Big U Pride Ch. 02: Going Deeper

Please read Chapter 1 to get the full experience and context!

This chapter owes a lot to the SissifyYourself and SissyFactory content. You should check them both out! I also owe a lot to Drogon's hypno videos!

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The 90-foot yacht cruised down the placid clear blue waters, making its lazy way past sun-specked islands. The Mediterranean waters were particularly pleasant this time of year as spring came into full force. It was easy to take in the gorgeous sights of the crystal clear waters and breathe in the fresh air and think that you were in Heaven.

The yacht was named "The CockFighter", which although unorthodox was appropriate for the owner. Dirk Diamond was known worldwide as the owner of a famous cruiseship line under the company "Titillating Trips". The name was a tongue-in-cheek joke since their cruise tours were aimed at young men, and the 'Titillating' was an obvious reference to the large-breasted woman who worked on board. It was like the Hooters of cruise ships, and Dirk made a killing off of young men who wanted to be surrounded by a bevy of young bodacious models as they cruised their way to Mexico or Jamaica or Ibiza to celebrate spring break.

The "CockFighter" christening of the ship was a reference too. Dirk Diamond had made so much money off his cruise ship and tourism business that he decided to make a name for himself in philanthropy. And he couldn't think of a more deserving place to park his money than his beloved alma mater, Big U. Although he hadn't left behind much of a legacy as a student - he was known mostly for the parties that he threw at which he would get shamelessly drunk and inevitably end up doing something irresponsible. He was sort of a Van Wilder figure, and his charm and antics got him both the reluctant approval of the administration and into the pants of the coeds of his choosing.

His most famous hyjink as an undergrad at Big U was his annual Wings & Breasts event. It was a Greek life event where all the frats would judge chicken wings. The catch was that the wings were cooked and served by girls from each of the sororities, all wearing skimpy bikinis. While judging the wings, the guys would also judge which girls had the nicest tits. At first, the administration threatened him with suspension for the event after a feminist group brought it to their attention. But when they saw how much charity money the event brought in, they changed their tune. It didn't hurt that several higher-ups were invited and present at the event.

And now here he was, 30 years after graduating, riding on his luxury yacht out on the Mediterranean, taking in the sights.

"Ain't nothing better than a nice mid-day sunbathing sesh, don't you think?" Dirk said, stretching out his arms as he reclined back on his deck chair.

"Mmmhm." I replied. This was my first spring break and I was lucky enough to be spending it on the college's prime donor's fancy yacht out in Europe. I had won a very special competition to earn my spot here and I was going to enjoy every second of it.

"You know, I've been doing this for the past 10 years, and I have to say it's the best thing about being a proud Big U alum and platinum level donor. Having some of Big U's finest join me on my little vacation is a real treat. I mean, sure, I used to be able to get any model I wanted to join me on the CockFighter, but this is something special." Dirk said.

"Mmmmm?" I asked.

"Why, you ask? Well, very good question Brit. I mean, for one, it allows me to demonstrate my school spirit. I take a special pride in being not only the school's biggest donor but also their biggest booster. And to get to have some of their finest...talen on board the CockFighter with me on this lovely trip just fills me with school spirit."

"Mmmmm." I said in agreement.

"But it's not just that. Like I said, I could have anyone on this boat with me. Any model, any actress. But they can be so...frustrating. I mean, you see these models and they love to prance around wearing sexy things, but then when it comes time to seal the deal they're distracted by their Instagram and Tik Toks. And the actresses, they're even worse. I mean, they play these seductresses in the movies and then you host them for a week and all they do is go on and on about the Broadway plays that they're rehearsing for. Such a let down."

"Mmmmmmm mmmmm." I agreed.

"But what Big U sends me every year, they're exactly what I need. I mean, after finishing my quarterly report meeting with all my investors, I just want to let off some steam and relax. Those meetings can really wear a man down, you know? Well of course you don't but just imagine. I'm just being criticized every damn second, all just because I'm finding creative ways to make more money. As soon as I finish those meetings I just want to take my mind off of it all, I just want to get some...release."

He took off his sunglasses and looked at me.

"And that's why I'm so glad that Lana sent me you and your roommate to join me this spring break." he said.

I looked next to me at my roommate Kris. We had become so so close over the school year and were practically inseparable. After I won the competition to be on this yacht with Dirk, I was offered a companion to join me. I didn't even hesitate, I immediately chose Kris.

