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Really Just Desserts

By: Evil_Teddy_Bear



I flicked the switch and the lights came up, momentarily blinding the two naked women sitting cuffed hand and foot in their cages. When they could see again, Lisa saw me and gasped. I was her ex-husband, the one she and her lover Debbie, the woman in the other cage, had framed for spousal abuse and had sent to prison for the past four and a half years. They had developed the scheme so that they could be together and get most of my money in the divorce. I had gone to jail but it hadn't worked out as far as the money went. The pre-nuptial agreement and my attorney were just too good. All she got was less than half a million from her share of the house, most of which I knew was gone now after over 4 ½ years.

"Despite what most people think, there are several advantages to being in prison", I said into the silence. "The first is that I had a lot of time to work on my trading portfolio. It is now worth a little over fifty million dollars. The second is that you meet all kinds of useful characters, such as the leader of the gang that kidnapped you and brought you here. The last is that it is a perfect alibi for a kidnapping that happened days before you even get out."

"Where are we and why are we here, you bastard?" Lisa demanded. "You will never get away with this." 

"Actually, I will", I stated calmly. "Remember the lawsuit papers you were served with just before your kidnapping? There is a preliminary hearing next week. I will get a summary judgment since neither of you will appear in court. Alas, I will never get the money I will be awarded since it will appear that you both cleaned out your accounts and skipped the country. You know, Lisa, you really should have changed your password. It made it too easy for the hacker I hired, another useful prison acquaintance, to get into your computer system. Further investigation as part of my lawsuit will uncover a series of emails where you and Debbie planned your escape and, incidentally, admit to framing me. I might even be able to get a pardon. On the other hand, you will both be wanted for perjury"

"As far as your other questions", I continued, "You are in the basement of a lodge I built on that land I bought upstate. As for why you are here, well it is for revenge for me and punishment for you, of course. I was in prison for four and a half years because I wouldn't admit my guilt and ask for parole. Frankly the idea of keeping you here that long disgusts me so I have decided on four and a half days. This is Day 1; on the evening of Day 5 you will be shipped off to the Cayman Islands on a private yacht. If you are nice to the crew, they won't throw you overboard for the sharks. If you do get to the Caymans, you will be put onboard a private plane to Mexico City. Each of you will have ten thousand dollars cash. Everything else you have has already been transferred to accounts in the Caymans that everyone will assume were yours before they were cleaned out, but are actually mine. This will explain where you have been if anyone traces you. After that, I don't care where you go or how you live, but you should probably stay out of the US for the next seven years until the statute of limitations expires on perjury. Come back before that or make trouble and I assure you that you can both be made to disappear for good. I used to be nice, but not so much anymore." 

It was mostly the truth, just not the whole truth. Our location was a lie, but they wouldn't find that out until too late.

"In the meantime" I concluded, "I am going to make up for all the sex I missed these past four and a half years, including things like taking that tight little ass you denied me in our three years of marriage, and teaching your lesbian girlfriend what sex with a man is like. I also decided that I really should try out S&M since it always interested me, and now I have two eager volunteers."

"First a few ground rules. If you are good, you will survive all this with no permanent damage, other than a few piercings in strategic places. Every morning when the alarm sounds and the lights come up, you will have thirty minutes to shower and use the toilet – no need to dress. I strongly suggest that you use the enema syringes provided since you will usually have to clean my dick with your mouth after it has been in your ass. Naturally I will be filming all of this. I will then bring in your breakfast and give you another thirty minutes to eat and clean up. After that, you're mine. We will "work" through lunch and you will get dinner only after we are finished for the day."

"When I am present," I continued, "you will speak only when spoken to; you will refer to me as 'Master' and you will obey my orders immediately. You have probably noticed all the cameras and equipment in here. It is nice to have the money and creativity to really indulge myself. All of this is designed to cause you pain and give me pleasure. And, like all good S&M scenes, you do have a safe word or safe phrase really. Yours (and please be sure to remember the exact phrasing or it won't work) is "Please Master, fuck my ass". Naturally, if you use your safe word, I will then stop the current scene and respect your safe word by doing just that - fucking your ass. We will start with my 8 inch dick and then if you lose the coin toss, my fucking machine. The attachment size used will be selected by a random drawing. It has 7, 9, 11, and 13 inch attachments. Frankly, the thought of the 13 incher hammering away for 15 minutes in your ass scares even me, so you might want to be careful using your safe word. The fucking machine will also be used for punishment, but with different attachments. Those are the same sizes but have electrified metal rings which give a really nasty shock to your poor ass or cunt every time it bottoms out. For punishment, I get to select the attachment size, which opening it goes in and I will set the timer for either 15, 30 or 60 minutes depending on the seriousness of your transgression." I also have other toys I may use, at my sole discretion.

"So here is your breakfast" I said shoving the bowls into the cages. "Hobble forward to the bars and I will unlock your wrist cuffs so you can eat, but the ankles cuffs stay chained together. Today only you have one hour to eat, shower and use the toilet. I will be back in one hour." Both women hobbled forward and I unlocked the short chains securing their wrist cuffs to each other but left the cuffs themselves locked in place and left the room.

Re-entering the dungeon an hour later, I stated "It is time to get started. I have decided to flip a coin to decide today's lucky lady. Heads it is Lisa, tails it is Debbie." I dramatically showed them the coin, flipped it and then called out "Tails – I guess this is Debbie's lucky day."

I opened the cage door and forced Debbie out, despite her struggles and swearing, pushing her down face up on a narrow bench and clipping both of her wrist cuffs to a ring at the end of the bench, over her head, with her pussy at the lower edge and her naked legs hanging off the end. Debbie was a slender blonde, a bit taller than Lisa's five foot five with nice, full c-cup breasts, small, pale nipples and a killer ass. Too bad she didn't share those lovely assets with guys, at least not before now. Since she was already naked, stretching her out on the bench forced her tits out enticingly so that they jiggled slightly as I positioned her to my satisfaction. Next, I unlocked the short chain joining her ankle cuffs and attached each ankle to the end of a spreader bar affixed just below the end of the bench. I expanded the bar until she was spread as wide as possible and locked it in place. Lisa watched nervously as her lover was secured, but, at least for now, stayed silent.

Next I opened a large equipment cabinet on one side wall and contemplated the instruments there. Selecting a short whip with a single long lash about four feet long, I returned to the bound beauty. "Normally" I informed her, "you would receive extra punishment for struggling. I will mostly overlook the struggling and cursing just this once, since I am planning on punishing you anyway. However, I strongly suggest that you be more careful in the future. As a penalty though, you cannot use your safe word for the first hour."

Positioning myself at one side, I started using the whip just above her elbows and moved up the insides of her upper arms to her armpits, first one side and then the other, the whip making sharp cracking sounds when it struck and leaving a vivid red welt each time it struck. Although the room was completely soundproof, her loud shrieks every time the whip struck started annoying me, so I stopped and stuffed her panties, removed with the rest of her clothing before she was forced into the cell, into her mouth and secured them in place with duct tape. I would have to take them out later to use her mouth and so she could use her safe word, something I was looking forward to making her do. As I did this, Lisa broke her silence and started screaming at me and calling me names. I silenced her by pointing out that she had just earned punishment for herself and that if she persisted, I would also double the number of strokes I planned to give Debbie.

The next target was Debbie's stretched out stomach, moving up her ribs toward her round but vulnerable tits with their small, pale, and now fully-erect nipples. I was glad for the gag since I could tell the shrieks now would have been even louder. I stopped just short of her tits and next whipped her thighs, starting just above her knees and moving ever closer to her cunt and clit. As the strokes got closer to the center of her womanhood she was really shrieking behind the gag and struggling frantically to escape. Again I stopped just short of her most tender target and moved back up to her tits. I had been somewhat hard ever since I bound her to the bench, but my dick was rock hard by this point; I was really looking forward to putting that erection to good use soon.

The next series of whip strokes focused on her tits, first the fleshy breasts and then the erect nipples, first one side, then the other. The whole breast jiggled delightfully (at least for me) for several seconds after each stroke and I was pausing after each stroke to allow the pain to soak in. Each sharp crack of the whip was also punctuated by her muffled shriek and frantic attempts to lift herself completely off the bolted-down bench to escape the lash. Since she was so obviously loving this, I just knew she was really going to love the finale!

