tagTranssexuals & CrossdressersHigh School Love Ch. 03

High School Love Ch. 03


3rd part to "High School Love." Jack and Emily go to a dance and have some fun. Later a previous friend enters into the equation.

Hopefully I fixed the tense issues that were plaguing the first entry (and maybe second). Right now the story that's posted up so far is about 60% of the whole thing. I wasn't planning on continuing this any further, but if the feedback is good and people want more I'm sure I'll continue it. I'm writing another romance/transsexual story. It's similar to this one but I've changed it to the 1st person and the character is more or less based on me (though not my experience). I'll try to sprinkle in a few shorter to-the-point stories as well.

This one starts out fast-ish and ends slow, but there's another build-up as well. Hope you enjoy!

Chapter 6

After their first time making love with one another two months pass and their relationship quite strong. One of the school's dances is coming up and Jack plans on asking his girlfriend to the dance.

"Hey," smiles Jack.

"Hi," smiles Emily.

"How was your day?" asks Jack.

"It was alright, nothing special."

"Yeah, I know what you mean. So..."


"I was wondering..."


"Would you like to go to the dance with me?"

"Of course I would!" gushes Emily.

"Great! Pick you up at 5?"

"Yes! That sounds great!"

"Okay, see you then."

"Okay, bye Jack."

"Bye Emily."

The two lovers can't wait for the week to end, as it's only Monday, but soon enough the week ends and the school dance is upon them. Being prompt, Jack pulls up into Emily's driveway just 2 minutes before 5 pm. He eagerly grabs the roses he purchased earlier and straightens his jacket before heading out of his car and to his girlfriend's door.

[Ding dong] Jack patiently waits for the door. After a little while Emily's mother greets him.

"Hello Mrs. Jefferson."

"Hello Jack, so nice to see you again! And please call me Karen. Won't you come in?"

Karen leads Jack into her humble home and asks him to wait, "She'll be down soon. Would you like anything to eat or drink?"

"Oh no that's all right. I want to save my appetite for dinner."

"Okay, but holler if you need anything," as she wanders into the kitchen. Jack patiently waits on the couch, roses in hand, for his girlfriend.

After another 10 minutes Jack hears footsteps on the stairway behind him. He eagerly gets up and smiles as he sees his gorgeous girlfriend walk down the steps. "Oh wow! You look absolutely gorgeous!!" grins Jack.

"You're not too shabby yourself," teases Emily.

"Ha! These are for you!" he hands her the bundle of roses.

"Oh these are just wonderful! Let me go put these in a vase." She leaves and comes back moments later with a huge smile, "So where are you taking me tonight?"

"I was thinking of that new French restaurant."

"Ooh but it's ssoo expensive. You can't possibly take me there!"

"It's okay, my dad told me to take you there, his treat."

"Oh how thoughtful of him."

"Yeah I know, are you ready to go?"

"Yup, just let me get my purse..."

Soon enough the young couple is in Jack's car and heading for the restaurant. The valet handles Jack's car while the two find their seats with the waiter.

After the hour and a half long dinner the couple eagerly leaves the restaurant and head to the dance. The dance starts at 7 pm but Jack insists they not show up too soon. They don't need to worry though, as the long ride to their school is able to making them fashionably late, by only less than half an hour. Jack and Emily smile as they walk hand-in-hand to the school gymnasium and happy to see that a majority of the school is already there. The two love birds dance with one another for a good portion of an hour before taking a rest at a nearby table.

"I love you," Jack says.

"I love you too sweetie!"

"Want me to get us some drinks?"

"Oh yes please, I would like that very much."

"Okay I'll be back in a giff."

Jack leaves to get the two of them their drinks. Emily sits patiently and watches the other dancers and friends sway about and mingle. I devious little idea causes Emily to smirk and giggle to herself.

"What's so funny?" Jack asks returning from the beverage stand.

"Oh nothing," she giggles. Emily takes the drink and takes a few swigs. "Come with me," she giggles. Emily takes Jack's hand and leads them out of the gymnasium and into the hall. She leads Jack all the way to a secluded area before opening a classroom door with a key.

"What, how'd you..." asks Jack, but he's interrupted by Emily's kiss as she closes the door behind them and locking it. The two make out furiously before Emily pulls away smiling. She seductively makes her way around the teacher's desk and starts to clear the table slowly. Her eyes never leave Jack's as she raises her right leg onto the table. With her leg bent on the table she ushers her lover over by curling her index finger.

