College Caper

By Scott Westwood

Published on Aug 10, 2002

Gay

WARNING: This story contains sexual acts between college age men. If this is not to your tastes, and/or is illegal in your area please do not read any further.

The story is copyrighted. Please do not distribute it to any newsgroups and/or web-sites without permission from the author. You may, however, send it to your friends in any form you wish, as long as no changes are made to this file.

Parts of this story were inspired by my own experiences with fraternities. However, THIS story is mostly fiction. Any resemblance to any individual, alive or dead, may be accidental.

Constructive comments and suggestions are appreciated. Flames will be cheerfully (and totally) ignored.

College Caper (MM, bd, sm, anal, whipping, cbt, initiation) Chapter 1

NOTE: Chapter one is the setup for the entire scenario. Chapter two will begin the full sexual encounters.

Saturday/Sunday It was another Saturday night at the Phi Sig house and as usual the brothers were partying. I live across the street from their fraternity house and am a regular guest at their parties. Though I graduated from college many years ago (I'm now 40), I still hang in there with the fraternity crowd. In fact I did so much "hanging in there" that they made me an honorary brother, due partly to the fact that I am a generous person and contribute to their party fund on a regular basis and frequently hire some of the brothers to work part-time at one of my restaurants.

What made this particular fraternity all the more appealing was it's reputation for accepting only the best. Virtually every member of the university lacrosse team was in the fraternity, along with an assortment of jocks from other sports and the "Who's Who" of campus leaders.

It was also well known that the fraternity had one of the most rigorous pledge periods. In spite of crackdowns on college hazing, they continued with their time honored method of testing new pledges.

This was a more formal party than most. The six members of the pledge class were wearing tuxedos and were acting as waiters and bartenders. So it was easy to check them out. There was also a board next to the bar with each of their pictures. This pledge class, though smaller than usual, was the best looking bunch ever.

What follows are brief descriptions of the pledges, including some information I learned from the brothers that night and later on:

Todd 19 years old, dark hair, glasses that made him look intellectual. Slender body with a narrow waist and a little hair on his chest and a very thick bush. He was also a real party animal who believed in living life to the fullest. He wanted to try everything at least once.

Jim 18 years old, Sandy brown hair, with dark hair on his chest. A well proportioned build but not overly muscular. He liked to swim to keep fit when not playing lacrosse. Jim was also the intellectual type. When he wore his glasses he looked like a braniac geek.

Brad 18 years old, light brown hair, 5'8" with a heavy bush, but a minimal amount of hair on the rest of his body. Without question one of the most handsome guys on the planet. He took pride in his body and worked out constantly. He looked like the famous Greek statue, "David".

Jared 18 years old. Blond haired blue eyed with a well proportioned body. He looked like a 16 year old, with rosy cheeks that would remain with him for many years to come. His smooth body did not display much in the muscle department, but he was actually very athletic.

Brian 23 years old. Short blond hair, green eyes with a slight, but well developed body. Older than most freshman due to the fact that he served four years in the Marine Corps prior to entering college.

Steve 19 years old. Light brown hair and warm brown eyes. He was built to play rough and tumble sports. His body was well defined and solid with a 32 inch waist. His abs were the envy of every guy on every team he played on. Besides lacrosse, he loved to play rugby, the British sport recently added to the college sports program because he enjoyed the hard-hitting physical contact.

They were a great group of hot studs and ones that I began fantasizing about throughout the party. I was sipping a beer and was in the midst of an incredibly perverse fantasy when an extraordinary thing happened, Jake, the fraternity pledge master came over to me and asked to speak with me in the next room. That in itself was not extraordinary. It was what he told when we arrived in the other room that was so unusual.

"Scott, I was wondering if you could do the fraternity a big favor," Jake whispered in a mysterious way.

"Sure Jake, how can I help?" I whispered back, almost laughing at our conspiracy demeanor.

"Well, it's like this. You know we have a long weekend next week. Following our tradition, all the brothers will be visiting another chapter across state. It is a brothers only gathering so our pledges will remain here. In previous years we usually had at least one brother who had to stay behind for one reason or another. He had one chore to do, and that was to deliver an envelope to the pledges that would contain their instructions for the weekend."

"Hmmmm, so what do you need?" I asked softly.

