I slipped on my summer dress, for the first time in a month. Every time I looked at the dress, I remembered the last time I'd put it on, after exposing and humiliating myself for the enjoyment of a bunch of college boys. I hadn't been able to put it on since, but I hadn't been able to get rid of the dress either. Did I enjoy the memory, or did I hate it? I still wasn't sure.
Today, though, I wouldn't be able to escape the memory. I had agreed to go out to dinner with Connor, who had held my leash while I crawled around and squealed like a hog with a little piggy tail sticking out of my ass. And we were going to Margo's restaurant, the scene of my degradation.
Feeling a little bold and a little silly, I decided to go without a bra and panties, just as I'd gone before. I told myself it was a new tradition with this dress, and certainly not because I hoped that Connor would grope me.
This time I drove my own car to Margo's. The car I'd paid for with my pride. I pulled into the parking lot and found Connor waiting for me at the restaurant door.
"Hey," I said.
"Hi pearl!" Connor said with a huge grin.
I was struck again by how adorable he was. It had been a bit of struggle to focus on work the past week after agreeing to a date with Connor, but we'd managed to not do anything inappropriate at the office. Tonight, there was a week of anticipation built up between us. I hoped we wouldn't explode.
Connor took my hand and we headed inside.
"Darling!" Giorgio abandoned the guests he was helping when he saw Connor and I enter, hustling over to us.
"I'm so glad you gave this fine young man a chance, Pearl. But why did it take him to get you back here? You left so quickly last time, and I never even got to say a proper goodbye." Giorgio pouted.
My face burned red, suddenly feeling like maybe I should have come back sooner. "I'm sorry, Giorgio. I've been, busy."
Giorgio ignored my lame excuse and looked me and Connor up and down, "Did you two plan your outfits?" He teased.
"What?" I asked, confused.
Giorgio rolled his eyes, "please darling, I know
you
know what dress you put on today, but did you even look at your date?"
I looked at Connor, then met his eyes. He still looked confused, but I got it. Connor was wearing a Hawaiian shirt and khakis. Pants, not shorts, suitable for dinner. But that was definitely the same shirt.
"You wore that shirt the night we met," I said, "and I was wearing this dress - before we met."
"Oh," Connor looked like he was struck by the memory of me when he'd first saw me, naked and crawling.
"Well, now that you both are in the right frame of mind, follow me!"
The guests who'd been waiting ahead of us gave us looks of curiosity and irritation as we skipped the line. Connor had said that he got this treatment every time he came here, I remembered.
Giorgio led us to a round booth in the back corner of an upper balcony. It was the most secluded spot in the restaurant. Connor must have told Giorgio we were coming, if this this booth had been saved for us.
I scooched into the booth and Connor sat opposite me.
Giorgio tsked at us. "Unless you two close the gap and sit next to each other, I'm going to make you sit somewhere else and give this booth to a couple who knows how to use it properly."
Connor and I looked at Giorgio, then each other. Sheepishly, we scooted around until we were next to each other in the back of the booth.
"I can't believe we let him order us around," I said quietly after Giorgio left.
"It's hard to say 'no' to him when he's telling me to do something I want to do anyway." Connor replied.
"True," I laughed.
Hesitantly, I set a hand on Connor's thigh. Connor put his arm around my shoulders, and I moved even closer to him, our thighs touching. Connor was tall enough that his hand could easily reach down and grab my boob from where he'd laid it on my shoulder. I shuddered, imagining it.
I wanted to run my hand up his thigh and feel whether he was hard or not, but I worried that would be too forward. Connor leaned his head down to mine until I could feel his breath on my ear. My nipples tightened.
"Your hair smells good." He said as he inhaled.
I turned my face towards him, our lips nearly touched. I looked into his eyes, hazel green with flecks of brown, bordered by pale blond lashes.
"Good evening," the waiter interrupted our moment.
I blushed and looked at the table briefly before looking up. Connor's hand squeezed my shoulder lightly. I picked up the menu and chose something randomly. Food was not on my mind right at that moment. I wanted something else in my mouth. I wanted Connor.
"Pearl?"
"Hmm?"
"I want to kiss you." Connor said softly.
I looked up at him again. His eyes were focused on mine, then his gaze drifted lower, to my mouth, and then lower. I lifted my chest a little, knowing he was eyeing my cleavage. Could he tell that I wasn't wearing a bra?
"Kiss me, then." I told him.
