Too Good To Be True Ch. 02

Courtney sighed, rolling a lock of her hair in her hands, "Well, I pretty much have to do what he wants, and I get there feeling he's going to be rough and mean either way. So I might as well get the satisfaction of making it not fun for him and pissing him off. Maybe he'll lose interest and forget about me?"

I shook my head, "Doesn't sound likely to me." I thought for a moment, "Do you know any kinks he's into?"

She once again subconsciously rubbed her ass, "He likes anal. He likes bondage. And he likes being rough."

I winced for her, admittedly I hadn't been the kindest when I started my process with her, but I didn't think I was that bad.

She thought again, "He also likes making me take dirty pictures of myself, especially when I'm out in public."

I tried my best to imagine a random dude that would like those things... It wasn't hard as I imagined myself to be pretty normal.

"I guess I could see that. He seems to have a thing about control." I mused.

Courtney rolled her eyes, "You can say that again."

"I'm no psychologist, so I'm not going to speculate on things I'm probably wrong about anyway." I told her, "All I can do is say, as your average guy, what would work on me and how I'd react. I have no idea if your bet man is anything like me, but I can plan with you. I'm going to assume he's smart because he got you to bet your body to him... no, I won't pry, you didn't want to talk about it. So I'm going to start with a question, if you succeed in pissing off your bet guy, what's the worst thing he could do to you?"

She shuddered, "Well, since I kinda have to let him do what he wants... He could do anything. I don't think he'd do anything that would actually hurt me... or he probably would have already, but I... I don't think there's anything below that asshole."

I grimaced. Her assessment of me was brutal, and in all fairness, I was blackmailing her for sex. But I didn't really want to ruin her future, just make her actually pay for it, and since she wasn't paying the price with her brain like the rest of us were, I decided to make her pay for it with her body. Okay, and she was hot, and since she wasn't a slut it meant she was less likely to end up fucking a dozen guys on me. At least, i hoped. I was kinda enforcing it with the blackmail right now, The freaking luck of her picking me to deflower her was a major bonus.

"Yeah," She sighed, "I don't like the idea either. So tell me, what are the worst things you can think of a guy could do to a girl?"

"Well, in all fairness, almost anything a guy can do to a girl, there is a girl somewhere who gets turned on by it." I admitted. "I am not generally into porn, something about knowing the girls have probably fucked more people than I have ever met turns me off."

Courtney rolled her eyes, "Thank god. I can't stand assholes who just want to pound pussy, doesn't matter how easy the slut is. It's why I always made a fuss whenever anyone tried telling me that I needed to loosen up. I don't want to be a loose woman. I don't want to be a slut, I hate sluts." Then she looked down at her naked body, and chuckled, "Though having fucked you, it's now strangely easy for me to be okay with you seeing me naked, and..." she looked at me with a lusty look, "the idea of you doing more to me turns me on." She leaned in close to my ear, the naked flesh of her tit rubbing my arm. "So what's the dirtiest thing you can think of to do to me?"

My body gave me a bit of help.

"Right now, the dirtiest thing I can think of is slamming my dick in any of your holes and letting the pee, that so badly wants out of me, out in you." I admitted, my dick hardening at the thought.

Courtney actually moaned, "Oh, yes. That asshole would treat me like a human urinal." She looked in my eyes with blatant lust, "And I'd rather you did it first." Then she looked around at her bed. "I'd better get like, a waterproof mattress topper."

She turned back to me, "So, which of my holes would an asshole want to piss in first."

"Maybe it's just that I've had your pussy, but I'd want to fill your ass with my piss." I told her bluntly, "And you said he has a thing for anal."

She nodded, "Yeah, he had fun with my ass, at least he used lube. I had to google to figure out what the slime was he put in my ass first, but that's one reason I think he doesn't want to hurt me. If he had wanted to hurt me, he'd have just fucked my ass raw. From what I saw online, that really hurts." And she opened a drawer on her bedside table, revealing her birth control and a tube of lube, among other things.

She grabbed the lube and took my hand, "Follow me."

She led me into her bathroom, threw a folded towel down in her bathtub and knelt on it. She handed me the lube and said, "I want to see what good anal sex feels like, and remember, when you are done, I need to be prepared for him pissing in me, so have fun."

I could have pierced a steel plate with how hard my dick was as she lifted her ass and spread her cheeks for me, and she didn't have to ask twice. I set her phone, camera still open, on the toilet. "Relax your ass." I told her, as I popped the top of the lube and applied a dollop to her lovely pink pucker.

"Oh, that's cold." She gasped.

"It'll warm up." I told her and then slid my pointer finger into the puckered star of her anus.

The difference between when I had basically ass-raped her and now was night and day. Where before I had to force my way into her ass, now it almost welcomed me. It was enough I was two knuckles in before I realized it. I didn't want to slam her like I had when I deflowered her pussy, so I started working her as I lubed her puckered asshole.

