Big U Pride Ch. 05: Pledge Week

Story Info
The Cheerbois take on HellWeek, and Brit makes a big choice.
66.8k words
4.89
30.1k
46

Part 5 of the 9 part series

Updated 06/10/2023
Created 05/11/2020
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Thank you and sorry to all my fans for waiting so long for this chapter! I had so many thoughts, and so many fans emailed me with their wonderful suggestions. It's probably the most important chapter and I wanted it to be special so it took me forever to write. You'll notice it's much longer than the rest - I just couldn't keep anything out. It had to have the proper escalation, the right pacing.

If you haven't read the other chapters, please do! This won't make sense without doing so.

As always, I WANT TO HEAR FROM YOU! Please leave comments, or even better EMAIL ME!!!

But for now, please enjoy.

* * * * *

'Twas the night before Christmas, when all through the Beta House

Not a sissy was stirring, not even a mouse;

The garters were hung by the chimney with care,

In hopes that St. Dick soon would be there;

The sissies were snuggled all snug in their beds,

While visions of cum-filled balls danced in their heads...

The windows were fogged up, icicles decorating the windowsills as the holiday lights flickered around the house. The Beta House had some of the best decorations on the Big U campus, with bright lights, snowmen outside and a blow-up Santa outside on the lawn. Every house on the street was done up, but the Beta House drew everyone's eyes to it.

A passerby may have been able to make out movement inside as the Kappa House girls were busy arranging the main room. If that passerby peeked inside further, they would have seen those girls setting up elaborate red and green streamers and arranging the furniture.

When the clock struck midnight, a line of people had formed outside the door to the Beta House. The sight was unusual for the campus, though. It wasn't weird that there was a line outside the Beta House - oftentimes this House would be the site of exclusive parties. No, this was unusual because all the people in line were older men, mostly in their 40s. A passerby would have questioned why a line of middle-aged men was forming on the college campus to get into the Beta House.

In fact, they would have also noticed that some of the men were famous in their own right. They may have noticed that the Mayor was among the men in the line. Others were powerful lawyers, sports agents, and wealthy scions of prominent families. This was the creme-de-la-creme of society, with most of these men running major industries and business in the the big city. They were all built too, having once played sports at Big U when they were all in college.

Suddenly the door opened and light streamed out. There stood a Kappa girl, Lana, who ushered these men inside and helped them with their jackets.

Inside the house, the men were guided by other Kappa girls to the main room, which looked sumptuously decorated with holiday spirit. The Kappa girls brought out cocktails for these men, handing them out while helping them get comfortable.

Soon, the sounds of lively conversation filled the air as the men took seats in large leather chairs at a good distance facing the fireplace which crackled with fiery embers. The Kappa girls, dressed in short red dresses with festive mistletoe in their hair, were sitting on the armchairs, making flirtatious quips with the men. These girls, so ambitious, were making the connections in high society to get themselves the powerful careers they all desired after graduation.

*Clink, Clink, Clink

The head Kappa girl, Lana, tapped the side of her glass. The room quieted.

"Ladies and gentlemen, welcome one and all too Big U....or should I say to our distinguished guests, welcome BACK to Big U."

The crowd clapped politely.

"It brings me such joy to be able to have you here for our Annual Kappa Christmas Party. Each year the university recognizes that this is one of the highlights of the holiday season for renowned alumni like yourselves. We are delighted to get to host you again this year."

Lana continued. "A toast to Big U., and may this year see the return of the Football Championship Trophy."

"Here hear!" Shouted one of the men. They all drank to that.

"As you all know, the University has selected you to join us tonight because you are not only beloved alums, and not simply some of the most influential and powerful men who have graduated from here, but more so because each of you has made a sizable donation to the university this year."

"You each have given back to the University. Mr. Mayor, for example - "

The men looked at the dashing politician, his hair perfectly coiffed and suit bespoke.

"The University is so grateful for you single-handedly moving along the permits to get the new athletic facilities built. Without them, we wouldn't have been able to recruit our star athletes this year. And speaking of which, Donte West here has used his sports agency to help convince top picks to come to Big U to play. The University thanks you both and all of you for this sort of generosity."

Lana took a sip from her drink. "And such generosity should not go unrewarded."

