Big U Pride Ch. 05: Pledge Week

I was dumbfounded. Was there any doubt left in her? Where was the old Kris?

"The problem is that that's kind of gay. And like, demeaning."

Krissy looked both confused and upset with me. "Wait, what happened? How many times have we celebrated getting the attention of men? How many times have we enjoyed sucking cock? I don't get it. One minute you're a turbo slut who loves this life, and the next minute you're this...other person. It's like you're..."

"I'm what?" I said, challenging her. I wanted to hear my best friend say it.

"Like you're Brian."

"Well, aren't I?"

"I remember Brian. I remember that guy I met the first day here at Big U. I remember that sad sap who would rather play video games than go live life. I remember that boy who never did anything exciting. I remember that wallflower who wanted to go to parties but didn't know what to do when he was there."

"What are you saying...Kris?"

"Don't call me that."

"Don't call you what? Kris? Well that's your real name."

"I don't want anyone calling me that again."

"What are you talking about? How could you throw away your life like that?"

"Throw away my life?" Krissy said to me, her voice raising. It was incredible, the voice of the old Kris was gone, replaced by the high-pitched squeals of a real feminine person.

"What life?" Krissy said. "That boring old life where I was a loser in high school and bound to be a loser in college and for the rest of my life? A life where I was going to get some boring desk job and just live the rest of my life as the sad sack that everyone felt bad for but never wanted to spend time with?"

"You don't know that for sure."

"Well I don't have a trust fund waiting for me like you do." Krissy shot back. "And even if I did, what would it matter if I was still at heart just a loser!?"

"Is that what you think I am? A loser?"

"Brian was, but not Britney!" She shot back.

"What are you saying?" I demanded to know.

"I'm saying that the Kappa girls gave us this golden opportunity. Say goodbye to our old lives, say goodbye to that boring future we were bound for. Instead, it's replaced with one where we are gorgeous, we are popular, we are practically famous."

"Famous for being sluts." I retorted.

"Yes! Good! I'm sorry, but what is your obsession with this? You can't tell me it isn't fun to get catcalled, to get objectified for being hot. You can't tell me that it feels good when your body gets a man's cock hard. You can't tell me that it isn't the thrill of a lifetime to have a pulsing cock inside your mouth, the man moaning because you're the sexiest thing he's every been with."

"BUT THAT'S GAY!" I practically screamed.

"Not when you look like this!" Krissy said, standing up on the bed over me.

I had to admit, this was the most feminine creature I'd ever seen. The babydoll, the panties, the pigtails...the soft skin, the budding breasts, the makeup and soft facial features. If I tried, I could see the Kris underneath. But instead, all I saw was Krissy...sissy Krissy.

"The Kappa girls have explained it over and over, and yet you still don't get it. We're different, we're special."

Krissy then spelled it out for me, punctuating every word, "We. Are. Sissies."

Something about that word...it tapped into a well deep inside me, one that I would let spring forth from time to time, but now I felt like I had to suppress.

"I know." I whispered.

"What's that?"

"I said I know. I just...it's not easy coming to terms with this. What will everyone back home think of me?"

"So what? Let them think what they think." Krissy reassured me. "What matters is that you get to live this new life, this new life full of fun, full of pleasure. Just think about all the important people we get to be with, all the men who will adore us, all the girls that will be jealous of us. This is the chance of a lifetime and I am sure as hell not going to miss my opportunity."

"I know you won't."

"And you shouldn't! I want you there right by my side. Don't forget, you're the one that got ME into this first!"

Krissy was right. After Lana had hooked me, Kris was the next to go.

"Plus," Krissy said. "I want no one else next to me when I'm sucking cock!"

I laughed at the joke, remembering our night with Mr. Hammerwood.

"Well, I can't just let you hog it all to yourself." I joked back.

"There's the Britney I love!" Krissy smiled. "That's the thing with you, Brit. When you're all alone, all your doubts just creep to the fore. You become that old soul that no one wanted around. But put a cock in front fo you, and BAM!"

Krissy clapped her hands.

"It's like you become a sissy pornstar! Like, you remember how much fun it is to be a slut. You become this pleasure machine, capable of great things...I just wish we could see that side of you all the time."