After ten strokes to each of her nipples, it was time for the finale. Moving between her spread legs, I first checked her cunt by fingering her, dipping my fingers deep into her vulnerable and soon to be abused womanhood. Despite all her screams, she was dripping wet. I played with her for a couple of minutes, despite the protests she mumbled through the gag. Lastly, I began to stroke her clit. I wanted it nice and sensitive for the lash. When she began to involuntarily respond, I reached forward and slowly wiped my juicy fingers on her lips. Then I stepped back and brought the lash squarely down on the side of her spread and dripping cunt. The next nine were the same – right lips, left lips, repeat. Now the muffled shrieks were shrill and were interspersed with sobs and moans that were audible even through the gag.

I paused, thought for a moment and then went back to the equipment cabinet. Returning, I attached alligator clips with rows of sharp little teeth to each of her inner cunt lips, stretching them out by attaching elastic cords from the clips to rings at the side of the bench, spreading her pussy even wider. I ignored her renewed muffled screaming and stepped back, admiring the scene.

Naturally, the next five strokes of the whip were focused on her tender and now wide open center, accompanied by shrieks that were starting to be loud even around the gag. Finally, the last five whip strokes were directly on her clit, the sharp crack of each stroke accompanied almost immediately by a loud, prolonged but panty-muffled scream. At the third crack of the whip, she convulsed in a definite orgasm, and then really shrieked as the last two strokes hit her even more sensitive, orgasm-engorged, clit.

I checked the time – forty minutes gone. That left me twenty minutes to deal with my raging erection before she could use her safe word. I was pretty sure Debbie was technically a virgin and wanted to stay that way. I also suspected her flimsy hymen had long ago fallen prey to vibrators or dildos in her hands or the hands of girlfriends. Still, the idea that I might be the first man to actually fuck her turned me on. Since I wasn't sure if she would really sacrifice her ass to save her technical virginity, I had decided not to give her a chance. I planned to take her ass later anyway after I forced her to use her safe word.

I moved to the head of the bench and removed the panty gag, in case she wanted to beg. Standing right in front of her face, I then stripped my pants off. Her eyes got wider as I stripped, exposing my rock-hard eight inches. I then moved to the other end of the bench and stepped up between her legs to her sore pussy. Her clit and nether lips were red and puffy from the whipping she had received, but her cunt was still dripping wet. I placed my dick at her entrance and began teasing her, giving her an inch or so and then pulling out, then two, then three, watching her shake her head wildly and shrieking "no, no" almost continuously, interspersed with cursing and crying. She was very tight, I have to give her that, and I had to push hard to seat the last two inches, shoving up hard against her cervix.

Once fully seated, I slowly pulled out until just the head was still in her, listening to her gasp, then slammed back in all the way in one hard stroke, accompanied by a shriek. I began fucking her hard, in and out, varying the rhythm and making sure the top of my dick rubbed against her swollen clit. The squishy sounds of finally fucking a wet pussy after over four years were music to my ears. I kept this up for a solid ten minutes, finally cumming explosively deep in her cunt when I just couldn't hold out any longer. I think she may have actually climaxed again as well but with all her shrieking and crying it was hard to tell for sure. I rested in her for a moment then pulled out with a pop and walked back to the head of the table.

I cut off her sobbing by shoving my cock in her mouth, telling her "Clean it. Bite me and this past hour will seem like a picnic." Thoroughly cowed, at least for the moment, she licked and sucked our combined juices off my dick. I checked my watch. Sure enough, the hour was up. It was time to convince her to use her safe word. As I continued in her mouth, I began to get hard again. "Why not", I thought, and began to thrust with more purpose. Despite the fact that I had just cum, it took me less than five minutes to fill her mouth (and throat – I was thrusting pretty deep by that point) with cum. Blame it on over four years with no woman. Now it was time to move on.

Since the ladies were not going anywhere, I decided to take a break. I moved over to the wet bar I had installed on the side wall opposite the equipment cabinet and poured myself a generous shot of bourbon, dropping in a couple of ice cubes. Sipping slowly and really savoring the 18 year old bourbon, I contemplated Debbie, still fastened to the bench, and thought about next steps. Finishing the bourbon, I returned the glass to the bar and moved back to Debbie.

Since there were already clips on Debbie's cunt lips, that seemed a good place to start. I rolled a custom-modified battery charger over. The voltage had been stepped up from 12 to 36 volts, since 12 volts doesn't penetrate skin all that well, the amperage had been dialed way down for safety and the power leads split into six separate circuits. A custom-designed control board completed the setup. I attached two leads to the clips already on Debbie's cunt lips and added clips and leads to both of her still-throbbing nipples and to her swollen little clit. Like the ones on her cunt lips, each clip had sharp little teeth that really bit into her tender flesh. The final lead went to a small 4 inch dildo with electric rings spaced along the length. I raised the bar attached to her ankles and secured it to a pulley overhead, giving me unfettered access to her ass. After playing with her tight little asshole for a few moments, I inserted the soon-to- be-electrified dildo completely into her ass with one shove, accompanied by another squeal from Debbie. I secured the dildo in place with straps.

"Now Debbie", I explained, "this control will begin sending shocks in a random order to each of the electrodes on your body. Every five minutes, the power and frequency will increase. By the end of the thirty minute program the shocks will be really strong and almost continuous. You will probably lose control of your bladder, but not to worry, I will have Lisa lick up any accidents later. Always remember, you can use your safe word to stop this at any time."

"Good luck." I said, pushing the start button. Debbie grunted and bit her lip as the first shock hit her right nipple (the control panel had lights that indicated which area was being hit). I could see her relax slightly; no doubt thinking it wasn't so bad. In case you have never been tortured with electric shocks (I actually have) the thing about them is that your nerves get more sensitive with each shock. What starts out feeling relatively mild will eventually have grown men screaming. I made myself another bourbon and sipped it as I watched her squirm around as the shocks hit one spot then another, although sometimes the same spot would be shocked several times in a row. Debbie was not happy and shrieked and jerked with each new shock; I was not sympathetic and ignored her screams. After all, this was the bitch my wife had left me for and who had conspired to ruin my life.

By the end of the first five minutes, she was crying out with each new shock. By the end of ten minutes she was alternately screaming and crying. When the third stage hit she lost control of her bladder, making a mess, but also, since the urine was conductive, turning her entire crotch into one big electrode every time any of the electrodes down there fired. It was less than four minutes after that that she screamed "Fuck my ass". "Not the right phrase" I advised, smirking. "I told you the exact phrasing was important, although just this once I will overlook you not referring to me as 'Master'."

"Master, please fuck my ass" was her next try. "Close, but no cigar," I replied. "Please fuck my ass Master" was her next try. I continued to ignore the incorrect phrase. Then she began screaming almost continuously as time ran out, and the fourth stage of shocks began. Finally, "Please Master, fuck my ass" sounded between the screaming. I shut the shocks off immediately. "See, that wasn't so hard", I commented.

I unclipped the electrodes and unfastened her from both ends of the table, but left the spreader bar attached. She winced and moaned as circulation returned when each clip was removed. I then picked her up (lots of working out with weights in prison), flipped her over so that she was face down, carried her over and deposited her on a pad facing a low padded wall. The wall was about two feet high and had a padded 2x4 attached, slanting forward at an angle and secured at the far end to a platform with another ring. I secured her lower body, legs still spread, tightly against the wall and pushed her upper body down flat against the angled board. Next I secured her still cuffed-together wrists to the far ring, leaving her stretched out, head down and ass up. Because the angled board was narrow, her tits pushed out on either side of the board, her poor nipples begging for more attention. I finished with a strap around her chest, just below her breasts, locking her upper body to the inclined board. Once she was secured, I decided that it was time for Lisa.


Really Just Desserts Day 02



Author's 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.

*

The two girls in the cells groaned as the lights came up and "Reveille" blared out of the hidden speakers. I stood in the doorway and watched as they jerked up out of their beds and moaned with the sudden movement. Having had to get up on other people's schedules for over four years, my sympathy was very limited.

Lisa saw me and immediately started bitching. I guess she had already forgotten yesterday. No problem, I was looking forward to reminding her. Not wanting to listen to the same crap I had heard for years when we were married, I noted, "You have 30 minutes to shower and get ready -- don't forget the enemas," and left.

Thirty minutes later I was back with two food trays, which I shoved into the slots in their cells. "You have thirty minutes before the fun starts", I reminded them.

Thirty minutes later I was back again. "Now ladies, since Debbie went first yesterday, it is only fair that Lisa gets equal time today." I approached Lisa's cell, had her move to the front of the cell and cuffed her hands behind her before opening her cell. I know it sounds like I was afraid of them, but (I have a third degree Karate Black Belt) I really just didn't want to risk having to hurt them (at least unintentionally).

