The Pledge Mistress Ch. 24

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Pledge Ken struggles with his sexual orientation.
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Part 24 of the 47 part series

Updated 10/29/2022
Created 03/18/2010
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Chapter 24 -- Pledge Ken's illusion

Once he was cleaned up, Ken knelt in the pledge room to await further orders. Bernadette went upstairs to fetch Lisa, figuring that probably she would want to go next. However, given that it already was close to 10:00 p.m. Lisa decided that it was time to put Ken to bed and enjoy a good night's sleep in the guest room. As much as she wanted to enjoy Ken and encourage Kathleen to enjoy him, Lisa figured that a good night's sleep was more important and that her time with Ken could wait until Tuesday night.

Lisa approached Tracy, knelt, and requested permission to release Ken and go to sleep. However, Tracy had other plans:

"You four are going to sleep, but he's not. Have Pledge Ken go to my room, because I'm gonna want to use him before he goes to bed."

"Use him..." Tracy's saying it like he's an appliance, thought Lisa to herself. She felt bad for Ken, but knew better than to argue. She replied "yes, ma'am" and went downstairs to fetch her ex-boyfriend. Lisa escorted Ken to Tracy, and knelt alongside him.

"You are dismissed, Pledge Lisa. Pledge Ken, you will accompany me to my room."

"Yes, Pledge Mistress Tracy."

Ken followed Tracy up to her room, not sure what awaited him. He suspected he was about to suffer the same sadistic treatment that his companion undoubtedly was enduring from Heather, but fortunately what Tracy wanted from him was very straightforward. She ordered him to unfold a massage table and cover it with a sheet. Meanwhile she stripped off her clothes and jumped on top.

"How much do you know about giving massages, Pledge?"

"I...I did some with Pledge Lisa..."

"OK, then you're doing me. Concentrate on the souls of my feet, my calves, my butt, and my neck. I'm gonna want you to give me an orgasm later on, but the first thing I want you to do is relax me."

"Yes, ma'am."

As Ken massaged Tracy, occasionally she gave him instructions to press harder or change the direction of his strokes. He expected her to tell him when she wanted him to move from one part of her body to the next, which she did. He spent over 30 minutes on the backs of her legs alone, and another 20 minutes on her bottom. He was surprised by how thoroughly she wanted her bottom massaged, first by having her muscles pressed hard, and then by having her skin stroked and caressed. Finally he worked his way up her back to her neck and shoulders, spending another 15 minutes on that section of her body.

When Tracy flipped on her back, her attractive body was exposed to Ken in its entirety. She wanted him to massage her thighs, arms, and breasts, but she also was curious to see if touching her would arouse him. She ordered him to pay extra attention to her breasts and lightly touch her nipples until they were erect. Finally she ordered him to explore and massage her vulva. She slowly became wet as she became aroused, but then surprised him by flipping over on her stomach again.

Tracy wanted additional attention to her bottom. At first what she requested was more deep tissue massage, but then she instructed him to begin slapping both sides of her bottom in rapid succession using both hands. Ken started gently at first, but Tracy told him to slowly increase the force of his slaps and keep increasing until she told him to stop.

SLAP-SLAP- SLAP- SLAP- SLAP- SLAP

Ken nervously landed rapid blows as the shade of pink in the Pledge Mistress's bottom turned darker and darker from the ongoing barrage of quick smacks. He continued for what seemed a very long time, slowly increasing the force of the rapid swats. Tracy took a deep breath and held onto the massage table as the barrage continued.

SLAP-SLAP- SLAP- SLAP- SLAP- SLAP

Tracy's bottom became quite red, but she held her position and continued to lie quietly on the table. It was obvious that she was enjoying the sharp stinging from Ken's efforts and wanted the slapping to continue. Her bottom began to swell as her skin took on a deep shade of pink and Ken's hands became tired, but still there was no sign from her that she wanted him to stop.

Tracy never felt the need to submit herself for physical discipline or face reprimand, and under no circumstances would have allowed a partner to strike her in anger or with an implement. However, while she was hazed as a pledge she discovered that she enjoyed the physical sensation of a stinging bottom. What she sought was a nice even burning, spread over her backside as it slowly intensified and approached the line between pleasure and pain. She wanted the stinging prolonged as much as possible at a very specific intensity, which was why she liked her partner to start gently and slowly build up to what she desired. Ken had found that ideal level of stinging, and for a very long time Tracy was content to lie quietly and enjoy what was happening to her.

