The Bartender Ch. 04

Giving into my issues...

I was pretty rested by the time I arrived in Chicago. I got off the bus and headed for a taxi. I could afford one now thanks to farm boy. I got in the cab and we headed to the south side. Benny wouldn't be looking for me there. That's where I would find a game. I just needed to make one stop first. I needed to buy some male clothes.

I rented a cheap hotel room not far from a pool hall I had been too before. I knew a few guys that used to hang out there. If there was a game, they would know it. They would fix me up.

I kicked off my heels and threw them in the closet. My feet were killing me. I hung up my dress trying not to think about things too much. I walked into the bathroom to start the shower and caught my reflection in the mirror. I was still wearing panties, makeup, my hair was curly. Gees, what the hell was I doing?

I waited for the water to run hot and stepped in. I shampooed my hair several times trying to get the curl out. The shampoo lathered up really nice. I smoothed it all over my body paying particular attention to my cock. I felt really different without hair.

My cock responded quickly to the nice thick lather. I got a handful and started stroking. I thought about sucking Shelia's cock. That was nothing compared to the real thing. I stroked a little harder. I thought about farm boy exploding in my mouth, tasting his junk just before swallowing it. I painted the shower wall with my own. Yeah, I needed to straighten that out. But it would just have to wait.

I toweled off and looked in the mirror. My hair looked fairly reasonable. All traces of the makeup were gone. I needed to make some calls. I stepped into the other room and slipped on a pair of jeans. For half a second I toyed with the idea of putting the panties on underneath. Yeah, I had some things to straighten out.

I got on the phone. It took several hours, but I got a game. I needed to play big. There was nothing like playing with your lunch on the line. For me, it was lunch, dinner and breakfast all rolled into one. I needed to break a thousand before heading north. That was where the real money was. I figured I had a day, day and a half before the word got back to Benny.

Six hours on the south side. What a nightmare. At least I didn't live there. I had a little over two grand and headed north. Things would move a lot quicker on the north side. It was getting dark, so I figured I had the night to make my money. If I got lucky, I would make my score and be on a bus before daylight. If I didn't have the money by then it wouldn't make much difference. The word would be out and I would be over.

I started out at Hole in the Wall. Nice enough place, plenty of suckers. I hustled up a few tourists, doubled my stake and headed for She's Mine. People playing the circuit showed there from time to time. Fast money if you can pull it off. I didn't have a choice. I ran into Freddy, told him my situation. He said he could get me the game if I had a little scratch. I slipped him five hundred. I was in.

Daddy's Money. You wouldn't know it was there if you weren't a player. The stairs went up to the second floor. You could cut the smoke with a knife. Freddy put in a word and we stepped into a private room. One table, that's it. Nothing fancy, all business.

Thousand bucks a game to start, money on the table. I glanced around the room. Three guys, one chick. Only one was playing. The others were muscle. That meant big boy had some cash. I turned my back to them and peeled off ten bills slapping them on the table. He put ten on his side and we were on.

He won the lag and I felt the sinking feeling in my stomach. I stepped back against the wall and watched him shoot. He was cool, steady as a rock. He didn't move too fast, didn't take too long to shoot. He knew where he was going. He dropped four balls, but squeezed the five just a little too tight for the side.

I was lucky to get a turn. I needed to drop a few, get a feel for the table, build some confidence. I started out very conservative. I took my time, pushed everything from my mind and squeezed them in one by one. I made an eight nine combo for the win. I rose from the table and looked at big boy. He was taking it well. I glanced at the muscle, they were relaxed. I walked around and collected the money. I put it on my pile and shot him a look. He peeled off twenty bills and dropped them on the table. I started rolling balls towards the base line.

I'm not sure how long we played. The smoke was killing me. My eyes were watering, my head ached. Big boy was pretty damn good. I was up, but not by much. I knew things could shift any time. I was getting tired. I would have packed it in had I a choice. I didn't.

It would be light outside soon. This could go one of a few ways. I could let my guard down, loose. If I didn't wrap this up soon it wouldn't matter. Benny had a price on me. I didn't have the time. I needed to win. The question I'd thought about for the last hour or so was this; was the muscle going to let me keep the cash? There was only one way to find out.

"You're good...but I can beat you. I'm all in," I said.

