My Best Friend's Girl

Here's a rather romantic story I had in my backlog about two college roommates who are friends, with one being a white femboy and the other being a dominant black jock, where the jock convinces the femboy to be his girlfriend for a day. Contains crossdressing and gay sex, but is rather tame compared to most of my other stories. Also has lesbian sex as well. Hope you enjoy. By the way, all characters are 18 or older.

Chapter 1: Derek Higgins

The day has finally come. My best friend from all the way back to kindergarten and I are moving into our dorm room.

We got the dorm room all to ourselves. Just a two-bedroom dorm, big enough for a couch, tv, fridge, and two beds. We got our own bathroom and shower, thank god. I couldn't imagine a communal shower.

This is like the best day of my life. Allen and I have been planning this ever since we both decided to attend Miami U back in our junior year of high school. We already have everything we need for the dorm. We've been ready since summer started.

There's no one I'd rather share a dorm with than Allen. Our friendship is definitely a unique one. At first glance, you would think we'd never hang out together. He's short, I'm tall. He's white, I'm black. Some would say he's on the feminine side, I'm the complete opposite and extremely masculine. He's beta, I'm alpha. He definitely looks like a nerd and everyone thinks I'm a jock. I do play sports, but I got a full ride here on an academic scholarship even though I'm a freshman on the basketball team... I'm still a pretty big nerd myself. That's why we've always gotten along well. As I said earlier, we've been friends since we were in kindergarten. We even had the same babysitter.

Besides, someone needs to stick up for Allen. Being short, somewhat feminine in appearance, and a nerd, he's an easy target for bullies. I spent my entire youth protecting him. And trust me, it involved a lot of fights. For whatever reason, people just love to pick on Allen. Probably because he's so girly. I think that's what I like about him. He's sweet, innocent, kind, gentle, and caring. And fuck me, he's got a body like a model. A butt with a bubble. I still remember the time his sister and I got him to dress up like a girl for Halloween. That was the first time I felt something for him other than our friendship. He looked like the most beautiful girl I've ever seen. Silky dark brown, almost black hair. Warm brown eyes with a smile that can turn the hardest hearts of stone soft. It was then that I knew I wanted him.

Now that we have our own dorm room together, it's my chance to finally make him mine. I know he feels the same for me even though he tries to act all straight and manly. Deep down, we both know he's a sissy. And soon, he'll be my sissy.

Chapter 2: Allen Pratt

This is all so surreal. Derek and I are finally out on our own. Just the two of us as we've planned. This is too good to be true.

The first day of classes comes and Derek and I have all the same classes together. We arrive at our General science class and Derrek pulls us over to a table with two of the most beautiful girls I've ever seen. One's got dark brown hair with a slim figure and long legs. The other is a little shorter with blonde hair and an amazing smile.

"Hey, are these seats taken?"

"Certainly not for you," the blonde one says as she moves her stuff out of the way.

"I'm Derek and this is my best friend Allen. And what are your names?" Derek says.

"I'm Nina," the brunette says with a smile as she holds out her hand. Derek shakes it. "And this is my girlfriend, Julianne."

Both Derek and my jaws have dropped. "God, I love college."

"So, I'm assuming that we're going to work in groups. If we are, would you two like to work with us?" Nina asks.

We're both nodding, furiously. Nina smiles with her sparkling eyes. As usual, all the attention gets put on Derek. Both girls seem to swoon over him. He even grabs the attention of lesbians. "Awesome. By the way, neither Julianne nor I know anyone here, how would you two like to hang out later?"

"Of course. We'd love to. We don't know anyone here either."

"Well, it's settled. We're about to be great friends," Nina says with that gorgeous smile.

The professor starts the class and it turns out we will be working with partners, but since the tables are grouped in four, we're allowed to collaborate.

After class, we meet the girls at this smoothie place on campus. Once we got smoothies, we head out and find a cool spot to sit under some shade. Nina smiles at us. "So, how long have you two known each other?"

"Pretty much all our lives," Derek says after he takes a slurp of his smoothie. "We became friends in kindergarten and have been inseparable ever since."

"Aww, that's cute," Julianne says, biting her lip.

"How long have you two been dating?" Derek asks.

"Since freshman year of high school," Nina says as she takes Julianne's hand in hers. "We have a complicated relationship. We're both bisexual, but we still want to be somewhat exclusive. If that makes any sense."

