Ladies Night

"Come on Morgan, we're all going in dresses tonight. The sign clearly says chicks drinks free," Mike said.

Mike had been my best friend since elementary school. He always had crazy ideas that made me question my sanity but... he was never wrong, we always had fun when he set something up like that.

"It's gonna be way too weird, like how are we gonna pick up on girls if we are all wearing dresses," I asked.

"Not just dresses Dude, wigs and makeup too, and chicks dig confident guys. I guarantee you get laid tonight. Don't you trust me... remember the toga party? I seem to remember you went home with that cute redhead friend of Sadie's," he said.

He was right. I didn't want to wear a toga. I didn't even want to go that night but I ended up dating Christina for almost a year because of that night but I didn't own a dress or a wig... I didn't even know the first thing about getting them either.

"Where the hell am I supposed to get that stuff in just a few hours," I asked.

"Dude, just talk to your sister. I'm getting Lyssa to help me," he said.

"I can't ask Cheryl to do that man, that's weird as shit," I said.

"Whatever dude, you're so lame," he teased.

I knew if I didn't agree, he'd tease me and hound me about how unadventurous I was and how lame people like me never got anywhere in life because I don't take risks. I didn't want to be lame anymore. I was done giving him excuses to tease me. If he wanted to wear a dress to get free drinks at the bar, then by god, we'd wear dresses and drink for free.

"Fine... I'll do it, but if I show up and you're not in a dress I'm gonna be so fucking pissed. I swear to god, you'd better not be fucking with me," I said.

"Nah man, we're all wearing dresses tonight. I wouldn't do that to you," he said.

I only had a few hours to find a wig and a dress so I immediately called the only person I knew with access to both items. My sister Cheryl was a few years older than me and had already graduated college but she still lived in town so I started walking toward her house.

"Hey Cher... so, the guys all want to exploit a loophole at the bar to get free drinks. We're all gonna wear dresses to the bar tonight. Do you have anything I can borrow for a couple hours," I asked over the phone.

"What, you have got to be kidding me. I've heard people joke about that but never actually seen anyone do it. Is this for real or are you just pulling my leg," She asked.

"I'm pretty sure it's serious. Mike said everyone is showing up in a dress tonight."

"Yeah, fuck yeah you can borrow a dress! Hell, give me an hour and I'll make you the hottest femboy that bar will ever see."

"A what... I don't need to be hot, I just need a dress... and maybe a wig. Do you have a wig too," I asked.

"I have everything we're gonna need except you so hurry the hell up! Oh my god, this is gonna be so fun," She said hanging up the phone.

I couldn't believe I'd been talked into wearing a dress to the bar just for free drinks. I had the money to buy my own drinks, I had a great job and my parents paid for school so there wasn't any reason other than my friends were doing it. I paused on the steps to Cheryl's place trying to decide if I really wanted to go through with it or not. I knew as soon as I knocked on the door, there wouldn't be any way in hell I'd be able to back out.

I thought back to the toga party and Christina. I would probably still be a virgin had it not been for that night. Mike was right... his ideas usually did produce the best results so why the hell not.

I knocked and not even two seconds later Cheryl opened the door. She practically pulled me inside and ushered me toward the bathroom.

"Come on bro, let's make you a hottie," She beamed.

"I don't need to be a hottie, I just need to borrow a dress and maybe a wig but really... just a dress would be fine," I argued.

"Bull shit, if we're gonna do something, we might as well do it right. Besides, I talked to Mike, he said a wig and makeup so that's the standard but I don't do shit halfway so it's my way or you can find someone else to help you," she said.

"Fine, but only because there isn't time to find someone else," I said as she pushed me inside the bathroom.

"Strip mister, shower and shave... chop chop, we don't have all day," she shoved a new pink razor into my hand.

I already showered and shaved that morning so it didn't take much to get clean and my facial hair was still pretty short but I whacked the minimal stubble off anyway and stepped out of the shower wrapped in a fuzzy pink bath towel.

"Have a seat, let's get started on your... wait a minute, I thought I told you to shave," she said.

I rubbed my chin to check for any stray hairs but I was certain I'd got them all. "I did shave, twice now today," I quipped.

Yeah, what the hell is this," She said pinching numerous hairs, first on my leg then on my arms.

