Carly's WMAF Fantasy Pt. 19

Strangely, the day continued as most days did. I was able to catch up and actually get a bit ahead of my workload and by the end of the day, was feeling pretty good about myself. I picked up my phone and texted Carly.

Me: How's your empty yellow cunt, bitch?
Carly: So mean, Master😛 It needs you, Master. Is there pussy from your newest slut for me to clean off.
Me: You're pathetic, baby. But no. I had to clean it off. She was a virgin.
Carly: A virgin? Really? Wow... What did you think of that?"
Me: Honestly? It made me think about another certain virgin. I'm going to take your advice.
Carly: You're going to just ask her on a date?
Me: Yup. I'm going to take her out tonight 😈
Carly: TONIGHT?
Me: Is that a problem, slut?
Carly: 😍😓😣 No, Master.
Me: Good. Keep edging. If you're good, I'll fuck your ass tonight, bitch...
Carly: What if I'm bad, Master? It's getting so hard to edge without cumming.
Me: If you're bad I'll film you getting your clit whipped and send it to your mom and dad with instructions for him to do that to her.
Carly: FUCK... Master... she can't take that abuse... When did you get so deliciously cruel?
Me: When I found out it made you love me more.
Carly: 💗💖 It does, Master. I love you 😍😍😍
Me: Me too, baby.

Then I switched over and texted Louise.

Me: Can I take you out to dinner tonight?
Louise: Mr. S? Jay? Uhmm... yeah... I thought there were conditions?
Me: I changed me mind. They weren't reasonable of me and Carly helped me see that. So how about it? Just dinner... no strings or conditions.
Louise: Sounds... promising 😉
Me: Excellent! I'll see you in an hour and a half. Dress however you want, it's not the fanciest place in the world.
Louise: Oooh... thanks big spender!
Me: I didn't say it was cheap ;)

With that settled, I buzzed in Victoria. She sauntered in, eyes practically fucking me the moment the door swung shut behind her. "Yes, Mr. S. What can I do for you?" Her voice was husky with need.

"You know I have an unconventional lifestyle, right?"

"You've made that clear, Sir."

"Do you have plans tonight?"

"No, Sir," she said with a smile. "Are you taking me somewhere?"

I shook my head, "Not tonight. I have a date tonight," I said. A frown flicked ever so slightly at the corners of her lips before she returned them to their neutral position. "But I have something you can help me with."

"What is it, boss?"

"Go shopping right after work but then take everything to my place. Here's the address," I said handing her a card with my home address written on the back. "Carly is there and she may need... help... with her little project for the evening. I think it would be good if you got to know her better and you could show her what you bought and make sure I'm okay with it. Tell her what I told you today first. Otherwise she'll probably accuse you of being too prudish for me," I said and flashed a quick smile.

She flushed at the thought of playing dress up for my fiance. Little did she know what my fiance would be doing the entire time. Nevertheless, she nodded and I dismissed her.

I headed out of the office quickly, grabbing a car and racing across town, eager for my date with Louise. I was weirdly giddy and nervous, feeling almost like a high school kid going on a first date with a girl he had a crush on. It took a conversation with Carly but I was realizing that my feelings for Louise had definitely gotten into "irrational crush" land. It was time to see if there was something there beyond just the flirty undertones.

She was sitting in the lobby waiting for me. I could tell instantly she was nervous too. She tucked her sandy brown hair behind her ear as her foot tapped rapidly on the floor. As I walked up, she stood quickly, practically jumping up before she skipped over to me and planted a light peck on my cheek. She was wearing a tight t-shirt with some k-pop band emblazoned across the front. Between the short t-shirt and low rise jeans she was wearing, her tiny waist was well highlighted. She wasn't wearing much makeup but she didn't need it at all. All-in-all she projected this clean cut, almost girl next door look.

An image she immediately shattered when she whispered, "I'm so wet right now. I'm not wearing panties, Mr. S."

I looked at her as we walked out, confused, "Why tell me? I told you there were no strings tonight."

She smiled flirtatiously, "I just thought you'd like to know."

I smirked back, "Well definitely. Keep doing that and I'll definitely be... interested... all night." She smiled back and gave me another gentle kiss on the cheek.

