The Fraternity Ch. 01

Author's note:

This story is meant to be a fantasy. As such, many points of reality are put to the side, such as safety and pregnancy, as well as others.

Additionally, this series will cover a wide range of sexual activities. I will try to cover them in the into, but please be aware. All characters are at least 18 years of age.

Following comments that I have gotten previously; I know nothing about how fraternities work. Everything here is meant for the purpose of telling a story and titillating the reader and is not meant as a portrait of reality. I love hearing from readers, but if you comment that it wouldn't happen that way in real life, well, that's why it's a fantasy.

Thanks to my amazing editor ResqJack!

Topics: Cross-dressing, Transgender, Oral, MT

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Dave knew that he was smart. It was how he had gotten accepted to such a good university and the academic scholarship that was paying for most of his tuition. He had managed to scrape up just barely enough to cover the rest for his first year and was hoping to find a job to cover basic living expenses. In part, that was why he was so excited about the email that he had gotten regarding an invitation to pledge to one of the top fraternities in the country, Alpha Gamma Sigma. After receiving the invite, Dave had looked into them. Not only were they well known and had alumni everywhere, which would help him down the line, but they also had free on-campus housing for members, which would save him so much money. He wasn't sure why they had picked him, but he wasn't complaining.

Following the instructions in the email, he showed up to campus a few days before and was met with a group of other students, all guys, who were there to join as well. It was clear that some were second-generation or younger siblings from well-to-do families, but there were also some that seemed as lost as Dave felt. They were met by an upperclassman who checked who they were and greeted them, showing them into the House. The name House was a misnomer for what was a small mansion with over two hundred rooms in it. Once they were all processed and in, another upperclassman gathered them all together.

"Welcome all of you to your now and future home, Alpha Gamma Sigma. My name is Peter Lancer, and I am the chapter president of AGS. Before we begin the tour and get you guys acclimated, I need to cover some basic rules. The way that this works is that you are all adults, and as such, expected to follow the rules. There will be consequences for breaking them as if you had broken rules in the real world. Rule number one, no females are allowed in the House. This had always been a rule, but especially in today's current climate, AGS does not need any false complaints about rape tarnishing our reputation. And I say false because I know that none of my brothers would dare rape a woman and if we find out that it did happen, there will be consequences. Rule two is that AGS business is AGS business and does not involve anyone else. If you have a problem, you can always come to me, and if your problem is with me, then you can take it to the regional board. There are other, smaller rules, but we will get to them as they come up."

He then proceeded to take them on a tour of the House. Dave was in awe of the facilities at hand. Everything seemed state of the art and designed to make studying as easy as possible.

"Now, everyone had been assigned a room, correct?" Peter asked. When everyone nodded he continued, "Good. Go get your stuff put away and settled and then let's meet back here before finishing up your tour and we get to dinner."

Dave found his room and new roommate, Tim. They introduced themselves and started unpacking. They had a half-hour to get aquatinted before Peter called them back together.

"Now, before we feed you, we come to the next stage of your introduction to AGS. You are all pledges and will remain such until the end of the year when you are formally accepted in. As pledges you have responsibilities. Those include working in the cafe, which is our in-house restaurant, which includes a full bar. On one hand, while you are working, you are entitled to free food and drink." As he talked, he was walking them down the hall, leading them into a room they hadn't seen yet, which looked like a locker room. "On the other, you will be expected to be dressed appropriately," he said, opening a large closet.

Inside, Dave could see what could only be described as a cross dresser's paradise. There were racks of women's clothing of all shapes and sizes, along with a staggering number of wigs and drawers containing who knew what.

When shouts of protests came from everyone, even those who were legacies, Peter held up a hand land loudly called for quiet.

"Those of you who have someone in AGS that they trust are welcome to talk to them about it afterward. I promise that they have gone through this as well. Now let me finish. As I said, there will be a schedule as to when you need to work, but and you are expected to be here, in proper dress, which includes being clean-shaven, and serving those that come in. And to clarify and prevent any misunderstandings, by serve, I mean in any way that you are asked to, including with your mouth and ass."

