Big U Pride Ch. 05: Pledge Week

Had I made the biggest mistake of my life?

That's when I heard a knock at my door. "Sorry mom, gotta go!"

"I bet you have a girl over there, don't you! I wouldn't want to interrupt!" She said, before we hung up.

Lana waltzed in and hopped on the bed next to me.

"Hey Britney! Just wanted to check in on my favorite Cheerboi! I heard your show last night was incredible."

"Yeah, it was pretty crazy." I said.

"Professor Steele came up to me between classes today and said that you were a star! He's a really important person to know, so great job impressing him."

I thought about Professor Steele and the warm feeling that I got when I was around him. I got that feeling again. Why did that man make me feel that way?

"Yeah, he was...nice. It felt weird that he knew me from before all...this." I said, pointing at my new body and wardrobe.

"Oh yes, honey. But back then you were a nobody, forgettable. Now you are on the minds of every powerful man in the area thanks to your performance last night. One of them is probably jacking himself off thinking about you."

That stopped me in my tracks. I don't know why, but that just filled me with a perverse pride.

"But you still have a lot of work to do in your training. It's like the 10,000 hour rule - you have a lot more practice needed in your cock handling. But you're coming along really nicely!"

"Yeah, I don't know if I can keep doing that kind of stuff." I was honest with her. The dressing up, the dancing. I could come back from that. But if I became known as a cocksucker, then there's no way I could go home with that reputation hanging over me. The looks I'd get on the street if someone recognized me...

"Oh honey. I know. I know it feels weird sometimes. It's scary, to lose control of your body, to give it over completely to someone else. The feeling of shame that you sometimes get thinking of it. But you can't tell me that you didn't in your heart enjoy it. You liked the feeling of just letting go and living in a world of submission of pleasure."

She continued. "Plus you know you find gratification when those men approved of your work, when they thanked you for your service."

She was correct in a way. I had found a sense of purpose in sucking cock. It may have felt gay at times, but it was undeniably something that I kind of enjoyed.

"Plus you can't go back to not sucking cock, you need cum now."

Wait what?

"What are you talking about? I could stop if I wanted to."

"Sure you could. But I'm just talking science. Now that you had a taste, now that your body has finally matured into its sissy form, there's no going back. You have to understand, sissies like you have like, super super low testosterone. More than real girls, but barely."

She explained, "And your body thinks in a way that it needs more testosterone to feel like a man. But obviously no amount of T could do that. But your body craves it. So how do you get that testosterone? Through the cum of a dominant male, of course. Alpha cum has super high concentrations of testosterone, so obviously your body is attracted to it."

Stroking my leg, she looked at me intently. "But every time you swallow a load of cum, you become more sissified. It's a vicious cycle! The more sissy you are, the more testosterone your body wants, so the more cum you drink which makes you more sissy, and so on and so forth! You can't change that, it's your biology."

Was she telling me the truth? Was I stuck in this loop forever? Could I never change back?

"You're going to go through phases of denial, sure. But your instincts will always kick in. Think of it as like a 'fight or flight' instinct. But instead, you have a new sissy version of that, a 'fuck or suck' instinct. When your adrenaline is up, you'll feel that need to be submissive to an Alpha. Your biology will take over and your need for cum will overwhelm you. It's fine! Just embrace it, honey. Life's easier that way."

I had barely digested what she had told me when she pulled a shirt from her back pocket.

"But hey, I got you something!" She handed me a red shirt.

I unfurled it. The logo on the front was in the Coca Cola script, looking like their famous "Enjoy Coke" logo. But instead, it read, "Enjoy Cock"

"Isn't it soooo funny?" Lana said. "I knew you'd enjoy it."

She got up and went to the door, "But hurry up now, your next challenge is up!" She pressed something on her phone and my Cheerboi App dinged on my phone.

"This one is actually really fun!"

I looked at my phone for the challenge, "Pool party!" it read. My instructions were to wear a pink micro-bikini.

I found the exact outfit in my closet. I put on some makeup, finding myself more comfortable doing it every single day. The bikini top wrapped around my budding boobs. Not much to contain, but enough to look femme. The bottom somehow contained my sissyclit without much bulge at all, but I still tucked it down and back as I had been taught by the Kappas. The back of it was barely a string, sliding between my asscheeks.