She backed up and leaned on the fireplace mantle. The flames cast the room in sharp shades of dark and light. It reflected off the Christmas tree in the corner of the room, off of which hung ornaments shaped like buttplugs and nipple rings.

"So not only will such generosity be rewarded with the company of us young, supple and thankful Kappa girls..." as she said that, she could see the men wrap their arms around the girls sitting on the arms of their chairs, some being quite brave with their hand placements.

"But something else just as special, something that only Big U. can provide. And I know all of you have been waiting all year to get this opportunity."

Some of the men grunted in approval, knocking back their liquor as their excitement grew. They knew what was ahead of them this night, with most of the men having come to these yearly holiday celebrations for several years.

"That's right, the latest batch has been selected and trained and is ready for use. And I must say, this is probably the finest class that I've had the pleasure of training in my time here at Big U." Lana said. "I know you will find them up to the task."

"So without ado," Lana said, her smile wide. "It is my pleasure to present to you, this year's Big U. Cheerbois!"

As she said that, Kelsey stood and opened the backdoor to the main room.

The men and Kappas watched as one-by-one, the sissy Cheerbois, dressed in alternating red and green skimpy elf outfits, crawled out. Jada led the way, her big ass filling out the red miniskirt as she crawled lustily forward, with Kagney behind her practically rubbing her nose in between Jada's asscheeks. A red ribbon connected each sissiy, tied in a bow around Jada's mid-riff and tied to each sissy in turn.

I followed Candi in, crawling behind her in the long line of sissy bodies, exaggerating our moves so our asses wiggled in the air as we coordinated movements. It had taken a week of practice to get this right, and we made it look easy as we crawled to the center of the room in front of Lana.

"Rise, gurls." Lana said. We tried our best to rise steadily to our feet in unison, getting our bearings as our heels clicked against the hardwood floors.

The men took in the sight in front of them. Six young sissies in their prime, decked out in alternating green and red braziers and mini skirts with knee-high green and white striped stockings and heads topped with elf-hats, made to look like Santa's slutty helpers. I looked into each of their faces, seeing that recognizable look in each of their eyes.

Lust.

"Aren't they something? Groomed to perfection, and still they have so much further to go in their sissy journeys. But we present them to you today, the products of our work and their dedication."

One of the men brazenly was rubbing his crotch as he stared at us. I should have felt ashamed or disgusted, but instead I felt that undeniable feeling that I knew my fellow Cheerbois shared.

Pride.

If it hadn't shrunk over the past few months, the men would have been able to see my sissyclit standing at attention. But it barely made a dent in my skirt.

I looked to my side and could see Jada beaming, licking her lips as she looked back at that men who rubbed himself. She looked so hot, and was wearing the same red color outfit as I was. Around her neck was the same choker that I wore.

It read in shimmering rhinestones, "HO HO HO". I loved it. She also wore the same long striped thigh-high socks that I did, making her shapely legs stand out. I hoped they had the same effect on me.

"We have taken you away on Christmas Eve, away from your jobs, massive responsibilities, and for some of you your families. All so we can show you our gratitude for all you do for Big U. Our Cheerbois are dying to show you how thankful they are. Aren't you, gurls?"

"Yes Mistress." We all said at once, our voices soft and innocent and high-pitched. The high doses of hormones had done wonders not only on our bodies but also our voices.

"And I know you gentlemen would love to try each of them tonight, but alas we don't have the time. So instead, we wanted to do this in holiday style."

Lana grabbed the stockings that were hanging off the mantle. She walked up the men seated on the couch and handed them out one by one.

"We have in each of these stockings the name of the sissy Cheerboi that you will get to spend this magical Christmas Eve night with. And of course we had to write it in the most sissy of ways."

She went back the first man who she gave the stocking to. "Would you like to do the honors and start us off, Donte?"

He smiled, "It'd be my honor, Lana." The man, whose muscles were nearly popping out of his suit, reached into the stocking. He grinned as he grabbed on to something in there and started pulling it out and showed the group.

In his hand was a silver buttplug with a paper tag tied around the base. He read it, "Candi."

Candi, standing there looking cute in red, smiled and batted his lashes at the man.

Each man went now, pulling out silver buttplug after plug each with the name of their sissy.

The Mayor reached into his stuffing and pulled out the plug. He read aloud from the pink name tag, "Britney."