He held up a hand again to stop the protests.

"This is something that every single member of AGS has gone through, myself included. It is really quite simple. Once you have all gotten changed, you will choose a female name. As far as anyone in AGS is concerned, she is a completely different person from you and what she does has no reflection on you. That is, of course, assuming that you make an effort to separate her from you. In other words, if you don't make an effort to be something other than a guy in a skirt and wig, then the person seen sucking cock will be the real you and not someone else. Understand? Good. Going back to a previous point, any time you have your female persona active, you are considered working and can eat and drink for free, but you also need to serve.

"Yes? Good. I know that for some of you that is meaningless, but I know that not paying for food and drinks was a huge draw for me and plenty of the other members. Please also keep in mind that alumni do come by, including some of the teachers and staff, and they do occasionally bring guests who have been properly vetted. You will serve them all as well, as it is part of what makes it possible for us to do everything that we do here on campus. You have each been assigned a mentor to help you adjust to the process and to teach you basic skills. Listen to their advice. They will call out your names and get started. I expect to see all of you in the cafe in an hour."

A group of upperclassmen who had entered behind the pledges started calling out names. To Dave's surprise, Peter called him. He followed him over to a locker at the side of the room.

"I took the liberty of already pulling out things for your first time. I can see that you have questions, but why don't you start getting undressed while you ask them."

Having been in locker rooms before, Dave didn't feel any real hesitation getting undressed here. As he pulled his shirt over his head, he started to ask the questions that were on his mind.

"Not that I'm complaining or not grateful, but why did you pick me? I don't know how I even got on AGS's radar, let alone an invite."

"To start with the last first, you know how I mentioned that a lot of the staff are either alumni or guests of the cafe? Well, that allows us certain liberties, like the ability to go through incoming freshman records and find appropriate candidates. That is how we found you. You looked good on paper, so we investigated more. After fully vetting you, which means that I probably know more about you than you do, we sent you an invite."

Dave stopped and stared at Peter with a frozen look of shock as he was in the middle of pulling down his pants.

"First piece of advice. Shave completely down there," Peter said, pointing to Dave's crotch. "I have never had anyone complain about my not having hair down there, and I have heard both guys and girls complain about it being there."

Dave blushed and resumed undressing, not looking Peter in the eyes.

"Going back to why I picked you, there are a couple of reasons. Here," he said, holding out a pair of black lace panties to Dave. "Start with these." Dave hesitatingly took the panties while Peter continued. "First, you remind me of myself. We have similar backgrounds and interests. If you need help with any of your classes, let me know, as I'm pretty sure I took all of them already. Second, I think that you will be the perfect fit for a new project we are trying, so I wanted to mentor you through everything from the beginning, but we will get to that later. Let me help you adjust that," he said reaching over to Dave's waist. "Start with getting yourself situated in front like this before pulling up the back of the thong."

Peter, obviously having no compunction about touching Dave's cock adjusted it within the small lace pouch at the front before pulling the back of the thong between Dave's ass cheeks. Dave flinched a bit as Peter pulled the place into place and then relaxed and tried to adjust to the uncomfortable feeling of having something back there.

"Next comes the bra," said Peter, handing Dave a bra. "Try to always make sure it matches your panties. It is worth the effect. Do you think that you can figure out how to put it on?"

Dave struggled for a minute before figuring it out.

"Perfect. These go inside the cups to fill them out," Peter said, putting a peach-colored, softball-sized, squishy object into each side. "In general, you won't be taking off your bra, but later I'll show you how to attach actual fake tits. Next, come the shirt and skirt."

Dave took the proffered clothing and pulled them on. The skirt was black and came to the middle of his thighs. The shirt was bright red, and while it covered his chest completely, the arms were completely bare, as was his stomach.

"You are looking great. Next shoes and hair. We should even have a minute or two for makeup since you cooperated so nicely."

