Flirting Has Benefits

Dear diary...August 28, 19..

All persons are 18 years or older.

I'm not really a flirt...

Hell, who am I kidding? I am a flirt. A shameless flirt. An automatic flirt. Although, if anyone ever replied yes, I would probably freeze. After all, I'm 60 years old.

A local community near my home hosts a Founders Day celebration every year. It's just for one day. The day starts with a parade in the morning, an arts & crafts market, gambling tent, and starting at noon, they have an outdoor bar and bring in a band for music, dancing, and socializing. For over 20 years, I have been one of the evening bartenders at the outside bar. It's a blast. Everyone comes up to the bar to get a drink so I get to see friends I may only see once a year.

People who come to this party are as varied as any group. Ages range from 21 to 85. They range from golfers just off the course to Harley riders. Women dressed for clubbing to locals who just come to see friends. I love to watch the women who come dressed for clubbing. Usually, they wear low-cut or crop tops, short skirts and high heels. Low-cut tops are great when they bend over to get a ticket from their purse, but short skirts and high heels are always good. Those are my big weaknesses in life. I am a die-hard leg man.

I incessantly flirt with every woman who comes to my station. Young or old, gorgeous or plain, I flirt with them all. Usually, I get a smile, occasionally a hug, rarely a kiss, or even more rarely, I get laid. In fact, it's only gotten me laid once from flirting at this event, or twice depending on how you count it. I'll let you decide.

This particular year happened to be perfect. It had been hot and sunny all day. The band was a particularly good band for dancing and the crowd was huge. The bartenders were busy from the beginning of the shift until the end. I was working the 8:00pm to midnight shift - the last shift. And the shift with the largest crowd. Club women were everywhere, and I wondered how some of them could wear their skirts so short without being arrested.

Anyway, I had been flirting all night when a new woman came up, about 9:30. She was young, probably twenty-five or so with a nice rack and very short skirt. She also had gorgeous legs which I would have loved to wrap around my neck. She was short, maybe 5'3" or 5'4" but her 3" heels made her seem much taller.

But it was her eyes...I've always considered myself a leg man (any woman in a short skirt and high heels, as I've said) but her eyes were a deadly shade of blue. With her white top and dark tan, her eyes seemed to shine.

She asked for a Miller Lite. Now, in the outside bar, we only sold Bud products. But I told her she could go inside if she wanted something else.

"Are you lying to me" she asked?

"Darlin', could I lie to those eyes?"

She smiled and asked, "Are you flirting with me?"

"Absolutely" I told her. "Any man who didn't is a fool."

"I think you're too old for me."

"I'm not old, I'm experienced."

:Experienced...?"

"Oh yea, I could do things to you that I've been doing for over 40 years...things your young boy friends haven't even thought of...things I learned before they were even born."

She just laughed; said she'd take a Bud Light with lime. I grabbed her ticket, gave her the beer, and she turned and went back to her friends. I don't know exactly what she said to them, but they all turned and looked back at me and started laughing. I just held up a drink and laughed right back. Then I had other customers and had to get back to work. Frankly, since I flirted with everyone, I didn't think anything about it.

Now I didn't see her again for quite a while. We usually have 8-10 bartenders working and if one is busy, the customers will go to whoever isn't. I always try to get one of the busier locations since it helps to pass the time and gives me the opportunity to see more people. About 10:30 she came back to my station.

"What kind of things?" she asked without saying anything else. Well, it took me a minute, but I remembered I had told her I could do things to her that her boyfriends didn't even know, I knew what she meant. So, I decided to take a chance...

"I can make you cum more in one night than you have in your entire life."

At first, she looked shocked. Then she looked upset. But I figured, what the hell, she asked me. But all she ended up doing was asking for another Bud Light with Lime. Once I had given it to her, she looked at me and said that would be nice, but she never came more than once a night.

"Then you need to change boyfriends or change hands."

Then she smiled, shook her head and went back to her friends. Then the same routine as before - she must have told them what I said, one covered her mouth, the rest turned to look at me and laughed. So again, I raised a beer to them, took a drink and started serving again. Around 11:00, they quit selling tickets and around 11:30 we quit serving, although that often means closer to midnight when the band stops.

