The Fraternity Ch. 02

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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.

If you have not yet read the previous chapter, go back and do so, things will make more sense.

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, Anal, Toys, MT, TT

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Dave woke up in the morning and looked around with half-opened eyes and a brain not firing on all cylinders. It took him a second to place that he was in his new fraternity house room. After that processed, he noticed that there was a girl in his roommate's bed. Struggling upright, he took another look, and then events of the previous night crashed back in on him he realized that it wasn't a girl in his roommate's bed, but rather his roommate, Tim, or Tina, he wasn't sure what to call them, given that they were only half-dressed as Tina. But either way, Dave did have to admit that there was something incredibly sexy about them laying there in a short black dress that had ridden up in the night exposing black lace panties. It was novel for him that the fact that those panties contained a cock didn't bother him or turn him off, but he shrugged mentally and headed out of the room looking for coffee. In the main common area, there was a sign directing pledges to report to the Cafe for breakfast and their schedules. He knew that there were still a few days before school actually started and the "fraternity orientation week" made a lot more sense after yesterday. He found people setting up a small breakfast buffet under the watch of Peter who was sitting and having a cup of coffee.

"Good morning," he said when he noticed Dave. "I didn't expect the first of the pledges for at least another half hour, so things aren't ready yet, but feel free to grab a cup of coffee."

"Thanks," mumbled Dave, heading to the coffee station. "So, what's the plan for today?" he asked after imbibing some of the rich dark coffee.

"As I'm sure you noticed last night, being a girl isn't something that everyone picks up easily in a half hour. So we take a couple of days to teach and train you. Everything you need to know, at least to start. How to dress, walk and act like a girl. How to put on makeup. And how to suck a dick and get fucked in the ass."

Peter said the last bit as matter of factly as he had the rest of it, so it took Dave a moment to process what he said. Before he could respond, Peter continued.

"This is the last time for the next three days that you will be Dave. You are going to live as Diane for that time. From personal experience, the quicker you can make the mental adjustment, the easier it is. And here come some of your intrepid pledge mates now. Get them settled and started, while I go and wake the rest of them. The first morning is always hard."

Dave got people started on breakfast as Peter headed out. Over the next half hour, the rest of the group showed up, including Tim, who had showered and changed into his own clothing. Once everyone had a chance to eat, Peter gave another speech about the plans for the next few days, emphasizing that this was the last time he expected to see any of them as guys for the next three days.

"During the first day, I do understand that there will be a period of adjustment, but after that, or once your instructors think you should know better, mistakes will be punished in a matter fitting the girls you are meant to be. Any questions?"

"What does that mean, exactly?" one of the pledges asked.

"Are you that eager to find out?" Peter responded with a smile. The room laughed and he continued, "I didn't think so. Alright. Let's get moving."

The pledges were sent to the locker room where they had identical simple black bras and panties waiting for them in their lockers. Diane pulled out the fake boobs she had worn the night before and slid them into her bra, filling it out nicely. A couple of the other girls had the same idea, and as the rest noticed, they quickly followed suit. The girls were then herded into a room with tables around the edges that each had a mirror and a box of things on it.

By the time lunch came around, Diane's head was swimming with information about women's clothing and makeup, two things that were infinitely more complicated than she would ever have guessed. She had, however, managed to finally do a decent enough job of putting on her makeup, which was subtle except for the bright red lipstick which made her mouth stand out enticingly in the mirror.

After lunch came lessons about anal. The lessons were surprisingly frank and open about what to do and not do, how to prep, clean and use proper hygiene. At the end of the lesson, each of the pledges was handed a small black butt plug.

"Start with these," their instructor told them. "I expect each of you to be ready for the bigger size before dinner. Maybe if you are really good girls, I'll let you choose a princess plug for later."