Connor raised his hand up from my shoulder and wrapped it around the back of my head. He pulled me towards him and bent his head to mine. I closed my eyes as his lips touched mine lightly. Our breath mingled between our lips.
I pressed closer and licked the gap between his lips. His tongue met mine and I pressed my cleavage into him. He brought his other arm around to enfold me, wrapping it around my back. My hand on his thigh inched higher.
If we didn't stop this, we would end up fucking right here, in this booth. And what if we did? Part of me wondered. No one would see, except the waiter. And would he care? Wasn't that why Giorgio had put us in this booth?
I drew my hand up over Connor's groin, noting with pleasure that he was hard, and then I kept moving my hand up, under his shirt. Connor's abs were firm and his skin soft and warm under my touch. Wetness pulsed from my pussy.
Connor groaned and moved his mouth across my cheek to my ear, and then down my neck. Slowly, so slowly, he kissed his way down to my shoulder, then my chest, until he was kissing the top of my breast where it met the line of my dress.
I dug my nails into Connor's stomach as I angled my chest towards him. I wanted him to take the next step, to pull down that bit of fabric and take my nipple in his mouth. I couldn't believe how aroused I was.
Abruptly, Connor pulled back and looked towards the front of the booth. I looked up as the waiter placed wine glasses in front of us.
"Margo sends this bottle of Cabernet Sauvignon with her best wishes for a happy reunion." The waiter said, ignoring our risqué behavior.
"Please tell Margo thank you," Connor said, with perfect politeness.
Which of us was older, and the boss? Yeah, that was me, the one trying to get fucked in the middle of a restaurant. The one who recently got naked in this same restaurant. Right, I told myself. Be an adult.
The waiter opened the bottle and poured wine into a glass decanter on the table, leaving us. I looked at Connor and grinned.
"Well, should we have some wine?"
"Nah, you got to let it air, then he'll be back to pour it." Connor told me.
"Oh, is that a fancy rich person way of drinking?" I asked, laughing.
"Yeah, I guess." Connor actually blushed a little.
"Well, what could we do while we wait, then, hmm?" I hadn't taken my hand out from under Connor's shirt, and I stroked his stomach a little now.
"I don't know," Connor mused, "maybe we should talk?" He leaned his head down to my ear and whispered, "I want to make love to you."
I shivered. It was so cute the way he treated me like he couldn't be vulgar with me and just say he wanted to fuck. He treated me like I was a lady, even though I'd been very unladylike when we met.
I took a deep breath and prepared to act like the mature adult in this relationship.
"Before we have sex, are you clean? I mean, have you been tested for STDs recently? I was tested last month and I'm good." I told him.
Connor frowned, "no I haven't been tested lately, but I'm good."
"How can you be sure?" I asked, then an unwelcome thought struck me. He
was
young. "Are you a virgin?"
"No," Connor shook his head, his face reddening. "But it's been a long time and I got tested after the last time."
"Mmm, why so long?" I asked, curiosity displacing my arousal.
Connor blew out a breath and leaned back in the booth, "My last time was prom night, then my girlfriend broke up with me and I haven't been interested in dating this year."
My skin prickled, "Connor... Are you telling me that you're a freshman?"
Connor looked at my curiously, "yeah, I guess you didn't know that. But does it matter?" He glanced at the wine, "I have a fake ID for alcohol, everyone in the frat has one."
"How old are you?" At the end of freshman year, he had to be at least 18, right?
"19." Connor said.
I let out a tense sigh. Thank goodness he was at least legal for sex. But 19, that was so young! I was like half his age older than him. I felt like a cradle robber.
I pulled my arm out from under his shirt and put my elbows on the table, then plopped my head into my hands glumly.
Connor rubbed my back, "hey, what's wrong, Pearl?"
"You're a baby," I whined, "and I'm a cougar."
Connor laughed, "You're way too young to be a cougar. And besides, age gaps are totally fine. My dad, for example, is thirty years older than my step-mom."
"Wow, really?" I asked.
"Yeah, so you're like four years older than me, not a big deal." Connor said.
"But I'm eight years older than you." I told him. "Do you think your dad would hire someone that young to lead acquisitions?"
"I don't know, he likes hiring young people, thinks they have energy to get things done. He thinks old people are too arrogant and lazy. Except him, of course."
"Oh." I had known I was young for the job, but I thought that my work at the charity had been pretty impressive. It hadn't occurred to me that being young had helped rather than hurt.
"And he said Livvy recommended you, so that pretty much clinched it." Connor continued.
