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Too Good To Be True Ch. 32

Dear Readers,

I'm gonna have to just stop apologizing for taking my time putting new chapters out, it feels like I am always opening with "sorry this took so long". I did enjoy writing this and I hope you enjoy reading it. I don't think I have any really big trigger warnings to put on this chapter, except for it is erotica and there is sex, but if you've gotten this far and you aren't okay with that... I question so many things about you... So, enjoy the chapter!

~NaughtyPaladin

P. S. I'm sorry this was a touch slow! I swear I posted this a few weeks ago... but apparently I didn't. Sorry for that. It's here now!

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Chapter 32

As the first of our two weeks at our haven in Rhode Island came to a close, with Brittany flying back to our more permanent abode, happy and with a pussy I'd filled with cum this morning when she arrived, I was feeling pretty good

It had been a couple of days since the warning of the Triad's intent to expose us to the public had been made, and we'd all been laying low. With the exception of seeing lights through the windows at night, people probably thought the resort-like mansion was empty.Too Good To Be True Ch. 32 Ρ„ΠΎΡ‚ΠΎ

In reality it was anything but; I'd been loving having free access to my harem.

"Damn," Tina laughed, flopping on the couch across from me. "You've come a long way since we first got together."

"If you put him through anything like you put me through, I'm not surprised." Debbie chuckled. "Do you have any idea how much weight I've lost since you started working with me? I mean look at me!"

I mean, I was already. We'd all just finished in the gym, and all my lovers were lounging in gym shorts and sports bras, and I just loved the view. Mary and Cindy were sprawled on the floor, unaccustomed still, to the brutal workout that had become routine to the rest of us.

"Are my legs still there?" Mary groaned. "They feel like they fell off."

"Must be." Cindy whimpered. "They wouldn't hurt so bad if they fell off."

"Oh, don't complain. Squats are great for your legs and ass." Tina scolded. "If you're this pathetic, maybe I should up the number of leg days each week until you can manage it."

"Have mercy!" Mary pleaded.

"I'm gonna go shower." I declared. "Happy bantering."

I had come to really love this place. The luxurious facilities made living here fabulous. If I ended up living in the Sorta-Sorority house we had back at college, I'd highly consider making some upgrades.

I got out of the shower, and walked into my room, drying myself.

"Hello, Master Thomas." Parker greeted me.

I took the towel off my head and saw her shamelessly admiring my body. I had to smile. I admit, having a personal trainer for a lover/girlfriend has done wonders for my physique. Though it had taken Tina, Brittany, and Lizzy to convince me that it was healthy to have a little bit of fat on top of my six-pack, I still wished it popped more. My legs looked pretty great, in my opinion, with a lean, muscular build, and my arms were more toned than they had ever been.

I'd also gotten more used to being seen naked, at least by the girls in the house, be they the staff or my lovers, I guess they were all technically in my harem now.

"What can I do for you, Parker?" I asked.

"Well, I've been waiting for a time when you didn't have anyone lined up, but I'm kinda realizing that might never happen." Parker explained, then took a second to steel herself."So... would now be a good time for... my first time?"

"Oh, I'd been wondering about that." I admitted. "You and the others seemed really excited about the sexual aspects of the job, but the only one I've been with is Berkley, and just the once with her."

Parker stood waiting anxiously, and I realized she was still waiting for a response.

"Oh, right. Sure. Now's good. I mean, lucky you, I'm freshly shaved." I laughed.

"You sure? I can come back later." Parker worried.

"Nope." I assure her, motioning to my stiffening cock, "You've got me all excited now. It would be a shame to waste it."

Parker's eyes were indeed locked on my hard member as it rose to wave, welcomingly I hoped, at her.

"I mean, you've already been with Ms. Brittany today, and I know... guys can only... do so much..." She admitted, swallowing.

"With all those girls out there, regularly enjoying me, I assure you, we've figured out my limits and every way to increase them." I told her. "I am confident, I can give you a good time, even having satiated Brittany this morning."

"If you're sure. The other girls are all waiting for me to do it, since I'm one of the senior officers. I mean, not that I've been here longer, but my role is... sorry, I'm babbling." She cut herself off, and I realized she was incredibly nervous. It helped that she started shifting her weight from foot to foot and was obviously trying to do something with her hands to keep from wringing them.

"It's cute." I assured her.

"Cute? Ha! Haven't been called that since I was twelve." She snorted. "Sorry, I'm trash at bedroom talk and stuff. Well, anything to do with actual relationships. I get panicky. First time a boy asked me out, after Judo class, I threw him across the room in a moment of... I don't know. I swear he was fine once the cast came off... But that was the last time a boy tried asking me out in High School, and college really didn't sound like my thing, so I got into Personal Security, and that really didn't help my image either."

I couldn't imagine a gorgeous girl like her NEVER getting asked out, but I could admit to myself that when she was in her "security mode", she was pretty intimidating. The fact that I'd been around her enough to know she was usually packing at least a pair of pistols, along with iron knuckles, a taser, and a knife, though those were less likely to be required and she admitted to it... Okay, I guess knowing her from our week together had gotten me past the "she's gonna eat me" phase, because she often looked that way, rather than the softer, more fun and friendly girl I knew, or the timid and nervous girl in front of me now.

"Well, their loss is my gain." I told her. "Relax, take off the suit coat and we'll do this."

"Straight to business, I guess." She took a deep breath and took off the suit jacket that was her upper body armor.

"Well, I'm not just gonna have you lay down and spread your legs, if that's what you're expecting." I assured her. "Some of the girls can get off on that, but it's not exactly a great game plan for your first time."

"So... what do we do? I'm not really sure." She admitted, and I was glad to see she'd left her firearms and hopefully the other weapons in her office.

"Well, you comfortable in that?" I asked.

"Yeah," she concurred.

"Then let's just cuddle for a bit, help you unwind. You want to be loose for this." I told her, sitting on the bed and patting the space next to me.

"I thought guys wanted a tight body to fuck?" She wondered, awkwardly sitting on the bed as she kicked off her shoes.

"A tight pussy is great." I explained. "A rigid, stressed out partner, not so much. Your pussy can be tight while the rest of you is relaxed."

"Good to know." She accepted.

I gently drew her next to me, her hands gingerly touching my bare chest, before allowing herself to lean against me.

"Does it feel weird, being erect?" She asked, staring at my dick.

"Nah, you get used to it pretty quick once you hit puberty. The first time was weird, but after I figured out what was going on, it was fine." I told her. "You can touch it if you want."

She reached out and stroked it with a finger.

"Berkley said it was really good, so I'm trusting you. Just tell me what to do." Parker admitted. "I didn't get to be a twenty-three year old virgin by having a clue what to do."

"Just relax." I told her. "You can wrap your hand around it and stroke it if you want, but I'm hoping that I won't be climaxing in your hand."

Parker nodded. "Berkley did say it felt really good, you cumming inside her. I'd like that, if it's okay. I'm on the pill."

"My pleasure." I assured her.

I could feel her getting more comfortable as she gently played with my erection. "It's kinda funny, I don't know why I was always afraid of these. It's just..." she pinched her fingers around me and ran her fingers up and down the shaft, watching the loose skin cover and uncover my head.

I gently put a finger under her chin, directing her face toward me and kissing her. Her fingers tightened for a moment on my rod, then I felt the tension go out of her until her hand fell down naturally cupping my balls, as those two fingers remained on my shaft.

"That's... really nice." She breathed.

"Isn't it?" I grinned, then kissed her again. She gently experimented with kissing me back, and I was confident she'd figure things out pretty quickly.

I gently reached over and cupped one of her shirt covered breasts. I could feel a lacy lingerie bra under the white button-down.

"Oh...!" She gasped. "That's... different."

"Want me to stop?" I clarified, my hand still on her.

"No." She assured me, her hand tightening just a touch reflexively. "It's just... it's never felt good before."

"Courtney says boobs have to be in the mood." I told her, beginning to gently squeeze and massage her bosom.

She closed her eyes and breathed deeply, her hand seeming to have a mind of its own as she allowed me to fondle her and then slowly unbutton her shirt. The purple lace of her bra came into view as her shirt drifted open.

"The girls said it looked good on me." Parker blushed.

"It's lovely." I assured her, and slipped a hand inside to fondle her inside the shirt.

Parker took a break from stroking me to lose the shirt, and I kissed her again as I got both hands on her boobs.

I could feel her arousal growing, and was glad that her tension and anxiety seemed to melt away. At last, I reached around and unlatched her bra, tossing it on top of the button-down on the floor.

The smoothness of her bare breasts felt perfect in my hands, and Parker just laid back, letting me do what I wanted with her exposed chest. Her nipples seemed large on her boobs, like raspberries on the mounds of her womanly assets. She moaned as I gently began pinching them and running my thumbs around the pink disks of her areolas.

"Oh!" Parker yelped, then melted, as my tongue swirled an erect nipple. "Oh, you can keep doing that."

The pleasing texture of her boob and nipple in my mouth made my cock twitch, and I could feel my own arousal rising. I wanted to be inside her, to feel her body around me, but I wasn't so taken I couldn't do it smartly.

With the hand that no longer had a boob to fondle, I first unlatched her belt, then her pants. It wasn't until she lifted her hips to allow me to strip them off her that I was even sure how much she was even aware of me doing it, as she ran her fingers through my hair, and pressed her breast into my mouth.

I ran my tongue along her underboob, and she swooned, allowing me to slip her pants down her legs to join the bra and shirt on the floor. The matching purple lace thong was now the only thing covering her, other than nylon stockings that came up to her mid-thigh. I could feel a touch of nervousness creeping back into her.

My hand caressed her thighs, before sliding into her most intimate region.

"Perfect." I whispered in her ear. "You are amazing."

"Glad you-oh... fuck." She gasped as I began stroking her sex through the silk. "That is..."

Whatever it was was lost as I began kissing the side of her neck, fondling a breast as my other fingers continued to stoke the fire between her legs. She was breathing very hard, eyes closed and legs naturally spreading wide as the lacy lingerie between my fingers and her sex got soaked.

I must have been taking too long, because she reached down and nearly tore off her panties tossing them carelessly across the room. The pleased purr she made as my fingers began to play with her bare slit made my cock throb. Moving between the swelling tip of her clitoris and the sopping wet opening of her vagina, my fingers were working their magic. Her hips began to squirm, rubbing the blonde hairs of her pubic mound against the palm of my hand as she climbed that peak.

With a cry, her legs kicked out and one hand grabbed a handful of sheets, the other squeezing my cock tightly, and pleasingly so.

She jerked and gasped as she climaxed. I took the opportunity to shift, my chin beginning to grind on her clitoris as my tongue explored her still virgin sex. Finally seeing it, I was struck by how lovely every pussy is, in its own unique ways. While the tiny opening I was about to stretch the shit out of was enticing, her long thin slit was incredibly sexy. I lapped at her womanhood, enjoying the pleasing saltiness of her fluids.

"Fuck, fuck, fuck, fuckfuckfuckfuckfuck!" She whimpered, then started jerking again.

I pulled back. That had probably been excessive. She was probably nearly crazy with the unfamiliar sensations. After climaxing she must have been crazy sensitive, probably why she came again so hard and fast.

"Fuck!" Parker finally breathed a minute later when she had control of herself. "Is it always that intense!"

"No, I probably went a bit harder than I should have." I apologized.

"Well, don't stop now!" She urged.

"You're ready?" I was a bit surprised.

"Why not!? It's all been... fuck!" She struggled for words.

I slipped between her widespread legs and began rubbing myself against her. Her sex quickly covered my length in her homemade lubricant. Seeing how much she was enjoying it, I began humping her slit, the folds kissing my cock and Parker pressing her clit up against my length.

"Doesn't... doesn't it go inside?" She demanded, "Like a tampon?"

"It does, but you're enjoying this aren't you?" I replied.

"I mean, it's good... okay, I really like it, but Berkley said... it hurts at first then gets better than anything she'd ever felt! I want that!" Parker pleaded.

Two more thrusts against her clitoris, then I gently pressed into her opening.

"Oh... shit..." Parker breathed, as her opening stretched, trying to let me in. I had to press a bit harder, and her sex finally relented, allowing my head to enter her. Her hymen caught me as I entered, the membrane seeming to be thicker and stronger than any other I had had the privilege of obliterating.

