“And you’ve already been an idiot for just long enough to start this thing, so forgive me for keeping an eye out and trying to keep you from being an idiot long enough to end this,” Sarah remarked dryly. “I rather enjoy the harem life, and would be quite miffed if it ended suddenly.”
She rolled her eyes. “Dating is the absolute worst.”
Somehow, I felt better. I’d aired out my secret, and been told that, while yes, it had been dumb (like I hadn’t figured that out forever ago); it had also kinda worked out in my favor. I went back to my room and called it a night.
The next morning, I knew what I wanted to do. I checked my closet and found, to my surprise, it was already stocked with several formal suits, in my size (I checked). I reflexively checked my bank account to see what was in my budget, before remembering that I was being paid thousands of dollars each week for my continued support of Courtney’s education. At this point, I was almost unneeded as a tutor, but occasionally Courtney and I would come across one of the subjects we had skipped over in catching her up and we’d have to do a deep dive, but in general, Courtney was doing fine and it was more of an allowance than a salary.
I whipped out my phone and was busy looking for a nice place to go when the door opened and Berkley strutted in.
“Good morning, Tom.” She greeted me. “What are you up to?”
“I want to take Courtney out somewhere nice… I mean, we aren’t that far from like… New York City… But… I’ve never…” I floundered.
“Ah, let’s see…” She came over and looked at my phone before frowning. “Do you have any budgetary concerns?”
“No, I mean, I have several thousand dollars in the bank and haven’t had to spend any of it, so… yeah,” I admitted.
“And you want to take her someplace nice… upscale?” Berkley verified.
“That is what I was googling,” I confirmed.
“You are aware that most places like this are solely by reservation and book out a month, if not more in advance?” Berkley verified.
“Damn it,” I grumbled.
Berkley chuckled. “I haven’t had to do this before… but let me reach out to Clarence… he always has his ways.”
“What do you mean?” I protested. “If they’re booked out…”
“You, my good sir, are now one of the privileged elite… a VIP. Talk to the right people… and I’ll let you know what happens,” Berkley informed me. “But many of these places require formal wear. I know we stocked you, but I’ll try to make sure arrangements are made before lunch. Courtney might want a new dress for such an occasion.”
Berkley pulled out her phone as she walked out and heard her say, “Hello, Clarence? I need your help with something…”
I felt a little better and wandered down to the dining room to eat breakfast.
Walking in, I looked at the assembled girls. I’d want to take Abby on a nice date too, a dinner or something. She liked going out in public and having ‘the dating experience.’ Most of the other girls probably thought of this entire trip as a bit of a date. Courtney was chatting over her eggs and toast with Cindy. She was still the queen of my harem and the one who would get the title of wife. She deserved to be spoiled on occasion.
I sat down next to Courtney and Lizzy piped up, “What can I make you for breakfast?”
“I’ll probably just go with granola and yogurt,” I explained.
“I’ll get that for you, just one second,” Lizzy assured me happily, hopping up to go get it. She was looking great. She had always been cute, but working with Tina was helping her be more confident in herself and that confidence was sexy.
I was feeling good, so everything seemed to be going even better. All the girls of my harem seemed happy and excited at the opportunities presented.
“I can’t believe you have beachfront property, with a private section of beach, and still have an indoor pool!” Cindy was marveling.
“Well, Daddy loves to swim, so we almost always have a pool or something available. And he doesn’t like it when the weather ruins it when he wants to go swimming, so the beach is there if the weather is nice and the pool is there if it isn’t.” Courtney explained.
“Would the beach be clear for a beachside fuck?” Debbie asked excitedly. Debbie was getting excited about her weight loss journey with Tina. She had set an initial goal, and she was getting close to reaching it. This led the exhibitionist girl to be even more confident in the flaunting of her body. Unsurprisingly, she was leaning back against the back of her chair, naked, her food finished.
“That’s probably not the best idea…” Khloe admitted. “I’m not sure about the indecent exposure laws here, but even if the beach is technically private, it is really hard to enforce that… and I don’t know about you, but I don’t want a group of trespassing men to see me, or worse.”
Debbie sighed, “Dammit. Why can’t people just let me be?”
“Maybe because small children don’t need that?” Mary suggested.
