The Bartender

Chapter 02 The hustle

It was a Wednesday night. There is nothing deader than my bar on a Wednesday night. We did all our business on the weekends. I'm sure Pete would rather close the place during the week if he could get away with it. But he couldn't, so here I was watching three drunks nurse their beers.

It was about an hour before closing when he came in. He was wearing a suit. Last time I saw a suit in my bar was a lost vice cop looking for directions to Stella's. He sat at the bar and gave the place the once over. I'd seen my fair share of cops and this guy was definitely not a cop.

"What can I get you?"

"Beer."

"Draft OK?"

"Yeah, just make it cold."

"You got it."

I poured his beer and served it.

"Pretty dead in here," he said making small talk.

"It's a living."

"Hey you are Harry's girlfriend aren't you?"

That caught my attention. It's no secret that I see Harry. You could call him my boyfriend. I wouldn't, but others have. It's hard to call a guy who is gone for days at a time, never calls, shows up at the weirdest times day or night expecting a hot fuck, your boyfriend. But what can I say; I'm a sucker for a nine inch cock. He is more interested in hustling pool than anything else. That's how he makes his cash. For him life was feast or famine. Everything hinged on his last game.

I didn't know this guy. And from the looks of him, didn't want too. He was stuffed in that suit like a gorilla wearing a dolls' costume. He didn't look like money, so there was only one thing left.

"Used to be..."

"Mm, sorry. Not the way I heard it. Say, you wouldn't know where I could find him?"

"Not a clue. I'd look in the cheapest pool hall you can find. That would be my guess."

"Yeah, you are probably right. So I don't guess you would be talking to him, huh?"

"Not unless he brings the money he owes me. Fat chance of that."

"Yeah, I know the feeling. Well look, if you happen to see him, tell him that Benny wants to meet. Real soon."

"Benny?"

"Yeah. He will know who you are talking about."

"That's two bucks."

He slapped a ten spot on the bar and left. I waited a good ten minutes before I tried Harry's cell phone, not that he would answer. He didn't. Well this would have to be his problem.

I was beat from standing on my feet all night for a lousy twenty bucks. I kicked my drunks out and headed home for a nice hot bath. I pulled in front of the apartment and parked the car. My apartment was on the second floor and faced the street. That sucked because you could hear the traffic. But it was cheap and when you have nights making twenty bucks, you got to do what you got to do.

I made my way into the apartment and threw my purse on the sofa and headed to the bathroom to start the water for my bath. I was testing the water when I felt the presence of someone else enter the room. I instantly turned to see Harry standing in the doorway.

"Are you alone?" he asked.

"You son of a bitch! You scared the hell out of me. You better be glad I don't have a gun or you would be dead right now."

"Sorry, sorry. Did anyone see you come in?"

"How the hell should I know? And who the hell let you in?"

"I had to let myself in. We've got problems."

This was one of Harry's favorite things to do. When he screwed something up, it suddenly became 'we'. I could see from the look on his face that he was in pretty deep this time.

"There was a guy looking for you at the bar. You know the type, walking refrigerator. Said Benny wanted to meet soon, real soon. So tell me Harry, what did you fuck up?"

"Nothing I can't handle. I just need to get out of town for a few days so that I can put some money together."

"How much Harry?"

"Twenty large."

"What the fuck!? Are you crazy? How in the hell did you manage that?"

"I had a ringer. I was doing him right too. That is, until I figured out he was ringing me. Benny fronted me the money. Now he wants it back, with interest."

"Where are you going to get that kind of money?"

"If I can get to Chicago, I can put something together. I know plenty of people who can get me into a game. It shouldn't take but a few days. Then I can pay Benny off."

"How are you going to get to Chicago?"

"I don't know. I was hoping you could help me with that. Are those goons still outside?"

"You brought goons to my place? You fucking bastard." I walked over to the window and peeked outside. Sure enough there was a car across the street with two guys sitting in it. If I didn't miss my guess, one of them was the refrigerator. "I've got a good mind to tell them your sorry ass is in here. I can't believe you came here with this kind of heat."

"I just need to get to Chicago. Then I can make everything ok. But I can't really do that if I have a broken arm...or worse."

"I got nothing. I made a big twenty bucks tonight. You can have it for all the good it will do with those guys sitting outside. They are going to nail you the second you hit that door."

