Carly's WMAF Fantasy Pt. 21

"I'm going to dress like a cheap, chink bitch and edge myself until I can't think anymore." Carly's smile was so broad you almost wouldn't believe the words coming from her mouth.

"Good girl," I said to Carly before giving her a little peck on her forehead and a pat on the ass. I grabbed Louise's hand and led her out, leaving Carly behind to do exactly as she promised. I had no doubt that we'd return home to find her a deliriously happy puddle of goo waiting for the final show.

--

Louise and I made out in the elevator... and the cab... and the waiting area at the restaurant. We got a lot of looks but neither one of us particularly cared. When we were finally seated, it was almost disappointing to have to keep ourselves at bay for the next half an hour.

As we waited for our appetizers, we made small talk, trying to pass the time.

"Okay... here's something I've got to know. How many people am I sleeping with?" she asked me all of a sudden. The question took me aback.

"Uhmm... none?"

"No... I mean... like they say that you're sleeping with all the people your SO is sleeping with... so if I jump into bed with you..."

"If?" I asked playfully, running my finger across her hand and eliciting a lovely giggle.

"Okay... when I sleep with you, stud... when," she said with some emphasis, "How many people?"

"Uhmm... Let's see... Carly and Sherry you already know about. Ditto Maureen that I haven't technically slept with..."

"Oh you will... she was fucking hot," Louise said with a smile.

"Probably," I said trying to play it cool, "But there's also Kyrsten and Rebeccah back in Orlando. And Alex and Natalie in Boston."

"Who are Alex and Natalie?"

"Carly's old roommates," I told her, "Kyrsten you met when she came to visit. The girl with the curly red hair," I said making vague gestures with my hand.

"Oh I remember. The girl with the sick curves. I was a little intimidated that day."

"Why?"

"Well, you were already fucking Sherry and Starla has big ol titties too... and then you trot in this redheaded booblicious sexpot. I mean... I started to wonder."

"I'm sorry," I told her, not realizing that she might have thought I had a 'type'.

"It was fine. I asked Sherry and she showed me a picture of Carly... that encouraged me a lot," she said with a laugh. Carly's not small chested by any means. A solid B Cup and slightly bigger than Louise. But I could see how it dissuaded her that I was some kind of tittie chaser. "Who's Rebeccah?"

"Uhmm.. well... the girl I went down to Orlando to try to hookup with, Jennifer?" I said and she nodded, remembering the story. "Her little sister was friends with Sherry in school and she and I hooked up."

"Damn stud... nailing all your high school friends' sisters, huh?"

"Just the two so far," I said with a smile.

"Okay, so that's what," she looked at her fingers that she'd been tracking with, "seven, right?"

I nodded, "Victoria and Daphne and work... oh... and Dave's wife Madison."

"Ten... Double digits in a couple months. Pretty impressive, Mr. S," she said as she cheekily bit her tongue between her teeth and smiled. "I had a one night fling with Jackie... Carly's college... uhmm... girlfriend sort of?"

"Girlfriend sort of... there's a story there but I'll get her to tell me, I guess," Louise said, letting me off the hook for that one. "Is that all?

"Uh.. well... I'm not THAT far removed from Sasha, my ex. But I got tested after that given how it ended and I'm not sleeping with her again. Oh... and I kind of slept with Mrs. Young," I said slightly sheepishly.

"No shit... really? Do they know?"

"Carly was there. She kind of encouraged it."

"Wow!" Louise said, lost for words for once.

"But Sherry doesn't know so don't tell her."

"I can keep a secret... okay... so that's twelve, right?"

"One more... but I don't think I can tell you about her."

"Wait... why not? Why all the secrecy now? You just told me you slept with your fiance's mother for crying out loud" She looked at me, watching my face for a reaction. I knew I was toast. I realized my mistake too late and she'd figure it out any second. There was no reason to keep anyone secret except...

"Starla? No way. When?"

"Shhh...," I said. It was kind of ridiculous but I was really uncomfortable talking so openly about it. I lowered my voice and Louise leaned in, "the week Kyrsten was here."

"Wait... really? So like your first date she put out? That doesn't sound like her."

"Starla is... well, she's special. She has some pretty particular kinks."

"Like what?"

"I'm not going to tell you that," I said.

"Does Kyrsten know?"

"Yeah, she kind of convinced me it was okay."

"Does Carly know?"

"Uhmm, yeah. I talked to her about it afterwards."

Louise looked at me and considered me silently. I thought I knew what she was thinking. If I'd told my other two girlfriends and wasn't telling her, what did that mean about how I felt about her. "You have to realize, Carly is the love of my life and I don't keep secrets from her. Ever. And Kyrsten was there when it happened and I've known her for forever. I trust her completely."

"No... I get it. I'm not worried about that, Jay," she said, surprising me.

"You're not?"

"No... I'm just trying to figure out what it is that she's into. I mean, I thought our histories were kind of tied up together but apparently... ooh, I know. She likes to be peed on?"

"What? Eww... no. Not that," I said and we both laughed, "And stop guessing because I'm going to stop answering."

"Fine, but one of you is going to tell me eventually," she said, stabbing a fork into her salad. "So somewhere between 12 and 14 girls depending on how you count. And like sixish steady, ongoing ones, right?"

"Yeah," I said, eating a breadstick.

"That's a lot of women to compete with Mr. S," she said. She licked her tongue around the small tomato on the end of her fork before popping it in her mouth seductively. The way her soft, pink lips wrapped around the red vegetable left my mind momentarily blank.

"Uhmm... I'm sure you don't have anything to worry about."

"Seriously? Don't you understand women at all?"

"What? Why?"

"All those girls have wayyyy more experience than me, right?"

I thought for a second, "Well... yeah."

"And I know that blowjob I gave you the other night wasn't the best you've ever had... don't lie to me," she said. She wasn't mad, just adamant.

"Look, Louise. Everyone worries about this their first time with someone. And it cuts both ways, right? I had to worry about how I compared to every guy they'd been with. But I know that sex with you is going to be absolutely amazing. Because you're sexy, open to try things and comfortable with your body. You're also obviously kinky as all fuck," I said winking at her. She blushed and ate some more of her salad before turning her gaze back to me. "Trust me... Do what turns you on and tell me what feels good and everything will be fine."

"What turns me on is the idea of riding you for hours while your fiance watches without cumming."

I felt my cock, already hard from all the teasing, get even harder. "I'm sure Carly would like that."

"As for what feels good... I guess we'll have to try everything so that I can tell you."

I smiled and leaned forward, giving her a kiss, "And that's why I know you're going to be dynamite in bed."

"Damn straight," she said. "OOhh... I know. I bet she likes for a girl to use a strap on on her?"

I laughed, "Stop guessing." Louise gently 'humphed' at my admonition but didn't bring it up again. The dinner continued, both of us ordering relatively light food because neither of us wanted to leave dinner feeling stuffed full.