tagTranssexuals & CrossdressersHigh School Love Ch. 02

High School Love Ch. 02


2nd Part of "High School Love." I should have mentioned in the previous iteration that all characters are at least 18 years of age. This second part is a bit longer and finally gets to the action that I'm sure most of you are here for. Hope you all enjoy!

Chapter 4

Over the course of a month the two go on five dates before declaring themselves as boyfriend and girlfriend. Jack successfully, albeit awkwardly, kisses Emily on the second date. The two hang out as much as possible during and after school as their relationship progresses. During that span, nothing goes past kisses and maybe some light making out. Jack is patient and honors Emily's request to keep the physical side of the relationship slow. He honors it so much that he doesn't even allow Emily to give him a blowjob or handjob, which she objects to at first but then she sees his reasoning. His reasoning being if he can't pleasure her then she can't do the same to him, he doesn't think of it as a punishment to himself – like many guys will – but as a way to honor his commitment to her.

Now being November, the school has a dance that the couple attend. They dance the night away, even if no one but their friends, Jason and Tom and Pam, Kelly and Jamie, really know about. After the dance Jack and Emily leave together.

"Hey can you drive up to the lookout point tonight?"

"Sure," he says. They go there quite often but only cuddle and make out while up there.

They get up there and the full moon is out. The sky is clear and they can see the stars. Jack is very fond of space and its vastness and can't keep his eyes off the gorgeous night sky that is until Emily speaks up, "Hey Jack?"

"Yeah Em?"

"I wanna... I wanna make you happy."

"You do make me happy."

"N-no I m-mean phy-physically," she stammers.

"I know you do babe, but I won't do it unless you let me pleasure you."

"But, I really wanna," she starts to sob.

"Hey, hey, you don't need to cry babe," he says sympathetically. He wraps his arm around her, cuddling even closer. This seems to calm her down. She looks up into his eyes with tears in her own.

"Do you love me?" she asks.

"Yes I do, I truly love you. You are the prettiest girl in the world and I love you dearly, nothing would change that."

Emily starts crying even more, but tries to sober up, "can you take me home?"

"Sure babe," he says while rubbing his arm on hers.

Jack takes his girlfriend home and drops her off, telling her goodnight and that he loves her. He gets in his car and leaves for home, Man, I wonder what got into her tonight. It was a great night, we danced like it was just us out there, a beautiful night sky and she cries after I tell her I love her... I think I'll call her tonight to see if she needs more help cooling down or see what's wrong.

He gets home and keeps his promise, calling her later that night.

"Hey babe, you alright?"

"Hey Jack, yeah I'm better now. I think it was just the time of the month, that's all."

"Oh okay, I was really worried after I dropped you off. You know, I meant all those things I said. I do love you, more than anything."

"I know you do, and I love you too, with all my heart," she starts to sob again but moves the receiver out of the way.

"You there Em?"

She chokes back her tears, "Yeah, thanks for checking in Jack."

"Yeah of course. I'd do anything to make sure you're happy, anything."

"I know, well I feel better now, thanks again. Goodnight."

"Goodnight Em, sleep well." With that the two hang up.

It still worries Jack that she's so upset and kind of caught on that she still hadn't recovered. Hopefully she'll feel better tomorrow.

Chapter 5

November finishes up and December comes and goes and the New Year rolls through quickly. The couple spend a lot of the winter break with one another and kiss on New Years at the strike of midnight. Emily vows to take the next step in their relationship for the New Year and wants to do it the first weekend school gets back. The first week of school comes and passes and it's Friday night of the first week back.

As usual Jack and Emily are out together. It is rather chilly so they stay inside the mall to stay warm.

"Hey Jack?"

"Yeah Em?"

"Can you take me back home?"

"Okay," he says as he glances down at his watch, it's only 8:34 in the evening. Maybe she's tired. The two get into his car and he drives them back to her place. Emily's mom is out of town for the weekend so Emily is by herself for the entire weekend, which is not known to Jack.

They get to Emily's house soon enough and she invites Jack in. Sine he doesn't know Emily's mom is out he is none the wiser when Emily grabs him and pulls him down with her to the couch and starts making out with him.

The two teenagers furiously go at it when Emily pulls away. "Wanna take it into my room?"

"Okay," he says thinking nothing of it as they've made out in her room numerous times. Emily grabs Jack's hand and leads him up to her room. She sits down and then lies back while he comes over top of her and begins kissing again.

