First Date with Richard

I scrolled through the website, scanning over the profiles as I did. Nothing really caught my eye. Some of these guys were attractive and plenty were younger than I expected, but none really were the one. None were love at first sight, until…

I clicked on the profile. Richard. Boy is he attractive. I read through his description, most of it talked about finding some companionship as that seemed to be what he was looking for out of this. Nervous as all hell as my heart pound in my chest, I sent him a message, simply calling him attractive and that his profile seemed interesting.

"Sent." I took a deep breath, crossing my fingers he would respond soon.

----

I paused my game as I heard my phone vibrate. I picked it up, my heart picking up speed at the fact the guy had responded to me. I smiled as I slid my phone open, opening up his message.

"Hey, Mae. Nice to meet you and thank you for the compliment. You're a very pretty girl. I'd love to chat."

I instantly replied, hoping he would be free to talk for a while. I have never talked to someone I've been so attracted to. "I don't really know where to start, I haven't really chatted on here before, outside of a few people almost instantly asking me out on dates."

"I can imagine. I'm sure a girl like you gets plenty of offers on a site like this." I smiled at his comment, closing my game so I could dedicate myself to this conversation.

"So, what do you…do for fun?" I brought out my, now, trademarked conversation starter.

I was surprised by his almost instant responses. "I enjoy boating. I have a few boats, including a yacht I share with a few other people. I also have my pilot's license. I golf sometimes, as well. What do you do, Mae?"

"I usually play games or sometimes do art. I'm a pretty creative person and have tried almost every type of art. Though I'm not great at any. But the flying and boating both sound really cool. My parents use to have a boat and sometimes I'd stay overnight on Chatfield."

"I have a boat I take down to Chatfield sometimes. I also have a few jet skis."

"I love jet skiing! You'll have to take me some time." I pressed send, before realizing what I had just said.

"I'd love to see you in a swimsuit." I instantly blushed at his comment, before receiving another message from him. "I hope I'm not too forward to ask, but I'd love to take you out to dinner at some point."

"I would happily go out on a date with you." I smiled to myself, excited he asked and already knowing it would be better than my last one.

----

"It's nice to meet you." I smiled at Richard as I took the seat across from him. He stood up slightly to extend his hand over the table to me. I couldn't help but admire the few rings on his hand.

"It's nice to meet you too, Mae." He shook my hand with a smile. "Is that short for something?" Richard sat back down in his chair. He looked all too handsome in his button up shirt, looking like the epitome of a dom.

"Nope." I smiled, my eyes scanning his face. Chiseled jaw, slight stubble, along with almond-shaped brown, nearly black eyes. "Just Mae. I was also born in May, so…" I shrugged laughing quietly.

"Original." He laughed. It was cute.

"Can you tell me more about your flying?" I asked after we made our order.

"I have a license as I said. I have a small plane. I would tell you what it is, but." He paused for a moment.

"I wouldn't know anyway." I shook my head, laughing quietly.

"Exactly." He nodded, a handsome smile showing his perfect white teeth. "I haven't flown in a while, but if you're not afraid of flying, I could take you some time."

"I'm terrified. If I was rich, I'd travel the world, but I'm also petrified of flying, so I guess money wouldn't help."

"Where would you want to go?"

"Japan mostly, but literally anywhere. I wanna see it all."

"I use to travel a lot for work, so I've been to many places. I would happily tell you about it sometime."

"I'd love that. Do you not travel much anymore?"

"Not since Covid, no." He shook his head. "And after I sold my company, I stopped traveling as much. That's the main reason I'm able to live so comfortably now."

"Where do you miss the most?" I tilted my head to the side slightly.

"China, my grandparents are from Dongzhou, as well as my mother. I use to travel there once every couple of years before they passed away."

"Ah. I'm sorry." I looked over at him sadly, but his Chinese grandparents made sense. He looked like he was likely biracial. I wonder what struggles his parents went through being together at the time.

"No need." He held his hand up. "We should move to happier topics. I apologize."

"No need." I shook my head.

"Well, if you ever decide you can handle it, I would happily bring you along on a trip. After all, there's nothing I love more than traveling with a beautiful woman by my side." If I can blush, which I can, I am. "What keeps you from traveling other than your fear? Not to say that isn't enough reason."

"Well money, obviously." I shrugged. "But I also have a disease that makes it harder."

"Which disease, if I may ask?"

"Meniere's. In short, a part of my inner ear tears and makes me dizzy." I shrugged. "But this can happen at any time, so I'm rather cautious about being out of the house. I have medicine that helps, but it can still happen."

"I'm sorry to hear that, Mae. You're strong to overcome it regardless."

"Thanks." I smiled. It always felt better when someone understood the level of strength it took to overcome daily, but it meant that much more coming from him. Plus someone pushing it off would be an instant dealbreaker, as it's such a large part of my day-to-day life. "I don't really drive because of it."

"Did you drive yourself here?"

"No." I shook my head. "My friend dropped me off."

"I'd be willing to drop you off back home once we're done. Unless you'd like to come back to my place. I have extra bedrooms."

"Oh." My eyes widened at his offer. Normally I would've never even considered going home with someone, much less on the first date, but something about him just felt right. Safe. "I'd like that." I smiled, making my mind up.

