Big U Pride Ch. 02: Going Deeper

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I walked out to see Lana playing on her phone. She looked up.

"OH MY GOD BRIT!" she said. "I LITERALLY CANNOT BELIEVE IT."

"I look like a fool." I said. "This is like some freak Halloween costume." I turned to change back into my clothes.

"Don't you dare, Brit! You look AMAZING!" she said, getting closer to take me in. "Honestly, I just can't believe hot perfect this looks on you."

"Umm, well thanks."

"You know what, you have a tiny little blemish on your chin that we should cover up" She grabbed my hand and brought me back into her room and sat me down at her table.

She looked down at me as I sat there looking up at her. Lana grabbed her makeup kit and opened it.

"I don't know bout that." I said.

"Oh don't be so silly. I hate when men try to act all toxic hetero."

"Everyone will make fun of me if I have makeup on."

"It's just to cover your blemish, silly. Plus, male actors wear makeup and no one makes fun of them. I mean, even The Rock wears makeup and he's a prime specimen of masculinity, isn't he?"

"Fine, just cover it up."

So she got to work on my chin blemish, rubbing in some creams and then some paste. But then she started rubbing things on other parts of my face. I thought this was just for my chin...

"You know what," she said, looking at my eyes. "I think I could make your eyelashes pop. Plus, your gorgeous blue eyes aren't getting the attention they deserve."

And without even asking my permission, she took out her eyelash curler and mascara and worked on my eyes and eyebrows.

A few minutes later, she stopped.

"Oh, and this hair. I love how long it is, but it's a bit...floppy."

"Yeah, it's my messy look, like 'I-just-got-out-of-bed look. Girls love that."

"Some girls...but I think some product would help." She grabbed some mousse from her bag and smeared it through my hair, mussying it up and then smoothing it out.

"There, perfect!" she said. "Oh gosh, let's show you the full thing!"

She pulled me over to her mirror, covering my eyes as she did.

"Ta-da!" she said, uncovering my eyes.

I looked in the mirror and couldn't believe what I saw.

I was...stunning. I mean, yes, I looked like a girl, but wow...a gorgeous one. If I saw standing on the street what I saw in the mirror, I would gawk.

My blonde hair was done in a way that made me look a little pixie-esque, sort of like Carey Mulligan.

I was...hot. I'd never felt this attractive before in my entire life. I turned to see my profiles and admired how nice my ass looked.

"Like what you see?" Lana said, interrupting my reverie.

"I'm...hot." I replied.

"YES YOU ARE!" she said and embraced me. We stood there looking at ourselves in the mirror.

"You'd fit right in with us Kappas looking like that. Isn't that so cool?" she asked.

"Yeah, amazing." I said, still staring at how good I looked.

"Enough vanity!" she said. "Time to pre-game!"

Lana made us some really strong cocktails and lit up a blunt. We sipped our drinks and toked up, as Lana asked me about the videos she had us watch. I told her all about how exciting they were and how they changed how I saw porn.

I felt myself getting lightheaded and hazy as we drank and smoked, and we eventually we just gossiping about famous athletes on campus and she was telling me which ones she knew and how they all wanted to party with her. I just sank in and smoked and got drunk while I stroked my shaved legs and admired my flat hairless midriff. I was really enjoying this.

"No time to waste, then!" Lana then said. "Let's go party!"

I was too gone by then to refuse or tell her that I couldn't possibly be seen in public like this. Instead, I just followed her.

"But before we leave, choose your lipstick Brit!" she showed me her array of different colors. I chose the hot pink just because I thought that's the color I found hot on girls. When I put it on, I made a kissy face to the mirror just to be fun.

We then made our way downstairs with Lana holding my hand.

The music was pounding, loud hip hop and rap songs that I barely knew. Lana dragged me through throngs of sweaty people until we got to the basement. Down the steps we went until we were in the thick of it, with gyrating bodies all around as a DJ played a dirty rap song.

The song, I found out later, was called "Dance (A$$)" by Big Sean.

I heard the lyrics as we walked through the crowd to the bar.

"I'm looking all good I'm making her wet

They pay me respect they pay me in checks

And if she look good she pay me in sex

Bounce that ass its the roundest

You the best you deserve a crown bitch

Right on that ass"

As we got closer to the bar, I felt a hand squeeze my ass. I looked at who did it but couldn't figure it out, there were just too many people. I somehow didn't mind it though.