They do this for a while before Emily grabs Jacks hands and place them on her breasts. Jack hesitates, a bit astonished because she almost always bats his hands away if they wander at all. But here he is on top of her, making out, and now lightly squeezing her breasts through her blouse. He feels the soft mounds of flesh and Emily moans at the attention.

"Oh... Jack..." Emily says in between kisses, "Oh... that... feels so... good..." Jack starts to work his way down her blouse and starts to kiss around her neck and upper chest while still fondling her B-cups. He wants to try something, so he starts unbuttoning Emily's blouse. He pauses after the first button, thinking she might stop him, but she doesn't so he continues. Eventually all of the buttons on her blouse are done and he pulls it open revealing her perky B-cup bra. He's quite happy to see a simple pink cotton bra and her breasts heaving in them.

"Why'd you stop?" asks Emily out of breath.

"Sorry, I'm just stunned that I'm actually looking at your perfect breasts."

"Oh you..." giggles Emily.

"No really, they are perfect."

"Thanks," she giggles again, "can I see you?"

"Yeah of course," he says while taking his shirt off. He has a very lean body and the outlines of a six pack set of abs show. Jack is already sweating lightly already so his hairless skin has shiny tone in the dim light.

"Oh wow!!!" Beams Emily, "You look fantastic!!!"

"Thanks," he says shyly with a smile. She leans up to kiss him and the two start making out again, this time with more lust. Jack has a hard time keeping his member from showing too much in his jeans and hopes that Emily doesn't notice it. Emily brushes up and down Jack's legs and thighs and does feel the tall tale signs of his arousal. She giggles to herself but quickly loses that as the heat of the moment is too intense.

Emily snaps back to reality, in the heat of the moment! She pushes Jack away and he looks at her confused, "What's wrong?"

"I need to tell you something," she says worriedly.

"Okay, what is it babe?"

"You... you love me right?"

"Yes, more than anything in the world, I love you with the bottom of my heart."

"I love you too, but you need to know..."

"Yeah?" he asks naively.

"I... I haven't been totally honest with you..." she says with tears welling up in her eyes.

"What do you mean, I know everything about you. And I love you, everything about you. The way you always make everything nice and tidy – OCD – you always show your love for me. And honestly you're the only girl I've been able to really even talk to; you're so down to earth and loving. You're the most loving person I know, Emily. So what is it?"

Tears start pouring from her eyes as she contemplates on what to say and do. "Okay... I need to show you..." Emily gets off the bed and walks away a bit and gathers her courage. She stands there with her back to Jack as she thinks about the next few moments. "You really love me? No matter what?"

"Yes Em, I absolutely love you! I'd do anything for you!"

"Okay..." she turns around and shows her teary face. Her light make up is a complete mess and she grabs her tight fitting jeans. She unbuttons them and then unzips them. She wiggles herself out of her jeans and pushes them to her ankles before stepping out. Jack smiles seeing Emily's white cotton panties with cute red hearts on them. He also can't believe the sight, her hips are gorgeous, the perfect flare to her body. He is still completely puzzled as to why Emily is so afraid and hurt.

Emily sighs and unhinges her bra, letting it fall to the floor, exposing her cute perky B-cup breasts. Jack smiles again at her beauty but stays still and continues to watch his girlfriend. Sighing one more time, Emily grabs hold of the elastic of her cotton panties and bends over to pull them off. She bends all the way over taking her panties all the way down to her ankles before staying there and looking up, "do you love me?" she says with tears.

"Yes Emily, I love you with all my heart."

Emily keeps her gaze on Jack as she slowly raises herself from the waist. Little by little Jack sees Emily's gorgeous legs until he ends up looking at her crotch. Still completely baffled by Emily's behavior, Jack looks at Emily's crotch. It is completely smooth with no hair. The next thing Emily does is what shocks Jack. Emily spreads her legs just a bit and out pops a tiny cock and balls! He is absolutely surprised by the tiny cock and rather medium sized balls hanging between Emily's legs. She is obviously aroused, but her small cock stands no more than 2 inches when erect.

"I-I don't... I don't understand..."

"I'm not really a girl..." Emily says with sobs of tears, "I used to be a boy, but never felt like one. I always felt like a girl..." Emily hangs her head in shame and continues to cry, unobstructed now. Jack sits on Emily's bed contemplating what happened in the past couple of minutes and can't believe his eyes. One of the prettiest girls in school has a penis! Neither of them say anything for five minutes so there is an unbelievably awkward silence except for Emily's crying.

