The Pledge Mistress Ch. 23

"Pledge, would you like to take him from the front or from the back?"

"You mean...like, put my finger up his bottom, ma'am?"

"Yeah."

"Yeah...I...I'd like that...I mean to try that...ma'am."

"You know what to do, Pledge?"

"I think so, ma'am."

"OK, you get the honor."

Kathleen lubricated her finger while her companion grabbed Ken's penis and pushed him backwards. Ken did not resist, because what was about to happen to him was not anything he had not experienced before. He enjoyed having his bottom penetrated and the strange feeling having his sphincter stretched always gave him. He stuck his bottom out, trying to make it easy for Kathleen to enter him with her finger.

Kathleen was fascinated by what she was doing, to the point that she forgot that she was in a room full of witnesses and she was being photographed and videotaped. She explored Ken's waiting bottom-hole as she applied the lubricating gel, and then pushed in and moved her finger back and forth. She was curious to see what a man's insides felt like and how far in she could push her finger. As she moved her finger around and Ken felt the familiar pressure against his sphincter, a wave of arousal swept over him. With her free hand Kathleen explored his bottom, fascinated by the smooth skin and the knowledge that before long it would be marked by 21 cruel welts.

Ken perspired and groaned as the two women worked him into an erotic frenzy. They sensuously massaged him inside and out as discharge after discharge came out of him into the jar. Ken had surrendered himself entirely and loved what was happening to him. Kathleen was totally aroused at the thought of so intimately exploring the bottom of another person and the warm, soft feel of the young man's intestine on her gloved finger.

As she continued to feel around inside her male counterpart, Kathleen wondered what it would be like to be taken from behind. She certainly knew what it felt like to be fucked in various positions in her vagina, but most of those experiences had been associated with very unpleasant memories. She had given oral sex to her high school lovers on many occasions, but sucking a man's penis did not satisfy her in the least. Until that moment, with her finger shoved up Ken's bottom, it had not occurred to her that she might enjoy anal sex...with a guy.

The thought of being penetrated up her bottom both frightened and fascinated Kathleen. She had been thoroughly aroused whenever Lisa kissed and licked her bottom-hole, but obviously her lover was not capable of actually penetrating her. As she held up the jar and posed with the junior and their exhausted captive, Kathleen mulled over the idea of submitting to being fucked up the ass, just to see what it would feel like. She felt guilty because the love of her life was Lisa...however...wasn't she, as a member of the Four-Betas, expected to explore her sexuality? What would Lisa say about her secret desires?

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Cherine was the next of the female pledges called up to assist in masturbating one of the males. The third guy was fully erect as soon as he was restrained and needed very little encouragement to fill his jar. The junior gave Cherine the honor of stimulating their subject's penis and rubbing his bottom while she worked on massaging his chest. Lisa could tell that Cherine was totally absorbed by her task and fascinated as her hands worked their magic on the restrained young man. She explored his shaven pubic area and carefully watched his penis as it pulsated and shot semen into the waiting receptacle.

Lisa got Heather's favorite pledge, the "fat guy". One detail Lisa found interesting was how much weight he had lost in just two weeks: she estimated that he might have dropped as much as 15 pounds so far. Not surprisingly, his entire body was covered with welts, both old and new, inflicted by the constant barrage of swats from Heather's riding crop. Lisa noticed that his bottom had no new marks on it, because undoubtedly his tormentor wanted to save it for a nice thorough caning.

The junior in charge of Lisa and the pledge knew that Lisa had plenty of experience with arousing men and simply left her to stimulate the guy on her own. Lisa worked him from both the front and the back, with synchronized movements on both his prostate and his penis. Her goal was to see how quickly she could make him come, but his body turned out to be somewhat stubborn. It took her more than two minutes to find the right combination of stimulation to force him to climax and fill his jar. However, once he started, Lisa's subject continued squirting, surprising her with the duration and volume of his discharge. He moaned and his knees trembled from the physical relief and utter humiliation he was enduring at the expense of the two women assaulting his body. Finally he was totally spent and hung limply on his chains, while Lisa held up his jar for the benefit of the cameras and audience.

