Holiday Loving Ch. 03

"Do you confess to unauthorized sexual union with slave Erioca?" asked Mistress Angelique.

"Yes, Mistress."

"And do you accept the sentence of 25 strokes of the flogger on your cock and balls?"

"Yes, Mistress."

"Then let the punishment commence."

Mistress Tracy swung the flogger down hard onto the top of Richard's cock. As it was partly hard, much of the force of the blow was softened by it simply bending. Still it was undoubtedly painful and Richard let out a grunt and closed his eyes at the pain. The second stroke was upwards, striking his balls cleanly as the straps wrapped under them and impacted against the underside of his cock. Richard screamed, his body shaking in pain. The next few strokes were very similar and by the end of those his balls and cock were bright red and his body was shaking uncontrollably. Tracy changed the angle again and began striking from above his now soft cock, aiming to wrap the straps around so the ends struck his balls. She succeeded, and Richard gave a howl of pain with each of the following strokes. By now his cock was weeping blood from several places on the upper and lower surfaces and his balls were bright red and swollen. Four strokes to go. For those Tracy went in sideways, striking the sides of both his cock and dangling balls, obviously causing intense pain.

Once the punishment was completed, Richard was paraded through the group and I was able to feel his cock and balls, amazed at how hot and swollen they really were. I hoped for his sake that they would still be usable, but also for Tracy's sake as I had a sneaking suspicion that she received many benefits from him still being able to have sex.

"Can I do that to you?" I whispered to Jeff.

"Not like that. I may let you do something sometime but only if I can do something to you as well," he whispered back.

"That concludes the punishments for this week. I'm sorry there is not more; everyone seems to be far too well-behaved. We now go onto the sharing and caring part of the evening. It's guy's choice first off tonight so that means that every guy gets to select a girl's disk and had 45 minutes with that girl to do pretty much as he wants. In this case the penalty for the use of the safeword, which tonight is albatross, is ten strokes of the cane if it is considered that the use was unjustified. So, ladies, you'd better be careful if you choose to use it. Gentlemen, please choose your partners."

"My number is 73," said Jeff, "So whoever chooses that number has you for the next hour. That time is divided in three parts, the first part where one person can punish the other, the second where the roles ae reversed and the third where usually they make love together. Good luck, darling; enjoy."

The men all took pink disks and soon I heard someone calling "73". I approached the sound to find he was an attractive guy, probably mid-30s, and I though very sexy. Obviously I was eager for sex as I was dripping after watching a guy's cock and balls being beaten, so I looked forward to my time with this guy.

"Hi, I'm Cecil," he said.

"I'm Mandy," I replied, moving closer to him and putting my arm around him. "What're you going to do with me, honey?"

"Well, I'm going to fuck your sweet ass, but as for what else, we'll just have to see."

Cecil escorted me towards a series of small rooms which had curtain walls between them but the fronts were open. Inside each was a bed, fastenings against the rear wall and a selection of restraint devices, a cane and several whips hanging from hooks. I looked at them, partly with curiosity, partly with fear, knowing that they could be used to cause me pain, and feeling very ambivalent about that prospect. I knew that pain and pleasure were closely linked, and I also knew that people could cum while experiencing sexual pain, but I did not know or yet trust Cecil.

"So what happens now?" I asked.

"Well, I think that as you're the newbie here, I should go first and use some of this on you. That way when the bell sounds, you'll have some idea how far to go with me. Sound fair to you?"

I didn't reply for several seconds, looking at his hanging ball sac and wondering what I should do to it when my turn came. "Y-yes, that sounds fair," I replied at last.

In a few minutes I was restrained over the edge of the bed, my ankles fastened to rings on the floor, legs wide apart, arms stretched and fastened to the far wall. Cecil had a cane in his hand and was swinging it in the air. I listened with apprehension to the whistling sound it made, imagining it landing on my poor exposed ass.

"You ready, Honey?" he asked.

"Guess so."

I heard the swish and then felt a burning, stinging pain across both ass cheeks. My stomach reacted immediately, feeling like it was turning over inside at the same time as the pain lanced through my body. I heard myself scream; short, loud and sharp. Then Cecil was alongside me.