Big boy smiled on that one. I hoped it was a bluff or maybe ego. Whatever it was, it shook me. He pulled the money out, matched the bet. I glanced at the muscle. They were wide awake. Even the chick was staring at me now.

I racked them up real tight, stepped back from the table. That was what I liked about the game. You won or lost, there were no ties. I knew that minutes from now my problems would be over, one way or the other.

He dropped the two on the break, had a nice spread on the balls. That smile was gone, his eyes on the table. Naked women could be dancing all over the place and he wouldn't have noticed. He moved quickly for the one. He used the three to drop the six, left it lined up perfectly for the side. He made a sweet little chip shot dropping the three lining up for the four. Time stood still, he was the only thing moving and he was moving like a dancer.

Then it happened. I chalked it up to over confidence or maybe he just choked, not sure. He missed his shot on the eight.

Nothing could have been sweeter. Two balls, that's it. Open table. I could fucking do that with my eyes closed. I stayed in my chair; let the first wave pass. Got to my feet, but felt weak. My palms were sweaty, my head was everywhere. I was going to blow it! Fuck!

I walked around the table, looked at the shot. So sweet. I pushed everything from my mind, everything. There was nothing left but that eight ball. I drop that and then the nine and I am done. The sun will come out and all my babies will be born naked. My shit will turn into ice cream.

I line up behind the ball. I have made this shot six million times. I inhale, squeeze it off. Smooth as silk. It's all about the nine. I move quick before I can think. I line it up, squeeze. For a moment I thought it was not enough. The ball was moving too slow, not enough juice. I was going to fall short. My stomach reacted first. But then it dropped. It dropped in the corner.

Holy fucking shit!

I held it together. I was not out of the woods yet. I rose up slowly and glanced at big boy. He was upset, but not crazy. I looked at the muscle. Suddenly I felt like a chocolate cake at a weight watchers meeting.

"Good game," I said putting the money in my pocket. "Let me take a piss, then I will buy you a drink." I headed for the bathroom before anybody said anything. Once inside I locked the door. I wasn't sure what they would do. It's hard to figure guys like that. I couldn't afford to take the chance. I opened the window and crawled out.

I headed back to my hotel room by way of a liquor store. I held it together until I got safely inside my room. Then I pushed a chair up against the door and poured myself a stiff one.

I did it. I pulled it off. I downed my drink. It felt good. Now that it didn't matter, I fell apart. My hands were shaking. I downed another. Shit that was close. I couldn't wipe the smile from my face.

I woke up in that chair. I must have dozed off. I saw the empty bottle and then looked at my watch. I needed to get my ass to the bus station. I stepped into the bathroom and took a quick shower. I had to be careful now. There had been plenty of time for word to get to Benny. I needed to make a decision.

I walked back into the other room and saw the jeans on the bed. Then I looked in the closet. Shit. I went back and forth, but knew the right answer. I fastened the garter belt around my waist and sat on the bed. The nylon felt good going up my legs. The panties did too. I was hard as a rock by the time I got that yellow dress over my head.

I walked into the bathroom and looked in the mirror. I had no idea what I was going to do with my hair. I didn't have any curlers. I parted it in the middle and brushed it behind my ears. I pulled the makeup from my purse and tried to remember the things Shelia did.

I stared at myself in the mirror. I looked pretty bad. I couldn't get on the bus looking like I did and expect anyone to believe I was a girl. Shit. It was too risky going as me. What the hell was I going to do? The difference was I had money this time. That helped. I pulled out the phone book and found a beauty salon a few blocks away.

It was pretty crazy no doubt about it. I walked right into that beauty salon and sat in the chair. I didn't even use a feminine voice. Why bother? I pulled out a hundred dollar bill and told them to do me up all the way. And man did they.

I'm not sure what it is about women, but when a guy turns himself over to them they really get off to it.

They did my hair, my face, everything. I looked in the mirror and knew I could pass easily now. There was just one problem. You could see it a mile away. I asked if they had a bathroom.

I pulled it out and started stroking. Man I wanted to fuck something real bad. Or maybe have something fuck me. I thought about asking one of the girls up front, but that's not what I wanted. I thought about that bus ride up, that warm throbbing cock between my lips. I sucked the hell out of that cock. That's what I wanted. I pumped a load right into my hand, brought it to my lips and drank.