We made it to the bar and Lana handed me a drink and I gladly drank it up. My first college party and I was hanging with the hottest girl on campus while I looked...like a hot girl. It would have been too much to handle had I not been so drunk and high.

A guy walked up to Lana and said something in her ear. I couldn't hear anything they said since it was so loud, but after he talked to her Lana came close to me.

"He's one of the new basketball players and he and his friend want to dance with us."

"I...I don't know about that." I yelled over the noise into her ear.

"Oh come on, Brit!" she said. "Just go with the flow - dance with me and they'll dance around us."

Well, if it meant dancing with Lana...

"Ok!" I said to her.

She grabbed my hand and we moved to the middle of the dance floor, surrounded by people. The guy, a tall buff guy in a tank top and shorts followed us, and he signaled to his friend, who was somehow even taller and jacked. He was also just wearing a t-shirt and loose gym shorts.

Lana grabbed me and starting shimmying her hips against me, thrusting her butt into my crotch. If these shorts weren't so tight and my penis so small, I'd definitely be sporting an obvious boner. But alas, I was aroused and left no evidence of it.

I rubbed my crotch into her ass and swayed with her. I looked around and saw lots of guys grinding with girls like this, but I realized I was dressed like a girl and we must just look like typical college girl ho's dancing with each other trying to look sexy.

But I went along with it because Lana was moving so sexily and I enjoyed feeling her body against mine.

The guys then made their move and one came in front of Lana and the other guy (the bigger one) behind me. They started grinding against us from both sides. I just kept swaying with Lana, but then she turned around to face me.

Her eyes were closed and she was smiling, as the guy came up behind her and grabbed her hips. She put her arms up and played with her hair as she shook her ass against his. Wow, she looked so sexy.

I was mesmerized, but then the other guy grabbed my hips from behind and ground himself against me.

The first thing I noticed: I'd never been touched by a guy this way before.

The second thing I noticed: His big bulge was rubbing against my ass.

I looked at Lana, bug-eyed and scared. She grabbed my chin and kissed me before saying in my ear,

"Just do what I do."

She put her hands on the guy's hands on her hips and shook her body left and right.

So I did the same.

Then she rolled her body and thrust her butt against the guy's crotch.

So I did the same. I felt his big member stir in his shorts.

She spread her legs apart and ducked down at the waist and flipped her hair up as she leaned back up.

So I tried to do the same, but much clumsier. But it still had the same effect, as this guy's cock was enlarging. It felt like a can of cookie dough rubbing between my ass cheeks. Honestly, it felt kind of nice to have something wedged between there. Almost like it filled the gap nicely...

We kept gyrating against the men behind us and Lana grabbed my hands as we swayed together against them.

The lyrics kept going:

"Bad bitches I'm your dada white girls go gaga

Sticks out they bust so it they open like yaya's a pinata

Bitch look down tell me what's up

Girl you talk to much shut up

I got that mad dick you know it always nut up

And it got a attitude no wonder why it's stuck up

Pop it then back up yo gymnastics got me ecstatic"

Lana smiled at me and I smiled back, truly enjoying how she was guiding me along. I don't know why but I didn't think twice about the idea of a guy grinding against my ass. I was soaking up the feeling of being desired.

I had the hottest girl around playing with me as a popular basketball player thought I was hot enough to dance with. I was literally desired by the most popular people on campus and it felt...amazing. I wasn't a nobody anymore. I wasn't just another skinny little white boy without romantic prospects. No. I was this sexpot dynamo that was enjoying the attention of people who wanted to bed her...I mean him.

The song kept playing as I tried to shake my ass in earnest against the guy behind me.

"Short girls (short girls)

Go small girls (small girls)

Go skinny girls (go skinny girls)

Go all girls (all girls)

Shake that ass girl

Shake that ass girl

Shake that ass girl

Shake that ass girl

And I want all of that ass

Stop, now make that motherfucker hammer time like

Go stupid, go stupid, go stupid, go stupid, go stupid"

I felt like I really did "go stupid", just shaking and dancing and playing with my hair as I teased the guy behind me.

Then the song faded and a slow R&B mood song came on. That's when I snapped to and realized I was still gyrating on this guy.

I stopped, feeling kind of embarrassed. Lana thanked the guys, who clearly wanted to take us outside and do horrible things with us. Then we walked back to the bar.

And that's when I saw her.