"Ohhhhh..." She moaned, "You are so much better at that."

"I'm going to add a second finger," I warned her, "I need to loosen you up or my dick will hurt."

She smirked, "I was aware of that. But thanks for the waaaaaaaarning." She moaned as my second finger joined the first. I noticed that this was obviously turning her on, as she almost had a river of new vaginal fluid, mixed with cum and a touch of blood, running down her leg.

I smiled and stuck my thumb in her hungry pussy and started pumping both holes at once.

"Fuuuuuuuck!" She groaned, quivering. "Get your dick in my ass before I lose my mind, I need to feel it." She smiled back at me, "I appreciate you making this great for me, but I need to know what it'll be like rough."

I conceded, and put a dollop of lube on my dick, and spread it out.

She lifted her ass again, spreading her ass more eagerly.

I placed my dick on her star and gently pressed forward.

"Mmmmfft." She groaned as her ass gently let my phallic intruder in.

"God, you are so much bigger than him." She gasped.

I found that doubtful, but just groaned in appreciation of the tight ass that was now wrapped around the head of my dick.

"Okay, you are being too gentle. Stick it in all the way." Courtney instructed, trying to stay loose and mostly succeeding.

"Alright..." I grudgingly accepted.

I leaned in and pushed hard. The sensation of going from barely in to bottoming out in her ass was amazing.

"FUCK!" Courtney shrieked.

I obeyed. Pulling back until just the tip was still in and then slammed in again.

"Ohhhhhhh....." Courtney squealed as her ass got hammered.

"Your ass is amazing....." I breathed as I continued to ram her ass, "I won't last long."

"Good, enjoy it while you can." She taunted, then reached forward grabbing the front edge of the tub, pushing back into me, "Fuuuuuuuuuuuck!" She groaned as an orgasm hit her.

Her orgasm caused her ass to clench and milk my dick. Which felt amazing as I continued to pound her.

True to my word, five pumps later my dick gave me the sign it was about to fire round two. I grabbed her phone, started a video and pointed the camera at her ass with my dick pistoning in and out. Lube glistening around her yawning asshole in the bathroom lighting. I plunged in as deep as I could and erupted.

"God.... I could get used to this." Courtney breathed, lifting her ass as if begging for more sperm in her ass.

I didn't have as much spunk to dump in her ass as I had in her pussy. But it felt amazing. I kept videoing as I eased out a bit then pushed back in.

"Mmmmmmmmmph." She moaned.

"Ready? If I am gonna pee it's gonna be now." I asked, feeling the need to relieve myself rising and knowing I had to do it quickly or her spasming ass would push my softening dick out.

"Do it." She instructed.

I let loose. Pee streaming into her ass, mixing with my sperm and all the bits already in her ass. I felt her sphincter tighten around the base of my dick, holding the torrent of piss inside her hot lubed ass.

"God, I feel it. It's so warm." Courtney breathed, "So full....I can't hold it."

And with that, liquid began to leak around my dick, clearly visible to the phone camera pointed at her ass. A moment later the flood came as I continued to piss. The light yellow liquid with globs of sperm and flecks of fecal matter swirled around my dick and down her legs.

Courtney shuddered with a smaller orgasm as my bladder reached the end of its supply. "It felt like one giant squirt of your sperm." She breathed, lifting her head, so the bit of mixed fluids that wasn't absorbed by the towel she was kneeling on ran past her face and down the drain of the bathtub.

I pulled my dick from her ass, and continued to video as her ass pushed the majority of my deposits out of her bowels.

Courtney turned her head toward me, and noticed the phone obviously recording a video. She smiled and wiggled her ass for the camera, pushing more liquid out. "That is how you fuck an ass." She smirked.

I hit the button to end the video.

"When did you start recording?" She asked.

"Just before I came in your ass." I admitted. "I hope you don't mind."

"Oh, I'm thrilled you did it." She exalted. "If that asshole thinks him pissing in me will be the first time, I'm going to send that video to him and laugh as his dick shrivels."

I wished I hadn't just cum so my dick could show how much it turned me on, the thought of her sending a video of me fucking her ass to myself to try to "own" me.

I stood and moved away from her so Courtney could get up.

"Wait." Courtney instructed, sitting on the edge of her tub and pulling up the towel she was kneeling on to clean the little bit of shit off my dick. "Wouldn't want you making a mess." She explained, then started wiping herself off with a clean section of towel. She lifted the toilet lid and sat on the toilet, relieving herself in front of me.

I can't tell you how hot it was to hear her bowels evacuate the last bits of the fluids I had just pumped up her ass. Even her peeing was a turn on, especially after me having just pissed in her.

"Well, I need a shower..... Care to join me?" She asked.