Princess Takes a Ride

Kelly was lusted after all the guys at her school, but they weren't worthy of the platinum blonde socialite. They were too unattractive, immature and most of all, very possessive. If Kelly gave them any attention, they'd assume they were her boyfriend. They wished so badly to be a part of the her lavish lifestyle that they tried forcing her into a relationship, but Kelly was a tough cookie who was as smart as she was rich.

Despite being only five foot four- in heels- with a chubby baby face, she was a domineering spitfire to all that knew her. Naturally book smart, the 18-year old wowed her classmates for being so young as a senior in college. Nobody could outwit her in trivia nights, nor match up to her skills in gymnastics, and she have enough humility to not boast about her wealth. Being around Kelly was like befriending a unicorn: you don't see someone like her everyday.

The only fault Kelly had was her antisocial behavior. It grew out of a lifetime of people taking advantage of her status for their own gain, thus she learned not to trust anyone. Yet, even the most reclusive of people had friends, and Kelly's was a 21-year old student called Natalie.

They became best friends after the first weekend of college where Natalie saved her from being swept away by a drunk pervert at a party. She felt in debt to the elder student, and they found out quickly how alike they were. Both of them loved the color green, alfredo pasta, and 90s music. Recently, Kelly discovered that her and Natalie shared another commonality, one that would change their relationship forever.

"I don't know why I'm getting so emotional...uhh..."

"It's okay, take your time."

"Kelly...I never felt like myself, and basically...I'm...I'm..."

Transgender.

Natalie wasn't always Natalie. In fact, her dead name was nothing like the name she goes by now, but Kelly adapted to it quickly. She was incredibly supportive, and didn't treat Natalie any different from before, but there was one big problem. Deep down, the teenager was seething with anger.

For all the guys that tried being her boyfriend, Kelly only wanted one person to hold that title- but now that would never happen.

By senior year, Natalie was almost completely transformed into the woman she always wanted to be, yet Kelly could still see signs of the masculine person she once was. Her strong jawline was still prominent, as was her short, jet black hair that Natalie couldn't wait to grow down to her back, and though her breasts were the size of A-cups, Kelly liked to imagine licking up what used to be Natalie's flat pecs.

A selfish thought came into Kelly's mind as she and Natalie were playing video games in her apartment, "I wonder if she'd fuck me before she fully transitions..." so she asked her bluntly, "Hey, random question, but if I let you, would you have sex with me?" and that led to this...

"HAHAHAHA! Oh my God, that's a good one. You sure know how to make me laugh!"

Kelly's heart felt like it shattered in a billion pieces.

"I'm serious! I was just a lil curious..."

"So what? You're gonna be like my parents now? They already treat me like a zoo animal. Having a trans child is very "in season" for them," Natalie played this off like a light joke, but Kelly knew her parents' approval meant the world to her.

Natalie did receive that, but in a way that was obvious her family cared more about getting brownie points for supporting their kid rather than genuinely understanding her development. Her frustration with them is why she rejected their phone calls lately.

"I was only wondering, jeez..." Kelly lied, sporting a pink blush across her cheeks, "You know what? Forget I even said it..." the rich student put down her game controller and remained visibly shaken by the quick rejection. Natalie took note of this and paused the game.

"Hey, I was just teasing," Natalie said, "You were just kidding, weren't you?" Based on Kelly's quiet brooding, her friend was lost for words, "Oh! Umm..."

"Yeah, nice to get my hopes up!" Kelly let out an angry huff and stormed out of her bedroom. Natalie almost tripped trying to catch up to her, "W-wait! Just hold on!"

"Oh boy..." Kelly's housemate groaned as she saw the couple rushing past her in the living room, "There she goes again."

"That's normal?" the housemate's boyfriend commented.

"It's fine, just another lover's quarrel..."

Kelly and Natalie were on the front porch of the home now, and both of them were feeling a wave of embarrassment over what just transpired. Natalie was the first one to break the ice, making sure she didn't approach the blonde just yet.

"I really didn't know..."

Kelly felt like she was being unreasonable, after all, in their entire four years of knowing each other they never tried anything intimate. It was only after Kelly realized her friend's masculinity was fading away that she started appreciating what she had. But, the gifted student always struggled with apologies.

"Just leave me alone! You're making it worse than it has to be..."