She was dancing with Lacey and kissing her in the corner. But our eyes met. This cute pixie-girl with blonde hair wearing a black jumper that showed off her lithe body and curvy ass.

Lacey say me too and whispered in her ear. They walked over to me and Lana at the bar. Lacey said a few words to Lana as the new girl just looked so cute next to her. Then, Lana, Lacey and the new girl went back to the dancefloor and I followed along.

We all then threw out sweaty bodies against each other and started grinding against each other. First me with Lana, then Lana with Lacey...and then last with me and the new girl.

I even drew up the courage to squeeze the new girl's ass and it was so plump and felt amazing in my hands.

Then Lana and Lacey grabbed both of us by the hands and walked us out of the basement to the main floor. When we got the the main stairs, they gestured us upstairs as they waited downstairs.

So I walked up to Lana's room with the new girl in tow. I couldn't believe I was about to score with this girl that I had just met. Maybe she wouldn't mind that I was actually a guy despite how I was dressed tonight.

I opened Lana's door and the pixie girl followed me inside. I didn't know how to make a first move so I just sat on the bed and looked at her. She also seemed shy and slowly went to sit next to me.

I put my hand on her leg. She did the same to me. Her hand was so petite and cute, though I guess mine looked similar.

I looked deep in her eyes, those gorgeous green eyes. Then I just decided to make my move and dove in for a kiss.

She didn't seem to mind my aggressiveness, and actually returned it in kind by sticking her tongue in my mouth.

Our tongues battled as we made out on Lana's bed. I reached over and put another hand on her, this time on her side to draw her in. She upped the ante by climbing on top of my lap as we continued to make out with each other.

Wow this was hot. If these shorts weren't so tight, I'd be bursting.

But then we heard noises outside the room, the sounds of deep male voices as well as Lana's higher voice.

I panicked. And so did this new girl. She hopped off of me and I looked around. I saw Lana's closet and realized we could both slip in there and hide.

So I ushered the girl to join me in the closet and shut the door behind us as the front door of Lana's bedroom opened.

There was Lana with Lacey, and behind them the two guys that I had been dancing with earlier with Lana.

They were kissing and groping each other as they both fell back on the bed. These two couples went at it like animals, pulling their clothes off each other. Lana and Lacey were quickly down to their lingerie while the guys tossed their clothes on the floor hurriedly.

The girl and I watched as Lana and Lacey got on their knees on the floor as the guys sat on the edge of the bed and took off their boxers.

But our eyes were diverted to what those guys were packing. Each had dicks that were at least 8 inches long, and both meaty. I didn't know what was hotter, these two girls on their knees in lingerie, or the sight of those big dicks about to please them.

The pixie girl next to me seemed to be getting turned on too. She was wide-eyed watching the scene in front of us.

The second the girls' lips touched those cocks, the pixie girl grabbed my hand. I could feel my heart racing as I got turned on watching the sexiest girls I had ever seen go down on these two delicious looking cocks.

Did I just think "delicious looking cocks"?

The pixie girl started rubbing the front of her jumper shorts. Wow, she was getting into this.

I looked at her face and her tongue was practically hanging out of her mouth. I realized that I too was salivating more as I saw Lana suck the head of the cock in her mouth.

I couldn't take it any more, I dove at the pixie girl and starting kissing her again. We made out harder than before and I ran my hands all over her soft body. Her skin was so supple and smooth and I slipped my hands on her thighs and up her jumper. She gestured me to stop so I resigned myself to running my hands up and down her smooth long legs.

We went at it for what must have been minutes, just trading spit and rubbing ourselves against each other.

We were almost so lost in each other's bodies that we didn't notice the front doors opening and closing and then the closet doors being swung open.

"OH WELL WON'T YOU LOOK AT THIS!" came a voice standing over us.

I was on top of the pixie girl, each of us writhing against each other, and we both looked up at the voice.

It was Lana.

"That didn't take much at all." A smiling Lacey was standing above us now too.

"I..." I started, about to apologize to Lana for getting caught watching her hook up with a guy. I wanted to explain that I wasn't a pervert and that I was just trying to get with the pixie girl but we both got caught up.

"You don't need to apologize...Brit." Lana said.

At hearing my nickname, the pixie girl sat up startled and made a sound of shock.

"Oh, don't look so surprised...Kris." Lacey said.

Oh...my...god. It...it couldn't have been.

I looked at the pixie girl then back at Lacey.

