Vine, Wine & Dine

Jillian was a trooper. Her head was buried in the pillows in front of her. Her fingers clawed at the linen bedding and her knees shook with excitement and anticipation. She let out a very loud moan as she waited for me to move.

My hands roamed her ass and came to rest on her hips. I didn't pull or push. In fact, I didn't even move. I wanted it to be her who started things going.

"You tell me when baby."

"When..." Her squeaky voice escaped from somewhere inside of the pillow.

After a dozen slow and gentle thrusts, Jillian lifted her head for the first time. She looked back at me and tried to smile.

"So full."

"Am I hurting you?"

She shook her head and grunted out, "No, but I can't understand why anyone would want my asshole when I have a perfectly good pussy."

"Stop making me laugh, I'm trying to cum for you."

Jillian could have said no. She could have told me anal wasn't her thing, but for me, she was willing to try it. She wanted to make her lover happy, even if it were at the expense of a sore butt. So, she started doing the things she knew would end it quickly.

Her ass clenched tighter. Her hips moved in longer motions. Her hands took turns reaching back. Touching my arm and hand. Cupping my balls and scratching at my side. And she did what she knew would set me off.

"Fuck Daddy, your big cock feels so good in my little ass. Fuck it. I know you want to fill it with your hot load. Please Daddy, put some hot cum in me."

My fingers held her hips tight as my head tilted up. I was pumping harder than before, but my lover was okay with it, because she knew it was almost over. She wanted it to be over, so she tried to speed up the process.

"Oh, you dirty bastard. Fuck my young ass. Make me your slut."

I could feel my balls tightening as they prepared to erupt into Jillian's ass.

"Does it turn you on to know you took my ass cherry, Daddy? Does it make you horny knowing you raped my bum?"

There it was. The one to carry me over the edge. A load of molten lava blasted from me like l couldn't remember. I screamed as it shot out of me. Jillian screamed as it shot into her. My cock was filling her bowels with a load of warm goo.

Collapsing onto her back, my arms embraced her body and my lips nuzzled at her neck. I wanted to stay in this moment until the end of time.

"Chris. Baby. I'm sorry, but you have to pull your monster out of my ass."

I jumped in shock when she spoke. The words brought me back to reality and I started to withdraw myself.

"Gingerly, please."

*****

Darkness surrounded us. We had dozed off from our earlier bout of sex. My body could feel the warmth of Jillian's naked skin touching it. I would have stayed like this until morning, but I needed to pee.

"Where are you going?" her sexy, sleepy voice asked.

"I have to pee. Then I'm going to have a shower."

"Okay, as long as you don't sneak out on me like you did last time."

"I didn't sneak out. You passed out from your booze intake, and I left."

"Sure. Either way, I woke up alone."

"Well, you have my word it won't happen tomorrow."

"Good. Can I join you in the shower?"

She didn't wait for an answer. I could see in the shadows that she was getting up. So, I held out my hand and pulled her to me.

Showering with a woman, one who is your lover, can be one of the best things in life. Washing, cleaning, dirtying, re-cleaning, it's a great pastime.

I washed Jillian's hair and soaped her up to rid her smooth skin of the oil I had used on her earlier. In turn, she soaped and rinsed every inch of my body, and paid special attention to my penis.

"I have to be sure it's clean before I put it back in my mouth."

We made tender slow-moving love under the warm stream of falling water. My cock found a home in the depths of her smooth, creamy pussy and it tried to stay for as long as it could.

The love making only took breaks for refreshments and talk. Jillian told me her life story, and I told her a very brief overview of mine. I don't remember when, but sometime during the cool California night, we ended up naked under the covers of my bed, watching the cosmos, counting the stars filling the black sky.

*****

"Stay." I told her as I stirred the scrambled eggs and cut up some fruit.

"I can't. My flight is at noon, and I have a pair of reports due in the morning, and I have an online board meeting tomorrow night."

"So, I guess the trend continues. You come to Napa, use and abuse me, then leave me all alone."

"Abuse you? Really? Does your asshole still throb this morning?"

I looked up from the kiwi I was slicing and smiled.

"I offered to kiss it better."

"Yeah, well, come to Baltimore and you can kiss it better anytime you feel like it."