"How was that?" he asked, his hand rubbing my ass.

"That was painful. I've never felt pain like that before. It was indescribable. However, I love what you're doing now. I don't know why but I want another stroke please."

His hand ceased its movement and he resumed his place, then a second stroke landed on my ass. I was ready this time, knew what to expect, so I made no sound, feeling the pain surge through my body then seemingly rebound to my pussy. Amazingly I felt sexy from being caned. I didn't say anything, nor did he; he simply struck me again. This continued until I had received ten strokes, when he stopped.

"How's that feel?" he asked.

"Well, my ass is burning and still stinging, but I feel soooo sexy. Why does that happen?"

"The pain and sexual pleasure nerves are closely linked and some people find it difficult to distinguish between the two sensations. Maybe you're one of those lucky people. I won't give you any more. Instead I'll reposition you and use one of my favorite devices on you." He grinned as he said that.

I was quickly untied and turned over, my legs again fastened wide apart and arms attached to the wall as I lay on my back on the bed. He could easily have entered my pussy in this position but he didn't. Instead he took a short whip with many tails and showed it to me before trailing it across my breasts and pussy.

"I think you'll like this," he said.

I remained silent, watching him warily, seeing his arm go back and then watching the whip swing and land across my left breast. I bit my lower lip as the stinging pain radiated from my breast across my chest then slowly dissipated, until it was repeated on my right breast. He alternated between breasts, seeming to make certain that each stroke landed across my nipple, until I had received ten strokes on each breast.

"How does that feel?" he asked.

"Sore and hot, and very sexy. Can you please just fuck me now; I so need to cum."

"Patience, my darling, that will come soon enough. One more set of ten should do the trick."

He moved and again raised his arm with the whip, this time bringing it down across my pussy. I felt the strands land across and between my labia, one in particular striking my clit and sending a stinging pain through my body. I had barely recovered from that stroke when a second landed, then a third. I felt my sexual responses growing; each stroke pushed me a little closer towards my orgasm despite, or maybe because of the pain. Six, seven, ooohhhh it was soooo nice, I wanted it to go on forever, eight, nine, sooo close, ten, and I couldn't quite get there. He stopped and stood over me. I noticed his cock was rock hard; he obviously enjoyed causing pain to sexy defenceless women.

"More, please," I whimpered, "I was sooo close to cumming."

"No more of that. In the last few minutes we'll do something else that you may find just as nice."

Nice? Was this really nice? I guess the effects were, but the cause maybe not so much. I watched as he took a small, short tubular wire cage device which had a rubber strap across one open end. He placed the other end over my breast and pressed down so that the pressure squeezed my breasts into the tube, causing my nipple to elongate and harden. My nipple was pushing the rubber strap at the top end up slightly. Then I watched in increasing horror as he held the center of the rubber strap between thumb and finger and pulled it away from my breast while holding the base of the cage firmly against my chest. It was very obvious what would happen if he let go the rubber. He grinned at me, seeing my fear, then moved his hand closer to my chest before releasing the strap.

The pain in my nipple and breast was horrendous and rocketed through my body, pulsing to my brain, demanding to be processed, pouring to my pussy, heightening my need for release. As this was happening I heard a scream and then realized it was me. I bit my lower lip to stop it.

"How was that?"

I didn't know. When it happened it was extremely painful but that quickly subsided and I was left with a craving for more of the same. What was happening to me? What was I becoming?

"It was painful, but Ok, then highly sexy," I managed after quite a few seconds.

He removed the cage and placed it over my other breast then repeated the procedure. Again the pain, the sexual arousal but no scream this time. I noticed the clock on the wall indicated there was only one minute left for this third so I thought my torment was over; wrong. He removed the cage, flipped t over so the rubber was downwards, then placed it over my clit with the rubber aligned with my oozing trench.

"Ready for the finale?" he asked, again with that infectious grin.

"I grinned back bravely. "Do it," I replied.

He pulled the strap back, our eyes met and he let it go. Pain radiated from my pussy, down my inner thighs, into my abdomen, throughout my body. I heard myself scream again then I felt myself cum, hard, my body shaking in its restraints as a massive orgasm washed through me, leaving me limp but still horny.