At 11:25, the bar lights were flashed as a warning. We served for about 5 or 10 more minutes until they turned off the lights on the bar. We'd do a little cleanup and then we bartenders could grab a beer and listen to the last 15 or 20 minutes of music. So, I was standing near the back of the crowd listening to a surprisingly good version of "Hotel California" when I felt someone grab my sleeve. This happened all the time when people came up to say hi, but this time it was her.

"I'm from Missouri" she said, "You'll have to show me." She seemed a little tipsy. She must have more than just the two beers I had served her.

"Excuse me, show you what?" I couldn't believe this was really happening.

"I want to see some of those 'things' you can do so well."

Now I was in a fix. This had never happened before. What do I do? Did I really want to believe this 25-year-old was going to take a 60-year-old to bed? Or would I say ok, and all of her friends would show up and start laughing?

Hell, I can only be embarrassed. And it certainly wouldn't have been the first time.

"OK, what have you got in mind?"

"I just live about 2 blocks down, at the Maple Tree apartments. My roommate is out until, at least, 3:00 unless she finds a boyfriend. So, we have plenty of room and plenty of time."

By now I figured in for a dime, in for a dollar. "OK, let me get my truck."

"No, it's only 2 blocks, we can walk."

"Alright, in that case I will be happy to escort you home, so you don't have to walk the dangerous streets alone."

I quickly finished my drink and we left. During the walk, I found out her name was Victoria ("But everyone calls me Vicki") and she really was from Missouri. She was a student. Oh-o, red light. As a college administrator, I could only think that I was being set up by a student, or group of students, from my college. So, I had to ask where she was a student.

"At the community college across town."

"Really, what's your major?"

"I'm studying to be a nurse."

"Well, great. If I have a heart attack tonight, you can give me mouth-to-mouth."

"Oh, I'll do that anyway." As she said that, Vicki threw her arms around my neck and planted a kiss on me that made me feel twenty years younger. First, she stabbed her tongue into my mouth, and when I put my tongue in hers, she sucked on it like it was a straw. Our tongues put up quite a battle and there was no clear winner, nor actually a clear loser.

Catching my breath, I grabbed her hand and said, "We better get inside before we get arrested."

"Why...are you afraid of the dark?" she asked with an impish grin.

"No, I'm afraid my resistance wouldn't stand too many more kisses like that. And I'd be tempted to take you right here."

"Well, I am wearing a skirt..." Then she flipped up the back of her skirt and I saw that was all she was wearing. There was nothing but her under the skirt. That brief glimpse showed what looked like an amazing ass.

I took her arm, and we started walking again. I reached back and gave her ass a squeeze. I confirmed that it felt as great as it looked. Smooth and firm. Everything a young ass should be.

When we reached the apartment complex where she lived, she led me toward her building. It was in the back and her apartment was on the second floor. She unlocked the outside door and led me up the stairs and turning to the right, she walked to the second door and said, "This one is mine."

Always the gentleman, I took her key and opened the door. Allowing her to enter first, I followed half expecting her friends to jump out. But no one did. We were alone. So, I took the key out of the door and closed (and locked) the door. I followed her into the living room and watched as she bent over to dig through some CD's. This longer look confirmed my original thought, she had an amazing ass.

She eventually grabbed a CD and put it in the player. It was John Legend, "All of me." Interesting choice.

Turning, Vicki looked at me and started unbuttoning her top. "I'm ready to see if you're just all talk.?"

I walked to her and stopped her. I rebuttoned her blouse and told her, "We have a long time before we get to that."

That seemed to confuse her. "I thought you wanted to..."

"I do. But my mouth does many things to do besides just talking..."

I smiled at her confusion. "You said your roommate won't be home for hours. So, we are going to make the most of that time. We have about 2 hours so there is no hurry."

I looked into her electric blue eyes and gently held her chin. Then I lowered my lips to meet hers. I swear I felt a spark when our lips touched. She tried to slip her tongue into my mouth. Pulling my head back, I said "No. Not yet." And kissed her again. Raising my other hand, I held her head as I kissed her a third time. Her lips were so soft and sweet. Then my hands dropped to her shoulders and our kisses became firmer. I could feel my heart going faster and her breathing was going faster and becoming deeper. As my hands dropped to her waist, I pulled my head away from hers. She opened her eyes as if to ask why. I just smiled and said, "Now." Her tongue seemed to leap into my mouth. It was like she wanted to explore every inch.