"Ow, Jesus Cher, that hurts," I cried.

"Get back in there and shave everything dammit, how the hell are you going to wear a dress with hairy arms and legs? It's just not proper," She said.

"Nah, hell no... that's just too much. I agreed to a dress and a wig, not shaving my entire body too. Forget it, they can just go without me. Gimme my clothes back, I'm outta here," I said.

"Sorry bro, you're not getting your clothes back and unless you want to walk all the way across campus in just that fuzzy pink towel, you'll get back in that shower and shave everything," she said.

"God, this is such bull shit. You know the police will pick me up within ten minutes, and I'll be labeled campus pervert" I cussed.

Just before she closed me back in the bathroom she added one final command. "When I say to shave everything, I mean everything... do you understand," she growled.

"Jesus, yeah... everything," I said.

I wasn't exactly sure where to start other than my cock and balls. Christina used to like me shaved down there but just because she thought it made me look bigger, truth was, shaving only helped a little bit and once she left me, I didn't have much of a reason to continue. I made short work of my junk and worked the razor back through my crack and up my back best I could reach. I luckily only had a little hair low on my back.

The real trick was shaving my legs. I just couldn't see everywhere and resorted to making several passes to ensure I got it all. I was just about to step out when I remembered my arm pits. I'd never shaved my arm pits before... I hadn't even seen anyone shave their arm pits either so I had no idea how to do it. I clogged the razor several times as I attempted to clear the last bits of hair from my body. Luckily I finished just as the water went cold and I rinsed in frigid water stepping out shivering.

"I thought you fell asleep in there or something," Cheryl said as I stepped out with the towel wrapped all the way up under my arms for the added warmth.

"God dammed water went cold," I stuttered.

"Lemme see," She said tugging at the towel.

"Fuck, I'm naked under here, you don't want to catch an eye full of my hairless junk do you," I said grabbing my shriveled frozen cock and stone hard balls through the towel.

"You shaved that too, ah ha ha... no one's gonna see that much unless you let one of the drunks at the bar in your panties tonight," She laughed.

"Seriously not funny. No one is picking me up tonight," I said.

"Alright then, take a seat. Lemme put your face on," She said.

Cheryl patted and rubbed my face with so many things I lost track of what she was doing and how much time she'd been doing it. I zoned out playing online poker on my phone and was almost surprised when she flipped a bright pink wig on my head. She spun me around and I could barely believe my eyes. I looked nothing like myself and where I used to be, sat a cute little thing with bright pink party hair.

"What the fuck Cher, I don't even know how that's possible. I thought you were just gonna do a little and give me a wig... I didn't know you were going to make me actually look like a girl. How the hell do I play this off as a joke now. People are going to think I've done this before," I moaned.

"This isn't your first time little brother, do you remember Halloween that year you went to school as a cheer leader," She laughed.

"Yeah, that was the fucking seventh grade, and that was Halloween, not a bar in July," I grumbled.

"Oh get over it, what's done is done, now let's find you some clothes to wear, come on... follow me," She said waltzing toward her room.

I shuffled behind her twisting my head side to side to keep the wig from tickling my shoulders as the hair wafted through the breeze. We stopped in her closet and she tossed a black lace bra at me. I barely caught it as another streak of dark fabric landed on my face. I stuffed the bra under my arm and held the fabric out at arms length.

"Oh fuck that, these are panties... I'm not wearing panties too. Why can't I just wear my boxers. I'm not letting anyone even think they're getting anywhere with me tonight," I growled.

"And if a breeze blows your dress up, everyone is gonna see your ugly ass striped boxers. I'm not having my favorite brother getting laughed at because he is wearing boys underwear to the bar," She smiled.

"Yeah, I'm your only brother and they're gonna laugh at me because I'm wearing your panties. That's just gross... you can't make me, I mean maybe if they were new but fuck that shit," I said feeling triumphant until Cheryl pulled a plastic bag from her drawer. She tugged another pair of panties out of the wrapping and tossed them at me.

"They are brand new, so you'll either wear those pink ones or the black ones," she said.

"Fuck, this is fucking weird. I can't believe I'm letting my sister put me in panties."

"Well, turn around. I'm not doing it with you looking," I said twirling my finger in a circle.

