Really Just Desserts Day 04byEvil_Teddy_Bear©
Note: These stories are pure fantasy. In reality I have been married for many years to a wonderful woman – she just is not into B&D.
As usual, the girls were jolted awake from their undoubtedly fitful rest by the blaring music. I particularly liked watching this part.
When I was in prison, this was the part I hated most. The rest wasn't so bad. Being relatively rich, I had established investment funds, which I funded and managed, for every guy in my cell block. Because of my money management skills, the guys who were in for several years left with at least enough money to get themselves established in the real world, rather than having to immediately go back to crime. This, plus my years of martial arts, insured that I had relatively little trouble inside. Despite all that, getting up every morning on someone else's schedule had still sucked.
"So ladies," I started after feeding them and giving them time to do their toilet. I was betting that after yesterday, the enemas would be very thorough. "Today is team competition day. Actually, team is probably a bad description. What I really mean is you will both be competing directly in joint competitions. Your first challenge is to show me what I missed when I was not included in your little love sessions."
I brought each of them out separately, laying them down on a double-size exercise mat and securing one ankle to the floor. I had faced them in opposite directions, offset, so that each girl was facing the other's pussy. Next I fastened the climax monitors to each of their backs and stood back to admire the scene.
"When I say 'Go' you will each lean forward and start eating pussy. This is a competition. The first girl to climax loses," I informed them. "I have left your hands free so you can use them and your mouth to bring your opponent off. I will think of a suitable punishment for the loser."
This was new to both of them. Although they had done this a lot in the past, some of it behind my back, they were always trying to cum as long and hard as they could. This time, they were trying not to cum at the same time their partner was doing everything she could to make her cum. It was a nice turn-around, one I enjoyed setting up.
At my signal, both girls went at it as hard as they could. I watched, getting turned on like most men by the girl-on-girl action. I took mental notes of techniques for future reference. I could not believe it when Debbie inserted three fingers of one hand into Lisa's ass, while almost her entire hand disappeared into Lisa's cunt. I could tell they were both trying as hard as they could not to climax, but eventually Lisa, (I told you she was a slut), shuddered and climaxed with her normal scream. "Time," I shouted.
"Well Lisa," I informed her, "it looks like you get punished first. However, since I am tired from all my exercise yesterday, I am going to have Debbie punish you. Of course, I will be grading her on her efforts, so if she doesn't do a really good job, she will take your place."
I moved Lisa to the corner mat, cuffed her hands behind her back, fastened each ankle to a separate line and hoisted her upside down into the air, her legs spread wide, exposing her dripping pussy. Deciding to up the ante, I ran an elastic line around the backs of her legs and attached each end to her cunt-rings, spreading her pussy lips wide.
Next, I gave Debbie a thin whippy riding crop and told her that she was to give Lisa 30 strokes, five on each nipple and cunt lip, five on her center and the final five on her clit. I warned her that I would be watching; any stroke I deemed too light would be given to her, in the same position, after she was done with Lisa. I planned to have fun with this. No matter how hard the first stroke, it was not going to be hard enough. I was sure I could get Debbie to whip Lisa harder than I ever would. As a bonus, when it was Lisa's turn to punish Debbie, she was going to want revenge.
The first stroke, to Lisa's left nipple, was half-hearted, to say the least. Lisa barely even yelped. "Debbie, that was terrible," I stated. "That is one stoke to your left nipple. If I have to fine you more than five out of these thirty, I am going to give you all thirty as well."
The next stroke, to Lisa's right nipple, was harder, making a dull crack as it landed. Lisa whimpered. "Better," I advised her, "but still not good enough. That is two I owe you."
The next stroke to Lisa's cunt lips made a wet crack as it hit her dripping cunt, followed quickly by a second to the other lip. Lisa screamed, and then subsided.
"Now that's more like it," I told Debbie, "I knew you could do it. Let's concentrate on the nipples, then the cunt lips, saving the last two areas for last."
Debbie landed the next four strokes on Lisa's poor nipples, gradually pulling her strokes as Lisa sobbed. By the fifth, I interrupted her, telling her "That one was too light. That is three I owe you. So far the strokes are all on you nipples, so you might want to be careful later when you move to the more sensitive areas. You wouldn't want to earn any clit strokes, for example."
The last four to the nipples were great, so hard that even I flinched. She had also begun using a side stroke that brought the full force right on the nipple. Those must have really stung, because Lisa was really shrieking each time one landed.
"You are doing great," I encouraged Debbie.
The next eight to Lisa's cunt lips were brutal, making sharp, wet cracks each time one landed. Lisa was hysterical, her body arching and jerking with each stroke, so I decided to give her a bit of a break, telling Debbie to relax for a couple of minutes. When Lisa had subsided to quiet sobs, I had Debbie start on the last ten strokes. The first one to Lisa's center was actually pretty harsh, but I still told Debbie "that is four I owe you. I guess you really want this as well." The next four were again brutal, making loud cracks that were immediately followed by Lisa's shrieks.