"This might sting." I warned

"Do it!" She begged.

I thrust with my hips and felt the resistance... and release. The heat of her body accepting it's new deflowered state, and the blood of her virginity, gave me that rush of satisfaction, and with her hands on my hips, encouraging me, I began thrusting further and further into her as Parker bit her lip and whimpered.

As the last inch of my length finally disappeared into her vice-like pussy, she threw back her head and cried in ecstasy. Feeling encouraged, I latched my mouth once more on one bright pink nipple and started fucking with abandon.

"YES! YES! YES!" Parker swooned. "OH MY FUCKING GOD!!!"

I felt her body building and raced to try and get her another orgasm before my inevitable climax. It was going to be close. I pinched her pert nipple, and knew this was it. I thrust deep into her and exploded, my sperm flooding her intimate depths, triggering her own explosive pleasure.

Her thighs clamped around me, holding me against her cervix as my cum gushed into her womb. The trembling legs refused to allow a millimeter of retreat, seemingly trying to force me into her womb, though my cock was already making out with its entrance.

After my eighth stream of semen filled her womanhood, I was done, and Parker fell limp on the bed, panting hard, her breasts seeming to be leaping in celebration of the occasion.

"Holy shit." She breathed. "Berkley was underselling this hard."

I pulled out, watching the mix of cum and blood run down her thighs and ass. I'd never get tired of admiring a vagina I'd just gotten the privilege of deflowering. It was just... so damn sexy.

"You were a damn good fuck." I assured her honestly.

"Good." Parker laughed, "Because I'm not sure how I'd gather enough brains to think to do anything else while that's going on."

I smiled and laid down next to her to cuddle.

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"We have a week left." Courtney mused as the girls all relaxed. "Anything in particular people want to do before we leave?"

"I'm guessing naked beach sex is still out?" Debbie sighed.

"Absolutely." Courtney stated bluntly. "With the Triad looking for dirt on Tom, there's no way that wouldn't blow up in our faces."

"Any word from your dad?" Khloe asked.

Cindy perked up. She'd enjoyed our romps, but she knew it was on borrowed pleasure. She needed a possible long term partner, and Courtney was beginning the process. She'd asked her father to see about setting up a social event where Cindy could check out the options that had been discussed.

I mean, they looked good. That wasn't surprising for the rich sons of wealthy families. Not only could they get the best dental, orthodontic, and health care, but Courtney said almost all of them likely had personal trainers. Just seeing how much Tina had been able to do with my sorry ass, I wasn't surprised that they were chiseled and good looking. I mean, there were plenty of others that were, well, not that, but at least to start with the harem members agreed she should check out and meet the "gorgeous ones". So this social event would be like an unfilled episode of the Bachelorette.

"I actually just got an email, I was going to tell you about it." Courtney remembered. "There is an event tomorrow night, a formal dinner party. I think all of the families we were looking at should be there."

Cindy swallowed nervously.

"You're the perfect balance of cute and beautiful." Berkley assured her. "Especially coming with connections to the Carmichael family, you'll possibly need to bring a stick to beat the boys back."

"I'll believe it when I see it." Cindy mumbled.

"Anything else?" Courtney asked.

"Well, I know I slowed things down," Parker admitted, "but I think most of the staff girls will be very disappointed if they transition to your more permanent residence with their virginities intact."

"We may have gotten them a touch overly excited about our experiences." Berkley admitted. "The few fears that remained of the 'Hugh Hefner' employment situation, where sex was mandatory, but he wasn't even enjoyable, are long gone."

"So... we'll want to figure out a way to make that happen." Parker admitted.

Ruth thought about it. "Well, let's see, we have you two taken care of, though you'll probably want a round two shortly, if you aren't already. So that's twelve girls? Hmm... that may be tight. Tom, think you can manage morning, noon and night for a bit? Because while I think we could... we really rather enjoy your cock, so abstaining is a last resort."

I started thinking about the women who'd been giving me looks and parading themselves around anytime I was in the room.

"I think three-a-day is workable." I declared. "Wouldn't be the first time I did that."

"The girls will be happy to hear that." Berkley noted.

"Do you have a schedule for them? I can try and work around that." Ruth requested.

"We can give you that." Berkley assured her.

"And all the girls are on birth control?" I verified.

"Yes, and we've been monitoring to make sure they take it." Parker noted. "Since none of them are keen on having children yet, that hasn't been an issue. Just making sure none of them have hidden intentions."

 

I nodded remembering the discussions we'd had.

"Another thing." Berkley brought up, "Uniform discussions with the girls have brought up a valid concern."

"Oh?" I wondered.

"While some of the girls are willing and excited to do anything you want with you, others are worried about things like not being sure they want to do anal, and the consent indicators we've discussed previously, like not wearing panties, were exclusively all or nothing." Berkley explained.

"A very reasonable worry." Abby declared, one of the few in the harem to still refuse anal.

"It was also brought up that hormones and other things, depending on the point a girl is in her cycle, might make you just pulling up her skirt and doing a panty check feel... violating." Berkley continued. "So it was suggested that we use an indicator that can be seen without having to invade the woman's personal space."

"Okay," I acknowledged. I could see the objections. "What are you suggesting?"

"Mia suggested we use these." Berkley explained.

In her hand she held a few scrunchies, and other hair ties.

"Hair ties?" I asked.

"Color coded hair-ties." Berkley explained. "And we've come up with a key that we can use to let you know what a woman is available for. For example, wearing a blue hair tie indicates that the woman is willing to let you do anything you want to her. A red hair tie, however, indicates she is not interested in sex acts at the moment. Pink indicates vaginal sex is requested, brown indicates anal is requested, white indicates she wants oral. Yellow indicates she is okay with anything below the waist, and Green indicates that all a woman is accepting is being groped. A dark version indicates she is okay being groped while you do so, but lighter indicates she wants you to restrain yourself to the act alone."

I blinked. "That's pretty efficient."

"If we come up with anything else, we'll let you know." Berkley explained. "And on the groping, we talked about if there would be any sort of restrictions, like only legs, or only breasts, but the agreement was generally that if you were okay being groped, then they're okay with you groping what you want."

"Hot." Ali noted.

"Alright, I'll have to write that down for a bit until I get used to it." I admitted. "But it will be nice knowing everyone is giving specific permission."

"That's what we decided too. I told them you'd agree." Berkley smiled.

"Anything else?" Courtney asked.

"You know what I want." Mary lamented.

"Once we're back home, your probation will be half over." Sarah assured her. "Keep up the good behavior and you'll be a full fledged member in no time."

"It seems like a shame to be here on the beach and not do anything with the water." Abby noted. "Could we rent a boat and go water skiing or tubing or something?"

"There's a marina that dad and I usually rent one from." Courtney acknowledged.

"I'll watch the weather and see if we can't find a good day." Abby offered.

"Remember, this is going to be a public outing, so we'll want to be sure to avoid anything a stray paparazzi could catch." Parker noted.

"I'll be the one picking up the boat." Berkley noted. "There is a dock we can use on the beach for actually boarding."

"Sounds good." Courtney accepted, clapping her hands excitedly. "Any other requests? Speak now or forever hold your peace."

And so the plan was finalized.

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"Still nothing?" Trish demanded.

"The guy's got no internet presence I can find." Nathan hissed through gritted teeth. "Image recognition software's going nowhere and AI is hallucinating because it doesn't want to fail."

"Useless." Trish huffed.

"Give me a target, and I can hack it. Give me nothing and I can't. That's like asking you to edit a blank page!" Nathan countered.

"Easy both of you." Emilia soothed, "What's got you two so worked up?"

She loved that they didn't know she knew about their stupid bet. She was still deciding which she would have plowing the other, but it was fun watching them squirm nonetheless.

"We just... need to be the first to nail down who he is, and find something we can smear him with." Nathan huffed. "Everyone's got some dirt that can be aired."

He tried not to think about what Emilia had written in her diary last night. Emilia was wet for him, and he knew it. She bent over to get a drink and he could see the hint of the purple thong she'd written about dreaming he'd fuck her while she was wearing.

The only problem was she also wrote about how nervous the idea of sleeping with a coworker made her. Especially since he was such a crucial part of her team. He needed to find the right time to gently seduce her, or it could blow up in his face.

He tried hard not to glance at Trish. She should know he knew almost everything that happened on a computer in their shared apartment, and she had ordered a twelve inch strap-on. That thing would rip his ass apart, so he was determined to win more than ever.

Trish looked at the purple color of Emilia's thong and smiled. It was lesbian violet. Emilia was preparing to flash some sign to some lucky girl, and Trish really hoped it would be her.

Emilia just smiled to herself as she straightened, knowing the conflicting signals she had just sent. She was also loving seeing Nathan squirm after she had slipped into Trish's room last night and ordered that 12 inch strap-on. She'd cancelled the order before it shipped, but she'd done that by phone. Nathan could peep on all their internet activities, but unless she was crazy, he hadn't bugged their phones to listen in on their calls.

She got a thrill knowing she'd probably just made Trish's panties wet and given Nathan a boner, with practically no effort.

"We're pretty sure they're still at the Carmichael estate?" She asked, sipping her lemonade, part of her wanted something stiffer, but it was too early in the day.

"Yeah, but before you say anything, no." Nathan sighed. "Ever since Mr. Carmichael divorced last year his cyber security team has really stepped up. I might be able to get in, but it isn't worth it if I spend the next year in jail."

Instead of fucking both of you, they all heard in their heads.

"How's tracking the Carmichael's private jet?" Trish asked.

"They rent it out, so it's hard to tell which flights are them, and which ones are rentals." Nathan admitted. "I did sniff an email from one of my bots, and it seems like there's going to be another one of those posh dinner parties. If the email is right, Ms. Carmichael will be attending, and bringing her new boyfriend."

Nathan and Trish looked at Emilia.

"Same circle as last time?" Emilia noted. "I should be able to make that work. If she's debuting her boyfriend there, it's gonna be big."

Nathan and Trish both had their stomachs doing cartwheels. If they couldn't find anything out before the party, the odds of anyone else doing so was slim. But at a party like that, Emilia was guaranteed to get his name. A simple introduction was all that would take. They'd have their story the next day. So both of them were on a timer. Whoever got between Emilia's legs before they article dropped on Friday morning would own the other sexually for a year.

Emilia just smiled as the two eyed each other. Which one would she let do the honors? And which would she condemn to being the other's plaything? One of them was getting it, she'd decided that much. Technically, since both required sexual "conquest" of her to win, all she had to do was wait until after the article dropped and both would lose.

But where was the fun in that?

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By the time I made it back to my room, apparently Ruth had already made the schedule and Amy, her french maid outfit immaculate, was kneeling on my bed. She had dark yellow ties in her hair, and thinking back that meant anything below the waist, and dark meant groping was encouraged. My erection was immediate. Amy had been flaunting herself since our first day here, loving the sexy maid outfit she was wearing right now. Carefully bending and popping out her ass to make her skirts and petticoats fluff up so her ass was exposed to me every time. She'd said she was going to come to me a while ago, so we could do this, but she hadn't shown.

"I promised you a few nights ago," she declared, blushing as she smoothed nonexistent creases from her short skirts, "but... then we realized it wouldn't be right for me to... before Parker."

I shed my clothes so fast, then closed the distance and put a hand under her chin, "Then I should make up for lost time, you've been a very patient girl."

She might have moaned if I hadn't cut her off by kissing her. Her hands went to my chest and she immediately removed my shirt so she could feel my bare skin. I laid her out on the bed, our lips locked together and reached up her skirt, feeling her inner thighs, and discovered not only was she not wearing panties anymore, but she was making a wet spot on the sheets.

She was a kinky little thing for sure. I still wasn't taking her virginity without undressing her, so I withdrew my hand from between her legs and lifted her from the bed, pulling the corset back ties and letting them loose before pulling the dress up and off of her. Her pushup bra joined it on the bed, leaving her naked.

She was petite, and sexy, even if her breasts were only a tease. Barely there, but as I sucked on her nubs of nipples, she didn't react any less favorably than Parker had with more than twice the mass. I was still able to grope her tiny mounds a bit, but instead of dwelling on what she lacked I got down and with a slight encouragement, she lifted a leg and I got a handful of her tight ass. She seemed to really like that, wiggling excitedly as I pawed her posterior.

