Ladies Night

"You don't have, like a brown wig or something do you. I look like I work for a rave company or something," I said hoping she had something a little more conservative.

"Nope, that's all I have left after Isaiah left me. He took all the fun stuff we bought. This is all I have left," she said.

"Wait... what?"

"Yeah, Isaiah's the one that introduced me to the fact that men liked to feel pretty sometimes too. Before that, I had no idea a man would have wanted to wear a dress, or even experience sex like a woman," she said.

"What, sex like a woman... what the hell do you mean by that? Isaiah is one of the manliest guys I know. Are you telling me he is gay," I asked.

"Oh god no... he's as straight as they come. He just likes his ass... well, he liked it when I'd peg him," she said. When I gave her a look like I didn't have the slightest clue what she was talking about she explained.

"It's simple really... I wear a strapon and fuck him rather than him fucking me," She said pumping her hips mimicking how a man might fuck a woman from behind.

"That sounds gay as hell," I said in disbelief.

"Well it's no more gay than a man wanting to feel pretty, or desirable, or wearing clothing that makes him feel good. It's no worse than jacking off or fingering yourself. God, you could even have sex with a man and that doesn't make you gay. You're gay when you're only attracted to men silly," She said.

"That's weird. Why would any guy want something in his ass unless he was gay," I protested.

"Look, I'm not going to get into this with you. If you think the only way you can have an orgasm Is with your penis, you're dead wrong. You can actually have better orgasms through your ass whether you want to believe me or not," She said.

"I doubt that," I said shaking my head.

"Your friends are probably waiting for you. Don't you have to go," She asked.

"Oh shit, will you give me a ride please," I asked.

I didn't really want to walk the half a mile to the bar dressed the way I was and once I got to the bar, I'd get a ride home with Mike. Cherry nodded her head and grabbed her keys. I shuffled behind her as fast as I could but the pencil skirt seriously limited my stride. The skirt rubbed against my legs and just the feeling made my cock strain inside my panties. I was glad the pantyhose held my cock tight against my body or I'd have been sporting some serious wood. Even sitting in the car felt good. It was like I was covered in the softest most sensual things known to man and my cock couldn't get any harder.

Cheryl stopped on the street in front of the bar. My guts tightened and I finally realized what I was about to do when I saw Mike in line. He didn't disappoint but he was nowhere near as made up as I was. He had a big flowered dress on over his jeans and sneakers. Even his tee shirt poked out the arms of the dress and his wig was cheaper than mine.

"Go ahead, there's Mike," She said beeping the horn.

"Jesus, don't honk. Now everyone is looking, I cried.

My palms were slick and my heart was pounding as I gripped the handle and pushed the door open. Mike was still watching the car but he looked confused when I stepped onto the sidewalk. I leaned back into the car.

"Thanks sis, wish me luck," I said.

"Good luck, call me if you need a ride home or if you need me to rescue you from all the men that are going to be hitting on you all night," She laughed as she pulled away.

I couldn't believe what I was doing. Mike had obviously not done anything near what Cheryl did for me and neither did either of Mikes buddies. I expected to see the normal crew but they totally didn't show. As I was approaching Mike in line I passed the doors to the bar and the bouncer just waived me inside along with two other women. He handed all three of us a punch card that gave us ten free drinks. Mikes jaw hit the floor as I walked passed the line of guys.

I could barely breathe as I stepped up to the bar. I knew the bartender would see through my disguise and call me out but all he did was punch my card and ask what I wanted. I looked around to see if Mike had made it in or not and when I looked back I totally caught the bartender looking at my chest. I chuckled and wondered what he'd say if he knew they were just foam inserts and that I didn't have a pussy.

"Shot of Tequila please," I said with my voice just one octave higher than normal.

He set a shot glass on the bar and filled it with Tequila then pushed the glass in my direction. It worked, it totally worked... I was drinking for free on a Tuesday night. I didn't even have to pay the cover charge and the punch card was easily worth $50 in free drinks. More if I continued getting shots.

"Hey, who are you, where's Morgan," Mike asked.

"Who's Morgan," I said in my higher girl voice.

"Holy fuck dude, is that really you," Mike exclaimed.

"I don't know this DUDE you're looking for. I'm Mandy, what's your name," I asked.

