Really Just Desserts Day 03byEvil_Teddy_Bear©
Note: These stories are pure fantasy. In reality I have been married for many years to a wonderful woman -- she just is not into B&D.
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.