This was the least amount of clothing I think that's legally defined as clothing, I thought.

I met the Cheerbois downstairs, everyone in different color bikinis, but all the same style. All the Kappa girls were downstairs and they complimented us on our outfits. They were wearing bikinis too, but theirs covered up more of their bodies. They looked absolutely stunning, like Sports Illustrated models.

Kelsey said, "Today's challenge is simple - the Big U Swim team house is having a pool party today, and you are all going to help them! It's simple, just look pretty, serve drinks and food, and get some sun. Easy, right?"

It actually did seem much easier than the previous challenges. Of course, the exception being that we'd be out in the open wearing these ridiculous bikinis in front of a bunch of guys on campus.

The girls escorted us to their cars and we drove in groups to the Swim Team house. When we rolled up, we could hear thumping beats and I saw the smoke from the grill spiral up in the air.

As we walked out to the back, I saw men in swim trunks, shirtless, lazing about in the pool or sipping beers while talking about sports or grilling.

"Ladies!" One yelled at all of us.

The Kappas greeted the Swim Team guys and started drinking and enjoying the party. Us Cheerbois kind of huddled around, feeling a bit exposed wearing these outfits around these new guys.

But one, by one, we were picked off as guys came up and offered to get each of us drinks. Krissy next to me was propositioned by a guy who asked her to serve drinks to the crowd.

So that's how we ended up bringing plates of food and beers to the guys and girls. Guys would sometimes give us a firm spank on the ass and tell us thank you after we handed them a beer. It was humiliating.

One guy came up to me, "Hey, the name's Jay." He took a beer from the tray I was holding.

"Oh hi." I said, timidly.

"You look like you're burning up in the sun. Come over to here, let me get you some sun tan lotion." He had a point, I would definitely burn if I didn't lotion up. I went over to the chair and sat down, and reached for the lotion.

"Don't bother, I got you gurl." He said, and grabbed it. He squirted some in his palm and began rubbing it along my bare shoulders, massaging me as he did.

I had to admit, it felt nice to be treated like this.

"Hey, why don't you lay down on the chair, it'll make this easier." I followed his instructions.

He rubbed lotion down my shoulders and down my back, lathering me up. I enjoyed the feeling of his hands on me. But then his hands went lower and he rubbed my asscheeks.

And I just let him. I didn't know what else to do. He squirted more lotion on his hands and rubbed my ass in circular motions, squeezing as he did. He went down each of my legs, lathering them up, but then returned to my ass.

His fingers got closer to the gap between my asscheeks. He massaged firmly, reminding me of his strength. I froze, not knowing how to tell him that I didn't want him feeling me up more. He gently spread apart my cheeks and he squeezed the bottle of lotion into the crack. He then proceeded to rub that lotion in more.

Then I felt it. His fingers rubbed around my asshole. My made circular motions with his fingers around the rim of my hole.

And I...I loved it. It tingled and the pressure was pleasurable in a new way I didn't recognize. I just let this strange man I had just met feel me up and play with my asshole.

The inklings of doubt still rose within me. But they were quelled by the surprise of feeling his thumb probe into my asshole.

That's right, a man had his finger in my ass. And I just let him. Why? Because it felt...so good. Like a pressure that was both uncomfortable and relaxing at the same time. It was the feeling I had when we first tried the buttplugs, this sensation of being filled and comforted.

"Mmmmmm" I moaned into the chair. My sissyclit was at attention. He probed more, his thumb probing my insides. I moaned more.

But that's when he stopped. He then leaned over and said to me, "Come on, let's go join the party."

He helped me up. I discretely turned to the side and re-tucked my now-hard sissyclit. It still barely made a dent in my bikini bottoms but I wanted it to be hidden perfectly.

He led me over to the pool. Looking around, I saw Jada dancing between a couple guys. Candi was being chatted up by a tall man who was groping her ass as he talked to her.

That's when I saw Krissy also in the pool. She was just openly making out with a guy, their bodies intertwined. Meanwhile, the Kappas were all drinking and having a good time, chatting with the guys. They paraded around looking perfect while us Cheerbois were getting felt up and teased by these men.

They were like these goddesses and we were like these little toys for mens' pleasure, as if we were the entertainment that they brought to give these guys a good time while they got to look gorgeous and have fun.