"It's me... Mike," he said like I actually had a hard time telling who he was in his cheap costume.

"You're so fucking hot man. I can't believe they just let you in like that. They totally made us pay even though we're clearly wearing dresses and wigs. It's such shit," he continued as he pulled the wig off and flipped his flowered dress over his head.

"Oh, you actually are a man under that dress," I teased. "I thought Mike was a really strange name for an ugly girl like you anyway," I laughed.

"Hey, I was cute," he elbowed me in the arm.

"You should stick to being a guy, you're much better looking not wearing a dress," I elbowed him back.

"My god, you look phenomenal! Are you actually wearing a bra," he said tracing the thin black strap running across my shoulder.

"It's just to hold my boobs in place," I said.

"And pantyhose," he said touching my leg.

"Yup, Cheryl's idea," I said.

"Don't tell me you're wearing panties too dude," Mike said trying not to look shocked.

"Well, you'll never know unless you buy me a drink now will you," I laughed nervously.

"Fuck that shit, you have the free drink card," he said.

"Maybe you should have put in a little more effort. Maybe you'd have a card too but the fact still remains that I don't have a drink in my hand and if you want to get lucky tonight, that had better change," I winked.

"I'm not trying to get lucky with you tonight, not that you aren't hot enough but I know you're packing more than just a purse. Maybe Dane will take you home," he laughed pulling his friend from behind him.

Dane wasn't wearing pants under his blue and white striped dress and his wig looked like a single dreadlock was beginning to form on the top. He wasn't a bad looking guy other than his choice of clothes.

"That's a nice dress Diane," I winked.

"Yeah, borrowed it from my mom. I sure wish I wore shorts under this though. Maybe then I could get changed," he said tugging on the short dress as though it would magically get longer.

"You look good, at least this way I'm not the only one still wearing a dress" I said as Mikes other friend flipped his dress up over his head.

"Well I can't pull it off like you do," he said.

"Why don't you let me get you a drink since you're the only one who actually understood what we were supposed to do," I said holding my punch card up.

Two shots later I definitely felt the effects of the alcohol losing my inhibitions and the dance floor started looking more and more fun, only I didn't have anyone to dance with. I tried to get Dane to come with but he was a lot more nervous about things than I was at that point.

A fast song with a great beat came on and I felt my hips moving in ways I had never been comfortable dancing as a guy. I also found the girls on the dance floor were a lot less intimidated by me, as they started getting closer and closer until they were practically grinding against me. Had my cock not been completely flattened by both my panties and the pantyhose I'd have been tenting harder than ever before. I couldn't believe how freaky girls got with each other right out in the open. One girl, a hot brunette in a miniskirt was rubbing her crotch so hard against my leg I swore I'd have a wet spot either from her pussy on my leg or from me cumming.

Luckily the song ended and we didn't have to find out but the dance had made me beyond horny. I tried to get the girls number but I got shot down. She was apparently into dancing and grinding on girls but only into dating guys. I failed to mention the fact that I was actually a guy and by the time I thought to tell her she had moved along and a group of guys was vying for her attention. She had all the right curves in all the right places and she had rubbed her crotch against me of all people.

"Holy shit man, that girl was totally humping your leg," Dane said as I sat back down.

I was huffing and out of breath and still rock solid. I needed to get the hell out of there so I could get home and take care of my throbbing tool. I finished my punch card with a round of shots for me and Dane. It was official... I was as drunk as I'd ever been and when I felt Danes hand on my thigh I was too far gone to do anything about it. Besides, it felt really fucking good.

He leaned in close and his hand ventured further up my thigh until he was close enough to whisper in my ear.

"Forget about her, I'd let you play with me anytime you wanted," he said.

My head did a little somersault and I felt my cock twitch at the thought of having sex with Dane. I thought back to what Cheryl said earlier. I could even have sex with a guy and not be gay. I already knew I liked wearing women's clothes and being a girl in public. Maybe she was right about everything too.

"Are you a top or a bottom," he asked.

"I don't even know what those are," I said feeling his hand brush across the head of my stiff prick. I moaned and squeezed my thighs together.

"Have you ever been with a guy before," he asked pausing with his hand against my cock head. I couldn't answer, I was too distracted by how great his hand felt and the fact that I realized a guy was making me hard.