He leaned closer to me, looked me straight in the eye and continued. "This is the first time all of us can make the trip, so we need someone to deliver the envelope to the pledges after we are gone. They have been told to keep the weekend clear and to wait for their instructions to be delivered to the house Friday evening at 6:00 pm."

"That's all you need me to do Jake?"

He nodded and added, "And in return for doing us this favor, we can add some instructions for the weekend to have the pledges do some yard work, or whatever for you, just tell me what orders you want added to their list."

At this point I was lucky that I was wearing a tight pair of briefs, otherwise my "rapid rise" manhood would have knocked Jake over. It was the words "or whatever" that set my mind and sex juices in motion.

Thinking fast, I inquired, "Well Jake, I would be glad to help. As far as some work or `whatever' for me, could we do this... just add a note that they will be given a second envelope at 8:00 pm that would include other instructions. That way I can think about what I need done during the week."

Jake smiled and nodded. "You know what Scott, I just had a better idea, why don't you write the instructions yourself. You need to keep them busy all weekend and include a good cleaning of the fraternity house. Have them do whatever you want. I know you were in a good fraternity while in college and should be able to handle it." He smiled again and winked.

I was almost speechless. Somehow I managed to stammer, in a business like tone, "Uh, did you want to see the instructions before you leave?"

Jake's mind had apparently shifted to other matters, "No, I don't need to see them, I'm sure you'll do a good job and I have a LOT to do this week so it will take a major load off me, not to have to plan out their whole weekend."

He extended his hand and inquired, "Deal?"

I grabbed his hand and shook it firmly, "You can count on me Jake!"

And with that he was gone. I stood there for several minutes as my mind raced, `Six, hot, firm young college studs at my disposal for a LONG weekend. What a great opportunity. Even more so because they were all extremely motivated to get into the fraternity and would indeed do "whatever" to get through their pledge period.'

After a little while I wandered back into the main party room. As I entered, I noticed Jake talking to Matt, the fraternity president, in the back corner of the room. Matt was listening intently to what Jake was whispering in his ear. When Jake finished talking, Matt looked up and saw me. He gave me a BIG smile and a thumbs up sign while he mouthed the words "Thank you!"

I returned the thumbs up sign and nodded.

It was time for another drink and to start checking out the gift that had been dropped in my lap.

The rest of the night was my discovery period. I managed to talk with all six pledges and learned a great deal. Needless to say, I did not mention anything about the following weekend.

When I eventually got home, I ripped off my clothes, laid on the couch and began stroking myself. I started thinking about the following weekend and what I could do to those six pledges. I lost track of the number of times I reached "the edge" as I imagined some truly hot scenes. Finally I couldn't take it any more. I got to the edge and let things rip. My body convulsed over and over again, shooting load after load of steaming man juice all over my chest, stomach and face. It was the most intense orgasm I have had since my college days. I drifted off to sleep very quickly, dreaming about "whatever."

The next morning I woke early, got my self cleaned and dressed and headed out to make the rounds of my restaurants. They were all doing very well and had exceptional managers, so I did not need to be too involved. You hire the right people and you can kick back and enjoy the ride.

It didn't take very long to make my quick stops, due mostly to the fact that I was anxious to get out to my country house.

Several years earlier, I had purchased an old estate, far out in the country. It included three hundred acres of beautiful woodlands, a few farm fields, two ponds, and a spring fed creek that was always full of crisp, clear water.

The manor house was set deep in the woods. With a few modifications it could pass for the "Addam's Family" house. It also had some very unique features. The most unusual features were in the stone walled basement.

Somewhere in the distant past it had been the home and "office" for the county sheriff. The basement had 6 small jail cells set into the back wall. The front wall had what could only be described as an engineering miracle. An open stone waterway, about three feet wide that entered the basement, made a semicircle around a stone platform and exited at the other end of the wall. The waterway was always full with that ice cold spring water from the nearby creek.

As I understood it, the sheriff's desk used to set on the stone platform. What a unique office.

After I took over the house, I added a number of features to the basement. It was now a wonderfully equipped dungeon, complete with a St Andrews cross, rack, a large oaken torture table (located on the stone platform), whipping post and more. The walls were adorned with a devilish assortment of whips, paddles, shackles, ropes, chains and handcuffs. Several wooden chests lined the floor along the side wall. They contained a complete collection of toys and torture devices.