Jack finally comes to his senses and rises from the bed. He gingerly walks over to his naked girlfriend, but she isn't sure what might happen so she starts to back away, afraid for her life.

"No wait," Jack says non-threateningly.

"You're not going to hurt me are you?"

"No of course not!" he says, "I l-lo-love you..." he can't believe he's saying this to, who he always thought was a girl.

"You're not?" she asks tentatively.

"No babe, I won't hurt you. Now come here," he says with open arms. Emily stands there with tears starting to fade away but hesitates for a moment before Jack gestures again for a hug.

"It's okay; I promise I won't hurt you... I'm just really confused that's all." Emily reluctantly embraces Jack and swings her arms around her boyfriend and hugs him with all her heart. Jack soothingly rubs his arms on Emily's back as she begins to sob again. He can feel her little erection against his pant leg and wonders to himself what he's doing. Jack holds her and brings her back to the bed. He sits down and she stays in his arms on his lap. The two quietly talk about how this all came to be.

After nearly an hour of talking, Jack understands why Emily was previously so shy about the physical aspect of their relationship. He accepts her rather quickly, he even surprises himself, and doesn't let go of her the entire time.

"So that's why I am the way I am..." ends Emily.

"So... um... does it work?" he asks uncertainly.

"Yes, it works. Like I said, even though it stopped growing, it still functions normally," she explains.

"Uh... one more thing..."

"Yeah?" she asks. Jack doesn't hesitate now and plants a passionate kiss on Emily's lips. During the hour long talk, they didn't kiss. Actually now that Emily thinks about it, they didn't kiss since she revealed herself. She pulls away, "so you're okay with this?"

"I think so; it'll take some getting used to. But I love you and this doesn't change anything about me or you." Emily kisses him again and pushes him onto his back on the bed. Just as before they ran into this new revelation, the young couple passionately make out on Emily's bed.

Before Jack knows what's happening he can feel Emily's hands all over his jeans and fumbling for his belt and zipper. "Wait, are you sure?" he asks.

"Oh yeah, I've been wanting to do this ever since I first laid eyes on you..." she moans. With that, Emily has Jack in his boxer shorts with an obvious bulge at the front. Emily pulls away from their make out session and makes her way down Jack's body, eventually settling at his boxer shorts. She gingerly puts her fingers inside the elastic and slowly pulls them down. She slides his shorts all the way off and is rewarded with a modest 6 inch erect dick. "Oh my! You're so big!" she praises.

Without any hesitation she engulfs her mouth over Jack's erect specimen and starts bobbing her head up and down. Emily does this for a short while before pulling off with a loud slurp, "I've wanted to do this forever too."

"Oh Emily, you're so good, that feels amazing!" Jack moans.

"There's something else I want to do..." she smiles shyly.

"Yeah, what is it?"

"Well... I'm a virgin..."

"Oh really?" Jack asks having a faint idea as to what Emily is referring to, "Are you sure?"

"Yes, I want you to make a woman out of me!" Emily giggles. Jack doesn't say anything, but gets up from the bed and switches places with Emily. She lies on her back and spreads her legs, exposing her tiny erect cock. "Take me Jack!" she moans. Jack doesn't need to be told twice so he scoots forward in between Emily's legs. He raises them to his shoulders, on either side, and he is rewarded with Emily's puckered asshole. He marvels at the pink button and takes his cock in one hand and guides it to her most private of places. Emily looks up into Jack's eyes, "Please be gentle."

"I will sweetie, I would never hurt you," he says lovingly. With that he nestles his cock to her puckered hole and begins to push. There's a lot of resistance and Emily tries her best to relax. After some gentle pushing Jack finally enters her. She gasps in pain at first, "Oh my god!!!"

"Are you okay?"

"Yeah, it just hurt at first, it's better now," she smiles. Jack slowly pushes more of his meat into Emily's virgin asshole. Her asshole grips him so tightly he feels like she might squeeze him off. Emily groans and moans as Jack pushes his entire length into her. Jack positions himself above his girlfriend and is amazed at the spectacle of the warm sensation surrounding his cock and looks down. He sees that Emily is throbbing as well, droplets of precum oozing out of her tiny little cock. He bends down and kisses her passionately on the lips and pulls out gently. She can't help herself from moaning from the amazing feeling of being so full. "Oooohhhhh, Jack!!!"

Jack pulls nearly all the way out before pushing in gently again. He does this for about five minutes before Emily ushers him on, "Please take me Jack, fuck me," she whispers. Jack does as he's told and starts to increase his pace. "I'm not hurting you, am I?"