We rode in slightly nervous silence for a couple minutes before making some intermittent small talk. I wish I could tell you I was suave and sophisticated but truthfully, I realized I knew very little about her. I did remember her major, however.

"Linguistics and Computer Science, right?"

Louise turned to me with a genuine smile that lit up her face. I'd seen her smirk and make beguiling, seductive smiles before but now it occurred to me that I'd never seen a truly honest, happy smile across her face. "You remembered!" she said, genuinely surprised.

"Of course. Sherry told me how smart you were and you picked a pretty hard double major. Who would forget something like that?" I said, confused.

"You'd be surprised. You flash a pretty smile and a little flesh and guys frequently don't remember much," she said.

"Maybe that just means they're guys not worth dating."

"Oh? Does that mean you ARE a guy worth dating?"

I smiled back, enjoying the less sexual, more honest banter. "I'd like to think so. Seems lots of girls think so too."

"About that... I mean... it's kind of weird, right?"

"Oh definitely. If you'd known me six months ago, you'd REALLY be surprised."

"Why's that?" she asked. We pulled up to our destination, a small, nondescript door on West 46th. One of the ever present scaffoldings framed the door, surely warding off paying customers. I pulled the plastic tarp to the side and ushered my lovely date inside. The old, metal red door creaked but whatever you might have imagined inside you'd have been very surprised. The host greeted me warmly, "Mr. S? Good to see you again! And who is this lovely lady you've brought with you?"

"Enriquo this is Louise. And keep your hands to yourself, she's MY date this evening," I said as I slipped him a couple twenties. There wasn't that much competition for seating right now but I'd found that this was, by far, the best date experience to give a girl and it was a small price to pay.

"I wouldn't dream of it, my man," he said warmly before leaning closer, "What happened with Ms. Sasha?"

I frowned, "We broke up. It was ugly," I whispered back and he showed some genuine sympathy. I'd discovered this place through Enriquo's brother, a co-worker of mine. Most of the guy's family actually worked here. The guy I actually worked with was a dick but Enriquo and the rest of the family were pretty cool and it felt good to throw their family some business like this. In return, they treated me like family.

Louise smiled at me in amusement, "So this must be where you take girls to impress them?" she said.

Enriquo heard and countered back, "Mr. Jay has only brought four girls here and only Ms. Sasha for the last year. Mr. Jay is definitely a loyal man. He's the furthest thing from a player Ms. Louise."

Louise squeezed my hand and gave me a smile and eye roll. After Enriquo left we both exploded in laughter. "I guess you weren't kidding that I'd be surprised by the you from six months ago. Want to tell me about it?"

"You're asking me to tell you about my ex? Isn't that a first date no-no?"

"My rule is to not talk about your last significant other. By my count, Sasha is like five girls ago." I must have looked guilty, "How far off am I?"

"Uhmm... as of this afternoon?" I made a show of counting with my fingers then hit ten and thoguht for a second, "Eleven... I think?"

She laughed again, the genuine honest one, this time laughing so hard we got a couple of looks from the sparse clientele and a couple tears rolled down her eyes. "Eleven?"

"What's so funny?" I asked, knowing the answer.

"Nono... it's not what you think. I was just picturing poor Enriquo's face if we told him you'd been with 11 girls since you broke up with Sasha," she said.

I couldn't help it, I laughed too. It was a great tension breaking moment and, as I look back on that night, I always remember that as the moment that she and I started actually bonding.

"So... seriously... what happened with her?" she asked. Her hand reached out and grazed mine gently and she let our pinkies entwine slightly.

"I don't know. I really don't. I thought things were great. We were talking about getting married. Everything was fine and then she took a new job. I'm pretty sure she met someone there but I never found out. All I know is that she was one day telling me how wonderful I was and the next, everything I'd ever done was wrong."

"Maybe you changed. Did things at work change?"

"No... I mean maybe... but it was things she used to love that she suddenly hated."

Louise's brow furrowed, "What do you mean?"

