“Pa-leeze, ask almost any guy you want and you could do it tomorrow.” I snorted with snide derision.
“That’s not a lot of time for such a big decision…” she whined.
“Fine, I’ll give you two weeks. But I still want your pussy to be nice and tight. I’m keeping an eye on you and if you fuck more than one guy, I’m dumping every picture you’ve sent me on every porn site I can find and sending my evidence to the honor office.”
“This is ridiculous! I have two weeks to find my husband? How-” she started.
“Oh, I doubt you’ll marry the dude you fuck. You aren’t gonna get to only fuck me and the one guy you finally marry. That stopped being a real option when I caught you cheating. I mean you could get lucky, but your luck hasn’t been great up until this point. Has it? No, you just get to find the guy you can deal with being your first fuck. You’ve got two weeks. Or I can just do it now. Your call. What’ll it be?”
Her head looked away. “Not now.”
“Okay, then I’ll just fuck your ass now, and you’ll have two weeks to find a dude you can deal with. Then I’ll get my turn. Remember though, if you don’t find a guy, I’m still fucking you in two weeks. Or you can flush your college career down the drain. Oh, and when you get fucked, I want pictures. Full body nude. Sperm dripping from you. At least a dozen.”
“Bastard….” Courtney breathed.
“I’m not the brainless, cheating bitch. Ready to get your ass fucked?”
“Please be gentle, I’ve never put anything other than my finger in… in my ass.” She begged again, “Don’t hurt me.”
In response, my second pussy soaked finger went in her ass.
“Fucking damn it!” She cursed, “what did I just say?”
I just laughed, “This is me being nice. Getting you nice and stretched before putting this in.” And with that, I slapped my dick up on her pelvis. Now, I’m no 12 inch monster, but I’m six inches when I get this horny, and not small girth.
It took her a second to realize what was sitting inches from her vagina and ass, while I was fingering her ass. But her nipples hardened and within a few seconds her vagina started dripping onto my fingers as they moved around and in and out of her ass. She gasped, “It won’t fit. You’re gonna rip my ass apart!”
“Might feel that way for a bit, but I doubt you’ll rip and that’s gonna feel so good.” I told her, “Heck, if you’re lucky you might get your first orgasm.”
Try as she might to deny what her body was feeling, she was breathing hard when she said, “I doubt that.”
I started pulling over the tube of lube I’d bought for the occasion, and generously applied it to my dick, then to her asshole, using my fingers to work out deep in her ass. I knew from my ex-girlfriend it wasn’t as much fun for either party fucking a dry and angry ass. I worked up to a bit of a frenzy, my fingers pumping in and out of her tight asshole while her breathing got more and more ragged and fast.
Her body started twitching a little. I knew from my previous girlfriend that she was about to have a body rocking orgasm. So I took advantage and started rubbing her clit with my thumb. Only a moment of that and she was pushed over the edge. I pulled my fingers out of her tender asshole and while she was twitching, pressed my duck’s head against the sweet pucker of her ass and pushed. A combination of a well lubed anus, a well lubed dick and a horny thrust that honestly was a little harder than necessary popped my dick right past her sphincter before she could comprehend what was happening. Her body shook a few times, her body tensing up from the orgasm. It took everything I had to not instantly blow my load in her ass.
As her orgasm faded, she twisted, trying to pull off my dick. “That hurts.” She complained, killing a lot of the swelling feeling in my balls.
I smiled, if she’d kept her mouth shut I could have lasted another ten seconds, tops. Now I’d get a nice long ass fuck. “You’ll get used to it.” I told her and began thrusting.
I wiped my hands off on the sheets and started groping her fabulous tits as my dick pistoned in and out of her ass. Her ass pulsed and spasmed, probably trying to push me out, but only succeeding in massaging the rod assaulting her bowels. I’d like to say I lasted for minutes, but it was probably a minute, two at most before I squeezed her tits good, thrust as deep as I could in her ass and dumped as much sperm as I could. Apparently, I lasted long enough, because Courtney’s back arched and her body shook with another orgasm.
I gave her tits one last squeeze, then pulled my dick out, wiping the little bit of shit from her ass off on her sheets. I admired my work for a moment before I grabbed my phone and took a few pictures. I even did a video for a second to get good angles, and was lucky enough to video the first glob of my semen dripping from her ass. I decided to be content with that, and started getting dressed.
I guess Courtney finally gathered her wits as I was pulling on my shirt.
“You gonna let me out now? I need to pee.” Courtney demanded.
I took a loop of fishing line, tied one end to one of the handcuff keys, made a loop I could tighten around her finger. As I secured that end to her finger, so it wouldn’t fall off, but not tight enough to cut off circulation, I told her, “On the other end of this string is one of the keys to your handcuffs. Pulling the strings will give me time to get out of your house and where you won’t be able to find me, then you’ll be able to unlock yourself.”
“Fuck you.” She snapped.
“You will.” I told her. “With your pussy in two weeks, maybe again with your ass in the meantime. That was great.” Then seeing she was already working to get her key, I left. Resetting the video call so I could be sure she got unlocked okay, and locking the door handle behind me.
I was down the walk and two doors down when she got the first handcuff off. I guess she was telling the truth because she immediately freed herself, then ran from the room. When she came back, I got to watch her for a minute, as she looked at her asshole in the mirror, then looked in frustration at smears on her bed. Then she noticed the video call was still going and ended it.
I was feeling pretty good when I got home. I’d just fucked Courtney in the ass and in two weeks I’d get to fuck her pussy. I was a little bummed I wouldn’t be the one to pop her cherry, but at least I’d get to fuck her, and boy did I plan on fucking her a lot. I’d seen her birth control on her bedside table, so I knew I didn’t even need condoms. She had another year and a half until graduation and she was gonna fuck me the whole time. Things were looking up.