Too Good To Be True Ch. 05

Chapter 5

At 7 pm, Courtney said she needed some time before her blackmailer showed up and wanted me safely gone before he showed up. I told her I'd see her in class tomorrow and headed out. I went home gathered my bag with lube and other things for fucking Courtney, and headed back. At 10 minutes to 8 pm, Courtney started the video call. She was already naked, sitting on the bed. She had changed the sheets again, the cheap white sheets replaced her nice pink ones.

"You can cuff yourself, I'll be there as soon as you're restrained." I informed her.

She flipped off the phone, lowered the blindfold and started cuffing herself like last time. When the last one clicked, I opened the door.

I walked into her bedroom, moving her phone to make sure I wasn't in the video, and admired the view. Her bald pussy glistening under her lights. After shedding my clothes, I quietly walked over and to introduce myself I inserted my thumb in her pussy.

She gasped, "Warning would be nice!"

"Oh, but you're already so wet." I said in my contorted voice, "You knew it was coming and knowing when would just ruin the tension." I said, starting to rub my thumb on the top of her vagina, finding the bumps that indicated the location of her G-spot. I began rubbing.

"Just get it over with." She muttered.

"Oh, I plan to enjoy myself. You can pretend you aren't, but your pussy is sopping wet. Making lots of lube for me to loosen your ass with." I gloated. It was kinda hot knowing that if she knew it was me, she might very well just tell me to fuck her in whatever hole I wanted. I drew my thumb from her pussy and gently pressed the soaked digit into her puckered ass.

She grunted as the intruding thumb pressed past her sphincter. I watched her nipples harden as she couldn't help getting turned on. I reached up with my other hand and twisted her nipple, hard enough to shock her, but not hard enough to actually be painful.

"Ow!" She complained, but a rush of vaginal fluid told me she liked it.

I leaned down and lightly bit on her other nipple, forcing a moan out of her. I started playing with her clit with my finger as my thumb started stretching out her ass.

"Stop... trying... to.... make... this... feel... good.... I'm... never... gonna... like... it..." she said, then her back arched in an orgasm.

"Your body is enjoying it, and it is easy to see." I disagreed. I retrieved the lube and began applying it to the thumb that was now pistoning her ass.

"Fuck... you..." she breathed through the stimulation.

"Great idea." I said, quickly pulling my thumb out and putting my dick at her entrance.

"I'm not ready!" She gasped.

"Too bad," I said, and with a quick thrust, my head was buried in her ass, but I was merciful and only got about an inch in.

Courtney grimaced, and I started slowly pumping, putting my lube on my rod as it speared her bowels. After about 5 thrusts I was all the way in.

It was interesting, being able to compare the sensation of her relaxing and willingly taking my dick up her butt earlier and her struggling now. I knew she could handle it, but the way her ass was pushing back on me told me she wasn't relaxing and it was more intense at least for me. And after just a few minutes, I drove deep in and came hard.

Feeling me shoot my sperm in her so fast, I swear she smiled for a second, triumphantly, but quickly hid it.

"I'm gonna take a shit, then I'll be back for round two." I informed her.

"Let me out, I'll cramp like this." She begged.

"Then you should hope I don't take too long." I told her.

I did need to shit, and shit I did. I was also debating, and upon returning, seeing the sperm dripping from her ass as she squirmed to get comfortable, my dick made the decision for me.

I announced my return by slapping her ass.

"Mmph!" She grunted, "You could just say you're back like a normal person."

"Oh, but neither of us are normal." I told her, "You were the Virgin Cocktease Cheater and I'm the stud smart enough to catch you." Okay, it had been pure luck and I'd been perving on her, but she didn't know that.

"Just fuck my ass again and be done with it." She snapped.

"Oh, I thought we could move past that. After all, your boyfriend has had this twice now. I'm thinking it's my turn." I told her, rubbing my thumb up and down the slit of her pussy. Damn, she was so wet. I could probably bottom out in one thrust, no problem.

"You said you wouldn't fuck me there for two weeks!" She cried out desperately.

"No, I told you if you hadn't found a man to fuck your pussy in two weeks I'd fuck it and take your virginity. I never said that if you went out the next day, like a cheap whore and fucked the first guy you found id still leave it alone." I corrected, and stuck my thumb back in. "And with those pictures as proof, you have no reason to deny me my prize. But look at the bright side, you'll get to fuck your pathetic boyfriend again."