"If we go back inside, it's only going to feel more tense," Natalie predicted, "How about I grab my keys and we take a drive somewhere?"

Kelly couldn't argue with that logic. So, on a whim, the pair drove off to look around the town. It was mostly in silence while music blared through the speakers, but Kelly couldn't stop sneaking glances at her friend.

She admired Natalie's big, brown eyes that reminded her of hazelnuts. She trailed down to her arm that was firm on the wheel, showing off her well-earned muscle from her years weightlifting. The sleeveless sports top was a sight to see as well, as Kelly attempted to look under the large arm hole to get a closer look at Natalie's bra underneath. The blonde was tempted to look lower, but by the time she got there, Natalie was ordering take-out from their favorite fast food spot.

"A good burger always calms you down," Natalie smiled.

"Shut up," Kelly held back her own, chowing down on the greasy meal. From the size of the thing, it looked more like the food was going to devour Kelly, but she was known for having a big appetite which was balanced out by her high metabolism. Natalie was right though, food was the solution for Kelly's attitude most of the time, but she still couldn't shake off the desire to fuck someone she was actually interested in.

The elder student was the only person to make her feel normal when everyone else viewed her as a nepo baby. Natalie never asked for money, or tried to gain connections through her father, all of their interactions were focused solely on her. Kelly fucking a trans woman would really rub it in family's faces too, since that would go against the type of partners they hope for her to marry someday.

Natalie decided to drive the car to an abandoned park that was half an hour away from the apartment. They remained inside the vehicle, relaxing to music in the parking lot as the sun slowly left their view, allowing night time to take over.

"Don't you remember how much we loved coming here?"

"Yeah, it's perfect..." Kelly replied, growing warmer from the memories. They haven't been here for almost a year, which makes sense with all of Natalie's medical appointments. Kelly felt guilty again as she noticed how far her friend would go to put a smile on her face, and she crossed her arms looking defeated.

"What's wrong?" Natalie said.

"Oh nothing, it's just..."

"It's okay, I accept your apology."

"I wasn't gonna apologize!" Kelly snapped out of her depressive state.

"Yes, you were!" Natalie pointed towards her nose, "I could tell by that sorry looking face!"

Kelly smacked her hand away, "Stop it, you're so stupid!" but Natalie surprised her when the hand she slapped her with was grabbed by the wrist. For a moment, the duo stared at one another, unsure of what the other might be thinking. Natalie was brave enough to speak first.

"If you're still down, I'd be open to doing it with you..."

Kelly's face burned with a fiery red as she attempted to pull away, "Don't say that just because I got mad." What could be worse about sleeping with someone than that person feeling pressured to give in? "You said no the first time. I'm not going to try and change your mind."

Natalie frowned deeply, "I know it sounded that way, but if we're being technical..." Kelly wanted to roll her eyes. Natalie was always the type of person to speak on technicalities; it's how she found ways to get out of a lot of shit. "I never said no to you. I just couldn't imagine somebody as pretty as you wanting to do that with me..."

"Why not?" Kelly said in a gentler voice, "You've been with me through everything, and you know I don't talk to anybody else- not like how I do with you...you're amazing."

"Wow..." Natalie removed her grip, "I never thought I'd hear you call me amazing."

Kelly was done with the jokes; it didn't fit into her fantasy of having intense bed-breaking sex with her best friend. She had to take charge or else this would just end up in circles. The short girl crawled over to Natalie's driver's seat with a hand resting on her crotch and hovered over her lips.

"Just for tonight, I promise..." the teenager unbuttoned her friend's pants, "Look at that, you're already hard...."

Natalie never felt so dirty in her life. Sex wasn't this abrupt for her, normally she courted a girl before getting down to the nitty gritty. Kelly was on a hunt for her semen and would stop at nothing to claim it.

"Ngh...I don't know if this is the right time..."

Natalie's jeans were tugged down enough for Kelly to whip out her 7-inch cock. The blonde wasn't aware of it, but she licked her lips hungrily.

Natalie threw her head back against the reclined chair, her heart threatening to explode at the sight of her best friend's mouth wrapped around her dick. Nobody could've convinced her this would happen when they first met.

The trans woman laid a hand on Kelly's head and thrusted up into her throat. The tip of Natalie's cock poked at Kelly's uvula, and made her gag crudely around her shaft. Kelly didn't want to look up, afraid Natalie would hate her for almost puking on her cock, but the intense vibrations the gagging caused only heightened the woman's arousal.