I moved Lisa over to the same low bench I had put Debbie on yesterday, stretching her out on the bench face up as I positioned her to my satisfaction. Her tits were still just a bit red from yesterday -- "No matter, we can fix that", I thought. Next I secured her hands above her head, used the spreader bar to spread her legs widely and locked everything firmly in place. What a sight! My bitchy ex-wife spread open, not going anywhere and available for however I wanted to use her. Lisa was very nervous. Obviously she was going to get a whipping, she just did not know where and how severe. She was right -- but her timing was off; after all anticipation heightens any experience.. 

The first thing I thought she needed was decoration. For whatever reason, defiance or just lack of time, she had not shaved her pussy like she was supposed to. Therefore I spent the next thirty minutes pulling out each little individual hair with a set of tweezers. I really loved her yelps every time I jerked one out. I especially loved dealing with the few fine hairs around her ass hole. Once she was smooth, it was decoration time. In a trip to the local sex emporium, I had bought two sets of gold slave rings (among other toys.) I now told her how I was going to pierce her clit, her nipples and the lips of her cunt and install the gold rings. Lisa whimpered as I went to the side cabinet and got my piercing device. This was a clamp with an attached needle-sharp piercing instrument, which screwed in as slowly as might be desired. To heighten her suspense, I decided to start with her nipples and work down.

Lisa moaned as I tightened the piercing clamp on her left nipple. I had sucked on it a bit first to get it erect, then immediately clamped it. It was too bad (for her) that it was still sore and sensitive from yesterday. I began to slowly screw in the piercing needle itself.

Lisa screamed as the needle began to have its way with her swollen nipple. When it was all the way through, I removed the clamp and quickly inserted the nipple ring, with Lisa moaning the entire time, begging me to stop. I repeated the procedure with the other nipple. Next, I went back to the cabinet for a small but hot torch. Using the torch, I quickly brazed the ring closures making the ring much more difficult to remove. Unfortunately, gold is an excellent heat conductor, so as I heated the rings, Lisa shrieked as her nipples were cauterized from the inside out.

Next I moved down to her cunt. I repeated the same procedure with each of her fleshy outer cunt lips. As I pierced and cauterized each cunt lip, the shrieks grew louder and the begging and pleading was virtually non-stop. By the time I got to her clit, Lisa was hysterical, begging me to do anything, fuck her ass, fuck her face, anything except pierce her clit. I failed to see her bargaining chips - I planned to do all that anyway.

Finally, accompanied by one last loud shriek as I brazed the clit ring closed. I was finished with her piercings. I stood back to admire my work for a minute, but only that. I had a lot planned for today. I tossed three nylon lines over the overhead beam, clipping one end of each to the clit and nipple rings. I pulled the free ends of all three tight and tied them off. This had the effect of stretching her clit and nipples straight up, with a fair amount of tension on each. Last, I clipped lines to the rings in her cunt lips, attaching each to a side of the bench, spreading her cunt wide open.

At this point I had a decision to make. Fuck her now, then whip her, or whip her and then fuck her very tender cunt. I just couldn't decide, until I remembered Debbie in the other cell. She had been sobbing quietly throughout Lisa's ordeal and I quickly brought her out, cuffed her hands behind her and pushed her to her knees between Lisa's spread legs.

"Now Debbie," I began, "I am going to give you a chance to help Lisa. I am going to start a timer and fuck your ass. However many minutes it takes you to make me cum, that is the number of whip strokes Lisa will get to each nipple, her cunt and her clit. You may want to try loosening up as I go in and tightening up as I pull out to make me cum faster. In the meantime, you can eat her out while I fuck you."

Without any more preliminaries, I knelt behind Debbie, greased up my cock and, with one long stroke, shoved it home all the way into her tight little asshole. I had reached forward as I impaled her, shoving her face down into Lisa's spread cunt, so her scream was somewhat muffled. I was super hard from working on Lisa, but I had come a lot yesterday so I was pretty sure I could last at least a while. I lasted longer than I would have thought, and it was a full twelve minutes until I grabbed Debbie's hips, shoved all the way in one last time and exploded in her ass. Surprisingly, she had tried to take my ass-fucking advice, even though she gave a muffled groan each time she felt the added friction when she tightened her little ring on my out-stroke.

I stayed all the way in for a couple of minutes, then slowly pulled out, listening to her sobs as I watched my cream dribble out of her distended asshole. It is really amazing how much a hard cock can stretch that little ring. Frowning, I noticed a speck of brown on my dick.

"I guess you weren't serious enough about the enemas", I told Debbie. "We will have to demonstrate a proper enema in the morning." I grabbed her hair, turned her around and shoved her face into my crotch. "Clean up this mess -- you have earned both of you another punishment tomorrow for your sloppy enemas." Frightened, she took my softening dick in her mouth and cleaned me thoroughly, afraid of the consequences if she didn't. 

As she sucked me clean, I started thinking about Lisa. While I was screwing Debbie's ass and she was supposedly going down on Lisa, I had not seen Lisa come. So I decided to play another little game. I quickly moved back to the cabinet and took out a set of monitor patches like are used in an EKG. However, these had been developed by a sex clinic to monitor orgasms. Properly attached, they indicated when someone had actually climaxed. I attached them to Lisa, and turned on the remote monitor.

"Now Debbie," I started, "while you were going down on Lisa, she didn't climax. So we are going to have another little contest. You will go down on Lisa. At the start, you each have earned 12 strokes with the whip. For every minute over six she holds out, you get two extra strokes and hers are reduced by two. For every minute under six, you get two less strokes, and she gets two more. Since she is already spread, the placement of her lashes should be obvious. Your lashes will be on the tender little asshole sticking up as you eat her." I pushed her face down onto Lisa's spread cunt and fastened lines to her collar ring to hold her in place.

"Ready, set, Go!" I called starting the stopwatch I had also taken out of the cabinet. Debbie immediately started licking Lisa. You could tell they had done this before, but unlike most times, this time Lisa was trying not to come and Debbie was trying to force her to. Maybe the position was getting her hot, but after only three minutes, Lisa started squirming around and Debbie redoubled her efforts. After another minute, Lisa screamed (she was always noisy) and came, the fact confirmed by the monitor. 

"Great" I said. "That was four minutes. That means Lisa gets 16 strokes and Debbie only 8. We'll do Debbie first, since she is already in such a nice position." I got my favorite, single-strand whip from the cabinet and positioned myself behind Debbie. I swung hard, trying to make sure the lash caught her right on her little asshole. Debbie shrieked into Lisa's cunt as the whip landed. The shrieks turned to screams, and the screams to sobbing as stroke after stroke landed on one of the most tender parts of her body. After the last stroke, I unfastened her and pushed her back into her cell, where she lay (face down I noted) on the bed, sobbing.

Now it was Lisa's turn. I decided to continue with the same whip, since I could accurately target it at small areas, such as nipples and clit. I started with her nipples. She had 16 strokes coming so I decided on four to each nipple, her cunt and her clit. The whip cracked loudly on her right nipple. Her scream was louder, since, unlike Debbie, her face wasn't buried in a cunt. Her voice got more shrill as each stroke landed. By the end of the last nipple stroke, I was again rock hard and needing relief. Another game came to mind. I gave her a first stroke to her wide-spread cunt, followed quickly by one to her stretched-up clit. The shriek from the last stroke seemed to bounce off the walls. I guess after the orgasm Debbie gave her, she was extra-sensitive.

"Now Lisa," I said, speaking louder to cut through her sobs, "you have another six strokes left, three on your cunt and three more on your clit. I will let you try to win those strokes back. If you can suck me off in less than five minutes, I will stop. If I last over five minutes, you get two extra strokes for each minute. Do you want to play, or should I just get on with it.

Lisa stopped her sobbing long enough to choke out "play".

"Good," I said. "I will give you a minute to recover and then we can start." I moved over to the bar, poured myself a bourbon, added a couple of ice cubes and took a couple of sips. I set it down and then moved back to the bench, stopwatch in hand. I positioned myself over her, straddling her face and feeding my erect dick into her mouth. "Ready, begin" I said starting the watch.

This was probably the best blow job I had ever gotten from her. Although she had only limited movement, she still tried to force my cock all the way down her throat, licking, teasing the pee-hole, whatever she could think of to make me cum quicker. Unfortunately, since I had already fucked Debbie's ass once today, that was not easy. Still she tried hard. At the four minute mark, I was getting close and barely hung on to the five minute deadline before exploding in her mouth, and covering her face with cum as I pulled out.

"OK," I stated, "good effort but it took just over five minutes. I won't give you any less strokes, but at least you do not get any more." Lisa sobbed. "Tell you what," I continued, " instead of three each on your cunt and clit, I will offer you two each on your cunt and clit, and two on your ass -- just to spread them out more -- your choice."