Looking around the room, Diane shrugged. Following the instructions they had been given, she applied a generous amount of lube to the small silicon toy that was not much bigger than her finger. Lifting her skirt over her ass felt weird in the middle of a classroom, even though she had gotten dressed in here in front of everyone not long before. She pulled down her panties and bent forward a bit so that she could apply some more of the lube to her asshole. She felt a shiver run through her body as her finger penetrated her virgin anus for the first time. After making sure her hole was ready, she grabbed the toy and lined it up. She heard one of her pledge mates moan slightly and glanced over to see Tina shifting around on her chair, clearly grinding the plug against her ass.

Suddenly a lot more eager, Diane pressed the tip of the plug into her asshole. An involuntary gasp escaped her throat as her tight butt was penetrated for the first time. She sighed as it easily slid into place. She tried moving in different ways and found that while she definitely felt it, it wasn't uncomfortable or too big of a distraction. She pulled up her panties and tucked her erect cock in so that it didn't make too much of a bulge. Having finished she looked around the room to see that most of the girls were finishing up, and based on faces, some were feeling it more than others.

"If everyone can please focus back up here for a minute," their instructor called out. "We are going to take a break for fifteen minutes. Use that time to get a drink or whatever else you want, but most importantly, move around. Get used to having the plug in you. Assuming that you put it in all the way, it won't come out by itself. Now go. I expect you back here in fifteen."

Walking around with the plug in was a novel experience. The stairs were especially distracting as the plug shifted even more when she stepped up. During the break, the main topic of conversation was the plugs. Most of the girls seemed to be in about the same place that Diana was, with it being a new and intriguing sensation. There were some girls that it was really uncomfortable for, but at least one of those turned out to be a girl who forgot to use lube. At the other extreme were the girls who loved the feeling of having their asses filled. One girl even admitted to cumming from just putting the plug in.

The class reconvened and the next instructor announced the next topic would be oral sex.

"I know that you all had an intro to the topic last night, and some of you showed more natural talent than others, there are basic skills and techniques that you are expected to master. As far as I'm concerned, the best way to learn is to practice, so after we learn each skill you will find a new partner and switch off trying it on each other."

What followed was an oddly dry and clinical explanation of how to start off a blowjob, followed by an awkward flurry of activity as the girls paired off and tried to figure out who was first. Diane found herself dropping to her knees before a dark-skinned girl named Lacy. As she knelt she became very aware of the plug in her ass. She watched as the girl standing over her took off her skirt, revealing long dark legs. The cock she pulled out of her panties was much larger than her own. She was both intimidated and excited by the sight of it. Looking up at Lacy who seemed to quiver with anticipation, she got to work. She reached out and gently wrapped a hand around the base of Lacy's cock and leaned forward. The instructor had said that, assuming that the cock was already erect, to start with breathing on the head first before doing anything else. Diane thought that it was odd, but tried it out. The sigh Lacy gave in response told Diane that apparently, the instructor knew what he was talking about. The next step was to lick the tip gently, which she did, tasting Lacy's precum and getting a soft moan of encouragement.

"Remember that the goal at this point is not to make your partner cum, but if you do, roll with it. For now, I want you to practice swallowing if the opportunity arises."

Following the plan the instructor laid out, Diane gave the tip of Lacy's cock a gentle kiss before wrapping her lips around it and swirling her tongue. Lacy moaned with pleasure and Diane tasted more of her precum dripping into her mouth. She then pulled back and let go of the large erection. Settling back on her heels she looked up at the girl standing above her, with her rampant erection still on full display.

"How was that? Did I do ok?" Diane asked with a smile.

"I think that you did more than just ok," Lacy said with her eyes aflame with desire. "I wish that you didn't need to stop. That was incredible! I need a minute to calm down before we switch, or I'm not going to be able to put this away."

Diane nodded and got up. Looking around the room, the other girls seemed to be in similar situations. She watched as one girl lost control and her partner hurriedly tried to get her mouth over the squirting dick and only partially succeeded, ending up with about half on her face. In general, Diane noticed that the girls who had been wearing skirts had all taken them off, while that wearing dresses had split between holding them up and taking them off completely. She pulled her own skirt off and set it carefully on her chair.