"It's not like I've never seen you without clothes on. I used to bathe you, don't you remember," she said.

"Not since I've... you know what, it doesn't matter. I'm not gonna let you see me naked anyway so turn around already," I growled.

Cheryl turned her back on me and I held the black panties out. They seemed far too small even sliding up my legs but the soft lace managed to cradle my smooth cock and balls in the most erotic way possible. I felt my cock stir to life. The thin fabric nestled partway between my smooth ass cheeks and I couldn't believe how well they fit, or how nice they felt covering my most delicate body parts.

"Oh my god," I moaned.

"Yeah, every guy does that the first time they put those on," Cheryl said.

"What, I thought you said they were new, awe Jesus I've got someone's dirty panties on. Man, you tricked me..." I yelled.

"No, they are new, I promise! No one has worn those panties but you, I promise," She said.

"Well, you said..."

"I meant every guy says something along those lines the very first time they put panties on. Even if they say something like, THIS IS GAY! It's their tone that tells the truth," She said.

"You swear they're new," I asked.

"Yeah, promise... do you like them," She asked.

"They're not bad," I said.

"It sounded like they were better than not bad... I heard, oh my god," She mimicked the exact moaning way I exhaled when I first felt the panties wrap around my balls.

"Yea, they're nice... like just wow," I said rubbing the material through the towel.

"You need help with that," She said pointing to the bra.

"I've taken my fair share of these off, how hard can it be," I said completely underestimating exactly how hard it was to get the clasps hooked up behind my back.

I tried imitating Christina the numerous times I'd witnessed her putting a bra on but I obviously didn't pay close enough attention to the most important parts and Cheryl stepped behind and helped me in the bra. She also pushed two teardrop shaped pads into the cups that filled the bra out more than enough.

"God, is that necessary? Like they're so big... do they have to be that big," I moaned.

"They aren't any bigger than my boobs. Do you think my boobs are too big," She asked.

"God, I don't know. It's not like I sit and judge your boobs all the time," I said unable to look in her direction in fear I'd stare at her boobs.

"We'll look at them, it's not a big deal. They're just boobs," she said.

I slowly turned my head to look at my sisters chest. Her top was low cut and her cleavage was clearly visible. As far as boobs went, they looked about normal, maybe a little bigger than normal but not bad. I felt my already stiffened cock swell just a little more as I wondered if my sisters nipples were like Christina's or not.

"Jesus, I said look at them, not to undress me, god... you're such a pervert," She laughed.

"God, you said look at them. I was just looking. They're nice okay," I said.

"You should see them without a bra on," She said as she squeezed them together and leaned down a bit. "I drink for free every night with these girls," She said.

"Jeez, I don't want to see your boobs... who's the pervert now," I laughed.

"Put those on too," Cheryl said tossing me a small paper box.

I pulled the thin nylon material from the box and held the miniature see through leggings up between us. "These are never going to fit me, I mean, my legs would have to be less than a foot long," I laughed at the absurdity of it all.

"They'll stretch out, trust me. Do you need help or can you manage," She said.

"I can manage," I said retreating to the bedroom to sit on the bed.

I pushed my legs through the holes and started pulling the thin nylon material up my legs and was halted by Cheryl's boisterous laughter.

"Stop, You're just going to run them. Let me help you," She said pulling them out of my hands.

Cheryl scrunched one leg up all the way to the crotch and lifted it up to my knee. She did the same for the other side and made me stand up. I tried pulling them up myself but she swatted my hand away. "You're gonna ruin them if you're too rough," She said tugging the bottom of my towel free.

The fuzzy pink towel fell to the floor leaving me in just a bra and panties with my stiff cock only an inch away from my sisters face. Cheryl looked up and locked her eyes on my junk. It might not have been the biggest tool out there but knowing my sister couldn't look away only made me harder. God I felt like such a pervert for having a hard on right then.

Cheryl slowly finished pulling the pantyhose up my legs until the tight material forced my woody against my belly. It was still hard as a rock but the tight nylon eliminated any chance of it making even the slightest bump in front of me. Cheryl made a motion like she was going to pat my junk and I squirmed away from her hand even though I was dying for some kind of attention. I sure as hell didn't want my sister giving me attention.

"How do those feel," She asked.

"They're alright," I said.

