PROMPT: Nick thinks Jeff is cheating on him with a girl because he keeps finding girl clothing around Jeff's room. Half way through the fight Jeff finally breaks down and admits to Nick that he's transgender and wears female clothes when he's not with Nick. Nick accepts him and they go on their first date as Nick and Jenn.

(A.N:/ Ah! I love this idea! Just sdwr5tw5ywqa everything about this idea! But, before I start this I've never written for a transgendered character before…I've only done cross dresser so I'll try my best but it might not be all that good. But I hope I do it justice. This is actually kind of ironic because right now I'm watching The Christine Jorgensen Story…I also know this doesn't really count as crossdressing!Jeff but I'm putting it in the tag because it's the one that makes the most sense to put it in…Anyway, hope you enjoy.)


"Hey Nicky." Jeff said, answering his phone.

"Hey Jeff, I'm here." Nick said, standing outside of Jeff's house.

Jeff chuckled. "Dude, just come in. You practically live here. I'm about to hop in the shower really quickly though, alright? So just wait up in my room." Jeff said and Nick could hear the water starting to run in the background.

"Alright, see ya." Nick said, hanging up with phone and walking in Jeff's house. He walked into Jeff's room, as usual, and sat on his bed, looking around the messy room. Nick sighed a little at how messy his boyfriend was and got up to tidy up a little. Nick began picking up Jeff's dirty clothes from his floor but quickly stopped when he picked up a pink bra. "What the…" Nick mumbled to himself before it finally hit him what was going on. Jeff had a bra in his room. A bra in his room. Nick's eyes widened and he threw the bra back on the floor, throwing the clothes he had picked up on top of it. The water in the other room turned off and Nick quickly ran back over to the bed.

A few minutes later Jeff came out of the bathroom wearing only shorts and a towel hung around his neck. He smiled brightly at Nick. "Hey Nicky." Jeff said, leaning over to kiss his boyfriend. Nick didn't kiss him back and Jeff pulled away with a confused look on his face. "Are you alright?" Jeff asked, frowning a little.

"I'm fine." Nick said, shortly.

"Is my breath bad or something?" Jeff asked, putting his hand to his face and breathing out to try and smell his own breath. Jeff sat down next to Nick and frowned a little, trying his best to read Nick's facial expression.

"I…I have to go." Nick said, getting up.

Jeff quickly grabbed his hand. "Wait, what's wrong? You're starting to freak me out."

"I'm fine. I just need to leave." Nick said, pulling away from Jeff and quickly leaving the room.

When Nick got home he noticed that he had twenty texts from Jeff and a voicemail. He sighed a little as he listened to it.

"Hey Nick, it's Jeff…but you know that. I uh…Look, you just ran out of my house and you looked upset. Like really upset and I'm worried about you. Are you alright? If you don't want to talk about it then that's fine, I'm not going to push you or anything but if you do you can call me and I'll drop everything to talk…I uh…if I did something I'm really sorry. Just…I…I don't know, I'm just worried about you. If anything, please just tell me you're still alive, you turned out of my driveway so fast I thought you were gonna flip your car…I love you Nicky."

Nick sighed loudly when he finished the voicemail. Right now he wanted nothing more than to be alone with his thoughts. Nick knew Jeff, he was not going to leave him be. Nick's phone began ringing again and Nick threw his phone across the room onto a chair and flopped down, face first, on his bed. His phone quit buzzing for a few moments but soon began again. It quit again then buzzed again a few more times. Nick was trying to make sense of why Jeff would have a bra in his room and then it dawned on him. Jeff had a sister.

Nick heard knocking on his front door. Nick got up and ran to the door before his mom could get to it. He went outside and looked up at Jeff who had a worried look on his face.

"You weren't answering your phone…I was worried." Jeff said, kicking at the ground lightly.

"I know, sorry. I'm fine, promise. I just felt sick suddenly and thought barfing in front of you would make the sexiness of our relationship go away." Nick lied.

Jeff let out a huge sigh of relief. "Oh, thank God! I was seriously worried about you! So you're better now, right?"

Nick smiled brightly at Jeff and nodded. "Yeah, I'm fine. I'm really sorry about before."

"Then you wanna come back to my place?" Jeff asked. "My parents are gone for the weekend." He said, smirking a little.

Nick smiled a little. "Yeah, alright." He said, taking Jeff's hand and leading him towards Jeff's car.

About twenty minutes later the two were laying on Jeff's bed, Jeff on top, making out. Jeff moved his lips from Nick's lips to his neck, lightly biting down.