Krissy had a point. I had a way of getting lost in cock, of relishing in the attention of a man. It was in this moments that I became this other person, this queen of pleasure.

"I know...I'll try, I will. But this is a big day and I have a lot of things to think about." I said.

"I know," Krissy said, hugging me. "I'm here for you, always." She gave me a kiss on the lips, letting her lips linger as we breathed each other in.

Our phones then dinged.

"This is it," Krissy said, breaking our kiss. "The last challenge."

The message on our Cheerboi Apps said, "Check outside your doors for today's outfit. Hair must be in either pigtails or bob. Makeup must be 'Glam' style, with winged liner and accentuated lashes. Lipstick must be glossy red. Bring lipstick with you."

Krissy practically squealed in excitement and raced out the door to go find her package. Meanwhile, I collected myself, still recovering from her embrace, and got off the bed and checked outside my door. There was a carefully wrapped box with a bow on it. I brought it inside my room and opened it on my bed.

Inside was a pair of orange boyshorts and a white tank-top that read "Femboi Hooters". In another time I would have thought that this was the most embarrassing outfit to wear. But somehow, at that moment in time, I just thought about how the shorts would show off my nice ass.

There was also a pair of white athletic tube socks and white sneakers. Without time to waste, I got my day started, first with a trip to the showers, my enema and a total body shave. The Kappa girls had taken us for laser hair removal the other day too, so there was barely any hair to remove.

I first put on the bra and skimpy thong that were included in the box, then threw on the tank top and pulled up the boy shorts. They were tight and huge my ass perfectly, with the bottom of my cheeks squeezing out the bottoms, revealed to the world. The bra under the tank top made it look like I had larger breasts than the budding A-cup boobs that I now sported. I tucked the shirt into my shorts and then sat down to pull my socks up. After putting on my shoes I went to work on my makeup.

Over the past few weeks, this part had started to feel more and more natural, almost necessary. I kind of enjoyed the ritual of sitting down to put make up on. It was like I was putting on my brave face, like I was putting on the face that would take on the world outside. This was a mask, in a way. It was a way of covering up any imperfection...perhaps a way of covering up the doubt, the residual 'Brian' still inside. When I put it on, I could be Britney, I could handle the Kappa challenges.

Plus, it made me look like a super hot girl. That made me feel confident, it made me feel special. The same happened with putting on lingerie or girly costumes, it just made me feel like I was somebody important. The thong I was wearing rubbed me in a way that reminded me that I was doing something exciting. Dressing up was like wearing armor, it gave me the courage to do the impossible. And yes, it brought Britney to the fore. Brian was a wimp, but Britney was a queen.

Lacing up my sneakers, I then stood up and admired myself in the mirror. There I was, the perfect slutty Hooters waitress.

I smiled and waived at the mirror, pretending like I was some bimbo about to take a man's order at a real Hooter's. It was unbelievable how believable I looked. Apart from the "Femboi" part on the shirt, anyone would have believed I really worked at Hooters. Well, maybe I needed bigger tits.

So this was it, the last challenge of HellWeek. Was I ready for this? More importantly, would I be able to handle not being a part of the Beta House, being a Cheerboi? Could I imagine a life here at Big U. where I wasn't part of this? I struggled with that thought as much as I struggled with the thought of continuing down this path, of becoming a full femme Cheerboi, of letting men play with my body.

I took a deep breath before joining the group downstairs. All the Cheerbois were dressed in the same outfit. Jada stood out amongst us because she had folded up her shorts so her bare ass was showing more from under them. No surprises there, always a show-off that one.

Kappa girl Lacey was there greet us.

"So, moment of truth everyone, the last challenge of HellWeek. First, let me tell you how proud of you all that I am. You've all made amazing strides to get to this point and we are so thrilled. But, of course, you still have to make it through tonight to stay a member of the Cheerbois."

She inspected all of us, one by one.

"These outfits all look so perfect on you all. Jada, let me just say that you were made to wear this."

"If you've got it, flaunt it right?" Jada said playfully.

"And you do got it. That is an ass that any girl should be jealous of." Lacey spanked Jada's ass and we all watched it jiggle. It was mystifying.