"I guess -- spread them out" was her halting reply.

She again shrieked when the first stroke landed on her spread cunt, snapping wetly on the tender inner lips. Her shriek rose in volume as the next stroke caught her clit. By the second stroke on her cunt she was again just sobbing and the volume increased after the final stroke to her clit. I swear I could see her clit throbbing after that stroke. I unfastened her from the bench and moved her over to the low wall we had used yesterday, again securing her in place, head down and ass up.

Like I had with Debbie, I took careful aim to make sure the whip tip cracked exactly on her little asshole. I was particularly mindful that I only had two strokes to get it right. Fortunately (for me) my aim was good and both hit her right where I wanted. I went back and sipped some more of my bourbon, to give the shrieking and sobbing time to die down. When it was quieter, I moved back to her head, and presented her with my firm but not yet hard again cock. "Get me hard so I can fuck you. When I am done, we are through for the day," I promised her.

When I was fully hard and reasonably slick with her saliva, I moved back around to her bottom and knelt down, resting my hard dick directly on her now bright red and swollen star. She gasped loudly and tried to flinch away at the contact, a measure of how tender her little asshole really was after the whipping. I pushed slowly forward, wanting to savor every moment of her ass-fuck. She screamed as I began pushing and grunted loudly as the head finally popped past her sphincter and I kept pressing slowly forward, taking my time. I began to pull back out until just the head was still buried in her butt and then rammed all the way in with one fast stroke. I continued this way, alternating slow and fast strokes, for at least fifteen minutes. Lisa whimpered continuously, gasping and groaning with each insertion. 

However, all good things must end, and I finally felt myself getting ready to let go. At that point, I pulled out and moved back to her mouth for more lubrication. As usual, she really did not like putting my cock in her mouth when it came straight from her ass, but she did it without protest. I guess she was either desperate for more lubrication or afraid I would go back to using the whip. After a couple of minutes, I went back to her ass. This time, as I got closer, I began to thrusting harder and faster, really slamming into her, before finally cumming one more time. I shot and shot, feeling her ass get more and more slippery as I continued thrusting deep until I finally stopped, fully embedded. I just savored the moment. Finally, I pulled out, went back around to her head and I forced her to lick me clean until I softened fully. I then freed her, removed cuffs and the spreader bar and took her back to her cell.

For a treat, I gave them a late lunch before deciding I wanted one more shot at Debbie. I pulled her out of her cell, cuffed her hands behind her, forced her to her knees and proceeded to really fuck her face. Since this was my fourth time today, it took over twenty minutes for me to cum, By that time, I am sure her throat was raw from the force of my fucking, since I was forcing her to deep-throat my eight inches on nearly every stroke. I did not cum as much, although it was still enough to make her gag. Finishing up, I uncuffed her and shoved her back in her cell, finished for the day.

I went out and brought back their dinners and slid them into the cells through the little doors at the bottom. Dimming the lights, I called "Good night ladies, sweet dreams. I will see you both again in the morning. By the way, tomorrow is 'Competition Day'."



Really Just Desserts Day 03



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.

Individual Competition Day

The two girls in the cells groaned as the lights came up and "Reveille" once again blared out of the hidden speakers. I stood in the doorway and watched as they jerked up out of their beds and moaned with the sudden movement. I like to think they were somewhat sore from the previous day's exertions; after all for the past few years they weren't used to a hard cock invading their private portals.

"Today is different," I advised them. "Yesterday it was obvious that Debbie was not taking her enema duties seriously, so before we do anything else, we need to take care of that. Since it is Debbie that needs the instruction, we will start with Lisa and let Debbie watch. Then you will both be punished for her lapse."

I hauled Lisa out of her cell and moved her toward a new apparatus. It had started life as a "ab" exercise machine, but was now something else entirely. I fastened her legs to the upright frame, then bent her over at the waist and fastened her upper body down at about a 45 degree angle to the lower portion of the machine. This left her cute little ass sticking out and ready for my ministrations. I started with an adult enema syringe and a quart of warm water. First, I used some Vaseline and my finger to loosen her asshole up, playing with her tight little ring for several minutes while she made embarrassed noises. Despite having been fucked a couple of times now, her little star was still tight enough to grip my finger tightly as I slowly pushed its entire length into her ass. I then proceeded to squirt syringe after syringe up her bowels until the entire quart was empty. There was the expected bitching and moaning as I did this, until I threatened to leave her there until she shit herself unless she shut up. She shut up. When the quart was empty, I released her and let her hobble back to her toilet and empty her bowels. I am sure she thought this was over, but of course we were just getting started. After she flushed the toilet, I brought her back out and re-fastened her to the apparatus. Next I wheeled over a stand with a one-gallon enema bag attached. Contemplating her ass, I moved back to my wall cabinet and brought out the next indignity. This was an anal plug, but with a hole in the center with a hose bib on one side. There was also a shut-off valve on the outside bib. Greasing it up, I slowly forced it into her ass, her moans loud as the widest 3-inch part stretched her little star. The wide front part finally stretched her ass enough to pop in, the narrower center part holding it tightly in her ass against the wider parts on each end. Next I attached the hose from the enema bag, opened the valve and listened to her groan as her ass was filled to what would be overflowing if not for the valves. Finally, I shut off the valve and disconnected the hose, leaving her there with her ass full and no way to relieve it. She started in whining, but I ignored her.

Next it was Debbie's turn. I repeated the same sequence with her, although she was much more apprehensive, having watched Lisa's ordeal. I think her embarrassment was greater since she was definitely not used to having a man finger her anywhere, let alone in her most private opening.

With both of them bent over, full of water and asses out, I thought it was time to administer some punishment. Using the multi-strand whip, I flogged them both, hoping that at least one of them would overcome the ass-valves, so I could make the other lick it up. They must have clenched their asses tight, because they didn't leak at all, even when I used an underhand stroke to hit their cunts directly.

Giving up, I freed them one at a time and put them back in their cells to remove the plugs and empty their overfull bowels. I went out, got their breakfasts and advised them to clean the anal plugs thoroughly, eat and get their showers over quickly.

Twenty minutes later, I was back. "Today is the first of two competition days," I advised them. "Today is individual competition, tomorrow is team completion."

I brought them out, again one at a time, sitting them down and chaining their legs, wide spread, to a leather sofa. Next, I attached the orgasm monitor leads to each of their bodies. Finally, I freed their hands and gave them each a clitoris vibrator.

"The competition is to see which of you can bring herself to a clit orgasm the quickest. As you would expect, the loser earns punishment," I told them. "Ready, set, go."

At first they were both reluctant, but a few snaps of the whip on their bare nipples convinced them to compete. Once they started, both were frantic to win. After only five minutes, the monitor confirmed what Lisa's shriek had already told me. She had indeed climaxed. Well, she always was a slut.

"OK, Lisa wins that round," I said, taking the vibrator away from Debbie, who at this point, having worked herself up, was frantically trying to cum. 

I went over to the bar and fixed myself a bourbon while they calmed down.

Next I handed them two eight-inch vibrators. "This time we are competing for a vaginal climax," I advised them, "with the same rules, loser earns punishment. Ready, set, go."

It was really no contest. Debbie had been almost ready to cum before, and Lisa had just cum, so Debbie easily won this round in less than three minutes.

"So, Debbie wins that round. Final round," I advised them, "Anal climax. Use the vibrators in your ass until you cum. You can lube it up in your pussy, but that's all. If no one cums in thirty minutes, you both get punished. Ready, set, go."

This was hard for them. I sat and sipped my drink as I watched them struggle. First they didn't really want an eight-inch vibrator up their ass. Next, I doubt either had ever had an anal orgasm. Still, they struggled mightily, using one hand on their clits and pussies while the other shoved the vibrator deeper into their asses. Unfortunately (for them), at the thirty minute mark neither had cum, although Lisa was getting close. "Time," I advised them, taking the vibrators away and clipping their hands back to rings in the sofa arms.

"So, each of you has earned two punishments. However, since I am now horny, I will give one of you a chance to win back one of your punishments. We will have a timed deep-throat contest. Whoever gets me completely down their throat the fastest and keeps it there for 15 seconds, wins."

I went to the cabinet for the stop watch, stepped up in front of Debbie and unclipped one of her hands. I thought she might have an advantage since I had already face-fucked her twice, going almost all the way in. Lisa, on the other hand, had never even managed to deep-throat me once in the years we were married. I started with Debbie, since if she posted a good time, I thought it might give Lisa more incentive.