Dave bent down to get the shoes out of the bottom of the locker and felt the thong pulling at his ass and dick. The shoes turned out to be a pair of black strap heels that took him a minute to get on. Once that was done, Peter situated the blonde wig on his head, which matched his own natural color.

"Feel free to try other colors as well, but I figured that your own would work best for the first time. Let's put a bit of makeup on so that you can get the complete effect when you look in the mirror."

Peter took 5 minutes and touched up Dave's face, explaining as he worked. When he was finally done, he told Dave to stand up.

"Take your first few steps carefully. Walking in heels is a new experience. Take smaller steps and put one foot in line with the other."

It took Dave a minute to figure out what Peter was telling him, but he soon was and began to feel the difference in the gait.

"You are a natural. Now walk towards the mirror and see what this part of you looks like before choosing your new name."

Dave approached the large mirror at the end of the row of lockers and couldn't believe his eyes. Staring back at him was a sexy, long-legged blonde girl.

"Turn around and pull up your skirt a bit," whispered Peter.

Dave did as instructed and looked back to see the girl flashing her ass at him with the hint of lace peeking out at the top.

"Be honest. You'd fuck her, wouldn't you?" Peter whispered again.

Dave nodded, entranced by what he was seeing.

"What's her name?"

Dave had been thinking about it for a while, but looking at her, he decided.

"Diane."

"Good choice. I need to go get things ready in the cafe, but wait with everyone else until you get called in."

Diane found herself waiting awkwardly, as she watched the rest of her pledge group finish getting dressed. It was obvious that some were more suited to this than others, and that some resented it more. She was fascinated by the wide array of styles of clothing that fit the pledges, which ranged from conservative to outright slutty. Comparing herself to the others, she was really pleased by what Peter had picked out. By the time they were called in, they were all fully in dress and ready. They were each given a name tag with their chosen names and then guided into the cafe in a line towards a small stage, where a large group of AGS members waited for them. They were then all stood together where they posed for a group picture. They were then each called by their new names and introduced to the waiting crowd and had their pictures taken.

"Now, it is tradition," Peter announced, "that each of the new pledges thanks their mentor for helping guide them through their first change. Pledges, please approach your mentors."

Diane slowly made her way to Peter.

Once each pledge was in place, he whispered to her, "I expect you to be an example for everyone else." She nodded. "Good. Kneel."

Sudden understanding came over Diane as she got down on her knees before Peter. Hands trembling, she reached for his belt and unbuckled it.

As she pulled his pants and underwear down, she looked up at him and said in a soft, but surprisingly clear voice, "Thank you."

He smiled down at her, clearly approving. She blushed and looked down to find herself face to face with her first cock. Not that she had never seen one other than her own, but it was the first time that she had ever had one this close to her face, let alone as hard as this one was. Looking at it objectively, it was probably around the same size as hers, which meant average size and length. But from this angle, expecting it to go into her mouth, it looked huge. She heard other girls thanking their mentors and of pants being pulled down. Knowing that she had to take the plunge, she leaned forward and kissed the tip. Having taken the first step, she was then able to make herself lick the tip, tasting cock for the first time.

To her surprise, she didn't mind the taste, nor that of the bit of precum that had leaked out. Building up courage, she opened her mouth and took the head of Peter's dick in, wrapping her lipstick-covered lips around the top of his shaft. She wasn't the most experienced, but the look of pleasure on Peter's face as she swirled her tongue over his tip matched her own memories of pleasure when it had been done to her. She focused on that, trying to do the things that had felt good to her, bobbing her head up and down on his shaft, gently caressing his balls, marveling at just how perfectly hairless he was.

She was careful not to take too much into her mouth so that she didn't gag, and rush throwing up. It didn't take too long before she felt his balls tighten up and before she could mentally prepare herself, her first load of cum started filling her mouth. She had to fight her instincts to pull away, knowing your much better it felt getting sucked through an orgasm. She found that she barely tasted his hot seed as it spurted into the back of her throat and she swallowed. It was only as his orgasm died down that she got some on her tongue, and while it didn't taste good, it wasn't horrible. Looking up at Peter's face, she sucked out the last drop of cum, causing him to shudder slightly with pleasure. She then kissed the tip of the not softening penis and tucked it back into his pants.

