Vine, Wine & Dine

Jill and one of the other girls gave me the once over.

"Wow. Are you part of the package? Nice suit. Is it tailored?"

The blonde liked my look. Blue Hugo, white shirt with only a single top button undone. Accented by matching cognac leather shoes and belt.

"Very sharp, Limo Man."

She didn't let up on the flirting, and I didn't mind.

Of the three ladies already outside, she was easily the best looking. She appeared to have a very nice body, and her ass was top shelf with the cheeks peeking out from the leg holes of her shorts.

"Thank you, Jillian. Not so bad yourself."

I grinned. Teasing on my end was part of the deluxe package.

The first of the group were just finishing getting into the van when the next part of their gang came out from the main entrance.

I noticed two things immediately. First was, all these girls had matching outfits on. Jean shorts. Open plaid shirts with a white t-shirt under it, and short cowgirl boots. The second thing I noticed was, one of them had been crying.

"Ladies, the cooler in the back is full of refreshments. Help yourselves. We are about fifteen minutes from Stag's Leap, it's the first winery on your list of must do's. If things go well, we'll visit a few additional places you may have never heard of. They're on the smaller side, but they might surprise and interest you. Off the beaten path, but very fun."

With no questions, I closed the door.

Putting the van into gear, I pulled onto the main street and headed toward our destination. Regardless of how good looking a few of the girls behind me were, I kept my eyes on the road, but my ears were wide open.

The guest of honor got into the back row with her sister and the two in the first row provided the gossip.

"He's a dick."

"He treats her like shit."

"No, he lied. He's going golfing and to some strip club in Canada. Yeah, that kind of club. The one where girls take everything off and...you know."

"She told Jill he called her a fat ass."

"No. I'm not kidding."

"Oh, she's definitely lost all of her confidence in herself."

"We need to get her laid."

It was a rapid-fire conversation going back and forth, and I had no idea who was speaking. But I hadn't missed much of the gossip.

I dropped the all-girl crew off at the famous winery's front door and moved to the parking lot in search of a shady tree to park under. I did the same thing three more times over the next couple of hours.

*****

All my life experience has shown that alcohol has a funny way of loosening up the hardest of people. Today wasn't the exception. It showed when Stacey got back into the van and had let someone write "August Bride" on her t-shirt in black marker. Yes, the girls in my care were getting more outgoing, louder and a bit crazier with each stop. They talked and yelled more and more. They started doing strange girl things like tweaking nipples, poking boobs and slapping each other's asses. They wanted the music louder, and the refreshment cooler opened and closed every few minutes.

"Hey Limo Guy, you gotta wife?" a brunette from the second row asked.

"No. I do not."

"Girlfriend?" she shot back instantly.

"Unfortunately, also a no."

"You want six of them? We're here until tomorrow night, and a couple of us are pretty easy, but you'd have to guess which ones." She screamed in laughter along with her friends after she finished her tease.

"I'm sure I couldn't handle six women as beautiful as this group." I played along.

Their volume of their roars increased.

At times, because of how loud they were, it was hard to recognize voices or who was speaking. But when three of the girls opened hard ciders and chugged them, I heard Jill clearly say, "You know cleaning up puke comes directly off of the security deposit, right?"

Luckily the next stop was a slower paced wine pairing. And it came with a full lunch. Hopefully it would help slow the pace of the current race to be hammered the girls were in. The conga line of girls laughed all the way into the old brick winery.

It was break time for me, so I parked, took off my jacket, and opened a cold iced tea. Unfortunately, my break was short lived.

*****

I watched Jillian walking across the stone parking lot. One foot in front of the other as she headed my way. She was trying her best to look sober, and with the sway of her hips, it appeared as though it was her weekend off from the catwalks of Milan.

Like I had told myself earlier, she was easily the hottest of all six girls, by a long shot. The others were not ugly by any means, but Jillian was a fox. Nicely proportioned body, with ample bosom, a small waist, and the perfect sized hips and butt.

"Holy shit. It's hot as hell in there," she said as I closed the sliding door behind her.

Leaning back with her head on an armrest and her legs stretched as far as she could, she fanned herself with one of the wine tour magazines in the van.

"Are you alright Jill?"