"You couldn't tell this little sexpot was your roommate Kris?" Lana said.

"And Kris, you really didn't figure out that that fat ass could be none other than your roommate Brit's?" Lacey said.

I couldn't believe it. This sexy pixie girl that I had spent the past hour hooking up with was...Kris!?!? My roommate?!? My MALE roommate?!?!

"Just admit it, you liked it." Lana said.

I was speechless. But...she was right...I did like it. Those soft lips, that smooth skin, that ass. I had just enjoyed hooking up with my male roommate who was dressed like a girl. And he...well he thought he was also getting with a girl. I...was dumbfounded.

"Go ahead, give Brit a kiss" Lacey said to Kris.

Kris nodded his head side to side.

"Oh come on, you were just getting off on it. Or were you getting off looking at us handle those big dicks?" Lacey asked.

"Yeah, was it more exciting watching us...or watching those nice big dicks?" Lana teased.

Kris looked at me and leaned forward. I did the same and our lips met.

Then we saw a flash of light. The girls had just taken a picture of us kissing.

"Why???" Kris asked, looking ashamed.

"Oh don't worry." Lacey said, showing us the picture on her phone. We looked like cute lesbians kissing. "It's not blackmail. Or rather, it's not blackmail yet. Think of it more like the first picture in the next chapter of your lives."

"That's right," Lana picked up. "You're about to find out a whole lot more about yourselves and what your time here at Big U will be like. And trust me, I think the two of you are going to love what you'll become...and who you'll do that with."

They then offered their hands to help us get up. We each took their hands and stood up.

"Now then, don't you want to find out what's in store for you?" Lacey asked.

Kris and I looked at each other. We couldn't believe the positions we were in. Dressed up like girls and surrounded by the hottest chicks on campus, this was far from what we expected of college. But we'd be lying if we said this wasn't the most fun we've had in a long time...actually forever. I had just had the most sexual experience of my life after dancing with Lana and two guys who would have killed to spend more time with me. I was finally with the elite - the cream of the crop wanted me around. I wasn't the boring kid with the rich parents. I was something else altogether now. I'm not sure what it was, but it was endlessly exciting. And I was enjoying it with two hot girls and my friend and roommate. How could I not see what would happen next?

Maybe it was the weed, maybe it was the alcohol. Maybe it was looking like gorgeous little sluts.

Whatever it was, we were incapable of saying no. We just wanted to go further down this rabbit hole and never leave this fantasy land.

Kris and I nodded.

"I need you both to say it." Lana said.

I knew what she wanted.

"Yes, Lana." I said.

Kris spoke up.

"Yes, Lana."

"Good bois. I'm so proud of you." she said.

"Are you both ready to take the next step?" Lacey asked.

"Yes, Lacey" we both responded.

"Then get ready for the best year of your lives." Lacey said. "This campus is about to get a whole lot of Brian and Kris."

Lana stopped her.

"Or maybe we should say, Sissy Britney and Sissy Krissy."

To be continued...

________________

In Chapter 3...they bois get induced into the CheerBois and learn to embrace all the pleasures of sissy life.

Like and comment if you want to see more! Email me if you have ideas or suggestions or just to drop some note of praise!

XOXO

LatinaRita

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
17 Comments
Veronica_E_DayVeronica_E_Dayabout 2 years ago

Wonderful story and the bois are adorable. I am looking forward to the next chapter.

Veronica

AnonymousAnonymousabout 2 years ago

Best series I’ve read here! Enjoy the pace and love the journey!

AnonymousAnonymousover 3 years ago
Woooooo!

My favorite story series

AnonymousAnonymousalmost 4 years ago
amazing

next chapter please

AnonymousAnonymousalmost 4 years ago
Love It

Please write chapter 3 soon! I totally love this story. I can hardly wait to see their transformations.

Show More
Share this Story

Similar Stories

"Sissified": 12 Days of Sissy-mas Straight man is turned into a submissive sissy by...in Transgender & Crossdressers
Lesser of Two Evils A man's choices will transform him into a cum slut.in Transgender & Crossdressers
Dream Girl Pt. 01 Get the girl... or become a girl for BBC.in Transgender & Crossdressers
In Time for Summer A boy gets seduced by his "lesbian", packing roommate.in Transgender & Crossdressers
A Harmless Favor A young wife assists her young husband to become a sissy.in Transgender & Crossdressers
More Stories