"What the hell would an old guy like me do in Baltimore?"

"Go watch the Orioles play. Seems to make my father happy."

"You better be careful young lady, or your sore ass might get a slap or two on its sweet cheeks."

"I'm not kidding, come to Baltimore."

Jillian's eyes looked at me and for a second. I was concerned she thought I was serious about spanking her, but there was something else. Something she wanted to ask.

"Chris..."

"Jillian..."

Her eyes squinted and her nose curled.

"I'm not kidding, you keep calling me Jillian, and I'll cut your dick off, and we'll both have to do without."

"Sorry...Jill."

"Better." There was a bit of hesitation, but it was short lived. "Chris, would you be interested in being my plus one at Stacey's wedding?"

My answer didn't come fast enough for her.

"I understand. I mean, I guess you have lots of other opportunities. We're just, well you know, friends. We are right? Friends, I mean. Besides the benefits part. Are we? I'd pay for your ticket to fly out."

Walking over, I laced my fingers into her still damp blonde mane and tilted her face up to me. I gave her a soft kiss and looked into her eyes.

"We are friends. And we are lovers. Jill, you are the sexiest thing on this earth, but you just don't know it. I'd be honored to be your plus one, but why would you want an old man as your date?"

"Eleven years. You're only eleven years older than me. And you treat me like a princess. I mean when you're not raping my ass."

Her damp hair and light tears left a wet spot on my white shirt.

We had breakfast and dressed for our day. She was flying across the country, and I had a day of tour giving. So, with a long, wet kiss of a good-bye, we went our separate ways.

*****

All the details were ironed out. The wedding was on August 12^th. Jill was in the wedding party, so her dress was a yellowish color. I would be wearing either brown or black to match. I had an address in hand and would be meeting her at the church. I would have arrived earlier but there was a change of events in my life.

After almost eleven months to the day, The Banking Commission released their findings. I was found not guilty and cleared of any wrongdoings. All my assets were freed up and once again at my disposable. I was free to trade again. But in those months, something had changed. I had changed. The world had changed. I wasn't sure I wanted to fall back into my past lifestyle, but I did miss the bright lights and the big city.

My old company set up a meeting. It was the day before the wedding. A day where once again my life might change.

*****

I was ushered into the offices and rushed down the carpeted runway. It was like I was being shown off like a prize hound at the Westminster Kennel Club Dog show. Passing by all of the would-be judges, I kept my chin up and head held high.

The scene was one I had watched before. Like the others, they paraded me through the gauntlet and grinned as I was escorted to the boardroom. I could hear the whispers coming from behind the partitions of those who, like me, had fought and clawed their way into an office. An office like my old one. The one where many, many millions were made for this company. The one that was now occupied by a strange face. The face having no idea of the dealings and deals made behind those closed doors.

They, every single one of my judges, watched in worry as the door closed behind me because they knew their day would come soon enough.

*****

The large boardroom seemed almost empty.

The three senior partners and the company legal team looked at me and nodded. The President gave a "Christopher" as a greeting, but there would be no shaking of hands. No congratulations. No welcome backs. This was a different meeting altogether.

"So, Mr..."

"Chris. Just call me Chris."

"Fine, Chris. On behalf of the company, we are very pleased with the announcement you have been cleared of any wrongdoings. And considering the event of your..."

"Stop. The only reason any of you are pleased, is because it clears you and your company. Enlighten me with your plans for my future. I can see you've filled my office, so just get to it. We can haggle a bit, but in the end, you know I hold the Royal Flush. I have retained any and all of the information of every single call, conversation and trade made by me and all the others I was involved in. Toss me to the curb again, and I'll be the one making calls. It might be fun watching some of your houses going up for sale in the Hamptons."

"Are you threatening us you little prick?"

"No, Evan, it's a fact. And you might want to ask your wife about the 'little prick' thing."

It was an unnecessary shot to take, but the meeting was pretty much over at that point. Evan wanted me out permanently and the niceties had been kicked into the wind. Now all there was to do was argue over severance.

After three breaks, one of them being for lunch, pen was put to paper. It was agreed I would have a pay continuance of five years; plus be reimbursed for my time missed. Company perks and benefits included. No profit sharing or no commission from past accounts, just base salary.

