As we waited for our food, Penny lightly teased me about our first date. For the first time in person, our conversation turned sexual.

"So, tell me, did you enjoy watching me and Rob dance last weekend?"

"I did. Very much."

"Good. A lot of what you will be doing is watching."

"What else will I be doing?" I pressed. She smirked at me.

"You'll find out. Baby steps. But always remember: everything you do is for my pleasure first, understood?" Her smirk disappeared.

"Understood, Goddess."

"Good. And speaking of my pleasure, last night you will be happy to know that I saw Rob again."

I immediately started getting hard. "Oh, really?" I asked.

"Mmhmm." She started teasing me with her eyes.

"Did you..."

"Fuck him?" She completed my sentence. "Yes. He actually left my apartment less than an hour before you picked me up."

As we talked, our food arrived, including the soup that Penny ordered for me.

"In fact," she said, lowering her voice to a sultry whisper, "right before he left, I sucked his huge dick one more time."

I gulped.

"Oh, perfect," she said, eyeing my soup. She pulled the bowl towards her slightly and leaned forward. All of a sudden, she pursed her lips and slowly let a long stream of saliva right into my soup, and silently pushed it back to me.

"Now you can taste what I taste: Rob's leftover cum in my mouth." She smiled a devilish smile.

"Eat up."

She watched as I slowly picked up my spoon. I looked up at her.

"Every. Drop. I'm watching."

I proceeded to eat the soup as Penny watched. Not a word was said for the rest of the meal. I tried not to think that I was eating a mix of Penny's saliva and Rob's cum, but couldn't help getting hard while I ate the disgusting mixture. All the while, Penny ate her lunch, sipped her wine, and shot me evil smiles.

When I finished, she said "show me the bowl." I turned it sideways to show nothing was left. "Good boy."

The check came. "Thanks for lunch. Let's go shopping!" And we were on our way.

---

Penny led the way, again. I held her bag and tried to catch up. I was nervous about asking too many questions, so I simply followed. Finally, she let me in on what was planned.

"I need a hot dress for tonight, and you're going to buy one for me."

"Yes, Goddess."

"I've been meaning to check out this store for a while, their stuff is really hot."

As she stepped into a trendy-looking boutique, she turned to me:

"You will watch and assist. You will not speak unless spoken to. At the end, you will pay. Got it?"

"Yes, Goddess." She turned and walked in. I followed.

I don't think I had ever gotten turned on just watching someone shop before. But seeing Penny sift through sexy dress after dress, and imagining what she would look like in each, was a surprisingly hot experience. Not to mention, I was getting turned on by the subtle humiliation of having to hold all the dresses she was going to try on.

Eventually, Penny asked to use the dressing room, and an employee led her to a small, curtained room in the back of the store. The employee took the clothes from me and hung them up in the room. Penny thanked her and then walked in, gave me a smirk and pulled the curtain shut. I found a small bench outside the dressing room to sit on, and I silently watched clothing fall from Penny's waist and a new dress get pulled on, one after one. It was torture not being able to see everything.

Finally, after what seemed like forever, Penny emerged just as she looked before.

"I'm ready," she said. I was really disappointed that I didn't get to see any of the dresses on her, but I didn't say anything. I followed her to the front of the store where she put two dresses on the counter and made small talk with the owner. When the full price came up, $1,376.84, both the owner and Penny shot me a look. I took out my credit card and paid. I didn't say a word. Penny said a cheery "thank you!" to the store owner - not to me - and I followed her out.

As we walked down the street, Penny said "I couldn't decide which dress was hotter so I let you buy me both."

"Of course, Goddess."

"But don't worry, there's still more shopping to do." I gulped, not knowing what kind of financial torment I had got myself into. And then a few minutes later, Penny slowed in front of a fancy-looking store with a french name. It had a doorbell, which she rang. As we waited to be let in, Penny said to me "this will be a little more fun for you." And then the buzzer opened and we stepped in.

I immediately realized we were in a lingerie store. It didn't seem like any other patrons were there, just three incredibly attractive female employees. They swarmed us, in the politest way possible. "Welcome! How are you! Can we take your coat and your bags? Please, look around, let us know if you have any questions!" Another one of the employees said "would you each like a glass of champagne while you shop?" Penny responded, "I would love a glass. Brandon here, will NOT have one." The employee shot me a funny look. "Of course, I will be right back with that for you."

Penny started to look over various incredibly sexy lingerie sets on the wall, while I tried to remain as invisible and as least awkward as possible. After Penny got her champagne I could tell the three store clerks were watching me, trying to figure out the dynamic. I found a place to sit in the middle of the store which relieved some of my awkwardness. Then all of a sudden I heard "Brandon! Here!" I hurried over. "Hold this," she said, and handed me her half-drank glass of champagne. She then turned and held up a white lace bra and panty set over her petite frame. "How fucking hot is this?" she said. Finally spoken to, I responded: "Very hot, um, Goddess." I spoke the Goddess part a little quieter so the clerks couldn't hear.

"I know, right? With a garter and stockings? I have to try it on. Come on." Penny walked towards the back area of the store and I followed. One of the clerks hurried over. "Hi there - thinking of trying this set on?"

"Yes," Penny said. "And do you have matching stockings and garter for this?"

"Of course," the clerk said. "Take any of the dressing rooms and I'll bring that right over."

