Too Good To Be True Ch. 27

I drew myself out and Cindy got her face down by Courtney's snatch. Courtney pushed out my sperm and Cindy took two fingers and scooped up a glob and plunked it into her mouth. I saw her swirl it around her mouth, pondering the taste. She swallowed and slowly scooped the entire load leaking out of Courtney's cunt into her mouth.

"It's weird. Isn't it?" She asked Courtney, "It's, like, really fishy, but also sweet and salty."

"That's probably because of dinner. What he eats makes his cum taste different, and some things affect it more than others," Courtney explained.

"Have you experimented to see what makes him taste the best?" Cindy wondered.

"No! We should do that!" Courtney giggled. "Now, you wanted to watch his dick fuck my ass while you broke in your dildo."

"Yeah, let me turn off my plug, pull it out, and prep my dildo," Cindy agreed happily, she leaned back, held the button to turn off the butt plug and slowly pulled the bulge out of her stretching rectum. She set it on a washcloth on her bedside table, then grabbed the dildo and lubed it up.

While she was doing this, Courtney started sucking my cock to get me erect again for her ass. The sucking and the show my sister was putting on got me Rock solid again. Then Courtney started lubing my cock with the lube for her ass.

"Ready!" Cindy proclaimed, leaning back and putting the dildo at the entrance of her ass.

I put my dick against Courtney's puckered anus, then slowly pushed slowly in. As Courtney's ass spread to swallow my cock, Cindy pressed the dildo into her own pucker and shuddered as her ass surrendered to the silicone invader. The further I pressed into Courtney, the more Cindy pressed her dildo into her anal cavity. It wasn't inch for inch, but Cindy aimed to bottom out her dildo when my cock bottomed out in Courtney.

"Oh, fuck... fucking hell," Cindy moaned.

Once I was completely inside Courtney, I started thrusting, with Cindy matching my tempo. I drove Cindy quickly to her first anal orgasm, which broke the sync because Cindy's arms just stopped as she arched her back and she groaned.

Courtney took longer to reach her orgasm, and when she did Cindy reached her second. Courtney took my hand and guided it to the handle of the dildo in my sister's ass. I couldn't resist and took over, plowing my sister's ass with the silicone fake as my real cock plowed Courtney's ass.

I knew it wouldn't be long until Cindy couldn't take more, I was determined to give her as much pleasure as I could before that happened. I worked both girls' anuses with vigor and purpose. So focused was I on causing pleasure that once Cindy's back arched she never stopped, and she was moaning gutturally.

"I think she's out," Courtney finally told me.

I leaned over and saw that Cindy's eyes were rolled back in her head and she was drooling.

I pulled the dildo out of her, which caused her to relax like a deflating balloon. Cindy continued to groan and moan until finally her eyes fluttered and she gasped, "Fuck... bro, that was amazing."

Cindy's limbs flopped as she tried to move, "I can't feel, like anything."

"I hope I didn't wreck your ass..." I apologized. "If I did, I could go get you numbing gel for it."

"Oh, I think it'll be sore, but it still feels great," Cindy assured me.

It took several minutes for Cindy to normalize, then we cleaned up got ready for my parents to get back, which they did a half hour later.

Cindy and Courtney were back in Cindy's room, and I was in the front room channel surfing when they walked in. My dad headed back to one of the other rooms and my mom sat in one of the armchairs.

"Well, that was nice, but tiring. And we have hardly talked, how are you?" Mom asked and Courtney and Cindy came out to join us as I assured my mother I was doing well.

"You said you, um, moved in with Courtney, is it still that same address you gave me before?" Mom asked.

"Actually, no. Courtney was worried some of her friends were struggling with housing issues, so she worked with her dad and they bought a mansion a few miles from campus and started like an unofficial sorority there. We've filled less than half the rooms, and it's great. I'm picking up a business minor at the behest of Courtney's father, and several of the girls are business majors so they help me study," I explained.

"Oh, that's wonderful," Mom congratulated me. "Since it's Courtney and your house though, who gets to decide who can live there?"

"Well, Tom and I kind of have the final say on that. We generally let everyone living there vote, but it is Tom's and my house," Courtney informed her.

"That's wonderful, it is a great reassurance to me. You see, Cindy, tell them the news!" My mom pressed.

