17. Torture Weekend
Mistress was a sadist. There was no denying that. She derived great pleasure from causing pain to Her pet. She enjoyed his screams, She really enjoyed his tears, the sight of them, the taste of them, the very fact that She was the cause of them 100% of the time. She enjoyed inflicting pain on him.
For his part, he was not a masochist. Pain did not turn him on, and with the chastity device firmly in place, it hardly would have mattered anyway. However, the fact that he was not a masochist, and yet was still more than willing to suffer for his Mistress made causing him pain that much more enjoyable for Her.
So, She took a long weekend, and booked a cabin at a special resort that catered to the lifestyle. The cabins were equipped with the basic necessities for bondage, sex swings, suspension, and a few other amenities that meant She wouldn't have to pack much. They even had onsite medical personnel that understood the lifestyle and could deal with emergencies should they arise.
Mistress planned for emergencies, but never really anticipated them. By this time She knew his body better than even he did. She knew every reaction. She knew exactly when he reached his breaking point and truly could take no more. She had never hurt him so badly he required medical attention, and She took great care to ensure that would never happen.
So they packed Her favorite gear, food for him, She would be well provided for by the Food Services at the resort, always delivered by cute young submissive boys and girls that were assigned to the cabin. She had requested a girl for this adventure, and since her pet would NOT be serving Her in anyway sexually for this particular weekend, the girl would be used quite extensively.
Arriving promptly at 11 AM for check-in, they headed to the cabin, and pet unloaded everything while She sat and supervised, smoking a cigarette and telling him to "hurry the fuck up, lots of marks to leave on you!" He dutifully rushed and soon had everything inside the cabin, and unpacked just in time for the assigned girl to arrive with a nice lunch for Mistress.
Once the girl, her name was jenny, had informed Mistress that she would simply be staying the cabin with them for the weekend for anything Mistress wanted, had laid out the lunch and Mistress was comfortably seated and enjoying Her meal, jenny led him into the large bathroom facilities and gave him a shower, several enemas, and generally ensured he was prepared for the very long weekend he had ahead of him.
Jenny fussed over him like he was headed off to a dog show, primping him and when finally finished she led him back out to Mistress who had finished eating and was sitting smoking and watching jenny lead him out.
After a cursory inspection, Mistress announced Her satisfaction with his bathing, and instructed the girl. "just hang him over there by his wrists."
He was led over to one of the large beams that crossed the ceiling where heavy chains hung down, and his wrists were secured, and then a pulley system pulled him up to his toes. His body was stretched uncomfortably. Mistress then instructed jenny to gag the boy and attach the alligator clamps She had brought for the occasion.
Jenny did exactly as instructed, sucking each nipple briefly, hardening them before snapping the clamps painfully in place. She waited and did the gag last so as to ensure Mistress got to hear his pained cry as the teeth of the clamps bit into his tender flesh.
His ankles were then spread until just his big toes touched the floor and secured by heavy iron cuffs and chains to the floor. Another chain was then wrapped around the base of his balls and secured tightly making them bulge. The chain was then attached to a three gallon bucket, which Mistress promptly took a long heavy piss letting it fill partway, and smiling up at Her pet's pained expression pretending to mistake it for worry that it wasn't causing him enough pain said softly:
"Fear not, pet, jenny will have to pee soon, and I am sure after some wine later, I will as well. It will be full well before bedtime, and then I will attach the straw and you can begin drinking it through the night to provide yourself with some relief. Of course, you will likely piss as well, which will just continue to add to it."
He groaned around the gag in response and Mistress patted his cheek, then dug her nails in and scratched his cheek somewhat hard, enough to cause tears to spring to his eyes.
"Now, pet, you just hang out. Jenny and I are going to get better acquainted."
She grabbed a handful of jenny's long black hair and led her to the bed. He could not see them from where he was, but he could hear them. He heard jenny undress Mistress, and in his mind pictured his Mistress's body as it appeared. Soon the sounds of kissing, petting, moaning, and the unmistakeable sounds of Mistress's orgasms filled the room around him.
Jenny had gotten up during their sex session and removed the clamps from his numb nipples then rushed back to bed - that had set him screaming for 10 minutes which led to several more orgasms for Mistress.
He could only imagine exactly what was going on, but in his mind, He saw Mistress laying back with Her legs spread wide, both hands gripping jenny's hair tightly and grinding her cute little button nose right into Mistress's clit while jenny's tongue licked as hard and fast as she possibly could. It was a very long two hours for him, listening to the girl pleasure his Mistress while he hung there, aching already.
Soon, he saw jenny rush over to the kitchen, her pert young tits bouncing as she poured Mistress a glass of wine then took it and Her cigarettes back to the bed. He could then smell the smoke, and listened to them chatting softly about what She had planned for him this weekend. He couldn't make out what they were saying, but jenny giggled several times, and Mistress laughed with lustful anticipation as well.
Soon, each of them rose, came over and pissed into the bucket, which after he had pissed once was now just about completely full. Mistress then took a long tube and pushed it down into the piss-filled bucket, then ran it up, and pushed it through the hole in the ball gag until he felt it against his tongue. The ball was big enough that it sealed his lips pretty completely, and he found if he sucked hard enough, he could get piss into his already parched mouth.
He drank greedily, and Mistress laughed, "Do pace yourself, pet, there is after all only 3 gallons in the bucket, and I expect it to still be mostly full come morning. So you need to refill what you drink."
He blinked, that was different, he had thought drinking it was supposed to relieve his aching balls, instead, he was expected to relieve them, then stress them all over again.