Dream Daddy- Collection of oneshots

The Crossdressing King |Robert x Crossderssing! Male! Reader

Art by moosopp on tumblr. Seriously, their fan art is amazing! Go check them out on tumblr

Requested by @VivianTon3 I hope this is what you wanted! ❤️
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You were a crossdresser. It was easy for you, seeing as you have a smaller stature than the other dads, and you had more feminine looks and a lighter voice. The only ones who knew you were cross dressing was of course your daughter Amanda, and Mary. Mary found out when you went bar hopping, and got drunk. She fully accepted you, and was even a little jealous that you looked so damn good as a woman. You also drunkly expressed your love for Robert. You absolutely loved everything about Robert, his mysterious demeanor, his steely eyes, that wonderful smirk he wore whenever he saw you. You've hung out with Robert many times, bar hopping, cryptic hunting, and even going to the cinema. You didn't want him to find out the ugly truth, mostly because you were self conscious about how you looked as a man, small and feminine. But as a woman, you were confident, free to dress how you wanted, and you looked good. You wanted Robert to know, but you were nervous. You wanted to tell him tonight, seeing as he asked you to go to his special thinking place. Something about him needing to tell you something important.

You decide to throw on normal clothes, a simple t-shirt, jacket, and ripped jeans. You put your makeup and wig on, and decide to text Robert that you were ready. You wait on your couch, anxious as hell. You think of how to tell him...you hope he won't think of you as a weirdo. Amanda pops out of her room, coming over to you. "Lookin good, popsicle." She says "Goin on another date with Robert?" She sits next to you. "It's not a date, Manda" you say, obviously in distress "We're hanging out at his special thinking place, and he has to tell me something! I've decided to stop hiding, and show him who I really am. But I'm scared Amanda, what if he thinks I'm some creep? A weirdo? What if he hates me? I'm so nervous.." You drop your head in  your hands, sulking. Amanda sits there stunned by what you said.."Dad...don't be nervous..you're an amazing person, a good father and friend! You're sweet to everyone, and if Robert can't accept you as yourself and see how truly amazing you are, then he doesn't deserve you. But I'm sure he'll love and accept you just as I do" she smiles down at you and pats your back. "Amanda..." you tear up at what your daughter says, and hug her. "Aw dad! Don't cry, you'll  make me cry!" She says hugging you. You both let go and you look at her, determined. "You're right Manda, I'll show him who I really am!" You say, hearing a horn honk. You get up and smile at your daughter. "Wish me luck sweetheart" She smiles and gives you a thumbs up. "Get 'em dad!" You head out the door, and hop in Robert's beat up truck. "Ready  to go (y/n)?" He says smirking. "Let's go!" You guys blast music from your teen days, and sing as loudly as possible and laugh, genuinely Enjoying yourselves. You finally make it to his special thinking spot. You both get out, and Robert helps you onto the hood of his truck. You guys tell stories and he even shows you how to whittle. A sudden silence comes between the two of you. "I need to tell you something" you both say in unison and look at each other. "You go first" Robert says. "Ok" you sigh, nerves building up, butterflies burst around in your stomach. "Close your eyes please" Robert raises an eyebrow, but does as he's told. You pocket the knife and take off your wig. Revealing shiny, (h/c). Pulling out make up wipes out of your bag, you wipe off your makeup. "Ok...you can open your eyes, but you have to promise not to scream" He opens his eyes and gasps "...(y/n)?." His eyes are wide, and mouth agape "Robert, this is who I really am...I've been cross dressing for years now. I'm sorry I didn't tell you sooner, I was scared that you would hate me and think I'm some freak...So. What do you thi-" "Amazing" he cuts you off. "W-what?" He smiles "You pull off both looks: a beautiful woman, and a handsome man." Your eyes widen, and a blush creeps into your cheeks. "Y-You really think so?" "Yes. I know so. I'm so happy you trust me enough to show me the real you, but I've been wanting to tell you something. I like you (y/n), I have for a while. And I want you to know, that I fully accept you this way, and when you dress as a woman. I wanted to ask you if you'd go on a date with me" Your eyes water for the second time today, and you smile brightly at him. "Of course I will!" You squeal and hug him close. "Thank you for understanding me.." He chuckles and holds you close "Of course"

You lay together, Drinking a bottle of whiskey that Robert kept in his truck, and cuddle. You both share many more nights like this. Many dates later, Robert proposes to you, and you could never be happier.

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Oh my gosh, I had fun writing this one 😍 I hope you guys enjoyed this one! Remember, requests are still open!