"Now Debbie, I will let you take this at your own pace, but remember you are being timed. You can use your free hand to pull me closer when you are ready for more cock. You have to get me in all the way in and hold it there for 15 seconds before the timing stops. We will keep timing until you finally succeed. If you are ready, open wide and I will start the timing."

Debbie opened her mouth and reached her free hand behind me to pull me quickly closer. I think her strategy was to try to take me all in on the first thrust. However, she choked, gagged and pushed me back when I still had a good two inches to go. The sudden tightening of her gag reflex felt great on the head of my cock. After her breathing settled down, she settled in for the long haul. On her third attempt, she finally got me all the way in, but immediately started gagging and pushed me back out. It took her several more attempts to finally succeed, although she got to the ten-second mark twice before finally controlling herself enough to last the required 15 seconds. Her throat spasms as she struggled to control herself almost made me cum. Her time would have been better if she hadn't had to pause so long to get her breathing under control after each attempt.

"Debbie, your time was four minutes and 53 seconds, so that is Lisa's time to beat," I noted. I re-clipped Debbie's free hand to the ring and moved over in front of Lisa, unclipping one of her hands. "Same procedure, Lisa. I will start the timer whenever you are ready."

During our marriage, blowjobs had always been delicate things for Lisa. I don't think she ever took more than three or four inches in her mouth, mostly just concentrating on the head while using a hand to jack off the shaft. This was going to have to be different. Lisa apparently had learned something from Debbie, since she started out with deep breathing (or maybe she was just nervous) before signaling me she was ready by opening her mouth and pulling me forward. Her technique was better. She started with what she could comfortably take and then started slowly working her way down my shaft. However, when she hit the six inch mark, she hit a wall, choking, and just couldn't force herself to take any more. She kept trying, but as the time mark passed, she had only managed to get another inch or so in.

"Lisa, it looks like you lose. You will still get two punishments whereas Debbie will only get one. However, before we get into that, you still have to deep-throat me for at least the required fifteen seconds." I unfastened her from the sofa and moved her over to the low bench we had used before, securing her on her back with her head hanging off the end. Flipping a switch, I raised the bench until her head was just at cock-height. Next I went back to the cabinet and brought back a ring gag. Holding her mouth open, I forced the gag in so that her mouth was held wide open, leaving me a wide opening to fuck through. I was now ready to proceed.

Lisa's position left me a straight shot down her throat, so I proceeded to slowly face-fuck her, going a little deeper each time. The throat spasms came and went, gradually stopping as she finally came up with a breathing -- swallowing technique that worked to let me all the way in. I finally bottomed out and began a slow deep-throat fuck. I kept this up for several minutes before finally shoving my cock all the way in one last time and holding it there as I unloaded shot after shot down her throat. This brought the gagging, choking and throat spasms back, but at that point I couldn't have cared less. I pulled out and removed the ring gag, Lisa coughing and crying all at once. "Good job," I congratulated her, "I knew you could do it."

I left her there as I moved over to the bar and poured myself another drink. I needed to decide on the punishments for each of them. Unfortunately for her, since Lisa had two punishments to endure, I felt I need to start with her. Thinking about it as I sipped my drink, I finally came to a decision. I unfastened her from the bench and moved her back to the familiar low wall. As usual, I spread her legs widely and secured them against the wall, bent her body forward and secured it to the inclined board. Again I secured her hands above her head. I moved around to her head so I could watch her face.

"As I mentioned the first day, I have a fucking machine. Since this is your first time, we will do a drawing for the size attachment and the hole it goes in. Just to be fair, I will let you decide how the drawing works. Currently I have 7, 9, 11, and 13 inch attachments. If you want, we can draw from all four. Who knows, you might get lucky and get the 7 incher. On the other hand, I will agree to remove both the 13 inch and 7 inch attachments, leaving the choice between 9 and 11; it's your choice, but remember we haven't selected the time or your opening yet. You may not want to risk having an electrified 13 incher hammering in your ass for the next hour."

Lisa had been sniffling quietly the entire time and I admit, I did feel a little sorry for her, so I decided to throw the opening drawing to spare her already abused ass. "Well, Lisa, shall I remove the high and low attachments or go with all four?"

Lisa quit crying and appeared to think for a moment, trying to decide how lucky she felt; given her current position, probably not too lucky. "I guess remove them," she decided. 

"Good choice," I said. "Just to see if you made the right choice, we will draw from all four, but the 7 and 13 inchers won't count." I reached into the box and drew out a size slip. "Lucky you," I said, showing her the 13 inch size slip. "Clearly you made the right choice." The next drawing was the 11 inch slip. "I guess your luck only goes so far," I commented. "Next we will draw for opening. I reached into the second box and pulled out a slip. "Ass" it read. "Your luck is back, I drew 'Cunt'," I lied. "Now for the time drawing. We have 15, 30, 45, and 60 minute time slips. Do you want to eliminate the top and bottom again?"

"I guess," was her reply.

I reached in the third box, drew a slip and showed it to her. "Not bad, only 30 minutes," I commented.

I moved the fucking machine over, adjusted the height and length of stroke, making sure that it hit her open pussy squarely and would go deep enough to completely bottom out. Lisa groaned loudly as her cunt was stretched around the 11 inch cock as it entered her fully so I could adjust the stroke. I adjusted it so that it would pull all but the last inch out and then would shove forward until it bottomed out solidly against her cervix. As mentioned earlier, the punishment attachments have metal rings running around them and a flat metal collar which can administer nasty little shocks to various parts of the victim. I adjusted the collar so that it was flat against her clit and cunt lips when the cock was fully embedded. As usual, I hung weights from the rings in her nipples, but since this was punishment, I also attached electric leads to the rings, so that she would get shocks there as well. When all was ready, I stepped back to admire the scene. As I looked, I thought of one more refinement. I brought over the orgasm monitor and attached the leads to Lisa's stretched-out body.

"The machine and the shocks will both start slow, but gradually pick up speed as time goes on. By the end of 30 minutes it will really be hammering you. Also, the shocks will come quicker and last longer as time passes. They don't really get any stronger; it just feels like they do. However, because I am such a nice guy, I have decided to give you a chance to shorten the punishment. If you orgasm before the 30 minutes are up, I will stop the machine," I advised her.

I moved to the fucking machine, set the timer and flipped the start switch. Lisa groaned as the 11 inch monster began moving relentlessly in and out of her cunt, and then shrieked as the first shock from the collar hit her clit and pussy lips.

I turned the sofa around so that Debbie could get a better view, then sat next to her, sipping my drink and fondling her nipples and cunt as I watched the show, listening to the squishy sounds of the fuck, interspersed with the moans and the shrieks from the shocks. Life was good.

If it hadn't been for the shocks, I am sure Lisa would have climaxed quickly. As it was, whenever she started climbing her peak, a nasty little shock would bring her back down. I especially like watching the shocks to her nipples, since her sudden jerk would really set the weights swinging. Debbie was squirming around under my touch, but I had two fingers completely buried in her cunt and was slowly stroking in and out when the timer finally went off and the machine stopped.

I got up, removed all her attachments, unfastened Lisa from the bench and put her back in her cell. She lay on the bed, alternately panting and moaning, her hands covering her sore, stretched-out nipples and her sore cunt.

Next it was Debbie's turn. Since Lisa had experienced the "gravity fuck" on the first day, I thought it only fair that Debbie get her turn. I attached her wrist cuffs to the overhead rope in the corner and hoisted her up until she could barely reach the floor. Next, I retrieved the spreader bar and attached it to her ankle shackles, spreading her wide., I next attached a second line to the bar, ran it through the ring on the overhead pulley her wrists were clipped to and then pulled it up until her legs were almost even with her arms. I secured it there and stepped back to admire her position. This position left her ass and cunt as the lowest points of her body as she hung there. I retrieved my "opening" selection box, showed it to her and drew out a slip. I showed her the slip reading "ass" and sadly shook my head. "Not your lucky day so far," I said, adjusting the rope so that her ass was now the lowest point. Next we drew for size. I gave her the same choice I had given Lisa, but she turned it down. The slip I drew read "13". I showed it to her and commented that she should have taken my offer. I installed the huge 13 inch dildo on the stand, greased it up thoroughly, moved the stand over beneath her and carefully lowered her, lining the tip of the dildo up with her tight anal opening, then lowering her a bit more until the tip penetrated her soon-to-be-enlarged ring. Debbie whimpered all the while and then shrieked as the wide tip finally popped into her tight little ass. Next, I rolled the battery charger over and attached leads and clips to both of her nipples, her clit and each inner cunt lip. The last electric lead and the control wire I attached to the dildo.