"You can..." she panted, her excitement clearly rising as her body responded to my touch, "... take my ass... after..."

Damn! She was kinkier than I thought! Wanting to go for both holes on her first time? That was brave and freaky. Who was I to deny such a horny request?

I slipped my hand around and slid a finger into her tiny entrance, my arm trapping her leg directly vertical as I fingered her as deeply as I could without prematurely popping her hymen. Even with a single finger, she was so tight. But even so tight, she was so wet, it felt like she was already lubed, my fingers were coated with her serious lubricant, slipping in and out with ease.

"After I claim this?" I growled, pumping my fingers. Fuck, this was hot.

She just shuddered and nodded.

The looks she'd given me, the number of times she'd flashed her ass at me as I walked the halls. All of it played in my head and I needed to be in her. She was so fucking wet, it wasn't like she'd really need foreplay at this point. With her leg held like this, she was exposed and available...

I withdrew my slicked fingers from her sex, straddled the leg I wasn't holding and pressed my cock against her folds, feeling the wetness coat me. I slipped down her slit and angled as I was, her pussy stretched easily to let my head pop inside her. Her delicate hymen popped nearly as soon as I touched it, making her flinch, but she just tugged on my thighs, begging for more. I pushed, and found her insane wetness allowed me to open her in one slow thrust, where Parker had required multiple thrusts. The tight, silken sheath of her body slipped over my length as I began slipping in and out of her.

Amy just moaned as her intimate depths were claimed. Her shoulders rose as she was filled with the sensations. She was so wet the excess was running down the thigh between my legs. I pulled her other leg tight, so that when I thrust all the way into her, her leg was pressed against my chest until her leg extended over my shoulder.

Her cries of pleasure with each thrust, in time with the slap of my body against her leg, made a symphony of sex as I showed her the wonders of fucking.

The minx had made me too damn horny to be satisfied with simple fucking though, and I got the feeling she wanted it, so I went for it. My thumb pressed into her pussy, slipping in alongside my cock, stretching her tightness even further and making her gasp and her eyes roll. I moved them in alternating motions, the slickness her body produced making them slide smoothly.

Amy was past words, her arms pulled up in a t-rex pose as her brain was overwhelmed in the best way possible. The look of ecstasy on her face told me she was loving everything about her first time, despite my horniness making me go a little crazy with her, so I decided to push the envelope further.

I pulled my thumb from her tight pussy, making her groan in disappointment, before I took the digit, slick with her body's natural fluids, and pressed it against her exposed, unexpecting anus. Not expecting anything, Amy's backdoor was completely relaxed, seemingly assured that its neighbor would be receiving all the attention, so it gave no resistance as my thumb slipped a knuckle into her second fuckhole.

Amy's eyes widened and her mouth worked, but no words came out. She still pulled at me, asking to continue, so I began working my thumb into her booty. The slickness from her pussy lubed her ass as well as the bottle of artificial lubricant on the bedside table, just in reach, ever could. Before long, my thumb was pumping in and out of her rear as my cock plunged into her pussy.

Amy writhed as both our pleasures built. The tightness in both holes built as her body clenched in anticipation, then the dam broke. Her body bucked beneath me, and she screamed in orgasmic bliss. Her tiny breasts jiggled perfectly as her body shook as much as she could locked in place, her legs wrapped up in my body.

Causing my lover such pleasure was always exhilarating for me, and the rush pushed me over. I pressed deep into her pussy and shot my load, taking her defloration to completion. Amy wrapped her leg around my thigh and pulled, trying to force my cock deeper into her pussy as she was flooded with the hot, thick fluid.

I began the exercises I had nearly mastered at this point to allow me to remain erect, doing short thrusts to keep stimulation that would help keep me going. Amy just laid back, basking in the afterglow.

I withdrew my thumb from her butt, and in a quick motion, pulled my cock from her pussy, and pressed my cock's head against the star of her asshole, and gently pushed. Relaxed as she was, her ass gave no resistance. My cock slipped a few inches in, the amazing lube her body had produced doing God's work.

"Oh fuck..." Amy groaned, her first words since she had given me permission to do just this.

"How's that?" I grunted, thrusting more and slowly working into her second hole. Her legs relaxed to let me have my way with her, and her eyes closed in concentration as she relaxed.

"It's... as good as they said... God, such a stretch. Your cock seems much bigger than your finger." She panted.

Encouraged, I worked until I could feed every inch of my cock into that tight pucker. Finally, I got to where I could do long, quick thrusts, withdrawing until my head caught the ring of her sphincter, like her ass didn't want me to stop, then I could thrust all the way back in. My hips slapped against her ass as I fucked her with abandon.

Amy was a ragdoll, any cares or thoughts washed away in a sea of pleasure as her ass surrendered completely to me. It felt amazing and the trust I felt was so empowering, as I took her harder.

I felt a climax rise and peak, but I'd already emptied both barrels into her pussy, so I just felt the rush. Watching, Amy's brows started to knit together, revealing her own building climax. A second orgasm from getting her ass fucked, Courtney always said anal orgasms were amazing, and I wanted that for Amy.

At last, she screamed, and I felt the ring of her ass clamp on my cock. Her legs clamped on me, and her arms threw out to grab anything they could, coming up with handfuls of sheets.

Content, I held my cock in the depths of her ass and savored the pulse of her orgasm around me. I fondled her rippling ass as the waves of pleasure washed through her.

Amy twitched and moaned for a full minute, as I slowly began to soften in her, and pulled my cock from her butt. I released her leg, stepping back to view my work. Her anus winked at me a couple of times before closing. A steady stream of cum leaked from the depths of her pussy next to her freshly fucked ass.

"Fuck." Amy finally gasped. "You are as good as they say."

"I know it was your first time," I apologized. "I'm sorry if I got carried away, I've been wanting to do you for days."

"Oh... I loved it." Amy purred. "Wouldn't have had it any other way."

I laid next to her and cuddled her for a few minutes, until she fell asleep.

Knowing I had work to do, I let her sleep in my bed. I dressed and headed out. I shot Taylor a text, "If you want a picture of the latest fucked virgin, she's asleep on my bed."

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

"I have secured a position as a plus-one." Emilia gloated.

"How you do that without actually spreading your legs is a mystery to me." Trish admitted, admiring Emilia's ass in the dress she was wearing.

"You just need to know people." Emilia purred, getting very, very close to Trish, "What their buttons are. Where their lines are." Her hand brushed along Trish's sides, nestling just over her waistline, "And just what you can get away with."

Trish would have gasped, but Emilia's lips pressed against hers, gently. Trish could feel her brain short circuiting. By the time she blinked and came out of her trance, the door to the room was closing and she was trying to figure out what was going on.

Trish smiled, the bet was as good as won.

Emilia smiled, in the hall, walking over to Nathan's den.

"I'm in." She told the hacker. "I'll have a name for you on Friday."

"Perfect. Once I have a name, I'll be able to figure out who this squirt is and I'll know everything about him by Saturday night." Nathan laughed.

"All it takes is a name?" Emilia simmered, moving close to the man, "You say a name is all you need and you'll know everything."

"You know how I work." Nathan answered, confused. "I've done this nearly a hundred times now."

"You've had my name for years." Emilia whispered in his ear, "And you still haven't figured anything out about me, have you."

"What are you-?" Nathan gasped, turning, but his question was cut off as Emilia's lips pressed against his. Her softness and the scent of her perfume filling his head and making him just stop.

She broke off the kiss and he just stared at the gorgeous woman.

"We'll pick this discussion back up later." She winked, then with a click of the door closing she was gone.

Nathan took a second to process before jumping out of his seat and into the hall. Emilia was nowhere to be seen, but Trish was entering the hall herself. The two exchanged a look and each smiled, confident they were winning their bet.

Emilia closed the door to her room, the thrill of playing with her coworkers making her wet. She was enjoying the game, but the memory of both of their lips on hers, she couldn't help but think about which one she wanted to win as she sat at her desk.

She had planning to do, and needed to work on the favor she'd had to give Tim Walton to get brought as his "Plus-One" to the event. It was pathetically easy. He wanted this story claiming he was homosexual gone, or at least countered, and while she wasn't about to taint her reputation with a trash article. She did have a proxy set up to feed leads to desperate low tier reporters, like the one who was claiming Tim was gay. She leaked about a few of the parties that Tim had talked about and gave the young, hungry reporter a lead on one of the women Tim had said would paint him in the best light, assuming she'd actually enjoyed her time with him and hadn't just tricked the old, rich bachelor.

 

That done, she began looking through her armory. Which dress to wear? It was tricky, dress too provocatively and she'd draw the wrong kinds of attention and perhaps scare away a man trying to woo a rich heiress. Dress too conservatively, and she'd be too plain on the arm of her rich benefactor, and perhaps appear to be positioning herself as a contender for a man of means and capability enough to pull the young Ms. Carmichael.

She looked at her options and smiled. This was the game, the real challenge. Making chess moves ten turns before her opponent even sat at the table and knew anything was coming.

She wasn't sure which was more exciting, toying with her coworkers, or the challenge of facing down this strange young man.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

"So, are you getting tired of deflowering virgins yet?" Courtney laughed as we got a quiet moment alone to sip the fruit smoothies that Lizzy and Brittany had come up with to help us get proper nutrition.

"Not gonna lie," I told her. "It's still a rush every time."

I leaned over and kissed her on the cheek, "But I'd give it all up in an instant if you asked."

Courtney laughed, and kissed me before I could pull back. "Why would I do that? I think it's sexy. Knowing my man is so amazing that he has women lining up for him, but he still chose me, and chooses me every day. I just don't want to be selfish, so I share you with them."

She took a drink, "Besides, I like watching... and taking part. Having Khloe lick me while I suck you, or having her suck on my breasts while you fuck me... I love it."

"You really liked her licking your asshole while I was fucking you, too." I noted.

"Oh, yeah." Courtney giggled, "That felt really good too."

She looked at the ceiling, "And I'm not gonna lie, licking your cum out of her pussy is hot as hell. Ask me a few years ago where I'd think I would be, and it absolutely wouldn't be here... but I think I'm happier this way then I would be any other way."

"Any regrets at all about how things are going?" I wondered.

"I mean, I regret the reality that you can't always be hilt deep in me, making me orgasm like crazy," Courtney laughed. "But that's just reality... getting in the way of all my fun plans."

"You don't regret having me fucking all these other girls?" I marveled.

"Nah. I mean, I want to know everyone you are with, but I don't mind as long as I know." Courtney assured me. "I mean, you should have seen Amy wandering away from your room. She was almost deliriously happy, though she was having a hard time walking straight."

I grinned. "She was pretty great."

"Did you really fuck her ass the first time?" Courtney laughed. "She looked like she was adjusting to that stretch. I remember that walk."

"She was begging for it." I bemoaned, "Who was I to deny her fervent wish?"

"The fact that you love how a tight ass feels on your cock had nothing to do with it, I'm sure." Courtney teased, wiggling her hips a bit.

"Are you volunteering? Because I would absolutely accept that." I told her seriously.

"You fucked her like an hour ago, you think you could handle me now?" Courtney asked with raised eyebrows.

"I don't have to cum in you, I just have to fuck you until you can't handle it anymore." I informed her. "In fact, once I'm erect, not cumming would make it easier to go until you can't take it anymore."

"Tempt me, tempt me." Courtney grinned. "But I think Elaina volunteered for tonight, I'm gonna see if she'll let me watch. I'd hate to ruin her first time, because I got greedy."

"Elaina did seem like the exhibitionist sort." I nodded. "I think she'd enjoy having an audience."

Courtney finished her smoothie. "I'm gonna go find her. God, this is hot."

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

"What did you need me for?" I asked Berkley a short while later.

"Yes, have a seat." Berkley welcomed me to her office. "Robert has reached out about his plans for you once we return from our vacation."

"Plans? I thought I wasn't starting anything until I graduated." I wondered.

"Do you believe you will be unable to keep up with your school load and basic duties?" Berkley asked.

"I... don't know." I admitted. "I'm taking more than a full-time load in order to get the business minor. Putting anything on top of that, and I am going to be really stretched thin."