"Yeah, I get that," Derek says.

"So, are either of you two dating anyone special?" Nina asks.

"Nah. I had a few flings back in high school, but nothing serious," Derek says.

Their gaze finally turns to me and I freeze. "I... uhh.... No. I've never..."

"Let me guess, you're still a virgin, aren't you?" Nina asks.

My face goes bright red, but I nod.

"That's okay. This is college, you'll find someone. Trust me.'

I look up with hope. "You really think so?"

"Of course. Just hang in there," she says.

"Thanks!"

Class goes by rather quickly and the four of us walk out together. I end up colliding with another kid as our books go flying. Derek helps me pick them up. I look over to see a short blonde kid with a frame like mine. Petite. "Sorry about that. I'm Kevin. I need to be more careful."

"It's all good," I say with a smile. "I'm Allen."

"Are you all friends?" he asks as he looks at everyone else.

"We are now," Nina says. "I'm Nina, this is my girlfriend Julianne, and that's Derek. Derek and Allen are best friends from High school."

"I gotcha. Cool. What did you all think of our professor so far?"

"Seems chill," Nina says.

"Yeah for sure." He gives us a smile and tosses his blonde hair out of his eyes. "Well, it was nice to meet you all. I've got to get to my next class."

We end up having to go to our next class and yet I feel like I'm on cloud nine. Things are definitely looking up from high school. People never gave me any attention back then. The only reason I ever got invited to a party or anything was because they all wanted Derek to come and he wouldn't come if I didn't come.

Chapter 3: Derek Higgins

"So let me get this straight... You want to turn your little femboy friend into your sissy girlfriend?" Julianne asks me to chill in their dorm room. I feel bad because I keep ditching Allen, but he can't know what I've got planned. I need this to happen. It's hard to be around him anymore. I want to fuck his brains out. The other day, I got a glimpse of his smooth plush butt and I could barely hide my boner.

"Yeah. That pretty much sums it up. I can't even be around him anymore without being hard."

"That's probably the hottest thing I've ever heard," Nina says, biting her lip. "I definitely see why you'd find him attractive. He's such a little cutie. So delicate and feminine. But a guy like you could literally get any girl here. Why him?"

"We just have a history together. I remember the first time I felt something for him. It was Halloween. Me and his sister convinced him to dress up as a girl for Halloween. It was a triple-dog-dare and he couldn't refuse. His sister literally transformed him into the most beautiful girl I've ever seen. Ever since then, I can't get him off my mind. You have no idea how torturous it is to live with him. It's getting harder and harder to hide my boners."

Julianne and Nina exchange a smirk before Nina speaks up. "I'll tell you what. We'll help you if you let us watch you fuck him."

I nod emphatically. "What did you have in mind?"

"Here's the plan," Nina says as she shows a greedy smile. She goes over what we're going to do in detail, and I love every part of the plan.

"I love it. I just don't want him feeling forced or anything. He's still my friend."

"Oh, don't worry, by the time we're done, he'll be begging to have your dick."

"I hope so."

Chapter 4: Derek Higgins

Back in the dorm room, I find Allen working on homework. "Hey, what's up?"

"Oh, hey..." he says, not taking his eyes from his book.

"Want to play some video games?" I ask.

"Oh, so now you have time? Where's Nina and Julianne?" I ask.

"Are you jealous?"

His eyes go wide and he quickly looks away. "No... It's just... You've been spending an awful lot of time with them and leaving me in the dust."

"Relax man. No need to be jealous. There's plenty of me to go around," I say as his face blushes.

"I'm not jealous," he says.

"Okay... Whatever you say." I can't help but smile. I love teasing him. He's so cute, the way his cheeks seem to sizzle red. His face is so delicate and perfect. Like he was sculpted from ice.

"So what video game do you want to play?" he asks, changing the subject.

"How about a game of 2k?" I ask, knowing that's the only game I can really beat him at.

"Really?" He cringes.

"Oh come on. Just one or two games and then we'll play whatever you want."

"Fine," he says with a sigh as he turns on the console and puts the game in.

A minute later, we picked our teams, and we were off. I go easy and let him win the first game. This gives him a huge confidence boost, and he gets cocky. "That's right. You can't handle my mad skills. I can beat you at your own game!"

"Double or nothing?" I ask.

"Hell yeah! I'm feeling on fire right now."

