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Pledging to a Fraternity

"Finally! Pledge Week!"

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They had all already had six weeks of doing silly things as part of being pledged to the fraternity and it was finally here, pledge week, and Jason was anxiously looking forward to the night he would make the pledge. His best friend, who was a year older and already had a year of college under his belt, was a member of the same fraternity. When asked what he would have to do to pledge, Jordan would not say. All he would do was smile.

Both he and Jordan were from a small town where everyone knew everyone’s business. Both were football jocks and they had their choice of any of the cheerleaders…or any girl in school for that matter. Being jocks they had a reputation to uphold, so to speak. While Jordan’s track record of getting laid was for real, Jason was embellished some. He was not a virgin but neither was he a cocksman like Jordan.

Tonight was show and tell where he and the other five pledges would see what they would have to do on their night. None of the other fraternities did this. They would be in a room with a two-way mirror where one of the older fraternity brothers would act out the pledge. When it was time, Jason headed to the fraternity house, where he was shown into a semi-dark room where two of the other pledges were already seated. Once they had all arrived, Jordan stepped in front of the row of the pledges and raised his hand for them to be quiet.

“All pledges please sit on your hands and do not remove them at any time during this demonstration of the pledge you will be doing this week. Removing your hands will earn you three strikes with the paddle. Do I make myself clear?” he asked. “Oh, and there will be no noise at all.”

All agreed and quickly sat on their hands, anxiously waiting to see what was on the other side of the two-way glass. When the curtain parted, a young woman was sitting on a table, nude, with her legs spread apart. Her fingers were gently pulling on the soft blonde hair, so pale it almost looked like she was bald, of her pussy while looking straight at the window. She had medium size boobs, about a 36 C, a good mouthful. Her free hand was pulling at her nipples.

Jason found himself getting hard, wondering if the other pledges were having the same feelings. The urge to stroke his cock was intense and he found himself wiggling uncomfortably on his chair, trying to rub his thighs together to ease the itch. Over toward his left, he heard a small moan and then Jordan ordered quiet. Suddenly she was no longer alone in the room as Rob walked into the room. Seeing him a big smile came over her face.

Breaking the silence of the room, Jordan said, “Each of you pledges will be judged on your pussy eating skills and how well she orgasms. And yes, you can suck her tits if you want. Each one will have thirty minutes to bring her to as many orgasms as you can during that time but she cannot bring you off. You can do it yourself after you have pledged. Now watch the master at work.”

Rob was a senior and was a ‘so-called legend’ around the college as being one of the biggest cocksmen on campus. It was also rumored that he had an eight-inch very thick cock and if a girl was lucky enough to be pegged by him he paid for them to have a small blue ribbon tattooed on their breast attesting to that honor.

Looking the girl up and down he leaned in and kissed her, his hands entangling in her hair as his tongue plundered her mouth. After several minutes of hard kissing, Rob moved down to her breasts, rubbing his fingertips over her nipples, making them into hard little peaks. Moving to her right side, the pledges on the other side of the window could see how wet her pussy was becoming just by playing with her nipples. Rob finally moved between her legs, still working on her nipples as she leaned back on her hands, moaning in delight.

The moment that his tongue touched her pussy, she let out a squeal, her thighs clamping against his head tight as she pushed her pussy into his face smearing her pussy juices all over his face. Once she relaxed her thighs, Rob knelt down on the floor and put her legs over his shoulders as he brought her forward until she was almost hanging off the table. Taking his hand he began to lightly stroke her pussy as he started to lick and suck her clit. Taking a pussy juice lubricated finger he inserted it in her ass moving it in and out as he stroked her pussy.

In no time she was starting to wiggle on the table, trying to be careful not to fall off. Switching around he started to lick her sex slit as he rubbed her clit. They could hear her moaning and the sound of Rob’s slurping tongue. It was almost more than Jason could handle as he felt the front of his underwear becoming wet from the leaking precum. Taking his eyes off the window he glanced around to see where Jordan was. He saw him off to the left side of him, his eyes glued to the window…or so he thought.

Slowly he slid his right hand out from under his thigh watching the action going on behind the two-way mirror. At this point in time, he wished he had worn basketball shorts instead of jeans. It would have made it easier for his hand to slip inside the leg and do some readjustment. Glancing over at Jordan he figured he was still safe so he inched his way to his zipper and pulled it down, reaching inside to adjust his erection.

“Is your hand where it is supposed to be Probie?” Jordan’s voice whispered in his ear, making him jump.

“No sir,” he whispered back quickly zipping his jeans and putting his hand under his thigh, wondering how he could have been so careless and not see Jordan move.

“You will be dealt with after the show. Eyes front and center Jason.”

