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.