I laid down next to her and spooned her for a few minutes. Then we got up and Courtney laughed, “There’s a waterproof mattress cover under the sheets. I thought it would protect the mattress from my blackmailer’s pee, instead it’s protecting it from my squirting. I’m glad I got it and I’m glad I got the upgrade in partners.”
We got dressed and got to work as graders. It turned out this was a perfect opportunity. We probably weren’t the fastest, but by going over answers, why they were right and why they were wrong and the thought processes and reasons for them we were able to provide meaningful feedback to the students and Courtney was picking up things at a phenomenal pace.
Working with her, Courtney was incredibly intelligent. She was learning fast and picking up on even complex ideas as I explained them, though the fine mechanics took her more time. Math was the hardest, but even there, she learned fast. She might not have her multiplication tables memorized but she had a calculator on her phone and it wasn’t a big issue.
After about an hour, I sat back. “Courtney, I still don’t understand. You are smart. Like really smart. You said your mom made you start cheating in middle school, but you are clearly not dumb so you should have been fine. And… you shouldn’t have needed to cheat. Why did she do it?”
Courtney sighed, “I don’t know. I think I just struggled with a few concepts for a bit, but my mom was never good in school. I am guessing she cheated through school and thought I wasn’t going to be able to get through without it.”
She looked at the assignments we were grading. “It was easier at first. The cheating. What middle schooler doesn’t want to be able to skip doing their work? It was great for the first year or two, then I realized I’d fallen for the trap and couldn’t catch up without help.”
She rolled a pencil back and forth, “Then mom pulled me out of the private school and gave me tutors. They didn’t even try to teach me, like you are here. They were just interested in getting me to be able to cheat through the tests to get my GED. A couple of them were even hired to pretend to be me to take the SAT and ACT so that I could get into college.”
My heart broke for Courtney. She didn’t need that. She didn’t deserve that. She was smart! I could get her caught up within a few months, and I was confident on that. There would probably be holes in her education because her mother had screwed her over.
“Well, I’m gonna do my best to make sure you never have to do that again.” I assured her. “Your mother is a monster for that. I never want you to feel bad about not knowing something because the people in your life that should have worked the hardest to teach you didn’t do their job. That’s their fault, not yours.”
Courtney smiled, “Thank you, let’s get back to work.”
We kept working until it was time to take a break for dinner and Courtney laughed after a few minutes preparing the shrimp pasta she was making. “I’m torn!” She admitted, “I can’t decide which of my friends to let you fuck first! I’m so excited! I’ll even be there to see you deflower them! That’s so hot!”
“You’re sure you want to do that?” I prodded, “I mean, I am happy with just you.”
“Oh, I am sure. They deserve to enjoy the kind of experiences you have shown me.” Courtney insisted. “They just need to find the right guy. I found the right guy, and I am willing to share, so long as they are willing to prove they are safe.”
I began to accept that Courtney actually wanted this. She wanted to share the joy and pleasure she had found with her friends. And I guess that was the highest form of love, sharing that which makes you happy.
“Do I get any say?” I asked.
“Maybe.” Courtney teased. “I mean, I’m pretty sure several of them will be excited for this.”
“We could host a dinner or a meetup and see who comes and see about making decisions once we can gauge some reactions there.” I suggested.
“I like it!” She squealed. “You get to meet all the girls you’ll be fucking and I get a night with my girls!”
Immediate preparations began.
It would be the next weekend. It was Friday and Courtney initially wanted it to be the following day, but in the end we delayed a week. After some debate we kept it small, only the six most likely candidates.
The next day, being saturday, I finally had time to organize my stuff.
“Is this really all you have?” Courtney asked in disbelief as I hung up my one nice suit, white shirt and three ties. We put my dozen shirts and three pairs of pants on shelves. I only had 3 sets of shoes.
“We’ll have to get you more clothes, there’s nothing here you could wear to any social events.” She informed me.
“If you say so.” I told her.
“You’ll let me dress you?” Courtney giggled.
I shrugged. “I really don’t care. So long as it isn’t uncomfortable.”
“YEEEEEEeeeeeeeeeeeeeesssss.” Courtney hissed, excitedly.
The rest of the day was spent organizing my stuff and shopping. Courtney insisted on paying for it, and my wardrobe was tripled. I only got my PC and monitor in the game room but didn’t get them set up.
