There next morning I woke up and immediately went to get Courtney and all her luggage. Sign out time was early and I didn’t want her to miss it. On our drive back, Courtney was curious about my anxiety to make sure she checked out on time.
“Well, I don’t want your father thinking we’re abusing his hospitality.” I told her, “I really do want to make a good impression on him.”
“This again? I’m sure he’ll love you.” Courtney assured me.
We arrived at my parents house and chatted with my father while killing time before Martin and Shawn would be ready for us.
“So what time is your flight?” My dad asked.
“One o’clock.” I simplified.
“What are you thinking? That’s only two hours from now! We need to get you to the airport now!” He exclaimed.
“Um, dad, Courtney’s father has us flying private…” I explained.
“… what?” He gave a blank look.
“Well, her father is kinda the head of a major investment firm.. and he decided we could use one of their jets to fly here and home… so, one is when the plane will be here ready, but we’re their only passengers, so they won’t leave without us, and since we’re flying private TSA isn’t a thing we have to worry about…” I told him.
“One of… their jets…?” He repeated, emphasizing the plurality of the word ‘jets’.
“The small one.” Courtney informed him, “We mostly only use the big ones for flying large groups or cross ocean flights.”
“Holy… just how rich IS your family?” My father asked.
“They are firmly in the billionaire class.” Courtney informed him. “And I’m his only child. My aunt and uncle aren’t on speaking terms with us, so… there kinda isn’t anyone else to spend the money on, since all my grandparents have passed away.”
My father visually processed that inheritance situation. “And there isn’t an engagement ring on that finger because…?” He teased, over the top sarcasm in his voice.
Courtney giggled, and I rolled my eyes, “I’m not dating her for her money. And we’ve talked about it. Once we graduate, then we’ll look at tying the knot. But that gives us enough time to make sure we’re truly compatible, and it isn’t just hormones running wild and we’re going to end up divorcing miserably in a few years.”
That had been a tough conversation to have. I had to face down some serious fears and insecurities and so had Courtney. Her mother’s situation had made her hyper aware of the realities of divorce potential, since her father had wisely protected all his wealth with a bulletproof prenup, and should her mother step a toe out of line, she’d be out and penniless with no family and no financial security. My family was fully aware that my mother had had to make my father choose between an AA pamphlet or the prepped and ready divorce papers. It had been the kick in the gut that had given him the commitment to become sober.
“Glad you are thinking about the future. That’s important.” He laughed, “Maybe your mother and I can retire and become full time cruise residents for real!”
It was a thing he talked about fairly often. How he’d seen that it was cheaper to live full time on cruise ships than to live in a retirement home.
“Well, if this relationship countries to work out, maybe you can just have your own resort with personal staff instead.” I told him.
That was how Courtney’s grandparents had lived out the ends of their lives. Courtney’s father still had the mansion with elevators, and everything else an elderly individual needed to navigate their old age in grace. They still had private nurses on staff at all their residences, so it wasn’t far-fetched at all.
“Well now, there’s an idea.” He laughed again.
Cindy butted in at that point asking if we had plans for after college.
Courtney and I exchanged looks, “Not 100% yet, but since we’re spending Christmas with Courtney’s father, we suspect he’ll have some input on that.”
Courtney’s father had made a comment to Courtney that if she really liked this boy of hers, he’d have to start preparing me to take his place as president of the investment firm. Courtney said that comments like that from him were rarely, if ever, a joke.
We continued to discuss plans, turns out Cindy had a short list of colleges she was interested in. She had a total of ten colleges, including the university that Courtney and I were attending, as schools she was interested in. She’d even started applying now.
“Some colleges now expect you to start applying before you even start your senior year.” Cindy informed us.
That wasn’t how I’d done it, applying right after I graduated, but I wished her luck. I learned she was actually doing really well in school, but competition for the valedictorian position was tight.
“There are five of us that could be selected. We all have 4. 0s, we all have perfect or near perfect attendance… my lack of extracurricular activities the school recognizes may see me lose out though.” Cindy admitted.
“Well, we are rooting for you.” I told her. Courtney seemed amazed through the entire discussion.
Cindy had offered to drive us to the airport, and soon enough, it was time to go.
We waited by the packed car for Cindy to run to the bathroom before we headed out.
