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.”
My brother sat on the edge of my bed and worked the hosiery over his feet and up the calves of his legs. When they were at the knees he stood and struggled to pull them higher. I was smiling at his feeble attempts to pull them up when he looked at me exasperated, “Fuck, if getting dressed like a girl is this hard, I’m glad I got something hanging. Fuck!”
I stepped closer, pulled the skirt up and grabbed the top of the nylon then stretched and tugged until it came up, over his ass and around his waist. They were tight so I looked at his crotch to see how they fit; his bulge was flattened considerably against his groin. “Where did your nuts go, between your legs?”
He bent his head to look under the skirt which I was still holding high “Donno, they don’t hurt.”
The next thing I did shocked me even as I did it. I reached between my brother’s legs and felt for his prick and balls. I rubbed the front of the panty hose over the compressed lump of his cock then held his compacted nuts in my hand. Carl jerked and sipped a breath which made me look into his made-up eyes. “Holy fuck Gwen, you can do that again!”
So I did. I squeezed his balls and rubbed the palm of my hand over his prick and said “That’s what it feels like to be a girl on a date.” I looked at the panty hose again “But next time you wear panty hose take the underwear off first. You got too much protection; a guy can’t get a good feel that way.” I dropped the dress; it fell almost to his knees.
“Won’t be a next time.”
“Oh come on bro, I’m having fun, your aren’t?” For some reason I was feeling bold as hell so I rubbed on the outline of his cock through the dress material again “I’d like to see this behind nylon but without the fucking underwear. You can’t deprive me of that can you” I flirted coyly?
My brother studied my face for a long few seconds then said “Help me out of all this, I gotta go see Yvonne.”
“Can I take your picture first?”
“Fuck you bitch! No fucking way!” I only smiled, I didn’t think he would let me but I had to ask. Playtime was over. I cleaned his face, he changed from the dress then went his way and I went mine, neither of us mentioned my brother’s cross-dressing.
Two months later Carl came to me “Hey, I want to dress like a fucking whore. Brad is throwing a costume party; I bet I could win the Skullcandy headphones if you help me.”
“A fucking whore? Man, when you say it like that it sounds totally disgusting. We can fix you up but you gotta think ‘wholesome’ not ‘dirty’. We can make you a beauty queen and you can act the whore if you want.”
Carl’s smiled so big I could count all 32 teeth “Yeah, that’d be awesome.”
Since my brother is five inches taller and 60 pounds heavier than me my clothes were not an option. We went to a local thrift shop to buy his costume. We walked out with a black satin semi-formal gown, size 12 pumps with one inch heels and a bra that would stretch around his chest, D cup. It was going to take a lot of foam peanuts to fill my brother’s tits. He also found a ratty old blonde wig but with a little care and cleaning it would be good enough under the dim lights at the party.
I washed the wig then mounted it over a volley ball and set it. Leaving the fake hair to cure I carefully laid out the rest of the clothing then planned the makeup. By the afternoon of the party I had a clear picture in my mind what Carl would look like; I liked the picture, he would be a pretty woman. I had to keep my humor in check because I could only think of how shocked he would be if some guy made a real fucking pass at him.
“You gotta shave close today, you gonna shave your legs too?”
“Hell no, not my legs!”
“That’s okay, that’s why we bought the black panty hose. Not only will they look sexy with the black dress and shoes, your hairy Russian woman legs won’t give you away.” Carl laughed easily at my dig on his legs.
I started on his face and by the end of an hour it was hard to see the masculine features. As I did the first time, I used eyeliner to bring out his gorgeous blues then make up tones that highlighted the natural tan of his skin. I finished him off with stunning red lip gloss. After he was done we started on the clothes. He wasn’t wearing a shirt, I had him take that off before I started the makeup so he stood and stripped his Dockers to the floor, in seconds Carl was standing in front of me wearing only a pair of those body hugging, thigh length briefs. For the first time in my life my brother caused my tummy to do a little flop. I liked what I was looking at.
We started with the bra; I’d found some foam rubber in the garage and cut two pieces to fit the cups. He put the fake breasts on and after I adjusted them for fit he ogled himself in the mirror. His smile was priceless and I had to ask “Can I please, pleeeezze take some pictures, this is gonna be something to remember?”
My brother hesitated, frowned then said “What the fuck, this is just a costume, okay;” he paused, “man, these tits are huge!”
I snapped four pics on my IPhone then told him to put on the nylons. Carl sat on the edge of my bed and pulled on the black L’eggs panty hose. When he stood to lift them over his ass and body I had to stop him “Hey, you gotta take off the underpants. They are way too bulky for a smooth fit; they will totally show through the dress.”
He stopped and looked up at me “Off, like nothing on under my skirt but nylon?”
“Take the nylons off.” I dashed to my dresser then snatched up a pair of full body panties, made to keep panty lines and bulges from showing around the legs and groin “Put these on, they’ll hold you tight and won’t show through the dress.”
“You’re fucking kidding right? I should wear a pair of your panties? What the hell?”
“Fuck it Carl, you going to let some guy feel you up? No, so nobody will know and the dress will hang better.”
My older brother stared hard at me for a long time, I thought he was going to stop the whole dress up thing but then his face softened slightly “Turn around bitch, I’ll change.”
Emboldened by his acquiescence and what he had let me do to him so far I challenged “Change them, I’m not turning around.”