Vine, Wine & Dine

"No way dude. If Jaydog thought for even a second I took cash from his family, he'd shitcan me in a heartbeat."

I looked at his dreads and tie-dyed shirt and gave him the best tip I could.

"Namaste."

"Right back at yah brother."

*****

Beth was a smart woman. She had excellent conversation skills and easily conveyed her thoughts and ideas. A true salesperson. In this case, real estate sales.

We shared many stories and drinks as the darkness of evening began to surround the stage and the light upon it started to shine.

"I love listening to live music, so much." Beth glowed as she spoke.

"So do I. This is a bit more mellow than I would normally go see, but it's the perfect night and I have the perfect company."

"Wow. Does that work often for you? I mean the smooth talk and flattery?" She could sense my embarrassment, but she kept going. "Look, I'm older than you probably think, but like you said, it is the perfect night. And like I already told you, I love live music. It makes me feel young and alive. So, you shouldn't be concerned about saying nice things to me. You're a handsome, gentlemen. I'm a horny old lady. So. If you want me, I'm a sure thing."

The 'sure thing' pressed her Chardonnay coated lips against mine. The tip of her tongue pushed until it snuck past my lips and teeth and found a dance partner.

With her arms over my shoulders, my arms around her waist, Beth molded herself to me as we swayed to the light sounds of the band she "loved".

Staying like this for two songs made me feel like a teenager at the Spring Social. Sneaking a kiss. Copping a feel. And not caring who was watching.

Finally, we broke apart. Stepping back, I looked at Beth for the first time. I mean truly looked. She was indeed a very attractive woman. Older than I would normally date, but my life as of late was not what any sane person would call normal.

"Aren't you too shy to be seen kissing an old lady in public?"

I laughed off her question. "No. I'm only concerned that I may offend you by poking you with my, shall we say, growing excitement."

It was Beth's turn to laugh as she spun herself into the web of my arms and settled in with her back to my front, and her ass pressing against my 'excitement'.

Under the cover of darkness and the false bravery created by alcohol, we threw our inhibitions in the air and watched as they scattered across the grassy park. To us, we were the only ones listening to the band. We were invisible to everyone and everything around us.

Beth pulled my hand up to her breast and held it with hers. She had my palm down so I could cup, squeeze, and massage her rock-hard nipple. While I was doing that, the cheeks of her ass cradled my erection as she slowly gyrated her hips.

"Oh, Chris..." Her ass doing a slow 'twerk' on my cock. "Touch me."

In my mind, I was touching her. She was humping my lower region with her ass, and I was groping her left breast like it was the first tit my hand had had the pleasure of touching.

Not wanting to adjust or change what was happening, I continued on with my current process, but shortly received another 'touch me', for my efforts.

For Beth, I wasn't moving fast enough.

The hand holding mine to her tit moved away. She opened the jacket she was carrying on the other arm moved it in front of her. With the jacket, her arms, and the small purse, she made a makeshift curtain.

"Touch me," she told me for the third and last time. From the sound of her voice, it wasn't a request.

The fingers of my right hand snaked their way under the stretchy waistline of her capris. I could immediately feel the warm of her smooth skin and the heat of her lower oven.

With no panties or other underwear to impede my movement, I eased my fingers lower while biting the side of Beth's neck.

My fingertips touched a patch of soft curls and stopped. Beth parted her legs widely and gave me an open invitation and ample access. She wasn't about to say 'touch me' again.

Warmth and moisture oozed from somewhere deep beneath the shroud of her unseen lips. Her "Ohhhhhh" was louder than the music being played in front of us as my middle finger parted her sex and easily sank in as far as it could possibly go.

I worked her lips and clit with a single digit until I felt the time had come for a second.

"Gaaaawd damn it. So good." Her words filling the night air. Maybe those nearby assumed she was talking about the band.

With two fingers moving inside of her, I circled my thumb over the meaty nub of her clit. Long strokes, short plunging bursts of speed and firm pressure. If it hadn't been for the music filling the air, her moans would have been undisguisable.

Like before, Beth's hips swayed and moved to the music. Unlike before, one of my hands was buried deep in her crotch, while the other held her throat as her head tilted back. Her mouth was wide open as she looked skyward.