"Then it is a good thing that you'll be getting your first personal assistant." Berkley replied. "She'll be helping you to adjust to your new responsibilities and making sure you still have the time you need to complete your schoolwork."

Another member for the harem I guess.

"Alright, so what all does he want me to do?" I sighed.

"You will be starting doing basic tasks of low-level analysts," Berkley explained. "As you get nearer and nearer to graduation, you'll be moved up the ranks so you understand what each level of employee does. When you graduate, Robert will be putting you in an upper management position, so he wants you to learn what that entails."

"I guess that makes sense." I acknowledged. I thought about the classes I had coming up before graduation. "This is going to be one hell of a year."

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

There was serious preparation to be had for the dinner party. Cindy needed a dress formal enough for the event. We only had one day to get it done, so it was going to have to be a rush event.

"I'll have Elaina bring the limo around and you two can go shopping in New York, like we did for my dress." Courtney offered.

"Do we have any vehicles other than the limo?" I wondered. "I'd rather not draw that much attention."

"We have a couple SUVs and a few Mercedes sedans." Elaina offered.

"The sedans probably have better gas mileage and will be easier to navigate in New York's traffic." I assessed.

Elaina smiled at Courtney, "Have I said before that I like him?"

"I don't know, but everyone says it eventually." Courtney answered smugly.

So a short time later, Cindy and I were seated in the back of the white sedan, Elaina driving us into the big city. Brinley came along as security.

Elaina dropped the three of us off at B&B Couture and Brinley led us inside.

"Welcome back, Mr. Tom, where is Courtney today?" Blair greeted me as we walked through the door.

"I'm here getting a dress for my sister." I told her.

"Bringing the whole family in?" Blair smiled broadly. "It is a pleasure to grow our clientele as always."

Cindy was measured, and they started bringing out stock they had in size for her.

"A little more in the bust, and you would be perfectly aligned with one of the model figures we use." Blair informed her. "If we get it prioritized, we should be able to get the alterations done overnight, though at a price. Otherwise a heavily padded bra will be required to make it fit. We could provide a recommendation to where an adequately padded bra could be purchased."

Cindy was living out her princess fantasies. Twirling in dress after dress on the podium with an array of mirrors in front of her. I just let her enjoy it for a bit, before asking her if she was close to making any decisions.

"How many dresses are there to try on in my size?" Cindy asked.

"We have another fifty or so we could try, but that would take most of the day, and if you want it altered, we must make a decision soon." Blair pointed out.

"Ooooh." Cindy struggled. "I think I have a few I could go with. Can I try the blue one and the pink one again?"

"Absolutely." Blair agreed.

It seemed the decision was between a sapphire blue mermaid dress, with cap sleeves and light sequining, or a pink v-neck dress with elaborate lace.

"Which do you like better?" Cindy asked me, standing in the pink dress.

I had to admit, they both were pretty. The mermaid dress showed off her figure better, but the v-neck dress was backless and showed off her nice little cleavage nicely.

"I'd go with the mermaid dress." I told her.

Brinley nodded in agreement.

"Oh?" Cindy murmured.

"This dress is a little better for young ladies who are slightly more well endowed." Blair guessed. "The mermaid dress does show off your figure very nicely, and I think that is what he was suggesting."

"Oh, I see!" Cindy noted, turning and looking at herself in the pink dress before changing back into the blue once more. "Now I get what you're talking about. I think... I think I'll go with this one."

The dress was pricey, and the rush alterations were pricey-er, but I wanted her to have something beautiful to wear to this event. After all, she was fishing for husbands, and I knew that first impressions meant a lot.

As I waited, I turned to Blair, "I noticed that after I left, the paparazzi couldn't get my name from you guys. I really appreciate that."

Blair smiled, "We are a high class establishment, Mr. Tom, we value our client's privacy. It is nearly mandatory if we are seeking to do business with high class individuals, such as yourself. The amount of business we would forfeit if we were to betray someone like you is astronomical."

"Well, I appreciate it anyway." I told her.

"We appreciate your continued business." Blair countered.

Cindy came running out of the changing room and gave me a big hug, once again dressed in her normal clothes. "Thanks so much! I'm so excited for this."

I couldn't help but smile. As much fun as it was having her in my harem, setting her up for the long term was what I had to do if I really cared about her.

Waiting outside for Elaina to come pick us up, I could only think of the contrast from the last time I was here. No one noticed me, no one was taking pictures, and there wasn't a swarm of paparazzi trying to get pictures.

Traffic in New York was still garbage, and it took us most of the day to get back. The smell of dinner was in the air by the time we got back.

Lizzy had made another one of her masterpieces.

"Bacon? I thought we had a healthy diet, not that I'm complaining." I laughed, seeing the bacon wrapped steaks.

"Being healthy doesn't mean you can never have nice things." Lizzy teased back. "It means you have to have it sparingly and in moderation. With solid nutrition on the side."

The side dishes were laden with vegetables, and who knows what else, but it was freaking delicious, so I didn't care. The only problem was Tina raising her eyebrow at me as I went to get seconds, and I knew if I overindulged, I'd pay the price in the gym later. So, delicious as it was, I restrained myself and didn't overeat.

As I sat contemplating my day, I remembered Courtney saying that Elaina was going to get her chance to take me for a spin in bed tonight, and I noticed that Courtney had slipped out.

I checked my phone, but there was no indicator I should hurry, and it was usually better to take some time to digest before a thorough fuck.

Once I was feeling settled, I texted Courtney, "You two ready for me?"

"Oh, we're ready." Was the response.

I tried to remain calm on the walk to my room.

Inside, on my bed, was the hot, nearly-naked Latina. She knelt, her face flush, wearing only a thin, mostly-transparent, draped, dark green, lace nightie, that barely reached her hips.

"I've been waiting for you." She purred.

By the smell, she had been waiting most anxiously. I'd thought Amy had left a wet spot on the bed, I wouldn't be surprised if Elaina was kneeling in a puddle.

"Fuck, I love my life." I breathed, and reached for the hem of my shirt.

"Ah-ah-ah-ah-ah!" She interjected, rising from the bed and walking to me. "That is my job."

I caught her hand and turned, pulling it high over her head and pinning her against the wall. "I thought you said you wanted a man with a spine." I told her. "A man you can't push over, and now you're here telling me what to do."

I swear Elaina almost came right there, but she caught herself and met my gaze. "Just because I cannot push you around, does not mean I cannot spoil you. You are a king among men, and deserve to be treated as one."

Then the first sign of nervousness appeared as she broke away from my gaze, "And... I am afraid. It will go better, I think, if I am in control, if I can choose my pace."

"I'll allow it." I told her, and let go of her hand.

"Then allow me." She simmered.

She gently kissed me, then again, and I realized she did not have a lot of experience kissing, but she was a fast learner. She quickly grew in boldness and passion, pausing only a second to lift my shirt over my head. I kicked off my shoes as she fumbled with my belt, then the button on my pants. Finally, she let my pants fall and I kicked them aside too. Finally, she stopped kissing me, looping her thumbs in the sides of my boxers and lowering them as she knelt. My erection popped out to wave hello as she reached its level.

"I've seen you, but so close, it is something else." She murmured, then she reached out and licked it.

A sound made me glance over to where Courtney sat, she was naked herself, tweaking a nipple with her left hand, while two fingers of her right hand pumped in and out of her vagina.

Elaina grew in boldness, and wrapped her entire mouth around my cock, gently sucking.

"Mhm... Love that." I told her. "More tongue."

She pulled off. "I'm just getting a feel for it. I wouldn't want to make you cum prematurely." And she resumed her blowjob.

I just let myself groan and breathe as her mouth explored its ability to pleasure me. I knew audible feedback was important for a woman learning to please her man, so I let her know what I liked and didn't.

After a few moments, I felt her try to take me deeper, but gag. Oh, well, we all started somewhere.

Instead, she rose and kissed me, turning me and backing me up to the bed. Getting the message, I climbed on and laid back, my erection standing tall. Elaina took a breath, then shed her nightie, and joined me naked on the bed. She ran her hands over my toned, healthy body, then threw a leg over me, glancing at Courtney who was seated with a broadside view of the bed, and smiled. I could feel her confidence in her sexuality rise as Courtney masturbated watching us.

She took hold of my shaft and pointed me at her womanhood, rubbing me through her folds and seeming to find that rubbing my cock against her clit felt pretty damn good, proceeded to do that for a minute. Either her horniness got the better of her, or she decided she'd got enough of her fluids on me to lube me, and she lined me up with her sex. Once I was nestled in her opening, she put both her hands on the headboard, and gingerly lowered herself, spearing her sex on my cock. At first, her vagina refused to stretch, making my cock strain, until finally the strength of my erection exceeded the resistance of her pussy, and her lips parted for me.

She gave a slight whimper as her body stretched to accommodate my girth, but then she lowered herself another inch. I think she expected more resistance from her hymen, but her weight tore me right through it in an instant, making her jerk, her knees slipped and she plunged down until her pussy was kissing my groin around the base of my shaft. I knew it probably wasn't the best sensation for her, but damn did I feel it as I split open places that nothing had ever been before, and she was nice, slick and tight.

She hissed something that sounded an awful lot like she was swearing in Spanish, trembling as I felt the familiar heat of the blood of her virginity around my shaft. Her body tightened around me as she flinched from the sensation, which felt sensational.

I went to speak, but she just shushed me, then after a moment, she began to rock. I watched her expression change from the stress of her accidental plunge to pleasure as the sensations began to work on her. She started really getting into it, and began experimenting, bucking, bouncing and grinding.

I was enjoying the sensations of her body as her pussy massaged and tried to milk my cock. Elaina was finally getting into it and she threw back her head, moaning and bucking to make her breasts bounce. I saw her glance over and see Courtney pumping herself furiously, and she just went wild. She threw her hands back on my thighs, pinched her feet around my ribs and began not only bouncing up, but pulling herself down to fuck even faster. I could feel my peak rising, glad for the time I'd had to recover from my previous romps, because I could feel another load in the chamber for her sexy Latina womb.

She cried out in ecstasy as she beat me to her peak, orgasming with my cock deep inside her, as the tremors and spasms stopped her frenzied fucking of my cock. I was so close though, I grabbed her hips and helped her through the last few bounces and then erupted into her. I heard Courtney cry out from her chair alongside us, as our audience orgasmed as well.

Elaina's cries rose and fell with the streams of cum flooding her body, making it clear that despite her trembling legs and shaking arms, she could feel every drop gushing into her womb. Damn was I glad for all the tricks, tips, supplements, and dietary planning I was doing to be able to keep my sperm and semen production up for my girls. Elaina deserved as much cum as I could put out. She definitely wasn't complaining, when she collapsed forward, laying on me, spent from her first foray into the world of sex.

I wrapped my arms around her and held her, my cock still buried in her vagina. I lay there enjoying it all, then heard a shutter sound, and glanced down to see Courtney check out the picture she had taken of the newest harem member's defloration. She gave me a thumbs up, then collected her clothes from somewhere and left us to cuddle.

I just chuckled to myself and looked at the young woman on my chest. Her knees slid out from under her, causing me to finally slip out of her, and for her to lay out on my chest. Her chest began to rise and fall, and I realized she had passed out, fallen asleep, or both.

Not that I was complaining, it had been a long, successful day, and the post-sex sleepiness came for me too.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

My dreams of my Latina lover felt so real. I could feel her hand as she began to caress my cock, teasing it, and cupping my balls. I felt a warm wetness wash over me, like a giant tongue, washing me. Then I felt the distinct feeling of a tongue on my cock, licking me from balls to head, where it swirled before lips warped around me.

I woke and found that at some point in the night Elaina had made her exit, and in her place the sexy form of Nikki, my ebony bodyguard, was now tasting my morning wood. A wet washcloth to clean off the evidence of last night lay on the bed a short ways away from my hips. Nikki was still fully clothed, except her suit jacket, which was draped over a chair, and her shoes she had left out of the bed.

"I see you're finally awake." Nikki purred, swirling her tongue over my penis, "You like this that much?"

"Absolutely." I informed her, laying my head back.

"Good. Mom always said this was the best way to wake your man." Nikki murmured, then started sucking again.