"Really? Now?" he asks stunned. Emily doesn't say anything, just continuing to smiling and begging for him to come to her. Jack finally gives in and walks around to the other side. Once there he wraps his hands around Emily's shapely hips and starts kissing up and down her neck. She moans quietly and gingerly hikes up her floor-length dress. Jack doesn't notice this at all until he feels her hands on his suit pants. He breaks away from his kissing and looks down to see Emily's dress bunched up around her waist, "Now take me!" she whispers huskily.

Jack takes a step back and admires his girlfriend's panty-clad butt. He likes it when she wears the fancy stuff. She has on a very sexy blue silk bikini set of panties and he assumes she's wearing a matching bra set as well. Jack finishes admiring Emily's bum and gently slides her panties down enough so her perfect little rose bud peeks out. Emily moans out as her panties are removed and she closes her eyes as she hears Jack unzip his suit pants.

Emily waits impatiently, but feels her lovers cock on her butt cheeks. She moans as the warm pulsating flesh rests on her, "please take me!" she whispers. Jack smiles and grabs his manhood. He guides his member to her love hole and starts to press the head of his cock in. As usual he encounters a bit of resistance from Emily but she finally gives way. Both Emily and Jack gasp as he enters her. Jack in pleasure and Emily more in pain.

Emily places her hands on the teacher's desk in front of her and braces herself as Jack pushes his cock deeper and deeper into her bowels. When she feels him push all the way in she lets out a sigh and a gasp. She smiles again and enjoys the warm feeling inside her bum. Jack lets his hands explore his girlfriend's body feeling her tight body in her elegant dance dress.

"Oh Jack, you feel so big inside me!" she grimaces.

"And you feel great sweetie, you're doing great too!" he moans. He places his hands on Emily's waist and gently rubs her there as he pulls out ever so slowly.

"Uuuuuuhhhhhh" groans Emily.

Jack pushes back in nice and slow and sooths his girlfriend, "that's a good girl."

"Do you love my little love hole?" she asks.

"Oh yes baby, it's absolutely amazing" he whispers back while still slowly pushing in and out. Jack leans forward and gently cups Emily's breasts through her dress and gently kissing up and down her neck.

"Oh god Jack, that feels so goooood!!!!" she moans. Jack does this for a little while longer while continuing to slowly fuck Emily. Feeling extremely aroused and in a bit of a hurry Emily begs Jack, "Fuck me now!" Jack loves pleasing his girl so he doesn't hesitate. He replaces his hands on Emily's shapely hips and starts to increase his speed gradually.

"Oh my god!!!" groans Emily. Her little erect cock bouncing with each thrust. "Oh shit!!!!"

"You like that baby?" whispers Jack.

"Oh my fucking god, yes!" moans Emily. She places her hands on the teacher's desk and braces herself for each impending thrust. Her heart begins to race as she feels her orgasm approaching. She also notices her panties becoming a little damp from her precum.

"Oh Jack!!" she moans. She buries her head in her arms as Jack continues to quicken his pace, trying to muffle her moans.

Jack gently rubs Emily's waist and now briskly thrusts his pelvis into her. The faint sound of slapping skin fills the room as Jack gets closer and closer to orgasm.

Off in a trance, Jack awakens when he hears Emily's breathing. She grunts, moans, and groans with each thrust and he knows she's about to pop. "Oh my god!!! Don't stop!!!!" moans Emily.

"I won't baby," grunts Jack.

Emily's panties are covered in her precum and she feels her tiny cock twitch with arousal. "Oh fuck me!!!! Oh Jack!!! Fuck me!!!! Fuck me!!!! FUCK ME!!!!!!!" Jack thrusts harder and harder until he feels his girl tense up and knows what's about to happen. Emily freezes up slightly but then she spasms all over the desk as she orgasms inside her panties. Spurts and spurts of cum explode out of her little cock and into her panties, coating the inside thoroughly. She moans loudly as Jack continues to pound her asshole.

Jack is very close as he feels Emily's asshole clench and unclench under her uncontrollable orgasm. The feeling is wonderful and he doesn't know if he can hold out for much longer. To his disbelief after Emily's orgasm subsides, he's still pounding away at her and feeling better than ever.

Trying to finish up soon, Jack grabs onto Emily's hips and starts slamming himself into her. He hears Emily's breath start to quicken again and hopes he's able to make her cum again. However before he gets his hopes up he feels the burning sensation in his loins as his cum begins to boil inside.

"Oh Jack!!! Don't stop!!!!" she screams. Jack pounds and pounds his cock inside Emily's asshole and can't hold out for too much longer.

"Oh baby, I'm close!"