Jay led me down the steps into the pool. He took hold of my hand and we drifted in the water to where Krissy was making out with her guy. They were too wrapped up in what they were doing to notice us.

Jay leaned against the side of the pool and pulled me into him, my back against his chest. He rubbed himself against me, and I felt his hard cock against me.

I did that, I had gotten him hard.

He rubbed my body again with his hands. "Damn, you Cheerbois get sexier every year." He whispered into my ear. "Feel how hard you got me." I did, I felt it. And...I was proud of it.

He turned me around and brought his face to mine. He didn't even wait, he just pushed his lips against mine and stuck his tongue in my mouth. I was stunned at first, but I couldn't stop him.

So I just went with it. My tongue danced with his and my lips embraced his. I just let this man grab me and start making out with me. I was acting like a slut and I didn't care.

Wasn't this gay? Sucking cock was like, a fetish, right? It wasn't gay if it was a fetish. But kissing a man? How was this not gay?

But I couldn't resist this, this feeling of him overpowering me. I just went along with whatever he wanted. My will was weak and his was strong. I just submitted to him.

That's when he stopped kissing me and put his hand on my head. He was guided my head down. What did he want? Oh...he wanted me to....oh.

I tried to see Krissy in my peripheral vision but couldn't spot her. His force on my head grew. I couldn't stop him, this was beyond me. So I just dropped down.

My head went below water and came face to face with his swim trunks. I floated in the water a bit while untying the knot and tugging them down with some effort. Instead of springing out, his cock kind of floated up in the water. It was a nice one, long and cut.

He let me up for air but then pushed my head back down. I didn't know how to do this so I just tried my best. Reaching out for his cock I stroked it a few times before opening my mouth. I tried my best not to let the pool water flow into my throat, and just plugged my mouth with his cock.

I couldn't really taste anything, with the chlorine in the pool water just taking the taste away. But the texture was familiar. It was actually kind of easier to suck cock underwater. My head moved gently and the length of his cock was like butter as it sunk into me.

But obviously the breathing, well that was near impossible. He had to let me up to breathe as I tapped on his thigh to signal my struggle.

When he did, he looked at me and said, "Come on, sissy. I heard you won the DSL over at Delta Sigma this week. Show me what you got."

So I did, overcoming my difficulty breathing to try and give him a stellar blowjob. At one point I looked to my left and saw Krissy doing the same as me, sucking off her guy underwater. She saw me too and held up one hand in a peace sign.

I tapped Jay's thigh again and he let me up. "Can you move over to the side? Closer to them?" I said, gesturing to Krissy and her guy.

He did, lifting me up in the water and guiding us over. We were just feet apart.

"Sup, bro?" Jay said to that guy.

"Oh yo Jay. You got yourself a slammin' sissy there." He said.

"You too, man. Looks like she sucks cock like a Hoover!" Jay joked.

"Damn straight, fucking nice mouth she got on her."

Jay had me slide down his body and I went back underwater. I mouthed his cockhead and peeked over at Krissy. She was concentrated on getting her guy off.

I reached over and gripped her hand. She saw me and smiled through the cock in her mouth. And we just went at it, sucking our guys' cocks off while holding hands. It felt really nice.

After a few minutes, Jay gripped my head and unleashed his load in my mouth. I tried swallowing but didn't want any water to get in so I just let the cum flood my mouth. I came up for air and swallowed his load. He pat me on the head.

A few minutes later Krissy came up and swallowed the load she earned too. The guys thanked us and we all hung out in the pool some more. They groped us and talked about sports. Krissy and I got out to grab them beers and joined them again.

After a while, we had to use the loo and they showed us how to get in their house. Krissy and I got out of the pool and walked into their house and found a bathroom. We each took turns tinkling before coming out.

That's when we heard sounds from the garage. We tiptoed over to the garage door, trying to make light work of our footsteps. I slowly opened the door to the garage and peaked in.

Inside a man was on top of Jada, his cock sliding between her asscheeks, like a hot dog in a bun, just sliding back and forth between the cheeks. Jada was letting this man mimic fucking her as the cock just slid back and forth rapidly.

"Yeah Daddy, enjoy this ass. This ass is yours to play with!" Jada said to him.

"Oh fuck, this fuckin' fat sissy ass. Goddamn it's fucking good." He said.