Ahh yes, I was proud of this house, and especially it's dungeon.

As I drove out to the estate, I called the caretaker. I told him I was on the way out to the house. I explained that I would be at the house the following weekend and that he should take the weekend off. He gladly accepted the long weekend off with pay and the roundtrip airline ticket to anywhere he wanted to go.

Next I called Andrew. He was a friend of mine for many years and would sometimes help me in the dungeon and cooked for special parties. While the fraternity studs were handsome, Andrew was not. In fact he was pretty much the opposite. At 45 he was overweight and balding yet had a fairly muscular chest and solid arms. Nature was not kind in the facial looks department. His face was pockmarked with scars left from a runaway case of acne and he had several rather ugly warts. Needless to say he did not have a very good time during his teen and college years. He had a deep seeded resentment of handsome young dudes. It was that resentment that made him ideal for my needs. There was nothing he liked more than torturing handsome young hunks.

It was his way to payback all the studs who made fun of his appearance.

Anyway, I told Andrew that I could use his help next weekend. I gave him a rundown of the situation and he eagerly agreed to help. We discussed some more details and I told him to wear the great Executioner's outfit that I had recently bought for him. I thanked him for helping. He laughed and said he should be thanking me.

So things were beginning to fall into place. I would make a quick inventory of my dungeon supplies to ensure I had six of some of the dungeon items I would be using. I would also order some supplies to be delivered early Friday morning. Food and drinks for a party of eight and the obligatory keg of beer... what serious fraternal ritual can be accomplished without a keg!

I was now in high gear as piece after piece of a plan took shape. There would be quite a bit of work to do during the week ahead, but I was looking forward to it.

Monday/Tuesday The week began with the usual flurry of business activity. Though my managers handled things well, I approved all menu changes, "special" job applicants, and all applicants for waiter jobs at the crown jewel of my tiny restaurant empire, `Tammerlane's.'

I quickly worked my way through the week's menu changes and turned to the employment folder. There were three applicants for waiter positions at Tammerlane's and one "special". A `special' applicant was anyone who applied for a job without any waiter or food service experience.

So what was the big deal about Tammerlane's. That's fairly simple. It was the pick of the `trendy' crowd. Decorated in a lavish fashion, reminiscent of a Mongol Emperor's court, it's menu included gourmet dishes from around the world, spectacular entertainment and a horde of the most skilled (and handsome) waiters found anywhere. The place was packed every week.

The attraction for waiters was simple as well. On a typical night, you could easily earn $300 in tips. For almost any college student it was a dream come true, and well worth going through my unique training program.

The applicants in this week's folder were exceptional. Two soccer players and one wrestler, all with experience as waiters, good looks and a serious need for money. All three had signed releases to undergo the special training program for all Tammerlane's waiters. They would serve as a great appetizer for the weekend, so I scheduled interviews for Tuesday afternoon.

I next turned to the "specials" folder. There was only one applicant, Bobby, an 18 year old freshman from Utah. I looked at his photo as I read the "essay" portion of his application that required him to explain why he needed the job and what he could contribute.

His face was very "boyish" and offset by a healthy head of reddish blond hair, parted in the middle and swept back above his ears. The head and shoulders shot was clear evidence of a nice body.

Bobby's story was a sad one. He had a small scholarship but had depended on a mutual fund to pay his college expenses. Unfortunately, the fund he had was heavily invested in the wrong stocks and was now essentially worthless. His parents were in no financial shape to help him and he was determined not to apply for any student loans. He needed the high tips a waiter job at Tammerlane's would generate to put himself through school and would do anything' to get it. He further emphasized that by saying, ... and I mean anything.' The bad news was that he had absolutely no experience as a waiter. The good news was, he was exactly the type I was looking for!

So I scheduled an interview for him as well.

Now, by the close of business on Monday, I had completed all of the physical arrangements for the weekend. It was a pretty intense day, but one that promised incredible rewards!

Tuesday started off as any other day. I had an early breakfast meeting with the restaurant managers and then continued through a pile of paperwork. Before I knew it, my secretary buzzed me to let me know that my 3 o'clock appointment was there. Ahh, yes, Bobby, the `special' case. Since I was just as eager as Bobby, I had him ushered into my office immediately.