"How about we make it interesting?" I ask.

He looks up at me; the smile fading. "What do you have in mind?"

"If I win, you have to do everything I say all day tomorrow."

"And if I win?" he asks.

"I'll do whatever you say."

"That's kind of weird."

"Why's that?" I ask. He shrugs. "Look, I just want to get you to clean the bathroom, do my laundry and what not. I've got a long list of chores to do for you."

He laughs. "I'm sure I can think of a few things to get you to do. Sure, you're on."

We start up another game. This time I let loose and dominate his ass just like I intend to do tomorrow. I run up the scoreboard by fifty points. "Yeah! That's right. You're going to be my bitch tomorrow. Get ready because you're going to have a full day tomorrow. I fucking can't wait."

We play another game and I wipe the floor with him. I can see the shame on his face and it turns me on. I'm twisted. I know I shouldn't like it, but I do. Tomorrow is going to be a fucking good day.

Chapter 5: Allen Pratt

Just when I think things will be different from high school, Derek keeps ditching me for Nina and Julianne. It's been a whole week since classes started and we've barely even hung out. He comes up with lame excuses that he's going to the gym to work out or play basketball. But I know he's with them and he won't invite me. Is he embarrassed by me? Do they not like me or something? I don't know. To make matters weirder, he convinces me to play 2K, which I don't really care for and comes up with this bet. What is the deal with this bet? Now I have to do everything he says for the entire day, today.

I lie in bed, just thinking about what he wants me to do today when my blanket gets pulled off of me. "Rise and shine, time to pay up."

I open my eyes to find that Derek isn't alone. Nina and Julianne are with him. I quickly cover my body, as I'm only in my boxers. They both giggle. Nina winks at me. "No point in covering up, cutie, because we're going to see a lot more of you."

"What's the deal?" I ask.

"You don't remember our bet last night?" he asks.

"Yeah, but..."

"But nothing. You have to do everything I say today. All day long." He bites his lip. "And right now, you have to do everything they say because I said it."

"Now come on," Nina says as she grabs my arm and tugs me out of bed. "We've got to get you ready. We've got a full day planned out."

The girls drag me into the bathroom. "What's going on?"

"Don't worry about it. You lost the bet, just go with it," Derek says as I'm dragged into the bathroom.

I'm shoved into the shower and Nina tugs my boxers down. The color drains from my face instantly as I try to cover up. Nina smacks my ass. "Oh come on, it's not like we haven't seen a dick before. Get comfortable because we're about to discover a new side of you."

Nina rips my hand away from my junk and both girls crack up. She points at my little tiny cock. "No kidding, never seen anything so small."

"It's cute," Julianne says.

"What are you doing?" I spit out. The humiliation is written across my face. I just want to cry. "What the hell, Derek?"

I thought we were friends. Why is he doing this to me? I look up as he leans against the door and watches with amusement. "Relax. You agreed to do anything I said if you lost. Now it's time to pay up."

"But this is humiliating," I cry out, biting my lip. Doing everything I can to stop the waterworks.

"Look, it's all in good fun. I will not let anything bad happen. Okay? Trust me," he says. I want to. He's always been there for me, growing up. Always saved me from bullies and protected me. But this is different. He's acting weird. He'd never humiliate me like this in front of girls.

"Time to shave what little body hair you have," Nina says as she pulls out shaving cream and a razor from a bag sitting on the bathroom counter.

"Wait, what are you going to do to me?" I ask, swallowing the lump in my throat.

"Isn't it obvious? Derek's letting us turn you into a little sissy girl for the day. He told us about your little Halloween costume," Nina says with a wicked smile.

My heart literally shatters in my chest. My worst fears are coming true. People are finally going to realize what a girl I am... I look up at Derek with tears welling up in my eyes. "How could you?"

His gaze sends a chill down my spine. He looks at me with a hungry, possessive stare before pity takes over. "Come on. It's just a bet. Besides, I know you cross-dress in private. I've seen your panty stash. We're just helping you come out of your shell."

My face goes pale as the blood drains from it. He knows about my cross-dressing fetish! This is the worst day of my life. To make matters worse, the two most beautiful girls I've ever met also know. They probably think I'm such a pervert. My life is ruined.

"Relax," Derek says.