I thought about it, trying to come up with a good example, "Okay... so she was at my house every night and we both worked long hours. So neither of us would ever want to cook anything. So I'd get take out and bring it home. She was a super picky eater and pretty much only ever got one thing from each place so I knew what she wanted. And she loved that. She told me she did. She told me how she loved how well I knew her and that I took care of her and that she didn't have to worry about thinking about food but could just come over and veg out and know that there would be hot food waiting."

"Okay..." Louise said quietly, simply listening.

"And then one night I brought home food just like normal. I set it all out and camped out on the couch. She came in and took one look at it and started screaming at me. Telling me how I took her for granted and never asked her what she wanted and what if she wanted something different. It went on like that for 15 minutes before I even said anything because I was so confused."

"Weird," Louise said, still watching me. It was hard reliving some of these things but also really nice. I hadn't even talked about this with Carly very much. But as the words flowed out of me, I realized how much I'd needed to talk about it.

"There were other things too... you know... intimate things. She just changed. It was like less than a week and I was dating a different woman."

"What kinds of... you know... intimate things?" Louise asked with a curious grin.

I looked at her but figured if I wanted to be with her, she'd find out eventually.

"Well... I mean... I'm pretty... uh... dominant... in the bedroom," I said.

"Oh yeah? I never would have guessed," she said sarcastically.

"Well Sasha was kind of into it but really not very adventurous. She loved sex but it was lights off missionary every time. We talked dirty but that was about it. I tried to get her to do other things but she was adamant that she didn't want to. I respected that. She would get really turned on and really into it when I was... uhmmm... more aggressive... but if I tried to move her into a different position she would totally lose the moment."

"That's... odd," Louise said, squirming in her seat a little.

"Is this turning you on, Louise?"

"Maybe," she said coyly.

"Well don't get too turned on or you'll wish you hadn't gone commando."

Her eyes went slightly wide as if she'd forgotten before she squinted at me and stuck out her tongue playfully. "Finish your story, Mr. S."

"Well about a week after the fight over chinese food she flipped out on me. Started yelling at me for never doing anything different. I tried explaining but she just yelled at me more. We broke up about two weeks later."

"Wow... that's... kind of fucked up."

"Yeah," I said. The waiter came and took our order, giving us a much needed conversational break while we reset ourselves. I hadn't planned on getting this deep with Louise so early but she seemed genuinely interested and curious and I felt very much at ease talking to her. "What about you. You must have your own story," I said. I knew the broad outlines but not the details.

"Starla told me she told you," she said quietly, looking me dead in the eyes.

I paused, not sure what to say. I'd made Starla tell me in the throes of passion. I didn't really feel guilty about that. I had no idea it was so personal at the time. I looked at Louise who didn't seem to have any judgement in her eyes.

"Only the broad outlines... and some of the personal ones," I said. Louise nodded and smiled.

"I appreciate you being honest. I hate liars."

"Me too," I said, thinking back to Sasha. I wondered if I'd ever know if she was cheating on me. "So give me your version. Tell it in your words," I said shifting the focus back to Louise.

"My Dad had a woman problem. Or maybe a commitment problem. I don't know. It was an endless parade of girls at my house. My Dad. My brothers. All of them. They all treated me like their precious little princess and protected me. But none of them cared about my school or sports. Except cheerleading. They loved watching me on the cheerleading team."

"Your Dad?" I asked, more than a little alarmed at the inference.

"No. It wasn't like that with Dad. He didn't care about me much at all. But my brothers, yeah. They were only a couple years older than me and dated all the girls on the squad before they graduated and moved on to college girls."

"I see. And why is that?"

"Because the girls threw themselves at them. My Dad had money and girls like that. They had tits and guys like that."

I frowned but she continued, "And then?"

"I didn't know it at the time, but my brothers started fucking Starla the day she turned 18. They had a whole series of bets about who could get her to do what and when," she said with a sadness in her voice.

I hadn't heard this part from Starla, probably because it was a little too painful, "Don't tell me if you're not able. Or if you think Starla would be angry."

She shook her head, "Starla's fine with it. She told me when she was telling me she told you about what happened. She really likes you, you know?" I nodded, "She has a hard time opening up to people and letting them in but she really likes you... Anyways, I should have known something was up when Starla bleached her hair bottle blonde and started sunning everyday at our house. But I didn't make the connection. She'd sit there and twirl her hair, blow gum and generally act like some sort of idiot Barbie doll and I didn't even realize..."

