Life settled into a sort of joyful, pleasant cadence. Midterms came and went, Courtney and I got the top grades in our class. The other girls, benefiting from the collaboration and understanding, also saw their grades improving.
Sex was plentiful and varied. Suki discovered kama sutra, and started experimenting with various positions and styles of sex. Debbie and Abby discovered that they enjoyed roleplaying, Abby in a position of authority, Debbie being forced to fuck me however Abby chose. Brittany got to be really fond of twerking with my dick buried in her ass. Tina was a long-haul fucker, I would drill her holes and pound her for as long as I could, making her orgasm a dozen times, and then when I was spent she would suck me back to an erection and ride me until she couldn’t move. Sarah got off on making me feel loved and appreciated, making sure my every need was met… that and occasionally being bent over a piece of furniture and and fucked with her skirt pulled up and her panties pulled aside.
Courtney and Khloe settled into a sort of relationship. Khloe insisted she was my concubine and as Courtney was my primary woman, that made Courtney her superior or manager. Courtney’s every wish was her command. Khloe was happy with this, and luckily Courtney wanted her friend to be happy. The biggest adjustment Khloe had to make with this was the idea that Courtney and her could have sex with me at the same time. Courtney still loved licking my sperm out of her harem sisters and having them lick my sperm out of her. Since Khloe insisted on obeying Courtney, she started to develop quite the taste for my sperm, and started really enjoying a tongue cleaning out her freshly fucked cunt.
Before long, Thanksgiving was upon us. Most of the girls would be going home to their families for Thanksgiving, as would I, with Courtney accompanying me. Brittany didn’t have anyone, and Suki couldn’t fly to Japan to visit her parents. Suki was a dual citizen, and her parents had moved back to japan to care for her ailing grandparents. Since the two girls would be alone in their dorm rooms, Courtney invited them to spend the holiday in our house, and made sure they had plenty of supplies including enough to make their own Thanksgiving dinner.
Finally, the day arrived. Courtney had gotten permission to use the family’s jet to fly us to my home. We saw the rest of the girls to the airport as their flights were all pretty close together, the day after classes got out for the holiday. They headed off to their terminals and we headed to the private portion of the airport. There was no security check, no place to check our luggage, we basically arrived and met with the pilot.
“Courtney, it’s good to see you again. How was your semester?” The main pilot, Martin, greeted her. “And who is this?”
“Martin, this is Tom. My boyfriend.” Courtney proclaimed.
“Tom, you are a lucky man. Courtney is quite the catch, if you can keep her.” The copilot, a man named Shawn, congratulated me. We took our luggage out and loaded the plane. It was a weird experience, just walking up to a plane, walking up the steps and being in the plane.
“Howard reminded us you don’t drink alcohol, so we swapped out the alcohol for sodas.” Martin informed Courtney, “I hope that isn’t a problem for your boyfriend?”
“Oh, Tom doesn’t drink either.” Courtney informed him.
He glanced at me with a raised brow.
“My father drank enough for all of his children before he got sober. We decided we’d leave it at that.” I told him.
“Ah, I’m sorry that was your experience. But hey, at least we don’t have to worry about you two getting drunk in the back and making bad decisions.” He consoled me.
We got in, the outside door was closed and the pilots took to the cockpit. In a matter of minutes, Martin came over an intercom instructing us to buckle in for takeoff. Courtney and I sat in seats facing one another and buckled in. I would have had to stretch to touch her. People would kill for this kind of legroom on a commercial flight.
In addition to several seats facing each other, there was a couch like seat, a couple fridges and other conveniences for during flight. A TV covered the wall between the cockpit and the cabin.
“Wow, flying private really expedites the process.” I marveled.
“I thought we were going slow…” Courtney laughed, “How long does it usually take to get off the ground?”
“Well, it usually takes about an hour just to get through the security checks and get your bags taken care of.” I explained as the plane started moving. “Then it can take a half hour to load the plane, and another ten to twenty minutes to get clearance for takeoff.”
“Wow… I guess that’s another thing to add to my list of things I didn’t know I had so good.” Courtney remarked.
Within moments we were ascending into the sky.
“Alright, we will be reaching cruising altitude in just a few minutes.” Shawn’s voice informed us. “We’ll let you know when we do, and you’ll be free to move about the cabin.”
“So, Martin usually ends up visiting the restroom after we reach altitude… but once he’s done, we’ll probably be alone for a few hours during the flight.” She lifted her skirt, shifted her thong to the side and stroked her pussy invitingly. “Are you thinking on the chairs or the couch?”
“The armrests on the chairs could get in the way. The couch looks far more appealing.” I told her. “Though we probably don’t want to spend the whole time having sex. Who knows when Shawn may have to take a bathroom break.”
“Okay, so just a couple of quickies.” Courtney laughed. “Sounds fabulous to me.”
As she had predicted, about five minutes after we reached cruising altitude, Martin came through to use the bathroom. He found Courtney and I relaxing on the couch watching the Fellowship of the Ring, extended edition, and sipping on the fanciest sodas I’d ever seen.
“Now, if Shawn has to go, I’d give it five minutes before he uses the bathroom.” Courtney guessed.