"Ok. I'm ready," Lacy said after a few minutes. "It's hard to calm down with all of this going on around us."

She had finally managed to herself tucked back into her panties, but there was still a very noticeable bulge. Diane pulled out her own cock as Lacy knelt before her. There was something oddly exciting as she watched Lacy's chocolate-colored hand wrap around her pale erection. When Lacy's dark lips parted and she felt the hot breath on her mushroom head, she felt as if a jolt of electricity traveled down her cock and into her ass where the plug was.

"Oh god that feels much better than it should," she moaned, straining not to grab Lacy's head.

Lacy smiled up at her and with a wicked grin, licked at the pool of precum that was pouring out of Diane. Diane gasped which turned into a moan as the head of her dick was encapsulated by Lacy's warm mouth. It took all her willpower not to cum when Lacy started running her tongue around. Lacy pulled back with a POP and grinned as Diane groaned with disappointment.

Standing up, Lacy whispered in Diane's ear, "You taste delicious."

Diane shivered at the thought of filling Lacy's mouth with her cum. Her fantasy was interrupted as the instructor called them back to their places. It was awkward trying to sit with a raging erection sticking out, but she knew that tucking it away right then was impossible, and half of the pledges seemed to be in the same situation.

The class continued with the lesson after which Diane found herself paired up with a small, pale-skinned girl wearing a curly bright red wig who immediately dropped to her knees in front of Diane.

"I'm Stacey, by the way," the girl said, reaching for Diane's panties. "I've actually wanted to do this since I first saw you checking yourself out in the mirror last night."

Completely ignoring the lesson, Stacey inhaled Diane's erection, shoving at much of it into her mouth as she could at once. Diane felt her cock bump up against the back of Stacey's throat and moaned at the intense suction that girl was somehow applying.

"If you don't stop I'm going to cum," Diane whispered urgently as Stacey began bobbing up and down, lips locked tight around Diane's shaft.

Diane's plea only seemed to encourage the girl. It was only a few more strokes before Diane lost it. With a stifled yell, she felt her balls start to boil over. As they did, she felt her ass clamp down on the plug, which sent another wave of pleasure crashing through her body as she exploded in the redhead's mouth. She grabbed hold of Stacey's head to keep her balance. Stacey made sounds of delight as she eagerly drank Diane's cum. Diane shuddered with pleasure as Stacey milked the last few drops of her cum out with her mouth and tongue. She gently stroked the red hair that she was holding onto. It was only then that she realized that it wasn't a wig.

"That wasn't what we were supposed to be doing," Diane whispered while trying to catch her breath, leaning against her chair.

"I know," Stacey said with a contented smile, still looking up at Diane from her knees. "But trust me, I already know how to suck cock. What I didn't know was how good you taste, so I wanted to learn that. By the way, the answer is delicious. And you look even more beautiful when you cum. Especially from this angle."

Diane ducked her head and blushed. She took another minute to recompose herself before looking at Stacey again.

"Are you going to stay on your knees all day or are you going to get up so that I can practice like we are supposed to be doing?" She asked.

"I'd be happy to stay on my knees all day for you, but if I'm honest, the thought of those lips around me is also really tempting. If you really want to practice, we can, but from what I have seen, you do a great job."

Stacey quickly reached out and pulled Diane towards her, giving her dick another quick suck before standing up.

"I know that I'm not big," she said as Diane dropped to her knees. "But at far as I'm concerned, that means that it's easier to hide in panties and fits into tight places better."

"So, I take it you have experience with all of this?" Diane asked as she reached for the black panties and what was hidden inside.

"You can say that," Stacey said with a laugh.

"It's beautiful," Diane said as she exposed Stacey's cock.