The bucking and thrusting came on quickly. Her pelvis betrayed her. It moved on its own. I knew she was about to scream, so moving my hand from her throat, I covered her mouth with a clamp like grip. I could feel her screaming from somewhere deep inside as she exploded with an orgasm.

Beth's body shook with little spasms as she came down from her climax. We had gone from crazy movements to absolute stillness as she, or perhaps we, regained our composure. Slowly and sloppily, I eased my fingers out of her and pulled them up her belly until they were out of her pants.

At the start of the day, we had never met, nor did we know one another's name. Now, her head was leaning back, resting on my shoulder while my hand, covered in her sticky, sweet lady juice, rested on her belly.

"You ready to go?" she asked over the music.

I nodded in agreement. Unsure if it was due to embarrassment or something deeper. I didn't have to wait long to find out.

With no one in the parking lot, Beth tore at my pants like a starving woman opens a bag of chips.

"Beth, I should probably wash-up first. I haven't had a shower since this..."

My words didn't matter.

Her lips and mouth covered my cock in a flash and with five or less bobs of her head, I was deep down her throat.

Everything about her blowjob was like her. It was perfect and professional. The correct amount of moisture and suction as she worked me toward the endgame.

I gave fair warning. I told her I was close. I rubbed her cheek. I complimented her on technique. I tried to hand on as long as possible, but Beth went harder, and deeper.

Gagging, spitting and coughing, she sucked and worked at me until I filled her mouth with a pent-up load of semen.

Without the blink of an eye, she swallowed every drop. It was her commission for a job well done.

"I like the taste and smell of a real man," she told me as she kicked off one of her shoes and pulled a leg out of her capri.

Rubbing the tip of my still hard cock over herself, she mashed down until her thick meaty lips parted and allowed me in. Sinking deeply, Beth hissed and moaned.

"That's soooo..."

So what?

For where I was laying, it was great. Her pussy was giving my cock the massage of a lifetime and I had pried her blouse and bra up, releasing her ample breasts from their prison and into my mouth. They both smelled divine, but they each had traces of sweat and odor from a long day of confinement.

Beth was experienced and knew what she wanted.

Cooing and purring while I suckled at her nipples, she pulled up until just the tip was left inside her, then she dropped down until she bottomed out with a grunt.

The slow love making started to speed up. Beth wasn't going to wait very much longer. In the beginning, she was doing most of the work. It was how she wanted it. But by the sound of her breathe alone, I could tell things, had now changed.

"Chris, can you get on top?"

Without so much as an eye blink, I rolled her over and remounted.

"Hard...as hard as you want to give it to me."

What had earlier been soft and somewhat quiet grunts were now full-on grunts of hard love making. Groans and semi screams filled the van as I rammed into my lover time and time again.

Her hands clawed at my hair as she tried to pull my face down to hers.

Air escaped her and blew in my mouth as she grunted.

"Hard...make it...hurt me. Make me sore. Make me pay for my sins."

"You like that baby? You like when my cock tries to split you in two?"

There were no words. Just groans as she pressed her lips back to mine and blew warm air into my lungs.

I could feel the hard floor working at my knees. Rug burns would be a sure bet. It gave me concern for the well being of Beth's back and ass, but not once did she complain. Instead, she thrust her hips up to meet my every pump.

Reaching between our bodies, I cupped one of her fine tits and gently pinched and twisted her large nipples.

"Fuck..."

"You like that baby?"

Her head nodded as she grabbed the cheeks of my ass and pulled me deeper inside of herself.

"Good. Show me how much. Cum for me. Squeeze my cock with your tight little pussy and cum all over me."

"FUUUUUUUUUUUUUUCK."

The van vibrated and I wasn't sure if the window would shatter, but it didn't matter. Beth came and I followed her lead.

While her body quaked and tried its best to ease back into a state of normalness, I filled her with a blast of semen I wasn't sure I still had in me. It brought out another groan and coo. I immediately remembered why I loved these tours.

*****

Sweaty, dirty and disheveled, we pulled into the Westin.

Beth opened the door and was once again out before I could get around to her side and open the door. There was a look on her face. One telling me she was stuck was somewhere between embarrassment and regret.

My try at embracing her was declined.

"Chris, please. Not here. I can't let anyone see me with you."