"Kelly, stop," Natalie panicked, "I think I'm gonna cum!"

"Do it," she muffled around her length, "Cum inside."

It didn't take much convincing to follow through with that order. Try as she might've, Natalie couldn't resist Kelly's sloppy tongue work and obnoxiously loud moaning. It gave her insight into a part of Kelly that she always assumed, but never confirmed until just now. It made the socialite that much more adorable in Natalie's eyes.

Shouting her friend's name, Natalie's orgasm took over and she slammed her hips up as her balls drained themselves of a heavy load of cum. "Oh my God..."

Kelly moved back to her side and opened the car door, spitting out Natalie's cum. Then, she got her cup of soda from the fast food spot and sipped on it, saying, "Well that was...something."

Natalie readjusted herself and the seat, so they can head back home. "Was that good for you?" she asked.

"Mmhm," Kelly nodded, "Thanks for that. I feel much better now..."

Clutching the steering wheel, Natalie said, "What does that mean?"

"You know, I just feel relief," the blonde clarified, "I was always a little curious how it'd be like to fuck a trans woman. I'm just lucky enough to have one be my best friend!"

Whether Kelly meant to or not, the girl was sounding exactly how Natalie expected a spoiled brat to behave. She started picturing her friend running up to her family boasting about sucking the cock of a trans woman. "I'm the first one to ever do it!" she would cheer, and everyone would find her so cool and brave for taking such a risk- like Natalie was some type of tamed monster.

Natalie's family came from good money themselves, but not enough to have any high status, so her coming out was their meal ticket to shine in the limelight. "What loving parents they are!" people would say, "Supporting their daughter despite everything!" All of the compliments sounded so fake, and the insecurity Natalie had about being treated like a sideshow was creeping up on her again the longer Kelly talked.

"...So you really think sucking my dick counts as fucking me?"

Kelly looked out the window, feeling sleepy, "Kinda. I thought I needed to have full on sex with you, but that was enough for me."

"Pfft!" Natalie's mouth curled upward, "Sure would be for a virgin."

The driver could feel her friend staring at her in shock, "...How...I didn't tell you that!"

"You didn't have to. Your blowjob said enough."

Kelly didn't like how mean Natalie was acting, "So it was bad."

"Not bad enough to NOT make me cum, so that's something," Natalie replied, getting onto the highway, "I just find it funny how you reacted so strongly to me turning you down at first, only to be satisfied with a blowjob." Natalie's eyes narrowed down the street, like she was chasing something, "You wanna know what it's like to fuck a trans woman? Then you're not getting off this easily. I'm going to give you the full experience..."

Daddy's little princess would never dare be caught having a fat cock stuffed in her ass on top of her bed. He would be horrified to find her clutching the sheets, crying out for the pounding to stop.

"Wait...you're going too fast!"

Natalie reached in front of Kelly to fondle her pussy, then she brought her fingers to her friend's mouth and spread them apart. "Looks to me I'm going fast enough." She shoved her fingers into her blonde friend's mouth, getting harder at the sounds of her choking on them.

"I never noticed how fat your ass is," Natalie nibbled her ear, "Everytime I thrust into it, it jiggles like jello..."

"You're so stupid..."

"And you're fucking sexy."

Natalie was terrible at holding back her orgasms, which resulted in a lot of poorly ended one-night-stands, but when she shot her cum into the condom, Kelly's body shuddered with delight.

"You're cumming inside of me!" her eyes opened wide, "Holy fuck. More...more!"

"You don't know what you're asking for," the dark-haired senior grinned, "but if that's what princess wants..."

"Princess?" Kelly mumbled while they switched positions, "Why did you say-MMH!"

Grabbing her blonde hair in a ponytail, Natalie face-fucked her best friend with a ferocity that you'd find in snuff films. Natalie debated going to therapy after this, because the energy she exuded from taking her frustration out on Kelly was almost disturbing- but not enough to stop.

"Yeah...gag on that cock!" the woman also thought for just a second that maybe keeping her penis wouldn't be so bad. I mean, she'd never be able to have the same sensations if she had a pussy of her own. "You're such a sloppy lover. I'm gonna have to teach you a lesson.."