Two juniors dispatched the final pledge, expertly arousing his body and forcing him to empty into his jar within just a couple of minutes. In some ways what happened to the final member of the pledge group was more humiliating than what had happened to his predecessors, because the women showed absolutely no emotion as they extracted the semen from his body. They knew where to put their hands, which nerves to touch, and worked him with about as much emotion as a vet groomer might display while shampooing a dog. And yet, they completely cleaned him out, leaving him more spent and exhausted than any of his companions.

Once five jars of semen were sitting on display, Heather announced the next phase of the ongoing punishment, the public caning of the five pledges and their Pledge Master. She decided to flog Arnold first, because, as she put it: "He deserves my undivided attention."

Arnold approached the table, but protested that he could hold his position and did not need to be tied down. Heather ignored him, and coldly strapped him to the table while calling him a "pathetic fucking failure." Lisa realized something very interesting; that Heather was not just teasing. She was genuinely furious with him.

Lisa pondered: why should the Sergeant-at-Arms be so angry that the Tri-Alphas lost the scavenger hunt? That didn't make any sense, unless...unless...Heather actually wanted Tracy's pledges to lose. Of course, had that happened and the sorority members been forced to attend the "Skins and Shirts" ball in the nude, Tracy would have taken most of the blame. Another thought suddenly occurred to Lisa. Maybe the reason the penalty for the losers of the scavenger hunt were so brutal was because Heather had expected the Four-Betas to lose. Perhaps she actually wanted the pledges to suffer and for them to blame the Pledge Mistress, just like she wanted the other sorority members to blame her for having to attend the dance in the nude. Maybe her goal had been to turn everyone, both the pledges and the sorority members against Tracy. Certainly losing the competition would have been a good way to do that, to undermine Tracy's relationships with the other women of the sorority.

If Tracy was aware that Heather hoped to undermine her: that would explain her strange and secretive behavior over the weekend. It would account for her desire to sneak the pledges out of the sorority house so they could rest. It also would explain the strange argument she had over the phone with President Alexandra. Lisa remembered her mentor's words:

"...look, I don't give a shit about Heather, I really don't! Those pledges are my responsibility, not hers! Alexandra, you know what? If her feelings are hurt, tough shit...now, either you want my group to win, or you don't! Which is it?"

Lisa shuttered at the implications of such a dispute. To undermine Tracy's standing among the other women, apparently Heather was perfectly willing to jeopardize the well being of the pledges. That was a very scary thought, given the number of pledge challenges that still lay ahead.

While Lisa was mulling over the relationship between Tracy and Heather, the Four-Beta Sergeant-at-Arms was flexing her cane and menacingly tapping the Tri-Alpha officer's exposed bottom. Lisa studied Heather's face, which continued to reflect genuine anger. She's pissed, thought Lisa to herself. She's actually pissed at that poor guy.

Heather positioned herself, drew back, and laid a fearsome stroke across the base of both sides of Arnold's bottom. He closed his eyes and held his breath, surprised by the force of the blow. He had thought that surely, because Heather was punishing a fellow officer, she would go easy on him. He had thought the punishment was more to humiliate him than actually hurt him. He was very mistaken, not yet realizing he was dealing with a woman who was totally infuriated that his group had lost.

Heather stood back to admire the rising red welt, and relished the satisfaction of knowing that she still had 24 to go. She already knew how she would proceed: she would start with five lines across the lower part of both bottom-cheeks, then hit hard with 7 strokes concentrated on each side, and then finish with strokes laid across his upper bottom and upper thighs. She would strike him as hard as she could without drawing blood, enjoying the opportunity to vent her anger and satisfy her own sadistic desires.

A sinister swoosh and the splat of rattan making contact with unprotected skin signaled the second stroke against the suffering Pledge Master. Again he gasped and suppressed a scream, not just from the pain, but also from the shock that Heather planned to inflict a very serious punishment. Heather twisted back and savagely delivered a third blow, widening the strip of pure pain across the lower part of Arnold's backside.

