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.