Now everything was set up for next saturday but to be sure everything would work out as I wished I did have to try the effects of the sleeping pills I had picked up. So after dinner that night I made drinks for me and Jess. To her drink I added two carefully pulverized sleeping pills. It only took ten minutes after she finished her drink for her to get sleepy. I told her she looked tired and that she better go lie down for a while and she did. Five minutes later she was laying on our bed completely passed out. I quickly stripped her naked without getting any signs of response from Jess. I grabbed her big soft boobs and pinched her nipples hard, when awake she always cries out a little in pain as I that but now there was nothing. I turned her over and grabbed her ass hard, digging my nails into her butt. I slapped her on her ass with my hand one, two, three times, nothing. I slapped her as hard as I could leaving a big red hand shaped mark on her right butt cheek. She didn’t even move. I spread her legs wide and spit on her pussy before opening her up and pushing three fingers in her as deep as I could. I finger fucked her a little and felt her pussy responding by getting wet. I fetched our box of sex toys and took out a butt plug. It’s the type you can expand in size by pumping air into it. I put a little lube on it and shoved it inside her ass. I started pumping it up a good deal until I could see her asshole stretch. I had never pumped it to this size before. I picked out one of our biggest dildos and forced it as deep into her pussy as I could. I then took my leather belt from my pants folded it once and began whipping Jess’s round ass with it. After five strokes her ass was getting really red and she squirmed a little making making some weak noises. I gave her about ten more strokes to see how much punishment she could take without waking up. It seems the pills had done a great job, she was still sleeping heavy. I rolled her over on her back again and pulled her body around so her head was on the edge of the bed. Jess, when awake, is a good cock sucker but she can’t doesn’t like to do deep throat. I now forced her mouth open and put my now throbbing dick into it. She gave no response so I pushed it further into her mouth and pulled in and out a couple of times before I grabbed her head with my hands and slowly forced my dick down into her throat deeper than ever before. I felt her choking as her passed out body tried to deal with my dick in her throat. I pushed it a little deeper before I pulled out of her. Jess coughed and quite a lot of saliva ran out of her mouth and covered her face. I forced my dick down her throat once more with the same gagging reflex from Jess. I then turned her body around so her pussy was on the edge of the bed instead and pulled out the dildo. I pushed my dick in her pussy and fucked her deep and roughly for a couple of minutes. I lifted her legs up above my shoulders to get even deeper into her and it felt so good fucking her like a real whore. I pulled out of her and deflated the butt plug and pulled it out. I lifted her legs again and fucked her widened asshole until I was ready to cum. I pulled out of her and climbed up on the bed above Jess and started shooting my big load over her belly and tits on my way up to her face where I dumped the last of my cum in her mouth.
The next day she didn’t wake up until midday. At first she didn’t seem to notice anything different, not until she sat down at the table and asked me why it hurt her butt sitting on a chair. She also wondered why her pussy and her asshole was so sore. I told her after dinner last night we had some drinks and she had gone a bit crazy with the sex. I told her it turned into a fantastic night of really wild fucking and asked her if she didn’t remember any of it. She didn’t and I told her she had been great and that I loved her very much.
It took just a couple of days at the office without being harassed by her admirers for Jess to be more happy about going to work and on the friday i even managed to make her wear her sexy skirt again without panties on.
At 6 in the afternoon I suggested we take a drink before dinner and Jess thought it was a nice idea. just like the last time I mixed two sleeping pills in her drink and at half past six she was completely passed out laying naked on her bed. I had also pushed the inflatable butt plug up her ass and pumped it up as much as I dared. I had some dinner and watched TV while waiting for the guys to arrive. They were early and a quarter to ten all five of them had arrived. None of us wanted to waste any time so as soon as everyone was there we went into the bedroom and gathered around naked passed out Jess. I could see the excitement in their eyes. It’ll the group the only rule for the evening: no permanent damage.