Again, pulling my lips away, I kissed the right side of her neck using a little tongue. When my kisses reached her ears, I whispered, "This will be a night you'll talk about forever, but your friends will never believe." She moaned and dropped her head to my neck. My kisses started lower toward her shoulders. Without touching her breasts, I unbuttoned her top button which gave me more shoulder to kiss. The next button gave me even more and showed me the strap of her white bra (I wondered why she would wear a bra but no panties.). The third button gave me access to the end of her shoulder and allowed my tongue to slide the strap off her shoulder.

Her nipples poked through her bra like they were trying to escape.

Working my way back across her shoulder, I kissed Vicki on the mouth, and again we let our tongues battle. Then I started on her left side. First a little tongue kiss near her neck. Then further and further until the other strap slid off her left shoulder. There were still two buttons left holding her top closed.

Without taking my lips off her shoulder, I moved behind her. Then my kisses found new areas of her neck, her back and her shoulders to kiss. First her left side, then her right side.

Vicki moaned again.

"If you feel like this from me kissing her neck, how do you think you're going to feel when I kiss the rest of your body?"

"Mmmmmmm..." She couldn't even speak.

Reaching around her, I undid one more button while continuing to kiss her back and shoulders. This allowed her the top to fall from her shoulders completely.

"Drop your arms."

As she did, I unbuttoned the final button and let her top slide to the floor. I stepped back momentarily to look. She really was gorgeous standing there in heels, short skirt and white bra. But I couldn't stop there. Still behind her, I gently grabbed her chin, turning her head around to kiss her mouth. This time, my tongue made the first move. She sucked my tongue and then pushed it back into my mouth where her tongue immediately followed. Turning Vicki so we were face to face, we continued kissing while I undid the hook holding her bra. Since the straps were already around her arms, just stepping back allowed it to drop to the floor. I stayed focused on her mouth but could feel her hard now uncovered nipples press again my chest.

Again, I lowered my head to her right shoulder.

She tried to push my head lower. But I refused and whispered "patience."

Then I again kissed her shoulder and neck using the same tongue kisses but adding a little suck each time. I let my tongue trace her skin from her shoulder to her neck to her chin and finally, to her mouth. As before, my tongue attacked first. But I didn't stop there. Before her tongue could respond, I let my tongue trace the other side of her body from her chin to her neck to her left shoulder.

I continued kissing and sucking my way down to her left breast. Slowly I took her hard nipple into my mouth. I sucked on it and rolled it gently between my tongue and top teeth. All she could say was, "Mmmmmmm...that feels nice..."

Releasing her left nipple, I jumped back to her mouth and kissed her again. From there, my path was down her chin, to her neck to her shoulder and, finally, to her right breast. As before, I sucked her nipple into my mouth and rolled it across my teeth. Back and forth. Back and forth.

Her breathing was faster and shallower. She was almost panting. I could tell she was getting closer. But wasn't ready for her to cum yet.

Her hands reached for the top of my head and began to push my kisses down toward her stomach. But I didn't use my tongue to trace a path, kneeling I kissed and sucked every inch for her chest lower and lower until I reached her stomach. I could feel her hips push forward as her hands pushed down on my head. I grabbed her hands and held them as I kissed back up her body. When I got to her neck, I kissed her ear and whispered, "Not yet. Remember we have plenty of time."

Then I kissed my way back to her stomach and let my tongue attack her navel. All I heard was "Yes."

Then I kissed my way down to the top of her skirt. Vicki tried to lift the hem of her skirt, but I pushed her hands away and kissed around her waist toward her back. When I reached her spine, I slid my tongue up her spine licking to the back of her neck.

"Mmmmmmm..." she said with a shiver.

From her neck, I moved to kiss each shoulder and each shoulder blade as my hands reaching around and cupped her breasts, rolling the nipples between my finger and thumb. After suck-kissing each shoulder, I slid my tongue back to her spine but slid down this time as my hands slide down her body to her legs just below the bottom of her skirt. When my tongue reached the top of her skirt, I slid my hands up the outside of her thighs and reached under her skirt squeezing her firm ass cheeks. Without stopping the kisses, I said, "you are absolutely gorgeous." I had to say it twice before it registered with her, and she moaned in response. As she stood there in just her skirt and heels, I wondered if Michelangelo ever sculpted a better body.