"Oh, it seems like this might not be your first time?" I wondered.

She blushed. "I... was watching. Last Night. The cameras in here are pretty good quality."

I glanced up at the black glass dome of the security camera in the corner of the room.

"Taking notes of the others' performances?" I chuckled.

"Well, it seems to be working so far." She shrugged, and began sucking once more.

 

I enjoyed it as she gave me a wonderful morning tongue-bath. But Elaina had spoiled me last night, and I wasn't about to stand by and let another woman do all the work.

I sat up and she rose, letting me kiss her and begin unbuttoning her shirt. Once the garment was free, I tossed it toward the chair her jacket was on, not really caring if it landed where I had intended, and reached up to feel her breasts. The practical cotton bra was a little too padded for my liking so I reached around and unlatched it, sending it to join its kindred garments in that general part of the room. Now able to fondle her properly, her breasts filled my hands nicely, but didn't over fill them. She moaned into our kiss as I gently pinched her nipples.

I felt her shift as she lifted her ass and slipped her pants down her legs. Now confident the only thing between me and both our goals was her panties, I laid her back on the bed and began fondling her breasts in earnest. By the sounds that escaped our kiss, she was rather enjoying it, but she once more lifted her ass and started slipping her panties off, which I helped her with, once I relinquished my grip on one of her breasts and transferred my mouth to it. Tossing the plain cotton panties aside, I rubbed my palm up one inner thigh, and down the other, massaging in a teasing pattern that made her whimper. Her body wanted it, and we both knew it.

Finally, I slipped my fingers between her folds, and found her as wet as I had hoped. It still surprised me that all these women wanted me, but I wasn't going to complain when they did.

She had the most prominent clitoris I had ever felt, and it seemed protruding as it did made it more sensitive. She twitched and moaned as my fingers played the pleasure harp between her legs. She seemed to really enjoy me playing with the opening my cock would be stretching shortly, almost as much as she liked me playing with her swollen clitoris.

I wasn't surprised when this led her to seize and jerk as her first orgasm washed over her. I recognized the signs and went back to focusing on her breasts as I allowed the overwhelmed virgin's pussy to recover. I suckled her nipple and fondled her wonderful orbs, waiting for her sensitivity to pass.

Nikki mumbled, trying to form words, but seemed to have forgotten how speech worked. Her soft exclamations as my tongue caressed her nipples and swirled her areolas told me the distraction was working and she didn't realize I was giving her sex a rest. I didn't mind. Her wonderful chocolate mounds with dark black brown nipples were my treat for the morning, and I was devouring them with glee, and she happily allowed me to do so.

Her hand found my cock and began squeezing and stroking. Her grip was firm, and almost felt as tight as the virgin pussies I'd been plowing, though it lacked the wetness. I knew if she kept that up, I'd be on a timer before I blew my load in her hand instead of her womb, and I didn't want that. If I was going to fuck a virgin, I wanted to fill her with cum.

First, I needed to make sure that her pussy wasn't still too sensitive, and having felt her pubic mound, I knew she must have just shaved. It would be a shame not to reward that.

I moved down and ran my tongue from her swollen clit, down the dark folds of her sexy pussy, to swirl the pink opening that led to her womb.

"Oh... shit..." Nikki finally found words, and her hand stopped pumping my cock as her brain was thoroughly distracted.

I worked my tongue into her opening, worming it in and finding which places made her hips squirm under her. I could feel her clit against my chin as her legs squeezed my head. The rush of pleasuring my lover made me try harder and harder to give her another orgasm.

That was a task I rarely failed at.

Nikki squealed as her legs flung wide, releasing me as she was swept up in another orgasm.

I made my move, climbing between her legs, taking my throbbing cock and rubbing it along her wet folds. Nikki rested her ankles on my shoulders, so I took hold of her legs and pushed my head between the tight lips of her pussy.

"Oh, damn." She grunted as her body adjusted to accommodate the thickness stretching her virgin sex.

I just watched as I began to thrust, inch after inch of my thick white cock slid into her swollen black slit. The contrast was just as sexy with Nikki as it was with Brittany and, to a lesser extent, Suki. Nikki's black pussy lips seemed to suck my cock in and cling to me as I pulled back, her pussy seeming to enjoy me fucking her as much as she was. I noted that I hadn't felt her hymen break, but I knew not every virgin had an intact hymen, so I didn't think much of it. Her pussy felt too good to really care.

Nikki let out a series of high, almost yelping cries, in time with each plunge of my cock into her. Her legs clamped together, vertically, giving me a solid hold and my groin slapped against her thighs as I worked up a rapid pace, pistoning her pussy.

Her sensitive pussy pushed her to an explosive climax, and I had to pull her legs into a bear hug to keep them from pushing away from me and breaking our union. Nikki screamed in pleasure as her pussy clamped around my cock, and I kept fucking with fervor.

I felt my impending climax and upped my pace, Nikki was already orgasming, but I wanted it to be as good as it could.

I thrust deep into her and released, my seed filling her womb. Nikki gave a shuddering moan as she felt the hot fluid filling places she'd never felt before.

"God... I see why Mom had so many kids now..." Nikki groaned. "It's so good."

I held my pulsing length in her depths, depositing every drop of my semen in her. Nikki's body responded by constricting and trying to extract even more.

There was a knock on the door.

"Nikki, you done?" Taylor called. "You wanted that picture?"

"Yes!" Nikki crooned. "I'm ready."

The door opened and our harem photographer entered.

"Damn girl, you lied to me." Taylor laughed. "You told me you 'weren't sexy', but giiiiiiiiiirl, you lied."

I pulled my cock out and watched the thick white fluid start to leak down her dark buttcheeks.

"Gorgeous." Taylor praised, grabbing the defloration pictures. "You look great!"

"I didn't bleed, did I?" Nikki worried. "I swear I was a virgin! I only went horseback riding the one time, and I bled even though it wasn't the right time of the month!"

Taylor gave me a look.

"Nikki, I believe you." I told her. "You don't seem like the type to be lying to me, and they did a thorough background check on you. If Berkley and Clarence didn't believe you, you wouldn't be here. So blood or no blood, hymen or no hymen, you're in the harem now, so I don't want you to worry about it."

Nikki let out a deep breath, "Thanks, I was a little worried about that."

I patted her sexy thigh. "If it makes you feel better, you felt like a virgin. It was great, and I'm honored to have been given the privilege."

"You kidding?" Nikki chuckled. "Mom said white dick was nothing next to a big black cock, but I felt so damn good, and you didn't seem to mind eating my black pussy, so I'm just gonna count this a win."

She started to move. "Oh... but I'm gonna be sore for a bit..."

"That happens, give him a few times and you'll be fine afterwards." Taylor assured her.

"Oh, I may be sore, but I'm still feeling fine. Is this what they call 'Cloud Nine'? Cause I'm loving it." Nikki smiled.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

"You'll want to shower." Courtney told me, as we sat at lunch. "We've both been around it so much we don't realize when we smell like sex, but if we show up to the dinner party smelling like it, it won't be good."

"Fair enough." I asked. "Is there anyone waiting for me in my room before I shower?"

"No," Courtney assured me. "You get to rest for a bit. We didn't want you spent at the party. Cindy will be meeting the boys I think she might end up with, but you'll be meeting the families you'll need to do business with. It is an important event for both of you."

"No pressure." I chuckled nervously.

"I don't want you to be stressed, but when it comes to other people of means, networking means everything." Courtney explained. "So, it is important that you make a good first impression, and don't make enemies."

I swallowed.

"I'll go take that shower."

"This is a formal event, but not black tie. So wear a nice tie, I like the blue one on you, it brings out your eyes. But Cindy will be wearing blue, so go with the red tie." Courtney instructed.

One very nervous shower later, I came out wearing the tailored suit that Courtney liked me in so much, with the red tie she ordered.

"Looking good." Courtney told me, wearing a flowery dress that matched my tie. Or my tie matched her dress. I guess she had the dress first, so that was probably the case. The sweetheart neckline looked very nice on Courtney and the dress clung to her body and reached mid-calf on her.

"Do I look okay?" Cindy asked, joining us in the blue dress we had ordered the day before. "Berkley had it picked up this morning."

"You look great!" I assured her.

"The security detail is ready." Parker told me, "Mia will be watching over Ms. Cindy, and Kat, and Brin will be watching you two."

"One security agent for each of us." I nodded.

"I know." Parker sighed. "But it just isn't practical to have the whole team out at once. Nikki is resting for her night shift tonight, and I'll be handling things when the handoff comes up on your return."

"So, are you understaffed?" I wondered.

"Technically, yes." She admitted. "I'd love to get up to ten members on my team, but I only have five right now. Clarence said we'd get there, but we're starting small."

"Well, if you need anything, let me know." I urged.

"I will." Parker assured me.

"Brin will be driving a second car to bring the security team along with you." Berkley explained. "Elaina will be driving your car, and remember, do not open the door when you arrive before the security team is there. They will open the door for you."

"Is that necessary?" I wondered. "Isn't this a reputable place we're going?"

"The party is at the Tiller family's estate in North Hampton." Parker answered. "The area is well to do, but an event like this might draw attention. You can never let your guard down because you never know when an overly ambitious paparazzi might go crazy, or when a stalker or abductor will show up."

"Alright," I accepted. "I'll leave that to you."

"Luckily, New Hampshire is a permitless carry state, so our girls won't have to worry about a licensing mixup." Parker sighed. "States without concealed carry reciprocity or universal carry are a nightmare for security teams. Especially when they have strict laws like New York. I'm glad nothing happened, but I hate sending the girls into New York because they have to leave their firearms behind."

"Well, I'll count us lucky then." I breathed. I hadn't realized that was such a big issue for them.

"It's nearly a three hour ride, so you'll want to get started soon if you don't want to be late." Berkley urged.

"Off we go then." Courtney declared.

The ride wasn't so bad. Courtney spent the whole time prepping us for what was going to happen at the party. Dinner would be a multi-course event, and alcohol would generally be served.

"Luckily, not everyone drinks, and a few high ranking businessmen avoid alcohol, so I don't think you'll get too much flak. In some circles it is considered a faux pas, but while this is technically a formal event, it is pretty casual for these events."

"I'm not even old enough to drink." Cindy noted.

"So you'll be fine." Courtney assured her. "While this is an event at a private residence, they could still get in trouble for giving you alcohol."

"The most important thing will be not insulting people and building up relations." Courtney explained. "While people might snicker if you use the wrong fork, most of them know that they are being ridiculous. Just remember, use the utensils from the outside in."

We arrived at the Tiller estate. It looked like it had once been some colonial mansion, and was definitely large enough for the event. The well maintained lawn, with layers and hedges, stretched toward the beach. The colonial structure was a mix of red brick, stone work, and white painted wood.

The limo pulled up and we waited until Kat and Mia opened our door and I exited first, blocking the view to make sure there weren't any panty shots as Courtney and Cindy climbed out. My caution turned out to be unnecessary as not even a single cameraman was to be seen. I wondered how they had managed that.

I lead the two girls inside.

There were staff members who led us to a side structure that was serving as a ballroom and dinner area. Given the formal attire, it wasn't like there was a DJ and a mosh pit, but the live music was definitely more modern.

"Your seats." The server indicated.

"Daddy!" Courtney squealed. "I didn't expect you here?"

"Well, I wanted to be here when you showed off your fine young man." Robert laughed from his seat at our table. "Plus, Clarence told me he'd be bringing his sister, and I wanted to meet her myself."

Cindy blushed.

"This is my sister, Cynthia or Cindy." I told him. "Cindy, as you probably guessed, this is Robert, Courtney's dad."

Cindy shook his hand.

"Now, I don't know this lovely young lady." I told him.

"Flatterer." The woman accused me.

She was older, though probably a touch younger still than Robert was, maybe in her later forties or early fifties. She looked fit and healthy, with lustrous, rich brown hair, blue eyes, and a green dress that showed off her cleavage very generously. Far from the excessive chest and fake ass that Brooke, the former Mrs. Carmichael, had, this new woman had a petite waist and a nice, but not oversized booty, and breasts about the size Brittany and Abby had, so about middling for my harem.

"This is Heidi." Robert told me. "We've been talking for a bit now."