Looking around she could see that her fellow pledges were on their knees, sucking cock, with various degrees of success and skill. She heard and saw some who looked like they were born to give head, including one girl who was going so deep each time she went down that especially on a cock that long, it had to be going deep down her throat, and she was doing it without issue. On the other end of the spectrum, she could hear girls gagging and saw disappointed faces of guys who were clearly not enjoying what was being given. She saw a couple of guys give up and start face fucking their pledges. Everyone watching seemed to be taking notes and commenting softly, which made Diane suddenly feel super self-conscious and she felt the heat rush to her face. Peter walked away to talk to some people, so she awkwardly got up and stood there for a moment before heading to the bar. The bar was manned by an upperclassman who asked her what she wanted to drink.

"Gin and tonic for the lady", Peter said from behind her, casually placing his hand on her ass. "And a nice bourbon for me, Dennis."

Peter left his hand on her ass until they were served. Leaning over, he whispered into her ear

"Sip, don't gulp. Remember to always keep up the illusion. Especially if you are going to be drinking heavily, make sure to get something with an umbrella in it. But watch how much you drink tonight. There will be plenty of time to get plastered going forward."

She accepted her drink demurely and felt a flush go through her body as he squeezed her ass before letting go to accept his own drink. She didn't know what it was, but she was shocked to find herself getting hard against the lace fabric. Peter led her over to a group of people to introduce her as other girls started approaching the bar. After a short time, dinner was announced, and everyone made their way to tables that had been laden with food. Diane was pleasantly surprised at how good it was. After dinner, they moved back to the barroom where music was playing, and people started dancing. Another student approached and asked her to dance, and after a quick glance at Peter, she accepted. It was weird being the girl while dancing, and the heels made it extra challenging, but she didn't do too bad of a job, even with the distractions caused by the thong pulling tight against her ass and balls each time she moved. As the music picked up the tempo, the guy she was dancing with started grinding his obvious erection against her ass. She shivered, feeling the hardness press against her, and was both relieved and disappointed when he spun her back around.

She was still confused about her own feelings when he pulled her in close and whispered huskily in her ear, "Get on your knees."

Shaking a bit and not really sure why, she dropped down, finding herself face to face with her second crotch. She watched as he opened his pants and pulled out his cock. It was smaller than Peter's, which meant that as she took it into her mouth, she managed to get most of it in before she had to back off. From the sound of him moaning, she knew that she was doing a good job. She paused every few bobs to swirl her tongue over his tip. It didn't take long before she felt the telltale signs of an impending orgasm. As the first blast of cum started filling her mouth, Diane realized that she didn't even know his name. She felt her cheeks flush even as she heard him groan as she swallowed his seed. After she licked the last of the salty cum from his dick, she let his member fall from her mouth and settled back on her heels.

She opened her mouth to ask his name as she started to get up, but suddenly another cock was being shoved into her mouth. Knocked back into her knees, she started to fall over but was quickly caught by the hands of the guy whose dick was in her mouth. Before she could even really wrap her head around what was happening, he moved his hands from her shoulders to her head. As opposed to the last two blowjobs that she had given, this guy showed no interest in letting her do the work. He immediately began fucking her face, thrusting in and out of her mouth, holding her face in place. He also was not at all careful about going too deep, and while he wasn't pressing down into her throat, he did hit the back of her mouth enough to make her gag. She could feel the drool pouring out of her mouth as he face-fucked her. She didn't know what to do and just grabbed hold of his thighs for balance. Tears were leaking from her eyes by the time he pulled her face tight against his crotch and unloaded into the back of her mouth. She choked and gagged as her mouth overfilled with cock and cum, and a lot of it poured out of her lips, dripping onto his balls and her shirt.