"I"m glad to hear it." He smiled back at me, as our waiter set our food down in front of us. We took a break from talking for a few moments to eat some of the said food.

"This is really good." I stated after swallowing down the food. "I definitely don't eat this nice back at home."

"What do you usually cook?" Richard asked, having no idea of my embarrassing answer.

"Pasta and TV dinners." I smiled shyly.

He laughed, shaking his head. "I use to have a private chef when I was busier, but as I found more time I made an effort to learn to cook. I would love to invite you over for dinner."

"You're really buttering me up." I pushed my hair behind my ear.

----

"Mae, I can take you home if you want." Richard looked over at me, a worried look on his face.

"No, no." I smiled at him slightly. "I'm actually just terrified of elevators." I motioned around us. "I'm excited to spend more time with you."

"I'm glad to hear that." The worry melted off his face, forming a smile. We made our way into his penthouse apartment. The place seemed to stretch over the whole top of the building, leaving him plenty of open space.

"I…" I looked over at Richard, chewing on my lip. "I just want to make it clear, before we get too far into our night that I don't plan on having sex."

"That's fine, Mae." He smiled at me softly. "I don't want you to pressure you."

"I…never have had sex before. So I want it to be special." I nervously explained myself, feeling like I had to.

"If you decide that I'm the person to do that with, I would be honored." My heart fluttered at his comment.

"Thank--thank you." I smiled up at him slightly.

"We can watch something if you'd like. Some TV." Richard offered, motioning over to the living room. I turned to face it, surprised to see the massive TV.

"Yes, please! I like cooking shows, if you do."

"I'll watch whatever." He motioned towards me to follow as he walked into the other room. We took a seat on the plush leather couch, somewhat near each other. Richard's hand sat on the couch near me, barely touching my thigh.

"You didn't drive, how do you plan to get home, if…you do?" Richard placed his arm on the couch behind me, looking over.

"I don't know an Uber probably." I rubbed my arm, looking down at my lap. I didn't want to invite myself over, but…I did want him to want me to stay.

"You're more than welcome to stay here. I have multiple rooms, as I said."

"I'd love that." I looked over at him with a small smile.

"You really are a beautiful girl, Mae." Richard reached over, his hand framing my face.

"Richard. I…don't know how to kiss." I admitted, hoping he was about to, but knowing damn well I didn't know the first thing about how to.

"I can show you." He leaned in, softly pressing his lips against mine. Our lips stayed pressed against each other for a moment before his lips parted, his tongue gently slipping into my mouth. As we continued to kiss, I reached over, placing my hand on his thigh. He parted, looking at me with some surprise, but more than anything: desire.

"Mae." He softly purred my name. I nodded at him, running my fingers up his thigh, stopping against his bulge. "Tell me you're sure."

"I am." I nodded again. "I am sure." I traced my fingers over his dick through his pants, able to feel as it grew.

Richard shifted on the couch, sitting up slightly to pull his pants down, leaving him pantless. He placed his hand on top of mine, before shifting once more to remove his underwear. I watched in curiosity, to be honest. I've only seen a handful of dicks in my life and most of them left me feeling like I didn't need to see another.

"Wow." I muttered, causing Richard to laugh.

"What are you saying wow about?" I looked up at him in surprise, realizing he heard me.

"Oh my god." My cheeks started burning up. "It--it just looks nice."

"You're too sweet of a girl, Mae." I loved the way he said my name.

"Can I?" I looked back down at his cock, holding my hand up, but hovering it off far enough to not touch it. Richard nodded, allowing me to place my hand on it. I was surprised by how warm it was, but even more so how soft it was. I lowered my head, licking the tip first, as if to taste it.

His fingers gently traced my face, running up my chin before running through my hair. He moaned my name out, running his fingers through and grabbing a handful. "You're amazing, Mae."

I put my mouth around his dick, putting it as deep in as I could, before moving back slightly and doing it again. I looked up at Richard to see if he was enjoying it. "Fuck, Mae." He shook his head, a small content smile on his face.

I popped his dick out of my mouth, licking down his shaft before moving his cupped balls out of my hands and into my mouth. I sucked, creating a vacuum in my mouth. "Oh fuck. Keep doing that." I looked up at him to see his head fully back and his eyes closed. I wanted to smile, but well…you know.

I continued the process, moving between giving attention to his head and the shaft, for a while longer until Richard spoke up again. "I'm gonna cum, Mae."

I moved my mouth off his dick, before looking up at him. "I wanna swallow it."

"Fuck, Mae." He ran his fingers through my hair again, before guiding my head back down. After a minute or so more, he finally cummed, leaving me with a mouthful of his warm cum. I swallowed it down, before opening my mouth to show him.

"Damn, Mae." Richard moved over to kiss me deeply, before pulling back. "You must have done that before. There's no way."

"Outside of practicing on bananas with my best friend…" I trailed off, realizing how dumb that sounded. "No. Never before."

"I'm a lucky man, Mae. You're perfect." His fingers traced their way down my cheek.

"Can…you show me the bedrooms?" I smiled slightly, wanting to move on from the topic.

"Sure thing, Mae. Just give me a second to recover." He leaned back on the couch, letting out a deep breath.