I threw two pairs of cuffs behind me onto her lap in the back seat. In stunned silence, she put the ankle cuffs on right above the high heels she would have been wearing to the dance. In the rear view mirror as she did this, I saw up her dress and caught a glimpse of her black lacy underwear while she was lifting her feet messing with the ankle restraints. I would be seeing a lot more in a few minutes. She put on the handcuffs and was silent for the rest of the drive. Smart girl, she knew how to follow directions.
When we got back to my place, I parked the car in the garage and closed the garage door. I got out, went around, flung open her door, reached down, grabbed her legs, and pulled them out of the car while pushing her forward onto the seat. She gasped as her face landed into the back seat cushions, but didn’t say anything. Like this, facedown in the backseat of my car, legs hanging out of the door, and ass perfectly presented to me, I hiked up her sparkly homecoming dress to take in a gorgeous view of her legs and butt. I pulled down the little sexy underwear that I had seen earlier to reveal a tight round ass and a little mound of a cleanly shaven pussy. I guess she had been expecting to get some action tonight, but probably not like this.
I’m sure she expected me to bury my penis into her vagina, or even her ass, but first I threw my face into her pussy. Licking and exploring all around with my tongue, she gasped, shivered, and started breathing heavily. I probed her tight little cunt lips with my tongue, exploring her little folds and clit. I felt her starting to get wet, with moisture coming from her rather than my saliva. As I kept at it, I felt her start fighting against me, trying to kick or buck or push me away. I pushed on her back, my hand on her dress, holding her down to the car while putting my knees on her cuffed legs, holding them against the concrete floor of the garage, scuffing up whatever nice heels she was wearing.
Deciding that she was wet enough, and with my own erection already straining at my pants, I pulled myself free, let down my pants, and, positioning myself behind her, lined up at her opening.
At this point, even knowing my previous warnings and commands to her, she started pleading:
“Wait, please, don’t – I’ve never had a guy this way before! I swear, please, you told dad you’d take good care of me, not -”
I cut her off at this point by grabbing the back of her head (through all of the fancy hair she was wearing for the dance) and shoving her face into the cushions of the car. Her makeup would probably end up staining the seat, but I’d deal with that later. Face full of seat cushion, her words were muffled and I proceeded to insert myself inside of her.
She was incredibly warm and tight, pushing against my cock and resisting my entry. Turns out she wasn’t lying – that homecoming date hadn’t beat me to this part. I thrust in and held myself there, enjoying the moment. One hand on the small of her back (the dress was pushed up pretty high at this point, clustering just around her chest), the other still holding her head down, I started to thrust a bit quicker. She started moaning and shuddering, afraid that I would fill her tight little pussy with my cum. I pushed in and out, leaning forwards to see her face, screwed up in pain and fear. Her makeup was all messed up, and her hair wouldn’t be fit for any homecoming pictures any time soon. Getting a waft of some perfume she had on, I held her tight against me as I thrust tight into her cunt and unloaded my seed deep into her womb. She shuddered in disgust again through her whole body as I lay there on top of her, in the back seat of my car, in my dingy garage, my penis pumping cum into her. It felt very pleasurable.
Once I had spent my load, I got up, grabbed her handcuffed wrists, and led her into the house. She was having to hop weirdly in her heels with her ankles cuffed together, her underwear having fallen down, still caught on the cuffs. She started crying as she tripped and fell, tears spilling out of her eyes as semen leaked out of her pussy. I pulled her back up to her feet and dragged her to the spare bedroom. I lifted her up and threw her onto the bed. I had spent a little time preparing the room for this, and had some chains ready. I secured her wrists to the headboard then proceeded to uncuff her ankles. I secured one each to the two sides of the foot of the bed, throwing away her underwear as I did so, so she was face up, legs splayed open in an upside down “Y” position.
I left her there crying while I went and got myself some dinner.
After eating, I came back ready for a second round. The night was still young after all, and all of her friends at the dance would probably only now be hearing the news that she would not be joining them. Also, as it was Friday evening, there was still so much time left in the weekend before her father would be able to call the bank Monday morning. Things were looking up.
Looking over her body, I decided it was time to deflower her anus. I placed a pillow under her ass so her pelvic area was being presented to me, and then proceeded to remove her dress. Unzipping it out from under her proved to be a little challenging, so I got a knife to slice it down the front.
She gasped again when I pulled out the knife, and started shuddering when I got close to her chest with it, and then, visibly relieved when I started cutting the dress and not her, was almost happy to let her bra and pussy be shown to the world. I cut away her lacy bra too, exposing her lush beautiful breasts to my eyes for the first time. Her bra had matched her panties, pitty I’d thrown the panties out. I let the remains of the dress stay underneath her, so she looked like a candy bar that had been unwrapped, ready to eat.
My dick was already getting hard at seeing her presented as such, so I climbed on top of her, one knee on each side of her chest. I grabbed her two perky little nipples, and, pulling on them, proceeded to give myself a little titty fuck. My dick got rock hard feeling her smooth white boobs rubbing against my cock, and the tears that had rolled down her face earlier began to flow again. I paused titty fucking her and rubbed my penis around on her face, getting it a little wet from her tears and smearing her makeup around, then I climbed back, positioned myself at her ass hole, and shoved.
Honestly, it was pretty painful. Unlubricated, it was very hard to push inside of her, and, though the moisture from her tears was sexy, it did little to help push inside. Her super tight sphincter pushed back at me while I tried to shoved my way in, and as I pressed, she started to pant and moan in pain as the ankle chains bit into her flesh, holding her in place. After a little while of this, I pulled back, spat on her pussy and ass hole, and tried again. This time she started to really scream, but I got myself firmly inside of her. Holding her tight to me, I started thrusting, and I knew that, even though it would be the second time that night, I’d cum quite quickly. After just a few pumps, her ass muscles, which had been pulsating on my cock the whole time, pushed me over the edge. I started filling up her ass with a few pumps of my seed before I pulled out and spent the remainder of it on her face and breasts.