"Yeah, we're not doing this to embarrass you or anything. I think it's hot. You're such a cutie. I would love to see you all dressed up. It'd be the sexiest thing ever," Julianne says, her hand gently stroking my back.

I look up at her and see the sincerity in her eyes. "Really?"

"Yes. We are bisexual," she says.

Nina pulls my gaze to her. "I'll make a deal with you. If you let us dress you up and give you a total makeover. Then let us take you out on a day of the most fun you'll ever have. We will help you lose your virginity tonight. How does that sound?"

I swallow the lump that reformed in my throat. "Really?"

"Yes, but you have to do everything we say. Deal?" Her eyebrows raise.

"What are you going to make me do?"

"We just have a day of fun planned. A little put-put, a lunch date, some beach time, a fancy dinner, and a night at the club. How does that sound?"

My eyes go wide. "Wait, I have to be dressed up like a girl the whole time?"

"Of course. It'll be so much fun. Trust me," Nina says.

"People are going to see me. They're going to think I'm some pervert or something."

"No one's going to think that. They're going to think you're a girl because, after we get done with you, no one's going to think otherwise. We're going to turn you into the most beautiful girl here beside us, obviously," she says with a smirk. "You cross-dress for a reason, right? Don't you want to find out what it feels like to be a girl? Now's your chance. Besides, you said it yourself. It's not like you know anyone here."

I bite my lip and consider it. She's right. Besides the classmates I run into who I don't really talk to, much, no one knows me. I've always wondered what it'd be like to be a girl. Even though I was talked into dressing as a girl during that Halloween, I secretly wanted to do it. "Okay, I'll do it."

All three of them smile at me. Nina claps her hands together and the two of them get to work. First, they rub shaving cream all over me and start shaving my entire body. After I shower with their girly body wash, shampoo, and conditioner, they do my hair and makeup. Once they finish, I'm pulled into the dorm room as they pull out several outfits. Nina smiles at me. "Since we're going to the beach, you might as well wear beachwear. So try on this bikini and these breast inserts. Make sure you tuck your dick. It's so small, no one will notice it anyway, but it's better to be safe than sorry."

After I tuck my dick back and slip the bikini on, I feel very emasculated. But Derek can't seem to take his eyes off me. He's been giving me this weird stare ever since we started. It's a little intimidating. Like he's hungry and I'm a steak to devour. He's never really looked at me like this.

I realize that the bikini seems to show off most of my ass. It's not a full thong but definitely lets my cheeks hang out.

The girls give me a dress to slip on over it. Julianne steps up with a pair of sandals. "We're going to give you sandals for right now, but tonight we'll have you wear heels. So when we get back, you're going to need to practice walking in them. Don't worry, I'll help."

I smile weakly at her and take the sandals before slipping them on. The three of them look me over. Nina gives me a wink. "Looks like she's ready. The only thing left is to pick out a name for her. How does Alisha sound?"

"I like it," Derek says.

"Alisha, it is," Nina says with a smirk.

They don't even give me a say. Then they pull me in front of the mirror and my jaw drops. Before me isn't a boy at all, but a beautiful girl. I can barely believe it. I've never felt this way before.

"Now, let's go to the beach!" Nina says as they practically drag me out.

We all pile into Derek's car as he drives us down to a very public beach. My stomach is tying itself in knots as anxiety takes over. I can't believe I'm doing this. I'm going to go out in public dressed like this. Like a girl. A really passable and beautiful girl, but not a real girl. What if people find out? What if they laugh at me? My life would be ruined if word got out around campus. I don't even want to think about what would happen if people at home found out. I don't know if I can do this.

Derek parks the car as I am on the verge of hyperventilating. The girls get out, leaving Derek and me alone. I feel his hand on my knee. "Everything okay?"

"I can't do this. This is too much."

"Breathe. You can do this. I'm not going to let anything bad happen to you. You're my best friend." He gently strokes the skin on my knee and it's soothing.

"If you're my best friend, then why are you making me do this?" I ask.

"Because this is who you are. Trust me."

"I did trust you. What if people find out I'm not really a girl?" I ask.

"Who gives a shit? What are they going to do? I'm not going to let anyone mess with you, okay?" He gives me a genuine smile. This is all so confusing. Derek has always been there for me. I still don't get why he'd force me to do this. "How about this? Just to make sure no guy hits on you or messes with you, for the rest of the day, I'll pretend to be your boyfriend. Will that make you feel better?"