"So today is a big event for us, it's our fall Kappa Fundraiser, and there are lots of special guests today. Many of them are major donors to the school, and we will also have our major athletes there too."

She continued her explanation, "And you all have a special role to play. You see, the special guest this year is Dirk Diamond."

We all knew that name. Dirk Diamond was one of the wealthiest alumni of Big U. He was the founder and CEO of a famous cruiseship line named "Titillating Trips." The cruises were aimed at young horny men, since the tours were staffed by large-breasted women. They would mostly go around the Caribbean and stop at each of the big party sites over the summer. It was rumored that there would be orgies on those cruise ships, but there was a strict "What happens on the boat, stays on the boat" mentality, so there was never any photo evidence of them.

Dirk himself was known to galavant around with Playboy models and Sports Illustrated models. He was a renowned horndog, always with a new girl on his arm every week. He was often seen on his yacht, the "CockFighter", docked in New York or Los Angeles with models on tow.

But he was best known for being the college party guy back when he was a student at Big U. He was like a Van Wilder figure, always playing pranks on the college president and professors. His most famous event was something called "Wings and Breasts" night where all the frats would judge chicken wings made by girls from each sorority. The catch was that the girls would be in the skimpiest bikinis and the night would end with a competition judging who had the best rack. That was the last straw, and the college leaders threatened to kick him out because a bunch of feminists had caught wind off the event and threatened to cut their funding. But what they didn't know was that his raunchy charity events brought in more money than those critics. So they turned a blind eye to him.

Since then he had become one of Big U's biggest supporters and would be at practically every football game up in one of the VIP boxes with some hot date, along with some adoring Big U students.

Lacey said, "So to honor Dirk, we are making the theme Wings & Breasts Night, and what better way to do it than with some Hooters waitresses! That's where you all come in!"

So that was the final challenge? Just to serve a bunch of men some wings and beers?

"Sounds simple enough. But just know that we have built in some, shall we say extra challenges in the night. I won't spoil the surprise, but just know that these are some of the most important men for Big U., and we expect you all to treat them right. We don't want to hear any criticisms. If any of them tell us that you have been anything less than perfectly accommodating, then you can expect not just to be kicked out of the Cheerbois, but for us to make your life miserable. That means releasing your sissy pics to your friends and family, and all over the internet. You'll never get a job or a life again."

I gulped. They meant business. Every now and then the Mistresses would show that they had a dark side to them. It reminded us that they did have control over us.

"So, time's a wasting. Let's all head go!"

She led us out to a line of golf carts awaiting for us. They were each driven by the other Kappa girls who were wearing fancy ball gowns. We walked over and got into them, noticing that walking using the sneakers was so much easier than heels. Though I did miss how the heels made me feel tall and powerful.

I thought we were going to the Kappa House, but the carts took a sharp right and kept going. We headed down the street, with the eyes of ogling men on us as we drove.

I noticed the mansion we were pulling in to. It was the Dean's House. The carts drove over the gravel pathway, past several fancy luxury cars. I noticed a Lamborghini in the mix. Could that be Dirk's?

We could hear the sounds of classical music from inside and see people mingling on the lawn as we pulled up. It was a collection of men all in their Sunday finest, sipping on cocktails and champagne and chatting, probably about big transactions and business deals.

The girls ushered us into the carriage house next to the mansion and parked the golf carts. We all got out and before we left the carriage house the Kappa girls gave us strict instructions.

Lana spoke to us, "So, you will be divided into pairs again, and each pair will rotate jobs. First, Candi and Jada will start with bar service, Bambi you and Kagney will start with restroom service, and finally Britney you and Krissy will start on the wait service."

Seemed simple enough, just like the summer job I had one time working for a catering company. I learned how to make drinks and could carry a tray easily. I guess they were just trying to get us used to doing work for free?

We followed the Kappa girls into the house, feeling out of place in our Hooters outfits while walking in this mansion, the with the fancy lights and chandeliers. But we just did as we were told and followed.

The Kappa girls entered a big hall room and we followed behind and saw that it was filled with the party guests, these major donors and powerful university people. They were all dressed in tuxes. With the Kappa girls in their ball gowns, and these men in their tuxes, I definitely felt stupid wearing this Hooters getup.