Cheryl reached down and rubbed my legs. Velvety sparks rolled up my legs everywhere she touched me and I heard a moan slip out. "Oh fuck, that's nice," I moaned.

"Wait until you feel the dress on your legs bro," She beamed.

I couldn't stop touching my legs and didn't even notice her disappear until she came back with an arm load of fabric draped over her arm.

"Try this first," She said handing me a slinky black thing with the thinnest arm straps.

"I'm not wearing this, it's way too revealing. I just need something simple," I said.

"Relax, I'm not gonna make you wear it to the bar. I just want you to see how it feels is all," she said.

"Yeah, I'm just going to the bar... not a club," I said sliding the slick black fabric up my legs.

Just like when Cheryl touched my legs, crispy waves of erotic pleasure washed through my body as the thin material came to rest around me. I adjusted the straps until my bra showed the least and ran my hands across the dress. I fought the urge to say anything. I'd already given Cheryl too much ammunition with my involuntary moans.

"How's that," She asked.

"It's alright," I lied. It was better than alright... it was great. The little black dress felt like the softest thing I'd ever touched. The way it hugged my body made me feel sexy as hell and I immediately recognized the many reasons why women wore shit like that.

"Just alright, you haven't stopped touching yourself since you put that on either. I have a feeling you like it more than just alright. Here, see if this one fits," She said.

"Just a minute, I haven't even seen how this looks," I said still rubbing the dress.

"Yeah, just alright huh," Cheryl said closing her closet door. I checked myself out in the full length mirror, turning from side to side. I inspected how nice my ass looked and how awesome I looked with tits. I couldn't believe how much of a difference a little makeup made and how much different my face looked with long hair.

"Okay... it's better than alright, like this is really nice," I admitted.

"Here, try this one," She said handing me a soft pink bundle of fabric.

I held the wad of soft material up to look at it and fold after fold of fabric dropped into the biggest skirt I'd ever seen. It looked like something Alice in Wonderland might wear if her colors were pink rather than blue. Thick tulle pushed the skirt out into a wide bell and the top had the cutest little sleeves that looked like they were only held on by a thread. The back tied into what looked like a corset with wide lace ties. I pulled the puffy dress on quicker than I thought possible and spun a little circle even before Cheryl could tie the back up.

"How does all this stuff fit me so well," I asked as she pulled the ribbon tight and tied a bow behind me then adjusted my sleeves off my shoulder.

"Everything's been kinda stretchy and this can go bigger or smaller with these ties on the back," she said.

"This is really elegant, I feel like I should be going to prom or something in this. Do you have anything less... um formal," I asked.

"You could wear this black skirt and a blouse if you want. I've probably even got some cute shoes that'll work. Do you still wear a seven," she asked.

"It's supposed to be a dress though. Do you think a skirt will work," I asked.

"You'll be good in a skirt, I promise," she said.

"Okay, let's go with the skirt then," I said hesitantly shucking the pink prom dress to the floor.

Cheryl tossed me a black pencil skirt and a white button down top that felt wonderful in my hands. I couldn't wait to see how it felt against my skin so I quickly pulled it on and started buttoning it up.

"Hey, this shirt is backwards," I cried. Cheryl just laughed.

"That's how girls shirts come," she said.

"They come with the buttons on the wrong side, seriously? How is this the first time I'm hearing all girls shirts button on the wrong side," I asked.

"It's not all of them, some button just like a guys shirt does but the dressier and more feminine blouses button on the other side," She said.

"What good does that do," I said struggling to button the top with the wrong hands. I felt completely inept at dressing myself and thought the only way it'd be easier is if I was dressing a woman for her.

"Do they put them like this so guys will have an easier time undressing their girls or what," I asked.

"I don't know bro, maybe... okay, tuck that blouse in and try these flats" she said.

"Flats, why aren't they just called shoes," I asked.

"They are shoes but they're not high heels... they're flat so they're called flats," She said explaining the logic.

I stepped into the plain black flats and flipped the heel up. They were a little tight but not so bad I was going to cry. I looked at myself in the mirror and couldn't believe how normal I looked from the neck down. With the wig, I looked like I worked at an office where everyone partied the whole day and had I been wearing a brown or blonde wig instead, I'd have made a completely convincing woman.