"Tell me about it. We just need a diversion."

"No, what we need is for you to disappear. Or better, we need for you to turn into someone else, someone they are not looking for. Hey...that gives me an idea," I said reaching for my cell phone. I called my roommate Sally.

"Hey sugar, how you doing?" She was having dinner with her boyfriend Tim. She started to tell me about her day, but I stopped her. "Hey, I've got a little problem over here. I need you to stay over at Tim's tonight. I know he won't mind. Besides, you know how you get when you've been getting too much pussy...not that I'm complaining."

She didn't really like the idea of me telling her she couldn't come home, go figure? And what did I mean 'getting too much pussy.' Was I complaining about the way she treats me. Had I lost interest in her talented tongue? Then she went the other way. Maybe I was right. Maybe she did need some serious dick to keep her in balance. She covered the phone and asked Tim if he was in the mood for some heavy fucking. Then she came back on and told me to call her later and hung up.

"What's your plan?" Harry asked.

"The only people who can walk out of that door without getting into trouble are Sally and me. So you are going to become Sally. Then we walk right down to the car and I drive your ass to the bus station. You go to Chicago and make this thing right. Those goons won't stay out there forever. Once they realize you aren't coming here, they will move on. Then Sally can come home and my problem goes away."

"That's crazy. They will never buy me as Sally!"

"Oh yes they will because you are going to sell it, sell it big. And believe me, if you give me any shit I'm going to walk right over to that door and rat your sorry ass out. You fucked up, big time. And you brought those assholes to my house. That made this my problem and now I am going to fix it. So what's it going to be?"

"I guess you should start calling me Sally," he said resigned.

"Or Asshole. I guess I will start with Sally," I said trying to lighten up. "Now Sally, go to the bathroom and shave. And I mean everything, really smooth. Not only do you have to fool the goons outside, hopefully that should be rather easy. You also have to fool a busload of people going to Chicago. That will be considerably harder. In the mean time I will try to find something for you to wear."

Harry marched off to the bathroom and I fixed myself a drink trying to calm down. I heard the shower in the bathroom. I don't know how I always end up in these situations. But I do and here I am again. I would make Harry pay for this. I just wasn't sure how.

I went to Sally's closet and started rifling through her clothes trying to picture what would look good on Harry. It had to be something that caught the eye, something very feminine to help sell the deal, but not too flashy. I knew there were enough clothes between the two of us to turn Harry into a cute little thing so he could get to Chicago. After that, he was someone else's problem.

The shower stopped and a minute later Harry walked into my bedroom shaved smooth as a baby. He looked a little weird, especially his bald crotch. He glanced down at the things I had on the bed and rolled his eyes.

"Oh man. I can't wear that stuff."

"Hey you are right. Hit the fucking door Harry!"

"Ok, ok, I didn't mean it. I just... OK, let's do this."

"You give me any more shit and I am done. Got it?"

"Got it."

"Put the bra on Harry. Just do it."

Harry grabbed the bra and slipped it on. I had to help him adjust it so that it wouldn't be so tight. I stuffed it with a few nylon stockings giving him a modest bust.

"Hey, don't you think I should be bigger?" he asked looking in my mirror.

"Well that didn't take long," I said rolling my eyes. "You want to have a bust, but you don't want to be so big that every hard dick between here and Chicago is hustling you."

"Yeah, yeah you are right," he said. "I didn't think about that."

I was beginning to wonder if he thought about anything at all.

"The panties Harry; put on the panties." He grabbed the panties and pulled them up his legs. He was barely able to get that cock of his inside them. "Turn around...let me see."

I was amazed to see Harry suddenly feeling very self conscious. It was probably the first time in his life. The panties I picked were extremely feminine, made of silk, trimmed in lace. His nine inch cock looked absolutely delicious in them. And it appeared it was getting to Harry as well.

"Well, well, well," I said smiling as that lump got larger, "who would have guessed you had a panty fetish." I stepped closer and squeezed his cock firmly, "Maybe this won't be as bad as I thought..."

His face turned three shades of red. "Who said I had a panty fetish," he said defensively brushing my hand away.

"Your cock did, that's who," I said pointing to his crotch. He had a full blown erection that stretched those panties to the max. "Don't worry baby," I said in a cutesy voice, "I won't tell." He really didn't like that.