When Bobby entered, I was virtually speechless. Dressed in what was clearly a brand new, off the bargain rack suit, Bobby was the classic wet dream. Like the typical teenaged boy, he did not fit the suit properly. Nonetheless, he was obviously trying very hard to appear confident and business like.

As he approached me with hand extended, I quickly surveyed his body. He was a wonderful. In spite of his ill fitting suit I could tell he had a classic teen build. Little or no fat... a flat chest and trim abs and thighs. All of which was topped off with a sweet boyish, dimpled face and that mop of reddish blond hair.

We exchanged some pleasantries and then sat down in front of my desk.

I had decided to get right to the point.

"So Bobby, let's not beat around the bush... I have read your file and as you are no doubt aware, I have discovered that you have no experience as a waiter."

Bobby's face reddened as he looked down to the floor and mumbled apologetically, "Yes sir I know, but I am a really fast learner... I really need this job... and am willing do to anything to get it!"

I laughed, looked him right in the eyes and commented, "Well Bobby, I have no doubt about your need, but tell me more about the "anything" you are willing to do!"

Bobby looked me straight in the eye and declared, "When I say anything, I mean just that. The only exception would be if you asked me to kill other people... or steal from them, that I could not do!"

I laughed again. "Wow Bobby, do you really understand what you just said... I mean what if I was a wild pervert?"

Bobby stared back at me and proudly declared, "It wouldn't matter, I'd do whatever you said to get this job!"

I had no doubt that he meant what he said. I liked his confidence and of course his body, so I decided to give him a chance.

"Okay Bobby, tell you what I'm gonna do... I have three openings right now and I have four applicants. The other three guys have a lot of waiter experience, but I will give you a shot at one of the positions if you can get through one 24 hour period of my training program."

Bobby did not hesitate at all, "That's a deal sir! So what do I do next?"

I smiled, "I like your attitude Bobby. I will need you for an initial 24 hours of training and testing. How soon would you be able to do that?"

He thought for a moment and then said, "I could do it from Wednesday evening to Thursday evening. Most of my classes are Monday-Wednesday-Friday. I have one class on Thursday, but it's a project type of class and you don't have to go every week."

"That will be fine Bobby. Be here at 6:00 pm tomorrow night. You won't need to bring anything special."

Bobby nodded. I stood up and extended my hand, Bobby jumped to his feet and grabbed my hand. His grip was firm and confident. I held onto his hand tightly looked him straight in the eye and inquired, "You do understand what you have agreed to Bobby?"

He returned my look, smiled and tightened his grip, "Yes sir, I do. I will do anything you say to get a shot at this job."

I nodded and released my grip. A quick glance down at Bobby's groin gave me all the confirmation I needed. He was clearly in a full state of arousal. Obviously Bobby needed more than just a job.

I walked him to the door and sent him on his way.

It was now 3:45. The other three applicants were due at 4:00. I went ahead and arranged three chairs in front of my desk. This would be a group interview, the type I really enjoy.

Over the years I have learned a great deal about the psyche of college age young men and most particularly, of guys who are very body proud and who compete in the more aggressive sports.

To begin with, they cannot resist a challenge. They are addicted to proving their manhood through competition. Put a guy in a group of others like himself, give him a challenge in front of the others and his ego takes over.

He feels an irresistible urge to complete the task, to prove to all around him that he is tough and macho.

One of my favorite challenge lines is to declare, "This will be a difficult challenge. Only the best are able to make it through... and those are the ones that get the best jobs." Now, knowing that I have quite a few waiters at my best restaurant it is no great leap of logic to see why these jocks would be anxious to forge ahead. `If all those guys made it, I can too. I want to be one of the best."

Using their ego's and competitive drive is what starts the process. Then I move in for the knockout punch.

Within these well developed bodies there is another powerful force. It's called the male libido, that strong, sometimes overpowering need for sexual release. After establishing a challenge situation, all you need to do is introduce a hint of sexuality and the libido kicks in, in full force. And it is usually like a runaway train. Straight or gay, it doesn't matter, once that ego/libido fueled train gets up to full speed it can't be stopped. Straight guys will give into the urges and engage in gay sex to obtain release from those powerful forces. What's more, most will even do it again just to experience those feelings.