"Wow, honey, that was sooo painful and so intense," I told him as he released my bonds.

"Pleased you liked it. Maybe we could do it again some time," he chuckled as he helped me stand. "Not it's your turn. Do your worst, or maybe your best, however you want."

What to do with this guy who had caused me so much painful pleasure? I wanted to beat his balls, hurt them. Right then, had there been a knife available, I felt I would have been quite capable of castrating him, but fortunately there was not, and anyway, I reasoned, if I cut them off then I couldn't torture them. I led him to the wall and restrained him against it, facing outwards. I then caressed his cock and balls, wanting him inside me but knowing that would come later. I looked at what was available and took the same multi-tailed whip he'd used on me and swung it to get the feel of its weight and balance. I then looked him in his eyes and brought the whip upwards between his legs, hard.

Cecil let out a howl of agony as his body went rigid from the pain of the strands impacting against his balls. I stood and watched as he slowly seemed to process the pain and his balls began to retract upwards, probably intent on avoiding a repeat stroke. Once he had regained some air of calmness, I repeated the stroke, his reaction being slightly less extreme. I continued beating his balls until he'd received ten strokes, by which time he seemed quite exhausted from the pain. I knelt in front of him, caressing his red ball sac and moving his treasures inside.

"So how do you feel, honey?" I asked.

"Like I've been kicked in the balls. The pain of each stroke radiated through my stomach something terribly. I've had this before but each time it seems to be worse, or maybe my memory of it fades. What next, darling?"

I looked at what could be next and decided if he'd caned my ass, I'd cane his. How to restrain him? I saw a device that looked like it could fit around his balls with bars across the backs of his thighs. I'd seen a photo of it somewhere once before and seemed to remember it was called a humbler. I took it down and fitted his balls through the ring, tightening it so they couldn't escape but not so tight that they'd lose their blood supply. Then I released him from the wall fastenings and told him to bend over and touch his toes. He did and I moved the bar between his legs and twisted it until it was across the back of his thighs. It was fairly obvious that he couldn't straighten up without stretching his balls a huge amount, which would not have been in his best interests.

I took the cane from the shelf and swished it as he had done then positioned myself so that I could swing it against his ass. How hard, I wondered. Very, came the reply; after all, he was the experienced one here and he certainly hadn't let me off lightly, I thought.

"Ready?" I asked.

"As much as I can be."

I applied the first stroke, revelling in my power to strike him hard, to cause him pain and to create ridges across the pristine skin of his ass. although on closer inspection I noticed it wasn't so pristine and clearly showed the signs of having received this treatment before. So I wasn't the first, I thought, so that means I should be able to hit him harder. I did, nine more hard strokes, each leaving a red line across both cheeks, each causing him to give a jerk as his body tried to straighten, each pulling his balls painfully. What a great device this humbler was, I thought. I glanced at the clock; five more minutes. What could I do in five minutes?

I knelt down and twisted the humbler so the bar fitted between his legs, then he stood up and I looked at the bar hanging from his ball sac, stretching it down slightly. On the shelf were some weights, so I told him to stand still and collected twenty pounds of metal weights, placing them between his legs. I then made him crouch down and tied two five pound weights to the bar.

"Stand up," I ordered.

He stood and I watched as his face contorted as the weights lifted off the ground, stretching his balls downwards. I had him hold the weights for 15 seconds, then ordered him to crouch, which he did with a look of relief.

"How was that?" I asked.

"Painful," was all he replied.

"Well, Cecil, we ain't done yet."

I noticed there were only two minutes left on the clock so I quickly tied the other two five pound weights to the bar and ordered him to stand. Very slowly he lifted the weights off the floor, his scrotum stretching at least four inches downwards as his balls were partly deformed by the tie around them holding them to the bar. I watched as the second hand slowly swept around to the top of the clock again and as the bell rang I told him to lower the weights, which he did quickly and with great signs of relief. I untied everything and once he was free, we embraced.

"Thank you, darling," he said, "That was quite a workout. Shall we see if everything still works as it should?"

I could feel his hard cock pressing into my stomach, the feeling making mme want him inside me urgently.