"Oh?" Courtney noted in a questioning tone.

"A pleasure to meet you all." Heidi greeted us all. "Robert and I have been having dinner for about a month, but he says that anyone who wants to aim for the status of dating him needs approval from his little girl. Though you aren't so little anymore, are you?"

"Oh, so you brought her to get my approval?" Courtney mused.

"Oh no." Robert assured her, "I don't think a single evening is enough for you to tell."

I glanced around the room and noticed a lot of eyes on our table. It seemed with Robert having a new woman on his arm, and Courtney bringing me out to show off, we were garnering a fair amount of attention.

"Greetings, Robert." A woman with long, dark hair, in a white dress, with a fair amount of jewelry, came over. "I'm afraid I'm not familiar with most of your guests."

"Mrs. Tiller, a pleasure as always." Robert greeted her. "You know Courtney, my daughter." Mrs. Tiller inclined her head. "And this is Heidi Marino, a young lady I've been seeing for a little bit." Another inclination of her head. "These two fine young people are Courtney's boyfriend, Thomas, and his sister, Cindy."

"Boyfriend?" Mrs. Tiller noted, eyeing me up. "And how serious are we?"

"Well, we're waiting until after graduation, but I'd be expecting an invitation shortly afterward." Courtney stated smugly.

That raised Mrs. Tiller's eyebrows, and I noticed Heidi looking at me far more curiously now too.

"Well, we're happy to have such an admirable young man with us tonight, and his lovely sister." I watched as the wheels began to turn in her head. "I'll leave you to your meal. I hope you enjoy your evening."

She hurried away, clearly with a lot on her mind.

"No mercy for the young pair." Heidi laughed. "You two are going to be very, very popular after dinner."

"I have faith in them." Courtney assured her father and his date. "So, Heidi, what do you do?"

"Well, I got into real estate a few years back..." Heidi began.

Drinks, the first place I had to ask for the non-alcoholic option, and hors d'oeuvres were brought around as we chatted.

The dinner menu was brought out shortly later, and it was definitely bougie. It was like we were at the Daniel again, but this time instead I had to actually make my selections instead of trusting the chef.

I ended up ordering lamb, a mushroom and cheese bread appetizer, a lemon and herb chicken side, and a steamed local vegetable dish, along with a craft ice cream dessert. Once I explained my aversion to alcohol, the server (who was assigned to us now, instead of just having wandering servers distributing drinks) gave me the drink menu presented to Cindy and we both ordered juices from the assortment for the cocktails.

It was all as good as you would expect. I mean, Lizzy was really loving having access to the type of kitchen that was not only hers at the house here at the summer estate, but was also in our "sorority house" back at college. She was also loving having access to any ingredients she wanted, so while it wasn't as much of an improvement as it once would have been, I had to admit the chef, or chefs, were good.

After dinner, people began to break off and begin mingling.

"Hello." A pleasant voice called to us.

Turning, there was a young man about two inches shorter than I was, with wavy black hair, light brown eyes and a youthful face that seemed inclined to smile. He was lean and his tailored suit made him look sleek.

"Thank you for coming." He greeted us. "I saw my mother come over earlier and thought I'd swing by to say hi. I'm Kennith Tiller. You can call me Ken."

I remembered that name, and remembering the discussion, I could see why the girls had compared him to Paul Rudd, though he still looked borderline boyish.

Of course, if he was supposed to date my sister, the max 19 years old that he looked was the right age for that. I couldn't remember the ages they had discussed, but if I remembered correctly, both he and the other guy the girls had talked about were her age or just over it.

I found myself feeling protective, but I knew I needed to let Cindy handle this unless she asked me to step in.

"Pleasure." I greeted him, trying to sound friendly. "I'm Tom, this is Courtney and this is my sister, Cindy."

He shook my hand and turned to Cindy, "It's rare to see new people join these stuffy events. Would you care for a tour of the house?"

"That... sounds nice." Cindy accepted, and took his arm as the two walked off.

"So far so good." Courtney breathed quietly to me. "Mrs. Tiller took the bait. We'll see what she thinks of him though. There are options, even if there aren't a lot."

I nodded.

I met so many people, so fast. The number of old to middle aged men who wanted to size up the man Robert Carmichael was taking under his wing seemed endless. I had to be very careful as they casually brought up politics, business policy and the latest trends.

At some point, Courtney got pulled away to talk to some of the wives and dates of the businessman trying to get my measure. I kept an eye on her, and on Cindy who returned with Ken, and was now also talking to a fellow who, if the Stephen Amell comparison was accurate, was Landon Johnson.

"She is quite popular." A soft voice noted, as I stepped away from the crowd for a drink.

I turned to find a beautiful young lady in a tight black dress. Her well endowed chest gave no choice but for her cleavage to show, as her breasts were nearly as large as Debbie's and she probably would have been one of the most busty girls in my harem if she joined. Her figure was nice and curvy with a thin waist and a popping ass. Her long black hair, with the hint of blonde roots showing through, was tumbling down her back, and framed her soft blue eyes.

 

"Yeah, she really is." I noted, looking back at my sister.

"I haven't seen you at these events before." She smiled, "Couldn't bother you for a name, could I?"

"Of course, where are my manners?" I apologize. "I'm Tom Anderson, I'm here with Courtney Carmicheal."

Given the number of introductions I had given, it had gotten natural at this point.

"And who do I have the pleasure of talking to?" I returned the request.

"My name is Emilia Bell, I'm a reporter." She answered, "I'm here with Tim Walton."

My blood ran cold. Emilia Bell? A reporter? Like the woman who Parker had talked about? And I had just given her my name. Shit.

"That's your sister? Isn't she? What's her name?" Emilia asked. "She's a cute one for sure."

Well, if she had my name, and was here as a guest, she could just ask around and she'd find out Cindy's name easily enough. But why was she here?

"Cindy." I answered.

Emilia nodded, sipping at a glass of champagne. She looked at the still half-full glass, and shook her head. "You seem like an average Joe, this must seem crazy and extravagant to you."

I tilted my head in agreement, "You're not wrong. Never thought I'd be in a house like this, having food like this... the whole thing must have cost at least a couple grand, but they didn't even charge us for dinner." I marveled.

"You host, you pay." Emilia laughed. "That's how the rich live. But what goes around comes around, and eventually everyone who attends one of these is expected to throw one of their own. Though I suppose Mr. Carmichael will be the one throwing the parties for a bit, not you or Ms. Carmichael."

I winced. She had definitely nailed me down as Courtney's boyfriend. Shit. Shit, shit, shit.

Okay, so she knew my name, Cindy's name, and that we were here with the Carmichaels. That was it, right?

"You seem uncomfortable." Emilia noted. "More at home among the businessmen?"

"No." I assured her. "It's just... Courtney says I should avoid talking to paparazzi."

"Paparazzi?" Emilia laughed. "I'm wounded. Paparazzi would be the poor fellows outside with the cameras, not that they would be allowed outside an event like this. Do I look like that's the best I can manage to you?"

I glanced over at her, damn, she looked good. Which was probably how she landed an invite to an event like this. She was arm-candy for whoever brought her. She knew it and was exploiting it. She had already gotten my name, so why was she still here?

Fishing for leads, I realized.

"No. I just wasn't expecting reporters at dinner." I stated carefully.

"This isn't an interview, Mr. Anderson." She told me, teasingly. "Just a casual chat between acquaintances at a dinner party."

A casual chat with serious implications.

"But I can see I won't sway you, so I'll let you get back to the business elite, or perhaps to your girlfriend." Emilia smiled, and downed the rest of her champagne. "Enjoy the rest of your night."

I tried not to run, taking carefully casual, slow steps until I could drop into the seat next to Courtney. Heidi was still distracted with someone else, and Robert was off talking to a few older gentlemen.

"Emilia Bell is here." I whispered.

Courtney nearly spat out her drink, but recovered and gave me a look. I motioned with my head and she followed it to find the woman with a new glass, now seated next to who I guessed was this "Tim Walton" she was accompanying.

"Wonderful." Courtney breathed. "Did she-?"

"She knows my name, Cindy's and that we're here with you." I told her quietly.

"Well, it was bound to happen eventually." Courtney sighed. "The worst part is, we almost have to stay for another hour to be polite. Now, shoo. Go make some more connections. There are some powerful people here, good people to be on good terms with if we need help later."

I rose and wandered over to Robert.

"Ah, speak of the devil." Robert laughed, pulling me in with an arm around my shoulders. "This is the strapping lad now. Gentlemen, I give you the man who's winning over my little angel. This is Tom."

"Tom, nice to meet you." The taller fellow, with a simple head of gray/white hair, simple, classy glasses and a bit of a lanky build, standing about an inch taller than me.

The other man was about an inch shorter than me, with broader shoulders and a stockier build, though he was well past his prime. His suit was a little looser, giving him a warm grandpa look with his thinning white hair, bushy eyebrows and similar glasses.

"The pleasure is all mine." I returned the greeting. The men looked vaguely familiar, though I couldn't quite place them.

"So, what does the protege of the great Robert Carmicheal think of the coming trends in market finance?" The stockier man laughed.

"Well, I think tech is going to take an even bigger lead." I admitted. "Between improving robotics and AI there are going to be major shifts towards tech."

"You think AI will take over?" The taller man smirked.

"I wouldn't say take over, but revolutionize." I clarified. "I think people will always be needed, because there are some things that AI will never be better at, but I think AI will help make people far more efficient at what we already do."

The two chuckled.

"I very much agree." The tall man assured me.

"I do think we need to be careful." I continued. "I admit I'm not on the front lines, but I worry that between hallucinations and theft of Intellectual Property AI will start doing more damage than good. We need regulation to stop the theft, pollution of the internet and the misleading of people through hallucination, or people will never trust the technology."

"Not thrilled that you want to put the government on the job," The taller man admitted and the stocker man nodded his agreement. The taller man continued, "But I can see your point. Robert, I look forward to watching his career."

"Thanks, Tim." Robert grinned. "I think my Courtney chose pretty well."

"I'll be watching too." The stockier man nodded. "It's nice to see such promise in the youth."

"If you want to discuss how we might actually make meaningful strides... I'd be interested to hear your thoughts." The tall man told me, and handed me a card. "Call me, and my secretary will set something up. Just don't go giving out my number." He teased.

Robert and I shook hands with the two men and they walked away. I glanced at the card and saw the name: Tim Cook, Apple CEO. I nearly had a heart attack. I had blabbed and ran my mouth in front of Tim COOK? The man with him... my mind raced and I finally placed him. He was Warren Buffet!

"They seemed to like you." Robert chuckled.

"I just said all that... in front of Tim Cook and Warren Buffet." I whispered.

"You didn't recognize them?" Robert looked at me somewhat surprised.

"I wasn't expecting... They look different in person..." I tried to excuse myself.

"It's okay." Robert told me. "I think they like it when a young man gives them proper respect and has an open discussion with them, even not realizing who they are. No one likes being put on a pedestal. At least, not for long. It can be novel, but after a while you want to be treated like a person again."

Robert took me back and sat me at the table with Courtney, Heidi was nowhere to be seen.

"So, who all did you meet today?" Robert asked. "I'll see if there's anyone I think we should make sure you meet before the evening is done."

I tried to recall everyone I'd met, and glanced around the room.

Emilia Bell was watching me with an expression somewhere between smug, simmering, and tipsy jovialness. She was definitely enjoying the free bar, and a man I assumed was Tim Walton was sitting behind her talking to a provocatively dressed young lady.

"Sounds like you did well." Robert noted, sipping his brandy, which seemed to be his drink of choice. "We'll need to introduce you to a few more people as you attend more of these parties."

"How often do these parties happen?" I wondered.

Robert thought for a moment, "There's usually one every couple of weeks. Networking and socializing is critical in our circles."

"Is that why you were okay with me only having a business minor, instead of insisting I got an MBA?" I wondered.

Robert nodded. "Unless you are building your company from the ground up, you hire people to do most of the work that they teach you in college. It is important you have a basic understanding of business, and your minor should do that, but the most important things are who you know and who you are taking advice from."

Robert finished his glass of brandy. "You are building relationships now that will stay with you throughout your career. Don't take every piece of advice they give you, but certainly think about them. Weigh the pros and cons, listen to diverse opinions. If you follow the herd, you won't have anything but average results."