It was small. Maybe four inches when fully erect, as it was now. But it was perfectly smooth, without a hint of hair or stubble, and it was what she did only describe as perfectly shaped, if in miniature.

"That's sweet of you to say. But I saw you with that monster in your mouth before."

"Size isn't always everything. Besides, with yours I can do this," she responded and in one move, took Stacey's entire length into her mouth.

"Ohhhhh," the girl moaned as Diane licked all around her length. "I told you that you don't need to worry about practicing beginner moves."

Diane focused on returning the favor to the sweet redhead. With her lips locked around the base of her shaft, Diane alternated licking and sucking Stacey's entire length. It didn't take long before she was rewarded with a burst of cum in her mouth. It was a smaller load than any of the ones she had taken the night before, but that just made it easier to drink down. Looking up at her, Diane was amazed at how incredible Stacey looked while cumming. She was about to say something when their instructor called them all back to their places.

By the time they got to the end of the lesson, Diane had gone down on ten more cocks. Two of those had filled her mouth with cum, while another had exploded all over her face. Not that she blamed the girl, it had been part of the lesson plan. She had done the same in return. Despite her best efforts, another of the girls had also managed to push her over the edge while practicing on her. When the instructor finally called a halt, she was relieved. By this point, her jaw was a bit sore.

"Before I let you girls go to dinner, you have one last task. In your desks, you will find the next size plug. Take out the ones you are wearing and put the new ones in. After that, you are free to get dressed, make yourselves presentable, and go eat."

Diane opened her desk and pulled out the small black object that was waiting for her. Looking at it, where the one currently in her ass was about the size of her finger, this one was both longer and thicker, but not scarily so. It was actually about the size of Stacey's penis. Lifting a leg up into her chair, she leaned forward and reached back. She moaned softly as she pulled the small plug out of her ass and then sighed as it slid out of her. Her ass felt strangely empty, but she knew that the feeling wouldn't last long. The room was filled with moans and soft grunts of pleasure and stretching as the pledges exchanged their plugs for larger ones. Diane groaned as the larger plug stretched her ass open even wider as she slowly worked inside of her ass. She let out a sigh of relief as her asshole finally settled around the base of the plug. She could feel it deep inside of her, and even more than the smaller one, every time she moved.

Diane got dressed again and after wiping her face clean with a damp cloth, redid her makeup. The walk to dinner was very intense, with every step putting pressure on a different place deep in her ass. If not for the fact that she had already cum three times that afternoon, she was pretty sure that the walk would have had her on the edge, if not over it, which in and of itself was an odd thought for her. Dinner was nice and a good chance to talk to both the other pledges and some of the older students as well. She found that she really liked Stacey and that they had a lot of classes together.

After dinner, the pledges were gathered again, and a box was passed around.

"As mentioned before, the plugs currently in your asses are training plugs. They are there to get you ready to be fucked. But you girls are done with training for tonight. That doesn't mean you can switch persona, which you are supposed to be in until you graduate this course, it just means that you're free for the evening. As such, you should get changed. Whether you decide on comfortable or sexy is up to you, but either way, every girl should wear jewelry. In the box is yours. I expect them to be worn during the course unless otherwise instructed."

Looking in the box when it got to her, Diane saw that it was full of small metal plugs with a jewel on the base of each in various colors. After debating for a moment, she pulled out one with a dark green jewel. She noted that while it was shorter than the plug currently in her ass, it was about as wide around at the widest point, and it was much heavier. She headed back to the classroom to change plugs before trying to decide what to wear. Back at her desk, she couldn't help but groan as she pulled the long plug out of her ass. Unable to resist, she slid the black silicon toy in and out a few times, imagining that it was Stacey's little cock filling her hole. After a few thrusts, she managed to stop herself and replaced the long plug with the jeweled one. It felt completely different inside of her, not filling her nearly as much, but the weight made its shifting inside of her much more intense.