Too Good To Be True Ch. 29

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Tom and Courtney take advantage of their new location.
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Part 29 of the 29 part series

Updated 02/11/2024
Created 05/22/2023
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Dear Readers,

Thank you for your patience, life has been crazy and my new editor had to catch up on this story before he could edit it. I also took into account some of the feedback I've been getting and I hope the rewrites I am doing show that I do, in fact, listen to valid criticisms. This story still has a long way to go, unless I am very mistaken, so while it will take a while to get there, I hope you continue to enjoy the ride.

Thanks again to my fabulous editors, Bry1977 and thegoofyproofyreader. They are doing great work helping me catch a lot of mistakes and improve a lot, so I can't thank them enough.

Without further ado, the next chapter awaits...

~NaughtyPaladin

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Chapter 29

After Berkley left, I lay there for a good half-hour. I had a lot to think about. My harem had grown quite a lot and while it was undoubtedly hot to be in such demand, it was also... weird. Definitely weird. I'd been a bit of a nerd all my life, so the girls hadn't exactly been lining up to date me, and now there were absolutely babes just volunteering to be my fucktoys. I ended up dressing and went to look for Sarah.

Amy helped direct me to Sarah's room, and I found her inside unpacking.

She took one look at me and set aside her work. "Need to talk?"

I just nodded and closed the door.

She sat on her bed and motioned to the recliner.

I chuckled. "Don't have your therapist's couch, so they gave you a recliner?"

"It's easier." She shrugged. "Now, what did you want to talk about?"

I took advantage of the reclining feature and leaned back, staring at the ceiling. "Why do you guys even want to be with me?"

"There are a lot of reasons," Sarah assured me. "Do you remember why the first few of us joined and formed the harem?"

"You were horny, and I had a dick that wasn't getting stuck in every pussy on campus... But now I'm basically doing that, aren't I?" I demanded.

"And you believe that if we didn't find you to be appealing in more ways than just being a convenient penis, we'd have still gone ahead with it?" Sarah pointed out in that 'you know I'm right' sort of way.

"But WHY?" I demanded, throwing my hands up in frustration. "Until I was with Courtney, I had absolutely NOTHING going on... romantically. Now, I'm being treated like some sort of sex god. With everyone just throwing themselves at me."

Sarah thought about that for a minute. "I know I found you attractive when we first met with you... but this may be the phenomenon of the female attraction to a taken man. Studies suggest that in fish and birds, a male that has a mate is viewed as more appealing, and in some ways, the other females view the mating male as being pre-validated as a suitable mate. I can't say that it wasn't the case with me, because even then, I knew that you and Courtney were a pair."

She crossed her legs and put her elbows on her knees, her chin leaned forward on her hands. She clearly didn't care that I could see her panties up her skirt, which made sense considering the number of times I'd taken her panties off.

"Then... it is entirely possible that the validation of you having multiple women willing to share you further validated your desirability as a partner, opening the door for future harem members to see the appeal." She concluded. "But that's just a theory."

"So... classic case of 'if your friends jumped off a cliff, would you'?" I asked.

"A similar concept, but with a sexual partner, yes," Sarah admitted.

"So if Courtney chose poorly, and I was... some pervert who would coerce a woman into sex, the rest of you would have just gotten pulled into the shitstorm?" I declared, remembering how my relationship with Courtney had REALLY started.

"Absolutely not." Sarah laughed. "You think we would have stuck around this long if you were someone like that?"

"I don't think you know me at all," I confessed.

"If you are referring to the blackmail, you should know that Courtney told me all the details ages ago," Sarah informed me.

My head shot up.

"No, I haven't told the others," Sarah assured me. "Doctor-patient privilege, you know?"

"So, you know I'm a scumbag." I declared, covering my face, "So, why are you still here?"

"Well, while I certainly disapprove of that part of how you two came together, was that ACTUALLY why you are together now?" Sarah pressed. "As I understand it, you gave Courtney a full two weeks to pick out the man to whom she would lose her virginity, and she chose you at the first opportunity. Why do you think that is?"

"She was desperate, and I was the only non-revolting option," I admitted miserably.

Sarah sighed, "You really need to work on your self-esteem. No. Think about it."

I raised my head to look at her. She met my gaze with exasperation.