"I got accepted! Starting this fall, we'll go to the same school! I'm hoping to move out there in the summer to work out a job and everything before school starts!" Cindy proclaimed.

I felt a weight in the pit of my stomach.

"That's great!" Courtney exclaimed, "I'm sure you can stay with us! We have plenty of rooms."

This was starting to feel like a setup. I couldn't say no, not to my mom like this. I'd walked right into a trap.

"Yeah, she should be able to stay with us," I conceded.

"And Mary got accepted too, do you think she could live with us as well?" Cindy asked.

"I'm sure we can work that out," I surrendered.

Courtney texted the harem, and while there were grumbles about losing nude living privileges, but people understood.

"Yep, you two can live with us!" Courtney confirmed.

"I'll go tell Mary, she'll be so excited! Could we move out with you guys when you fly home? Flying private is like the only way to fly right now, so otherwise we'd have to drive..." Cindy begged, "And both of us want to move out as soon as possible."

I began to feel dread, this had the markings of a disaster.

"And I was planning on taking everyone to our New Jersey summer house for a month, it has a private beach and everything!" Courtney squealed excitedly.

"Oh, my gosh! That sounds amazing!" Cindy giggled excitedly, "I have to go tell Mary!"

We watched TV for a while, until my mom left to go take care of a chore.

"What are you doing?" I asked Courtney once I knew my mom was to far away to hear.

"What do you mean?" Courtney replied a little too innocently.

"There's no way Cindy pulled that off by herself. And mom doesn't just set things up like that. What are you up to?"

"Okay, Tom. I know you have reservations, but incest is even more of a societal construct than monogamy. Hell, it's even legal in New Jersey and Rhode Island, between two consenting adults. So long as we have proof that you two had sex in New Jersey, and they can't prove that incest took place at the harem house, Khloe says it would get thrown out in court," Courtney explained. "I know, she's your sister and you don't like the idea. But a few of the girls have started grumbling that they're the only ones having to face societal displeasure if anything comes out. The girls and I already chatted, and Cindy knows about the harem and wants to join, and if you refuse... it honestly might be the end of the harem. You can't expect the girls to shift their societal expectations to join a harem but never accept shifting your own expectations. We can work Mary in, Sarah is sure that she can work that out."

"How long has this been a thing in the works?" I asked uncomfortably.

"Taylor has been struggling since she joined the harem, and when she learned about Cindy, well she and a few other girls decided it would be a perfect test of your resolve," Courtney apologized. "Sarah and I have been trying to avoid it, and it was agreed if Cindy didn't come to our school, then it would drop, because it would be against harem rules for you to have sex with someone outside of the harem, and I didn't tell Cindy about the harem until last night when she told me she was coming to our school."

I couldn't believe what was going on. But the more I thought about it, the more it made sense. A dude sleeping with a dozen girls wasn't a real sacrifice, while sharing a man was a sacrifice for the girls. I mean, Cindy was attractive, but she was my sister for crying out loud. At least my mom was out of bounds for the harem, sheesh.

"Alright, I'll do it. But only if we can get the proof in New Jersey first, I don't want to go to jail because my sister couldn't find a boyfriend and some of the girls wanted to test my resolve," I conceded.

"Deal, that was what we agreed on," Courtney concurred.

That's how four days later, I ended up getting on our private plane with Courtney, Cindy and Mary, with all of our luggage.

Once we were airborne, Mary turned to me, "Is it true you have a harem of girls you're having sex with?" She demanded.

"Um... yeah. It isn't a forced thing, everyone joins willingly, and all current members must approve new members. New members must be virgins and STD free, with a test to show it, and you have to promise to be loyal to the harem, and leave if you decide to pursue another guy," I replied awkwardly, I'd known Mary since she was four, so this was a touch awkward.

"What are the rules about having babies?" Mary demanded.

"Well, both me and the girl wanting to have a baby would have to agree on it, and I don't want to be fathering children before I'm out of college. But Courtney and I have talked about it, and we'd be fine with it. We'd put my name on the birth certificate and set up a trust fund for Child support and for the kid once they become of age once we were sure the child is being born," I told her, "So until me and the mother are graduated, I have to insist my girls are on birth control or we don't have vaginal sex."