"You two are the best stress relievers that I could ask for." he said.

That genuinely made me happy. I loved to help powerful men like Dirk. The fact that I could be that stress reliever for him really filled me with a sense of purpose. And above all it filled me with pride. Not just for being useful to him, but for being useful to Big U. I just loved feeling so...useful.

"Of course, Sir. We're here to make you relax and feel better." I said as I looked up at him.

"Well, of course you do. Now less talking and more sucking. Just because I dropped loads in each of your asses this morning doesn't mean that I don't have another for your mouths." he said.

Without uttering another sound, I ducked back down and put his left ball sack back into my mouth. Kris was right next me, still rolling his right nut in his mouth.

"Oh fuck, I don't know who's the better ball washer - Sissy Britney or Sissy Krissy."

I redoubled my efforts, alternating my sucks and licks of his heavy ball, wondering how he could still feel so cum-loaded after emptying what felt like a pint of jizz in my tight ass and then going for round two on Krissy's rump.

"You know what, it has to be Sissy Krissy. No competition."

I was crestfallen. I had worked so hard to develop my ball licking skills all year. But fair is far, and Krissy was quite the ball washer.

"Don't look so disappointed Britney, I know your real passion is in shaft swallowing. So get to it!"

Now that's what I'm talking about. I gave his ball sack a sweet kiss before letting go, allowing Krissy to take over the ball worship. I leaned forward and grabbed his shaft with my hand and brought to my lips.

With one gulp, I took his cock down my throat all the way down to his well-trimmed curly white pubes. If he wasn't impressed by my sack-licking, then he'd be impressed by my cock worship skills. After all, those skills are what won me a ticket on this boat for spring break.

"Oh fuck me, Brit. That is some fine fuckin' cock-suckin'. Oh shit."

My heart swelled with pride once again. Say what you will about my intelligence, but you couldn't insult my cock sucking skills.

"Oh fuck, hold up hold up. Both of you, off my cock. Any more of this double teaming action and I'm gonna nut."

We both stopped our ministrations. We looked up at him, saliva around our lips and our eyes begging for more.

"Damn, y'all look smokin'" he said.

"Thank you Daddy." we responded.

He was right, we did look damn good. Krissy was wearing a lime green string bikini that highlighted her C-cup tits. Her blonde hair was in a bob and she looked fierce as hell.

Meanwhile I wore a hot pink micro thong bikini. The underwear was essentially a piece of thin string that barely hid anything, but tucked my little sissyclit perfectly. My fat ass was on full display for Dirk and he definitely used every opportunity he had this week to fondle and grope it. Almost as many times as he did that to Krissy's tits.

"Man am I glad I paid for those tits." he said. So were we. The surgery recovery wasn't easy, but the rewards were amazing. We each had C-cup breasts that not only made us look even more feminine but drew him every guy's attention. We were the ultimate fuckbait now.

Dirk had a full view of both of us right now, as he lazed in his large beach chair looking down at us. We were each laying down prone between his legs, with our tits squished against the chair in such a vulgar way. Our asses were propped up, just looking so tempting to him as they jiggled during our oral worship of his cock. Several boats had passed us while we gave Dirk's meaty 10 inch cock the tongue bathing of its life. And as they passed, we enjoyed the hoots and hollers of the men on board as they cheered Dirk, and sometimes us. My favorite was when a man yelled at us, "Go Big U! Fuck those sluts, bro!" only to be disciplined by his wife who came out on deck as he was saying that.

But that did that didn't stop Dirk from yelling back, "Big U sluts fuck the best bro!" Krissy and I both giggled at that. That was the truth.

"Alright, alright. Another reason I love getting you sissy sluts on my yacht instead of the models isn't just your sculpted silicone-enhanced bods, but your devotion to the art of cock worship. In fact, I remember last time I was on campus one of your sissy sisters told me of the Sissy Prayer. Fuck, I don't remember how it goes. Why don't you recite it for me."

"Yes Daddy," we both said, almost in unison.

We wagged our asses back and forth and looked at each other before starting The Sissy Prayer, which we had learned early in our training. We each put our hands together, not so much in prayer but more as if we were begging. We gave Dirk our most pouty look and doe eyes and, in our most innocent voices, we started:

"Our Daddy, who art inside us,

Hallowed be thy cock,

They cock is one, of girth as it

is in length.