I didn't wait for an answer. Instead, I opted to get her a cold water out of the cooler. This beauty was pretty messed up. I imagined it was the heat of the kitchen they were tasting food in, and it had nothing to do with the large amounts of red wine and other booze that she had consumed.

"Thank you," she said quietly as I handed her the icy bottle. Within seconds of hearing her drink some of the water, I could hear sniffles and sobs. Part of this gig wasn't me playing Dr. Phil, but like an idiot, I asked anyway.

"Is everything alright Jillian?"

I looked back in time to see her put the frosty plastic bottle into her open flannel shirt and rub it over her cleavage.

"Yes," she said through the sobs, but she meant "No."

Deciding to not to perv on a drunk girl's breasts, and let a sleeping dog lie, I turned and faced the building.

"It's just worry...I'm worried about Stacey. She's getting married in twelve weeks and let's just say the Stapleford women don't have the best track record when it comes to man."

I put my hand over my mouth when Jillian spoke. In my mind, I imagined someone with a lisp having to say Stacey Stapleford, three times fast.

"How so?" I couldn't believe that I was asking.

"Our father is the perfect dad, and my mom tries her best to drive him away. I can't keep a boyfriend to save my life. They stay away from me like I'm a zombie. And poor Stacey. She has no idea what happiness is. She's marrying Paul because he has a good job. The asshole works for his father. He has a good job, but he treats her like shit. Fair trade off, don't you think?" She held the rest of the cool water to her forehead. She hadn't moved an inch, but she kept talking.

"I know what he's like. He's shitty in bed. I mean both Shannon and Britt have slept with him. I think she likes...I don't know? He may be a dick, but at least she has someone...I guess."

When she said the girls' names, I instantly recognized them as girls in the van with the group. Jillian mumbled something else in a wine induced language, then clearly said, "It's been so long, I'd probably let the asshole fuck me."

And that was it. She slept for 45 minutes until the merriment of her crew woke her up.

In a top secret move, I handed Jillian another water and a Red Bull. Maybe it would help her regain some composure.

The next stop was just over ten minutes away. When the van stopped, the screaming group piled out and headed inside. It was one of the stops that I had suggested. It was a small batch place. Off the beaten path, so it had a lot less traffic, but the quality was top notch.

Twice while entering, Jillian looked over her shoulder at me, giving me a look like she was concerned about me going through her purse while she was distracted.

I parked the Benz under the shade of a California Sycamore and listened to the wind rustle large leaves as the branches danced slowly in the breeze. My mind was on a number of other things as I collected empty cans and bottles, made sure there was plenty of ice to keep the drinks cold, and confirmed the cooler wasn't in dire need of a restock yet. This group seemed to be giving it a workout.

"Chris..." The sound of Jillian's voice scared the hell out of me. She had snuck up behind me without making a sound on the gravel parking lot.

"Hey Jillian. Are you lost?" I asked with a chuckle.

"You gotta stop calling me that. Please, call me Jill." She looked down at her feet and subliminally moved a stone around with the tip of her tiny cowgirl boot. "No, I'm not lost. I was just..." She paused and looked up from stones. "Well, I was, or I guess, I am, wondering if you might do me a favor."

"I suppose. That's what I'm here for, right. This weekend is about your group, so what can I do for you?"

"The girls and I were talking, I mean, we came up with a plan, in general. We planned on getting someone else until we met you. And, when we saw you, we decided to actually try to go through with it. I...I mean we, would like you..." after some hesitation, her eyes focused in on mine and she told me exactly what they wanted. "We want you to fuck Stacey."

My facial expression must have said a lot.

"Not for free. No. No. Not for free. We'd pay you. We each pitched in fifty bucks a piece. So, you make like two fifty. All we ask is that you try to make her happy. You know, try to please her." I watched her lips as she said every word.

"Jill, I'm flattered by your offer, but, well excuse me for being cautious, but what makes you think Stacey wants something like this? And what makes you think I moonlight as a gigolo?"

"She doesn't know what she wants, and it's her biggest problem. And you're a guy. Guys do things. Most guys I know are willing to make a few bucks on the side. Especially the kind of guys driving a bus for a living," Jill said matter-of-factly.

"Is that so? You buy lots of sexual favors from bus drivers, do you? My first impression of you was you're not the kind of girl that has to pay for sex very often."