“Your family is amazing.” Courtney started, “In my family, as soon as competition was discussed for a thing like your sister’s chance to be valedictorian… my father would start talking about how much he would have to donate to the school or some program to make it happen… but you guys just trust I’m her abilities and merit… I’m honestly jealous, you know you’ve earned everything you have and it’s not just because of who your parents are that you have what you’ve earned…”
“Courtney, you are an incredibly intelligent and talented woman.” I told her, “And many things money can’t buy. You will graduate knowing you’ve earned it and learned everything you needed to to earn that degree. If anything, the speed at which you’ve caught up should tell you something. And you know I’m not faking that.” I informed my discouraged girlfriend.
She hugged me and Cindy arrived to drive us to the airport. When we arrived, Cindy hugged us both.
“I’m gonna miss you two.” Then she slugged my shoulder, “Don’t do anything stupid, I like this one. So don’t mess up the relationship. I want my new sister, ya hear?”
I laughed and Martin and Shawn helped us load the aircraft.
Apparently, one of these employees of Courtney’s father had been in the area and would be serving as our flight attendant.
“Damn,” Courtney whispered to me, “I wanted more mile high fun, but hey, at least you’ll be ready for Suki and Brittany when we get home.” Most of the other girls had late night flights so they’d have to wait for Monday at the earliest.
The flight was uneventful, though it was nice being waited on, hand and foot by the attendant.
We arrived back home that afternoon just as dinner time was hitting. We walked through the door to the smells of teriyaki and steak. Brittany and Suki were still there and we had a lovely dinner, and had to digest before the two girls grabbed me and dragged me to the bedroom.
Suki took my load in her tight pussy, then Brittany sucked me erect and rode me with her ass, orgasming repeatedly as she twerked my rod deep into her bowels.
“Fuck, it is so nice being able to satisfy those needs.” Suki breathed as the four of us cuddled in the bed. “It wasn’t too bad the first couple of days, I guess knowing you’d be back today… Brittany and I got excited. Christmas break might be tough, you’ll be gone for a full two weeks!”
Two weeks of trying to impress both Courtney’s father and her mother. Her mother may not control the money, but if she could control Courtney’s father, that didn’t matter. And I suspected, I wanted both of them on my side if I was to marry Courtney.
Monday came and classes were right back to it.
Between classes, Courtney and I spent most of our time in the student center, it was near enough to our building to be convenient, and had access to food, school supplies and everything else we’d need.
On my way back from the bathroom, Abby grabbed me and pulled me into a side hall, and into an alcove. “Quick, nobody will see us here, fuck me! I need your dick!” She begged, dropping her thong to her knees and lifting her skirt.
I whipped out my rapidly hardening cock and plunged it into her needy hole. Abby clapped her hand on her mouth to stifle her moans, and we both felt the urgency. Anyone could wander down this lesser used hall and find us fucking. Luckily we knew surveillance at our college was a joke. These buildings had been built long enough ago that wiring for the lighting had been tough, so they didn’t have cameras in most of the buildings, including the student center. I groped her tits under her shirt as I plowed her hole hard and fast.
After just a minute of my fast, hard fucking Abby came, pushing me over the edge and I dumped my sperm in her baby cavern.
“Fuck, I don’t know what came over me.” Abby said, pulling her thong over her sperm filled cunt. “But I’m glad I did it. That was so hot, we’ll have to see where we can sneak more quickies like this in!”
“I enjoyed it.” I told her, securing my dick inside my pants once more, and we returned to Courtney.
“Did you guys just… Here?!” Courtney gasped, seeing the content look on Abby’s face.
“Yep. It was hot. Pulled him into an unused hall and… yeah… it was great.” Abby related with a satisfied smile.
“And here I thought Debbie was our exhibitionist.” Courtney laughed.
Abby sat, “I don’t think I’m an exhibitionist, per say, because I didn’t want to get caught, but fucking in a public space, quickly so as not to get caught, then walking around with the evidence inside me… that’s hot.”
“Oh, a thrill seeker instead of an exhibitionist.” Courtney mused, “Because you’re right, Debbie would have hoped to get caught.”
“Fuck, having sex on a picnic date with only bushes hiding us from other people at the park… shit, that’s so hot as long as we don’t get caught.” Abby plotted excitedly.
“Oh, you are naughty. You’ll have to let me know how that goes.” Courtney giggled.
That night, the harem gathered, and surprisingly, several of the girls were fine, they’d all gotten fucked pretty well before be left for our respective Thanksgiving celebrations.
I’d thought for sure Debbie would need sex, but she’d just worn skimpy bikinis when her family went swimming and masterbated in the hot tub where no one could tell.