I knew my manners so I crossed my legs innocently and winked at him while I smiled, my lip gloss shining in the firelight. He was a burly powerful man, wearing a custom suit and showed off his cut features. He had been a star quarterback back when he was at Big U and he clearly hadn't let his body go. Some said that he could be Governor some day, maybe President. But others said rumors that he liked the company of escorts would eventually crash his career. But the rumors didn't stop him from amassing power and wealth.

After all the men had opened their stockings, Lana spoke up again.

"They're all yours, gentlemen, to do with as you wish." Lana grabbed a pair of scissors and cut the ribbon that bound us together. "Sissies, why don't you show these men your rooms."

As she cut the ribbon by me she said, "Make me proud, Brit."

We each walked up to our assigned men and stood over them in our heels and slutty elf outfits. I reached out my hand and the Mayor grabbed it in his large hand and stood up, towering over me. I led him down the hall to my room before shutting the door behind us.

"Well, well, well. I've definitely taken my fair share of Big U Cheerbois in this room. But none looked as fine as you do, Britney."

I blushed, he really knew how to work a room. I guess that made sense, him being a politician and all.

"Thank you, sir. I'm honored to get to spend this night with you." I said.

"I bet you are, I bet you are." He said. He sipped from his whiskey as he looked around my room, taking in the pink decor and mirrors all around.

He looked up at one of my inspirational posters. It was a drawing of a sexy redhead in a sexy lingerie version of the Uncle Sam outfit, as she pointed and looked serious. Mr. Mayor read it out loud, "Do your duty...Serve Alphas!"

He turned around and looked at me, "Is that what you believe your duty is?"

"Yes, Sir." I replied. "This is what I was always meant to do, it's why I'm so happy on the Cheerbois. I live to serve Alphas like you. It's what I was built to do."

"Wow, such conviction. It's always inspiring to see young people like yourself have such commitment. I could use someone like you in City Hall."

"Oh?" I said. "That sounds so tough! I don't know if I'm smart enough for that kind of political work."

"Oh no, no." he said. "Not for the politicking. I just think the boys in the office could use a good...Sissy Suckretary." He said. "Let some steam off."

"Oh!" I replied. "I would happily serve you there!"

"Good, good." He sat down on my bed and put his drink down. "Come, sit down on my lap."

I tiptoed slowly over to him, looking demure. When I got to him, I sat down on his outstretched knee. I could easily feel his bulge rubbing against my pert butt.

I giggled and sashayed over to his waiting lap and sat down. I immediately felt his growing erection underneath my panties and I giggled and squirmed on his lap. Men like that!

"So, little Sissy Britney. I know this night is about me, but tis' the season. I want to hear from you."

He bounced his knee up and down, my body popping up and down with it. It was weirdly comforting.

"Come now, tell Santa...have you been a good gurl this year?"

I thought about that question and answered honestly. "No, Santa. I haven't. I've been very naughty this year."

"Oh yeah?" He said. "How so?"

"Well," I said, acting like a kid sitting on a mall Santa's lap. "I've started to wear really skimpy clothes to get the attention of Alpha men. I think that's very naughty."

"And why do you do that, little sissy?" He said.

"Mistress Lana tells me that the best way to get the attention of strong men is the show off your assets."

"Mistress Lana is a very smart woman. Tell me then, why do you want to get the attention of men?"

I was getting into this game he was playing. I enjoyed being the diminutive one, being wrapped up in the arms of a big man, bouncing on his leg and acting all cute and silly. It felt so freeing to get to be this way. My mind was all light and breezy. And that wasn't just from the poppers I had inhaled earlier in the evening.

"Why get the attention of men, Santa?" I repeated his question. "So that they let you play with their big cocks, of course!"

He gave a hearty laugh, actually sounding like Santa there.

"You really have been naughty, SIssy Britney."

"Yes, sir, I really have."

"The Mistresses told me how naughty you can be. Do you know what naughty sissies like you get for acting that way?"

"No, Mr. Santa, what do they get?"

"A. good. hard. spanking." And with that he bent be over his knee and starting slapping my ass with his big hand.

"Oh Santa!" I squeaked as he spanked me. His spanks were firm and strong, and my ass rippled each time. They stung, but I liked the feeling of being shown my place!

He stopped and let me recover. I sat up again on his knee.