The three boys arrived promptly at 4:00 and were ushered into my office. After a brief round of introductions we all took seats.

All three were dressed casually. Ronnie was the wrestler. Typical for the sport he was in, Ronnie was short and compact. He wrestled in the 149 pound weight class. He had close cropped back hair and heavy black eyebrows that helped frame his beautifully chiseled face. There was clearly not an ounce of fat on the lad.

Kyle was a soccer player, about 5' 11" tall. He had that "well-conditioned" look of a soccer player. He wore his dark brown hair long, with streaks of blond frosting throughout. Though not as muscular as Ronnie, he was clearly in great shape.

Phil was also a soccer player and was just about as tall as Kyle. His hair was golden blond and curly. He was not as defined as Kyle but was quite good looking. A little on the skinny side and very "boyish" looking it was hard to believe he was in college.

I reached for their application folders and spread them out in front of me. I looked the folders over, muttering ah', hmmm', and so on to myself several times. I could tell that all three were getting nervous.

Finally I looked up, "Well, I see you boys have a lot of experience as waiters!"

They responded in unison, "Yes sir."

"That's good boys. And all three of you seem highly motivated to get a job at one of my restaurants."

They responded with a `Yes, sir" and then Ronnie added, "Uh sir, I know all three of us really want to work at Tammerlane's... I mean we know all of your restaurants are great, but Tammerlane's is the best... and, well..."

I laughed, "Yes, and let's be honest and upfront boys, the tips are outstanding there."

They admitted it and so I continued.

"Well boys, we have a situation here. At the present time, I have three openings at Tammerlane's, but I have four applicants and probably more by the end of the week. All applicants for the top positions must take part in my, shall we say, unusual training and testing program. It is very difficult and will test every part of you. If you make it through, you are guaranteed a job at Tammerlane's where only the best can work. If you can't cut it, you may still apply to work at one of my smaller places as a busboy, dishwasher, or perhaps as a substitute waiter. But to get the best jobs you will need to make it through the program."

I glanced at the three. There were some minor signs of nervousness, but it was fairly obvious that their competitive egos were beginning to take control. Their common sense was already receding.

"Now I know all three of you have signed releases for the program already, and that is good. I just need to make sure you understand what you would be agreeing to. You will commit yourself to completing the testing program. During it, you will be required to do anything you are told. The only stipulation being that you will not be required to commit any crimes and you will not be marked or maimed. Understand?"

They glanced at each other, and followed with three distinct "Yes sirs." As they did I noted their bobbing adam's apples, a clear sign of some fear, but the rest of their bodies exuded the excitement of the challenge. They were determined to get the jobs they wanted and to be part of "the best."

So now was the moment to light the other burner. I nodded and glared at them, "And when I say `ANYTHING', I mean absolutely ANYTHING!" I held my menacing glare and watched as all three quivered for a brief moment, their response came quickly, "Yes sir we understand and will do absolutely anything."

I smiled and rose to my feet. The boys stood as well. As they did, it was obvious that the libido flame was also growing rapidly, as evidenced by the rising in there groins. Ronnie was in the lead though, sporting a monster erection that was dang near impossible to hide. The three stood with their hands covering their private areas. I took my time coming around my desk. I extended my hand to each. As we shook hands, I was further amused by their dilemma. One hand was not sufficient to cover their hardons.

I told them to go home and to figure out some times when all three would be available for a twenty four hour initial test. One of them was to call me the next day to discuss possible times. We shook hands again and they left.

Ahh, yes' I thought, No doubt the three will have some unusual dreams tonight.'

After leaving the office, I went to Tammerlane's for dinner. I treated myself to some special off the menu items. As I ate, I looked at my waiters and let my imagination soar.

By the time I got home, I was ready. I stripped off all my clothes and began typing the instructions for the Phi Sig pledges. The waiter's training was nothing compared to what these guys would be facing on the weekend.

(To be continued)

NOTE: The full physical/mental/sexual challenges kick into high gear in Chapter 2, beginning with Bobby. If you have any suggestions for any of the upcoming encounters send them to westwoodscotty@hotmail.com. If I can work them in I will.

Feel free to suggest some devilish challenges for the pledges OR any of the boys mentioned. LOL, like, "I would like to see Ronnie (or whoever) have to do this, or have this done to him, etc."

Next: Chapter 2


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