Carl or Carla

by Mystic47

Caution: This Sex Story contains strong sexual content, including mt/ft, Consensual, Heterosexual, CrossDressing, Fiction, Brother, Sister, .

Desc: Sex Story: A sister helps her brother dress up like a woman for a costume party.

I was sitting on the edge of my vanity talking to my brother, teasing him because he had a big yellow zit on his forehead. “You can’t go out with Yvonne looking like that; you better put a band-aid on your head to hide it.”

“Oh yeah, that’d be real hot, a nice plastic plaster of Ironman over my eye. Or maybe Big Bird, bright yellow.” He looked past my shoulder to the mirror behind me “god, that’s fucking ugly.”

“Why worry about it, the only head she wants to look at isn’t on your shoulders.” I knew Yvonne; she’d been fucking my brother for several months. Carl put his fingers on the pimple and started to pinch it, “Stop, I want to do it” I told him.

He glanced from the mirror to my face “You gonna squeeze my zit?”

“Sure, why not, I do my own, and after I can put some blush or something over it. Hide it with makeup.”

He leaned his head back from me and glared at me intently, “Make up? Like some sort of fucking fagot or something. I ain’t’ gay!”

I grabbed his chin in my hand and held his face still “lots of guys are doing make up now, not like a woman but enough to hide things like the really charming spot on your face. Come on, let me do it for you, I promise you won’t fucking die or anything.”

I hopped off the vanity then reached for the offending blister over his right eye; an angry red volcano with a white pus filled head. I pinched it between my index fingers lightly; it was so ready it erupted, pus forming as a large bubble on the end of my finger. I wiped the mess off with a tissue then told him to sit. Carl inspected his wound in the mirror before he turned and sat on the padded bench. I reached behind him for foundation and blush, as I did my breast rested against his shoulder; he bumped me, putting more pressure on my tit before I moved away. It didn’t bother me that he did that; it wasn’t the first time and it was reflective of the affinity between us. Carl and I talked and joked easily as I applied the camouflage to his face, we bandied words about him going gay and having to give up Yvonne for some guy named Yancy.

“Why Yancy?” he asked.

“Cause Yancy is a gay name, perfect for you.” He laughed and poked me in the ribs, tickling me enough that I fluffed powder over his nose which made him sneeze.

I worked on the red spot for a few minutes, blending the make up into his forehead, matching the colors with his suntanned skin. When I was done he examined my work carefully from up close, his nose almost touching the mirror, to far back for a complete view of his face. “Well, okay, I guess I can live with it. Thanks.”

It was still early, Carl wasn’t going out for a couple more hours and my date was even later so I wanted to have some more fun with my brother. I grabbed a mascara brush then told him “Sit, I’m not done.”

“What the fuck? I’m good, you hid it well, it will be dark and we won’t be staring at the other too much, she closes her eyes when we get it on.”’

“Really? That’s no fun; I like to see who’s got his prick in me. Sit down, let’s play a little, I want to see if you’d be a pretty girl, we got time.”

“You ever put make up on a guy before?”

“I used to paint dad’s toenails when I was little, he wouldn’t let me do his fingers.”

“Ain’t the same.”

“Sure it is, come on; just sit still so I don’t poke your eyes out or something.”

For the next ten minutes I fussed with Carl’s lids and lashes. I painted him up with dark blue liner and pulled the lashes with my black brush. My brother has cobalt eyes and by the time I was done highlighting them with makeup I was intrigued by how deep they looked. Deep, blue and sexy. Yes I thought it, Sexy, my own brothers eyes. When I capped my mascara brush he turned and looked into the mirror “Fuck, that looks weird.”

“No it doesn’t, you have really sexy eyes. You look like a rock star or something.”

I pulled him around again then told him to sit sideways across my bench. When he did I sat on the other end facing him. I grabbed more blush and started on his brow, cheeks and chin. Carl sat quietly while I fussed with the makeup, rubbing, blending, wiping off and starting over with a different shade. He sat still for twenty minutes until I got the look I wanted. I was having fun, I felt like I was doing movie make up for a star or something. The entire time we were talking and the longer we talked the more intimate the conversation got.

“You ever do this with your boyfriends?”


“What do you do with your boyfriends?”

I sat back and looked into his made up eyes “I fuck them, but don’t think I’m some sort slut or something, I don’t have ‘boyfriends’ like a whole stable full of studs.”