But the cherry on top of the deal was what took the most time to negotiate.

In the end, my "non-disclosure" deal landed me a hefty paycheck. A deal no one outside of the boardroom would or could ever talk about. I was happy. They were not. But they had limited options, and the one they settled on was shutting me up by paying me off and having me sign a paper saying I would never be involved with another company on Wall St. Ever. Like I said. I had never done anything illegal, but what I did do, they reaped the rewards.

The rest of the day was spent cleaning up loose ends, transferring money, and meeting with my broker, Tom. In three hours, we had a deal on my old place. The couple I had rented it to were very happy I had given them a chance to make the first offer. We sealed the deal with both parties happy about the fair market value.

Tom and I celebrated with a New York City last supper. Steaks and beer. For me my last night in town was a good one. Now it was a new beginning. I was fully committed to my new California roots.

*****

"Jesus, you look incredible."

Jillian stood in front of me at the reception. She was stunning in her summery, yellow, bridesmaids dress. Her long blonde hair was up in a cool design only seen at weddings. It was adorned with woven twigs, ribbons, and small white flowers. It looked perfect.

"You only say so because you have to, cuz you're my date," she said hugging me loosely so as to not wrinkle herself.

"No. I say it because it's the truth. You are easily the prettiest woman here."

From behind her blush, she leaned forward. "Shhhh. You're only supposed to say those things about the bride."

I looked over to Stacey who was standing in some kind of formation line and smiled. Pretty, yes, of Jillian's caliber, no.

Jillian must have known what I was thinking, because she squeezed my hand and smiled.

"I'm sorry to leave you alone, but I have to get into the greeting line. After dinner, I'll introduce you to everyone."

Releasing her hand from my grip, I turned and started toward the bar. I'd get a drink or two and find the table where they placed all the misfits and wait for Jillian to join me. But my plans were not what happened.

"Hey mister. Get in line and say hello to everyone. You know all the girls and Stacey. Now you'll get to meet Paul, her new husband."

Great. Not what I had in mind.

The girls were friendly to me and introduced me to their wedding partners, yet they gave me very tentative stares.

But as I moved down the line, closer to Jillian, it seemed like I was moving into friendlier territory. But the friendly part caused my anxiety level to hit an all-time high.

"Chris these are Paul's parents, Jim and Ruth. And beside them are mine and Stacey's. Mom, Dad, this is Chris, he's the guy I told you about. Chris, I'd like you to meet Al and Beth, my parents."

Al shook my hand with a strong firm shake, and Beth looked over my shoulder and off into the distance as she gave me a not so warm welcome.

The turn of events gave me instant sweats.

I found the bar and ordered a pair of whiskeys, neat. The first didn't see me coming and slid down my throat in a flash. The second one was aware of my intentions but didn't put up a very big fight about it.

The bartender seemed to know his audience, and like a skilled professional, he tilted the bottle and poured me a pair of refills.

*****

I was the last of the eight at my table to arrive.

Someone made a comment about us being "Table 19", which I assumed was meant to be a joke about us being outsiders. And when I sat and looked around, it was more than confirmed.

The head table alone was more than enough to make anyone run for the hills. It was a wedding, and I shouldn't have been thinking about bad things, but I couldn't help myself.

First and foremost, I had slept with the bride. I had even been offered money to do so, but when it was all said and done, I did it because I wanted to. On the very same day, I slept with her sister, twice, and until she woke the next morning, all alone, she had thought I had done it for money. Three hundred dollars to be exact. And if things couldn't get any worse, I had sex with their mother. Unlike the sisters, I had no idea who she was. But Beth, Bethany, or whatever the hell you want to call her, is Jillian and Stacey's mom.

As stressed as the situation was, I found myself to be having a good time. Lots of dancing, and more than enough food and drink. It was a very good time and having Jillian on my arm certainly didn't hurt.

"He's handsome."

We overheard one of Beth's friends saying as we approached Beth and her friends.

"I suppose, but he's just a boy-toy. He drives a taxi for Christ sakes."

I stopped in my tracks. Her hurtful words hit me in the chest like a punch. Stunned, I watched as she twirled the wine in her glass, looking at the deep red color as if it held the answers to all of the world's problems and continued speaking to her friends.