Her ass was as firm as her breasts. My kisses paused briefly at her lower back and caused her to jump slightly. But I didn't stop. I lifted the back of her skirt kissed each ass cheek and slowly slid my tongue down the crevice between them. I kept my hands on her hips and said, "Turn around." As she turned, she stumbled and I used my hands to steady her then to lift her skirt while kissing each new inch of skin as it came within reach of my mouth.

When my tongue approached her pussy, she started to push my head toward the bare shaved lips, and she thrust her hips toward my face at the same time. But I stopped her. I stood and whispered in her ear, "Are you wet?" My hands were still holding up the hem of her skirt.

"Oh God, yes."

"Do you want me to lick you?"

"Oh yes, please."

"But I have been..."

"My pussy...please lick my pussy..."

"OK, but maybe you better lie down."

Vicki turned and headed for what I assumed was the bedroom.

"No, right here."

"In the middle of the living room?"

"Yes, right her on the floor in front of the window."

"But what is someone looks in?"

"They'll see you screaming and thrashing in orgasm."

I pulled a blanket off the couch and spread it on the floor. Then grabbed a couple of toss pillows and put them under her head when she laid down.

"Now, I'm going to start at your feet and kiss your legs like I kissed the rest of your body."

An "OK" was mumbled with disappointment. It was easy to see her legs weren't what she wanted kissed.

I didn't need to remove her open-toed shoes. But started kissing each toe on her left foot and moved to her shin. Then I raised her leg and licked her calf down to the back of her knee. When my tongue touched the back of her knee she shivered again, but longer this time.

Still holding her leg up, I licked the back of her thigh and slid my tongue toward the inside of her thigh and close to her pussy. Even though she tried to move my head in that direction, I ignored her pussy and kissed the inside of her thigh back up to her ankle. Then I switched to her right leg and repeated the process. She shivered yet again for an even longer time when I licked the back of her knee. When I got back to her ankle, I started to suck-kiss back and forth, the inside of each leg from her ankles to her thighs until I was so close to her pussy the lips were lightly brushed by my cheek. Vicki just exploded from that slight touch. Her orgasm seemed volcanic. The heat just poured from her body.

Lowering her legs pressing them apart by pushing the inside of her lovely thighs. I began kissing my way back up her body. I continued to her stomach and her breasts until I reached her neck. Continuing up to her right ear, I whispered that was only the first. She trembled in the aftereffect of the orgasm. I started kissing my way back down her body until I found her navel. My tongue fucked her navel as my hands slid up her legs and under her skirt. Fortunately, my attention to her navel was causing her to lift her hips off the floor. They were probably a foot off the floor in anticipation of further attention to her pussy which was shining with moisture.

I kept teasing her by licking the inside of her thighs until my tongue brushed her pussy lips and she exploded again in orgasm. If possible, even more powerful than the first. I continued to lick her pussy, teasing her clit to keep her orgasm going. My hands reached for her ass and held on while my face was buried between her legs. My tongue and cheeks were drenched. Vicki must have been going for 60 seconds or longer. So, I stopped and let her breathe.

Once she caught her breath, she managed to say, "On my God, that was amazing."

"Well, that was twice in one night."

"More like three or four...how?"

"If you enjoyed that, you're going to love this." And I found her rock-hard clit and teased it with my tongue as her hips continued to thrust up to meet my tongue. This time her orgasm seemed to be building like an incoming wave. I suddenly slid my finger into her dripping pussy as I sucked her clit into my mouth. The wave of her orgasm crested as Vicki came again and again.

Once again, I stopped to let her catch her breath.

"That must have been five and six."

"I've never had more than one orgasm before."

"And you're not done."

"What? I can hardly breathe."

"Then I'll go slowly until you get your breath back."

Still keeping my face down, I started licking her stomach while unzipping my shorts. I pushed my shorts off my hips and let them drop to my knees. Still licking Vicki's stomach and teasing her navel, I pulled my tighty-whiteys down which released my cock. I started kissing my way back up Vicki's body until my cock was near the entrance to her pussy.