I'm trying this from a mans point of view, I hope I do ok.
My friend Jake and I sat in my van, across the street from her house, waiting for her to pull into her driveway. I had been watching her for weeks and couldn't take it anymore. Enlisting my buddy's help, I talked her up to him and Jake is always down to do anything with me. It hardly took any convincing, as long as he got to get some too. I have never done anything like this before but like I said I couldn't take it anymore. All I saw was this chick, she had crawled under my skin in a good way.
I watched her drive down the street and pull in her driveway. The door opened to her car and one slender leg emerged, then I saw her completely. I smacked Jake on the shoulder and pointed to her.
"Fuck yeah, man" he said. Both of us watching her unlock her door and close it behind her.
"So heres the plan, we wait until she goes to bed, probably twenty minutes after all the lights go out, and we use your expert locking picking skills and get in, put on our masks, once we get blindfolded and subdued, its anything we want, man." I said, still watching the house. Jake nodded his agreement and we sat there waiting it out.
We rolled a doobie or two, hell, maybe three, I don't remember and then the lights went off. Finally I thought. I told Jake to get ready, we were going to go soon. We both grabbed our masks and gloves and I put mine on to eager to just sit there with it in my hands. "Dude" Jake said "Chill, man. She isn't going anywhere." All I could see in the dark van was the tip of his lit cigarette.
"Fuck it, man, come on." I said. I opened the door to the van and stepped out, Jake quickly followed. We quietly walked across the street and up the driveway. We crept around the side of the house to the back door. I stood there, trying to be patient as Jake knelt down and opened his bag, bringing out his tools, within seconds the door was open. This was it, stay calm, I was already hard, thinking about what I was going to do to her. We walked through the kitchen and through the dark living room, everything was quiet. We quietly walked down the hall, coming to the slightly opened door at the end of the hall. I looked at Jake one last time and he nodded. I nodded back and pushed open the door. I could see her sleeping form lying on the bed, Jake went and stood at the end of the bed, I walked to the side of the bed and reached down and covered her mouth. Her eyes flew open, darting around madly. She tried to move but I held her down.
"Shhhh!" I whispered harshly "I promise, as long as you as your good,we wont hurt you." I sat her up and wrapped her arms behind her back, handcuffing them behind her. Jake sat the bag down next to me and I pulled out the scarf, wrapping it around her eyes. After I was satisfied she was completely covered, I stepped back and took my mask off. Jake already had his off and turned on her bedside lamp, we both looked her over. Her long burgundy hair done in a side braid hung on her shoulder, the tshirt she was wearing, was kind of ratty and old, but I didn't care soon it would be off. I assumed she was wearing panties, but didn't see any, because of the t shirt length.
Jake and I sat down on either side of her. I was surprised she was being so quiet, but her breathing was getting heavier and heavier. I looked over at Jake and he already had his cock in his hands rubbing it up and down. I ripped her shirt and she whimpered. Her full breasts sat there, amazingly perfect. Full and perky, with perfect rosebud nipples. I reached up and started rubbing around her nipple. There was no reaction. Almost like fondling a rag doll. Not that I cared. I did not need any response to get what I wanted.
"Please don't, please I have money, just please don't hurt me." She sobbed. I ignored her and lowered my mouth to her nipple, flicking it with my tongue. Jake was playing with her other nipple. I rubbed the outside of her panties, I could feel her wetness through the cloth. "You are so naughty, baby." I whispered in her ear. I turned her face towards mine and stuck my tongue in her mouth. She tasted like cinnamon. I pulled out her braid and dragged my fingers through her soft hair. "Lets get started." I said to Jake, but felt her stiffen up at the same time.
I grabbed the back of her head wrapping her long hair tightly through my fingers. I had complete control over her head movement and turned her to face Jake's hard cock, She began to struggle hard but I held her tight. "Please don't do this to me!" she begged, which just encouraged us more. Jake needed no encouragement and moved his cock near her mouth which she had closed, I took my hand from between her legs and took hold of one of her nipples in my fingers squeezing it hard. As She yelped Jake took his chance and forced his cock into her lips and began to fuck her mouth with long slow deep strokes.
I sat there holding her in front of Jake, watching him get mouthed fucked. I held her wrists with one hand and the other pulled down her panties. I stuck my fingers deep inside her, causing her to moan . "See I knew you were enjoying this." I said guiding my cock towards her wet lips and rammed myself into her, fucking her roughly. With every thrust it made Jake's dick go deeper in her mouth as she gagged a little. This was exactly what I wanted, this night was going fucking perfect, her pussy was tight and hot, and so fucking wet. I heard her muffled groan as I forced my thumb all the way in her tight ass making sure it was ready to take my rock hard cock. Her pussy began to flood with cum as tiny orgasms flowed through her body I could feel the muscles of her cunt grip me tightly as I fucked her.
"Dude, lets change it up, I don't think she can breath." he said laughing, as he pulled his cock out of her mouth. She was gasping for air at this point. We both laughed. Jake laid back on the bed, Jake wrapped his arms tightly round her back as I gripped and lifted her by her thighs spreading her legs wide at the same time, she began to struggle again trying to kick her legs out of my hands. But the more she struggled, the tighter we held her and between us we overpowered her.
As her pussy sank over Jakes erection she gasped and groaned at the same time as she felt his cock fill her tight wet cunt, his reaction was very similar. I sat back and watched Jake fuck her, still tightly hugging her in case she tried to escape.
I placed a palm on the small of her back pushing her down on to Jake and raising her ass slightly with my free hand, I grabbed my now painful erection and guided it to her ass, I made some small adjustments until it began to spread her tight sphincter. The muscle gave way and I felt her take a deep breath as she knew what was coming, I pushed it hard to her, her ass-hole stretched tight over me as I slid all the way in. She let out a low guttural moan as both her holes were filled and firmly fucked by Bill and I. She began panting and I could feel her pulse racing as we picked up the pace as she was fucked really hard by us both. I felt some jerks. and at first I wasn't sure who it was but as Jake's "Oh fuck yeahs", filled the room I knew he was cumming, he must have shot loads of hot cum in to her nice little pussy because I could feel the deep pulsing of his ejaculation through the walls of skin between her ass and pussy on my cock. She was now arching her back pushing her ass harder onto my cock as I fucked her anally harder and harder. Her body was trembling and spasming as a huge orgasm racked her body, her anus gripped me tightly as it throbbed with her orgasm, this was too much for me and I began to cum shooting loads of cum deep up her ass. I slowly continued to fuck her ass as her orgasm subsided and to make sure I drained every last drop of my cum. Jake finally relaxed his grip and pulled out of her. She rolled to the side of Jake, and lay there breathing heavy.
We both put our masks back on. I undid her hands, and she pulled them to her chest rubbing her wrists. "Ok. Listen to me, this is how its going to go. You are going to stay on your bed until, the alarm on your nightstand goes off. Then you may remove the blindfold. If you remove it before than, I will shoot you, If you call the cops, I will shoot you and your family, I know where you work, where you grocery shop, where your favorite restaurant is. Don't make me hurt you." I said gathering up my stuff.
" Thanks, doll, you made our night." Jake said as we walked out of the room and down the hall, out the door and too my van. I started it up and we were gone.