Kelly felt like vomiting on Natalie's dick; the slobber she was producing was soiling her sheets and the sweat over her nude body were glistening like diamonds now.

"Do you like it?"

"I-MUOV-VIT" Kelly gargled, her blue eyes rolling in the back of her head as her pussy quivered, releasing more cum down her trembling thighs.

Natalie pulled her off, but kept her on her knees so she can be showered in her second load of cum. Kelly yelped when a stream caught her eye. "You better swallow it this time, Princess. You won't get to sleep until you do..."

They came so hard for one another that it was difficult to go for a third round. Kelly and Natalie took a shower, and Natalie sat in the living room taking a hit of her vape while Kelly set her sheets to wash. "What flavor is that? I can't place it," Kelly said upon entering the living room.

"Cinnamon," Natalie held out her vape, "Wanna hit?"

The couple basked in the pungent smell, inhaling into their lungs with dumb reality shows playing in the background. Kelly took one final hit before gathering the courage to ask, "Why did you call me princess?"

"Because you act like one. With your talk about wanting to fuck a trans person. You wanted it, and I gave it to you." There was malice in Natalie's voice, clearly she was still taking those words to heart, and it was then that Kelly finally realized it. The blonde tried to justify her words, saying, "I wasn't saying that like you were some mission to accomplish..."

"Well, it sure sounded that way," Natalie grumbled, "I felt like a freaking weirdo...but I was still horny, and if I didn't fuck you now, then I don't think I ever could..."

"What do you mean by that?"

"Isn't it obvious?" Natalie couldn't believe that Kelly could be so naive, as book smart as she was, "You're eventually going to marry some rich guy and build an empire like your father. Who even thinks of someone like you being with me?"

"...I do."

"Bullshit, you only wanted to fuck me cause it's cool."

"No, I wanted to fuck you cause I like you!" Kelly didn't register what she said, so she continued, "You're my best friend, and you were always good to me. Being trans doesn't change that."

"If I'm your best friend..." Natalie put down the vape, "Then can you at least admit you didn't consider fucking me until I started taking hormones?"

When she put it that way, Kelly could better comprehend what Natalie's deal was. She felt disappointed in herself, because she too didn't like when anyone would only want to be with her because of what she could offer. Natalie had been there through everything without complaint, and now that she's going through this sensitive time, Kelly's first thought was to experiment.

The damage was already done, so Kelly figured the least she could do is tell the truth.

The younger student heard the washer go off, but didn't run for it. She kept her eyes locked on Natalie's and said, "You know what? I did want to fuck you because you're transitioning. I was scared that I could never experience what it's like to have someone truly love me for myself, and if I didn't take my shot, then you'd move on and hang out with other people and grow out of this friendship..."

Natalie's face softened, "...Why would you even think that?"

"Don't they have those LGBT clubs on Wednesdays? You'd find somebody who could relate to you better, instead of me who's just...rich," Kelly lip trembled, "I know most people only care about me for what I can offer, and you're the first person to really want me despite that. So I guess I thought...if I can give you my heart, body and soul...then I won't be alone again."

"Kelly Rita Mcallister..." Natalie sucked her teeth, "I thought you were smarter than that. But, you always were an over thinker." Kelly was still looking away when Natalie sat closer and rested her hand on her thigh, "I suppose we both then look too deeply into things, when the truth is right in our faces...I'm sorry for taking my insecurities out on you."

Kelly wanted to feel the sparks going off in her heart when she looked at Natalie's hand atop her, but the sadness was growing too big, "No, I'm sorry. I shouldn't have been so dramatic, and you have every right to be mad at me. I'm surprised you didn't blow up sooner."

Natalie shook her head like a disappointed mother, "Kelly, are you trying to get me to kiss you? 'Cause I just wanna wipe the pout off your chubby face!"

"Mmmh..." Kelly growled, holding back from snapping at her friend who often liked getting on her nerves. Yet, it was something she didn't want to change about her. No matter how she'll transform, Natalie will always have her heart.

Just then, loud creaks could be heard as Kelly's housemate came downstairs.

"Can we finally stop pretending you two don't love each other?"

"Katherine! We thought you went out with your boyfriend!" Kelly cried.

"I did. But then I came back home just in time to hear you two fucking like animals," Katherine waved her hand in front of her face, "I shouldn't be surprised at how musky it smells in here with all the tension you two built up."