She was torn. I could see the arguments in her head. She had hoped to get lots of my dick in her pussy before the "blackmailer" got it. But that had been shut down, so she couldn't go for that. And she did want to be able to take my dick again.

"You should feel honored I'm not just fucking you like the cheap whore you are. I'm actually giving you a choice. Let me pound that sweet, near virgin pussy, or only let your boyfriend fuck your ass and mouth." I told her, rubbing her g-spot some more.

"Fine, asshole." She told me.

"No, this is the asshole..." I told her, pulling my thumb out and driving it all the way in her ass, making her gasp and squirm.

I pulled my thumb out of her ass and lined my penis up with her love hole. As I guessed, one smooth thrust and I was balls deep in her pussy. "And this is your pussy."

"Fuck!" She gasped. There was probably a little pain, but I'd make it up to her next time I fucked her... not as a blackmailer. Right now I was just slamming into her with wild abandon. Her pussy felt so tight with her ankles back by her head. I swear my dick was touching her womb as it slammed home.

I might have been in it for me, but Courtney came first. Thrashing and moaning as her body spammed before the onslaught of my cock.

"Stop, stop, I need to pee!" She begged.

"Ha!" I laughed, I knew from my first girlfriend what was gonna happen. When a girl thinks they're gonna pee during sex, it usually means she was gonna squirt. Oh, part of me felt bad that her first squirt was going to be with blackmailer me, not tutor me, but in the end she was gonna squirt. "Not a chance!" I informed her and redoubled my efforts. Having fucked her multiple times earlier in the day, and cum in her ass a few minutes ago, my erection was going strong and there wasn't a climax in sight.

True to my prediction a few thrusts later, she arched her back and wriggled, trying to cope with the spasming of her body while restrained, and the moisture of her squirting bathed my cock and balls in her love juice. "No!" She moaned, tearfully.

"You don't like squirting?" I teased continuing to fuck her, highly aroused by this development.

"What do you mean?" She gasped.

"You... just... squirted... on... my... dick..." I told her, fucking her insanely lubricated and tight hole.

She quietly cried as I kept fucking her, even though her next, squirt-free orgasm and my subsequent ejaculation. I took a picture of her, covered in her ejaculation and mine, sperm still dribbling from her ass and pooling beneath her holes.

I then got cleaned up and told her, "Same as last time." And put the strings attached to the key to her handcuffs on her finger.

I was a couple of doors down, when I checked on the video, she was barely starting to try to get the key. I was worried. I had fucked her hard, but nothing that should have done this to her.

I couldn't message her as her tutor, because he wouldn't know, and messaging her as her blackmailer wouldn't help.

I got home, still worried.

"What happened, the condom break?" My roommate Sam teased me.

"Shut up. You know I'm not like that." I snapped.

"Come on dude! What's the point of going to college if you don't enjoy the perks! Find some freshmen and fuck her! You'll feel better and she'll get over you when you're done!" He counseled.

"I told you to shut up!" But that did give me an idea. I'd have to make sure to set it up right.

The next day Courtney sat next to me, obviously bothered.

"You okay?" I asked, legitimately worried.

She shrugged. "We'll talk later."

Class dragged on, but finally it was done and we headed to Courtney's place.

"Okay, what's up?" I asked, once we were inside, "Did he hurt you?"

Sobbing Courtney threw herself against my chest. I held her, unsure how to go on.

"I'm a slut." She gasped, finally.

"What?" I pressed.

"He fucked my ass like we knew he would, and.... I liked it. Then he offered me a deal, since I wasn't a virgin anymore he didn't have to wait to fuck my pussy anymore and... that would mean you could fuck me again... so I let him. And... It was amazing. I... I...I even squirted on his dick! I thought I had to pee, I begged him to stop and he kept going! Then I had an orgasm and it was like I was peeing and wasn't at the same time." She explained, still clinging to my chest and crying. "It felt so good! I hate that the beat sex I've had was getting raped! I mean, we've fucked twice, but it was better with him... why am I such a slut? To like getting raped!?" And she got quiet, but I could feel her tears through my shirt.

I realized what was going on. "I have an idea." I declared.

She looked up at me hopefully.

"You said it was the most amazing sex you've had. Right?" I pressed.

She nodded, not encouraged.