Mary seemed grumped. "Damn it. I wanted in now. That means I have to wait at least a week to get on birth control and who knows how long to get tested," She glared at Courtney, "Then I'll show you what a really devoted girl, one worthy of being your wife, will do for you."

"Hold on there," I told her, "Courtney is my girlfriend, and she's the one I'm marrying. If you have issues with her, we're gonna have to work those out before we even consider you for the harem."

"Thanks, Tom, but I think me and Sarah can handle this once we arrive," Courtney assured me.

Mary ignored her, "Cindy says you have the best dick ever! Can I see it?"

"Not until you've worked things out with Courtney and joined the harem," I was taking a hard line with her, I didn't want her causing problems in the harem.

The flight continued roughly the same, Mary trying to convince me to make an exception for her, and me and Courtney, and eventually Cindy, telling her no.

"Honestly, Mary, you're being a bit of a needy bitch," Cindy finally told her. "You're not gonna win Tom over this way, and you're honestly probably just gonna get kicked out of the house and have to find your own place, during the pandemic."

That shut her up, but she did flash her panties at me once when she could do it without the other girls seeing. Honestly, that didn't help her case either, as they where heart covered granny panties. With the amount of lingerie I'd seen, it just made me wonder if she was mature enough to be having sex.

Dana picked us up in the limo and we had plenty of space for us and the luggage. We'd had to get a stretch limo, as the safe limit of passengers in the normal limo was 12, and that was packing us in tight. Dana had let it slide for a while with lap riders and such, but finally she had insisted. The new stretch could hold up to 25 people, and I hoped our harem never got that big. But for just us, the normal limo was fine.

Once we got inside, a few staff members took Cindy's and Mary's bags to their rooms and Sarah invited the girls into her office. Courtney had gotten a few staff members from her father's retainers. She had hand picked them and they were all girls that were honestly on board with the harem. They didn't want to join, which was good, because I didn't want any of our employees feeling like their jobs depended on having sex with me, but they were fine blatantly seeing harem activities. Seeing Debbie walking around nude didn't bother them, nor did me fucking the girls wherever and whenever I pleased. One of the girls had even cleaned around us as I fucked Tamora in her maid outfit one day, only giving me a wink to acknowledge the moaning girl with my dick buried in her pussy.

I'd asked her about it later, and she admitted she was a lesbian and while she wasn't attracted to me, she wondered if it was just her lack of good interactions with men, so she was using me to get used to the idea of men and penises. Most of the other girls on staff were less social and were slowly befriending the harem girls they were being paid to serve. A few were nervous virgins who appreciated the idea of getting used to sex being around them before they found a man, but the polyamorous nature of the harem was not what they wanted.

Sarah interviewed our new residents. Mary first with Courtney in the room, then Cindy alone. After the meetings with Sarah, the whole harem gathered with the new girls.

"Okay, so Cindy is happy to join the harem, and with Khloe's legal counsel that should be fine. We knew about that, and everyone is okay with it. Correct?" Sarah affirmed and everyone nodded. "Mary... honestly she worries me," Mary's face fell. "I propose a probationary period of one month for her to prove she can coexist peacefully with the other members before she is allowed full entrance to the harem and the associated privileges with Tom." Mary had made a little bit of a stink when she got here and all the girls agreed to the probationary period.

"A month?!" Mary moaned, "I have to wait a month?"

"A month IF YOU'RE GOOD," Sarah emphasized. "If you can prove you can meld with the harem faster, we can always adjust, but we are being generous. We know you have feelings for Tom, so we are giving you consideration when normally I wouldn't have even told you about the harem." She glanced at Cindy, who shrunk in her chair. "If you can't prove you can peacefully coexist in the harem with ALL current members in a month, you'll be given until the semester starts to find new living arrangements."

"But-" Mary started, but Brittany cut her off.

"No 'buts' there is a vaccine being distributed, so the pandemic shouldn't last much longer. You'll be able to find housing. We're being more than reasonable," Brittany explained.

"Do you accept our decision? You could just choose to live elsewhere," Courtney demanded.

Mary struggled for a moment, then slumped. "Yeah, I'll accept it."

Courtney smiled, "I'm hoping you'll learn to get along with everyone and we can all live together happily. One month isn't too long. Most of us waited two years after graduation before getting together with Tom."

Mary sulked for a minute, "So what CAN I do with Tom while I'm on probation?"