SLAP-SLAP- SLAP- SLAP- SLAP- SLAP

"Ohhh...Ohhh..."

Tracy's body broke out in perspiration as she arched her backside, exposing it even more to the ongoing barrage of slaps. She reached underneath to massage her clitoris. Finally she was stimulated enough to want...

The Pledge Mistress suddenly rolled off the massage table and got on her elbows and knees, spreading her very red bottom-cheeks and placing herself on lewd display. For the third time that evening, Ken was confronted with the sight of a woman's naked backside, but the emotional turmoil he felt was much greater than what he had felt when satisfying Bernadette and Cherine. He was deeply afraid of the intimidating sorority officer, and he found that fear extremely erotic. What made his situation even more erotic was the contrast between her dominating personality and the sight of her spanked bottom and submissive posture. Fear mixed with sexual arousal as he quickly became hard. He gently touched Tracy's wet vagina to stimulate her even more, then grabbed her thighs and pushed in.

Ken thrust vigorously as confused fantasies swept through his mind. He was excited by the thought of spanking and entering his fierce companion, but also the ongoing physical sensation from his own caning continued to stimulate him as well. His fantasies wandered to Jason, then to Lisa, then to himself, and finally back to Tracy. When he climaxed, his sexual fantasies were right where they started, focused on the person with whom he was making love at the moment.

The normal tension in Tracy's personality subsided somewhat as she climaxed. Her muscles were relaxed from the massage, her bottom stimulated from the slapping, and her sexual drive temporarily satiated by the pledge's vigorous thrusts. She led Ken into the sorority officers' bathroom and into the shower. She instructed him to turn on the water and soap her body, making sure that she was completely clean. She placed her hands against the wall as she spread her legs and ordered him to soap and clean her still-reddish bottom and sweaty vulva. She toweled off and ordered him to clean up and return with her to her room.

Tracy quickly put on a pair of shorts and a Four-Beta T-shirt while Ken knelt. Once she was seated in an armchair, she returned to her role as Ken's superior.

"Pledge, do you understand why you're here? In my room with me?"

"I...to satisfy your physical needs, ma'am?"

"That's part of it, but there's more. First of all we need to get something straight. What we just did, you will keep to yourself. The sorority has an agreement with the Triple-A's that if an officer of the sorority requests a favor from a fraternity underclassman, that underclassman is not allowed to talk about it. If you ever tell anyone about the details of our encounter, you face expulsion from the fraternity. Do you understand that?

"Yes, ma'am."

"OK, now let's move on to you. I'd have to admit that Lisa was right about your sexual performance. You're pretty good. You certainly satisfied me. Once you get going, it's hard to imagine all those hang-ups you're dealing with."

"Uh...thank you, ma'am."

"Now, here's a question for you, Pledge. When you were inside me, what were you thinking about?"

"To be honest, my mind kinda wandered..."

"Wandered in what way?"

"I...you know...like...fantasize about different people...and..."

"Did you fantasize about Pledge Lisa?"

"Yes, ma'am. For a little bit..."

"What about me?"

"Yes, ma'am. I was thinking about you too."

"What about Jason Schmidt?"

"Him too, ma'am."

"What about any other guys besides Jason? I mean, right now?"

Ken paused for a moment. He realized he hadn't fantasized about anyone else.

"No, ma'am. It was just Jason."

"Another question. Do you find yourself fantasizing about Lisa and Jason at the same time?"

"Yes, ma'am."

"Has that ever happened to you before in your life, where you'd fantasize about a guy and a girl at the same time?"

"Uh...it happened to me in high school, ma'am. Same thing, really. I was dating this girl, but there was a guy on my tennis team (I played tennis in high school), who used to wear a jockstrap whenever he played or practiced. He was the only guy on the team who wore one. And every day he'd strip down, change into that jockstrap, and then go weigh himself and get a drink of water at the fountain. And I really wanted to touch, you know, his bare ass. But I never did. I never really got the chance. But I thought about him all the time."

"Was he in a relationship with someone else?"

"Yes, ma'am. He was dating a cheerleader. That's why I never said anything."

"OK, now tell me about Jason Schmidt. What was it about him that you liked so much?"