After thirty minutes the girl was a wet mess on the table and Rob was ready to leave after giving her seven orgasms. He looked toward the screen and held up seven fingers, smiling as the curtain closed. Before the sound was turned off they could hearRob say, “My turn Susie, suck me off.”

When the lights came on, Jordan said, “That, Probies, is your measuring stick,” as he looked around at all the new pledges. He could see a couple of them moving uncomfortably on their chair with a visible hard-on. “Now on the back of each chair is a day and that is the day you will take your pledge to our fraternity. After you have pledged you may not tell any of the other pledges how you did or what the girl looked like. If any breaks this pledge of silence your pledge will be revoked and blacklisted to join any other fraternities.”

Jordan stood there looking at each one in turn until he got to Jason. “Jason, will you come to the front of the room and on your way, pick up the paddle from the table on your left side.”

Jason’s eyes grew wide as he just stared at Jordan, his best friend. All of the other pledges looked at him, wondering what he had done. When Jason got to the front of the room he handed Jordan the paddle and started to go back to his chair when Jordan’s hand clamped down on his shoulder stopping him.

“What was the one thing I specifically told you to do?” he asked everyone in the room

“Sit on our hands and not remove them,” they all answered in unison, including Jason.

“Well, apparently Jason here thought he was exempt for some reason or other. He just could not resist touching Mr. Weenie,” Jordan said looking at Jason. “Drop the jeans and bend over, grabbing your ankles.”

Jason looked at Jordan as if he had grown two heads. He could not believe his best friend was going to paddle his ass. He started to call him on it but then decided against it, although he would be sure to bring it up when they were alone later. Very slowly he unfastened his jeans and let them drop, then reached down and grabbed his ankles, feeling his face turning red in embarrassment. Standing to the side, Jordan raised the paddle and brought it down three times on Jason’s ass.

You may pull up your jeans now,” he told Jason. “Now everyone, reach behind your chair and look at the day you are to be here, then grab a pen on the desk, sign the date on the back, leave them on the desk and you may leave. Each pledge will need to be here at six o’clock on their appointed evening. Probies dismissed.”

Each one quickly took the tag off the back of their chair, made note of their day, and then did as Jordan told them, all anxious to go somewhere private and jack off.

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As soon as all of the other pledges left the room, Jason shut the door and turned to face Jordan, “What the fuck was that all about bro? Do you get off on throwing around your authority? And for your information, I was not playing with myself. I was only rearranging myself to be more comfortable.”

“It does not matter what you were doing Jason. The fact of the matter is you did not sit on your hands as ordered. You knew the consequences.”

“No one else but you saw it so you could have let it slide.”

“I let it slide for you because you are my best friend would get me in big trouble and no one else would listen to me either. You were punished so let it go.” Jordan said gathering up the slips of paper.”So which day is your initiation Jason?”

“Tuesday,” he said, “Now I have to get to class.”

Jordan did not relish having to do what he did to Jason but he had had the same thing happen to him and it didn’t kill him… although Jason may be ready to after the pledge, as a sly smile came over his face remembering his pledge day.

~~~~~~~~~~~~

That Monday at precisely six o’clock Paul was led into the same room Rob had been in, anxious to prove to those he knew would be watching that he could do just as good a job, if not better than Rob. The girl had yet to arrive.

Paul, I wish you luck,” said a voice, which he recognized as Rob’s, come over the speaker. “Your girl’s name is Ophelia. She will be in there in a moment. When we say go, you will have thirty minutes to make her cum as many times as you can. The record is ten times.”

They let him stew for another five minutes and then Ophelia strolled in. Paul was a little disappointed that she did not have big boobs because he was a boob man. She was about five-foot-seven inches, had dark hair that reached her shoulders and legs that did not seem to quit. She was wearing a tube top and mini skirt. Both sized each other up for a couple of minutes, and then she sat down on the table.

“Your time starts… now!”

He stood between her legs, pulling her head towards him as he kissed her passionately, their tongues doing a mating dance of their own. Very slowly he pulled down her tube top, sucking first one, then the other nipple into his mouth while his hands made its way under her skirt toward her pussy. Suddenly he stopped and pulled back, looking at Ophelia in surprise.

“I don’t need to pledge to a fraternity that bad,” as he left the room, leaving Ophelia sitting there just smiling out at the others in the room. She readjusted her top and also left the room.