Penny walked into a dressing room, again just a room with a large curtain instead of a door. I waited, but this time she turned around and said "Well? Are you coming in or not?" I hurried in. She gave me a devilish grin. "Sit there," and pointed to a little bench inside the dressing room. The clerk hurried over with the matching items, "let me know if you need anything else!", and then pulled the curtain shut. It was just me and Penny in a dressing room.

I was still holding Penny's champagne, which she grabbed and took a sip, and then handed back to me. Then she started to undress in front of me. First, she slid off her black heels, and as she stepped out of them I for the first time realized how tiny she was. Then, she unzipped the back of her black dress and slid it down her body until it fell to her feet. She ignored me, standing only in her black leggings and black bra as she picked up the white lace lingerie bra. She turned to face the wall so I couldn't see her chest, and I watched her reach back, unclasp her bra, and let it fall down her arms. Then she pulled on and clasped the white lingerie bra.

Penny stayed facing the wall as she slid her black stockings down torturously slowly. As she bent down to pull them off her tiny butt pointed straight at me. I was dying. I watched her gingerly slide the new white panties on, and then she turned around, did a little sashay and said "how do I look?"

She knew the answer.

"So incredibly hot, Goddess."

"I agree," she said. "Let me try on the rest."

I then watched as she pulled on the garter and her stockings. Suddenly, before clipping them together, she walked over to where I was sitting and said "would you like to clip my garter to my stockings?"

"I would love to, Goddess." She giggled. I had never done this before, and I was in a total state of shock at this beautiful woman asking me to dress her in lingerie. My hands were shaking, but I figured it out.

When I was done, she made some adjustments, and then opened the curtain to look at herself in the larger mirror in the dressing area. She looked incredible. One of the clerks was there, and said it was a perfect style for her. Penny was sold. "I'll take it," she said. Then she added, "oh but, do you have the panties in pink?"

"I can check, but I believe so," the clerk said.

"Great, what size do you think he is?" she nodded in my direction.

The clerk looked at me and then back at Penny, a sly smile coming onto her face. "What size for the panties?"

"Yes," Penny said, matter of factly. "He wants a pair of the panties for himself. In pink. What size do you think?"

The clerk chuckled disdainfully at me, but knowingly with Penny. "I think I know, one second." The clerk left the broader fitting area as I stood there like a deer in headlights, my mouth agape, Penny staring at me with a devilish closed-mouth grin, her hands on her hips, in her brand new lingerie. I didn't know what to say. Penny just turned to face the mirror and fixed her hair as she said "I saw you admiring my new panties. Only fair you get something for yourself."

The clerk came back, now conveniently trailed by the two other clerks. She had with her a larger pair of pink lace panties on a hanger. "I think these will fit," she said, eyeing my body up and down.

"Great, thank you," said Penny. "Brandon, why don't you try them on?" I looked at Penny, still in shock. Penny didn't have a smile on her face anymore, but the three clerks did. I knew there was only one option. I grabbed the hanger from the clerk and walked towards the curtained stall, but Penny said "noooooo, right here. For all of us to see. Strip and put on your pink panties, boy."

My heart dropped into my stomach - I was so humiliated and nervous. The clerks were giggling. Penny looked incredible. I sort of blacked out, but I have a vague recollection of taking off my clothes right then and there, letting them pile on the floor. Before I knew it, I was standing completely naked in front of these four gorgeous women, looking for where I put the pink panties I was supposed to try on. As I fumbled around, Penny said "the size looks right, it doesn't look like there's much to fit in there." The three clerks laughed more audibly.

I finally found the pink panties and pulled them on, trying to stuff my genitals within the boundaries of the fabric. But as I fumbled with the lace, I inexplicably started getting an erection. I tried to move my body in a way to hide this fact, but it was no use. "Let me see," said Penny, after she could tell the panties were on. I turned around and they all started laughing out loud. My erection was being held up to my body under the waistband of the pink panties, and I looked ridiculous.

"They are perfect, he'll take them! Brandon, keep the panties on and get dressed. I'll meet you up front."

I was beet red. The clerks dispersed, in hysterics. Penny went to go take off her new lingerie set. I was left in the common area to pull on my clothes over my new pink panties, my hard on finally subsiding. Too little too late.

I sheepishly arrived at the front of the store where the clerks were still giggling at me as they ran me up for my and Penny's new underwear. I didn't say anything, I kept my head down and gave them my credit card. "Enjoy!" one of the clerks said mockingly as she handed me back my card. Just then, Penny emerged from the back, they folded her new lingerie and put it in a bag. We left. As we stepped out of the store Penny was still laughing to herself. I walked quickly in any direction I could, trying to distance myself from the humiliation.

Penny yelled "hey!" as I got too far ahead of her. I turned around and she sashayed up to me. She stood right in front of me, her body right up against mine, about 6 inches shorter than me even in her heels. I looked down at her, she looked up at me and then she ran her finger down my chest to my crotch. She grabbed my genitals with enough force to make me tense up, and looked up at me again.

"Lost your hard on? But it looked like you were having such a good time!"

She then slipped a finger inside the waist of my jeans and hooked her finger around my new pink panties, pulling up the waistband outside my jeans. She looked at me again with her big beautiful eyes.

"Do you see this? This means you're my bitch. Get fucking used to it."

She let go of my panties and swiftly pushed me away from her with such force I stumbled backwards. She started walking.

"Come on bitch. Time to go to the hotel."

I followed, with the strangest combination of fear, nervousness, adrenaline, and arousal I'd ever had. And our second date hadn't even gotten started.