The weekend and next week went well. Eventually, despite her protestations otherwise, Courtney had to admit, her throat, asshole and pussy were simply too sore from repeated, vigorous, fuck sessions we had to take a break.
Grading went well and tutoring Courtney was far easier than I expected. She had a legitimate desire to learn, and we split our time between teaching her what she needed to know for our upcoming assignments and tests and reviewing what she had skipped. She had most of her general class credits already, and for the most part we skipped those. For example, economics, she didn’t need to know that. The class only covered the most basics of principles and I learned she had her own devoted accountant, and a team managing her trust fund she could draw on at any time.
Finally, Saturday morning arrived. Courtney announced proudly that her holes were ready to be fucked again.
“But I want to wait until after the party. I know I’m going to get horny thinking about you fucking all of them.” She informed me.
Later, Courtney still struggled with how small my wardrobe had been. “What did you even wear to formal events?”
“Well, I’m a guy. Most people don’t question if a guy wears the same suit. And I couldn’t exactly afford a closet full of clothing I’d rarely wear.” I informed her as she tried on another dress for tonight. She was having a hard time debating between classic, slutty, and fun.
“Well, I bought you something to wear tonight. Gotta have your image match the gentlemen you are.” She told me and handed me a bag with a polo and khaki pants. “Your shoes are okay for tonight. We aren’t being super formal.”
She decided on a v-neck blouse and a skirt that was tight enough to tease me with her ass, but also would let her flash her panties at me or let me reach up there if she wanted it. I knew because she demonstrated the flashing, and told me the second part.
“Do you want me to have an erection all night?” I complained.
“Of course!” She laughed, “You’re getting to see the goodies the girls bring, why shouldn’t they at least get an idea of what you bring to the bed?”
Finally ready, we realized we had a few hours to blow before the party.
So I set up my computer and we started playing games together for the first time. We started with League of legends, a multiplayer online battle arena, or MOBA for short. Teams of five competed against each other in an all-out brawl, but since your characters always started at first level basically broke, you had to farm gold and experience each game by fighting waves of minions and killing your opponents who would respawn.
Since Courtney was an ADC main, I decided to play support. We’d stick together in bottom lane and I’d see how good she was.
Turns out, she was good. Not pro good, but better than me.
“Damn, I’m rusty.” She groaned.
“You have the most gold on either team and more than half our kills.” I pointed out. I’d landed Blitzcrank, one of my favorite supports, and he hadn’t been banned by the other team during draft picks.
I landed a grab, pulling the enemy damage carry out of position for Courtney, playing as Jinx, to jump on then and annihilate them.
“Says the support with more gold than the enemy top laner.” She countered.
“When assists come this easy, I’m not complaining.” I informed her.
We won our first round, then decided since it had run long we’d just play some Halo co-op since we could just drop that whenever people started showing up.
Turns out it was a good call, because fifteen minutes later, the door got its first knock.
“A half hour early?” Courtney chuckled, “Someone’s anxious.”
“They know I’m not fucking them tonight, right?” I asked as I powered down the system and Courtney got up.
“They don’t know you’re fucking them at all. But Sarah may have guessed. Let’s see who our first guest is.”
Courtney opened the door to reveal a tiny asian young lady. She had small tits, smaller than Courtney’s, and no butt worth mentioning, but her tiny waist still made her hips flair.
Holy shit, I thought, there’s nothing to keep me from going balls deep into any of her holes, and she looks flexible as fuck.
“Suki!” Courtney squealed. Hugging her and inviting her in.
“I didn’t realize your boyfriend would be here…” she said, tugging at the bottom of her short skirt. “I thought we’d just be talking about him.” Her top was loose, probably because of her insecurities about her breast size, and her skirt barely made it halfway down her thighs.
“He’s a big boy, he doesn’t mind us talking about him in front of him.” Courtney teased me.
“You said you’d tell us about having sex with him!” Suki whispered, trying to be quiet enough I wouldn’t hear, but failing. “We can’t talk about that with him here!”
“Why not?!” Courtney asked at the same volume.
“Because I am already horny from thinking about it all day!” Suki hissed, “I will get more horny talking about it and you know I can’t resist touching myself when I get that horny.”
“It’ll be fine, honey.” Courtney assured her, “All the girls have seen you masterbate before and if you feel bad including Tom in that, I can make him masterbate for us too. The other girls would love that.”
“Courtney!” Suki said louder, and ran down the hall to the bathroom. I swear she was squeezing her legs together.