Too Good To Be True Ch. 17

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Tom finally meets Courtney's family.
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Part 17 of the 29 part series

Updated 02/11/2024
Created 05/22/2023
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Chapter 17

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.

"That's good that worked out for you." Khloe told her happily, "I'm on probation while my parents decide whether or not to disown me."

We all stared at her, as her words sunk in.

"Did you tell them about the harem?" Suki asked, concerned.

"That's the thing!" Khloe exclaimed, "They put me on probation when I told them I had gotten my vaccinations and visited a gynecologist!"

The girls were thoroughly confused.

"So it turns out my great great grandfather was some big shot preacher, and he decided that illness and death was God's will, so vaccines and doctors are directly in opposition to God." Khloe explained, "His teachings never caught on for obvious reasons, but my family has followed them, or even stricter versions for generations now. When I told them I had learned about vaccines and everything medicine can do, my mother had an emotional breakdown. They forbid me from ever seeing a doctor again, and said they'd made an exception for my period delay pill, but that was done. If I want to be counted as their daughter, I was to stop taking my birth control pill and swear off modern medicine. Well, with everything I've learned from Brittany, that was an easy decision. So I'm on probation until they decide to disown me. But man, I learned they pulled me from school each time there were lessons about medicine or biology, and homeschooled those lesions so they could control what I learned so I would accept the teachings. Man, realizing my family was crazy, but kind of liberating too."

"Well, we're here for you. We will take care of you, even if your family decides to disown you." Courtney declared.

"Thank you... I've realized you guys have been a better family than mine ever was." Khloe declared.

Turns out, the girl in the worst way needing sex was Sarah.

"So, I'm glad we're all back together, but can borrow Tom for a minute... my sister had her husband staying with us in the family house... and my room shares a wall with theirs, and they were VERY noisy love-makers... I've been dying for Tom's cock since my first morning home." Sarah admitted.

The girls sent us immediately to the bedroom.

Sarah almost jumped on me the moment the door closed. "God, I want to suck this dick and then feel it ram my pussy like you are trying to breed me." She moaned, pulling down my pants and whipping out my cock.

"Oh, fuck. A horny session, huh?" I gasped as Sarah pulled her shoulders out of her dress and let it drop down her body.

Sarah came up for air off my cock, "My sister is trying to get pregnant and I can only hear, 'Yes, breed me, dump your cum in my fertile cunt!' so many times before I want it too. But I understand we aren't ready to be having babies yet... but damn, I need your sperm in my pussy now!" And she continued sucking me as she dropped her strapless bra and offed her panties.

I threw off my shirt and Sarah took care of the rest.

I then picked her up, put her on the bed, climbed up and slid balls deep in her pussy.

"FUCK! YES!" She breathed as the aching emptiness inside her filled with my dick. "Dump your load in me, use me like a cum bucket!"

I started plowing her, almost immediately causing her to orgasm. Man, sometimes when your woman is horny enough, the orgasms come easily. She was constantly begging for harder and faster fucking, and I did my best to give it to her, slamming into her cunt with speed and force.

"FUUUUUUUUUCK! She screamed, her orgasming pussy bringing me to my peak. "YES! FILL ME WITH YOUR SPERM!" She moaned as I squirted my white love juice in her, painting her uterus white.

She pushed me over and started sucking my dick, bringing it back to hardness as it tried to soften.

"Sorry, but I want it in my ass too." She whispered, lowering her puckered hole onto my dick.

"Shouldn't you lube me up fiiiiiiiirst." I gasped as her ass swallowed my dick.

"What.. do... you think... the.. spit... was for?" She asked, slamming her butt down on my hips. "FUCK!"

She rode my dick with her ass, the tip going around the bend in her bowels every time she slammed down. Her tits bouncing invitingly were impossible to ignore and I started groping them and pinching her nipples.

"FUCK, YES TOM!" She gasped, continuing to slam her bowels with my cock.

After just a minute of this anal abuse, her body climaxed again, a body rocking orgasm that made her fall off my cock as she flooped to the bed.

"Oh, fuck, I'm going to be walking delicately, but fuck, that was good." She moaned.