Give us this day our daily load

And take us as we were meant to be taken by you

And lead us into temptation

Delivery us your semen

A-OH-MEN"

Dirk smiled at us as we finished.

"My oh my, just absolute cum sluts the two of you. Man I'm so stoked that the CheerBoi program got restarted."

We giggled.

"Now get back to work, gurls. First to make me cum gets to sleep in my bed tonight. Loser has to share the bunk room with the crew."

Krissy and I looked at each other. It was hard to tell what she wanted more: to spend the night with this older hunk vs. surrounded by a bunch of fit olive-skinned young European men for the night. Honestly, I think Krissy wanted to lose! Maybe so did I.

But we had a job to do. We each brought our lips against each side of his thick cock and kissed around it before sliding our lips up and down the shaft.

Maybe if we both made him cum, he'd let us spend the night with him AND the crew!

__________________________________________________________________

7 months earlier...

I stirred from my deep sleep, looking around me and finding myself in an unfamiliar place. Sunlight shone through the windows down on me and the girl next to me. Holy shit, it was Lana and she was asleep on my lap. I tried to pretend to go back to sleep, but I had shifted my body too much and awoken her.

"Oh hey there, sleepyhead." She said to me, groggily as she got herself up.

Wishing I hadn't awoken her, "Do we have to wake up? I'm still pretty out of it."

"Come on, big boy, we should get up before the girls all wake up." she said.

Damnit, lost my chance to cuddle some more with this complete hottie.

"Plus, I don't want Lacey and DeShawn to see us outside their room." she said. "Though I bet you wouldn't mind getting a peak at DeShawn's package again, wouldn't you Brit?" she laughed.

Then the events of last night all came back to me at once, images of Lacey sucking DeShawn's fat cock and Lana egging me on. But for some reason I wasn't embarrassed at all. After all, this girl was somehow into me, even though she had weird ways of showing me that. But hey, if she wanted me to look at some guys' dicks and in return would kiss me like she did last night, then line them up boys. I wasn't going to miss my shot at this sexpot.

"Oh yeah, gonna be difficult getting that mental picture out of mind." I said.

"Not that you'd want to." she retorted.

We tiptoed our way down the stairs, with the evidence of last night strewn all around us. Red Solo cups and champagne bottles littered the floor and I didn't miss the open Magnum condom packages laying about.

"Quite the party we missed." I said to Lana as we got close to the front door.

She looked at me, "I think we had quite the party of our own, don't you think?"

Couldn't argue with her there. I don't think I had as much fun as I did with her last night, for some reason. She just had such a magnetic appeal to her, and, well, made me feel so excited. Everything about her was edgy and captivating and I wanted more. So much more.

She let me out of the house and as I turned to leave she said to me.

"Meet me at the library tomorrow night at 8."

It was an invitation, but when she said it it sounded like a command. And I just had to follow it.

"Yes, Lana." For some reason, that response seemed so natural.

"Good boi." she said as she turned around and shut the door.

Weird, the way she said "boy" just sounded...different. Maybe it was all in my head.

I walked back to the apartment, joining the ranks of all the spent partygoers from last night's revels, as well as the many walk of shame stragglers making their ways home. I hoped people would see me walking out of the Kappa Lambda house and think I got laid. I did my best to look proud of my conquest as I marched back to my dorm room.

I opened the door to my room to find Kris on his computer.

"Hey Brian, how was your night? Did Lana rock your world?" he said, grinning like a kid.

"I can't even begin to explain." I responded. And that was the honest response. She really did rock my world, just not in a way that I could explain to Kris. Nor did I want to admit to Kris that I had spent last night praising another guy's penis.

I mean, Lana had taught me that doing so wasn't gay, but still, I don't think Kris would be so understanding.

"You gotta tell me everything, man. Those Kappa Lambda girls are so fucking hot. I saw them around campus last week and it's like they recruited a bunch of models to be in their sorority."

"It's unbelievable, they're all crazy hot. No doubt Lana is the hottest of them all."

"For sure, bro." Kris said.

"There's this other chick I met too, Lacey. Fucking hot redhead, a real firecracker."

"Oh shit bro, don't tell me you had a threesome."

Trying to sound like a player, I said, "Close, man, close. Lana could definitely hook that up, but she was already taken by the time I got there."

