I (22m) was dating a woman a bit older than myself (34f). She had a rough past that we won’t get into, but one of the things that came out of it was her desire to please. It was a gold mine for sex. We had one late night conversation about something traumatic she endured, and for some reason the experience left her with a deeply rooted rape fantasy. I told her I wasn’t sure if I could do that to her, all while I was secretly planning it in my head.
I waited months so surprise would be on my side. We went to bed and I left the bedroom window unlocked. I waited until I heard the deep slow breathing of her sleep, and I grabbed an empty water glass as an excuse in case she woke up. I went out to my car and got my bag. Gloves, mask, rope, lube, and a faithful wooden baton from an army surplus store that resembled an old police Billy club.
I stalked up to the window and waited. She was still in the same position on her stomach, one knee high up. I slid the window open and climbed in, painfully slowly, but this next part had to be quick. Decisive. Violent. I struck, quickly hopping onto her, my knee and shin across her shoulder blades. I held her face down with my gloved hand blocking any chance of her seeing me. I lifted my knee slightly and pulled her oversized shirt up and over her face. She was thrashing. Her screams muffled by t-shirt and leather. I grabbed the rope with one hand haphazardly looping it around one of her wrists, then looped it around the other. I took the end and pulled it through her wooden bedpost and wrapped it enough to be taut. This was too easy.
I could see her fear in the form of sweat glistening on her back. Perfect. “Shut the fuck up. I don’t need you alive for what I’m about to do”. Surely she recognized my voice. But maybe she couldn’t tell over the sound of her own gasping and whimpering. I got off of her to grab her ankles and yank her toward the end of the bed. Stretching her tied wrists over her head. I pulled at her panties so hard the fabric stretched, tearing a little, and let them hang over her thighs. I could see her cunt was glistening. “I picked the right house. You fucking want this you little whore”. I took the wooden club and pressed it against her wet slit. I applied pressure, and slid it inside of her. The sound she let out was a sobbing “no!” With so much pleasure in it. I held one ankle while she used the other desperately trying to kick and roll herself. I kept fucking her with that club. Her body had this way of convulsing when she came, and before long, I saw just that. Her legs went limp. I pushed the club in until it stopped against her cervix, and sat on her legs, straddling them.
“You got yours, now I get mine”. I took the lube and squirted it onto her asshole. She started sobbing and screaming in protest. Kicking my back with her heels. I unzipped my pants and pulled my cock out, throbbing with desire. I pressed the head against her tight little hole, her heels still hitting me. “Beg me to stop” I told her. Before she could even get the first word out I forced myself inside her, right to the hilt. I could feel the baton through her anal wall. I didn’t waste either of our time. I pounded her endlessly until my cum was flooding her tight ass. The baton had slipped out and her juices were pouring from her swollen pussy.
I took my mask off, climbed up to her hands and unraveled the rope. Took the shirt off from over her face and let her see me. She had the biggest pirate smile of relief. I kissed her forehead softly, and laid down next to her. She crawled down between my legs, looked up at me with tears and eyeliner streaming down her cheeks, and sucked me slow and deep. She had the most wonderful way of saying thank you.