Ken thought for a moment. Why did he like Jason so much? To start, Jason was very pleasant to look at, with his young face and attractive runner's body, which usually was on display. Ken was used to seeing Jason running around naked, because he only got dressed if he had to leave the male wing of his dorm's floor. Whenever Ken went into Jason's room or ran into him in the bathroom, he was sure to find him completely undressed. He had seen Jason uncovered in public plenty of times as well, modeling for art classes, speaking at nudist promotional events, and above all, during his very public performance winning the previous fall's Tri-Alpha nude 10-K run.

During his first year in college, Ken spent as much of his time as he could with Jason. What fascinated him was Jason's determination to be naked whenever possible. Jason was more than just a nudist; he was something of an exhibitionist and loved being naked around other people. At first Ken simply enjoyed looking at his friend's body, but as time went on, he became very attracted to him. Ken usually took off his clothes in Jason's presence, not because he was a nudist, but because eventually he hoped to seduce him.

The problem for Ken was that Jason was totally oblivious. Jason Schmidt was not the brightest person he had ever known and had a very passive personality. Had they been alone, Ken believed that he would have easily seduced Jason, but unfortunately Cecilia Sanchez got to him first. Cecilia needed a boyfriend she could control, and found that in Jason. Within days of meeting him, she zeroed in on him and completely took over his life. Ken had no hope of fulfilling his hidden desire, because Jason's entire existence revolved around keeping his sharp-tempered girlfriend happy. Apart from that, it seemed that Cecilia rarely let him out of her sight and carefully watched anyone around him.

Ken ended up with Lisa for the same reason that Lisa ended up with Ken, by default. The couple discovered that Ken's sexual drive was released if he was afraid or subjected to physical pain. Lisa knew how to make him afraid, and in doing so got really great orgasms out of him. The orgasms were so satisfying they were addictive, but at the same time Ken's desire for Jason only increased. By the end of the spring semester, he still was making love to Lisa, but fantasizing about making love to Jason.

Tracy interrupted him:

"In other words, what happened between you and Jason Schmidt is a repeat of what happened to you in high school. You see a sexy guy without his clothes, and you want him, but you can't have him. Right?"

A repeat of his experience in high school. Ken hadn't thought about it like that, but he realized the Pledge Mistress was right. His experience with Jason mirrored what had happened two years earlier with his teammate in the school's locker room.

"So, in other words, you've never actually done anything with guys, just fantasized about it?"

"Yes, ma'am. Just fantasy...so far, at any rate."

"Another question. Are you attracted to any of the guys in the fraternity right now?"

"No ma'am. The only guy I really want is Jason. I'm just hoping he'll come back, and maybe..."

Tracy's mouth fell open and she rolled her eyes.

"Hoping he'll come back? What are you talking about? There's no way Jason's coming back! Haven't you been following the news? Don't you know what he's done?"

"Uh...no, ma'am. Pledge Master Arnold hasn't given us any time for stuff like checking the news."

Tracy let out a disgusted sigh and stood up to grab a news magazine sitting on her desk. She handed it to Ken. The cover featured the televised image of a well-dressed middle-aged man with very short hair, under the title:

America's black eye

Ken did not recognize the man in the picture until he read the caption:

Danubian Prime Minister Vladim Dukov

Ken opened the magazine and thumbed to an article featuring a photograph of Jason Schmidt speaking into a microphone. Ken read:

Damning evidence: a corporate son seeks atonement for his father's sins - Surprise prosecution witness sinks Mega-Town's hopes of acquittal - MTA suffers a humiliating defeat as coup conspirators are convicted in Danubian court - "It can't get much worse than this. It's going to completely shut us down over there."

Ken skimmed the article, which answered his question why Jason and Cecilia had left the United States in such a rush in the middle of May.

According to the article, Jason had traveled to Danube City to testify about sensitive information he had snuck out of his father's house in Wisconsin while staying there over Spring Break. The purloined items detailed a coup planned against the Danubian government sponsored by a group of investors and executives from Mega-Town Associates. Apparently it was Jason who first alerted Prime Minister Vladim Dukov about the coup, and it was only because of his information the scheme failed.