The conversations in the rooms all went silent as we entered the room.

"Gentlemen!" Lana said. "I'm so glad you could join us for today's festivities!"

The men clapped as the Kappas stood side by side. "As you know, the fall Kappa fundraiser is one of the jewels of the charity season, and we know your donations will all go to support this university. Go Big U!"

The audience chimed in with, "Go Big U!"

"And we are honored to have our honored guest here today, the one and only Dirk Diamond."

A man stepped up from the crowd. "Here, here!" He said, lifting his drink. The men all raised their glasses in turn.

He was middle-aged, maybe mid-40s. He was handsome in an average-Joe kind of way. There was something so...playful, about his energy. Playful, yet powerful. He had an undeniable presence in the room. For some reason I couldn't stop staring at him. It had a magnetic pull, his aura.

"And," Lana announced. "In honor of our Dirk, we've decided to set our theme tonight off one of his beloved legacies here. Wings and Breasts night!"

Dirk shouted, "Well alright then! Maybe next time we can do a Wet T-Shirt Contest too!"

Everyone laughed at Dirk.

"Maybe, maybe," Lana said. "But how about we introduced you gentlemen to the staff for this afternoon. Gurls?"

She gestured for us to come out from the room behind them. The men started hooting and hollering at us like we were some cheap hookers. I hate to admit it, but I liked the attention. We all gave them big smiles, knowing we were expected to give them a show. Maybe they were genuine too...

"Some of you may already be acquainted with this class, but for those that aren't - may I introduce this year's class of Big U. Cheerbois!"

I held my breath, feeling the eyes of all these men on me. I felt their eyes on my face, on my outfit, on my body. They were inspecting each of us with their eyes, reviewing us like we were merchandise. I felt objectified, I felt like the prize pig hit the county fair.

Then the men started clapping again. I didn't mind the objectification, it seemed, when it was accompanied by this approval. This approval from these important men. Approval from Alphas.

It gave us meaning.

"But you will all get acquainted with them intimately soon enough over this night and over the year. This is always a special time, when Big U.'s finest get to meet its new batch of Cheerbois. I'm sure you'll find this year's batch to me of the finest quality."

She let the men look at us all in a group one last time before ushering us away. She sent Bambi and Kagney to the restrooms for their first job, I guess to give hand towels like in fancy hotels. Candi and Jada were sent to the bar. Me and Krissy were then handed trays of food and drinks to start handing around.

We made our away about the crowd, looking completely out of place wearing these Hooters outfits. As I squeezed through groups of men, I felt hands squeezing my ass or on my chest. They didn't have any hesitation in groping me and Krissy, doing so at their will. I just kept smiling, knowing that was what I was supposed to do.

We handed out plates of wings and flute glasses of champagne, along with the spare beer here and there. This was just like that summer job I had catering - well of course with the exception of being dressed like a hot slutty girl and having men touch me in lewd ways. I tried to pretty myself up, posing all cute as men took plates off my tray. I had to play the part. I didn't want any complaints that led to me failing this challenge and getting kicked out of the Cheerbois.

We worked this job for the first hour of the night. In that time I recognized many of the men present at the party. At one point I felt a hand linger on my ass and a voice whisper in my ear.

"I recognize this ass." I turned around and saw who had said that. It was Professor Steele! From the other night at the Hidden Delights Club.

"Oh hello Professor, would you like a drink?" I said, offering him one of the champagne flutes.

"Yes I would in fact." He said, taking one of the drinks. "And I could drink you up too. Damn you look fine today."

I blushed. For some reason, I felt so...girly around him. He gave me a weird feeling inside. Maybe it was because it was older, or because he had this commanding presence. Something about him gave me the tingles inside.

"Well thank you, sir," I said. He put his hand back on my ass.

"I wouldn't mind a taste of you tonight."

What could he mean by that? "Oh...thank you, sir." I said again.

"But that will have to wait...but not for too long."

He let me go and I continued serving the other men. But his words rolled around in my head.

Lana and the rest of the Kappa girls were mingling with these men, clearly networking and making connections. Clearly this connection to the powerful elite was going to help their careers.