I was imagining what we’d be doing in my head and three minutes later, when Shawn stepped out to use the bathroom, I was guessing if Courtney hadn’t predicted it, I would have been balls deep in her.
This time, the moment the latch clicked on the cockpit, Courtney was diving on my crotch and pulling out my dick. A few quick sucks and she was satisfied. She turned around, pulled her skirt and thong out of the way and lowered herself onto my cock. I guided my length into her. She started bouncing and grinding.
Perhaps it was the naughtiness of what we were doing, or maybe it was the altitude, but in a matter of moments Courtney was coming hard on my cock. She had to bite down on her wrist to avoid screaming, though it didn’t draw blood, I was nervous it would show. Her climax led me to shoot my load deep in her and by the time the Hobbits arrived in Bree, Courtney and I were sitting safely next to each other, my sperm soaking into her thong as we discussed the soda and then my family’s Thanksgiving traditions.
We discussed traditional Thanksgiving foods. We talked about how my family rarely did black Friday sales. How until my grandparents had passed, we’d gotten together with my aunts and uncles for Thanksgiving. It blew her mind that I had 64 cousins, and that I knew and had spent time with all of them growing up. Courtney had 3 cousins she knew of, and she’d met them Maybe a half dozen times in her life.
“Do you think Martin and Shawn were told to keep an eye on us to keep us from doing what we’re just did?” I casually asked Courtney.
“If they come out of the cockpit again, yes.” Courtney agreed.
“What do you think the odds are of that?” I laughed.
“Not good. Daddy trusts me.” Courtney protested.
“I’m betting they were told to watch us.” I countered.
“Oh? A bet, is it? What do you want if you win?” She laughed.
“I want to take you to a sex store, but restraints, take you back to the Airbnb and you’ll let me restrain you and fuck whatever holes I want for an entire evening.” I told her.
“Oh, that’s hot.” Courtney replied, “Damn, can I ask for that too if I win?”
“That’s not how bets work…. though there’s nothing stopping us from doing it regardless.” I laughed with her.
“Maybe if I win, you let me spend time with your siblings, just me and them..” Courtney countered.
“Well, as far as I know, only Cindy is going to be home. It’s the year Melody and Joe spend with the in-laws. But I could set up a sister date for you and Cindy, I don’t think that’d be hard to pull off.” I conceded.
“It’s a bet.” She proclaimed, and we shook on it.
We half watched the Lord of the Rings as we chatted. I began to feel like I could go for round two as the fellowship of the ring reached the mines of Moria. I looked over at Courtney and she was looking at me the same way.
I was about to lean over and kiss her to kick off our second quickie of the flight, when there was a clicking noise. Courtney and I both looked up to see Martin work her way back to the bathroom. I almost celebrated my winning of our bet but Courtney pointed to the still open door to the cockpit. I nodded and we talked about my family some more.
Since Cindy and I were closest in she we’d spent a lot of time together growing up. I knew she used to play volleyball, but I want sure if that was still there case. While we’d been close, we drifted apart when I’d become a teenager, and it’d gotten worse while I was dating Nikki. Then when I dumped Nikki because she’d cheated on me, Cindy had become insufferable.
When Martin came out of the bathroom and closed the cockpit door, Courtney gave an exasperated sigh. “I don’t know which is worse, that Daddy doesn’t trust me, or the fact that I lost the bet. Probably not losing the bet, I’m kinda glad I lost that, though I’m sad I’ll miss out on the sister date.”
“Eh, you were going to let me restrain you and fuck you how I wanted, so I can still give you a sister date with my sister.” I told her. “You think that Shawn will wait long enough for another quickie?”
“Let’s see.” Courtney challenged me.
She whipped a leg over my lap, and opened my pants, letting my rapidly hardening cock out of my pants. She stroked it a few times to get it hard, then lifted her skirt, slid her sperm soaked panties aside, and lifted her pussy to the top of my dick. She guided me inside her and slid her knees forward a bit to get a better angle. She lowered herself and began riding my cock. Feeling my sperm lube her pussy for another fucking was hot. Courtney rode my cock fast, hard and dirty, grinding and bouncing alternatingly.
I groped her tits and found surprisingly little resistance. “Are you not wearing a bra?”
“Didn’t… want… one… in… the… way.” She grunted as she drove my cock deep into her pussy.
Courtney clenched her jaw as she orgasmed. She then upped her efforts to make me cum. I groped her ass and tits, and felt my climax rising. I shot my load, mixing old sperm and new. Courtney got pushed over into a new orgasm. She let out a yelp, before clapping her hand over her mouth.
There was movement in the cockpit. She scrambled off of me, pulling her thong back into place. I quickly put my cock away and redid my pants. The door opened and Shawn came out, “Everything okay back here?”
“Yeah, I opened a new soda and almost spilled it.” Courtney laughed, “But thank you for your concern.”
Shawn looked at us, and I could tell he was suspicious. He decided we were fine and re-entered the cockpit.
“Fuck that was close.” Courtney breathed. “But damn, these orgasms are amazing. I come so easily and it feels so good.”
“That’s what the mile-high club is all about.” I told her.
“We’d better call it at two quickies, though. Martin and Shawn are suspicious now.” Courtney informed me.