"No," I whispered.

"Do you want me to stop," he asked.

"No," I whispered.

Dane continued rubbing the head of my dick through my skirt. We were secluded enough from the rest of the bar that Dane thought he could get away with lifting his dress up. I could see the bulge in his boxer shorts and couldn't look away. I knew I was looking at his erection but couldn't bring myself to return the favor and touch it even though I could think of little else at that moment until...

"Hey dude, I'm fuckin' hammered," Mike mumbled as he fell into our table.

Dane yanked his dress back over his boxers and leaned away from me. I was obviously flustered and didn't want him to stop. Had I not been drunk I'd have been in my right mind but all I could think about was what was hidden under that blue and white striped dress.

"Yeah, we're drunk too," I said.

"What happened to the dress dude," Dane asked.

"Those fuckers wouldn't give me a card so fuck em' the ass holes, but this little hottie got a fuckin' card didn't she," he mumbled.

Dane just nodded his head and looked at me. I couldn't help but look at his crotch and wonder if he was still hard or not. The whiskey made me drunk as a skunk but has steered clear of my dick and I wished Mike would just stumble back wherever he came from and leave us alone.

"I'd fuck her, what about you dude, you think she's hot enough to fuck... wait, you're gay. You don't even like chicks do you," Mike yelled over the music.

"Quit being a dick dude," Dane said. I felt like he was protecting my honor if I even had any that needed protecting.

"It's a good thing she isn't a real girl huh, cause she's still on the market," he laughed.

"You know, you can eat a dick dude," I tried to say but something else came out that sounded a lot closer to, "You know, I'm nna eat a dick dude."

"I'll bet you are, I'll bet you are," he laughed so hard tears ran down his face.

I covered my face with my hands as Mike laughed. I could feel Dane place his hand on my back as he leaned across the table to give Mike a piece of his mind.

"Hey fuck head, if you remember right, this was all your idea but you decided not to show up in a dress. You just threw one on over your fucking clothes ruining it for those of us that did actually put a little effort into getting a fucking card and then take it out on us. Maybe next time you come at us with one of your hair brained ideas, you prove your commitment before anyone else follows your lead, now get fucked dude," Dane yelled.

"Yeah whatever man, y'all have fun," he said stumbling away.

"God, I thought he'd never leave," I laughed.

"Yeah, such a jerk," Dane said placing his hand back on my thigh. It felt nice but the magic of the moment had passed and it all felt a little too weird to continue. His fingers slowly worked closer to my cock head but it felt wrong.

"Hey, I've got to go. I've got class first thing in the morning," I lied.

"Come on... one game of pool before you leave," he said.

I think deep down I wanted him to keep pursuing me even if he was gay. I think I needed to find out if what he and Cheryl said was true or not. My cock sure knew his hand felt good.

Dane racked the balls and I did my best to aim down the stick and deliver a great break but I'd never been much for pool and being as drunk as I was only made my aim worse. I hit the cue ball with the side of my stick and it careened away from the rack and fell in the bottom corner pocket.

"Um... that's a fowl, it's my shot," Dane said.

"Wait wait, gimme one more chance. I can get it, I just need to focus better," I said.

"Lemme help you," Dane said stepping in behind me.

He wrapped his arms around me and leaned over my back. I could smell his aftershave. His body pressed against me and I realized how cold I'd been and how warm his body was. He grabbed my hands and directed my left hand to support the stick. He grabbed over my hand and pumped the stick forward and back a couple times.

"You seem pretty good at that movement," I teased.

I felt his cock press into my ass as I pushed back into him. He lined the stick up and pulled the stick back. Just a moment before the cue shot forward he pumped his hips into me and the balls shot all across the table. Three balls went in and I cheered as he stepped back to watch.

"I could show you how to be that good too," he winked.

I wasn't sure if he was talking about breaking or something else but I liked it either way. I lined up for a super simple shot that I couldn't miss and shoved the cue forward. It scooped the cue ball up and threw it off the table in Danes direction almost hitting him right in the gut.

"Careful there, I don't want you accidentally hitting me in the nuts," he said.

"Oh calm down, I'd kiss them better," I said.