"I'm just not used to it, that's all. I don't have a panty fetish...or any other kind of fetish. Stop talking like that."

"Sure baby...I know," I said blowing him a kiss. That just made him more self conscious. "Now put on the garter belt. I will be right back," I said heading for the door. "And be careful Harry," I said over my shoulder, "you're not used to it either." I left him standing there trying to figure out how to put it on.

I went to Sally's room and opened her drawer looking for a pair of stockings. And what did I find staring up at me? Low and behold it was her strap-on. And attached to it was Peter, the nice thick cock she likes to fuck me with. She knew about my thing for large cocks and bought the biggest she could find. I got wet just looking at it.

Then it all fell into place. I grabbed it, hiked my dress up and yanked my panties down. I slipped it on and tightened the straps nice and tight. I wiggled my hips watching it sway back and forth. I couldn't keep the smile from my face. I stroked it once or twice feeling myself getting wetter by the second. Then I pulled my panties back up hiding Peter. I grabbed a pair of stockings and headed back to my room.

Harry was standing in front of the mirror. His cock was just as hard as when I left. The garter belt straps looked so cute dangling down his thighs. I knew if the panties turned him on, the stockings would drive him crazy.

"Cute Harry, very cute," I said walking into the room.

"Hey cut it out. This isn't funny."

"Here, put these on," I said throwing him the stockings. "Now just bunch it up, point your toes and roll it up. Simple, right? Just hook them to those straps." He looked at me with such a helpless look. "You probably want to sit on the edge of the bed to do this."

He stepped back and sat down on the bed. I pulled up a chair so that I could watch. I knew it would make him feel more self conscious. I was starting to like making him feel self conscious.

He gathered the stocking up in his fingers, pointed his toe straight out and slipped the stocking over his foot. I had a perfect view of his cock. Those panties were not doing much of a job holding him. He pulled that stocking up his leg causing his cock to throb powerfully behind the skimpy panties. And that I liked. By the time he had the second one up I could see a wet spot on those panties. And I liked even more.

"Now walk around...get used to them," I said. He got to his feet and paced back and forth. He was doing his best to hide his embarrassment, but I saw right through it. He was so fucking hard. I wondered if it was really the silk or just his perverted mind.

"Gee...I don't know Harry. I am beginning to wonder if we are going to be able to hide that cock of yours. You know girls don't have a big fucking lump in the front of their panties. Well...not most girls. You have already soaked those." He suddenly looked down and saw the wet spot. It had grown considerably. "If I knew you were going to enjoy it this much, we could have tried this earlier." That did it.

"Hey, this wasn't my idea! I can't help it if...if... Shit!" he said frustrated.

"No need to get all upset baby. Sit back and enjoy it," I said smiling. I cupped his chin with my hand and hit him with the cutesy voice, "I'm going to have fun turning you into my cute little bitch." He wanted to explode and probably would have had the circumstances been different. But he needed me and we both knew it.

"Now put on these heels. They will be a little tricky at first, but you will get used to them honey." They were four inch heels with ankle straps. They screamed "come fuck me."

Harry put them on and wobbled around pacing the room. I was really enjoying watching him. His throbbing cock threatened to flop out of his panties with each step. "Try swishing your hips. Girls don't walk like that. You have to sell this Harry. You only get one shot."

He started rolling his hips and I thought I was going to bust out laughing. Of course I didn't. If someone would have told me I'd be watching my boyfriend prancing around in lingerie and heels I just wouldn't believe them. But there he was and I was enjoying the hell out of it.

"Yeah that's better, but something is missing. Step over here." Harry wobbled over to me on the bed. "Close your eyes." As soon as he did I squeezed his cock. At the same time I ran my hand up his silk covered ass.

"Hey what are you doing?"

"Shut up Harry." I continued to rub his ass making sure my finger trailed down his crack. I knew he was thinking about his cock, but I wanted him to start thinking about his ass.

"What you need is a little sex in your walk. Think about your ass Harry. That's what people will be watching." I pushed my finger right against his rosebud and watched his cock pulse. Those poor panties didn't have a chance with that hard cock. "Now try it again...and think about your ass."

I'll be damned if he didn't start swishing that ass just about right. I watched him pace in front of me, stockings, heels, panties and now swishing that ass. I was going to enjoy taking that cherry of his.