I nodded. I hadn't realized just how big this was.

I glanced around for Cindy. Where was she? There was Ken, and there was Landon. So where was...?

I finally found her, talking to a young man with wavy, dark brown hair, broad shoulders, and a well fitting vest. He was clearly a few years older than her, maybe even a year or two older than me, but he was clean cut and was talking to her intently. She seemed genuinely interested in whatever he was saying.

"Hey Courtney, who is that? The guy talking to Cindy?" I asked.

"Uh, I don't know." She admitted. "Dad, do you know who that is, talking to Cindy over there?"

Robert looked over, "I'm not sure. I haven't seen him at these parties."

I hoped Cindy knew what she was doing. Courtney was hoping Cindy could find a well-to-do husband so her new little sister would have a secure future. I mean, about anyone here was most likely a catch, but I wanted to make sure she was with someone good.

"If you're worried, why don't you go say hello?" Robert prodded.

I stood and started walking the edge of the room to where Cindy and her admirer were chatting, until I heard a voice I recognized.

"I think you'll find that I'm quite capable of making that happen now." I heard Heidi say.

"You think you could get Mr. Carmichael to make that kind of investment in our venture in Arizona? I swear, all indicators say that that is the next place those fleeing California are going to go. If we buy up land now, we can make a killer return when demand skyrockets." A man urged in excitement.

"Oh, I think you'll find I have quite the sway with him." Heidi assured the man. "Just wait until I get him to tie the knot, I'll have him wrapped around my finger."

I was seriously disappointed in her. I had been growing to like her, but if she was just trying to capture a pawn, she wasn't for Robert. I'd have to tell Courtney and Robert when I got back.

"Oh, Tom! Tom!" Cindy waved me over as I got closer.

"This is the brother you were talking about?" The man noted, looking me up and down before rising and extending a hand. "It's a pleasure to meet you. It's been hard to get Cindy to talk about anything other than you. Nice to put a face to the legend."

"The pleasure is mine." I told him. "And I don't know if I'm all that."

"This is Scott." Cindy told me. "He helps run a charitable organization helping try to deal with educational disparities in Africa."

"That's one of the organizations I am involved in." He waved the praise away humbly. "It would be terribly selfish of me to not attempt to help those far less fortunate."

"Is that what you were talking about when I came over?" I wondered.

"No, we were actually discussing what we want to do after the pandemic shutdown is over." Cindy admitted.

I blinked. I'd forgotten that we were still in lockdown. Wearing masks out and about at this point had just been so natural I hadn't even thought about it. Though, glancing around, none of the people here were wearing them. Heck, thinking about it, that might be how they had managed to convince the paparazzi to stay away. The tables were all six feet apart, not that that felt weird in this grand ballroom, but the servers weren't wearing masks.

"Remember the pandemic we're in the middle of?" Scott chuckled. "Everyone here can afford treatment if they catch it, and don't want to be reminded of anything remotely related to it, so I can see how you forgot."

I looked around and tried not to shake my head. "I admit, I'm isolating with friends, so I forget it is a thing."

"You're lucky." Scott told me, leaning back. "I find myself incredibly inconvenienced. I don't like living the 'rules for thee but not for me', life that many of our peers here embody."

"But you're still here?" I noted. "And you aren't wearing a mask either."

Scott sighed. "Family obligations. My mother has been pushing me to attend more of these, and as much as I hate it, she has a point. If I'm going to accomplish anything, I can't just sit back and try and do everything myself. I've been avoiding these 'song-and-dance' messes for years, it just so happens that when I actually need the help... it's during a bloody pandemic."

I watched Cindy's face. It might be nothing, but...

"Well, I'm glad you're here." I told him, "I hope to see you at the next one we attend."

"I hope I can come too!" Cindy declared.

Scott smiled, a sincere smile. "I think I will make the effort... Oh, damnit. Mom's waving me over."

He rose, "If you would excuse me."

I saw him stiffen as he walked across the room to a woman in a yellow dress. A gaggle of women shooting jealous looks at Cindy were gathered around the woman. I got the feeling mom wasn't bringing him here to help him with his business endeavors. She looked like the type that had "give me grandbabies" practically tattooed on her forehead.

"He seems nice." I noted.

"Yeah... I hate to say it, but Ken and Landon, they were nice to start with, but once they relaxed... I don't think I could date a person who talks about construction workers, like Dad, the way that Landon does. And I don't think Ken realized he was being so condescending, but..." Cindy sighed.

"At least Scott turned out to have potential." I noted.

"He does," Cindy agreed. "He definitely does."

"So long as he feels the same." I observed, as I watched him politely greeting all these rich young women.

We arrived back at the Carmichael table to a raised brow from Robert.

"That young man, his name wasn't Scott, was it?" Robert wondered.

"It was. Why?" Cindy asked.

"It wasn't until he crossed over to the Strong family table that I realized who he is." Robert nodded thoughtfully. "If he is interested in you, you are a lucky young lady."

"Why? Who is he?" Cindy pressed.

"Well, based on the rumors, I think he'd prefer you didn't know." Robert apologized. "He'll tell you when the time comes. I hear he's a good young man and I'd hate to be the wedge that comes between you."

Cindy pouted.

I remembered the conversation I'd overheard on the way over. "Speaking of hating to be a wedge between people..."

"If you are referring to Heidi," Robert sighed, "Courtney already has told me she doesn't approve."

"Well, add to that I just heard her saying she could control who you invested in and who you didn't and once the two of you were married... What was the phrase she used? She'd have you 'wrapped around her finger'. So, hate to say it, but I'm with Courtney on this."

Robert sighed, "You would think she'd at least pretend for longer. Brooke certainly did."

"We'll find you someone." I assured him. "Don't lose hope so easily."

"Well, let me collect her." Robert grumbled. "I'm in no mood to entertain."

He made a motion and a man in a black suit, that was clearly his security, seemed to materialize.

"Since I'm leaving, you two can as well." Robert declared. "I'll try and put something together in a few weeks to make it up to people that I'm leaving so early."

"Should I inform your escort?" The man asked.

"Do that." I instructed, and we stood.

Robert was cordial to Heidi, but I think the looks on everyone's face when we walked over said that Heidi was still trying to peddle his influence, and they were worried he overheard.

We linked up with the security team and our cars and Robert's vehicles were waiting when we got outside.

"Take care, Sunshine." Robert bid Courtney farewell, kissing her on the cheek.

We got in the cars and began the long drive back.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Emilia was feeling very drunk, and very pleased with herself as she rode the elevator up to the apartment her team shared. She had got enough info that she was sure Nate would have that sucker nailed to the wall by noon tomorrow.

Which means, if she didn't want the opportunity to go to waste... she was finally gonna get laid tonight! Might be why she got so smashed.

She struggled to unlock the door and staggered into the apartment. She glanced down the hall their rooms were in. Both potential lovers had lights on under their doors...

Did she pick Nathan, get fucked by his dick and watch Trish squirm for a year... or did she take Trish, probably get eaten out, get a strap-on that wouldn't go soft on her, and watch Nathan eat humble pie for a year? Honestly, it was a toss-up for her at this point. She'd figured out she probably qualified as "bisexual" a while ago, though this would be the time to prove it.

She grinned, her decision made, and tried to saunter to her chosen lover's door. She didn't bother knocking.

"Hey there." She smirked, not even hearing the slur in her voice. "Got the jackpot. I found out his name, and his sister's name, plus his hometown." She told her chosen lover.

"Let's fucking go!" Her chosen partner celebrated. "We'll have that story in no time flat."

"But before we do..." Emilia smirked, strutting/stumbling across the room, "You have a bet you need to win, don't you."

Her partner swallowed. "You... you know about that?"

Emilia smirked. "Seeing how much work it was to get you two to set it up, I'd better know."

"So, you're okay with it?" Her prey stammered.

"If I wasn't would I do this?" Emilia demanded, slipping her arms out of the straps on her dress and letting it fall to the floor, leaving her fit, lean body clad only in the nearly transparent black thong she'd worn under the dress and her heels.

She leaned forward and kissed her chosen winner, her lips seemed to melt into theirs. She was feeling herself, confident and sexy. This was the one place she was confident in, she had been practicing kissing since she was old enough to do so, using it to lead people on, excite them and it had worked most excellently in her favor, she was confident in her kissing skills.

Her partner was clearly in agreement that her kissing was amazing because it took them a full minute before their hands reached up and gently began to fondle her breasts. It was a new sensation for Emilia, allowing someone she was actually okay with to touch her boobs. Sure, she'd been fondled on the street a time or two, but that had never been enjoyable, and had frequently resulted in a broken nose for those who she'd been able to identify as her assaulter. This however, was far more enjoyable. Their hands squeezing and molding her supple mounds felt... exhilarating, electric... and then they starting pinching her nipples and FUCK they could keep doing that.

She pushed them on the bed and pulled their shirt off, pulling them close and feeling their chest press against hers. To her delight, her breasts responded nearly as delightfully, pressing them against her lover's bare skin, as they did in their hands. She mashed her highly responsive breasts against them and resumed kissing.

Her lover was excited, beyond excited, and she could feel it in their trembling hands as they hooked the elastic band on her thong and pulled them down her shapely thighs. Emilia relished the feeling, excited for what was to come, until she kicked her thong to the side and off the bed. Now, it was her turn, and she removed her lover's pants and underwear, bringing their sex into view.

 

She'd always admired both genital options, and had seen far more vaginas in her time than cocks. She had to admit, her lover's genitals were an admirable credit to their gender. She began to stroke her lover, enjoying the powerful feeling of their sex in her hand as her lover trembled in excitement.

"Now, we can't forget something important down here." She slurred.

"Oh, right." They replied, snapping out of their reverie and retrieving an important piece of equipment from their bedside table, and situating it properly over their own sex.

"Perfect." Emilia sighed, gazing at the rod that would be her first venture into the world of sex. "I'm ready if you are."

She laid down and her lover climbed between her legs. Emilia sat up, watching the rubbery feeling tip as it slipped up and down between her folds. There was a thrill each time it reached the top of her slit and ground against her clitoris, but good as that felt, Emilia was dying to know what it felt like inside her.

Being around all those rich bastards and their expensive whores, or wives if you wanted to call them that, had made her horny. She knew infidelity was rampant among the wealthy, and she had spent nearly half the night wondering how many of these men had fucked how many of these wives. Knowing she planned on going home to get fucked had only made it worse.

Now the moment was here, and she was dying in anticipation.

Her lover finally lined up their rod with her hole... and pushed.

The sting of her sex stretching, and the pressure turned into a flash of burning pain as the hymen she was shocked had survived so long popped, was nothing. It felt so damn good! The stinging and pain could have been twice, no three times, as bad and she wouldn't have cared. Her lover plunged the slick rubbery surface deep into her and Emilia swooned.

Why the fuck had she waited so long?!

Her lover began to pump, and she was almost surprised it could feel better... but better it was, and continually so. Emilia clamped her legs around their hips, encouraging them to go faster and harder.

"Oh FUCK! YES!" She screamed. "FUCK!"

Emilia grinned, even more turned on knowing the loser across the hall definitely heard that. If she knew her team members as well as she thought, any second now...

The door opened and a pair of wide, terrified eyes peaked in.

Emilia squealed in delight, throwing her legs wide in the air making it clear what was happening.

"Don't stop!" Emilia ordered. "Don't you dare stop!"

"Fuck!" Nathan grunted, slamming his condom sheathed cock into her faster and faster, as Trish gasped from the doorway. "I'm gonna-"

"That's what the condom's for!" Emilia screamed. "Cum in me!"

Nathan's cock was pulsing as it violated her virgin depths repeatedly, feeling like it was a hand dragging across the keyboard of the nerves inside her pussy. Pages of incoherent pleasure filling her brain, until...

Her body felt like a spring being released, her legs flailed and her arms clamped down, pulling Nathan to her and Emilia screamed in pleasure. She was orgasming! Holy hell it was amazing! Nathan wasn't stopping either, he pumped hard and fast, then while her body was still going nuts, he slammed into her and she felt him pulse and there was the rush of his cum filling the condom inside her.