There would be no kiss goodbye. No request to join her for a nightcap or perhaps another round of love making. No, all those things were put behind us when she stuck out her hand and shook mine.

"Thank you for accompanying to the concert Chris. You were a true gentleman, until I allowed you not to be. But you are the best tour guide ever, so I will be giving you a positive rating."

Her words made me chuckle and smile as I watched her walking gingerly toward the front doors of her hotel.

Seems, even though I was getting lots of opportunities with the ladies, none were going to stick. But the company approval ratings would continue to climb.

*****

By mid-July the trees and vines were laden with fruit which would be harvested in the upcoming months.

The heat was hovering close to a hundred degrees for the past week or so, but it was beautiful. So beautiful while waiting for clients, I would sit outside and gaze at the countryside.

There was nothing I would change about how my business endeavor was going with my sister-in-law. We were busy and making money. So busy, we had placed an order for a third vehicle.

I was reading over the purchase agreement on one such day when my phone pinged.

A strange text, from a strange number.

Hey sexy. DTF?

I knew what DTF meant. I just didn't know who was sending it. So, I waited for a while to respond. Longer than the sender wanted me to.

Playing hard to get stud?

Again, I waited.

WTF? I can see that you've read my text.

I thought I would try to narrow down the potential senders.

How soon can you be here?

The response was being typed as soon as I pressed send.

In Sacramento. Done at 4pm. Hour after? Say 5ish. Give or take.

Now I was completely fucked. Other then a couple of business contacts, I didn't know anyone in Sacramento. Well, you know the old motto, 'live large or go home'.

Where do you want to meet?

Your house, or should I get a room?

My place

It seemed simple enough as I texted what I assumed was a "her" the address.

*****

Six hours later, the white Ford Edge that screamed "rental" pulled up in front of my house.

With the driver's window faced away, I still had no idea who had come calling. That is until the door opened, and the wild mane of blonde hair came into view.

Jillian had shown up for a visit.

Throwing the overnight bag at my feet, Jillian leaped onto my body, wrapping her arms and legs around me.

"Miss me, Daddy?"

"I sure did baby. I sure did."

There was no lying in my words. I had missed her. I loved everything about her. Jillian was by far the best thing to happen to me since long before my exile from New York City.

"I can't wait to feel you in me, Daddy," she said through lips that were all over my face.

"Good, but let's take our time. We have all night."

"Boo..."

Her pouty face made her look years younger than she was.

Uncertainty hit me like a ton of bricks. Was tonight only a booty call, or was it something different? Something more. A date? Maybe. Either way, I planned on making it memorable.

At 42 years of age, I felt I was well versed in the art of seduction.

I kept my home clean and modern. I had knowledge in the wine department, and I could hold my own in the kitchen. And if those things weren't enough, I could easily hold a conversation with most people.

So, this evening, I planned on pleasing Jillian.

Keep it simple was a constant reminder for me. Stay with things that work.

Scallops for a starter. Mixed greens with strawberries, goat's cheese and a light raspberry vinaigrette. Fingerling potatoes and a medium rare filet mignon. Orange sorbet for dessert.

"Jesus Christ, Chris. Remind me why you didn't tell me you cooked like this the last time I saw you?"

"If I recall correctly, you had provided me with a list of tasks, and cooking for you wasn't on said list."

"Maybe not, but if I knew in advance, I might have eliminated one or two of the lesser needed items and went right to that steak."

"Really? What would you eliminate? The lingerie? You know how hard it made me, seeing you in it."

Her head shook. "No. I'd keep it. It makes me feel sexy and I liked when you went down on me while I was wearing my panties."

"What about when I was deep inside you? Or when I was chewing those perfect little nipples of yours. Maybe we could have a salad instead of doing those things."

Again, she tossed her golden mane from side to side. "As much as I love dinner, I love doing dirty things with you, more." Her shy smile was infectious.

"I see. Can you imagine what our next meal will be like? If I did this for you, and you have only treated me like an escort. After what we do tonight, the next meal will make this one, taste like McDonald's take-out."

Jillian moved closer to the table. Putting both elbows down she laced her fingers together and rested her chin on them. The way she was looking at me caused me to stir in my pants.

"That comes across as a challenge. What do you have in mind Daddy?"