"No Jack, you're being great!" she beams, "Now please fuck me! Fuck me like you want to. Make me your woman!" Jack quickens his pace again and he's having a hard time suppressing his climax. He stares into Emily's eyes when he notices her hand wander towards her cock. He watches as Emily begins stroking herself, at first slowly but then he sees that she soon changes that and strokes furiously. Taking his cue, he thrusts into her with more meaning. "Ooooohhhhh JACK!!!!!" she moans.

"Yeah baby," he groans.

"Oh fuck Jack!! Fuck! Fuck!! FUCK!!!!!" Jack's breathing becomes irregular and he notices that Emily's is as well. "Oh Jack!!!!! I'M CUMMING!!!!!!!!" moans Emily. Jack looks down to see his girlfriend rubbing her tiny cock madly and ropes of cum explode out of her. Three shots explode out of Emily before he let's go as well. He shoots ropes of semen deep into Emily's bowels. He watches Emily shoot out two more loads of cum onto her belly before she's spent. Jack's orgasm subsides as well but he stays inside her for a moment. He leans down to kiss his girlfriend, "I love you Em."

"I love you too Jack," Emily pants. Jack pulls out his softening cock and rolls over onto the bed. Both lovers lie there panting heavily after their love making.

"That was incredible!" exclaims Emily.

"Yeah? It was," pants Jack. Emily leans onto her side facing Jack and grabs hold of his flaccid dick. She starts jerking it slowly.

"You wanna go again?" asks Jack.

"Of course!" she giggles.

Jack starts laughing, "Okay, but you're going to have to give me a sec." Emily continues to play with Jack's cock trying to usher it back to life.

After a few minutes of gentle jerking, Emily's able to get Jack up and running again. Before starting again, Emily takes Jacks manhood in her mouth and gently coats it with her saliva. She licks and kisses Jack's member before she gets on her back again. Jack understands this and whips around so they are in missionary style again. Emily beams the whole time as she pulls her legs up to her breasts and presents herself to her lover. "Take me again!" She begs, "I want you to fill me up with your love!"

Jack smiles down at his lover and willingly obliges as he takes his cock again and aims at her innocent rosebud. With his semen oozing out of her, he presses his cock to her pink little hole, holding it there for a moment. He looks into her eyes, "I love you so much!" he whispers.

"I love you too! Now fuck me like I'm a slut!" Emily says this as she strokes her little hardon. With that, Jack pushes himself into her. As before Emily can't open up right away but Jack keeps going at it until his cock slides into her tight asshole. Emily gasps in absolute pleasure as Jack's warm cock enters her inviting hole. In no time Jack presses all the way into her. His pubic hair gently tickles Emily's bare ball sack. "Give it to me!" she hisses.

Jack pulls out and pushes in gently a few times before he quickens his tempo dramatically, pounding his lover's anal canal with little mercy. Emily yelps out in the sudden change and begs for more, "Fuck me!!!" Jack keeps pounding her and pounding her.

"Oh my god! Oh my god!!! OH MY GGGGGOOODDDDD!!!!!!" Emily screams, "DON'T STOP!!!!!!" Jack doesn't intend to and keeps giving her everything he has. Within a few more minutes Emily whimpers for release, "FUCK!!!! I-I'm C-CUMMING!!!!!!" Jack looks down at Emily's little cock and sees that she's spurting her thick seed all over her flat belly. He watches her shoot out four thick ropes of cum before she finishes with a few little spurts oozing out. Jack isn't finished and keeps pounding her until he finally cums a few minutes later. He moans out in pleasure and erupts his load deep into Emily's hot bowels. Emily smiles as she feels a warm burst of goo gush into her love canal and sighs contently as Jack slows his thrusts and eventually pulls out.

Emily plays with her semen, spreading it all over her belly before licking her fingers clean. She loves her juices and often drinks her own cum when she masturbates on her own. Jack rolls over onto his back again next to Emily completely exhausted. "That was even better!" he pants.

"I know!" giggles Emily still feeling quite horny despite being nearly spent. With the left over cum she coats her hand and gently rubs herself trying to bring her cock back to life again. The two lovers lie there panting for a few moments before Emily sits up.

She starts tentatively, "Um... Jack?"

"Yeah babe?" He leans on one shoulder looking at her.

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byf1dude_lotus© 6 comments/ 65606 views/ 29 favorites

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