Nick moved his head back to give Jeff more space and that was when he saw it. On Jeff's nightstand there was glittery makeup and women's underwear. The kind that slutty girls wore; the kind that Jeff's sister would never wear.

"Wait, stop." Nick said, wiggling around to get away from Jeff.

"What?" Jeff asked, confused.

"Are you cheating on me?" Nick asked, bluntly.

Jeff gasped a little. "What?" Jeff said, jumping off his bed. Nick got up as well. "Nicky I would nev-"

"Then why do you have a bunch of girl things around your room? Like these!" Nick asked, grabbing the black frilly panties from Jeff's nightstand and throwing them at Jeff.

Jeff bit his lip. "Nick I…I'm not cheating on you. I…"

"You what? Cheating on me with some slutty girl! I thought you loved me Jeff I-"

"I do love you!" Jeff yelled.

"Then why would you cheat on me with some girl who wears slutty underwear and whorish makeup! A girl Jeff! I could maybe understand a guy since you're gay but a girl? Seriously? That just makes it worse! Was our entire relationship a lie then? I thought you loved me!" Nick yelled.

"No! Nick I do love you! And I'm not cheating! I…I just can't explain this Nicky…not right now…please I-"

"No!" Nick yelled. "There is no other explanation other then you're cheating on me and obviously don't have the decency to admit it!"

"No Nick, it isn't that, I swear! Just…I can't right now. Please, I'm not cheating on you. I'm in love with you. Please, I'm not ready. I…I love you." Jeff said, in a pleading tone.

Nick began rifling around Jeff's room.

"What are you doing?" Jeff asked, confused.

"Looking for more of your slutty girlfriends clothes!"

"I don't have a girlfriend Nick! And I'm not cheating on you! Please! Just believe me!"

"Don't even try to lie to me Jeff! I caught you! Just give it up!"

"I'm not lying!" Jeff yelled, tears in his eyes.

"Then why the fucking hell do you have these? Huh! If you aren't cheating then who's are they!" Nick yelled.

"They're mine!" Jeff yelled, clasping his mouth shut the second he realized what he was saying. His tears were falling freely now. He hadn't meant to say anything but Nick was yelling and Jeff had always been horrible under pressure.

Nick's eyes widened. "You…what?" Nick asked, completely confused.

Jeff took a deep breath and did his best to calm himself. "I…they're mine. The clothes are mine…I…Nick, I'm…I uh…I'm not gay Nick…I like guys, don't get me wrong, and I love you, it's just…it's complicated."

Nick wrapped his arms around Jeff and let the blond cry on his shoulders, still confused but completely sure Jeff wasn't cheating on him. "Jeff, I-I'm so sorry. I…You shouldn't have had to tell me. Not like this. I shouldn't have pushed you, I'm so sorry. I'm so freakin' sorry Jeff." Nick said, feeling absolutely horrible. "I get it, you love me as a friend and you dated me because you felt bad…You're straight…" Nick said, his heart sinking.

"N-no! Nicky, I do love you! I'm in love with you! I am straight though…it's just…Nick, I'm a girl." Jeff said, actually feeling a little better just by telling Nick. He had wanted to tell Nick for months but he just wasn't ready to. Jeff was afraid Nick would freak out and want to break break up, or worse, never want to speak again.

Nick pulled apart and looked at Jeff, confused. "Jeff…you're a boy…you have a penis. I've seen it, many times…" Nick said, awkwardly.

Jeff shook his head and bit his lip. "You…I didn't want to tell you because you wouldn't understand…"

"Then explain…Please?" Nick asked.

"I was born with a guys body but I'm not. I'm a girl…I think of myself as a girl. It's how I identify myself…I just…have the wrong body. It's hard to explain but I uh…I wear dresses, and wigs, and other girl things when we're not together. My therapist says I'm a girl trapped in the wrong body. And I know you have a lot of questions so go ahead and ask but please, please don't hate me because of this…I was afraid to tell you because you're gay and I…if I told you, you wouldn't want to be my boyfriend…I'm sorry, it was selfish…and I was…afraid. I was really afraid…aside from my therapist and parents, no one else knows."

There was a long silence between the two before Nick finally spoke. "What's your name?" Nick asked, quietly.

"What?"

"Your name. Jeff isn't a girl name. What's your name?"

"Jenn…" Jeff said, awkwardly.

Nick instantly burst into laughter and Jeff looked at Nick, completely shocked and a little frightened that his possibly ex-boyfriend was having a mental breakdown at the news.

