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.