Preparations complete, I stepped back to check it all out. Deciding we were good, I let some slack out of the rope and watched her twist and groan as the dildo began to have its way with her ass. I retrieved my drink and took a seat on the sofa to watch the show. Every few minutes, I would let out more slack and watch the dildo slide deeper into her ass. Like Lisa, as she began sliding further down the monstrous intruder, she would try to pull herself up by her bound wrists. This would only last so long before her arms would tire and she would slide back down. In the meantime the random shocks to all her sensitive places had her jerking and screaming. Every time the dildo in her cunt fired, her reflex would try to jerk her up, only to slide back down, deeper than before. By the time twenty minutes had passed, she was completely worn out, just hanging there, impaled on the dildo and moaning, eyes closed, as the dildo slid deeper and deeper into her butt. To revive her, I let out the rest of the slack all at once and watched her eyes fly open wide as the widest part started really stretching her ass. She began screaming and frantically jerking herself up, but gradually gravity won and she slid the rest of the way down until she finally hit the off switch.

I left her like that while I finished my drink, then got up, hoisted her off the dildo and freed her. I had to support her as I led her back to her cell, then left her face down on the bed. Her poor asshole was so dilated that I could have stuck my entire thumb in without touching the sides. Looking at her stretched-out asshole, I wondered if it would ever recover, then decided it probably would, and if it didn't, that was her problem.

Lisa was very quiet when I pulled her out for her second punishment, obviously afraid the same was in store for her. Instead, I forced her to her knees, clipped her wrists behind her back and told her it was time for another deep-throat session. I told her I would time us and she would earn one stroke per minute until I came. With that, I started the watch and began thrusting into her mouth. I was able to get all the way down her throat after only a few tries and I kept that up until, after about eight minutes, I again pushed all the way in and held it there, my dick gripped tightly by her throat muscles, as I came down her throat.




Really Just Desserts Day 03



Next, I dragged a mat over to the rope area in the corner, laid her down on it and clipped two overhead ropes, spaced wide apart, to her ankle cuffs. I hoisted her up, alternating each rope as she lifted. Because the ropes were set six feet apart, as I hoisted her up, her legs were spread widely, leaving her poor little cunt exposed. Satisfied with her position, I retrieved a new toy, a thin riding crop, and slowly began her eight strokes, trying to make sure I hit her cunt and clit dead center with each stroke. The whippy crop made very satisfying cracks each time it connected. She did shriek a bit, but not as much as she would have two days ago. After every stroke, I would finger her abused cunt to see how wet she was getting. 

Finishing up, I let her down enough so that her head and back were flat on the mat, but her legs were still raised. I had decided I was ready for one more climax, so I fucked her missionary style as she lay on the mat with her legs in the air. Since I had cum not long before, this was a long, leisurely fuck. When I got close, I pulled out, moved around and came on her face, covering her from chin to forehead.

Finally I released her and put her back in her cell. Feeling charitable, I tossed a tube of "Preparation H" to Debbie, went out and got their dinners, then dimmed the lights and walked out. 



Really Just Desserts Day 04



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."



Really Just Desserts Day 05



Really Just Desserts – The Final Installment

Note: To understand this story you should really read at least the first installment.  Chapters 2, 3 and 4 can be read separately, but this final Chapter really needs Chapter 1 to make sense.

I had been pleased with the overall situation over the past four days, and to be honest, was starting to feel a little sorry for the girls.  So I decided to let today be more about fun for me than punishment for them.  I actually let them sleep in, then brought their breakfast and let them cleanup after they woke up.

The first two scenes were already worked out in my (admittedly evil) mind.  I had each girl draw a number from the first selection box.  “Lowest number goes first,” I informed them.

Debbie drew a seven, Lisa drew a four. “It looks like Lisa is our first today,” I noted.

I had set up a rope coming down from the ceiling in the center of the room, attached to a rotating wheel from a short shaft sticking down.  The speed and rotation direction of the wheel could be controlled by a hand-held remote control.  As the wheel turned, the rope would spool up on the shaft, essentially shortening the rope.  I attached a “chair” to the rope.  The “chair” consisted of a back and two wide straps, but no seat.  By adjusting the lines attached to the back and the outside ends of the straps, one could adjust the angle of the missing seat so that different sections of the body in the chair would be the lowest point.

I brought Lisa out and strapped her into the chair, then hoisted it up.  I had her draw from the second selection box one of two slips, reading either “cunt” or “ass”.  She drew “ass” and I adjusted the seat back line so that her little butt was the lowest point as she hung there.  Next I moved a mat under the chair and positioned myself on the mat directly under the chair, with my hard cock sticking up.  I noted the distance and the adjusted the main rope so that when it was totally unwound, Lisa would be completely impaled on my dick. 

I lay back down, greased my dick with Vaseline and seated myself all the way into her butt with one hard stroke.  When I was satisfied that I was all the way in, I set the bottom stop on the control.  Lisa grunted as I impaled her tight little butt, and panted a bit as I shoved myself home, but was otherwise quiet.

I started up the machine.  It began to turn, spinning her about on my dick even as the rope spooled up, raising her gradually up.  When just my tip was still imbedded, I set the top stop on the control and moved it to “oscillate”.  This made it automatically reverse direction until it hit the bottom stop, then reverse until it hit the top stop.  “Isn’t technology wonderful,” I thought then settled down to enjoy the ride.

The sensations on my dick as Lisa’s tight little ass spun around on it, first one way, and then the other, now all the way in her butt, now barely in at all, were just unbelievable.  After a few minutes Lisa began squirming around, trying not to cum.  I like to think this was almost as good for her as it was for me.  Certainly she came hard enough when she finally climaxed.  However, all good things must end.  Since the machine started slow, only gradually speeding up, I got to enjoy this mind-blowing ass-fuck for almost twenty minutes before I finally shot off deep in Lisa’s little ass.  I shut the machine off with my softening dick completely buried and just enjoyed the moment.

Finally I raised Lisa up, my soft dick popping out of her hole, and took her down.  As usual, I had her clean my dick with her mouth then put her back in her cell.  I took a break to give my dick time to recover.

An hour later I was back.  This time it was Debbie’s turn in the chair.  I set her up as I had Lisa, only adjusting the lines so I could enter her cunt, rather than her ass.  I made all the adjustments and settled back to happily enjoy another mind-blowing fuck.  Because I had already cum once, this time it was even longer.

A few minutes in, Debbie, like Lisa, began to squirm around in the “chair”.  Eventually she began to pant and then climaxed loudly.  The machine spun on.  Despite not liking men, she climaxed three more times on my dick, before I finally lost it as well.  I have to say that the contractions of her cunt on my dick each time she came almost cut my enjoyment short as I tried to resist cumming.  Finally on her fourth time I could not control myself and unloaded in her tight little cunt.  Like Lisa, I stopped the machine when Debbie was all the way down enjoying the warm aftermath as I felt our combined juices running onto my crotch.

Finally I raised her up, extracted myself and took her down.  After she cleaned me up with her mouth, I put her back in her cage and took another break.

After another hour, I was back again.  For the final scene, I had something different in mind.  I brought Lisa out and chained her down, face up on the mat right under the chair with her arms and legs tightly spread.   Next I brought Debbie out, fastened her arms behind her back and chained her by the ankles in a kneeling position just back from Lisa’s head.  Finally I brought the electric shock machine over and positioned the electrodes.  Since there were only six circuits and two girls, I chose the nipples and clits as the most effective places for the electrodes and attached them.  Next I carefully adjusted the chair and climbed into it.  I had positioned it so that my ass was the lowest point, directly over Lisa’s mouth.  This left my dick sticking out for Debbie to suck.

“It should be pretty obvious what I want,” I advised them. “I want Lisa to give me a nice rim-job, getting her tongue as deep in my ass as she can, while Debbie deep-throats me.  If I am not satisfied with your efforts, I will use the remote control to administer the shocks you are both so fond of, so I suggest you make your efforts enthusiastic.”  I gave them both a warning shock to get them started and then relaxed to enjoy their attentions.

This exceeded even my expectations, so I never had to use the shocks at all.  I had never had a combined blow-job and rim-job at the same time before and the combined sensations were just incredible.  Lisa was alternating licking all around my ass with thrusting her tongue at least an inch deep in my butt.  Meanwhile Debbie was gamely taking me in, short fast strokes and licks at my pee-hole alternating with slow deep strokes until my cock was completely buried in her throat. 

Since I had already cum twice, this went on for over thirty minutes before I finally grasped Debbie’s head forcing my cock all the way down her throat one last time.  “Bury your tongue in my ass,” I yelled at Lisa, then unloaded an incredible load straight down Debbie’s throat.  I released Debbie and she gasped as she came up off my impaling dick, panting a bit to regain her breath.  I gave her a minute then had her lick me clean and extracted myself shakily from the chair.