"Much better. Ok, now we have to do your hair."

"What are we going to do to it?"

"I have to put rollers in it, give it some curl. While we are waiting for that I can do your face."

His hair was almost as long as mine. I sprayed it down and rolled it up with curlers. If Harry looked weird before, he really looked weird now. But I knew it was all going to work out once he was "finished."

I pulled the chair up and started brushing on eye shadow. I made sure he could watch in the mirror. I followed that with some eye liner. "Damn baby. That cock of yours is so hard. It looks so cute in those panties."

"Cut it out!" he said embarrassed.

"You have me all revved up. How about sneaking a hand up my dress and helping a girl out?" That brought a smile to his face. He put his hand on my thigh and walked his fingers up my leg, under my dress and right into the huge bulge hidden in my panties.

"What the fuck!?" he said jerking his hand away. His eyes were huge.

"Keep going sugar," I said firmly. "You know what to do. Now do it!" He slipped his hand back underneath my dress and searched for my panties. Then he pulled them down causing my cock to flop out making an interesting tent of my dress. He glanced at me in surprise, shock.

I stopped what I was doing and waited. My stare was all business.

He wrapped his hand around it. I continued to wait, staring.

I felt him pull on it. I lowered my eyebrows, showed the slightest of grins. He started stroking it.

I leaned in and continued with his makeup. I could see everything in his eyes. He was afraid, scared and terribly horny all at the same time.

"Feels just like a real one...doesn't it Harry?" I said applying mascara.

He didn't respond. His strokes became less mechanical, more fluid. I knew his fingers were running over the veins of my cock. I could feel him exploring the tip.

"Now you need some lipstick," I said as if nothing was happening. "Pucker up sweetie." With no hesitation Harry puckered his lips together in an exaggerated kiss. I picked up the bright red lipstick and applied it smoothly to his lips while he stroked my cock. Once he was painted up, I had him look in the mirror.

"Perfect! Red is definitely your color," I smiled. Then I turned to him. My smile faded to all business. I lowered my voice and said firmly, "Now Harry...put those lips around my cock...and suck."

I yanked my dress up to reveal my cock in all its glory. Harry's eyes shot down for his first look. His eyes were so big. He glanced at me and saw that I meant business.

He lowered his mouth onto my cock and took the first couple of inches between his lips. That first orgasm shot through me like a bullet. I knew there would be more. I spread my legs, leaned back and watched Harry suck his first cock.

"That's right Harry...suck that cock," I taunted. "A girl's gotta do what a girl's gotta do." Harry just grunted. His mouth was full.

I watched his technique. He held the base in his hand and worked his lips as far down my shaft as he could. It looked to me like he was seeing how much he could take. I admired his attitude. I hoped he retained that attitude when I started fucking him.

"Run your tongue over it Harry...let me see," I commanded. He pulled the shaft from his lips and started licking it.

"Slower Harry. This isn't a race." He went from licking a stamp to something more sexual.

"Now the tip Harry. Roll that tongue over the tip." His eyes shot up at me. But he kept his cool. He moved up to the tip and rolled his tongue over it a couple of times.

"Trace the head with your tongue," I said watching. "Do it slow. Let me see. I want to see everything." He stopped long enough to digest what I had said. Then he curled his tongue around the edge of the helmet and slowly circled around tracing its shape. And that made me crazy. I could feel the juices running down the straps.

"Don't forget the slit Harry. Nice and slow." He darted his tongue up that slit and I thought I was going to have another orgasm. I could just picture long ribbons of hot cum spraying all over his face.

"Uooh that's good Harry," I said almost there. "...real good."

He swooped down on that shaft taking a good three or four inches. Then he pulled up slowly, sensuously until he came right off the end and polished the tip with his tongue. He traced the head once, darted up the slit and then went back down the shaft. That was when I had my second orgasm. It was quick and swift. It cursed through me like a bolt of lightening.

I leaned back and tried to gain my breath while Harry continued making love to my cock. He was really into it now. His eyes were closed; his moves were slow and fluid. He was clearly off in cock land somewhere no doubt trying to satisfy his perverted little mind. I know a real cock would have filled him full of cum way before now. And from the looks of things, that would have been just fine with Harry.