Part of her lamented that she'd had him wear a condom, but she was drunk, not stupid. He was a coworker, and now a fuckbuddy... Maybe she'd give him a chance and see if he was as good of a boyfriend as he was a hacker, and now lover, but either way... it had been time. Just not time to get pregnant.

When her brain finished rebooting, she glanced at the door. Trish was gone, but the door was ajar. Trish had seen herself losing the bet live, and she couldn't deny it.

Emilia leaned back and smiled. If Trish thought losing the bet made her the sole fucktoy of the man flopped on the bed next to her, she was out of her mind. Nathan would just be easier to control and use to turn them both into her personal fucktoys. It was the real reason she'd given it to Nathan. He'd be wrapped around her finger, and Trish would be too honor bound to object. If she'd given it to Trish, the woman would have felt like she owned them both, and Emilia was not about to be someone else's toy.

Fuck, this was going to be a good year.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Elaina pulled the limo up to the Carmichael estate, and we were able to get out without worry. It was well past dark, and there would be no angles for anyone from the gate if anyone had been there.

"Thanks for the fun evening." Cindy thanked us. "I hope it isn't too disappointing that I didn't like Ken or Landon."

"Silly, they were options." Courtney told her. "Never know if you don't try."

"And it's not like the night was a waste." I told her. "I met lots of important people, and you met Scott."

Cindy blushed a little, "I hope I get to see him again soon. He seemed really nice."

We just laughed and headed toward our rooms.

"Now, I think there's someone who'll be waiting for you in your room, love." Courtney told me. "Give her a good time, will you?"

"I always try to." I told Courtney.

"It helps keep everyone working together when we're all happy." Courtney pointed out.

"I'll try and add another happy customer to the list." I assured her.

Walking to my room, I carefully cracked the door and saw Bristol sitting on my bed. Her rich brown hair tumbled down her back and covered the strap to the sexy white lingerie bra she was wearing. Sitting staring at the wall, she looked almost like she had been waiting, longing, all day. The thin string of the white g-string she was wearing sat high on her hips, practically at her waist, and her long, flawless legs shimmered in the dim light in the room as she leaned on one bent leg, the other extended across the bed.

"You look beautiful." I told her as I quietly closed the door behind me.

"OH! You're here!" She jumped.

"You seemed almost sad." I noted. "Is something wrong? You know you don't have to do this if you don't want to."

"Oh, I want to. It isn't that." She protested a touch shyly. "But..."

I sat on the bed and waited for her to figure out what she wanted to say. I could see she was trying to find a way to put it into words.

"... I just... don't know how to be special for you." She finally managed.

"I don't understand." I admitted. "What do you mean?"

"Well, the girls, we've all been talking." Bristol explained. "You have like twenty of us that are all..."

"... that are having sex with me." I supplied.

"Yeah... that." Bristol accepted. "But no one wants to just be 'another girl' to you."

I gave her space to process and tried to really listen. Sarah said it meant a lot to women when you let them speak and actually listened, so I was trying to be more and more conscious in my efforts to listen.

"But... how are we supposed to be special when there are twenty girls doing their best to make you happy?" Bristol sighed. "Amy gave you her ass, Nikki said she's gonna make sure you always wake with a pair of lips around your cock, and Elaina says she'll let you flaunt her as you fuck her in front of anyone you want..."

She hugged her knees close to her chest. "I'm terrified of you sticking... God, the girls say it is so thick..."

"You don't have to do anal if you don't want to." I assured her.

She nodded. "I know, you have said that we never have to do anything we don't want to. I appreciate it. But that leaves me in a bind. I don't know if I can be better than Nikki about sucking you off, and I have duties in the morning, so I can't be one to wake you that way. And I don't think I want anyone really watching. I thought for a while I could, but..."

"Totally fine." I told her.

"But then... what do I bring that you don't already have?" Bristol demanded. "What value do I bring to you?"

Bristol moved her knees and cupped a lace covered breast in her hand. "I don't have huge tits like some of the other girls, and I don't even have the big ass American men really like."

Seeing her fondle herself made me twitch, and I had a thought.

"Well, who are you here for?" I asked her.

"What do you mean?" Bristol asked.

"Are you here because you want to do it?" I fished. "Because you know I want you? Or are you here because you want other people to know we're having sex?"

"Well... I suppose I'm here because I want it... and I want you to want it, but that's the problem, isn't it?" Bristol asked.

"Well, let's see." I declared, and I stood, stripping off my pants. Bristol's eyes grew wide as she was presented with a definitely erect appendage. "That looks one hell of a lot like I want you, doesn't it?"

Bristol swallowed, then nodded.

"You told me you don't want to do anal. Doesn't look like that matters." I told her. "You said you don't want people watching, that doesn't look like that matters. You may not be the one who gives the best blowjobs. Doesn't look like that matters."

Bristol just stared at my cock.

"I want you." I told her. "I want all of my girls, and I don't care if you don't think you have something 'special' to offer. Each and every one of you is 'special'. I think I've been with enough girls at this point to tell you that you don't have to be crazy, kinky, or talented for me to enjoy being with you. You are all gorgeous and I want you. You think you bring nothing different to the table? Well, let me tell you this, you aren't just another girl carbon copied from everyone else with slightly different colors from the printer."

Bristol's eyes left my cock and we locked eyes.

"You are a wonderful, and amazing individual. I can't believe I get to be the one here that you have chosen, and I can't wait to get to know you better." I told her.

Tears formed in her eyes and I stepped forward and wrapped my arms around her. The emotions rushed through her and she clung to me as well. She buried her face in my shirt and cried.

I let her cry, until it started to subside, then I reached down and gently tilted her chin up. I kissed her softly, and she kissed me back. I allowed my hands to roam her back, and she shivered at my touch. Her skin was soft under my hands, and I began to massage and caress her back.

I felt Bristol begin to move and realized she was undoing the buttons on my shirt. Once she had my shirt open, she slipped it off my shoulders and began to run her hands over my chest. I had to admit, I was proud of my physique at this point. Tina had helped me get a toned and sculpted body, and Bristol's hands trembled as she felt the muscle of my chest and shoulders.

I unclasped her bra, and Bristol let me take it off her. I eased her back until she was laying on the bed. She sighed as my hands explored her breasts. She was clay in my hands, willingly allowing me full access to her body. I continued to kiss her as I savored the soft, elasticity of her boobs in my hands. She made pleased noises into our kiss, seeming to enjoy my hands squeezing and kneading her tits, as her arms fell to the bed forgotten.

I moved down and began to suck on her nipples and lick the flawless mounds of her breasts. Bristol just closed her eyes and let her breathing and the sounds of her enjoyment and encouragement urge me on. I took my time. What can I say? I love boobs. They feel so good in my hands, in my mouth, and pressed against me. Bristol certainly wasn't complaining about me enjoying the assets God had given her.

Eventually, the smell and the way Bristol's hips started to fidget drew my attention south, and my cock was begging for its turn. I released one of her breasts, freeing a hand, and attacking her nipple with my mouth. My now free hand began working her panties down her thighs. Bristol lifted her butt to allow me to strip her completely naked, and her moans trembled in excitement. As the g-string came off her ankles, she spread her legs, an open invite that I was only too happy to accept.

My fingers crept between her legs, massaging the insides of her quivering thighs before I allowed my fingers to traverse her slit, from end to clit. She was soaked. The slickness was begging for me to take her, claim her, and make her mine. Her voice rose an octave as I began to swirl two fingers on her clitoris, and I could tell she was wound tight as a harp. My thumb stroked her folds like a musician as my fingers kept up my stimulation of her pleasure button. Her voice grew strained, until with a pleasured cry, she shook like a bow that had just released.

Her legs clamped around my arm, and I began simply stroking her folds. Enough to tease, but it wasn't enough to try and push her toward another orgasm. All the things that would push her forward would be like a cattle-prod, though I'd be shooting jolts of overwhelming pleasure instead of electrical voltage.

Her orgasm lasted for what seemed like an eternity, but at last, her legs relaxed, releasing their deathgrip on my arm.

"Please... I need it." Bristol gasped. "I've never felt this way before..."

I just kissed her and slipped between her once more widespread legs. Bristol rose to watch as I took my throbbing dick and ran it along her folds to coat it with that amazing lubricant. She put her feet on my hips to get a better angle as I found her opening and pressed.

"Oh bloody...." She muttered, eyes squinting as she felt her body accept my manhood. "... hells, that's a... It feels good though."

Her hymen caught my head like a net.

"Ready?"

"Do it."

A quick thrust and it was done. Bristol put a hand on my chest as I felt the burning heat of her body's reaction to giving up her virginity and the resulting blood. She held me for a minute, two inches into her, until she was ready. With a nod, she dropped her hand and laid back to savor the experience. Her vagina slowly swallowed inch after inch as I fed it into her with each thrust, feeling her body open to accept me.

"Fucking hell." Bristol breathed. "That's so fucking good."

"Likewise." I groaned.

The silken sheath of her body seemed to suckle on my length as I began slowly making love to her. She was tight, but even tight as she was, she was slicker than she was tight. Each thrust was like a symphony of the bumps and veins of my cock singing against the ridges and folds inside her vagina. I slowly got faster, and faster, and Bristol moaned louder, and higher. Soon I was pumping in and out of her like a jackhammer, and the sound of our bodies colliding was the percussion to the aria of her pleasure.

Her song cut off as she came, and came hard. Her legs clamped on my sides and the tightness of her pussy clamped like a vice around my cock. I groaned, and thrust three more times before pushing deep into her and exploding.

I was seeing spots, her pussy felt so good. Each spurt caused her to tighten, then release, then tighten again as her body was flooded with my cum. Bristol's feet finally slipped from my thighs and she wrapped her legs around me, pulling me deeper as I shot my last two streams into her womb.

She trembled from the pleasure, the sensations, the orgasms, as she held me close and deep inside her. I just responded in kind, wrapping my arms around her, holding her close and smelling the strawberry shampoo in her hair.

We held each other for a few minutes, until at last Bristol released me, and I pulled my softened length from the warm, wet embrace of her body.

"Was I good?" She asked as I laid down by her side and pulled her to me again. Her voice pleaded for reassurance.

"You were wonderful." I assured her. "Didn't you feel how hard you made me cum?"

"I didn't exactly have anything to compare it to." She admitted.

"You got seven shots of cum from me." I told her. "If I hadn't been enjoying it, you might have only gotten three."

"I'll take that." She sighed contently.

"You want a picture to add to the harem archive?" I asked.

"I've heard about that." Bristol admitted. "Pictures of everyone's pussy after you fucked them the first time..."

"If you don't want to-" I began.

"Do you want it?" She cut me off.

"Uh." I fumbled.

"Do you want a picture of this?" She asked, spreading her legs to look down at her pussy leaking blood and cum.

"I admit, I think the pictures are sexy as hell." I conceded. "I look at them sometimes when I struggle to believe this is all real."

"Then... okay, take the picture." She told me.

I lined up the shot the way Taylor had taught me and got a few shots. One was blurry, but the others turned out great.

"Thanks." I smiled, and kissed her.

"A little something special from me." She smiled.

"Very special." I assured her.

I put my phone away and pulled the sheets and blankets up over us. I clapped and the lights went off.

Another day in paradise, come to a close. Another member added to the harem.

The following days had who knows what madness to come, especially because now the Triad knew who I was. I had no idea what they could find on me, what they might make up, but right now, I didn't care.

I was holding my new lover, and surrounded by more lovers than I had a right to even dream about having. I had wealth, luxury and privilege I would never have dreamed of just a few short years ago. Even if I lost half of everything I had, I'd still be living in paradise.

Who knows what tomorrow would bring? I'd just have to keep going.

And, I still had eight more girls to induct into my harem, and that was just the girls that had joined us here during our vacation. I understood there were more who would be joining up when we returned home for my last year of college.

My cock twitched at the thought. I was far from done, and even then... I hadn't even started thinking about babies yet. That was exciting and terrifying in its own right. But looking at Bristol, and thinking of all my harem members... I was content. I'd give them as many children as they wanted. They said it takes a village to raise a child. Well, my children would have a village.

But that was down the road. So, with that in mind, I held the softness of Bristol close and drifted off to sleep.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

To be continued in Chapter 33...

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