"What? I'm not paying for me. I...I can get laid...I can...I have lots of guys who are more than willing to do it for free." She shook her head as if doing so would convince me. "I've never paid for sex. No...I'm..."

"You're what. You never have to pay for sex, yet you stand here offering to pay me to sleep with your sister. The bride to be. Does she know about it?"

"Of course not." Jill said.

"So, me trying to have sex with her could be problematic. What if she doesn't want to, or what if she turns the tables on the group? Maybe she adds another fifty bucks to the pot and asks me to sleep with you? She told me it's been so long since you've been with a man you may have forgotten what it was like." This was getting to be fun. It could be bad for business and reviews, but it was fun.

"How the...what...who told her. Did she tell you I couldn't find...? What, did she say? Nobody knows how long it's been since...I. Were the girls talking about me?" Her body tensed up into a fighting stance.

Her breast rubbed my shoulder as she pressed past me and reached into the back of the van. Opening the cooler, she pulled out a can of hard cider. I'd bet she downed a third of the can on her first gulp.

The soft flesh didn't touch me on the way back, but it didn't stop me from staring at her cleavage.

"Tell me who said it?" she demanded. "What was said?"

I don't know why I didn't put an end to it. It more than likely had something to do with the callous way that Jill assumed I'd jump at the $250. I had seen lots of women like her during my time on Wall St. Money and power does funny things to the mind.

"I was driving, so I don't know who was talking, but I remember someone saying things were tense for you at work, and you have been without a boyfriend for a while, and they thought there wasn't tons of time to pleasure yourself, because of your busy schedule." It was all made up of course, but it was a bit of payback.

Jill rolled her bottom lip around between her teeth. She looked at the stone building of the winery, down to her phone and then back at me. She was becoming impatient.

"I have the money on me. Are you going to do it?" The toe of her boot kicking rocks as she moved her foot too quickly.

"No. Stacey is a beautiful young woman, but..."

"What about me?" Jill said.

"What about you?" I questioned.

Her head was looking back at the building, she drew in a deep breath and turned to me.

"If I added the fifty like you said, would you do me?" There was zero mistaking what she asked.

Like Jill, it had also been a long time for me, and I could instantly feel the stirring in my body as I thought of her naked body moving under me.

In front of me was a beautiful woman, in her mid to late 20's. In her sexual prime. Asking me, a 42-year-old guy who she knew absolutely nothing about, to have sex with her for money. At any other time, on any other day, I would have laughed and walked away. But right there, right then, with the breeze blowing the scent of mustard flowers through the air, I pondered the feeling of being with her.

I looked at my wrist, pulled up the white sleeve and read the face of my watch.

Wanting to toss 'I've never paid for sex' in her face, I instead opted for, "As tempting as it sounds, we only have about twenty minutes and they'll be done here."

Jillian spun on her heels and walked away. I watched the cheeks of her firm ass jiggling under the short cutoffs as she left. I felt relief and disappointment all at the same time.

Those feelings of disappointment were short lived. In minutes, the tiny blonde was walking back toward the van. Focused and alert. When I looked down at my watch for the second time, I noticed that only seven minutes had passed by.

"Here." She handed me a wad of rolled bills I wasn't about to take.

"Jill...I" She wasn't having any of it as she tucked the bills into the pocket of my shirt. I needed to think fast, so I went with time. "As much as I want to, we have less than ten minutes now."

Her fingers had already unbuttoned two of the top buttons on my shirt.

"I ordered a charcuterie board for them and a full round of drinks. Unless you're Superman, we have lots of time." She finished by pulling the tails of my shirt out of my pants and looked at me. "Well?"

It was my turn to check the parking lot. I had parked in the back corner of this lot a dozen times without any company bothering me, and I didn't want today to be the first time for it to happen. When I saw that the coast was clear, my hands touched Jill for the first time.

My fingers undid the rodeo style belt buckle attached to her shorts for show. Then I undid the button on her short 501's and slid my hands in only deep enough so they could take ahold of her white cotton muscle shirt. Pulling it out, I returned my hands so I could cup the sweet ass I had been checking out all day.

Jill moaned as my fingertips squeezed her bare cheeks

"No panties. Did you plan this when you woke up today?" I teased.

"I took them and my bra off when I freshened up inside a minute ago." Look at her. Thinking ahead for me.