"Sorry, you asked for it rough..." I excused myself lamely.

"Oh, no. Tom, you did exactly what I wanted." Sarah assured me. "My fucking sister and her fucking husband just got me so horny, I needed a fucking I couldn't walk away from without being bowlegged. And damn, you delivered. Let's rejoin the others."

We pulled our clothes on and walked back out, Sarah obviously feeling the fucking she'd just received.

"Wow, Sarah, not very often you take it that rough." Courtney observed.

"My sister was very graphic in describing how she wanted her husband to impregnate her, and I had to get it out of my system. Damn, I am so glad you are sharing Tom with us." Sarah groaned as she gingerly sat on the couch. "He may have bruised my ass and pelvis, but I'll take it over being horny like that any day."

We fell back into the regular cadence of school and sex, the final weeks of the semester moving fast. Final projects, major homework assignments, and research projects getting done, more often than not, by sperm filled harem girls.

Courtney and Brittany started having me taking half a dozen supplements, but the results were evident, I could start fucking more frequently, with my peak being six times in a day before Christmas.

Once scores were in, the entire harem had nothing but As for the semester, though Khloe barely squeezed her A out.

The girls seemed to know that with Christmas vacation coming, they needed to get all the dick in them they could, and I managed to cum inside all seven of my harem girls, Courtney excluded, the day before our flight to Courtney's parents house.

The Alaska king bed had become very popular, since the nine feet of width let us all cuddle, though without much space leftover. Tina, Khloe, Suki and Sarah still preferred their intimacy with less of the harem present, but having us all in a naked cuddle pile had its appeals still.

The following morning, Courtney and I were the first to leave. The other girls who were leaving would have flights over the next two days, with Suki, Brittany and now Khloe staying at the house Courtney and I shared while we were away.

Martin and a new copilot, a ginger woman with a-cup tits and without enough ass to fill her pants named Corinne, were waiting for us when we got to the airport.

"Welcome aboard!" Martin welcomed us, helping us load up the plane. In addition to our new copilot, Courtney's chauffeur, a gentleman of some years by the name of Clarence who could have passed for Alfred from the Batman comics, joined us for our flight.

"It hasn't been the same at home without you, Courtney." Clarence informed us, "Your mother has gotten to be quite the lonely empty nester."

"Has she been sleeping around behind my father's back?" Courtney demanded.

"Oh, heavens no. She knows the staff has no great love for her, your father is the one who took us all in and took care of us. She's realized she burned too many bridges when she married your father and started treating us like we were below her. She's trying to win us over, but most of us remember how she really is and it doesn't help her that she reverts to her old behavior after a few drinks, and she is fond of her drinks." Clarence assured Courtney, "We'd inform your father immediately, if she tried anything. Though many of us think that had he not had several of us on the cruise she went on over Thanksgiving, she would have taken the opportunity."

"Father got some of the staff on the cruise!" Courtney laughed.

"Myself included, you should have seen your mother's face when she saw me at the pool the first day. She was wearing a swimsuit that was barely appropriate and was clearly scanning for men, when she saw me and almost burst into tears." Clarence laughed, "Your father had quite the chat with her on our return."

"Oh dear, is mother on probation again then?" Courtney pressed.

"Of course, but you have yet to properly introduce me to the young man sitting next to you!" Clarence stated, changing the subject.

"Oh! Of course, how rude of me. Clarence, this is Tom. Tom, this is Clarence. Clarence has helped raise me and take care of me since I was a toddler." Courtney explained.

"I've known this little miss since before she could talk, though that wasn't until she was four years old." The gentleman reminisced.

"Clarence, I hope you'll like Tom. He has taken such good care of me this semester, tutoring me, helping me catch up in my classes and he got me a job!" Courtney exalted, presenting me with a flourish.

Clarence raised a brow, "Does this mean you have finally given up on following your mother's advice?"

"Absolutely. Tom helped me out when there was an issue that... mother's advice couldn't get me through. I told him everything, and he stuck by me, and has helped me get to where I actually understand what is going on! I earned my As this semester and I couldn't have done it without him." Courtney declared.