I shrugged, “My ex used to do that, her breasts were D cup. And having had hers and yours, I’d take yours any day. Titty fucks are way overrated.”
“Really…?” Courtney pressed, doubt obvious on her face.
“Why friction burn both my dick and your breasts, or waste half a tube of lube, and make you chest hump my dick for a half-hour, when I can get the same result, with more pleasure from your ass or pussy? My ex tried twice before she gave up. Don’t believe the shit porn shows.” I told her. “Like I said, my ex had D breasts, and the titty fucks are overrated.”
“Oh, and what asses don’t matter either?” Courtney chided, but I could tell she felt a bit better.
“Oh, some ass is great. But once again,” I grabbed a handful of her ass, “more than a good plump handful is a waste…” and leaning in, “and gets in the way of good deep anal.”
Courtney almost purred, “That deep anal is nice… what were we talking about?”
“How are you dealing with the asshole blackmailer?” I pressed.
“Oh, well… I kinda dug myself in pretty deep. From what he showed me, he has me dead if he goes to the honor office. So, for now I have to deal with sending him nudes and… letting him fuck me.” She admitted, “But you help two fold here. First, you give me good sex and help me prep to get raped whenever he wants.” I couldn’t help but wince. “And secondly, you’ll catch me up on what I should actually know so I can stop cheating and then we can try to work out how to catch or scare him away.”
She thought and continued, “I can’t reach out to daddy, because he’d be developing. He doesn’t know I cheated through high school. He thinks I actually honestly got into college, and he is so proud of me. That is why my trust fund is as big as it is. I’d have to tell him everything and he’d probably take my trust fund. If I call my mom, she’d probably just get a private investigator and a hit man, but knowing her she’d mess it up and make everything worse.”
I blanched.
Courtney nodded, “Yeah, that’s a mistake I’d rather her not make. I just found my man, I’d rather not accidentally get you hurt. So I want to take care of this myself.”
I felt better about that. “So how much do you know about him?”
Courtney flopped on her back, her tits bouncing tantalizingly. “That’s the worst part. I basically know nothing. All our communication is through a BS account he made on the school messaging app. Don’t know how he pulled that. I thought only students could make accounts there but his account doesn’t link to a student account. And that I know of, we’ve only been in the same room once, he made me blindfold myself first and he contorted his voice.”
“And that’s when he fucked your ass?” I asked.
“Yeah,” she said.
“And you didn’t try to take the blindfold off?” I asked.
She blushed, “I kinda couldn’t.”
“Why not?” I asked.
She reached over and pulled the handcuffs out of a drawer at the side of her bed. “He had me handcuff myself, naked to the headboard.”
“So when did the conversation about fucking you happen?” I asked.
“It didn’t! I didnt realize he was planning on fucking me until he opened the front door!” She exclaimed.
“Wait, so he told you to get naked, put on a blindfold and handcuff yourself to your bed and you didn’t realize he was planning on fucking you?” I asked.
“Well, he doesn’t exactly tell me what’s coming next.” She explained defensively, “I’d been told, ‘Get naked’ often enough that wasn’t weird. Then ‘put on the blindfold’ was weird but I figured he’d made me buy it for a reason. And I didn’t think he knew where I lived, and at first it was just my legs handcuffed, and he was making me video call him so I figured he wanted a show. Then he said ‘do one arm’, then when he told me to do my other arm I was just confused because he made sure the keys were out of reach.”
I smiled, “You realize as soon as the first leg was handcuffed, if you couldn’t reach the keys that meant someone else was going to have to get them for you. And since he was the only one who knew what was going on, and he seems to want to keep this between the two of you… does he know you are telling me?”
Courtney sat up, “Fuck! He’s gonna be pissed!”
I put a hand on her shoulder, “When he found out about us fucking again, did he know what’s going on?”
She shook her head, “He didn’t even know you were the same guy from yesterday.”
“Then he wasn’t watching yesterday, didn’t hear us talking, and didn’t get the same today.” I explained. “He’s probably just watching and heard you were taking a guy home. And you had to send him pictures yesterday to show you had found someone to take your virginity, right?”
She calmed down. “I need to tell him I got a tutor so he doesn’t assume we’re fucking everytime you’re over here… Though we probably will be.” She grinned at me.
“Probably best to be honest with him, he’s kept his end of the bargain this far and kept your secret, so let’s not be stupid and take risks.” I said.
She nodded. “That’s what I figured. Anyways, as fun as hanging out naked is, I actually want to use my tutor for more than a sex partner. I want to learn, but first, you said you needed to pee and I want to see if I can handle drinking piss straight from the hose.” And she leaned down and took my dick in her mouth for a quick suck, before pulling off and heading toward the door. She stopped at the door and wiggled her ass at me. “We’ll do it in the bathtub again, in case I can’t drink it fast enough, I don’t want it all over my bed.” And she headed down the hall as I got out of bed to follow her.
She had a towel down for her knees, and was getting on her knees when I walked in.
“Are you sure you want to do this?” I asked.