I asked Rob and Kenny to hold her legs apart so I could remove the butt plug from her ass. When it was out Jeffrey, Jess’s boss said he used fantasize every morning when arriving at the office to bring Jess into his room and bend her over his desk and spank her. We carried Jess’s limp body by arms and legs out into our kitchen and bent her over our kitchen table, Rob and Kenny holding her in place by her arms. Jeffrey stood behind her held his arm out and slapped her hard on her butt. I could see the excitement in his eyes as he kept slapping her round ass with his hand. After about 10 strokes Jess’s ass had begun to take a slight pink colour. Jeffrey took off his his belt and folded it then started whipping Jesses ass fast and hard with it. Her ass turned red with marks from the beating and Jess started squirming a little and made some faint crying noises. After a while Jeffrey dropped the belt, pulled his pants down and harshly forced his dick into Jess’ pussy. Kenny and Rob still held her down on the kitchen table as Jeffrey fucked her hard and fast for a minute or two before he grunted and came deep in her pussy. As he pulled out of her Kenny dragged her by her arm hard over the table so her head fell down over the edge. He pulled her head up by a firm grip of her hair with his left hand and opened her mouth with his right and pushed his dick into her mouth. He pushed his dick back and forth in her mouth. Meanwhile Rob climbed up on the table and positioned himself over Jess’s body. He pulled her butt cheeks apart and spit on her asshole and slowly began working his cock into her ass. Kenny had started pushing his dick deeper into Jess’s mouth and throat and she had begun making some gagging noises as he pushed deeper down her throat than she could handle. Rob had now worked himself all the way into Jess’s ass and was fucking her hard and fast making short pauses just to slap her ass hard between thrusts now and then.
Meanwhile Kenny mouthfucked Jess fast and pushed his dick down her throat. He pulled his cock out as he came in her mouth and on her face. When he was finished he turned her face up and spat a large blob of saliva on her face then used his hand to smear his saliva and cum over her face and into her mouth. When he was satisfied he slapped her face and sat down on a chair. Rob had kept fucking Jess up the ass and she had begun making little moaning sobbing noises as he fucked her deep and hard. After a minute or so more Rob came too dumping his cum up Jess’ butt.
John and Caleb had been watching the show until now, taking pics and videos with their phones.
Now John took Jess’ arms and Caleb her legs and they pulled her off the table and placed her on the floor on her back. Caleb put her legs together and pushed them up towards Jess’ head then he slapped her pussy with his other hand and pushed his cock deep into her pussy with one hard stroke. Jess was still kept asleep by the drugs but she started trying to squirm in her sleep giving out some faint moaning.
John had his hard cock out and held Jess’ mouth open with his hands. He spat a big blog of saliva straight into her mouth and then pushed his cock in, starting to fuck her mouth. They kept it up for a couple of minutes. Caleb switching between fucking Jess’ pussy and fucking her asshole hard, Jess’ big tits bouncing as he pushed hard and deep into her. Caleb was pushing his cock deeper and deeper down her throat and when Jess would start to gag he pushed deep down her throat and held her head for a couple of seconds before pulling out. He slapped her face and pushed back into her mouth again repeating the throatfuck.
Caleb finished first saying “someone make a vid when I cum in the whore’s face!”. He pulled out of her ass and moved up to her head. John held Jess’ mouth open as Jeffrey filmed with his phone when Caleb just managed to get his cock into Jess’ mouth as he dumped his load. Jess gurgled the cum and managed to swallow some of it before coughing the rest out on her chin.
John was now ready too and as Jeffrey kept shooting the video John shot his load all over Jess’ face and into her open mouth.
“Take the phone” Jeffrey said. He had been jerking as he filmed the guys fucking Jess and shooting their loads in her face and he was now ready to cum again. Caleb took the phone and filmed as Jeffrey sat over Jess stomach and shot his load over her tits and face.
As they were all finished now I asked them to help me carry Jess into the shower to clean her up. Jeffrey sat outside and the rest of the guys took one arm or leg each as I showered Jess off, rinsing her mouth, ass and pussy of as much cum as I could. Then we dried off with a towel and put her in bed.
I asked them to make sure to put all videos and pictures from the night on some online media share so we could all enjoy them. And I told them we should do this all again sometime.
When they had left I put on a condom and fucked Jess roughly in her pussy for a few minutes, then I fucked her ass and came hard before going to sleep.