Nick held his hands up. "Sorry, sorry, I know this is a horrible time to laugh. It's just…Jenn? You changed two letters! Alright, sorry, sorry, I know I shouldn't laugh. I know this is serious. But Jeff, I…Thank you for telling me. I know you didn't want to today but…just thank you. I…I love you, Jeff. Nothing is going to change that. I wouldn't care if you were an axe wielding serial killer! Okay yeah, that was a bad example. My point is, I love you and if you're a girl then that's alright. As long as you're happy and healthy, I don't care what you are."

"S-so you don't mind?" Jeff asked, shocked.

Nick smiled and kissed Jeff's cheek. "Of course I don't." He shrugged a little. "If anything I think my dad will be really happy. He's always wanted me to date a girl." Nick said.

Jeff chuckled a little. "'m telling you my biggest secret and you're making light of it!"

Nick shrugged. "You know me…But, honestly, I really am happy you told me…I love you Jeff and I know we have a lot to talk about still but just know that I'll support you no matter what. Whether you get surgery or whatever or not…I'm not really sure of the whole process…but I'll support and love you no matter what. Promise."

Jeff started crying again. "Sorry, I'm just really relieved."

"How…uh…how long have you known? If that's alright for me to ask…"

"I guess I've always kind of known…but I didn't really fully realize it until about five months ago. I've been going to therapy about it and I do plan on having gender reassignment surgery, though I'm not sure when. There are a lot of things I have to do before I even can…but I do want it. It's…it's really fucking horrible waking up everyday in the wrong body…Are you sure you're alright with all this Nick? I mean, for one thing this is a lot to take in and…you're gay."

"Honestly, I've never had a crush on another guy before. Just you, and I've never liked any girls before so when I realized I was in love with you I just assumed I was gay…I honestly don't know what I am…but if you're a girl I guess that would make me straight maybe?" Nick said, beginning to confuse himself.

Jeff gave Nick a weak smile. "I think you're just Jeff-sexual."

Nick rolled his eyes. "You're so conceited."

"You love me." Jeff said, chuckling.

"Hey Jeff?"

"Yeah?"

"Can I…uh meet Jenn?" Nick asked, a little awkwardly.

Jeff's eyebrows went up a little. "O-oh…uh yeah, sure! Of course. I need like two, three hours though…I'm still getting used to the whole dressing up stuff…Oh, and Nick?"

"Yeah?"

Jeff frowned. "Thanks for calling my underwear slutty." He said, sarcastically.

Nick rolled his eyes. "Whatever. Just hurry up…I kinda really wanna see if my girlfriend is hot or not…"

Jeff gasped a little. "Nick!"

"I'm kidding! You'd be beautiful in anything! Whether it's a dress or a giant sack. Now, go!"

"Fine, fine." Jeff said. "All my stuff is in the bathroom so…And no, you can't watch so don't even bother asking." Jeff said, going towards the bathroom.

About two in a half hours later Jeff walked out of the bathroom and Nick gasped. "Holy shit." Nick said, wide eyed.

Jenn frowned, feeling self-conscious. "It isn't that bad…is it?"

"What? No! You look really hot." Nick said, looking Jenn up and down.

Jenn had on a blond, slightly wavy wig that almost reached her shoulders. She wore a tight, short, red dress that showed off her long legs and hip pads that she wore to make herslef look more feminine. The dress was strapless and showed off Jenn's fake breasts. She wore six inch heels that were black and matched the small purse she was carrying. Her makeup was subtle and looked almost natural.

Nick laughed. "Of course you would choose to have giant boobs!"

Jenn chuckled. "Damn straight! Having boobs is awesome and aren't you the one who always says go big or go home?"

Nick rolled his eyes playfully. "Yeah yeah, whatever…you know you look like a girl…a really tall girl. Take the heels off. You're already taller than me…"

Jenn kicked off her shoes and put on a pair of black flats. "Better?"

Nick nodded. "Much…So…have you ever gone out like that? As Jeff?"

"I have, yes. So far it's only been to places I knew no one would recognize me at…and I've gone to a few therapy sessions as Jenn."

"So you wanna grab lunch at Breadstix?" Nick asked, casually.

Jenn's eyes widened. "W-what! No, Nicky we know people there. I…I'm not really a hundred percent comfortable with all this…It's still really new to me and right now I don't want anyone else knowing…Maybe someone else?"

Nick smiled. "Sure, we can go somewhere else. I don't care, I just want to go grab some lunch with my girlfriend."

Jenn smiled and kissed Nick lightly on the lips. "I love you."

"I love you too."


(A.N:/ Holy shit, I didn't think this would end up this long…Anyway, hope you guys enjoyed! It was really interesting to write. Thanks for reading!)