"Oh yeah, by whom?" Kris asked.

"This new linebacker, DeShawn."

"WHAT!? You got to hang out with DeShawn James? He's, like, one of the biggest names around. I mean, he was one of ESPN's top highlights so many times last year. The guy's a fuckin' celebrity!"

"Man, I knew he was a big deal but not that big." I said.

"This year's team has a bunch of all stars and he's definitely one of the biggest names, man. What was he like? I've heard he's absolutely jacked, I mean just HUGE, even for a linebacker."

As soon as he said he was "Huge", all I could think of was DeShawn's massive cock. He may be a football celebrity, but that cock could be porn famous. I remembered how Lacey's spit made it shine like a ebony statue.

"Yeah...he was definitely huge. Real...meaty."

"Oh I bet, the guy is gonna go pro. I just hope he stays a student long enough for us to see him play! Tickets are gonna be so hard to get this year."

"Yeah, yeah."

"But I bet Lana can get us a hookup!" he said, excitedly. Wow, this guy was into the football team. But hey, that's Big U students for ya.

We talked some more about the week ahead and our class schedules. Kris gave me props for getting a study date with Lana tomorrow. Then we got back to getting ready for the week and played some Skyrim before going to bed.

Before I turned off my light to go to bed I texted Lana, "My roommate Kris couldn't stop talking about DeShawn. I didn't realize he was such a celebrity."

She texted back, "Send a pic of your roommate."

Weird request, but who was I to say no.

"Yo Kris," I said. Kris was still on his computer but just wearing a t-shirt and boxers.

"Yeah man?"

"Lana wants me to send a pic of you."

"Why? She want us to tag-team her? Lol."

"STFU, man. Just do it."

"Fine, but don't be jealous when she likes what she sees." I rolled my eyes.

I took a couple pictures of him and sent them to Lana.

She took a few minutes to text back.

But then her reply came through: "Lacey likes what she sees. Tell me to come to the Kappa house tomorrow and ask for her."

Woah, that was a surprise. After seeing Lacey with DeShawn it was hard for me to see what she would like about Kris, a skinny short kid with green eyes and blonde hair that was way too long.

"Really?" I texted back.

"8 pm" was all she responded.

Well, hey, I wasn't gonna stop my roommate from getting his. I mean, he may have been surprised by seeing me with Lana just as much as I was by him and Lacey. But Kris was really nice to me and a good guy so I should help him out. It wouldn't undermine my success in getting Lana, after all she was the hottest one of the Kappas.

"Yo Kris," I said.

"Yeah man?"

"One of the Kappa girls is really into you pic, man. She wants you to come over tomorrow night at 8 pm."

"Oh shit man! You and me, taking down hot Kappa chicks left and right!" he said.

We could barely sleep that night, we were so excited.

__________________________________________________________________

It was really hard concentrating on class the next day as I anticipated my study hour with Lana that night. I was mostly excited about parading around the library with Lana so that everyone could see I was with the hottest girl on campus. I couldn't wait to feel all those jealous eyes on me. Girls would be lining outside my door once they saw what I reeled in.

After classes ended at 6, I quickly went back to the room and changed into a nice pair of shirt and pants, wanting to look good for Lana. Kris was in the room, too, and was doing the same.

"You and me, gonna get lucky tonight!" he said.

"You bet, man. That Lacey is one wild girl." I told him.

"Dude, I hope she's a real slut!" he said.

I felt my heart leap into my chest when he said that word, 'slut'. For some reason, it stirred things up in my mind.

"Yeah, I mean, she's kinda awesome that way."

"What?" Kris said.

"Like, as a slut. Kinda powerful, you know?"

"I really don't, man. Just wanna get her on her knees, you feel me?" he laughed.

"Is that a bad thing? To be on your knees?"

"What the fuck are you talking about, bro?" Kris asked, looking confused.

"Oh nothing," I said. "Just, like, it's kinda cool that she's a slut. I mean, we love sluts, right?"

"Fuck yeah we do!" he said, then gave me a high-five.

Weird.

We both made our way out the dorm and split ways halfway down the quad.

"Get some, bro." Kris said.

With that, I headed to the library. I saw Lana waiting at the entrance. She looked stunning, wearing tight white pants and a crop top. Anyone could see the strings of her thong sticking out the sides of her pants.