"Fuck me!!!! FUCK I'M CUMMING!!!!!!!!" Emily convulses again on the desk and her tiny cock starts spewing more cum into her panties. She unloads three heavy gooey reams into her already soiled panties before she finally stops. For Jack, her asshole is just too much this time and he too unloads seven thick spurts of cum into Emily's bowels. He groans and stays inside Emily until he's completely finished before pulling out. He slips his softening cock in his trousers before zipping up his suit pants. As a gentleman, Jack helps his girlfriend off the teacher's desk and she rearranges herself. Emily giggles as she pulls her panties up, feeling her thick goo on her softening erection and feeling Jack's seed inside her warm bowels. She feels some of it leaking out, but doesn't mind as her cute little panties help conceal this. She lets her dress fall and smiles to Jack, "Okay I'm ready to dance some more!" she giggles.

"Okay," he says with a smile. The two lock arms and make their way back to the dance floor. "I love you so much Emily."

"I love you too Jack. Oh and that was the best sex ever!" she giggles.

"Thanks, and it was..."

The two love birds make it back to the dance and dance the night away before returning to their secluded hill top. There, Emily sucks Jack off and makes him explode in her wet mouth. She hungrily slurps down his essence and smiles, "Can you take me home?"

"That was great babe, do you want some?"

"No, I think I'm spent, but thanks," she smiles.

Jack smiles and takes her home.


"Night, Em."

Chapter 7

With just two weeks before school gets out all of the students are jittery for the summer. Emily and Jack's relationship gets stronger and stronger as the school year goes along and are now almost inseparable as a couple.

"Hey Jack, wanna come back to my place?"

"Sure, just let me finish up here."

"Okay, I'll wait by my locker."

"Okay, see you there."

Emily leaves smiling to herself. She carries her books in her arms in front of her chest as walks towards her locker. She's quite horny and walks around with a tiny erection all afternoon. She's glad she has on a loose skirt today, hiding her tiny secret from all. On more than one occasion she nearly leaves to relieve herself in the girl's bathroom, but resists the urge, remembering to savor the sensation of release.

"Hey Emily."

"Oh hi Jamie, what's going on?"

"Um, well... we're friends right?"

"Yeah, of course, you're one of my best friends Jamie."


"Yeah, I thought you knew that."

"Well, I wasn't sure."

"Well now you know, so what's up?"

"Can we talk in private?"

"Um, okay," Emily says with a smile. Emily takes Jamie's hand and leads them to a more secluded area of the school.

"So, what's on your mind?" asks Emily playfully.

"Well," starts Jamie, "I don't know how to say this, but I like you a lot."

"I like you too, Jamie."

"No I mean I really like you. I think you're so pretty."

"I think you're pretty too Jamie." Now that she thinks about it, Emily really does think Jamie is pretty, her cute face, button nose, perky little breasts, she guesses maybe a large A-cup are small B-cup, her brunette hair, green eyes, and shapely body. Wow, am I really thinking about this girl like that? She thinks.

"No I mean..." Jamie all of a sudden leans in and kisses Emily on the lips. Without even thinking, Emily closes her eyes and opens her mouth. She instinctively embraces Jamie and kisses her passionately for a long while before she even realizes what she's doing. She opens her eyes and pushes Jamie away.

"What's wrong?" she asks.

"Um... I don't know, I've never kissed a girl before," admits Emily.

"Me neither," smiles Jamie shyly. Emily hears a ring and vibration in her purse. She checks her phone, "Hey where r u?" it reads. "Um, do you wanna walk with me?" asks Emily.

"Okay," says Jamie. The two girls walk back to Emily's locker.

"Oh there you are, I was wondering where you were," says Jack with a smile.

"Oh yeah sorry Jack," apologizes Emily, "had to pee. You remember Jamie?"

"Yeah, nice to meet you again Jamie," says Jack.

"Hi Jack," she smiles shyly again.

"We were just talking, and she wants to know if she could come along."

"Oh, um, sure I don't see why not," says Jack.

"Great!" says Emily. She smiles at Jamie who smiles back unsure of this but she decides to tag along. The three head to Jack's car and they all drive to Emily's house. Her mother's out at work and Emily lets them all in. They comfortably sit in the living room area and watch some television. Jack and Emily sit together, draping over each other while Jamie sits by herself nearby stealing glances at the two.

The rest of the afternoon goes by quickly with the three chatting, playing games, and watching TV before Jack and Jamie go home. As usual, Jack being the gentleman takes Jamie home. Neither Jamie nor Emily bring up what happened earlier, but both know they'd be talking about it soon.

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