I immediately looked around to see if anyone heard what I said but we were still mostly alone. Dane smiled at me and started looking for a shot. I knew if he was as turned on as I was that I could probably use my body to distract him and maybe I'd win the game. He lined up a great shot from corner to corner and I slow danced as as much like a stripper as I could imagine but the ball clunked in the pocket anyway.

"Fuck, that was a good shot," I said.

"I always find the hole," he said.

He lined up for another shot and I attempted to shake my big fake tits toward him and he drained another ball. Nothing I did was working. It was like he was a pool shark. I had to get creative. I had to think about what would fuck him up so when he lined up again, I leaned in close and whispered in his ear just as he pulled back to strike the cue.

"What hole will you find on me," I said feeling super slutty.

Dane completely missed his shot and knocked in two of my balls. He'd turned a visible shade of red and I felt triumphant for getting under his skin. I had him beat for sure if I could just drop a few balls on my own but I missed again.

"It's okay, we're still tied up. What are you gonna do when I beat you," I taunted him.

"Oh, you want to make this interesting do you," he smiled.

"Yeah, what do I get when I win," I asked.

"Whatever you want. Hundred dollars, a back rub, a blow job, whatever you want," he smiled at me.

I knew his weakness. I knew I could beat him so I could offer him whatever I wanted. He wasn't going to win. "You win, I'll let you pick the hole you drain those balls into," I smiled looking down toward his crotch.

Dane got an evil look on his face and completely shot me out. He ignored me for the next three shots. All he had left was a two ball and the eight ball. I had to pull out all the stops or he'd really be unloading his balls somewhere inside me. I leaned in and whispered the dirtiest shit I could think of in his ear.

"If you make that shot, I'll suck your dick right here in the bar," I said hoping and hoping that he'd miss.

Clack... and he missed!

"Back in the game," I hollered.

I had three balls left and the eight ball. Magically I drained the shot I was aiming for and accidentally knocked my other two balls in bringing me into the lead. All I had to do was sink the eight ball and not scratch. All I had to do was win whatever I wanted from Dane but I wasn't sure what I really wanted. Did I want to loose on purpose so I could say it was because of a bet or did I want to win and take what I wanted because I wanted it.

"What do you want if you win," Dane asked.

"You'll find out soon enough," I winked.

I was almost laughing. Dane leaned in close and whispered in my ear. He used my own dirty attack against me and threw me way off my game.

"If you miss, I'll know it was on purpose," he said and he backed away.

If I missed, it'd be on purpose. But if I won... I couldn't lose. The shot was too perfect. If I missed, it would have to be on purpose. A huge smile grew across my face. I pulled my stick back and drove the cue ball forward at a tremendous speed smashing the eight ball right into the corner pocket.

"I win, I win, I win," I sang dancing circles around Dane.

"Wait for it, wait for it..." he said.

I had no idea what he was talking about and didn't really care either. I'd won fair and square, but my heart dropped and I finally registered what he was looking at. The cue ball had hit nine bumpers and was slowly tracking toward the exact pocket I'd dropped the eight ball into. He started jumping even before I'd lost but I knew it was over even before the cue ball disappeared leaving nothing else but the two ball on the table.

"What was it I got when I won," he asked.

"You know what it was," I sulked. I couldn't believe he won on a technicality. He didn't win, I lost. He didn't beat me, I gave it to him and now I'd really have to give it to him.

"You did that on purpose didn't you," he said.

"Maybe... maybe not. We'll never know for sure will we," I said hanging the stick back on the wall.

"Double or nothing," he said enticing me to pause with the stick still in my hand.

"If that was an accident and you actually did beat me, I'll give you the chance to get even, but if you meant to lose and want to pay up, hang that stick back up and let's get out of here," he said.

I held on to the stick for a moment as I thought about actually beating him. I thought about what we'd be doing if I didn't play another game and I thought about doubling my current bet.

"If I lose, you get to drain your balls in whatever hole you want... twice," I asked.

"Yup, two times, but you can avoid all that by just beating me this time," he said.

I knew I couldn't actually beat him. The only decent shot I'd made all night was the eight ball and I still scratched. I was always garbage at pool and Dane was actually good. It was getting late and if we were going to do it, I'd rather do it a little drunk.