“Yeah, after you pissed in my ass last night I did some research. Pissing in my ass is fine. Pissing in my vagina is okay on occasion, but it can throw off the PH if you do it too much. Drinking piss is okay, just not all the time, as long as you don’t have a bladder infection or UTI.” She assured me.
“I’m warning you, I haven’t been drinking much water today, so my pee won’t be diluted.” I cautioned.
“Okay, thanks for the warning.” Courtney replied, and curled a finger beckoning me over.
I shrugged and stepped into the tub with her. She took a hold of my cock, stroking it a few times to get it to start hardening enough to go in her mouth. She licked a moment, then with a slurp, pulled the heads into her mouth, just past her lips and gave me a thumbs up.
Who was I to deny her? I couldn’t exactly tell her that I was her blackmailer and I wouldn’t force her to drink my piss, so I gave her what she wanted.
I relaxed and let it flow. I wasn’t trying to drown her, but I also hadn’t peed for most of the day, so my urine was plentiful. I felt her flinch from the liquid hitting her tongue, but true to her intention, her throat started working as she sucked the pee down her throat. She’d let her mouth fill before gulping it down. I was peeing slowly, so as to not drown or overwhelm her, and she kept up easily. It was manageable enough that she started getting adventurous and licking my peeing dick as my bladder finished emptying. She pulled off my cock to swallow the last of my pee, gulping then took a few deep breaths. “That was interesting. It was definitely salt, and a bit bitter, but if that was all it took, I can definitely handle that.” She demurred, “And I felt sexy doing it.”
“I could get used to doing that if you like it.” I admitted.
She smiled, “Probably not every time you piss, but I wouldn’t mind. Was that a full bladder then? I can handle that.”
She got out of the tub, tossed the towel she’d been using into her hamper and started using the toilet. “Get dressed, we won’t get any actual tutoring done if we stay naked all day.”
I went to the bedroom and grabbed my clothes. I opened the college messaging app and wrote out a message as her blackmailer saying that if Courtney insisted on continuing to fuck, even if she kept her pussy for me as agreed, I was going to insist on fucking her ass, regularly, until I could have her pussy.
Then I went and sat at her table in the dining room. Soon enough Courtney joined me.
“Okay, which class should we start on? I want to get caught up as quickly as possible.” Courtney started excited.
“We should probably start with some 100 level courses, you did say you cheated through those, and without the basics, our current stuff won’t make sense. But before we get started, did you send the pictures you need to your blackmailer?” I asked.
“Oh, yeah.” She deflated, “Let me do that quick.” And she pulled out her phone. I discretely watched for the message and pictures to hit my account. They arrived pretty quick.
I started questioning her on stuff from our 110 class, and discreetly hit send on my pre-typed message.
Courtney’s phone buzzed in her hand. “Fuck. He wants my ass again.” Courtney spat.
“When?” I asked.
“Let me see.” She messaged, and typed something up. “I hate waiting for his response.”
Her message hit my phone, “How long until you are going to insist?”
I showed her a diagram of how binary worked to distract her and kept my message short. “Now, send your boy home.” Short messages like that were simple and easy to hide.
She checked her phone, “Oh… he wants my ass… like right now.”
I thought for a moment. “Send him a picture of us studying and say you’d have to explain I’m your tutor and say you’d have to tell me about the bet to send me away now.”
Her message hit my phone, and a few diagrams and explanations later I finally got my response to her.
“Fine. But at 8 o’clock tonight I expect you to be naked, blindfolded and handcuffed to your bed, just like last time. And do a video call so I can verify. I want all the handcuff keys visible.” My message read.
“Fucking asshole.” Courtney seethed. “At least this time I know what to expect.” She showed me the messages.
“Is your ass going to be up to getting fucked tonight? I wasn’t exactly gentle.” I asked.
“Probably not, but I wasn’t ready last time and he fucked it anyway.” She sighed, “I was hoping for another good fucking today. Not to get raped again.”
“Mind if I check if I read your history with him?” I asked.
“Go for it.” Courtney granted. “I was planning on sending you all the nudes anyway.”
“Man, this guy is a piece of work. Isn’t he?” I said, carefully typing on my lap. “Oh, he just sent another message.”
“What did he say…’If I see your new boyfriend hanging around, I go straight to the honor office and have fun getting out of the handcuffs’. Damn it. I wasn’t going to try for that yet… wait, did he call you my boyfriend?” Courtney asked.
“Yeah, he did. I mean, I wouldn’t mind, but if word gets back to your dad that you’re calling your tutor your boyfriend, what would he do?” I wondered.
“Probably give you a raise and try to get you a position at his company when you graduate.” She muttered, deep in thought.
I chuckled nervously.
“I mean, I trust you and I love getting fucked by you. But I want to get to know you better before we give titles like that.” Courtney decided.
“So maybe we should go out to dinner next time you have a night that he isn’t demanding your ass?” I asked.
“Did you just ask me on a date?” Courtney laughed.
“Well, yeah.” I confirmed.
She giggled. “I’d like that.”
I smiled and said, “It’s a date then, what are you gonna tell him?”
“Say ‘I wouldn’t dare’. Then let’s get back to this.” She decided, motioning to the work.