"Great," I complimented her. Now finish the final five on her clit."
Debbie did as she was told. However, I decided that she had pulled the third one, probably because Lisa was screaming so hysterically. "That is five I owe you. Any more soft strokes and I will have to give you the entire thirty strokes."
Debbie got the message. The last two strokes really made me wince as they landed. Lisa screamed then subsided to just crying. I let her down and put her back in her cell. Debbie just waited quietly while I did that, then lay down on the mat when I gestured and was still as I attached the ropes to her ankle cuffs. I suppose they were both getting resigned to their punishment.
"So," I consoled her, "it could be worse. I owe you three nipple strokes and one each to your cunt and clit. I especially liked your little side stroke to the nipples. I think I will use that myself."
Debbie was starting to sweat as I hoisted her legs into the air. I hoisted her higher than I had Lisa since I wanted her nipples at a good height for punishment. This had the unfortunate (at least for her) side effect that her legs were really stretched open, since the ropes were at an angle to her body.
I swung the crop hard and the first stroke caught her left nipple squarely. Her body arched as she thrashed and screamed, then screamed again as her threshing about stretched her already spread legs.
I had stood off to one side and aimed the blow down at an angle to make sure the very tip caught her poor nipple perfectly. Satisfied, I moved to the other side and repeated the stroke to her right nipple. Again she threshed about and gave up a nice double scream. "Please no more," she begged.
"OK," I agreed. "We have the pussy and clit strokes left but I will spare your nipples the last stroke," I promised. I stepped back in front of her to line up the pussy stroke. Artistically I wanted to make sure I got the very center of her sorely spread cunt. I did. The hard stoke was followed by a moment of shocked silence, then by a shrill shriek as the pain settled in. I gave it a minute, then I tenderly stroked her about-to-be-abused clit with the tip of my finger. Debbie whimpered in anticipation. I stepped back and aimed an angled stoke, designed to once again have just the very tip hit her clit. Her scream was almost painful, but rapidly evolved into sobbing.
Finally I moved behind her for the final stroke. Although I had promised to spare her nipples. I had not promised to spare her ass. I used a finger to gauge how she was doing back there after her ordeal of yesterday. Surprisingly, her little asshole was still fairly tight as I moved my finger in and out. I wondered if I needed to get a bigger attachment for the punishment pole. I had thought 13 inches was big enough, but maybe not.
The last stroke caught her vulnerable little star, again with just the very tip of the crop. Listening to the scream and sobs, I hoisted her even higher until her mouth was even with my crotch. I thrust my very hard dick into her mouth. Since she was hung upside down with her hands behind her, I was able to do an excellent mouth-fuck, eventually cumming straight down her throat. She coughed and gagged but didn't actually throw up.
I let her down, put her back in her cage and decided to take a break.
I came back about an hour later, ready for round two. I put them in the same positions on the mat, but gave them each two vibrating dildos. "OK ladies, this competition is the same as the last but instead of your mouth, you can use one or both of the vibrators. Again, loser is she who cums first."
I hoped and suspected that Debbie would lose this round, if for no other reason than that Lisa's cunt was too sore to let her climax after the beating earlier. I was right, but it went on a good thirty minutes before Debbie finally succumbed. By that time, Lisa had the smaller vibrator all the way up Debbie's ass and was vigorously working the larger one in and out of her cunt.
"Time," I shouted. "Well Debbie, it looks like you lose this time. I think it only fair that Lisa get her chance to punish you."
I unfastened Debbie, and then moved her over to my favorite low wall. As usual, I fastened her legs to the wall with her torso over the top, tightly strapped down to the inclined board. I hung weights on her nipple rings and fastened elastic cords to her cunt lips rings to spread her wide. I stepped back to admire the view.
Next, I brought Lisa over, handed her a 12 inch strap-on and told her to put it on. The strap-on had a vibrating, five inch extension that went into her cunt. Unfortunately, the batteries powered more than the vibrator. "The strap-on has two functions," I told Lisa. "The first is to vibrate the part in your cunt. However, there is also a timer and a pressure switch on the front end. The timer is variable, but decreases over time. At the start, the switch must be triggered every two seconds, but as time passes the interval decreases. After ten minutes we will be down to half-second intervals; and the end switch needs a lot of pressure. What this means is that when you start fucking Debbie, you need to bottom out, forcefully I might add, before the timer goes off. If you do not, the part in your cunt will give you a really nasty shock. As time progresses, you will need to fuck both harder and faster to avoid the shocks. We will set the timer to thirty minutes. Good luck."
Just for fun, I positioned Lisa behind Debbie, helped insert the strap-on tip into Debbie's' cunt and then bent Lisa over the wall fastening her hands to Debbie's nipple rings. The hands, plus the weights, were probably going to give Debbie's nipples a real stretching. I started the timer, stepped back, and used the crop brutally on Lisa's exposed bottom. She lunged forward, away from the whip, burying almost the entire twelve inches in Debbie's cunt in one brutal motion. Debbie let out a shocked scream.