Arnold was not the only one surprised by the severity of Heather's treatment. It turned out that the other Tri-Alpha officers were equally surprised; that they had expected Arnold's punishment to be more about humiliation than real pain. Even Alexandra, who normally was very supportive of her Sergeant-at-Arms, looked on with a nervous expression.

Arnold was breathing quite loudly and sweat was running down his body even before the first five strokes were completed. Heather paused to run her fingers along the cruel welts as they continued to rise and darken. This is really great, she thought to herself. Now he's gonna get it, full force, on each side of his incompetent little ass.

Heather began on Arnold's right side, carefully positioning herself so the end of the cane would land squarely in the middle of his right bottom-cheek. She struck very hard; leaving savage red lines that turned dark very quickly. By the 10th stroke Arnold was moaning after the cane landed, and it was clear that he was not going to make it through the entire punishment without crying.

Because it wasn't the first time he had brought problems to the pledge program, Arnold's fellow officers had thought that "quality time" with Heather might make him wake up and understand that he was not performing to the fraternity's expectations. The only problem with the decision was that the punishment she was inflicting on him was a bit much. As they watched the punishment with mounting concern the Tri-Alpha officers glanced at each other, fully regretting their decision to allow the Four-Beta Sergeant-at-Arms to punish their Pledge Master. However, they did not intervene because they felt restrained by several Tri-Alpha traditions and unspoken rules.

The first rule was that, once a decision was made, everyone involved was sworn to uphold it. Decisions had to be carefully considered and made for good reasons, but once a decision was announced there could not be a bunch of doubt and second-guessing.

The second rule stipulated that the fraternity and sorority officers never questioned or challenged each other in public. All disputes among the leadership had to be kept secret so the ordinary members would see the their leaders as an infallible group who always supported each other. No matter what the other officers thought about Heather's flogging, there was no way they were going to challenge her in such a public setting. She knew that, and because of it felt free to flog Arnold to her heart's content.

The final rule, and the most important one, was that failure always had consequences, especially in cases where failure could have been avoided. Had the contest been relatively close, Arnold's leadership skills would not have been questioned, but his group's pathetic performance indicated that he had done nothing to prepare his pledges. The problem facing him was that scavenger hunt debacle was not the first time his pledges had gotten in trouble. They had done well with house cleaning and the physical fitness portion of their training, but academics were another issue. Already there had been complaints from a professor about two late assignments, because Arnold had not set aside enough time for the pledges to study. There also had been problems with the Tri-Alpha Life Skills Training and concerns over how much of that material they really were memorizing.

Heather paused after her 12th stroke to let everyone contemplate what she had done so far. Arnold's bottom had five dark lines laid very close to each other on both sides at the base of his backside, and an additional seven strokes concentrated on his right side. The most recent strokes had been more severe because their force had been concentrated. Arnold's bottom looked rather strange at that moment, because the upper part of his left bottom cheek still had no marks on it and contrasted with the painful weals on the right side and the lower part. His suffering was made quite clear by his desperate breathing and trembling. His entire body was covered in sweat, including his bottom. Good, thought Heather to herself, now my target is nice and wet.

Heather flexed her cane and moved to her victim's left side. She made several false starts before landing a cruel blow just above the five strokes from the beginning of the punishment. When she landed her second stroke from that portion, Arnold groaned loudly and his body started shaking from suppressed sobs. The disciplinarian didn't bother to try taunting him; she simply continued striking him at a very leisurely pace. By the time she got to the seventh stroke, Arnold was crying quite nicely.

There was a break in the punishment while Heather paused to see if she wanted to use a different cane for the final six strokes. She picked up three canes of varying lengths and thickness and slashed them through the air in front of her teary victim. Finally she selected the thinnest cane of the group, one guaranteed to deliver a very sharp sting. Satisfied with her performance, she resumed her position and delivered a vicious stroke to the unmarked skin of both sides of the very upper part of the Pledge Master's bottom. She followed that stroke with a cruel stroke across his upper thighs. The final four strokes were administered in the same way: above-below...above-below.