Yeah, I definitely had issues.

I walked to the front and dropped off an extra hundred as a tip. They knew what I did in the bathroom; I could see it in their eyes. Hey, now they had a story to tell. I touched up my lipstick and took a cab to the bus station. I could hear my heels clacking against the floor as I walked over to get my ticket. A few heads turned to check me out. They had no idea. I bought a ticket and took a seat waiting.

I glanced at one of the guys who had checked me out. I wondered if he would pay a hundred bucks. I bet he wouldn't last as long as farm boy. Hell I might do it for free. Shelia would get a real kick knowing what she started. I wasn't about to tell her.

The bus ride was long and uneventful. I slept most of the way. I thought about how I was going to get the money to Benny without getting hurt. I thought about farm boy. I thought about pulling a blanket over me and jacking off.

I took a cab to Shelia's bar. I pulled the compact from my purse and touched myself up. Funny, I wanted to look good for her.

"That will be two bucks," I said serving the beer. My feet were killing me. I glanced down the bar as I waited for him to pay. I couldn't believe my eyes. I would recognize that yellow dress anywhere. He had plenty of sex in that walk of his. I watched as he sat at the bar. It took a lot of guts to come in dressed like that.

"Hi Cutie," I said with a smile, "Don't you look nice?" Then under my breath, "Are you out of your fucking mind? What the hell are you doing here?"

His pretty red lips bent just slightly, "Everything's cool. I got the money in my purse."

It took a minute for that to sink in. He had pulled it off. I couldn't believe it. And that's not all he pulled off. I checked out his hair, his face. It was perfect. Did he do that? He had gone with bigger boobs this time.

"I close in thirty minutes. Have a drink." I filled a wine glass full of whiskey and took it to him. That yellow dress was really getting noticed. I smiled. They didn't have a clue.

"Hey, two beers over here."

"See you later sweetie," I turned to serve my other customers. Everyone wanted to get that last round before closing time. But I kept an eye on my little damsel in distress. It didn't take long for the show to start.

One by one they started hitting on him. They were swarming like flies. I had to hand it to him. He was giving it just enough flirt not to piss them off, but not enough to show interest. I took him another wine glass full of whiskey and gave him a smile.

I made my way to the phone and called Sally. "You will never guess who just walked into my bar. He has a nine inch cock and is wearing your yellow dress."

"You're shitting me!"

"I most certainly am not," I said watching the other end of the bar.

"He's wearing my dress...in your bar?"

"He certainly is. And if I didn't know better I would say he is enjoying it."

"Oh my god!" Sally giggled. "I would love to see that little slut in action."

"Don't worry; I'm bringing her home as soon as I close."

"I can't wait to see this!"

I served sweet thing another wine glass and announced last call. She drew a flurry of attention, but I pushed them out the door. I locked it and turned to see Harry sitting at the bar with that cat-ate-the-canary look on his face. I had to say he pulled it off wonderfully.

I walked over to him, spread his legs, mashed myself up against that yellow dress and gave him a wet, slobbery kiss. It was just like kissing Sally.

"I thought you were enjoying that," I said feeling that unmistakable hardness. I could see him blush underneath his makeup. "I can't wait to get you home girlfriend."

It didn't take long to drive home. I could see Harry fidgeting in his seat. I hoped he was thinking about last time. I sure was. I liked fucking boys. I slipped my hand across the seat, moved his dress up enough to show some leg. I saw his garter strap. I moved it a little more. I wanted to see his panties.

And there it was. That magnificent lump of his was throbbing underneath that lace trimmed silk. Harry had a panty fetish.

We walked up the stairs to the apartment. "I see you learned how to walk," I teased swatting him on the ass. He didn't say a word, but continued to swish that ass just right. That boy wanted some cock.

Harry took three steps inside the door and froze. He wasn't expecting Sally.

"Well, well, well...would you look at that," Sally said stunned. "I never thought I would see the day..." she said making a full circle around him. "You're right...he's gorgeous."

"Check out his panties," I said.

Sally tried to yank his dress up, but Harry got a sudden case of shyness. "It IS my dress, you know," Sally said looking him in the eye. She tried again and Harry relented. "And those are my panties too," she said squeezing his lump. "Why Harry...I had no idea." Harry's face turned completely red.