"What if it wasn't him? What if it was just the position and other circumstances? You knew he was going to fuck you for hours! And I bet that you thought you were going to be better than he was expecting and you were going to turn the tables on him. I bet that's what turned you on. Then, you said you were handcuffed last time and he told you to do that again. I've only fucked you with your legs around me, not restrained over your head. That's an entire other kink that could have turned you on. There's a reason they sell handcuffs at sex shops. Same thing with the blindfold." I told her.

She looked hopeful, but not convinced.

"Here's my plan." I told her. "We'll do another study session today. But you will be sitting next to me, with my hand up your skirt, fingering you, until 6 o'clock. You won't be allowed to get any other satisfaction until then. At that point, we'll take you into your room and handcuff you to your bed, blindfold you and I'll fuck you senseless. I'm betting you'll cum. I'm betting you'll squirt and I'm guessing it'll be better than getting raped."

By the time I finished, she was biting her lips and squeezing her legs together under her skirt. "That's not fair." She moaned. "I want it now."

"But we're trying to prove you aren't some easy slut who came just because she got raped." I reminded her. "By keeping you hot and horny, like you were yesterday, and then replicating the situation that led to the squirting orgasm, I am betting you will have an orgasim twice as good."

"Fuck... Why do I have to wait?" She begged. "And you said you're going to be playing with my pussy the entire... 4 hours... that's torture!"

"You'll like it." I promised.

I admit, my fingers got tired multiple times, running up and down her slit, slipping in her love hole and keeping her on edge. It was probably not the most productive study session, but it was fun having my hand up her skirt and watching her twitch. Even through her bra I could see her nipples like little arrowheads poking through her shirt.

Finally she could wait no more, "It is 5:55. By the time I am naked and cuffed it will be 6. Let's go!" And with that she was heading down the hall. Shirt, bra and skirt were shed before she got halfway down the hall. My clothing landed on top of hers.

She flung the handcuffs and blindfold on the bed, climbed on and started getting her wrists and ankles cuffed. I helped her cuff her ankles, then her wrists to the bed. I stepped back to admire her restrained nakedness. I doubted I would ever get tired of that naked body. "Damn." I smiled.

"Yes, I am sure it is hot. Now blindfold me and fuck me!" She begged.

I climbed on the bed with her, and pulled the blindfold over her eyes.

"I am betting, he didn't just stick it in. In fact, you said earlier he fucked your ass first." I told her.

"Fuck my pussy! Please!" Courtney begged. "I need your dick! I need it in me!"

I leaned down and licked her pussy, slowly from bottom to top.

"Oh... You fucking tease." She moaned.

I took my dick and began to rub it up and down her slit. It was sopping. Just touching it to her slit it almost slipped in.

She moaned and shivered, "Please just fuck me!"

"Your wish..." I whispered, and thrust my dick between the folds of her womanhood. As wet as she was, I sunk in balls deep with no effort, her love tunnel shuddered and gripped my cock, and pulsed. "... is my command."

"FUUUUUUCK!" She moaned, arching her back as my penetration drove her over the edge she had been at all afternoon. Her vagina spasmed and pulsed around my cock.

I put my plan into motion, literally. I began thrusting vigorously, latching onto one of her nipples with my mouth and mauling her other boob with my left hand, while my right hand dove to her clit, which I had been avoiding all afternoon. I sucked as much boob into my mouth as I could and began doing circles on her nipple with my tongue.

While still pulsing from her first orgasm, her body redoubled its thrashing and my goal was achieved. Courtney's vagina gushed a stream of her ejaculate fluids. Courtney's mouth opened but only a hoarse squeak escaped.

I wasn't done however, and kept my pace. Driving my pulsing dick into her raging love tunnel as fast as I could, while I ran circles on her clit with my fingers, mauled one boob and suckled and sucked on the other.

Moments later, as Courtney's body tried to come down from the mind shattering orgasm she just experienced, her body convulsed again, gushing a second smaller rush of her fluids. Courtney finally found her voice and screamed, "Fucking GOD!!!" And she continued to thrash as I stayed latched to her body, fucking her with purpose and vigor.

Moments later, she recovered somewhat and cried, "YES! MORE! DON'T STOP!!"

I kept at it, feeling the beginnings of my climax rising. Part of me wanted to pull out and try to keep this going, but having been playing with her hot pussy for hours had an effect on me too, hence my quick buildup. I decided, fuck it, and kept pounding until I couldn't hold it anymore and unleashed to torrent of my sperm, continuing to pump into her vagina as I did so.