He bounced me on his knee again and rubbed his hands all over my ass and hips. I looked back and could see his handprints on my ass.

"Now little sissy, tell Santa what you want for Christmas this year."

I looked back at him and bit my thumb sexily, pretending like I was thinking really hard about it. I slowly grind my hips against him as I did.

"Ummmmm...are you sure you won't judge me if I tell you, Santa?" I asked playfully.

"Santa would never judge you for telling the truth."

"In that case." I said. "What I really want for Christmas is...a big fat Daddy dick to fuck me hard in my boipussy!"

"Ho Ho Ho!" Mr. Mayor chortled. "Well then! You know what, sissy?"

"Yes, Santa?" I said, looking at him innocently, waiting for my answer.

"You're in luck, because I think Santa brought that in his big sack here." He said, pointing to his pants.

"Oh hurray!" I said, shimmying my hips.

"But first, show Santa what's under your Christmas tree." He pointed to my skirt.

I stood up and looked at him, lust burning in my eyes. I put my thumbs on each side of my skirt and slowly pulled them down before standing up. I stood there, facing this powerful man, my skirt at my feet as he looked at my sissyclit tied up in a green bow. I bit my thumb again, twirling from side to side as he gazed at me.

"Fucking perfect." He said, looking at it. "Can you believe you used to think you were a man? With this thing?"

I blushed, knowing how right he was. It was unbelievable, to think that I could ever have thought I'd be a man. Pretending to act like a tough guy, trying to hang with the real men. I came to this campus thinking I'd be king of the campus, but just look at where I'd found myself. With a powerful older man playing with my tiny little member as I gazed lustily into his eyes, ready to do anything he asked.

"But you're not a man, are you little Brit, are you?" He said as he twirled my sissyclit between his fingers making bursts of lightning pleasure shoot through me.

"No, sir, no..." I said, trying to catch my breath as he toyed with me.

"What are you, then? Because you ain't a girl neither." He said, starting to tickle my little gem sack too.

"I'm..." I was breathing quickly as he played with my bits. God, he knew how to get me going. "I'm a...."

"You're a what?" He was stringing me along, taking me to my subspace. The place that all sissies know intimately, that mindfucked state that draws us in, pulls us to its center and surrounds us in its jelly-like cocoon.

"I'm a s..." he squeezed the tip of my sissyclit, making me shiver and moan.

"I can't understand, Brit. What. are. you.?" He said, punctuating each word. His words authoritative. His voice confident.

"I'M A SISSY" I shouted suddenly as he squeezed me again.

"And a mighty fine one too." He said, agreeing. He stopped his handiwork, letting go of me weenie.

"And what makes you a sissy?"

I knew the answer to this question so well. It had been so important, it's what got me here, what gave me ultimate certainty about the decision I had made earlier this year. It was something I would have to live with, but something I was so proud of.

"Sir...I am a sissy because I was put on this Earth to serve Alpha men like you. I am built to please you, I am trained to meet your needs, and I will stop at nothing to do so."

"Go on..." he said, rubbing my ass with his large hands.

"I live to bring pleasure into this world, to make sure that those powerful Alphas like yourself are always relieved of stress, and that you know that you are thanked for being Alphas."

"And what do you use to bring pleasure into this world?" He asked me, squeezing the round porcelain-skin globes of my ass.

"Everything, my whole body, my whole spirit, my whole soul."

I moaned quietly, feeling him grope me. The feeling of being desired was intoxicating. I was practically drunk on the lust he was feeding me.

"I bring pleasure with...with my holes, sir."

"Mmmmm, yes. And, tell me, who owns your holes tonight?"

I didn't even hesitate. "You do. You own my holes."

"You own my holes, what?" He prompted me.

I remembered my manners. "You own my holes, Daddy."

"That's better."

He squeezed my asscheeks once more and let go.

"Santa thinks you really have been naughty. But this Santa actually likes his sissies naughty. In fact, he thinks the naughtier they are, the more they deserve nice big presents."

"Oh yeah, Santa?" I said, smiling back at him and squirming on his lap, wiggling my ass on his knee.

"Oh yes. But first, Santa needs his milk and cookies."

"Whatever do you mean, Santa?" I asked him, biting my lip. His cock was rock hard in his pants. "I didn't make you any cookies, I'm so sorry!"