740

Her house was a single floor unit, no streetlights nearby and shrubbery blocking view of the house. I couldn’t ask for a better house to sneak up to.
Over the next week, my phone storage filled with pictures of her tits, pussy, and ass. Boy, I could hardly wait. Sometimes I felt bad, like the time I made her leave class, go to the bathroom, take a picture of her pussy, then come back to class and send me a picture of her panties, to show she wasn’t wearing them. After a while she stopped trying to argue against the next lewd photo.
I knew I need to be careful here. I started keeping all the photos of her on an extra SD that I encrypted and programmed to start immediately formatting itself if decryption failed. But I decided I couldn’t just see anymore, and I was tired of jacking off. I headed home to work out the rest of my plan.
The next day was a Thursday, after work and class was done, I closed myself in my room and booted up my desktop. A message was then sent to Courtney.
“Good afternoon. Today you have two tasks, complete the first and then I’ll give you the second. Your first task is to go to any of the sex shops nearby, you can choose which one, and you are to buy: a blindfold, and 4 pairs of padded handcuffs. Then return home.”
Her reply came, “How the hell would I know where any sex shops are!?”
I replied, “Come on, you can Google.”
An hour later, she replied. “Fine, you sick bastard. I’m done.”
“Send me a picture of your purchases on your bed.”
A moment later a picture of a simple black blindfold, and four pairs of pink padded handcuffs appeared. “Happy, you sicko. I can’t believe you made me go there.”
“Indeed. I am happy. Now, your second task. Send me a picture of your vagina and asshole.”
She replied almost instantly, “No! I’m sick of doing everything you ask! I’ve given you more then enough pictures. Leave me alone!”
I was getting tired of this.
“Apparently, you have forgotten how this works. I tell you what to do, and you do it. No complaining. No moaning. You don’t get to object. If you don’t start just doing as you’re told, you will be getting expelled. Have I made myself clear?”
It took a long time for her to reply.
“Yes”
“Now, I was going to be happy with one picture now you owe me three. Lay naked on your bed. Spread your legs and send me a picture of your asshole and vagina. Then I’ll tell you what you have to do for your extra pictures.”
She didn’t reply for almost ten minutes, I was just about ready to send her another message, but then it came. She actually did better than I’d hoped. Apparently, she’d struggled with the angle and had ended up putting her ankles behind her shoulders to get the picture. I could tell because of the way her hips were. Man, was she flexible. I vowed to take advantage of that.
Her vagina was perfect. From the number of pictures I had I new she had done laser hair removal. There was never hair or even stubble around her precious cunt. There was even a slight glistening that told me, whether she liked it or not, this turned her on. Her asshole was equally beautiful. I loved anal sex and that asshole had my name on it.
“For your next picture, spread your vagina as wide as you can with one hand and take a close up.”
This picture came much quicker.
“For your final picture, unless you try to object, you will insert your pointer finger in your asshole, as deep as it can go. I expect at least two knuckles. Then send me a picture of it.”
This picture took longer, but there it was.
“Fuck you” was all she said with it.
The following day work crawled by, finally the work day was done. Instead of going home, I went and waited about a block from Courtney’s house.
“Hello Courtney, send me a picture of where you are.”
A moment later I got a selfie of a grumpy looking Courtney in her kitchen.
“Strip. Then send me a photo.”
A few minutes later, a photo of a naked Courtney in her kitchen.
“Go to your bedroom, get out the blindfold and handcuffs, then start a video call.” I started walking toward her place. The street was empty, thus it was perfect. When the video call started, I turned off my camera before joining. A naked grumpy Courtney held up the handcuffs and blindfold.
“See? Happy?”
I contorted my voice, hoping she wouldn’t recognize me. “Each pair of handcuffs came with 2 keys, correct?”
“Yeah.” She huffed
“Show them to me.”
She held them up.
“Prop your phone so it’s pointed at your bed, then put all the keys on the table in front of your phone. Then climb on your bed with the blindfold and handcuffs.”
She made a face then compiled.
“Put one pair of handcuffs on each of your arms, then each of your ankles.”
“You have some weird kinks. Naked dances with chains.” But she did it.
“Now, attach the other end of your left ankle handcuff to the left column of your headboard. Then do the same for your right leg.”
Her face was suspicious. But she complied, with some struggle.
Oh glory, I almost came in my pants. She looked so sexy chained to the bed, but I wasn’t done yet. I started up the walk to the house she was staying in.
“Put the blindfold on.”
She did.
“Now handcuff your left wrist to the column like your left leg is.”
Her suspicion was clearly growing but she complied.
“Now do your right wrist the same way.”
She faltered, “But I’ll be stuck…”
“Do it.”
“Fine, but you better know how to get me out.” And with great difficulty and some straining, she got it latched.
I checked the doorknob. She hadn’t locked it. I probably could have picked the lock, I’d taken up lock picking a few years ago, but this made things easier.
As I opened the door, I watched on the video as Courtney, naked, blindfolded and handcuffed, heard her front door open and tried to sit up.
“What the fuck?” Courtney exclaimed.
“Relax, it’s just me.” I told her, walking back to where the bedroom clearly would be.
“What part of that should make me relax?” She exclaimed.
“Calm down. If you make too much noise I’ll leave you handcuffed to your bed and you can scream until the police come and let you out. All the cops in the area are men. But I suppose if you want a bunch of men seeing you naked, you could have just told me. I’d have posted all those photos you sent me.” I said as I walked in the room.
Damn. I thought the sight of her naked, blindfolded and handcuffed had been hot on the video call, well, it was hotter in real life. The bitch had a king sized bed all to herself. The headboard was big enough she could barely move with her arms and legs stretched and handcuffed to the supports at each end.
I didn’t end the call, but pointed her phone camera down into the dresser it was sitting on.
“What are you gonna do?” Courtney demanded trying not to sound scared as I looked for any hidden cameras. Hey, studying cyber security made me a little paranoid.
Satisfied, I took off my shirt and started to take off my pants. “Oh, I should think that would be obvious.” I stated, then just to emphasize the point I reached over and ran my hand from the top of her vaginal lips to the base. She was soaked. Like if or not, this turned her on.
“Please,” she begged, starting to cry, “don’t do this. I don’t want to lose my virginity this way…”
Part of me felt for her enough in that moment, I knew I would struggle and I’d feel horrible if I fucked her like this. She was sitting there, turned on out of her mind, but at the same time terrified and begging to keep her virginity. I had an idea.
“I don’t see how you didn’t see this coming, but I’ll chalk it up to naivety. I offer you a compromise.” I said, still rubbing up and down her vagina’s lips, getting her love juices all over those fingers, “I will give you a week to find another guy and lose your virginity on your own terms, and in exchange today… I’ll fuck this.” And with that my finger slick with her pussy juices slid right into her unsuspecting ass.
‘She flinched at the unexpected anal intrusion, as she had a fair amount of slack in her handcuffs, “Fuck, that hurts! You should warn me first. Ow….”
“Do we have a deal?”
She squirmed, I couldn’t tell if it was my finger which I was lightly twirling in her ass, or the offer. “Could you stop moving that down there?” She snapped, then she said “What if I can’t find a guy?”