I gripped her hand in mine and willed her to continue, "She uhmm... well... they bought her some alcohol to share with me on my eighteenth. We got... uhmm... intimate out at the pool. It was the first time anyone had ever touched me and she was really, really good. And it was absolutely amazing. I came so hard I nearly blacked out and when I opened my eyes, my Dad was standing there screaming at Starla and me. He kept calling her a fuckinig dyke and made her run out of the house half dressed. My brothers were sitting there laughing. They'd watched the whole thing because of course they had. And you know who got in trouble? Me? My Dad grounded me for the rest of my senior year. I missed prom. I missed graduation. He shipped me off to summer school up here at the first opportunity because he finally realized I wasn't his perfect little princess."

"Holy fuck... Louise... that's...," I really had no words. She had a single tear coming down her face that she wiped away as she looked at me. She'd made peace with her fucked up family and it wasn't on me to tell her how screwed up it was. "Let's talk about something else. Tell me about your classes," I told her, knowing that the subject needed to be lightened.

We continued the dinner and very much enjoyed each other's company. She and I had a very similar world view. We both thought the President was an idiot, that both parties were idiots and the most of the voting population was idiots. We also agreed that we were both elitist pricks when we realized that we shared the opinion that the rest of the world was filled with idiots.

She was really excited about her prototype natural language software. Her early summer start had gotten her in touch with two prominent visiting professors and they were getting ready to publish a paper applying a unique new machine learning algorithm to speech recognition. She explained some of it, I understand enough to know that I didn't understand it and we laughed.

At the end of the dinner, I escorted her out of the restaurant and we started walking down the street, "I'd love it if this date didn't end right now..." I told her, fishing for I'm not even sure what.

"We could go back to your place," she said softly. I looked into her eyes, trying to read them. But I also heard Carly's voice and knew, especially after talking to Louise, that Carly was right. Jumping into bed with her was absolutely possible. And would absolutely destroy her. "You don't have to do that, Louise."

"Do what, Mr. S?" she said.

"I get a LOT of sex from all the others. But that's not all I'm interested in."

She blinked at me, silent for the first time. I smiled back as she studied me before she eventually replied, "You didn't know anything about me before tonight. If it's not my flirtiness, what made you want to date me?"

Honesty is the best policy, right? "Don't get me wrong. The flirty... almost slutty act definitely got my attention. I obviously have a type," I said. Louise laughed gently. It was a soft, melodic sound that I was already starting to love. I continued, "But then you became this interesting puzzle to obsess over. I wanted to know what makes you tick. Why act like a slutty virgin?"

She shifted away from me and looked into the windows of the stores as we walked vaguely towards Times Square, "I don't really know," she said.

"Can I make a guess?" She just nodded, not even turning so I continued. "The guys in your family are womanizers, right? They probably have a type too, I bet. Brainless, slutty girls, right?'

She turned back to me, looking at me and nodded softly.

"And you know that's not you, right?"

She nodded again, "They like big titted, dumb blondes. And I'm none of those things."

"Your brothers are idiots, Louise. Your Dad too... no offense."

She nodded, "I know."

"Carly thinks you would sleep with me tonight if I asked. Is she right?"

Louise said nothing for a moment before nodding silently.

"I want to take you back to my place and fuck you until you can't walk. But I'm not going to. You know why?"

"Why?" she asked.

"Because I like you more than that. I think if you got that from me... I think it would affect you badly."

She nodded again, "I think you're right."

"Did you think you were going to fuck me tonight?"

"Yes... I knew I would if you asked and I was pretty sure you'd ask."

"Are you surprised I'm not?"

"It's a level of self-control I hadn't expected," she said impishly.

"Hey... maybe it's not self-control. Maybe I just don't find you attractive," I said in mock defense.

She laughed again and sort of skipped away, looking me up and down before coming back and bouncing into my arms. She looked up at me as people streamed around our now stationary island on the sidewalk, "Your cock has been rock hard all night, Mr. S." The way she whispered it to me caused my cock to twitch and stiffen further, "Either you find me attractive or you've been day dreaming of your other eleven women instead of focusing on your hot little coed date."