Shocked that she had caused the scream, Lisa jerked back out. Of course, pulling back meant that her hands pulled hard on Debbie's nipple rings. Debbie screamed again. As Lisa hesitated, the shock rings on the part buried in her cunt fired, causing a shrill shriek from her. Two seconds later they fired again, and yet again. By the third set she had placed the strap-on back in Debbie and was trying to slowly insert it. The fourth set of shocks caused her to ram it home all the way. Debbie screamed again.
It went on that way for a while, Lisa trying to go easy on Debbie, but eventually the continued shocks wore her down and she began thrusting as hard and fast as she could. Debbie had quit screaming by this point and was just making little grunting sounds each time the invader slammed into her cervix. Eventually the continuous hammering got to her and the grunts turned to moans, then finally a shriek as she came hard. I flipped the remote switch to turn the shocks off, positioned myself behind Lisa and slammed all the way up her ass with one thrust, bottoming the strap-on out in Debbie as I forced Lisa forward.
I could feel the vibrating part in Lisa's cunt each time I stroked in, tightening her already tight ass even tighter. The combination of the vibrations and friction on my cock, plus the sounds from both Lisa and Debbie as we did our daisy-chain fuck had me cumming in only a few minutes.
I called a halt at that point, unfastened them and put them back in their cells to rest while I took another break.
I gave them an hour and then I came back in for the final contest of the day. I took Lisa out first, taking her over to the corner mat. I fastened her hands behind her, then had her lay down on the mat and once again attached the ropes to her ankles and hoisted her into the air. Debbie was next, although I had to listen to a lot of sobbing and begging as I set her up on a second set of ropes facing Lisa. I used short pieces of elastic to connect the rings on each side of their cunts to the other girl's corresponding ring, making sure the elastic was stretched tight. I made the same connections with their nipple rings.
"These candles are specially made to be used to decorate wine bottles with running wax," I said showing them a couple of tall 14 inch candles. That means they burn relatively quickly and melt a lot of wax which runs down." I seated the base of the first candle all the way down in Debbie's cunt until it bottomed out and then decorated Lisa the same way with the second one. The girls looked nervously at each other.
"I am going to light the candles. The first girl to drop her candle out of her cunt loses. By the way, you can squirm around if you like; the elastic connection might make your opponent lose her candle." Face-to-face, even if upside down, the girls looked at each other as they thought about that.
I lit the candles, picked up a bourbon at the bar and settled down to relax and watch.
At first, not much happened as the candles got going. However, eventually the hot wax started running down the long sides of the candles. I watched the shocked gasps when the first of the hot wax reached their spread pussies. Of course, as the candles burned down, more and more wax came down and the lower the candles burned, the hotter the wax was.
Eventually Lisa had had enough and quickly jerked her body back, trying to make Debbie lose her candle at the unexpected tug on her cunt and nipple rings. It didn't work, but they both moaned as the motion stretched their tits and cunt lips. Of course the motion also caused more wax to run down, leading to more shocked gasps. It went on this way for several minutes, each girl trying to surprise the other into expelling her candle. I was getting quite a show. Finally Debbie tried a violent twisting jerk which caused them both to scream as their nipples and pussy lips stretched, but also shocked Lisa enough to tighten her cunt and expel her candle.
"Debbie Wins," I advised them, putting out the fallen candle.
I removed Debbie's candle, lowered her and put her back in her cell. Returning, I lowered Lisa flat on the mat but left her attached while I thought about her punishment.
I decided on the fucking machine, but instead of the customary selection process, I decided on a special double shaft attachment I had had made. One shaft was 10 inches and the other 8 inches long, designed to fill both holes at once.
I positioned Lisa at the familiar low wall, fastening her spread legs to the wall and attaching lines to the cunt rings to hold her wide open. This time however, I removed the angled board and left her upper body free, but still bent over the wall. I positioned the fucking machine and made sure it would bottom out properly in both holes. Next I attached weights and lines to her nipple rings. I stepped back to check the scene over. Satisfied, I started the machine, listening to her groan as both holes were suddenly filled.
Next I stepped in front of her and picked up the lines to her nipples, tugging her body forward, stretching her nipples, my hard cock sticking straight out.
"The machine will continue until I cum in your mouth. If I were you, I would start sucking," I counseled her. Lisa got the message.
Because of the position and with her hands behind her back, she really had to let me set the pace and the depth. I took it slowly, varying both so that I did not cum too soon. Since I had already cum twice today, this had the effect of drawing this out well past the thirty minute mark. Her groans and occasional gasps as the machine bottomed out made delightful vibrations on my cock. I started timing my thrusts to match the machine so that I was all the way in when the machine bottomed out. The machine hummed on, slamming the invaders faster and faster into her cunt and ass. Finally it became too much for me and I came deep in her throat, forcing her to swallow it all. Satisfied, I turned off the machine and put her back in her cell.
I cleaned up and brought their dinners down.
"Good night ladies," I said as I dimmed the lights. "You have both done well. As promised, tomorrow is your last day here. I am sure you will enjoy it."