"What can you do. They've been warned and warned, time and time again, but look what happens. One marries an asshole, and the other is dating a broke cab driver. Jim and I failed with their upbringing. It makes me feel sad actually."

Never one to shy away from aggressive people, I released Jill's small hand from my grip and walked up to her mother. Putting my hand on Beth's bare shoulder, I asked, "Could I interest any of you lovely ladies another cocktail?"

Beth moved her shoulder away from my touch and gave me a 'no thank you'. Surprisingly, the other pair requested more wine.

Jillian just stared at her mother in disbelief.

*****

With the reception portion of the evening complete, we headed back to Jill's condo. It was a very nicely decorated home. One where a woman's touch could be seen in every corner of every room.

I helped take pins, twigs and flowers out of Jill's hair as we prepared for a shower.

Stepping under the water I pulled her perfect body to me, but I immediately knew something was wrong. Our kiss was stale. Her body was limp, and nothing about her was aroused.

"Is everything alright?"

"I'm sorry, but no. It's just been too much information for me tonight. I'm in an overloaded state of mind. I don't know why she was so mean to you."

"I do."

"Then please tell me."

"Jill, there's no way to tell you this without it hurting you. And hurting you isn't something I want to do."

"Tell me."

It broke mt heart, but I did. I told her. I told her everything.

"Jill, are you okay."

"No, I'm currently somewhere between an emotional meltdown and a nervous breakdown. So, I'm a long way from okay. I mean, I want to believe you Chris. I want to trust you. Honestly, I do. But everything has happened so fast and weird."

"I'll say. Weird may be the understatement of the decade. Let's be honest, Jill. I hadn't planned any of this. I didn't know you or Stacey when I picked you up at your hotel. Yet a few hours later, you offered me money to have sex with both of you. And after our day and night together, I didn't hear from you for a very long time. But trust? You never need to question trust. I'm a loyal guy. Since the last time you called me, I...well...I thought we had something going between us."

Jill left me alone in the shower. Alone with my thoughts. Thoughts about my next move.

Although it was warm in her home, Jill was covered to the neck in a heavy sherpa blanket. It looked to me like she was trying to protect herself from all of her memories and demons.

"Jill, I wasn't sure we would ever even meet again. And then I had a tour of older women. I had no idea who they were. She never mentioned her family. And she never told me 'Hey, guess what, you had sex with both of my daughters', so how was I to know?"

"She knew."

"How? I haven't told a soul about us."

"She heard Stacey and I talking about our trip. We told her all about you and the wineries. She wasn't even going on her stupid trip until she found out about you."

A surprised silence filled the room. I waited to see if it was a joke, but she stayed in the same position. Rocking herself gently.

"Baby, if I could take it back, I would, but you know there's no way of doing it."

"Yeah, baby. My mother and the baby. There's one other thing and it's killing me. I mean my mother's bad enough, but every time I have to see or hold Stacey's kid, it will remind me of the two of you being together."

"Her what?"

"Her kid. Her child. Her baby."

"And what does her having a baby have to do with me?"

"Stacey told me she got pregnant out in California. She says her and Paul haven't slept together in over a month before she went on her bachelorette trip, and when she got home, she missed her period and took a test. She told me about for the first time tonight."

"Come on. There's no possible way she's pregnant. And if she was, it's not mine."

"How's do you figure?"

I didn't know how to answer. I hoped it wasn't mine. There was an outside chance it could be, but I certainly hoped it was not.

"Jill, maybe Stacey is upset about us. In Napa, I saw her later, after I left your room. She wanted...she's your sister. When the time is right, we can do tests to be sure."

We sat in the same room for the longest time without speaking a word. We were together, yet miles apart. Jill was somewhere alone with all her doors locked tight. She was protecting herself from me and the pain I had caused her. I could only sit in a chair looking at her. Felling as sorry for myself as I did for her.

She didn't even notice me texting. She wouldn't lift her head.

In the darkest part of the night, she spoke.

"Chris, I'm sorry. All of this is way too much for me to comprehend. I can't shake the thoughts of you with my mother and my sister. And the idea of you fathering her child, well..."

"Well, what. First, we aren't sure it's my child. Second, if your mother knew who I was, you should be more upset with her than you are with me."