Heather left Arnold to sob for a few minutes before untying him and allowing him to stagger to his feet. She ordered him to turn around so her female audience could study and photograph the welts. Then she ordered Arnold to turn his face to the camera so that both his welts and his face appeared in the pictures. All five of his pledges also would have to pose for pictures as part of the over-all punishment.

Arnold did have one break coming to him that night; he would be spared the public enema. Enemas and forced ejaculation, which were considered much more humiliating than corporal punishment, were reserved only for pledges. Heather ordered Arnold to stand against the far wall of the sitting room, to keep his punished backside on display for the benefit of the women and Tri-Alpha officers.

Lisa glanced at the other male pledges. They were terrified, quite obviously. She was not surprised to see that Ken had a furious erection. What surprised her much more was to see an erection on the "fat guy" as well. Heather also noted the erections, and ordered the two pledges to stand up and face their audience. She put her arms around their shoulders and posed for several pictures, cruelly smiling as the men's two penises pointed directly at the cameras. When the flashing died down, she grabbed both penises and firmly held them for a second round of photos. Finally she ordered the two pledges to put their hands behind their heads and run in circles around the room. The women cheered and guffawed as the two mortified young men ran their laps while their penises bounced around as they moved.

Lisa was not surprised when Heather ordered her favorite victim to extend himself over the table next. Nor was she surprised to see the Sergeant-at-Arms punish him with as much determination and cruelty as she had punished Arnold. She used the same pattern on him: five stroke across both sides of the base of his bottom, then six strokes concentrated on each side, and finally four strokes with the thin cane on the backs of his upper thighs. The "fat guy" did surprise his spectators by not crying. Heather had beaten him so much over that last couple of weeks that he was becoming used to it.

Heather ordered her victim off the table and to display his welts for the benefit of the audience. Like his Pledge Master, he had to pose for numerous pictures. Heather then ordered him to get on his elbows and knees on a thick towel laid out on the floor, his welt-covered bottom spread and turned towards the audience. A Four-Beta junior brought a full enema bottle and hose assembly. The nozzle already had been lubricated and was ready to insert. Heather casually took it and shoved it in, repositioning it gently to make it go deeper. As the women applauded and the cameras flashed, Heather paused to let the utter humiliation of the pledge's experience sink in. Finally she opened the clip and the water rushed into his intestines. The pledge already knew that he would be required to hold his position, on his elbows and knees with his bottom spread and pointed upwards, until the next caning was completed.

As the first pledge struggled through the throbbing pain in his backside, the increasing pressure in his stomach, and holding an uncomfortable and embarrassing position on the floor, Heather got started with the third victim of the evening. She punished using the same pattern, but Lisa noticed her striking considerably less vigorously and finishing much more quickly. Heather already had flogged the two males she was most interested in flogging and had worn herself out. Given that she still had three pledges to go, she had to be careful to pace herself and not get tired out too quickly. The third pledge made it through his punishment without sobbing, although sweat and tears were running down his face when he knelt on the towel to receive his enema.

Two Four-Beta juniors handcuffed the "fat guy" and took him downstairs to relieve himself. Then he would be shaved and, if necessary, have his bottom waxed for a second time. Finally he would be brought back upstairs, issued a Four-Beta T-shirt, and formally begin his six days of punishment duty.

Even had they not been facing punishment, at some point that week the Tri-Alpha pledges would have had to submit to being shaved by the Four-Betas. Pledging males were not allowed to have pubic hair until they completed their initiation, so about once a week they had to be shaved. Pledges also had to keep their bottoms completely free of hair, so they had to be waxed whenever there was any sign of hair growing back. Upon being sworn in as full members the pledges would be allowed to re-grow their public hair if they wanted, although many of the members of the fraternity preferred to remain clean-shaven. As for waxing the hair off their bottoms, the Tri-Alphas had made that a custom for the entire group over the past several years. At first only the gay members waxed their bottoms, but over time the straight members started waxing as well. Having their bottoms stripped of hair eventually became a trademark of the fraternity, and it turned out that most of the Four-Beta women preferred the new style on their partners.