"You should have seen him at the bar. He was having a ball."

"I bet he was. That dress was always good luck for me." She ran her hand over his silk covered ass. "Did you have fun making those boys horny?" Harry didn't know what to say, how to act. "Is that what put the bulge in your panties?"

Harry looked like he had just been hit by a car. Sally wasn't about to let it go. She leaned next to his ear, "Shelia tells me you suck a mean cock."

He shot a look over at me. He turned three shades of red. Yes, I told Sally everything. He realized that now.

"And that's something I want to see Harry. I want to watch you suck cock. The rent on that dress just came due." Sally grabbed his hand, gave me a wink and led him over to the couch.

Sally sat down on the couch and spread her legs. "Right here Sugar," she said patting her crotch. Harry got down on his knees, between her legs.

I could feel my panties growing damp. Sally was a master of the strap-on. I should know. I couldn't wait to see her work her magic on Harry.

She grabbed Harry's hand and put it between her legs. Harry's eyes opened real wide feeling that twelve inch cock. "My, my, my... you are a size queen just like your girlfriend." Sally smiled watching Harry play with her cock. "I bet none of your boyfriends at the bar had a cock this big...did they? You know you were making them hard. Did you cop a feel?"

I'd never seen Harry so complacent. Sally was dishing out orders and he obeyed. That's when I realized he wanted to do it. He could say whatever he wanted, but I knew he liked it. I was cool with that. Anyone could see he was looking forward to sucking Sally's cock. I was more than cool with that.

Sally settled back and spread her legs invitingly. "Why Harry...I do believe your mouth is watering. Well go ahead sweetie..."

Harry glanced over at me. I just stared back at him, waiting. He pulled Sally's dress up and sure enough, her panties were bulging even bigger than Harry's. "Getting closer... aren't you baby? I bet you can already feel it between your lips. Your girlfriend loves to suck this cock too. I can't tell you how many nights she has been exactly where you are...getting ready to do exactly what you are going to do."

I watched Harry peel back her panties exposing her cock. "Mm...I think I'm going to like this," Sally whispered. "Wrap those pretty red lips around my cock. And suck."

Harry stared at that huge cock. He must have been in heaven. He leaned forward and took it between his lips.

"More Harry," Sally hissed, "take more cock." Harry opened his jaw more and slid down another inch or two. "Yeah...that's more like it."

"Remember Harry...nice and slow," I whispered over his shoulder. I didn't need to say it. His eyes were closed, his movements were so sexual. He had turned into a regular cock whore. I guess that was my fault.

Harry was so focused on that cock he didn't even notice me leaving the room. I slipped into my bedroom and got out of my work clothes. Just knowing what was going on in the other room was enough to make me wet. I thought about Harry at the bar, the way he was dressed. It was kinky as hell, but it turned me on. I thought about his panty fetish. Sally and I would make the most of that right after we finished feeding him dick. I slipped into my sexiest corset and strapped on my killer cock. I love huge cocks. Mine was so big I could barely get my hand around it.

I walked back into the room. Harry was so hooked on that big cock. Sally's eyes went immediately to my cock swinging between my legs. She gave me a wink and a smile. I stood and watched for a minute playing with my nipples. This was going to be fun.

I sank down right behind Harry. Slowly I raised his dress in the back exposing his ass. "Those are the cutest panties," I purred. "Who would have thought Harry had a panty fetish?" I reached around and felt the front of his crotch. It was soaked.

"We certainly know how to feed that, don't we?" Sally smiled.

Harry moaned hearing that one. I thought about last years Halloween costume. It was a French Maid uniform made of black satin. I still had the petticoats to go with it.

I mashed my cock up against the cute little ass of his. "We're going to have some real fun around here...aren't we Harry?" I said smiling at Sally.

He started to rise up, but Sally put her hand on his head and pushed him back down. "No, no sweetie...you aren't through yet."

I pushed the tip of my cock inside him, "Here we go baby...just like last time. Have you been thinking about that baby...thinking about me fucking you again," I said pushing another inch inside. "I like fucking boys." I kept pushing cock into him until it was buried. "That's it baby...now you have all twelve inches."