When my belt opened and the zipper of my pants lowered, I was so hard I basically popped out of confinement. My cock spilled over the top band of my underwear and landed in Jill's hand.

"Oh...nice," Jill cooed.

I could have used her exact words as the tips of my fingers found moisture as they dredged between the cheeks of her ass and came to rest on her hairless pussy.

With the back doors opened straight out, they acted as metal screens to keep would be gawkers at bay, and with only rows and rows of grapes behind us, we felt free to do what we wanted.

"Arghhhhh." Jill's body started to betray itself as I pushed my middle digit up and into her sopping wet vagina.

We were standing in front of one another. Her tugging my hard penis and me fingering her wet pussy, and yet we had never even kissed, and at my age, kissing was something I enjoyed very much.

Lifting one hand off her ass cheek, I moved it up and pushed my fingers into the silky mass of blonde hair. She knew exactly what I wanted when I pulled her head toward mine.

Jill's puckered lips found mine. They had a taste of strawberry and lemonade.

"You don't want this. Not here. Not like this." I whispered as a warning.

Her, "but I do", breathed into my mouth with a blast of warm air.

I gave fair warning. I offered to be a gentleman. But as I pushed her back into the carpeted cargo area of the van, dropped to my knees, and sank my tongue into the wet furrow of her meaty pussy, I put those things behind me.

"Yessssssssssssssssssss." Jill's fingernails raked the bare skin of my shoulders as I tasted every inch of her womanhood.

Using my fingers to hold open the folds of the dark meaty lips in front of me, I lapped up the juicy gift flowing freely from my new blonde friend.

Understanding what she had said earlier, was going to be difficult. I found it hard to believe Jill couldn't find a lover, because as I once again slid my tongue and finger into her dripping cunt, I was amazed at how beautiful she was.

"Ohhhhh. Please make me..." Jill's hips lifted off the carpeted flooring and pressed against my face as I rapid fire flicked her rock-hard bean.

She went silent, but I continued my tongue work. Flicking, licking and sucking. My younger lover's body shook and convulsed, but she made no loud sounds. Her hips moved and bucked as they fucked my face, but the only thing I heard was the rustling of leaves. Until she reached her climax.

"Gaaaaaaaaaaaaaahhhhh." Her huge gasp of air was loud enough to alert anyone in the parking lot, but luckily, we were still alone.

My mind told me to stop while I was ahead. Jillian's scream hadn't caused any grief, yet. But it might if we kept pressing the issue. The smart thing would be to have her pull up her cutoff shorts and for me to tuck away my dick, but as I rubbed the pulsing mushroom head over to wetness, I knew stopping wasn't one of the options I liked. So, I pushed forward.

"Fu..." My hand covered her mouth before she could really start, or finish. I pressed forward again until I hit bottom. I was in as far as I could go, and as the silky insides of her womanhood caressed and hugged my shaft, it felt like it had been forever since I had been with a woman.

"Hard and fast or soft and slow?" I removed my hand from the mouth biting the palm of my hand, after I asked.

"Do whatever you want to me."

"Fine. I have no problem taking the lead, but remember, you're the one that's paying."

As she thought about it, her hips had already started moving when, "hard and fast" escaped her.

I liked the sound of her answer for a couple of reasons. One was, I wanted to cum so we could lessen the chances of getting caught. The second was, if we finished and got off quickly, we might have time for round two.

As much as I wanted it to be hard and fast, it ended up being somewhere in between. I pulled out until the tip was at risk of popping out, then I eased it back in until my balls came to rest on the cheeks of her ass.

Hands full of her naked tits, I kept doing what we both wanted and needed.

"Fuck daddy, it feels so good. You like it? You like fucking my young pussy?" Jill teased as she fucked me back.

"I do, and I'm going to give you all the old 'Superman' cock you can handle," I told my little vixen as I ramped up speed.

The first 30 or 40 strokes had been gentle by comparison to the next round. My balls now slapped Jillian's ass when my cock smashed into her cervix. The soft cooing sounds now became loud grunts of pleasure as her eyes rolled back and closed. Mouth open, I slid the same finger that had been in her pussy, into the open hole until it touched her tongue. Her lips immediately closed around the still wet digit. If she sucked cock with nearly as much attention as she did my finger, I couldn't wait.