“So how big is your stable, how many hard-ons have you sat on?”

“You ask me that again and I’ll be sitting on yours only it won’t be slipping and sliding in me, I’ll sit just long enough to crush it to pulp.”

“Oooo, that sound fun, let’s try it.”

“Stop talking or you’ll smear the lip gloss.”

“I fucked nine girls” he announced as if I cared.

“You’re still talking.”

He quit moving his lips to let me paint them. While I was focused on his mouth my mind was running names through my head. Nine. I knew five but the other four were the next question for Carl. “Okay, Ilene, Margo, Belinda, Cassie and Yvonne. Who else, do I know them?”

He smiled, giving me glimpse of a corner of his lip I needed to touch up. “Diane, Sally, Randi and Shonda.”

“Shonda? She’s a black girl!”

“Yeah, a fucking hot black girl, sex with her was like screwing a volcano. Didn’t you do a black guy?”

“No and I don’t know if I would, none have asked me out so I never got the chance to say yes or no.”

I was done. I got off the bench and looked down on my brother and decided he would be a pretty woman. “Take a look; you’re kind of appealing that way.”

He looked at himself critically, “Appealing for who, Yancy or Yvonne?”

I wasn’t’ ready to stop “Yancy is gay, Yvonne is a girl, let’s see if we can make you appeal to a straight guy, somebody I’d fuck.”

He looked at me warily “What do you mean?”

I went to my closet and pulled out a dress that was too large for me, “Put this on, I want you to dress like me.”

Carl turned red, his eyes widened in disbelief, “What,” he squeaked, “you want me to dress like a fucking bitch now?”

I grabbed his shirt and started opening the buttons, “Come on Carl, we’re having fun, this will never leave my bedroom. I promise.”

He hesitated for a long moment, I thought he was going to flee my insanity but his eyes relaxed then he pulled the open shirt off his wide shoulders and dropped it to the floor. As he picked up the dress I had another flash “Stop, not yet!” I pulled open my underwear drawer and pulled out a black lacy bra. “This first.”

Again he stopped cold and stared at me the muttered “You ever tell anybody about this I’ll fuck you up forever.”

To my unbounded delight he took the bra and slipped it up his arms. I went behind him to clasp the strap then moved to his front again. The C cups were stretched flat because of his broad back and chest, he was looking at his profile in the mirror, “Hmm, I’m not impressed.” I grabbed a pair of nylons and handed them to him. “Stuff these in there, that will help.”

“You stuff them, putting this on was bad enough.” I gleefully filled the flat boob holder until it looked like he had a pair of tits standing proud from his chest. He checked the mirror again, “Okay, better, almost a handful now.”

I stood back as Carl picked up the dress and held it out to look at it. He dropped the dress on my bed then opened his jeans, pulled them down then stepped out of them one leg at a time. He surprised me because I couldn’t remember the last time I’d seen him in only underwear, if ever. He was wearing snug thigh length briefs that formed tightly around his cock and balls giving me a sharp relief view of his works. I startled myself by thinking that just maybe Yvonne and the others enjoyed that a lot. He picked up the dress again and started to step a foot into the neck.

“No, over your head. Pull it down from the top otherwise you won’t get your arms though the sleeves.” Carl lifted the garment, held his arms high and let my pale yellow summer dress slip down his body. He put his arms into the short sleeves then turned to look at me as it settled on his shoulders. “Turn around.”

I managed to pull the zipper up to its top then put my hands on his hips to turn him to me. When I stepped back to look at my made-up, dressed up brother I began to laugh. He looked at his image in the mirror and started laughing with me. The dress was tight around him, his brand new tits were lopsided and he’d smeared his makeup but none of that mattered, we weren’t looking for a beauty queen.

As I looked him up and down I sniggered, “Man, you got fucking ugly woman legs, maybe in Russia are the girls so hairy.”

He lifted the skirt and looked down and started chuckling with me then asked “Got some panty hose? Maybe that will make them look better.”

I rummaged in my dresser for a pair of dark panty hose and handed them to him. He looked at the wad of nylon, “Those are supposed to fit you? They’re all fucking shriveled up!”

“They’ll stretch, if they were bigger they’d be like baggy and loose. Put ‘em on.”

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Story tagged with:
mt/ft / Consensual / Heterosexual / CrossDressing / Fiction / Brother / Sister /