"Well, we all generally eat together, but Tom often takes girls out to dinners, or lunches in the park. You can go on dates with him. We are all welcome to wear as much or little as we want, so I suppose you could walk around naked if you wanted to, Debbie does. And you can watch him have sex with the other girls, maybe get ideas for what to do with him once you get through probation," Courtney told Mary, "And you are welcome to come with all of us to my family's summer house in New Jersey. There is a private beach, pools, tennis, bowling, and a gym all without living on the property. Our beach is a private cove and there will probably be lots of nudity and sex."

Mary was devastated, "And I just have to sit there and watch?"

"We can go back once you are off probation. We were only going for two weeks, with Brittany will be flying out every Thursday night and flying back every Sunday, so she can work her shifts at her clinic," Courtney explained, "You are welcome to head back with her anytime she's coming back, or come out with her later if you want."

Brittany shrugged, "Work is work."

"No, I want to be there," Mary assured everyone, "How can I... prove myself... if I'm not there?"

"Okay. Oh, one other thing. Everyone needs to be nice to the staff. Especially you, Ali," Courtney informed the girls.

"Why single me out?" Ali whined.

"Because I haven't had the staff complaining about anyone else calling the staff their 'bitches' and pushing them around," Courtney retorted sharply. "Of all the girls in the harem, you'd be the one I'd feel least bad about keeping in the harem, but making you live elsewhere."

"Fair enough," Ali conceded, "I'll treat them nicer."

"Why's that?" Mary asked, confused. "Why wouldn't Courtney feel bad kicking Ali out?"

Sarah smiled, "Ali's family is almost as rich as Courtney's. And while Ali has been cut off by her family and no longer receives an allowance like Courtney, she does have access to her trust fund. So both of them are fine financially. The housing was to help with socializing, accessing Tom for harem privileges, and helping, financially, the members of the harem less financially fortunate."

Mary's eyes widened, "You're both how rich?"

Ali shrugged, "I think I have like two hundred million dollars in my trust fund."

I smiled, when Courtney and I had finally checked on her trust fund it turns out her estimate of $100-$150 million dollars had been off. She had just over $550 million in her trust fund.

Mary seemed to relapse into herself and I could tell she was thinking hard.

Discussion continued and it was settled everyone but Brittany would head out the following day, on Monday.

"Now, since everyone here is at least a probationary member of the harem, and everyone knows about it... can we go back to relaxed harem rules?" Debbie prodded.

"Yes, clothes are optional," Courtney laughed and Debbie shed everything and Tamora ran off to wear one of her skimpy outfits. She still favored the slutty french maid, but she also liked a few outfits like her slutty secretary, or her "sex slave" outfit. Her slave outfit was black leather crotchless panties, and a couple's leather bra.

When Tamora came back wearing her maid outfit and sat nearby. "Master, I'm pleased to be able to serve you once again."

"Thank you, slut," I told her happily, groping her thigh, "I will be sure to make use of your services later. Be sure to pack for our trip. I'd hate to have to punish you for poor preparation."

"As my master wishes," Tamora bowed, then scampered off to pack.

Mary was increasingly slumped in her chair, and I worried she was getting depressed. The girls slowly dispersed until it was just Courtney, Cindy, and Mary, though I could see Sarah's shadow as she waited outside the door to listen.

"... I never stood a chance... did i?" Mary asked tearfully.

"What do you mean?" I asked.

"I wanted to be your first," Mary cried quietly. "I wanted to marry you and have your kids. Be your only one. But then Cindy said you and Nikki were doing it, and I didn't want to believe it. Then she said she saw you and Courtney do it, and I'd lost that, but I told myself I could win you back, you'd be my first and we'd be together... but... I'm not rich, I'm not hot, I'm not special. I'm not going to replace Courtney."

"Well, you aren't replacing Courtney, but that doesn't mean you aren't special or attractive," I consoled her.

"And you can look at the bright side," Courtney informed her, "most girls, once their crush is committed, have to deal with the fact that they can never be together. You get the chance to still be with Tom. You can still live together, still have sex, still have children, the only thing you won't get is a wedding and a marriage certificate. And if the government's approval is all you sought, your love of Tom was superficial at best. Or was he just a prize to parade in front of your family in a Tuxedo while you got to wear a princess dress?"