"Yes, honey, fuck me; fuck me hard, fuck me well and fuck me now."

He lifted me off the floor and as I wrapped my legs around him he entered me, lowering himself until he was fully inside me before carrying me to the bed and placing me on my back with my ass at the edge of the bed. He then proceeded to fuck me hard, as requested, his cock sliding in and out, stimulating the sensitive walls of my vagina while his balls slapped against my perineum with each stroke. It took only a few minutes before we were both ready to cum, and cum we did, Cecil intensifying the experience by slapping my recently caned ass with his hand, sending waves of painful pleasure through me as my orgasm washed over me. I felt Cecil spurt his cum against the ned of my vagina which caused even more surges of pleasure to pass through me. Cecil then collapsed onto me and we lay together breathing hard, listening to the sounds of lovemaking from other couples in the small rooms around us. Fleetingly I wondered how Jeff was getting on, hoping he still had some left for me tonight.

After a short rest Cecil dismounted and lay on his back on the bed. I used my mouth and hands to stimulate his cock, taking care with his sore bruised balls, and once he was hard again I straddled him and lowered my body to engulf his cock. I rode him slowly at first, gradually increasing my movements until we both approached another release, cumming together less than a minute before time was called. We kissed each other gently and lovingly, thanking each other for the pleasure, pain and joy we had received, then walked back into the main room, where chairs had been assembled around a central stage area. Everyone replaced their disks in the bowls and Cecil and I parted, each seeking our partner.

Jeff and I had only a very short time to reacquaint ourselves before Mistress Angelique returned to the stage.

"Well, I hope you all enjoyed yourselves for the past hour. I was wandering around and it seemed like you were all having fun. Now we come to the demo part of the evening when two particular pieces of equipment will be demonstrated by two randomly chosen people, a man and a woman. Tonight the man will be fitted to the milking machine and will be milked until dry. This can be very painful, well, let's clarify this, this is always very painful. As the saying goes, you can't get blood out of a stone; well, in this case, we try to get cum from a man for a while after he is totally emptied. He will continue to have muscular contractions and continue to cum in the machine despite there being nothing to expel. However, you'll see this for yourself tonight and one lucky man will experience it. For the lucky woman, we have a wooden horse for you to ride. I know that some of you have ridden one before and if you have you will know how painful it can be. We do have three different settings of the bar, a flat bar mainly used for me to allow their body weight to crush their balls, a rounded edge for those who are inexperienced with pain, and a sharp edge for more advanced riders. So, I'll let the slaves bring the equipment onto the stage and you can see what 's been prepared for your entertainment tonight."

The slaves brought the milking machine and wooden horse onto the stage, plugged in the milking machine, then left the room.

"Now, as you know we always ask if there are any volunteers who would like to demonstrate this equipment. Is anyone wishing to volunteer?"

Mistress Angelique looked around the room and after a short time continued.

"So, as there are no volunteers, does anyone wish to volunteer their partner for this torment?"

Jeff looked at me and I gave him a quick whisper of "Don't you dare if you want sex later." He grinned at me and whispered back that he wouldn't as I was a newbie. Nobody volunteered their partner, probably afraid of repercussions later in the bedroom, so Mistress Angelique continued with the selection of the two victims. Two slaves brought the bowls of numbers to her and placed the bowls on the table. She then put a hand into each bowl, swirled the disks around, then drew out one with each hand. I felt my grip on Jeff's hand increase as the tension mounted.

"As you are all aware, by coming to this evening you have agreed to take part in a public demonstration if called upon to do so. Therefore, the draws from the bowls are binding. For the men, the number is 26. Who is number 26 please?"

A man stood nearby and hesitantly walked to the stage.

"And for the women," I felt my grip intensify on Jeff's hand even more, "The number is 52."

I sighed with relief as a woman behind us gave a shriek but stood up nonetheless and made her way forward. The two selected victims mounted the stage. I noticed the woman had ringed nipples and had obviously been whipped tonight judging by the red stripes across her back and ass. I noticed my ass was still a little sore after my caning. The man had large balls hanging down low in the warm room and his cock was semi-hard.