Bartender

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Tips are where you get them, he learns.
1.2k words
4.28
31.3k
7
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Part 1 of the 2 part series

Updated 09/22/2022
Created 04/10/2011
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"Sorry, I'm closing up," I said to the rap on the door.

"Please, I think I left my purse in the ladies' room," she begged.

I peered through the glass, and saw she was alone. There had been robberies at bars in the area, and I didn't want to be next.

"Okay, come on in," wary of someone charging the door, and she slid in. I recognized her immediately. She had left only 1/2 hour ago with her friend, a man about her age. She had been friendly while Jack, the friend, seemed annoyed at her out-going personality. Her name, she said, was Gail.

She had jet-black hair, in a pageboy, a round face, pert nose, and soft, tempting lips. She had plenty of curves, fairly large breasts, and stood about 5'8.

"I'm sorry to bother you, Harry! I said I'd stop by again, but didn't mean this soon!"

She had an infectous laugh, a throaty purr to it, and I had liked her at once, but in the bar business, many women flirt, hoping for free drinks. And with her being 20 years older, and on a date, I had been courteous, deferring to her boyfriend.

Gail made a point of saying Jack was just a friend from work, which annoyed Jack even more.

I smiled back, "That was quick. Where's Jack? In the car?"

"No, I have my own car, we were chatting in his car, and when he left, I realized I had left my purse.

"I haven't cleaned in there yet, I hope no one walked out with it. Go check."

I was pretty-much done, and was about to have a beer before I went home, all the lights were out, except dim lights that we left on to discourage burglars.

She came back out with her red purse held like a prize. "Ta-Da!" she beamed. "I'd never look respectable tomorrow without my magic bag of tricks. Like grease paint for a clown!"

I smiled at her, seeing that she wore quite a bit of make-up, from eye-liner, to eyeshadow, lip gloss, the works, but it probably hid years on her, because she looked pretty good for her age, which I figured for 45.

"I'm having a nightcap, if you'd care to join me before you go."

"I thought you'd never ask!" that contageous smile again.

We stood at the back end of the bar, quietly chatting. There's a certain silence in a closed empty bar, almost church-like, and we spoke in whispers.

"I have to admit something," she said.

"What's that?"

"I left the purse there on purpose, hoping Jack would leave sooner, so I could stop back to see you."

"Why?"

"I don't know, I don't usually hit on guys, but Jack was rude to you, and I could see you bite your lip. I thought maybe I owed you an apology for his being such an ass."

"To tell you the truth, I couldn't see what you were doing with him. You have very different personalities."

She smiled, weakly. "I know, we dated once and now he's hooked on me, I guess."

"I can see why, you're way more fun than him. And you don't owe me anything, I deal with jerks all the time in here."

Her hand touched my arm, and her eyes softened. "Do you have an older brother who happens to be single?" she smiled.

"Nope, an only son," I grinned.

"Ahhh, my loss again! Too bad I'm not rich and famous, maybe I could tempt you, then"

Sipping my beer, "You're tempting me now!"

She turned, facing my side, and wrapped her hands around my arm and tugged closer, her breasts wrapping around the arm. "Really? How tempted?"

My face flushed and I felt my manhood stirring. "Gail, you seem real nice, but I have to tell you, I'm in a relationship, even though its not gonna last, I don't want you to think I was just using you.

"Are you married? Engaged? Gay?!?!"

"No, to all!"

"Then, we are just friends, and friends can make friends feel...special. I'd like to be your friend."

I looked at her, felt her heat against me. "I'd like that, too."

She kissed me, very softly, tentatively. "Hello, friend."

Her mouth was warm and soft and her tongue darted out, licking across my lips, as her hands began to roam, searching, then finding my cock, hard in my jeans.

This was a woman on fire, my favorite kind. She needed it and so did I.

Her lips trapped my tongue and sucked it like a cock, her body in motion, touching, moving, pressing me back into the shadows. "I want to show you how good a friend I can be, Honey."

I let my hands explore her tits, sliding her top over her head, dropping it on the bar and unhooking her bra. Her nipples were erect, and when I felt them, she cried out, "Ouch, ow, they're very sensitive, they....ooooohmmm"

I released her breast, and she said "I'm very sore, and I really can't... but I'd like to satisfy you."

I felt bad. "No need.."

"No, I reaaly want to, suck you."

With that, she slid to her knees, expertly opening my fly, fishing inside and undrawing me, in the darkness. I couldn't see her but when those lips encircled my head, I sure felt her.

She swirled her tongue and I grew in her mouth as she moaned, and I let my fingers run through her black hair. Her hand cupped my scrotum and gently squeezed and I thrust into her mouth with that urging.

Her mouth was so wet, and she forced herself faster, taking all of my 6 inches, until she almost gagged, then she backed off, spit into her hand, and jerked me until she caught her breath, then began sucking again.

I was groaning, enjoying my best tip of the night, wondering how I got so lucky.

My pace quickened, thrusting into her mouth, knowing I wouldn't last much longer. I was fucking her face. If she liked to gag, I'd let her.

I felt my balls tighten and with one final thrust, I released a spray of cum, deep into her throat!

She coughed, gagged, swallowed, held on to my hips, and managed to take most of it down. The rest sprayed out, down her chin, onto her tits. When she stood, she was quite a mess, her eyes streaked from tears at the gagging, her hair messed.

She grabbed a bar towel, wiped her face to dry it a bit. She grabbed my beer and drank greedily, washing down the cum and she smiled.

"I really needed that..., I can't tell you why, but if you are interested in pursuing this...friendship, I'd really like to see you again."

"I'd like that," I said, using the bar rag to wipe myself and zippering up, while she dressed as well.

"I really have to run, now, Thanks, Honey," kissing me on the cheek, grabbing her things. I let her out, watching as she climbed into the back of a Cadillac I hadn't noticed. The engine started immediately, and whoever had been waiting for her drove away.

I wondered if I'd ever see her again, and who was waiting in that car.

Strange business, bar-tending.

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