I released the women and put them back in their cells.  I advised them to clean up and actually gave them clothes to put on and then went out and I cleaned up myself.

Next, I brought down their dinners and even opened a bottle of wine for them so they could celebrate their coming freedom.

Of course the wine was drugged and a few minutes after finishing their dinners they were both fast asleep on their cots.  The same gang that had originally kidnapped them came in and loaded them each into a large trunk.  These trunks were then taken to a large, fast power yacht I had bought and they were loaded with the rest of the supplies for a purported deep-sea fishing trip in the Gulf of Mexico.  Once aboard, they were unloaded and placed onto a double bed in a locked cabin.  Finally ready, the yacht left the marina, heading out across the Gulf.

At the same time, an identical yacht, which I also owned through a shell company, left the Cayman Islands on its own “deep sea fishing trip”.  It also headed straight out in the opposite direction, rounding the tip of Cuba and entering the Gulf as well.  The girls actually did not entertain the crew, since they were sea-sick most of the first day.  The medicine they were given was also drugged and it was relatively easy to raft up the two boats in the middle of the Gulf and transfer the unconscious women from one boat to the other.  Both boats then turned around and headed back to their respective marinas.  This whole shell game was just so that when later the girls claimed to have been taken by boat to the Cayman Islands, the US boat would have a perfect alibi, since clearly the boat did not have time to make it all the way to the Caymans and back in the time it was out.  I was setting the stage for their stories to fall apart.

Also unknown to them, two women made up to look a lot like Lisa and Debbie had used their passports to make a trip to the Caymans.  They had been staying at a secluded villa with little outside contact for the past week.  When the boat carrying Lisa and Debbie docked, it was met by a courier with their passports.  In the meantime, the two women used their own passports to check out of the villa and leave the islands under their own names.  

When the boat docked, their passports were delivered to Lisa and Debbie along with two suitcases.  They were told to pack the clothes I had bought for their trip into the suitcases, given the promised $10,000 each and driven to the airport.  Next, they were put on a private charter to Mexico and told that after that they were on their own.  The plane landed in Mexico at Veracruz, unloaded the women and their luggage and immediately filed a new flight plan and left.

Debbie and Lisa took their suitcases and cleared customs, taking a cab to the hotel that had been reserved for them.

They checked into the hotel and immediately went up to their room, relieved that their ordeal was finally over.  Their plan was to rest and then immediately take a plane back to the states and call the police.

Unfortunately for them, there was a pound of cocaine hidden in each suitcase.  Also unfortunately, Mexican customs had been tipped off.  This was typical, one gang informing on another to disrupt shipments.  The Mexican authorities gave it several hours but when no one met the women to take the drugs, finally decided to go ahead with the arrests.

Lisa and Debbie were totally nude and busy consoling each other when the hotel door burst open and the Mexican police burst in.  The drugs were easily found and both women were arrested, forced to get dressed under the watchful eyes of the Mexican “Federales”.

Of course they told their fantastic story to the Mexican police.  The Mexican police did not really believe them but asked US authorities to check the story out.  They actually got a search warrant for my cabin, which was a ramshackle affair I had deliberately not torn down and which had no basement.  They checked all large power yachts in the marinas but none had been out long enough to make a run to the Caymans and back, even at top speed.  They checked in the Cayman Islands and found that “they” had actually been staying there for the past week.  I also had testimony from numerous people who had seen me downtown every day, so clearly I was not up in my cabin abusing these poor women.  At my insistence, they even searched my fourth-floor penthouse apartment.

What they didn’t search was the third floor of my building which I secretly owned through another shell company.  By this time all the cells and equipment there were dismantled and removed anyway under the guise of building out the space for the new corporate owner.  

All of this was reported back to the Mexican police along with the US arrest warrants for their perjury at my trial.

Needless to say they were both found guilty.  A discrete bribe, readily accepted since I was not asking for something the judge was probably not going to do anyway, resulted in sentences of exactly four and a half years each, the same time I had spent in prison on their trumped up charge.  I did arrange, through another bribe, to allow them to spend their sentences in a US prison, on condition that, like in Mexico, there would be no parole.  

In the meantime, based on the new evidence of their perjury, I received a full pardon, and started work on my grand new cabin, with its large soundproof basement.



Really Just Desserts



I next moved over to Lisa's cage. My ex-wife was a five foot five brunette, slightly overweight but with amazing D-Cup tits and a cute little bubble butt. "Come over here to the front of the cage, turn around and put your hands behind your back so that I can cuff you", I demanded. "You need to clean up your lovers mess while it is still warm and then be punished for your earlier outburst."

"Fuck you" was her not altogether unexpected reply.

"As you wish", I replied, "but this time it will be in your cute, tight little butt." I used my hand control to trigger the shock collar around her neck. She convulsed and fell to the floor.

I unlocked the cell, cuffed her wrists behind her, and carried her over to the pool Debbie had left when her bladder gave way, dumping her face down on the floor. She moaned as the shock wore off. In the meantime, I went back to the cabinet and selected a short-handled whip with a single long braided lash that unbraided into multiple long lashes two feet from the end. Each braid was also knotted at the end to enhance the effect. Pacing back to Lisa, who was just beginning to stir, I brought the whip down hard on her rounded little butt. Each knot left a distinct much-redder mark at the end of the red welt left by the lash. She screamed and tried to get up and turn around, so I just slashed the whip across her tits, catching her left nipple with one of the wicked little knots. She screamed and jerked away from me, so I slashed her ass again. "OK, OK, no more please", she screamed. "Then obey me and start licking. Don't worry, urine is actually sterile and I cleaned the floor recently." I picked up the other lash I had used on Debbie and snapped it occasionally on her butt as she licked, causing a flinch and shriek each time it hit, even though it was a lot milder than the first whip. She finally finished and I refastened her wrists in front of her, clipped them to an overhead rope in the corner and hoisted her up until she could barely reach the floor. I cleated the rope off and returned to Debbie – it was time for me to fuck her tight little ass.

I was really looking forward to this for a couple of reasons. Back when Debbie was just a girlfriend coming over to visit Lisa, I had always admired, OK to be honest, lusted after her tight little ass, especially since Lisa would never let me have hers. Being married, all I did was lust - all that was changed now. Second, as promised, I planned to fuck Lisa's ass for the first time after I finished with Debbie. I figured fucking Debbie's ass and cumming for the third time today, would let me fuck Lisa's ass for a long time before I climaxed, no matter how excited I was over finally getting her ass for the first time.

Debbie was just as I had left her, not even squirming around much, although as tight as she was bound, she couldn't have moved all that much anyway. I hoped she was nervous with anticipation. I just had the anticipation. I knelt at her head, still holding the whip. "Are you ready for some real ass-fucking", I asked. 

She hesitated and then reluctantly whispered "Yes, Master". "Very good", I complimented her, "it looks like at least one of you is learning". 

Of course, the first order of business was to decide if she got just my cock, or my cock and the fucking machine. To heighten her nerves, I decided to draw for the attachment size first and then flip the coin to decide if I got to use it. Showing her a small open-top black box, I told her "This box has four numbers in it, 7, 9, 11 and unlucky 13. We will first draw a number to decide which attachment to use." I reached in the box, selected a tag and pulled it out. "Oh – 11 – not so good, but not as bad as it could be," I told her. I got up and retrieved the 11 inch attachment, brought it back and showed it to her. It was 11 inches long and fully 3 inches in diameter at the base. She didn't faint, but became a lot more nervous. "Now for the coin flip. Heads is good, but Tails, well the machine gets your tail" I smirked. I flipped the coin, and it came up heads. "Lucky you", I told her, showing her the coin.

I set the coin, the attachment and the box aside and presented my cock to her mouth. "Get me hard", I demanded. She proceeded to do a fairly good job, using her tongue as well as just sucking. I guess the earlier shocks and whipping had had the desired effect. After a couple of minutes I was beginning to revive and started some thrusting. This finished the job and in another minute or so I was fully engorged and ready to sample the cute little ass I had lusted after for so long.

Before starting I added one little refinement. Since her tits were sticking out on either side of the inclined board, I added alligator clips with rings to each nipple. As you would expect, she got out a short scream as I clipped each one on and the teeth bit into her already sore nipples. Then she just moaned as I hung small weights on each ring. These weights would swing as I fucked her, stretching out her nipples more and more each time I thrust.