We just stared, and after a few minutes he groaned and spurted his cum into the air, and it splattered on Jada's back.

Krissy and I hurried out before they spotted us.

"What was that?" I asked Krissy.

Krissy giggled, "Jada always has to show up the rest of us!"

"I know, but sucking cock is one thing...giving up other stuff...that's different." I told her as we walked back to the pool.

"Oh come on, don't slut-shame Jada."

"I wasn't!" I told her, as we got to the pool and looked around to find the rest of the Cheerbois.

"You should be proud do her, using her body like that to get that guy off. They looked like they were having fun!"

She was right, they did. And Jada seemed so happy letting that guy use her body like that. She had a look of pride on her face.

"Maybe you're just jealous." Krissy said before walking off and going to talk to a group of guys who each groped her as they talked.

Jada really did have the nicest ass of all of us. I mean, mine got lots of compliments but hers was a whole other level of ass. It was like a 'dump truck', as guys would say. It was impossible to ignore it, as it wiggled every time she moved at all. It was an ass that you could bounce a quarter off of, balance a drink on, that men would write songs about.

After all these weeks, I knew that dressing femme was becoming second nature to me. Looking, feeling feminine...it felt so natural now. Maybe I was getting jealous of Jada. It would sometimes feel like a competition with her, each of us trying to be more desirable than the other, to be the object of an Alpha's attention. I never really had a competitive streak earlier in life, but now I felt it firing up in me.

Lana pulled me aside to remind me to keep serving drinks, which I did, letting my thoughts wander as I handed out beers. The rest of the Cheerbois were doing the same, walking around in our teenie-weenie string bikinis and heels, serving up drinks to these muscled-out men. We were a sight to see, a collection of simpering sissies with hidden sissyclits, showing our inferiority to these men and women. But for some reason, it felt right. I felt wanted.

By sundown we were all exhausted, and happy to see the Kappa girls were ready to take us home. When we reached the Beta House we were all ready to hit the hay.

That night I lay awake wondering to myself, why was I jealous...why was I jealous of Jada? What was it about giving over her body to a man, completely for his pleasure...did that scare me?

* * * * *

HellWeek Day 7: The Final Day

I couldn't believe it, the last day of HellWeek. I had made it this far, as had all the Cheerbois. I was so glad no one had gotten kicked out yet.

That being said, I still harbored doubts. Sure, every time I mastered a challenge, I felt immense pride and worth. But I still held back, wondering if this is what I really wanted. I definitely wasn't gay. That much I knew. I had no interest being Brian and being with men. But as Britney, well...I felt different. There was something so natural about it, so easy about it.

But could I keep going on like this? Sure, this was fun now, but what about in 5 years, in 10 years? How could I hold a job like this? What would the rest of the world think?

Plus, how would my family and friends react? Would my parents reject me, disgusted by what I had transformed into in my short time here at Big U? This isn't what they had sent me to college for. I was supposed to live up to the family name, to be worthy of the trust fund they were setting up for me.

So what...would happens next? What happens if I do pass the last challenge and become a real Cheerboi? What would that mean for the rest of my time at Big U? What would it mean for me and the rest of my life?

Was I ready to make this the new me?

I rolled around in bed, tormented by my conflicting emotions. Then the door suddenly opened and Krissy came running in, wearing a cute little pink babydoll with polka-dot panties. Her hair was in pigtails.

"Can you believe it?!" Krissy said, jumping on the bed next to me. "I literally can NOT! Like, I feel like we've come so so so far and like, this has just been so crazy!"

"Yeah, I know right?" I responded, turning over to look at her. "Maybe, too fast?"

"What!?" She looked surprised. "I mean, I'm definitely blown away by how quickly we became..."

I finished her sentence, "Sissies?"

"Sexy sissies! Sexy sissies that everyone wants to spend time with. I mean, I'm now popular, attractive...I'm like, finally someone that people want around. One of the guys yesterday told me that he wanted me to come to their party next week! I'm not begging to get into parties anymore, I'm getting special invites!"

"Yeah, sure" I responded. "But he probably wants you there to suck his cock."

"And what's the problem with that?" Krissy replied. "So I get to go to a party, enjoy myself, and I get to suck some cock too? I don't see the problem."