~~~~~~~~~~~~

On Tuesday Jason walked into the fraternity house and to the room where he would be taking a pledge. By this time he and Jordan had talked things over and all was forgiven. As he walked into the room, Ophelia was already there. He, like Paul, was a bit disappointed that she did not have the type of tits Rob’s girl had but he could handle it. Rob gave Jason the same speech that he had given Paul. When he gave the go-ahead Paul suddenly found himself feeling a bit nervous and a little embarrassed. He knew Jordan was watching and thought that he was as big of a cocksman as he was but Jason was harboring a big secret. Taking a deep breath he leaned in to kiss her and as he did so, her tongue brushed over his lips, then nipped his bottom lip. They kissed for several minutes as his hands pushed down her tube top, exposing her tiny A cup breasts.

His fingers encircled her nipples, pulling them taut, causing her to moan and grab his hair, pulling him closer. Jason then moved to the other breast doing the same thing. Stepping back, he pulled Ophelia off the table and reached behind her, unfastening her skirt and pushed it down over her hips, leaving her standing there in a pair of black panties. As he went to palm her pussy Jason got a surprised look on his face, then he felt the heat rush to his cock. Without a second thought, he pulled her panties down, helping her step out of them.

Reaching out he gently touch Ophelia’s semi-erect six-inch thick cut cock, swishing his tongue across the head and around it while stroking her. Now he knew why Paul had suddenly decided not to pledge. Ophelia was a transvestite and Paul would not suck a cock to get into a fraternity. Reaching down with his free hand he cupped Ophelia’s balls squeezing gently, earning another moan from her.

Leaning against the table, she braced her hands on it, enjoying the feel of his lips and tongue on her cock. “Oh baby,” she moaned. “Work that magic tongue on my cock. Make me cum.”

On the other side of the window, Jordan could only stand there and stare at his best friend sucking on a cock and apparently enjoying it. ‘Is he gay or bi?’ Jordan wondered.

The other members of the fraternity also stood in awe as they watched Jason. They never expected to have one who was gay or bisexual join their fraternity before. Usually, when the new Probies take their pledge, they would bring Ophelia off by hand once they knew she was a transvestite. None of them expected a Probie to actually suck her off.

Moving down her cock, he got to her balls and took each one in his mouth rolling them around on his tongue while stroking her. By this time Ophelia was gripping the edge of the table, moaning loudly as she moved closer to her orgasm. Jason could sense she was close and moved back to her cock, taking her all the way in, his lips gripping her tight, pulling her cum to the top.

“Oh fuck me,” Ophelia moaned as she started to fuck his mouth, letting go of the table to grab him by the hair, fucking him hard and deep. “Pull back, I am ready to cum,”

Jason did not pull back but continued to suck her hard and deep, squeezing her balls with his one hand, Ophelia tried to push him back but finally, she could not control herself any longer and shot down his throat. It had been a while since he had gone down on a man so at first Jason gagged and some ran out of the side of his mouth to the floor below but soon he managed to swallow the rest of her seed. Sucking hard on her now deflating cock, Jason drained her dry. Sitting back on his heels he just looked up at her. Ophelia leaned down and they kissed, their tongues dancing with each other.

Standing up, Jason faced the mirror and said, “I am not gay Jordan but I am bisexual,” and with that, he kissed Ophelia and asked for her number, which she gladly gave to him. He kissed her again, patted her now deflated cock, and walked out of the room. He just wished he could have seen his best friend’s face when he found out that Jason was bisexual. Suddenly he started to laugh at the thought of what the other four Probies were in for on their pledge day. Would they or would they not go down on Ophelia or be like Paul and be disgusted and not pledge.

As he stepped out on the porch, he heard Jordan hollering for him to stop so he did, turning around to face him.

For a moment they just stood there looking at each other, and then Jordan said, “We have known each other since you were in seventh and I was in eighth grade and I had no idea. Why didn’t you tell me? Were you scared I would hate you or make fun of you?”

“I did not realize I was bisexual until a couple of years ago. Remember that weekend we went out camping and you met that girl? Your older brother had bought us beer and we were pretty drunk. While you were fucking that girl in our tent, Dale made a move on me and one thing led to another. He was gay and I was scared I was too but I still loved pussy so that is when I realized I must be bisexual.”

“You did not have to go down on Ophelia you know. You could have just given her a hand job,” Jordan said. “Or be like Paul and get mad and refuse to pledge.”

“I did what I wanted to do,” Jason said. “Doesn’t she get mad at you all using her like that?”

“No, it was her idea in the first place.”

“Well, if it bothers you or any of the other fraternity brothers that I am bisexual I won’t pledge,” Jason told him as he started to walk away.

“You are in bro. Don’t worry about it,” Jordan called out after him. “You are rooming with me.”

Turning back to look at him, Jason smiled and asked, “Sure you feel safe with me knowing I am bisexual?”

“I will take my chances,” he said as they gave each other a bro hug.

Over the next four nights, all of the other four Probies made their pledge by giving Ophelia a hand job.

 

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Written by freespirit13
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