I went around to her bottom and knelt down, resting my hard dick on her ass crack. She flinched at the contact. Deciding to be nice, I thrust my dick back into her pussy for a few strokes to get it wetter with our mingled juices. This accomplished, I spread her checks with one hand, using the index finger of the other to play with her puckered little asshole. She gasped as my finger finally penetrated her fully and moaned a bit as I moved it in and out. Deciding that was enough stretching (after all, I did want her ass as tight as possible), I decided against a second finger and pulled the finger out with an audible pop. Still holding her ass cheeks apart, I used my free hand to position my cock at her barely-stretched-out star and began slowly pushing.

She started breathing faster, almost hyper-ventilating, as soon as I began pushing, and yelped loudly when the head finally popped in. I could feel her trying to relax as I held still, with the head of my rock-hard dick just inside her most private portal. I could not believe how tight she felt, her little ass ring really squeezing my shaft just below the head. Before she could get very relaxed, I used one hand on each hip to really spread her cheeks and shoved with all my might, seating half my cock in one sharp thrust. She screamed shrilly and then again as my second thrust finished burying all eight inches in her virgin little hole. "Does that feel good?" I asked nastily. Before she could reply I began thrusting in and out with long slow strokes, gradually building up speed until I was really hammering her butt. Several times I pulled out to admire her widely-dilated asshole, letting it begin to close up before thrusting back in as hard as I could. The first couple of times I did this I got short, choked-off screams, but each time after that I at least got a shrill yelp. Mostly she was just crying, moaning and begging me to stop. After about 10 minutes of this I started to get close so I asked her if she really wanted me to stop. "Yes Master, please Master" she begged.

So I did. I pulled out, and went back around to her head. Holding her head, I thrust my soiled cock straight down her throat and began a series of hard strokes. She tried to recoil at first but then gave up as I held her head firmly and she even started using her tongue again, I suppose to get me to come as fast as possible. I had other plans, so after a couple of minutes I went back to her butt and shoved my dick back in her ass, which had already started to close up, accompanied by a new set of screams and moans. I did this twice more before I finally could not stop myself and exploded in her mouth, warning her to "Swallow it all, unless you want to be punished again." After she swallowed everything I had given her, I had her lick me clean until I softened fully. I then freed her, removed the clips, the weights and the spreader bar and took her back to her cell. She collapsed on the bed, crying and groaning, as I locked the cell door.

Now it was time for Lisa, who still had her punishment to be administered. Since she was being her usual nasty self, rather than the fucking machine, I decided to use something now that I had planned to use a bit later. I had had a large electrified dildo built with an off switch for the battery charger control incorporated right at the base. In theory, all you had to do to stop the shocks was slide your ass or cunt down the dildo until your body flipped the switch. Of course, since the dildo was electrified, 12 inches long and almost four inches in diameter at the widest part of the base, that was easier said than done.

Since I was planning on fucking her ass for the first time next and did not want it stretched out first, this time the dildo had to go in her cunt. I retrieved the spreader bar and attached it to her ankle shackles, spreading her wide. I next attached a line to the bar, ran it through the ring on the overhead pulley her wrists were clipped to and then pulled it up until her legs were almost even with her arms. I secured it there and stepped back to admire her position. This position left her cunt as the lowest point of her body as she hung there. I moved the dildo on its stand over beneath her and carefully lowered her, lining the tip of the dildo up with her opening. Next I rolled the battery charger over and attached leads and clips to both of her nipples, her clit and each inner cunt lip, as well as an electric lead and a control wire to the base of the dildo. I explained the setup to her, lowered her fully onto the dildo and flipped it on.

For the next thirty minutes, I sipped bourbon and watched. Every so often I would lower her by letting out more slack in the rope. Each time, as she began sliding further down the monstrous intruder, she would pull herself up by her bound wrists. This would only last so long before her arms would tire and she would slide back down. In the meantime the random shocks to all her sensitive places had her jerking and screaming. Every time the dildo in her cunt fired, her reflex would try to jerk her up. It was fun to watch and finally, as I felt my dick finally beginning to stir again, I let out the rest of the slack and watched her struggle against the inevitable slide down the intruder in her cunt. At this point she was screaming that it was tearing her apart and begging for mercy. I was unmoved. Finally, after her arms gave out and she could resist no longer, she slid the rest of the way down the dildo, bottomed out and her cunt flipped the off switch. I left her there for a minute listening to her groan before asking her if she was ready to be obedient. Her "Yes Master" reply was music to my ears, so I pulled on the rope and eased her body back up off of the dildo, which popped out of her sorely stretched cunt with a distinct plop. Next I removed all the clips and leads and inspected her cunt. Looking at how stretched it was, I was really glad I hadn't used her ass instead; maybe next time if she pissed me off enough

I unfastened her ankles from the pulley and let them drop to the ground. At first she was too unsteady to stand and was moaning as her weight came on her feet. As soon as she was steady, I unclipped her wrists and carried her over to the wall apparatus where Debbie had so recently been secured. 

She must have been really exhausted since she put up absolutely no resistance as I secured her in place. I secured her just like I had Debbie but, since she had bigger breasts, I naturally used heavier tit weights. She gave such a nice little scream when I put the clips on her nipples that I just couldn't resist swinging the weights with my hand and listening to her moan as her nipples stretched.

There are really no words to describe how much I enjoyed fucking her ass. Since she was secured and I had no where else to be, I took my time and to her humiliation, played with her ass for fifteen minutes or so, with my fingers, a small vibrator and other toys. I next used skin-bonding super glue to glue flat ring tabs on each check just outside her ass crease and attached elastic lines to each, spreading her checks wide and exposing her snug little portal, before securing each line in place to rings on the edges of the wall. This left her cute little asshole exposed and vulnerable to the whip, which I proceeded to use to great effect. I got really good at cracking just the tip of the lash right on the cute little ass ring I planned to be fucking soon. The screams each time I did this were really shrill, followed immediately by almost hysterical sobbing. Her jerking at each stroke had the added bonus of really making the weights on her tits swing, stretching her nipples big time. By the time this was finished, I was betting her nipples would be at least an inch long.

At last my cock began to get fully hard again, so like I had to Debbie, I knelt down and presented my cock to her mouth. "Get me hard", I demanded again. She proceeded to do a fantastic job, using her tongue on my shaft as well as swirling it around the head, teasing my pee-hole and just sucking for all she was worth. Despite worries about her ass, I think she was more afraid I would go back to using the whip on her little asshole.

When I was fully hard and reasonably slick with her saliva, I moved back around to her bottom and knelt down, resting my hard dick directly on her now bright red and swollen star. She gasped loudly and tried to flinch away at the contact, a measure of how tender her little asshole really was after the whipping. I pushed slowly forward, wanting to savor every moment of her first ass-fuck. She screamed as I began pushing and grunted loudly as the head finally popped past her sphincter gate. I think she expected me to ram forward into her like I had Debbie, but I just kept pressing slowly forward, taking my time. I took at least a minute to slowly impale her on my full length. Then, almost as slowly, I began to pull back out until just the head was still buried in her butt. I continued this way, only picking up speed very gradually, making every stroke a fully in and almost fully out exercise. She whimpered continuously, gasping and groaning with each insertion, but never begged me to stop, I suppose because she was sure there was no point. She was right, of course. At this point, including the six months we dated before marriage, I had waited over eight years for this; I planned to enjoy it to the fullest and there was no way I was stopping.

The relatively slow pace, plus the fact that I had already come three times, let me keep this up for almost forty-five minutes. After the first five minutes, I pulled out and re-lubed my cock, more for my comfort than for hers; she was just that tight. I alternated between re-lubing with gel and moving back to her mouth for lubrication. I could tell she really did not like putting my cock in her mouth when it came straight from her ass, but she did it without protest. I guess she was either desperate for more lubrication or afraid I would go back to using the whip.

However, all good things must end and eventually I felt myself getting closer and closer. I thought about cumming in her mouth, but I had done that before. For this first ass fuck, I decided I really wanted to finish in her ass. I began to thrust harder and faster, really slamming into her, before cumming one more time. Given that it was my fourth of the day, I was really surprised at how much I shot. I shot and shot, feeling her ass get more and more slippery as I continued thrusting deep until I finally stopped, fully embedded. I just savored the moment. Finally, I pulled out, went back around to her head and I forced her to lick me clean until I softened fully. I then freed her, removed the weights and the spreader bar and took her back to her cell. I left the tabs I had glued on her butt for future use.

I went out and brought back their dinners and slid them into the cells through the little doors at the bottom. Dimming the lights, I called "Good night ladies, sweet dreams. I will see you both again in the morning for more fun.

I left them alone and then proceeded to finish getting good and drunk for the first time in over four years, thinking happy thoughts about the next four days.