"Okay, work through it with me," Sarah instructed. "Courtney, who was more known for chasing men off than talking to them, gets blackmailed. As I understand it, you forced her to let you have anal intercourse with her on a Friday. She had two weeks to find a man she was willing to lose her virginity to. But Monday, after only having the weekend, she came straight to you."

"Yeah, she didn't want to run out of time," I grumbled.

"Think like a woman for a minute," Sarah suggested. "Never mind, that never works. Let's see. Oh! Okay, Courtney is a programmer, like you, correct?"

"Yeah." I acknowledged.

"So, what does your decision-making process look like?" She pressed.

"Well, find your options, list pros and cons, find the most acceptable option, and proceed," I replied.

"Okay, so let's assume Courtney followed a similar process. Over Saturday and Sunday, Courtney compiled her options, listed pros and cons, found the most acceptable option, and decided on you." Sarah pointed out.

"And? Once you make your decision, there is no point in delaying, so what?" I grumbled.

"Do you not think it odd that Courtney didn't need to spend more time gathering her options?" Sarah guided me. "Or that you were already on her shortlist of candidates?"

"Wait, what are you saying?" I demanded.

"For fuck's sake, Tom!" Sarah groaned. "She already liked you!"

I blinked. "But she never..."

"Of course, she never talked to you! It was terrifying! There was no doubt in her mind that she had a reputation. She's never been good with men, and being raised the heiress to a fucking fortune doesn't make for an easy childhood. Some make it out okay, but your odds, as a rich baby, are about as good as a kid actor in Hollywood. For every famous trust fund baby that actually makes something of her life, you get a freaking Paris Hilton. And Courtney was right on track to be the next Paris Hilton." Sarah exploded.

I winced, most people I knew had an... unflattering view of Paris Hilton.

"Sorry about that... I try to remain professional, but damn it... Why do guys have to be so dense sometimes?" Sarah grumbled.

My brain was still catching up to things.

"So if... but..." I muttered.

"Yeah, she might have gotten the courage to talk to you eventually, but as soon as she knew she was going to be getting fucked, she knew EXACTLY who she wanted to do it," Sarah informed me. "She'd already done her research, and weighed her options, she just lacked the courage to MOVE on it."

"And then I blackmailed her," I muttered, feeling once more like shit.

"Oh, she forgave you for that as soon as she learned it was you," Sarah informed me. "I mean, she hated the fact that she was stooping to cheating, she hated that she didn't have the guts to just ask you out, and she had seen you keep your distance because of her reputation. It sounds like nothing short of the blackmail could have gotten her moving in the right direction, and so while she hated sending all the pictures and doing everything with the 'blackmailer' she was wishing she had the courage to send the pictures to you and make the moves on you."

"So... if I had just asked her out..." I realized.

"She probably would have had a panic attack and rejected you as a gut reaction." Sarah assessed. "She didn't exactly have the best coping mechanisms. She's come a long way."

"No thanks to me," I grumbled.

"Oh... my... god..." Sarah groaned. "Fucking you was the healthiest coping mechanism she'd had in years. Then getting the harem together has helped her socialize normally... or more normally... You have done fucking wonders for her. And not just wonders while fucking her."

"...Really?" I muttered with doubt.

"Really, really." Sarah snipped. "So while, yeah, I was disappointed in you for a few minutes, by the time we finished the session where she confessed to me about it I'd forgiven you... Besides, it was entirely uncharacteristic of you... I am generally not one to believe in a higher power, but... there must have been something in the water that week or something."

I had to admit, I hadn't exactly been myself while I was blackmailing Courtney. "I kinda figured I got drunk on power or something."

Sarah cocked her head in thought, "No if that were the case, I'd have expected further signs of that side of you showing through. But if anything, the more power you've gotten the farther you've strayed from the 'blackmailing rapist' persona."

I shrugged.

"So, in summary, you are a good man who made a mistake for... what was it, a couple weeks? Then you became a diligent lover, boyfriend, tutor, support, and friend. So, aside from Courtney and me knowing about your brief lapse in judgment, all the members of the harem had only seen the diligent lover, boyfriend, tutor, support, and friend. What reason would there be to leave? And the more your harem grows, the more appealing it is to join.... For those that are already inclined to alternative lifestyles... and the more tempting it will be for someone to try to step in like Mary to try to snatch you up," Sarah warned. "Mary seems to be accepting the harem life, but I'm watching for the girl who's going to try to steal you away from us."

I laughed. "I'd be an idiot to leave."

"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."