"Nothing too spectacular. Maybe some time in the hot tub. Open a bottle of something you like. No drying off. Instead, I lick the moisture from you. Then a hot oil massage. One where I rub every inch of your perfect pale skin. Your neck and back. Those long lean legs. That glorious ass."

"Glorious?"

"Shhh...it's my fantasy. Relax and go with it."

"Okay, Daddy.'

"Your ass. Your firm, perfect ass. I save the warmest oil for it. I pour it directly into the crack at the top and watch as it glides down. Going in both directions. It runs down your crack and over your tiny asshole. And it flows the other way. Up your back to those cute little dimples above your ass cheeks. Then, while you're relaxing, my hands and fingers work at the hot oil. They try to keep up. They try their best to massage it into your soft skin. But there's too much. Maybe I lean into you and rub my chest over your ass."

"Mmmmm...."

"You like?"

"No, I love."

"Good, because it doesn't stop there. My fingers are soaked with the hot oil. And the oil has a mind of its own. My hand slips. It makes a wrong move as it glides down the sweet crack of your ass. The tip of my finger feels something that it hasn't felt before. A piece of crinkled skin. Puckered and hiding something beneath it. I push my oily fingertip into it. At first there's resistance. But only for a short time. Then, from out of nowhere, your hips lift off the bed. You're pushing your puckered bum hole up to me. You want my oily finger to sink into parts unknown. I press it forward and into you. I happily oblige you."

"Ohhh, yeah." Jillian's hips were moving on the chair under her. She was grinding her lower parts, yet her cradled hands still held her head and her eyes had never left mine.

"Yes, baby, open up. Relax and let me play with your tight little bum hole."

"All right, stop. I get it. Stop."

Jillian stood and looked around the room. Her fingers worked at the pearl white buttons that held her blouse closed, but they didn't stand a chance. In seconds her lacy bra was exposed to me and shortly after, her pants lay on the floor beside her blouse. I knew she wasn't joking when she asked, "Is the hot tub ready, because I am."

*****

Our time in the hot tub was spent reacquainting ourselves. Lots of foreplay. Long wet kisses, with soft bites and nibbles. Hands and fingers exploring, touching and probing, accompanied by the whispered words of lovers.

After some time, the warmth of the water and our passion became too much. We were overheating. It wasn't necessarily from the water temperature, but both came with the state of sexual arousal, and we needed to be somewhere else.

Naked and wet, Jillian followed me down the hall to the spare room. She laughed when she saw the bowl of steaming water holding a tube of oil.

Surprisingly, she didn't flinch at it. Instead, she jumped on the bed face down, pulled two pillows under her chest and rested on her elbows while I prepared.

"You do this a lot, Daddy?"

"Actually never. Seems I've been saving it for the sexiest girl I know."

"You think I'm sexy?"

"I know you are."

A screaming laugh filled the room as I poured a generous amount of the warm oil over her back and butt.

Staying true to my words in the kitchen, I did all the things I told her I would. The massage of her neck, arms, back, and legs put her in an erotic trance, but when I started on her ass and let my finger glide over her ass for the first time, I had her full attention.

Everything about the massage was soft and relaxing, right up until I pressed my finger into her ass. It was well oiled and using the proper amount of lubricant made it easy to sink in. It all seemed to be going smoothly until Jillian flipped her long blonde hair and looked over her shoulder. She watched as I pulled off my pants, released myself, and used my left hand to oil up my cock.

"It's too big Daddy. You'll kill me if you try and put it in."

My lips kissed her oily ass and followed the trail up to her lips. Our tongues battled as I pulled my finger out of her ass and replaced with a stacked pair.

"Fuuuuuuuuuuucccck. That feels soooooo..."

I pressed my mouth over hers so she could not speak.

My fingers moved slowly in and out, trying the stretch her tight little asshole. For minutes, we stayed in the same position. Kissing and fingering her ass.

Finally, the time had come. She wasn't ready, but I was.

I pulled out my digits. Lifted her hips and put a pillow under her so she was more or less on her knees. Then I rubbed the head of my oily cock over her puckered gateway. I pushed forward, and to my absolute amazement, she pressed back.

With a plop, the mushroomed head of my cock disappeared into her asshole.

I watched as it slipped in. Deeper and deeper the glistening shaft dove until it couldn't go any further.