The rush of my sperm hitting her cervix combined with everything else to push her into another explosive orgasm, a third final hush of vaginal fluids, seeming to reach the ends of the fluids available was the smallest squirt but a third nonetheless. Courtney's body seized up, and she gasped for air, before falling back.

"No more." She gasped, "I... can't... anymore."

I relaxed on top of her, releasing her nipples and just enjoying the sensation of her vagina pulsing around my softening dick.

"God... oh, fucking God. Tom..." She breathed, shuddering. "Please, I need to hold you." I grabbed the key and released her right hand first, which immediately wrapped around me and clung on for dear life as I freed her remaining limbs.

I flopped on the bed half on top of her as she clung to me with arms and legs. She continued to shudder then I felt wetness where her cheek was pressed into my chest.

"Are you crying?" I asked, concerned.

Courtney nodded.

"Are you okay?" I pressed, more concerned.

Courtney nodded more vigorously. She tried to speak, but sobbed.

I held her as she sobbed into my shoulder for a moment, feeling concerned and feeling like the worst human ever.

"Thank you... thank you, Tom." She finally gasped. "I've never been so happy. It's so stupid I'm crying, but I can't stop it."

I felt a little better, "Happy tears are okay. Want to talk about it?"

"I've never had anything like we have." She explained tearfully. "Mom had me because dad wanted an heir, but she hated what having me did to her body and I think she has been careful to make sure I never had siblings, no matter what she told dad. She never was around. I had nurses and nannies, but they were there for the money and I knew it. They might have felt bad for me, but they never loved me. Dad was always working or on a business trip."

"I've never felt loved like I do with you. I don't understand it. A week ago, you were just a smart, cute guy in a lot of my classes, and now, I'm terrified to lose you." She clung tighter. "I'm so grateful to the asshole who's blackmailing me. I'd never have given you the time of day without him."

She snorted, a sort of crying laugh. "Though I wish he'd stop fucking me already and just let me fuck you." She loosened a bit. "Please don't leave me."

"I won't." I told her. Part of me desperately wanted to reveal her whole thing. That I was her blackmailer, that I'd still been the only man to touch her... But I couldn't believe she'd forgive me. The truth would crush her. Maybe someday I'd tell her, but I couldn't now. She was too delicate. But I had to find a way forward that didn't involve her submitting herself sexually to her 'unknown' blackmailer.

"Promise?" She begged desperately.

"I promise. I won't leave you unless you tell me too." I told her, "And I hope someday you can see me for who I am and still love me for it. I'm not perfect. I'm not even great. You just chose a guy who's good in bed."

"And smart, and willing to tutor me!" She piped up in my defense.

"Yeah, I'm not sure accepting over double my previous paycheck to teach you, while spending an equal amount of time fucking you, qualifies me as a good person." I pointed out.

"You didn't start blackmailing me when I told you." She stubbornly insisted.

I laughed, "What would I have asked for? You're already giving me sex and money?"

"Oh." She thought. "Doesn't matter. You didn't judge me, and when I told you I was a cheap slut, you proved me wrong. I know you have your reasons for not pursuing other girls. Fuck, if the rest of the girls on campus knew what your dick could make them feel, I'd have to hire security to beat them away with sticks!"

"Well, we'll see how long your opinion of me stays good. My last relationship was great until my girlfriend decided I wasn't worth being faithful to." I told her.

"What happened?" She prodded, obviously aware this was a sore subject for me.

"We dated for three years in high school. We figured out how to have great sex together. We were making plans for after high school, we were gonna get married, go to college, start a family... then I was ten minutes late to a party and found her in a back room, deepthroating the quarterback, while the tight end fucked her ass and the running back fucked her pussy. She'd already fucked four other members of our football team and half of the rest of the team was lining yo for their turn." I seethed.

"Wow," Courtney gasped, "that's a slut to be sure."

"Yep, and one hell of a way to find out. She wasn't even drunk." I vented, "I thought I knew her. By the end of the school year, rumor was she had a couple of STDs and was pregnant with no idea who the father was."

"I'm so sorry she did that to you. What a stupid bitch." Courtney lamented.

"I decided I wasn't going to have sex with anyone who didn't have serious standards after that. Which kinda left virgins... and it isn't most days a virgin comes up to you, begging you to deflower them and then offering to exclusively fuck you." I told her, "I don't hold the blackmail shit against you, obviously it's not your fault. That's way different from backstabbing me like Nikki did."