The Danubian military moved against the coup plotters on April 21, only 48 hours before the takeover was scheduled to take place. There was no doubt the coup plot was a very serious effort to take over the country, because the Danubians captured hundreds of mercenaries and local collaborators, three CEO's from the corporation itself, piles of stashed weapons, and worst of all, volumes of documentation and military maps. The Danubians were quick to scan all the documents and dump them on the Internet, to ensure the world knew in detail what the U.S. conglomerate wanted to do to their country. The arrests, the capture of all those sensitive documents and their release to the public, and the trials of the conspirators took place so quickly that the company did not have time to effectively counter the disaster.

Jason Schmidt's testimony in the trial was crucial because he was the person who connected the evidence captured in Upper Danubia to the original conspiracy in the U.S. He openly testified that he was the one who first warned the Danubian government and thus was the person who ultimately prevented the coup.

Jason Schmidt might have won the hearts of the Danubians and anyone else who disliked Mega-Town's business practices, but he had just made plenty of very influential enemies on Wall Street. He single-handedly disrupted a plan worth hundreds of millions of dollars, and was responsible for additional financial losses resulting from the scandal's fallout. One financial analyst estimated that Jason's actions might have cost U.S. corporate investors as much as 20 billion dollars.

"I hope that kid realizes what he's done to the American investment community, because he's dead meat. If I were him, I wouldn't be getting much sleep right now."

Tracy took back the magazine.

"I think you'd better forget about Jason Schmidt. You'd better forget you ever knew him. I can guarantee you won't be seeing him anytime soon, so how about moving on?"

For a long time Ken knelt quietly, not sure how to respond. Tracy could tell that he was deeply saddened by the news she had just given him. Finally, impatient at his prolonged silence, she continued:

"Pledge, I got a question for you. I'm wondering if you were ever really in love with Jason Schmidt. I mean the real Jason...the one who testified in Danube City and is dating Cecilia Sanchez. Maybe that wasn't the Jason you fell in love with. Maybe the Jason you fell in love with is nothing more than an illusion, an idealized fantasy that you created for your own psychological needs."

"I...I don't know..."

"That's fine. You don't know. But at least you're willing to admit that's a possibility?"

"I 'spose it could be, ma'am. Maybe I didn't know him as well as I thought..."

"Well, that's something for you to sleep on." Tracy glanced at her clock. "It's 11:15. Almost lights-out."

"Yes, ma'am."

"PLEDGE, STAND-UP!"

With that Ken was released, and his first day at the sorority house came to an end.

----------

While the female pledges slept in the comfortable beds of the guest room, the male pledges and their disgraced Pledge Master slept on the open cots of the Four-Beta pledge room.

The feeling in the room was a combination of fatigue, resignation, and relief. What probably was the worst day out of the week had come and gone. The males knew that what the women could do to them was restricted by the fact the group had to progress with their studies, which meant that they had to have enough rest to be alert in their classes. It was true they would fall behind somewhat in their homework and term papers, but would be expected to catch up once their internment ended and they returned to the fraternity.

With the exception of the pledge under the control of Heather, the young men had a very good chance of avoiding any further physical punishment, apart from the constant "hurry up" smacks they got on their bottoms. All they had to do was obey the whims of their mistresses, which was something they already were conditioned to do at the fraternity. For the most part their duties included constantly giving full body massages, rubdowns with soap in the shower, foot rubs, and oral sex. Some of the women liked having their toes, breasts, or bottoms kissed and licked, but the rule was that if a sorority member wanted attention to any part of her body; her body had to be thoroughly washed before she approached the pledge. Mostly what the women wanted was to have the males comfort them and attend to their various physical needs.

A few of the Four-Betas also wanted to use the male pledges for regular sex. The women who wanted intercourse were the ones with hidden sexual needs like Tracy, were between relationships, or simply wanted a casual orgasm to relax. The pledges soon learned that the women who wanted normal sex were in the minority, given that most of them were in relationships either with members of the fraternity or other members in the sorority. Thus the pledges were able to accommodate their mistresses, because obviously a single male would not have been capable of having a dozen orgasms every night for six days. Typically the Triple A's needed to service two or three women over a 24-hour period, something all of them were capable of doing.

Although he was under only five women, Ken expected to be kept very busy. Bernadette planned to have sex with him at least once each day and also have him massage and perform oral sex on Cherine. Lisa would want sex from him as well, and try to get Kathleen to experiment with him. That meant at least two orgasms per night, and possibly three.

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