“Indeed, exposure to sexual topics before children are properly developed is not good for them,” Sarah admitted. “But sexual education in America needs serious help.”
I chuckled. Debbie might be the most flagrant exhibitionist of the group, but I knew a good portion of them enjoyed flaunting their bodies. I was so entertained by the discussion that I didn’t notice Berkley sneak in until she put a hand on my shoulder.
“You have reservations at the Restaurant Daniel this evening at 5:15,” Berkley informed me. “Under the name, Carmichael.”
“Ooo… Daniel?” Courtney smiled.
“So much for keeping it a surprise.” I chuckled.
“My apologies,” Berkley stated, with no remorse.
I smirked at her. “I was figuring I could take you out for a pleasant night.”
Courtney grinned. “And I get to put you in a suit… WHAT WILL I WEAR?!”
“Girl’s night!” Cindy called, and the others joined in the plotting. Amy came in to do some cleaning, wearing the skimpy maid outfit, and immediately got pulled into a discussion about what options there were at the estate.
I was glad I ate fast because Courtney grabbed my hand and pulled me out into the hall and toward her room. “You have to help me pick out what to wear, then it will be my turn to dress you up!”
I chuckled at the joy she was taking at this. “Of course.”
She pulled me into her room, pushed me to a seat on her bed, and promptly was wearing nothing but a sexy strapless bra and her matching thong. She began throwing on formal dress after formal dress. A green sequined gown that clung to her and showed off her curves? No, it wasn’t the right weather for green. A pink A-line with a keyhole cutout for her cleavage? No, too childish for today. Each dress she threw on made my dick ache, but she’d just accept the praise of how gorgeous she was, then turn, look at the mirror, find some reason to toss it on the bed then scamper back into her closet to find another.
“No use.” She admitted. “I have nothing to wear. We’ll have to get something new.”
I laughed. “You had already decided that, hadn’t you?” I pressed.
“Maybe…” she teased. “But you can’t pretend you didn’t like the show.”
She teased, a finger tracing my erect penis as it pressed against my pants. “Gotta do something about this.” She laughed. “Can’t have you walking around respectable establishments with a boner bouncing around.”
She pushed me back on her bed, my shorts and boxers pulled off in an instant, and her lips wrapped around my dick.
“Oh, fuck.” I moaned as she began expertly swallowing my length. She stared into my eyes as I deeply probed her throat and her tongue snuck out to swirl around the base of my dick and tease my sack. “Damn, you are good at that.”
She grinned and popped off. “Good. If I wasn’t, with as much practice as you let me get, it would be a shame.”
She straddled me, pulling her thong to the side, and slid her pussy around my dick. The lube of her saliva and her arousal made it a smooth entry until her clit was rubbing against my crotch. She latched onto me, kissing and intertwining our tongues as she bounced up and down. Fuck, she was great. I couldn’t think of anything but how amazing her pussy felt as it surged around me. I could never resist and started groping her breasts through her bra. She tore it down in frustration and pulled my hands to her now bare breasts.
I let her go, slamming herself down and fucking herself hard until I was about to blow. I grabbed her hips, just as her legs started to quiver and buckle from an orgasm. I started thrusting and bouncing her on my rod, until I pulled her down, driving hard into her and filling her with my cum.
“Fuuuuuuuck.” She groaned. “Goddamn…. I love feeling your cum rush into me like that.”
She rolled off me and kissed me once more. “Oh, darn. My panties are all dirty now, gotta pick new ones.”
I caught my breath and pulled my boxers and shorts back on as she flung her underwear into the hamper before going to the bathroom to clean up. I followed and watched as she sat and let the cum leak out of her and drop into the toilet.
“Enjoying the show?” She asked teasingly, rolling her shoulders back to press her boobs forward.
“Always,” I assured her.
She finished up, pulled on a lacy pink thong and matching bra, then put back on the clothes she’d worn to breakfast and marched me to my room. I don’t know what difference she saw between the thirty white, button-up shirts, or the fifteen suits hanging in my closet, but she picked them out and found a nice dark blue tie. Once I put them on she just gave a groan of satisfaction.
“Fuck, you look good in a suit that fits you.” She smiled. “We’ll have to get it properly tailored, but it still looks terrific.”